"Tell Eddie I've finished with this for now. She's one of his better whores, but she has too much of a mouth on her," Warden Stone barked at Steve and slammed the door shut.

Part IX

I lay there stunned, how had I miscalculated my effect on the Warden? The one man who could guarantee a transfer from this shit-hole; fuck!!!!

The cravings of male sexual hunger within the confines of the four walls of Chelmsford Prison did not stop just because there were visiting days with the guards bribed to look the other way (or wantonly stare) whilst prisoners wives or girlfriends masturbated and fellated their partners in the visitors room. On completion of these visits the prisoners were seldom fully satisfied when they stuffed their sticky, deflating penises back into their grubby prison fatigues; they had the same appetites as men everywhere and wanted sex daily if they could get it.

In this rough world of imprisoned men where the inmates had only the slight chance of sex during visiting hours, I knew that when I was forced to dressed as a woman, I was enticing to these sexually deprived animals. The prisoners had only the fumbling wanks and sloppy fellatio provided by their wives and girlfriends as they dipped their hands and heads below the Formica topped tables during visiting hours.

The lack of normal heterosexual relations available to the inmates was the catalyst that allowed Eddie to make a fortune running his prison brothel with his string of transvestite prostitute inmates. Men starved of female companionship took their pleasure where they could; and there were also undoubtedly some prisoners and guards who preferred sex with transvestites regardless of the availability of women.

I was the latest addition to Eddie’s stable, and although being forced to crossdress and prostitute myself was repulsive to me, I knew from recent events that I was irresistible to the inmates and guards who found their pleasure this way. So why had the Warden been so contemptible to me after treating me so nicely at first? I had obviously overplayed my hand when I tried to make my proposal for a transfer out of Chelmsford. Stupid me! I decided that I had better come up with another solution to get out of this disgusting place. Perhaps blackmail might work where my charms had failed?

"Well Michele, you really managed to piss the Governor off somehow! Come on you naughty girl, lets get you back to your cell so you can get cleaned up and rested; you still have to work tonight," Steve said, lifting me to my feet.

He leant down and picked up my skirt and shoe from where the Warden had thrown them on the floor.

"Here sweetheart, put these on," he offered the items to me smiling.

I slid the patent leather black high-heeled sandal over my stockinged foot, my painted toenails visible through the torn reinforced toes of my pantyhose. The silver anklet around my left ankle was still there, sparkling as the light reflected off it. I slid the navy blue skirt up my legs and wiggled my pantied arse into it and tried to smooth it down my thighs. I leaned against Steve to steady myself whilst I dressed and I heard him gasp as he wantonly ogled me. The split in the side seam of the skirt exposed my sheer hosed legs right up to the top of my thigh, and I exposed a glimpse of white satin panty as I adjusted my translucent white nylon slip under my skirt. I felt Steve’s hard muscled bicep as my painted fingernails dug into his arm and remembered how dangerous this could be.

"Christ you look good Michele. With that torn skirt, laddered stockings and messed-up makeup you look like a stray waif who needs rescuing."

"And fucking," I heard him whisper to himself.

"Come on, we better get a move on," Steve pushed me through the door onto the stairwell landing.

He pushed me against the wall and pressed his full weight against me. I could feel his hot breath on my neck.

"Shhh! I think I hear someone on the stairs below us!"

"We’ll have to wait here and be quiet until the coast is clear," he whispered in my ear.

Steve pressed tighter against me, my back was pushed hard against the cold concrete wall. Steve was breathing into my ear his breath quickening.

"I can’t hear anything," I whispered.

"Shhh! If you can’t shut up I’ll have to shut you up!" he whispered hoarsely and pressed his lips against mine.

I felt the groan in the back of his throat and heat from his body. He kept his lips locked on mine and then I felt him slowly start to rub himself against me, his member thickening in his jeans and pushing against my lower body. Steve’s hands came up and pressed my arms tight against my body in a vice-like grip as he continued to kiss me and move against my body.

"Keep quiet; we can’t afford to be found here outside the Governor’s office; Eddie would kill me," he whispered hoarsely between kisses.

I tried to open my mouth to protest and he slid his tongue into my mouth and passionately tongue kissed me. I was resigned to my fate. What could I do? I was still shocked from the ravaging I had received from the Warden. Steve released one hand and slid his arm between our bodies, still kissing me and flattening me against the hard wall. He fumbled around; I knew what he was doing, and then I heard the rasp as he opened his zipper.

His hard penis leapt free from its denim prison and I felt the hard hot texture of it as it came to rest against the material of my skirt. Steve groaned again and repositioned his hands. His body now pushed me harder against wall; his right hand pushed on the back of my neck pulling my face and lips hard against his; his left hand slid up my right thigh, his callused fingers whispering against the nylon of my hose.

It was deathly quiet on the stairwell. All I could hear was Steve’s heavy breathing, the occasional groan in the back of his throat, the whispery murmur of his fingers stroking my pantyhose and the rustle of my skirt rubbing against my body as he pushed his cock against me and gyrated his hips. There was no sound of voices or footfalls.

I managed to briefly break the lock of his lips on mine and pleaded,

"There’s no one coming Steve; quick let’s get back to my cell while the coast is clear!"

"Shut the fuck up bitch!" he hissed, "There is one person coming soon and that’s me!" he confirmed his intention to take me in this cold bleak stairwell.

I squeezed my arms up between us and pushed against his shoulders in an attempt to fight him off. Steve just pulled my face back to his and carried on kissing me, thrusting his tongue over my lipstick-smeared lips and deep into my mouth. His hand on my thigh seized the hem of my skirt and wrenched it up; as he did so he adjusted his stance so that his hard hot penis pressed between my nylon encased thighs.

Steve groaned again and began to rub his engorged member in the crevice created by pantyhosed thighs. I locked my thighs together in a vain attempt to stop him. Steve now repositioned his hands and bought them both down to my buttocks, taking one buttock in each of his big strong hands, squeezing them through the material of my skirt. The hem at the front of my skirt remained ridden up so that his cock was nestled in the ‘Y’ shaped silken valley created by my hosed thighs and white satin panties. Steve now began to push his steel hard member in and out of this silken trap, his cock pressing further between my legs with each thrust. He was ‘dry humping me’ the dirty bastard!

I beat my fists against his hard muscled shoulders trying to discourage him, but it was useless. Steve now lifted my buttocks upwards and as he did so my body slid up the wall and my feet lifted off the floor; Christ he was strong! My high heels left the ground and as Steve continued to lift me up against the wall he pushed his body weight against me, forcibly opening my legs. As hard as I tried to press my legs closed, the force of his body and his strong arms proved no match for by feeble efforts as my fists drummed against his chest and shoulders.

Steve suddenly heaved me up and at the same time repositioned his grip under the tops of my thighs as he pushed me back against the wall with his bodyweight. My feet were now completely off the ground and my thighs spread further, unencumbered by my torn skirt. Steve pressed his groin into me and I felt his turgid penis throbbing against the satin gusset of my panties. He adjusted his position slightly and I felt his member begin to slide under the gusset of my panties and push against the sheer nylon crotch of my pantyhose.

Steve was panting with excitement and exertion; his hot breath was in my mouth and then on my cheeks as he kissed me hotly on my lips and face. He moaned,

"Michele; please………I’ll be gentle honey……..God you’re so lovely!"

What could I do? Resistance was futile and would probably only cause me pain.

I moved my hands from his chest and wrapped them around his neck and slid my nyloned calves around his waist. Had anyone come up or down the stairwell they would have been greeted with the following sight:

A large muscular man embracing a petite businesswoman, bracing her up off the floor and against the cold brick wall, her arms locked in embrace around his bull neck whilst her legs were locked around his waist to help support her weight. Her painted toenails peeking through patent leather black high-heeled sandals, her sleek legs sheathed in laddered, diaphanous sheer black nylons, with dark reinforced cuban heels and toes, the seams of the nylons running up the backs of her legs.

She wore a navy blue suit. The skirt was ripped up one side and was snug at the waist and tight around her hips and bottom. A glimpse of translucent white nylon full slip was visible where her skirt was torn and where the front of her skirt had ridden up as she clutched herself to the muscular inmate who held her captive. A flimsy white nylon blouse peeked through her navy blue suit blazer designed to match her skirt.

An observer would then notice her pretty feminine face. She wore pinkish hued eye shadow, blended with light aqua to just under her eyebrows. Lashings of black eyeliner and mascara had been applied to her lids and lashes and had smudged around her eyes and had run down her cheeks from the tears she had recently shed. Her plum coloured lipstick was smeared around her lips from the frenzied kisses that had been forced upon her. Her hair was a black bob wig, and a pair of silver and diamond encrusted sapphire drop earrings hung from her ears, a matching pendant around her neck.

She looked defeated and submissive as the powerful thug supported her, pushing her against the wall as he thrust against her grunting and panting whilst he defiled her.

Steve was kissing me hard, his tongue assaulting my mouth. His rampant member slid back and forth, snug between the nylon of my pantyhosed crotch and the satin gusset of my panties. He picked up the pace and pushed his cock harder into the crevice between my buttocks. He settled into a steady rhythm as he dry fucked me, his pelvis thrusting back and forth as he pleasured himself. I just hung on and offered no resistance, allowing him to gratify his primal urges; I just wanted it over with. I responded to his kisses and pushed my arse against him to increase his pleasure and hasten his climax.

Suddenly Steve slammed me against the wall and thrust forward and upwards with all his strength. I felt the glans of his member push firmly against the nylon of my hose and then felt the thin gauzy material stretch and finally give. His rock hard penis nestled in the bud of my sphincter and began to shoot hot spurts of semen. The warm slick liquid lubricated my puckered bud and his member slid deep inside me, pulsing and spewing streams of his seed into my back passage. Steve’s tongue pulsated in my mouth and I responded as I felt an uncontrollable wave of please wash over me.

The head of Steve’s penis was pushing hard against my prostate, his vibrating rampant flesh shooting hot jets of come inside me causing me to orgasm spontaneously. I suddenly emptied my seed into my silky pantyhose and satin panties that encased my sex organs. Steve’s crotch pushed the filmy material against my scrotum, increasing the sensations as they shot through my body, amplified by feel of the sheer nylon hose on my legs and the silky full slip and blouse on my torso.

Steve thrust me hard against the wall as he emptied himself inside me; I groaned and forced myself against him. Steve shuddered and moaned, torrents of semen spewed from his member and dribbled out of me, pooling in my panties.

As our orgasms subsided Steve eased me slowly to the ground and as he did so his cock slid from inside me unleashing a further torrent of come into my undergarments. I tottered on my high heels and held on to him, the last of our kisses becoming softer and tender until I was standing there on shaking legs, my back against the wall for support. Steve adjusted himself and zipped up. He leaned forward and pressed a light butterfly kiss on my cheek.

"Come on honey lets get you back to your cell before Eddie comes looking for us," he whispered, and nuzzled my neck briefly.

As Steve led me dazed and confused up the stairwell and back to my cell I began to realise what had just happened. Again I felt repulsed by my uncontrollable sexual responses. I loathed myself for capitulating and even worse for taking pleasure in the sick, twisted sex life into which I had been enslaved.

Steve dropped me off at my cell and made me strip. He took away my female attire and led me to the showers. He stood guard while I washed off my makeup and showered in the empty cellblock ablutions, the other cellblock inmates were at work but he was taking no chances that anyone might decide to have some fun with one Eddie’s ‘girls’ out of business hours. I have to say I felt better knowing that Steve was there to watch my back whilst I was in there alone. Steve didn’t say much to me at all after I had taken off my female clothing and washed off my makeup; it was as though he had no time for Mike, he just lusted after ‘Michele’.

I spent the last part of the day alone in my cell contemplating how I was going to get out of the mess I was in. I watched the clock, dreading the passing of time as the minutes advanced into hours. ‘Iron Bar’ Steve finally knocked on my cell door and entered,

"Time for work; let’s go," he said.

Steve led me back to E Block, the deserted wing that Eddie had set up as his brothel. He handed me over to Mabel who told me to strip. She inspected me all over as I just stood there meekly letting her prod, poke and stroke me.

"You need a good shaving girl," she clucked, and led me down to E block’s shower rooms.

She had me sit on a stool and shaved the light stubble from my face and then proceeded to remove any remaining hair from my arms, legs and chest. She then rubbed moisturiser all over my body and dressed me in a light blue satin kimono.

"Come on love, you can get ready for work in your workroom," she muttered leading me out into the corridor to my workroom cell.

‘Ready for Work! Workroom! Who the fuck was she kidding,’ I thought to myself. ‘What she really meant was go and make yourself into a woman so the sick bastards in this hellhole can violate you!’

As I passed down the corridor two of the cells had low red lamplight emitting from the flimsy curtains which had been pulled across the bars at the front of the cells. I heard muffled grunts and groans, and as I passed the first cell I heard the slapping sound of flesh against flesh. I could just make out the silhouette of what appeared to be a woman bending over a chair as a large man stood behind her pounding himself against her buttocks.

I could just make out that her panties were pooled around her ankles above ridiculously tall high-heels. As the large man plunged forward into her she shuddered and tottered on her heels, she held on to the back of the chair and the legs of the chair made a scraping noise each time she was pushed forward slightly with each thrust. The man appeared to be fully clothed and grunted like a pig with each lunge of his body; he held on to her tight at the waist. The woman, actually a crossdressed whore, gasped as each thrust rammed his groin against her buttocks with a loud slap.

I couldn’t see anything in the second cell; I could just hear the slurping sounds associated with a well-trained fellatrix at work and the murmurs of a man being satisfied.

"Just Carmel and Charlotte servicing a couple of guards before we open for business," Mabel said as we passed by on the way to my workroom cell.

"Eddie gives the guards a freebie and they keep watch for him and keep out the rabble. Business is business in Chelmsford prison honey; we all have to pay our way," she sniggered.

She led me to the cell door and I noticed that heavy curtains had been rigged on a rod above the cell bars that opened on to the corridor. They were pulled back at the moment but they did not bode well for me this evening I guessed. Mabel pushed me through the door and walked over to the armoire. She rummaged around and pulled out what appeared to be a schoolgirl’s uniform.

"You’ve got a ‘special’ first up love; get dressed, Eddie’s bringing a friend in half an hour."

"He wants to play ‘Naughty Schoolgirl.’"

Mabel rummaged around in the drawers and selected lingerie that she threw onto the oversize cot. She looked at the assortment of wigs and selected a blonde, shoulder length wig.

"Shame we haven’t got time to make up some pigtail braids on that wig, but he’s not really that fussed on authenticity if you know what I mean; it’s more of a costume dress-up thing with him," she shrugged.

"Well come on love, get a fucking move on!" she ordered and pottered out of the cell to go about her duties.

"Fucking old tranny fag-hag!" I hissed to the empty cell after she had left.

I knew the routine well enough by now and resigned myself to getting dressed; failing to comply with Eddie’s orders would only result in a beating.

I sorted through the lingerie on my cot and laid it out so I could dress with a minimum of fuss. First I slipped a red satin garter belt around my waist and clipped it together at my belly button. I twisted it around so it faced the right way, smoothed out the satin panel at the front and straightened out the three red garter straps connected to each side of the belt.

Next I slipped into the nearly nude sheer nylon stockings Mabel had selected. I pulled each one up my freshly shaven legs and attached my suspender belt to the reinforced lace panels at the top of each stocking with the three garter straps. As I smoothed out the wrinkles in the delicate nylon along my legs little sparks of sensuality ran through me. I shrugged the sensation off and continued to dress.

Next I stepped into a pair of boy-leg lace paneled knickers. They were gray nylon with a white lace insert at the front and around each leg opening. The lace trim matched the lacing on my stocking tops. I shrugged into red satin full-cup bra which matched the garter belt. I walked over to the makeup table and opened the drawer that contained my breastforms and pushed them inside the bra cups. No time for adhesive if Eddie was due in twenty minutes. I adjusted the bra and breastforms so that they appeared as natural as possible.

Eddie obviously did not care too much for authenticity; Mabel has selected a pair of patent leather black high-heeled court shoes. They slid easily onto my stockinged feet and as I stood I was relieved to find out that it was a lot easier to balance on these wedge heels than the tapered spiked heels that I had been forced to wear up to now.

I sat at the makeup table and adjusted the lamp so that I had good light to apply my makeup. It still amazed me how quickly I had become adept at the feminine art of applying makeup!

First I applied the foundation and powder. My eyes I decided, would be in dark shades so I applied dark gray eye shadow and black eye liner. I underscored the eyeliner on my lower lids with a thin dark blue line for contrast. I applied lashings of mascara so that my lashes were almost caked with a thick black coating. I lightly applied a dark shade to my eyebrows with the eyebrow pencil and completed the look with a light pink shade of blush on my cheeks and only a slightly darker shade of pink lipstick. I decided to experiment this time and applied a coat of lip-gloss. I pulled on and adjusted my wig; just the look I wanted; I looked like a naughty schoolgirl with the lighter shades of makeup I had applied but with my dark eyes contrasting wonderfully.

Next I put on the long-sleeved cotton blouse, being careful to keep the pristine white garment free of makeup. I buttoned up the blouse, still finding trouble with the way women’s clothing buttoned on the opposite side. I pulled the school uniform tunic over my head and adjusted it. It was a dark blue and green tartan. The dark colour emphasised my pale face and dark eyes. The bodice was tight against my torso; the skirts were pleated and came to just above my knees. Then I had an idea; the finishing touch!

I rummaged around in the drawers until I found what I was looking for. I sat on the edge of the bed and kicked off my court shoes. I pulled on a pair of white cotton anklets over my stockinged feet and then stepped back into the black patent leather court shoes. I looked fantastic! I left my ears unadorned but slipped a simple gold chain necklace around my neck.

I sat back down on the bed and started applying two coats of pale pink nailpolish to my nails. While I was doing this I had time to think and realised what I had done. ‘My God! What the fuck was I doing!’

Not only was I capitulating with the crazy bastards who forced me to become a crossdressed prostitute; I was dressing like a woman as if it was a natural thing to do! I was working at looking good and even being innovative to achieve the ‘look’. Fucking white anklets; what the fuck was I thinking of!!!! Had these sick fucks brainwashed me?

I was about to get up and do; I don’t know what; remove my makeup and clothes? rebel? scream? then I heard the unmistakable sound of Eddie’s voice as he approached.

"Oh fuck yeah Dave, you will love my latest acquisition! She’s got an arse to die for; and with only a little bit of training she already knows how to suck cock like she was born to it."

"I don’t trust the cunt though; she’s too fucking smart by half," he added.

"Smart mouth on her; and you can tell she’s planning something. You have to remember this twat ain’t like Charlotte and the other dumb cunts in my stable; he was a businessman, pretty smart and well to do on the outside until he got done for running some kid over while drunk."

"She still thinks there’s a way out of her job here, and I’m sure she’s got ideas about getting outside or transferring to somewhere else, so be careful if you take a fancy to her; she might try it on, like I said, she’s just too fucking smart!"

Eddie was obviously discussing me with the punter he was escorting to my cell. So Eddie knew I had plans to try and get out of the fucked up predicament I was in. So what! If I got my chance you can bet I’d be gone in a flash!

Then it dawned on me what Eddie had said, ‘so be careful if you take a fancy to her’.

‘Maybe that meant my first customer of the night might be a man of influence and power,’ I thought.

‘Maybe I could use him to my advantage? Better be careful though; I had fucked up royally when I tried it on with the Warden; best find out all I can about this guy before I try to use my newfound charms on him,’ I considered.

"Well hello Michele; don’t you look lovely this evening," Eddie said with an evil smirk on face as he stepped into my workroom cell.

A tall good looking man dressed in prison fatigues walked in behind Eddie and came to a complete stop in the cell doorway and looked me up and down where I sat on the edge of the bed.

"Christ Eddie she’s a stunner all right; you weren’t exaggerating on bit. Hi sweetie," he said pleasantly, walking all the way into the cell.

"Say hi to my best friend David, Michele; don’t be rude!" Eddie smiled my way.

"Hi David," I said in my best attempt at a coquettish voice.

"Davy here is a very special friend of mine Michele, and I promised him that you would treat him very nice this evening; so you do that for me and maybe I’ll be nice to you later ok?" Eddie said in a voice that left no doubt that if I wasn’t nice to Eddie’s friend I would be very sorry.

"Of course I will Eddie," I answered meekly.

"So Davy, will she do; is the get-up ok?" Eddie asked.

David had been looking me up and down ever since he arrived in the cell; he hadn’t taken his eyes off me.

"Yes Eddie she’s perfect, and I bet she can be a very naughty school girl too," David chuckled.

"Yes; and speaking of being naughty; Davy why don’t you go and see Mabel and bring yourself back a bottle of something to drink while I have a little chat with Michele. Just give us five ok?"

There was no doubt that although Eddie was treating David with more respect than I had ever seen him treat anyone else, Eddie was still the one giving the orders.

"Sure; is scotch ok Michele?" David asked my way.

"Fine," I answered.

David ducked out the cell and I heard his footsteps disappear down the corridor. As soon as David left the cell Eddie strode over to me and held out his hands.

"Stand up sweetheart and give us a good look at you," Eddie said.

I allowed Eddie to assist me to my feet. He looked me up and down and smiled.

"Wonderful," he said. Then with lightning-quick speed he punched me in the stomach.

"You fucking cunt! What the fuck do you think you were playing at with the Warden? Me and you are going to have a little chat later and I’m going to remind you how things work around here!" Eddie barked.

I collapsed on to the bed, the wind completely taken out of me. I doubled over in pain as I tried to breathe. I felt like I was dying, I couldn’t get any air in my lungs.

"Don’t you start crying and ruin your face you fucking cunt bitch," Eddie snarled.

"You fucking soak up that pain and get yourself ready. David is my best friend in this shit-hole and I promised him you would treat him special, so you just get your pretty arse off that bed, breathe deep, and be ready when he gets back here."

I forced myself to stand and eventually I could breathe in shallow breaths but the pain in my stomach was excruciating. Even so I realised that I was lucky that Eddie had bought his best friend to see me otherwise he may not have cared about marking my face with his fists. I stood there looking down getting my breath back.

Eddie lifted my face to his,

"You try any of your fucking smart moves with Davy, Michele and I’ll put you in hospital you bitch. I’ll accept the loss of earnings while you recover; besides some cons in here like being sucked off by bitches with no teeth; slides in nice and easy so they say, so you fucking well behave," Eddie threatened.

He released my face just as David walked back through the door with a bottle of scotch in his hand.

"I’ll leave you two kids alone to get acquainted ok?" Eddie sniggered.

He pulled the heavy curtains across the bars to my cell, slipped through them and slammed the door shut.

"Don’t disturb them for a couple of hours Mabel," I heard Eddie yell at her as he walked off.

I was alone in the dimly lit cell with David; we had complete privacy. David looked me up and down again.

"Drink Michele?" he asked, a smile breaking out on his handsome face.

"Please," I smiled back suppressing a grimace of pain from where Eddie had punched me.

David half-filled two glasses with hefty shots of the dark amber liquid and handed me one.

"Michele you are one pretty lady if I may be so bold. And that schoolgirl outfit is just as kinky as hell," he said grinning at me with the confidence the way only men secure in their good looks seem to be able to do.

He suddenly came over serious.

"Don’t get me wrong; I’m no noncer or anything. I like to take my fun with adults not juveniles; it’s just that I love trannies when they get dressed up in sexy costumes like that."

"Oh fuck I’ve done it again; I’m sorry I didn’t mean anything derogatory calling you a tranny."

"Shit, I’m behaving like it’s my first date; let me start over."

We both looked at each other and suddenly burst out laughing. It was honest laughter bought about by David’s embarrassment and stumbling apology. He was very handsome indeed; tall and slim with black wavy hair, deep blue eyes with laugh lines at the corners, white teeth and full sensuous lips. He was deeply tanned and obviously made the most of his allocated time in the exercise yard.

"Alright. Michele, I’m David but please call me Davy."

He took a big gulp of scotch and continued.

"I’m what you might call a business associate of Eddie’s; let’s just say I do him favours and he does me favours."

"I’m fourty something, single, bisexual and disease free," he laughed again.

"And oh; to be honest I do have penchant for transvestite hookers dressed up as school girls," he finished, laughing again in his easy way.

He had managed to put me at ease and I could see how he could easily win over any woman that took his fancy; or man for that matter, he did say he was bisexual after all!

"Hi Davy, I’m Michele and a woman never tells her age," I smiled back at him, taking a sip of the single malt.

"As for the rest……..", I started but Davy interrupted.

"I know the rest honey," David said, "and don’t worry I’m not here to force you to do anything you don’t want to do. Please sit."

I sat down and as I did I winced in pain as it flared up where Eddie had punched me.

"The prick! He hit you didn’t he; while I was gone getting the scotch, the bastard hit you," Davy said and sat down beside me and took my hand.

"If it had anything to do with me I’m sorry Michele; I don’t know how anyone could be cruel to you."

I was taken aback, but wary. So many times since I had been forced to crossdress men had started out being nice to me and had then turned vicious.

"No it was my own fault," I answered, "I did something stupid and paid the price."

"Well I don’t believe that a lovely creature such as you could do anything wrong; and anyway the most you would ever get from me is a light spanking on your tidy bottom," he started laughing again and I couldn’t help but laugh with him.

We both looked down into our drinks and took a sip as the laughter died down into an awkward silence.

Davy put down his scotch and turned towards me, he reached and gently turned my face to his.

"Look Michele, I do know your situation; Eddie told me the whole story. I know you are being forced to this against your will; and as I much as I would love to make love to you I an not going to force you to do anything that you don’t want to do."

"Don’t get the wrong Idea, I often come to Eddie’s stable and go with the girls here; I do love making love to transvestites; but most of the girls here are willing to do what they do, even if they were initially forced or blackmailed into it by Eddie."

"But I have never forced myself on another person and don’t intend to start now," he finished.

I was quite taken aback, Davy seemed to be the most genuine and gentle man I had met since I got into this mess; and he was just stunningly handsome. I figured that if I was going to have to pleasure punters all night, I might as well pleasure someone who is kind, handsome and obviously has some sort of influence in this place.

I had badly miscalculated with the Warden; I decided I would put my efforts into making Davy happy and play him along until the time is right to use his influence somehow to help me get out of this jam. Tonight I was his.

I reached out with my long feminine fingers with their pink painted nails and stroked his face.

"Davy you are the nicest man I have met in this place; how can I not like you?" I smiled and gently pulled his face to mine.

I kissed him on the lips and slid my tongue inside his mouth and ran it along the top of his gums; women had done this to me before and it drove me wild. Davy responded and took me in his arms. I allowed him to pull me against him as he held me tightly but tenderly. He didn’t try anything else for over five minutes; he was just contented to kiss. We kissed deeply and passionately, and besides the smoky taste of the scotch, his breath was as sweet as a baby’s. I was becoming genuinely aroused; it was not just lust invoked by an instinctive response to stimulation, but a slow sensual awakening of my pleasure centers.

Davy eased me down onto the bed, never breaking the kiss. We ended up lying side by side our lips locked. After what seemed like an eternity of passionate kissing I was ready for more; my senses were actually screaming for further stimulation. My cock was straining against the lace panel of my boy-leg knickers, the lace stimulating my member. I pulled myself closer to Davy and lifted my leg up and over his body, the pleated tunic rode up my thigh and exposed the matching lace stocking tops of my nude nylon stockings.

Davy got the hint and started to stroke my legs and thighs, his hand sliding slowly and gently along the nylon. I kissed him deeply and growled in the back of my throat as the sensation caused by Davy’s hands stroking my nyloned leg aroused me further. I started rubbing my crotch against his hard body in attempt to further stimulate my penis. Davy sensed what I was doing and gently eased me away from him slightly; I couldn’t contain my disappointment.

But Davy didn’t miss a beat, as soon as our bodies were separated far enough, he slid the hand that was stroking my leg under my skirt and went straight to my penis. He gripped it lightly through the lace panel of my knickers and began to slowly stroke it.

I groaned and Davy responded by sending his tongue into a frenzy in my mouth; it rolled around my tongue and tickled my cheeks and gums; he was an excellent kisser. At the same time he increased the speed of his hand stroking my turgid knicker-wrapped member. I knew that I couldn’t hold on to my orgasm much longer and tried to pull away; I realised that Davy had seduced me to the point where I would let him do anything. I had allowed the tables to be turned; I was supposed to seduce him into my power, not me into his!

I was too far gone, I made a feeble attempt to extricate myself and gave up immediately as Davy tried to hold me where I was, lying beside him. We were joined at the mouth, out torsos pressed tightly together as we continued our passionate kiss. I was twisted at the waist so that my legs lay open on the bed. My legs were now spread wide, my skirt up around my thighs, the sheer nude hose on my legs running down to the cute cotton socks and the patent leather black high-heeled court shoes.

Under my skirt Davy’s hand was now stroking me hard and fast through my knickers; I began to buck and writhe as my orgasm approached. My orgasm rocketed through me; I felt it through my own body. My senses were heightened to the pitch where I could feel, taste and smell everything intensified one hundred fold.

I could taste my lipstick mixed with Davy’s sweet breath and the musky scotch we had drank. I could feel his tongue jack-hammering in my mouth, my long sleek nylon encased legs were sending those little electric shocks of pleasure I had become to love so much. I could feel the satin bra and suspender set, smooth against my bare skin, and the gray nylon knickers rubbing against my buttocks and scrotum as Davy gripped my cock in the front panel of the knickers and strocked me furiously.

I could smell the sweet perfume I was wearing and Davy’s masculine after-shave, mixing with the musky hint of sweat as we both became further excited. Then I could smell the slightly starchy smell of my semen as I spent into my knickers.

My climax shot through me, and I shuddered and groaned. Davy continued to stroke me, milking my seed into my knickers, the semen lubricating the lace and increasing the intensity of my orgasm. As the last of my emission dribbled into my knickers Davy released his grip on my erection and slid his hand under my silky buttocks and turned my lower body towards him, his hand on my ass pulling me close against him. I lifted my leg again, rubbing my stocking leg against his muscular thigh, milking the last sensations that I could out of my subsiding orgasm.

Davy held me like that, our bodies side by side, for about five minutes; never braking our kiss, my lips were almost numb. Then he stopped kissing me and looked into my heavily made-up dark eyes and said,

"You like?"

"You bet," I responded smiling into his handsome face.

Now that we had stopped kissing I pulled myself free of our embrace briefly and Davy frowned; but not for long as I readjusted our position on the bed. I pushed Davy onto his back and I straddled his waist, my pleated schoolgirl skirt spread over his middle. I leaned down and kissed him briefly on the lips and then pulled back so I was sitting upright. I looked down into his beautiful deep blue eyes and said,

"Now, what can this naughty schoolgirl do for you?"

 

To be continued………………….

Those hands get back to my legs, caressing my thighs, getting closer and closer to my crotch. Then, a little snap sound, the undoing of the crotch in the bodysuit brings me alive. I open my eyes and I am in shock. It takes me some time to realize what is going on, the hundred hands caressing my body are only two now. I open my eyes wide, I can’t believe what is happening, I am really in shock. But, dam I am so horny, so hot, my mind is fogged by the feelings, by the rum, by the suddenly broken dream.

I try to focus, and try and can’t believe what I see. So I try to focus, I try to wake up. But I am awake, and the hands caressing my body are real, and the feeling is real, and it feels, oh, so, so very nice!. So very good!. The body suit crotch is up to my navel now, and the hands are softly caressing my belly, going down, down, stopping a millimeter short of my dick, and doing it all over again, then going to my thighs, caressing them over the soft cloth of the pantyhose, coming up, up, stopping a millimeter short of my balls, and going all over the same route. I really do not know what to do. I want it to stop, it is so embarrassing, it is so wrong, and at the same time it feels                                                                                                                                                                                                                                                                                                                                                        so good, oh Lord, it feels so good I don’t want it ever to stop.

At this point I am about to shout to stop, quit, hold on the torture, but one of the hands, softly, deftly, kindly, erotically gets to my belly and slides under the edge of the pantyhose, sliding down, down, down, all the way to my crotch. Gets a good, magnificent, erotic, fantastic grip of my cock and begins to stroke it, slowly, deliberately. The other hand is not far behind, but, instead of grabbing my dick, keeps going down, down, past my balls, to my ass. Now it comes back, to my dick, to the very tip of my dick, rubs the tip, gathering pre-cum, a lot of it is coming out  now, so this fingers grab a lot of it, and run down again, down to my ass, and with the soft natural lubricant begins to rub the rim of my boy pussy. I hear myself moan, I feel myself pulling my legs apart, spreading them as wide as I can, and searching with my body, with my ass the firm touch of those fingers.

Now I feel the warm breath of a mouth in my belly, the warm touch of a tongue around my belly button, it is licking me all over, going down on me, towards my crotch, but not getting there, coming back up to my belly, pushing the body suit up, licking my stomach, trying to get further up, while the hands, the fingers are still down there, down my navel, on my crotch. I do not know what to do, my mind is not responding, I push my body up, and grab the bodysuit to pull it up, past my stomach, up to my neck, leaving the rest of my body naked, free to my assailant to do what HE wants to do. I can’t deny it anymore, my eyes are wide open, uncle Sandy is fondling me, kissing my body, sucking on my boy tits, gently, slowly, deliciously jerking my dick and, better of all, yes, better, finger fucking my ass to OUR hearts content. I grab his head, and pull him up, I want to kiss him, and he obliges. We deep kissed, out tongues looking and searching and finding each other’s. His hands are still down there, stroking gently my cock, his fingers in and out my ass. His mouth in mine, his naked body against mine. His hard cock, I realize for the first time, rubbing against the soft cloth of the hose in my left thigh. Hard, long, thick, hot. I reach for and grab it, it feels so nice in my hand, so hot, so hard, so fleshy. I try to lean to look at it, but Sandy stops me with his own body, he has taken the lead, and now, bent over, he is reaching for my dick

The warm feeling of his lips around the head of my aching cock is almost too much, and the finger fucking of my ass is really getting my head to where I suppose it should never get. I begin to feel anxious, guilty, ashamed, hot, horny, full, complete, gay, dirty, queer, fulfilled, free. I hear myself moaning, begging, asking for mercy, for delivery, for an end to my exquisite torture, for him not to stop, not to let me come, never to stop, to keep doing what he is doing forever, to fuck my ass, to eat my dick, to let me have his dick, to kiss my mouth. The response I get, is really the last one I was expecting, as my aunt Sally interrupts my train of thinking, if you can call it thinking, by gently whispering in my ear

-‘hey honey, are you having fun?’

My heart almost stopped, there and then. I thought, I’m busted, this is it. I’m dead.

But Sandy, instead of stopping, panicking or anything of the sort, got my dick completely inside his mouth, and two fingers in my ass, just kept going in and out, while his other hand just got hold of my balls, gently squeezed them, bringing me real close to an orgasm, but at the same time grabbing firmly around the base of my dick, preventing me from cumming.

 -“Can I join ? – Sally asked rhetorically, while at the same time straddling over my face, depositing her clean shaved pussy on my face, all over my mouth. – come one Jackie, let me teach you how to please a girl. Use your tongue, get it as far inside my cunt as you can, good, now in and out, in and out”.

I did as told and was rewarded by a fantastic taste of womanly juices, kind of salty, kind of sweet, but all in all delicious.

 -“Now, try to get your tongue further, to the front of my pussy, look, feel, find the little button, find my clit, good, for a first timer you have no problem, now, suck it like it was a tit, like it was a lollipop”.
 
I was enjoying this greatly, her juices were delicious and plentiful, when I got hold of her clitoris with mi lips, I immediately felt how it grew in my grip, and after a few minutes of sucking like she asked me to, I was rewarded with a continuous flow of juices, and moaning and crying. My face was all wet with her, I was so enthused I had almost forgotten Sandy, who was sucking on my dick like there was no tomorrow.

Suddenly Sally got off my face, leaving me with the delicious feeling of Sandy eating my dick, I was so close to orgasm again, and of course he knew it, he got hold of the base of my penis again, tight, very tight, until somehow he felt my orgasm was subsiding, then he let go. I was really going crazy now, I wanted the relief of ejaculation, but dare not say a word may they stop playing with me. But what followed really left me dumbfounded, they actually stopped cold. Sandy pulled my pantyhose up again, leaving it as it was, Sally helped with the bodysuit, pulling it down my body, closing the snap on the crotch again, I really was confused, I didn’t know what to do, both kissed me in the mouth, and finally Sally said:

 - “Honey, this was fun, we must do this again, but today it should be enough, just a taste of what is in store for you in the future, and besides, you can’t be wasting more time in idle games, you need to dress up for your party tonight. You need to have all the energy possible, you may get laid. You know, I lost my virginity on a prom like you are having tonight”.

With that and a last kiss from Sandy they left. I lay there on my bed, my mind a mess, my dick and balls aching from the unrewarded effort. My ass was so hot too, I still could feel the fingers going in and out of me and I ached for the real thing. Finally I got up and looked at myself in the mirror again. To my ultimate surprise I could see my crotch, a puddle of white semen, running down my thighs. I could not believe it, I had come, and in a big way and had not felt it. Oh my.

" We got all  night baby don't argh what the fuck?" i screamed as she spanked me so hard my eyes watered.

" Don't talk back to me" she spanked me again making me whimper. " Get on your knees and crawl to your room."

I thought there is no way im going to get dominated she is not dong this to me but then i realised i was already moving and doing as she said plus i was so turnrd on i could feel my juices drip from my pussy.

"Come on you worthless bitch" she yelled as she kicked at my pussy. The pain shot threw me as i collapsed on the floor in tears. She picked me up and placed me back on all fours." get moving you whore"

" Im not a whore." i whined like a silly little girl

" Really? your really wet for a good girl" she shoved two fingers roughly inside me moved them around and then pulled out her soaked fingers before showing me them. " Look how wet you are whore." she forced the fingers in my mouth making me suck them dry." On the bed spread your legs arm above your head." i did everything she said as quick as i could. She walked around tying me to the bed she then turnrd on some music and danced sexualy around the bed stripping out of her clothes as she went. She got down to her panties and i just stared at her tits perfect in every way, she turned her back on me as she took of her panties. I couldn't take my eyes off those beutiful tits as she walked over to me forcing her knickers into my mouth. I felt something brush against my arm as she gagged me.

" are you ready for my cock." she whispered i realised what had brushed against my arm

" no get away stop it no please." i screamed but the gagged made it into a mumble. Her huge cock thrust inside me ,y tight pussy streched as far as it could go. She didn't care for my body as she pumped my pussy so hard slapping my tits as they bounced around. Tears rolled down my face in pain and the fact a shemale had tricked me into bondage. Thankfuly she pulled out and removed my gag.

" how dare you do that to " i didnt have time to finish as she rammed her cock in my mouth pushing it deep in my throat. she picked up my phone and took photos of me as i was forced o suck her cock. she came soon after, she pulled out stood over me wanking her cock then unleashed her spunk over my bofy and face. She again took photos on my phone.

" are you my bitch?"

" no" i cried

" do  you theae photos sent to your friends?"

" no don't please"

" are you my bitch?"

"no" i whimpered

" send to all " my phone bleeped as the photos sent

" No please no"

" have fun explaining that baby" she said as she walked out of my flat leaving me tied naked to my bed covered in her spunk 

She continued bouncing and rocking until she melted and went limp. I took over from there; I got up and bent her over my desk. I rammed my cock up her ass and grabbed her schlong as well. I milked her cock as I slide my shaft in and out of her ass. I couldn’t last very long and couldn’t control it but I squirted my cum into her ass while she was hollering for more.

She fell onto the desk and I fell back into my chair. We rested up a minute and she said now suck me will you please… I bent down in a subservient position and took her long shemale rod in my mouth. Sucking a cock for the first time was a great experience. I could taste cum and wondered what it would feel like for her to cream in my mouth. Would I gag, throw up or enjoy the hell out of it. I sucked and licked and now in again I would gently run my teeth over the head of her cock. She began shivering and cum began shooting into my mouth. This was not too bad I thought as it shot to the back of my throat. I actually liked this and drank every drop of her sweet shemale wad!

This was indeed the best gift that I could ever dream of getting from our satisfied client.

I followed her home and watched her over the next couple weeks, learning what her habits were, where she lived, what her name was, hell I probably knew more about her than I did myself. Diane was only 20 years older than myself, she always dressed like a slut and always shot down any man that hit on her. Thats okay she'll get whats coming to her and more.

Here she comes now, what this she bought a new outfit, I wonder how slutty this one looks?

She started to walk past my van when I jumped out and grabbed her I threw her in to the van and closed the door, she started screaming and tried open the door. I laughed because i had the child locks on. I jumped in and drove out to my cottage.

I dragged her into the house and down to the dungeon where she would be staying. I threw her bag in after her.

"Get changed slut. Your going to be my slave like it or not. I'm going to get something to eat"

With that said I left and locked the door behind me. I grabbed a bite to eat and had a shower.

Upon my return I found her dressed in a red mini skirt that just barely covered her ass, A black tube top that barely held her 34 C chest, and a nice pair of red fuck me pumps.

"Come here slave and let me get a better look at you."

"Forget it dead beat i'm leaving and you can't stop me"

"First off slave there is no way you can leave. Second YOU WILL CALL ME MASTER, DO YOU UNDERSTAND ME SLAVE?"

she looked shocked that I yelled at her.

"I'M NOT CALLING YOU MASTER" She yelled back after a few moments.

With that I walked over and slapped her so hard that she fell to the floor. She layed there holding her face and crying.

"Now if you don't want me to hit you again then get up and stop your fucking crying slave."

She stood up "I'm not your slave you fucking bastard"

I smacked her face again, this time she was more prepared for it and didn't fall.

"Now appoligize slave"

"I'm not appoligizing to you asshole"

I grabbed her and put her over my knee. I layed ten good smacks on her ass. She was really crying now.

"Please stop. It hurts too much"

"Are you going to call me Master and do as I say?"

"Yes, I will call you Master and do as you say. Just don't hit me anymore"

"Well then, lets see how willing you are. On your knees slave"

She stared at me for a moment before dropping to her knees.

"Now pull out and my cock and suck it slave"

She slowly undid my pants and pulled out my now quite hard cock and started licking the head of my cock while slowly moving her small hand up and down my cock. She then took the whole length in her mouth, I started to moan.

I suddenly felt a lot of pain in coming from my sack. I looked down and saw that she had taken her mouth off my cock and grabbed my sack and started pulling it hard. I had almost passed out from the pain.

"I may be a slut but it looks like your going to be my slave."

I was shocked by the turn of events "okay you can leave just let go of my balls." I groaned.

She stood up and pulled off her skirt. revealing a cock that was bicker than mine.

"What the fuck?"

"You picked the right girl to try to rape, no start sucking bitch"

I just sat there staring, she then grabbed my head and moved it towards her. I opened my mouth and reluctently took it in. I could only fit about half of it in without gagging, although it was not enough for her, she forced my lips to the base. I started to gag and she let go i moved my head back and she slammed it forwards again. This time i didn't gag as soon. She kept slamming her cock into my mouth hard.

"Do you have any lube slave?" she asked me.

"Lube? no. What would I need lube for?"

"Sucks to be you" she said. She then pulled me up and spun me around. she took her cock and placed it against my anus.

"The spit you left on my cock will help, not by much though."

I ground as i felt her pushing against my anus. I didn't think it would enter.

I turned to laugh at her when she spit into her hand and rubbed my anus with it. She then tried again, this time my anus started to give way. It felt like she was trying to shove a house in there. She kept forcing her way in my virgin hole and held it there when she got to the base. By this point i was on the verge of crying.

"Oh come on now I can tell you like it, look how hard you cock is."

She started to pump my ass hard. I actually started to enjoy it and started pushing back against her.

"See I knew you liked that bitch"

With a popping sound she pulled out of my ass and told me to lie on my back. I did as i was told and she lifted my legs above her shoulders and slid her cock back into my ass. She was really pumping my ass. I reached around and started to finger her ass. She quickened her pace and shortened her breath.

I dreaded what was going to happen, but I couldn't do anything. She had me pinned. With a loud groan she shot her load deep in my ass. I could feel it burning in my ass, but i couldn't stop myself I came all over her stomach.

"Too bad you came. I would have let you have a go but it will just have to wait until later my slave"

With a grin she got up and left for the shower.

To Be Continued.....?

The Predator walked over to one of the stalls and grabbed a handful of toilet paper from the dispenser and then strolled over to the ottoman.  He looked at the transvestite whore lying there, her lovely blonde bob and white nylon blouse were covered in the biker’s semen, her stockinged thighs spread wide crudely displaying her red nylon panties soaked in her own emission and that of the biker who had fucked her. With her leather mini bunched around her waist and her red high heels wide apart resting on the ottoman, she looked fucked and contented.  He handed her the bunched up toilet paper, “Clean yourself up,” he growled.

The Predator watched the transvestite as she sat up and adjusted her underwear; she stood up and moved over to the mirror and used the paper and some tap water to clean most of the semen off her hair and clothing; she went into one of stalls for a few minutes and then he heard a flush.  He was thinking to himself that he had very much underestimated this transvestite bitch; she had handled all of the circumstances that he had put her in to and was gaining the upper hand with each situation. A plan formulated in the back of his mind.  Would she go for it?  There was only one way to find out.

The Predator held his hand out to the dishevelled woman and when she took it he led her back to the ottoman and indicated for her to sit.  She sat down and he sat beside her and looked at her face; still pretty despite the messy makeup and unkempt hair.  He slid a hand over her stockinged thigh and looked her in the eyes, “Michele is it?  Well Michele, we are leaving here now and I’m taking you home. On the way we are going to have a chat and I’m going to make you an offer that I want you to consider; either way, given what has happened tonight I don’t think you want to go the authorities and tell them what happened; otherwise your friends and family would have to know about your double life.  Just think my proposition over let me know one way or the other.” 

The Predator kissed her gently on the lips and helped her to her feet; he handed her her purse and took her by the arm and escorted her out of the ladies room into the dark bar.  He walked Michele past the booth where Red still sat nursing a drink, “Bye Red,” he muttered as they walked past.  As they made their way to the door of the bar the bikers standing around the pool table all applauded and yelled out cat calls.  The Predator led her out into the cool night air and over to his car; he opened the door for her and as she went to get in the car he pulled her to him and kissed her.  She responded and wrapped her arms around him holding him tight.  He gently disengaged himself and helped her into the car and they drove away into the night.

Three weeks later……………………………..

The Predator looked at the middle aged woman spread eagled on the huge four poster bed.  She was tied hand and foot to the bed by the stockings he had taken from her dresser.  She was just to his taste; her heavily made up face was framed by her permed red hair.  He studied her for a minute.  Her pale skin was sprinkled with freckles just visible under the layers of foundation, face powder and rouge.  Her eyes were pale blue framed by her dark mascara and eyeliner and her bright red lipsticked lips quivered in fear.

The Predator cast his eyes along her body.  She wore a red satin evening gown; now slit open from her breasts to the hem at the bottom of the dress.  The gown had been pulled open exposing the black nylon full slip that she wore underneath; this garment too had been slit from top to hem exposing her red satin half-cup brassiere and matching directoire knickers.  Just above the waistband of her knickers the lace top of a black suspender belt was visible; the garter straps peeking out from the legs of her knickers were attached to high sheen taupe stockings; the stocking tops were dark brown and pulled taught where the suspenders were attached by their glistening silver clips.  Her shoes were red suede high heeled pumps.

The Predator thought she looked like a sacrifice on an alter; the bizarre image was like some gothic tale; with her red satin gown and black full slip spread open beside her; he imagined she looked like a vampire queen, spread eagled and awaiting the stake.

The Predator moved over to the side of the bed and gently, light as a feather, ran the point of the silver steel blade of his knife along her body; starting from between her breasts, along the curve of her belly and down to her sex.  As she moaned he savoured her fear.  The Predator placed his other hand over the crotch of her satin directoire knickers and pushed the silky material into her cleft, “Like I said, honey; don’t cry out and no one gets hurt,” he whispered.

Michele was dressed in a full-body black leather corset; her new breastforms filled the cups so that the leather pulled taught across her breasts.  She wore black satin full cut panties, the crotch just visible below the bottom of the corset.  Suspender straps ran from the corset underneath her panties and were attached to diaphanous black nylons with dark reinforced cuban heels and stocking-tops; tiny diamantes decorated the satiny stocking-tops and the cuban heels; a black seam ran up the back of the stockings.   These were the same stockings the Predator had made her wear to the biker bar three weeks ago; she knew he loved them.  Her feet were shod in black patent leather high heeled sandals; her painted red toenails just visible through the reinforced toes of her nylons.

Michele had carefully matched her makeup to her attire; which reflected her mood this evening.  Earlier in the evening she had sat in front of her makeup mirror and contemplated how she wanted to look.    The theme was dark; black actually, and she was so excited that she had to be extra careful when applying her makeup.  She applied two thick but even coats of pale foundation to her face and neck.  Then she painted jet black kohl to her upper and lower eyelids, starting in the very corner of her each eye, working outwards applying three thick coats so that her eyes looked like an Egyptian goddess.  She carefully brushed dark purple eyeshadow onto her eyelids applying several coats to get the desired effect; she smudged the dark makeup with a finger feathering it out and up so that it faded just below her eyebrows and extended right to the outer edges of her eyes.

Michele next applied a dusting of red rouge to her cheeks; running it diagonally across her cheek-line and feathering it up to almost meet with her eyeshadow.  She applied a coat of pale face powder next, setting the foundation and rouge.  Then she carefully removed the plump black false eyelashes from their little plastic container. She fiddled around until they were set perfectly and indistinguishable from her own upper eyelashes.  Her lashes were now long, plump and dark.  She heavily mascared her lower eyelashes and then reached for her lipstick.  She applied blood red lipstick to her lips using the base coat applicator and then set her lipstick with the clear top coat.  As she did this she was pleased to see her bright red nail polish matched the lipstick perfectly.

Michele applied another coat of pale face powder and reached for the wig she had selected earlier.  The wig was a jet-black short bob; she adjusted it in place and fiddled with the fringe so that it was in a perfectly straight line across her forehead coming down to just over her eyebrows.  She gave it a final combing; the sides of her hair extended along her cheeks and angled up; the hair at the back of the wig ran high across the back of her neck displaying her delicate white skin.  To emphasise her neck she clipped on a diamante set silver necklace which had three strings of diamantes drops connected to the main necklace hanging down to the top of her breasts.  She clipped on matching earrings which dropped almost to her shoulders.

Michele wore a huge red ruby ring set in silver on the ring finger of her right hand and a huge yellow diamond with matching setting on her left.  On all of her other fingers she wore silver rings of various designs.  Around her slim, black-nylon clad ankles she wore silver anklets.  She stood up and slinked over to her full-length mirror and looked at herself, her eyes wondering up and down, adjusting little things here and there. She uttered one word; “Perfect.”  Then she sprayed herself liberally with her favourite perfume, ‘Poison’, pulled on a trench coat and went down stairs to wait for the Predator who would soon be here to take her out on her first adventure with him.

Michele now stood on the other side of the huge four poster bed and looked down at her captive.  He was tied to the bed in the same fashion as his wife; lashed to the frame of the bed by nylon stockings.  He was wearing a black dinner suit but the jacket had been discarded before the man was restrained on the bed.  His crisp white formal shirt was unbuttoned; the tails untucked from his trousers and the shirt wide open displaying his dark hairy chest.  His black dress trousers had been pulled down to his ankles so that only his white satin boxer shorts covered his manhood.  He was about fifty but still trim and handsome; his deep blue eyes were set off by his black curly hair.  His face was chiselled and his cheeks well defined.

Michele ran a sharp red fingernail down his body, starting at his throat and ending just below his belly button where the waistband of his boxer shorts lay tight across his abdomen.  The man groaned; “You won’t get away with this you bitch!” Michele responded by gently fondling his package through the satin shorts and whispering, “Shush honey; you heard what my partner said; don’t cry out and no one gets hurt!”  She was pleased to feel the man was adequately endowed and could hardly wait for the fun to begin.  Her own genitals ware restrained by a gaff and as her excitement mounted it was becoming decidedly uncomfortable.

The Predator was naked; his rampant penis stuck out in front of him, tumescent, pink and swollen, a long rope of clear pre-seminal fluid hung from the eye of his glans.  He climbed onto the bed and straddled the woman who was lashed there spread eagled.  He rubbed his cock over her satin encased tits and groaned as the silky material stimulated the nerves in his hard member.  The woman squirmed beneath him but all her movements did was to excite him further.  He grasped the bed head and lifted himself up and forward until his cock was over the woman’s face and then lowered his crotch until his erect penis rested on her cheek.  He rubbed his cock all over her face and was delighted when a single tear escaped her eye and ran down her cheek.

Michele watched the Predator climb on the bed and knew that the fun was about to start.  She saw the look of anger in the eyes of the woman’s husband.  She sat on the bed beside the man and lowered her face to his and pressed her mouth down on his thick sensuous lips.  He tried to move his head away and she gripped his testicles through his shorts and squeezed.  He got the message and lay still; he knew there was nothing he could do.  The Predator had done all the talking when they had overpowered the couple as they had just finished dressing to go out for the evening.  The threats the Predator had made, particularly against the woman, had forced the couple to capitulate.  They knew their best option was to be compliant and then hope that the man and woman who had broken into their house would leave them unharmed once they had had their way with them.

Michele probed her tongue inside the man’s lips and forced it into his mouth; she swirled it around and savoured his sweet fresh breath.  She eased her grip on his testes and snaked her hand inside his shorts and took his thick flaccid member in her hand.  She kissed him harder and slowly started to stroke his penis.  She heard him gasp and then she felt his cock begin to harden in her fingers.  Michele smiled even as she continued to kiss him; she thought to herself that men were just so easy to control.

The Predator looked across at Michele kissing the helpless man on the bed and smiled when he saw her hand disappear inside his shorts.  He sniggered when he saw that she was goading an erection out of the man.  He moved his body down onto the woman so that he was lying on top of her, his face hovering over hers, “Look,” he said, “your husband can’t help himself; he’s enjoying it!”  The woman strained and turned her head and saw the attractive black clad woman kissing her husband; she looked down and was horrified to see the bitch had her hand inside her husband’s shorts and was stroking him.  She was more horrified when she saw the woman ease her husband’s erect member out of the fly of his shorts and stroke his hard cock, her bright red fingernails snaking up and down his tumescent member.

Michele was now stroking the hard cock in her left hand; she slid her fingers up and down the spongy mass of sinew and veins and felt it thicken and engorge.  She kissed the man passionately and he groaned and started to respond to her kisses, the tip of his tongue exploring hers.  Michele pressed her body against his and slid one sleek nyloned leg over his and began to rub her black nyloned leg up and down; he writhed and began to push up with his abdomen so that his cock was actually fucking her hands.  She loosened her fingers so that his cock was held in a feather like grasp; barely touching the skin of his penis.  She felt him buck and bounce as he tried to get more friction on his manhood.  Michele’s smile widened.

The Predator watched as the woman looked on horrified at the reaction of her husband to the ministrations of the whore who was rubbing her stockinged thigh along her husband’s leg.  She saw him attempting to fuck the trollop’s hand and heard his heavy breathing in between the long wet kisses.  More tears escaped her.  The Predator lowered his face to the woman and began to spray soft kisses on her pale skin; he gently lapped up her tears with his lips.  He ran his hand down her belly and tenderly cupped her sex through her directoire knickers and began to work the soft gossamer material of the knickers into her cleft.  The woman stiffened beneath him and then began to struggle. He forced his lips down on hers and pushed a finger into the folds of her labia and began to softly stroke her clitoris.

Michele looked across at the Predator as he began to stimulate the woman’s sex and force his mouth over hers.  She lifted her face away from the woman’s husband and whispered in his ear, “Look.”  The man turned his head to the side and was greeted by the sight of his wife struggling under the monster who had invaded their house.  To his disgust he saw his wife stop struggling and begin to move her hips in a circular motion in time with the man’s hand which was buried in his wife’s knickers.  While his attention was elsewhere Michele turned around on the bed and lowered her face the husband’s erect shaft and slurped the stiff member into her mouth, smoothing her lips all the way along the shaft until her lips were at the base of his cock; she lashed her tongue around the bulbous glans.  The man moaned and pushed his hips up off the bed and began to fuck her mouth as she moved up and down on his rampant cock.

The Predator looked across at Michele and saw her fellating the woman’s husband.  The man was face fucking Michele and he had look of extreme pleasure on his face.  The woman beneath him was now squirming and bucking as he manipulated her clitty through her knickers; he took his hand away and heard her mumble her disappointment into his mouth as he kissed her.  He didn’t disappoint her for long; he adjusted his position on top of her so that his hard cock was buried in the fissure of her open labia and began to dry fuck her through her satin knickers.  She bucked up against him and he moaned at the intense sensations shooting through his cock caused by the sleek material of her knickers rubbing against his erection.

Michele was sucking the husband’s cock in a steady rhythm, grasping the sinewy cock between her lips and whisking her tongue along and over his glans.  She could taste his secretions and his humping motion lifted his arse clear of the bed as he bucked under her.  She glanced across to see the Predator slide his cock between the wife’s legs and knew that soon this little drama would come to its climax.  Michele eased her face away for the man and this time she actually heard him grumble in disapproval.  She eased a hand inside her panties and untied the gaff so that her aching member could be free and then she lifted herself up over the man so that her stockinged thighs straddled his.  Michele raised her arse up and eased the gusset of her black nylon panties to one side and lowered herself slowly so that the tip of the man’s cock nestled up against her sphincter.  Michele lowered herself and gasped at exactly the same time as the man when his thick bulbous glans slid inside her.

The Predator saw Michele mount the husband and position his cock underneath her; he pushed the woman’s face to the right so she could see what her husband was doing.  The woman gasped, and as she did the Predator quickly repositioned his cock under leg of the woman’s directoire knickers and pushed his hard cock into her tight slick cunt.  The woman bucked and rolled beneath him and he hung on to her and enjoyed the ride.  He didn’t know if she was trying to buck him off or was trying to fuck him and he didn’t care; her firm vaginal walls were stretched around his rampant penis and all he could feel was the intense pleasure shooting out from his groin.  The woman beneath him began to set a measured tempo with her thrusts and it was obvious now that she was enjoying what she was getting; forced or not.  The Predator adjusted his position so that the base of his cock pushed against the woman’s clitoris and his balls rubbed against her gossamer smooth directoire knickers.  He started to fuck her hard and fast feeling his orgasm building.

Michele eased herself down further so that the man’s cock slid slowly further inside her.  She had lubricated her back passage in the bathroom before she had joined the Predator at the bedside and now she was glad she had.  The cock filled her anus and she had to take it easy and ride with the man beneath her to stop him lunging up and stabbing her arse with his cock.  She took control and eventually she was filled up with hot throbbing cock.  She sat down hard on the man to stop him from fucking her; she just sat there and enjoyed the feel of hot cock filling her arse.  Michele stated to gyrate as she clenched and unclenched her internal muscles to stimulate the cock buried inside her.  Then she started to slowly ease herself up and down on the rampant member, eventually loosening up enough so that she could increase the tempo.  The man beneath her sensed this and matched her with his thrusts; as she lowered herself down, he thrust up; the head of his cock pressed against her postrate and she felt her own orgasm build.  Michele bucked faster up and down on the cock and felt it slide in and out of her and stimulate the hundreds of nerves along the walls of her arse.  She was close to coming.

The Predator fucked the housewife with long hard strokes and lowered his face to hers and was greeted by sloppy wet kisses as the woman bucked beneath him.  Her cunt was spasming around his cock and he sensed she was about to come; he thrust faster and harder and was rewarded with her hot juices flowing around his hard cock.  He crushed his lips against hers and plunged his tongue into her mouth; he ground his groin against hers and she pushed back hard against him and her cunt convulsed as she orgasmed.  The Predator’s cock spasmed and twitched as it shot load after load of hot semen deep into the woman.  The housewife pushed back against him and shuddered as her orgasm racked her; she gasped around his tongue but continued to mash her lips against his, there tongues intertwined and teeth crashing together so intense was their climax.

Michele pushed down hard on the cock buried deep in her arse and felt it convulse.  The man’s member shuddered deep inside her and as it spasmed she felt jets of hot fluid fill her back passage.  His knob was pushed hard against her postrate and she felt her release.  Her issue shot from her semi-hard cock and filled the front of her panties.  Michele slammed her arse up and down on the rock hard cock that was spewing semen deep inside her.  She screamed and moaned and shook her head; the sensation was so exquisite.  Eventually her climax subsided and she came to rest straddling the man who lay there moaning beneath her, his cock pulsing in the last throes of his orgasm.  Michele lowered her head and gave the man a sloppy wet kiss and then leaned back and looked across at the Predator.

The Predator looked across at Michele as she raised herself from the hot wet kiss that she was giving the husband.  He saw her straighten up, the man’s cock still buried in her arse as she straddled him.  She smiled at him and leaned across; the Predator lifted himself from the housewife and Michele and the Predator kissed each other passionately across the bodies of their victims who lay lashed to their marital bed; the Predators cock was becoming flaccid inside the woman, and Michele’s back passage was contracting around the wilting cock buried inside her.  The wife looked across at her husband and whispered, “We can never tell anyone about this,” Her husband responded, “Never.”

Michele and the Predator smiled at each other.

The End

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

I flushed again.

Stacy had always been shy about her body. In all the years I had known her she had never been as adventurous with her style as I was. But that was going ot change. I was sure of that as I pictured my friend in a nice string bikini. My mind filled with the images of getting her home and pulling her out of it too.

I could feel myself blushing again.

‘So…’ Stacy said in a coy manner. ‘Where’s the best place to grab a cool costume.’

‘I know a place,’ I smiled my most devilish smile, knowing she was picking up the not so subtle hints I was throwing her way.

I scooped up my keys off the table, subconsciously counting each one as I did. Already I could feel the moisture building between my legs. I felt alive, exhilarated. Hoping my scent wasn’t evading my moistening panties. Just the thought of seeing my long time friend’s beautiful body excited me.

Right then I wondered if Stacy felt the same. Sadly, she just looked nervous, chewing on her bottom lip.

‘Come along then Stace. Let’s get going,’ I said, trying to keep thins light.

‘Right behind you Kelly, Stacy called back as she fetched her cute pink jacket from the coat rack. The one that hugged her breasts perfectly, showing them off for the world to see.

She quickly repositioned her skirt, nervously glancing at me, hoping I hadn’t noticed.

That was it! I thought she had just given me a sign of her mutual attraction. She was moistening too!

* * * *

Arm in glorious arm we made our way to my car. It wasn’t a flashy automobile, but it was reliable. And what more did a gal need than something reliable.

Stacy took her place in the passenger seat, while I slipped in behind the steering wheel. Clicking my seatbelt into its clip, I started the engine and we were off.

* * * *

I drove us to the store. From the outside it looked like a normal store. The promotional posters, while meant to look flashy had been bleached by the excessive sun, but they were still slightly attractive, as were the cute little outfits worn by the store dummies. But those were the outfits us normal girls could never wear.

From the outside Stacy seemed unimpressed. I took her arm again, and led her through the electronic doors. Her mouth fell open at the inner size. It looked like an elegant palace filled with the gowns of a million princesses. Stacy was dumbstruck with awe.

Lightly taking her hand, I led her down the steps into the main store. There were dresses, skirts, tops of all varieties, blouses, lingerie, daily wear. Stacy clearly had never seen so many choices grouped into one place. Or at least had never seen so many clothes that she wanted all at once.

I ignored the general clothes and led her to the back of the store, where the bathing suits were kept. And there were so many choices; bikini’s, cami sets, tankinis. So many options. So little time. I grabbed at a very skimpy black bikini set, almost no skin covered. Stacy was a little more conservative, going for a more common bra and brief set. I picked out a nice summer dress to wear over the bathing suit. A small flowing red number with all the tight curves. Stacy’s eyes lit up in admiration of my tastes for her. She pulled me out a short white dress. Very innocent looking. I held the dress against myself with the costume I chose underneath it. The thin white material gave away my choice perfectly. What a combo!

Now Stacy was taking the lead, guiding me roughly over to the dressing rooms. Obviously anxious to get me into my new outfit. I rushed ahead myself, just as anxious to see Stacy in hers, and maybe see her get into it too.

‘Want to share?’ I asked when our path ended by the dressing rooms.

The confirmation of Stacy’s attraction came when after a nervous moment she said yes and we clambered into the largest of the cubicles. Once the plastic door was shut, I felt Stacy’s lips lock themselves onto mine, her kiss reaching into my mouth. I wrapped my arms around Stacy’s back, pulling her beautiful body closer. Stacy’s subtle hands pulled at my top, lifting it carefully over my head, revealing my pink bra.

Stacy lowered her mouth to kiss my now erect nipples through the soft fabric. My inner moisture increased again, soaking my panties. I pushed myself closer, softly moaning my satisfaction.

I let my hand go to Stacy’s sexy mound, rubbing at her skirt. She pushed down onto my hand., her mouth kissing back up my breasts.

Everything I had wanted from Stacy lay beneath this skirt. No matter what I had to get it off, I wanted to se the hidden beauty of the girl I had waited three years to get. My hands went to her hips, slowly pushing at the elastic waistband, forcing the skirt down. She wriggled her hips, trying to stop me, she went for my hands. I kissed her harder, she let the skirt drop past her hips, revealing to me her secret. Stacy was a guy!

I jumped back. Completely surprised. I didn’t know how to react, my heartbeat was racing. And then I noticed what my body was doing. My moisture had jumped up a few notches, my pulse was racing, my breaths shallow and short. Oh my god, I was leaning back in to kiss her again. As I placed my lips back onto Stacy’s I pushed my skirt down over my hips and stepped out of it as it cascaded to the floor. I held my new lover in my arms.

My hands were soon cupping Stacy’s buttocks. My fingers tracing her crack, reaching for her perfectly puckered hole as her cock grew against me. She reached around and deftly unclipped my bra, slipping it down my arms and letting my petite breasts fall free. This was most unfair I thought. She had my breasts and I didn’t have hers. This was a situation that had to be sorted out.

While I focused her attention on kissing me, I worked my hands down her blouse, undoing each button, pulling the cotton garment open to reveal her sexy blue bra and its beautiful contents.

Stacy could stand no more. She was really rubbing her length against me, allowing the friction to pleasure her. Deciding I had to help I started to kiss my way down her super sexy body. I left her bra on, placing my kisses around the blue material, and carried on down past her stomach towards her bulging blue panties. I pulled them to the side, allowing her erect cock to fall into my ready hand. I placed another sensitive kiss to Stacy’s body before I slipped her twitching little friend into my anxiously waiting mouth.

The moment I wrapped my lips around Stacy’s warm cock I knew this was a first for her. The way she held herself was nervous, yet attentive, trying to memorise every action. I allowed more of her cock to slip into my mouth, taking all of it that I could, my tongue running around its outside. Stacy, driven at this point by sheer pleasure curled her fingers into my hair, gently tugging it as she pulled me further onto her. I had opened the cork on feelings she had never before expressed. Holding her balls in my hand, I feel Stacy suddenly tighten up, I knew what was coming and I sucked harder while I pulled her panties all the way to the ground.

Just I got the juicy goodness I wanted Stacy pulled her cock away from me. Gently, yet with great command, she pulled me to my feet.

‘Not yet, she whispered, kissing me again, pressing me back up against the dressing room wall. She ran her tongue over my nipples, taking one into her mouth, and kissing it with the same passion she had shown my lips.

Her hands led my panties down my legs while her kisses worked their way lower, across my abdomen, lower, past my waist, lower, over my trimmed blonde pubes to my glistening hole beneath. Nervously her tongue ran over my pussy lips. My thighs trembled at her careful touch, but I longed for so much more.

‘Don’t think so much,’ I told her. ‘Just go with the flow.’ I was going to wish I hadn’t said that.

Almost at once, Stacy’s nervous technique vanished. She had become a woman possessed. If I hadn’t have known otherwise, I’d have said she been licking pussy since the cradle. I had been waiting to get my friend here for three years, the only person to get my come in that time was me. I was saving it for Stacy exclusively.

Stacy switched between tonguing and fingering my pussy. God her technique was mind blowing. I couldn’t even find words to warn her what was coming. All my efforts were on keeping quiet, or just not getting to loud. Stacy got ferocious at my clit. She had obviously been wanting to get at my pussy as much I wanted her to. I moaned again softly, muffled by my fist crammed into my mouth, only just in time.

Before I had chance to let my hand down and pull Stacy further into me, she climbed back up to kiss me. I could taste my own salty juices on her lips, she offered it to me off her tongue. How could I refuse?

She leant in and kissed my neck. Her cock brushed against my pubes as she did. Her touch was electric. I wanted so badly to slip her into my pussy. But I held back.

Luckily for me, Stacy had the same idea. She bowed slightly, her hand pushed her cock forward, and lifted it into my pussy. She lifted my arms above my head, holding them in place, restricting my movement on my part. Once inside Stacy stopped. This I could tell was another first for her. I gave her a moment to enjoy the sensation, then, staring into her eyes, I clamped my pussy around her cock, and forced myself further onto her.

Driven by my desire, Stacy gave me a full thrust of her manly weapon. I gasped as her length filled my pussy, and pushed down to meet her. She gave me another thrust, and kept them coming. I couldn’t hold it anymore, my pleasure started to sound between my bated breaths, Stacy was the same. Neither of us were doing a very good job at staying discreet.

Someone knocked on the door. It was the store’s young clerk.

‘Are you ladies okay in there?’ she asked.

‘We’re fine, thanks!’ Stacy and I called out in unison, hoping the clerk hadn’t heard too much.

We didn’t move again until we heard her footsteps leading her away from us.

‘That was close,’ Stacy giggled.

‘I know,’ I giggled back as I felt my arousal spike suddenly. Almost getting caught was the ultimate turn on.

Stacy began to pick up speed again. Her energy doubled, and focused on bringing me to ecstasy. She got faster and faster until she reached a speed she could maintain comfortably. My cum was still flowing freely, running down Stacy’s cock and over her balls. She pushes harder and faster, using my cum as a lubricant to push in deeper.

With a slight groan muffled by my breast Stacy shot a hot load of sperm into my soaking pussy. Our juices merge inside me mixed by Stacy’s pumping and dripping back past my slippery entrance and running down our legs.

Continuing to push until the last of her own come was expelled, Stacy and I collapsed onto the floor of the dressing room. We had engorged ourselves on each others love and gotten quite messy in the process. All of a sudden I was glad I had packed a set of towels for our trip to the beach.

‘Here you go,’ I said as I offered one to her. She took it graciously, giving me a quick kiss in return.

A couple of minutes later, dried off and regaining our composure, Stacy and I got redressed. We gave each other another few gentle kisses. Her hands brushed my ass, squeezing gently while I cupped her lovely balls.

The attendant was coming back again, we heard her stilettos clacking against the floor, coming closer.

We hurried ourselves out of the dressing room, completely forgetting about the swimwear we had picked up. Left the store with a knowing smile on our lips and made straight for home.

We never did go back for that swim wear, but we had a lot of fun once we got home again.

"Yep, you are one fucking hot nurse alright; maybe next time you can play Nun!"

I heard his laughter fading as he walked down the passageway past the other cells to what I presumed to be the waiting room. The waiting room where undoubtedly there were more customers waiting. I closed my eyes as the tears ran slowly down my cheeks.

 

Part VI

I reached across and pressed the orange button to switch on the amber light indicating to Mabel that I was not yet ready for another visitor. I noticed the blue light was lit, indicating that I had another 'customer', or as Carmel would say "a punter" waiting.

I looked across and saw Carmel kissing the huge Negro who had previously been fiercely sodomising her. He pushed a handful of notes down her bra, spanked her playfully on the arse, and strolled out the cell. I quickly hid my face so that we would not make eye contact; I did not want him for a customer; not from what I saw of him when he was violently fucking Carmel.

I walked up to the cell bars and whispered to Carmel across the passageway, I could hear grunts and sighs as the other 'working girls' serviced their clients in the other four cells,

"Carmel, Carmel!"

"Hi Michele, see what Leon gave me?" She smiled pulling out a handful of notes from her bra;

"He is always a big tipper; and he has a big tip down there too!" she laughed at her own pun.

I had no time for this; I had important questions to ask. Carmel ignited the obligatory menthol cigarette.

"What do I do now; I pressed the orange button but the blue light is still on. Do I make the punter wait until I'm cleaned up or what?"

"Oh my God; Carmel, I want this to stop. I have just been sodomised so hard my back passage is bleeding!"

I started to sob again.

"Cut that shit out Michele; you need to harden-up girl or you won't survive!"

"Talk to Mabel on the intercom, sometimes the punters don't care too much how you look, especially if they just want a 'quickie'."

Again I was amazed at how quickly these perverts had degraded me down to their level. I was thinking of these crossdressed prison prostitutes as 'girls' and the men who raped me for money as 'punters'; plus I even understood what she meant by a 'quickie', it wasn't rocket science after all!"

I pressed the talk button,

"Mabel I'm not cleaned and dressed yet," I whispered in my best imitation of a feminine voice.

I hoped she would have some sympathy for me now that I was capitulating in this perverted parody of forced feminisation and prostitution.

"Don't bovver Michele; he's on his way. He just wants a quickie and this is a freebie so you better make it quick; time is money!"

What the fuck did she mean: 'Freebie'? I was about to find out.

The unmistakable navy blue uniform of a prison guard came into view. He was a fat man with a florid complexion, he was sweating heavily with the exertion of carrying around such a large gut.

I had sat back down on the bed and evened out my white nurse's uniform skirt, the semen and bloodstains were not too visible, but I knew they were there. My white pantyhose had laddered down one leg from the hole that my last customer had ripped in the gusset.

I did not recognise the fat guard but I knew he must be in charge of one of the other wings as he wore Sargent's stipes on his sleeve. He came straight into the cell, sweating and puffing, and without saying a word unzipped his fly.

I looked up in stunned amazement as he walked up to the bed, reached out a hand around the back of my head, and with his other hand, pushed his semi tumescent, uncircumcised penis into my mouth.

I started to gag immediately because the taste was so foul. It tasted of stale urine, and a cheesy taste that could only be the built up detritus of bodily secretions that had coagulated and fermented under his foreskin. It was the most disgusting taste I had ever tasted and my gagging increased.

The guard pulled his cock out of my mouth, pushed my head back and tilted it up to look at him; his fat face was snarling and vicious. He slapped me once across the face. He didn't say anything; he just wagged his finger in my face. The slap wasn't even that hard, it was just the surprise and his continued silence that stunned me.

He took his semi-hard cock into his hand again and pushed it against my lips. I knew enough by now to realise that my only salvation was to make him come as quickly as possible. I opened my mouth and pushed out my tongue. I deliberately licked at the lipstick on my lips to try and mask the fetid taste of the guard's penis. I then started to lick all around his knob that was half exposed out of the wrinkled foreskin.

I bought up my hand with the intention of masturbating the guard while I slobbered on his glans with my tongue and lips so he would ejaculate over my body rather than in my mouth. The guard would have nothing of it and slapped my hand away; he again grabbed my head and forced his cock between my lips and into my mouth.

He was still silent except for his heavy breathing and grunting. The smell of stale sweat wafted from his filthy body. He bought his other hand up now and cradled my head between both hands, the dirty fingers enmeshed in my hair behind my ears. Then he raped my mouth. There is no other way to describe it.

His penis became engorged and hard, the glans were now fully exposed as his foreskin pulled back from the bulbous knob. The foul taste of his cock was now so rancid I thought I might gag again so I did the best thing I could under the circumstances and worked up as much saliva as I could to wash his knob clean with my tongue. I worked up more spit and continued to slaver his cock with my tongue; this had the effect of cleaning his cock and cleaning out my mouth as I swallowed the foul mess that had coagulated under his foreskin.

These actions also obviously increased the guard's pleasure as he now increased his tempo, thrusting his erect member in and out of my mouth. He pulled his cockhead out as far as my lips and then rammed it home as far as it would go. Luckily his cock was not very big and I had no problems accommodating him, it was just so hard to breathe with it jack-hammering in and out of my mouth.

On the in-stroke he pulled my head forward to that my nose was buried in his fat gut overhanging his loins. He forced my head onto his penis so hard that my teeth rattled on the metal zipper of his fly. He was sweating so much that I could feel drops of his disgusting perspiration dripping off his jowls and on to my head.

He continued to grunt like a pig as he fucked my face; his now rock hard cock with its spongy head tasted salty as precum started to leak from the eye of his glans. He pushed it in and out faster and harder, pulling it out nearly all the way then slamming it home so that my face was buried in his crotch.

Then he pushed my face into his crotch as hard as he could and held it there. I couldn't breath! I felt my gag reflex returning as I struggled to get oxygen into my mouth or nose. I reached out and tried to push myself back from him but his vice-like grip was too strong; he pushed my face harder into his crotch.

I couldn't help it, I stated to gag, my mouth convulsing and my tongue flailing around in my mouth. At the same time my fists were drumming against his thighs as I tried to push myself away. That was when he stated laugh! He also said the only word he ever spoke,

"Good!"

He held my face hard against him and as I started to blackout I felt his penis convulse in my mouth. Stream after stream of creamy, salty, hot semen shot into the back of my mouth. As the guard's cock continued to eject its foul jets of spunk he continued to laugh. He was laughing as he orgasmed.

At last he released the tight grip on my head and allowed me to take a breath through my nose. As soon as I did he pushed my face back into his crotch. As my mouth filled up with his sickly seed I had no choice but to swallow. If I didn't I would choke. His ejaculation seemed to go on forever and try as I might I could not swallow all his come. It welled up in the back of my throat as his cock continued to throb and convulse. I coughed and felt his slimy emissions force its way up the back of my throat and then run out of my nostrils. I felt disgusted.

Then the guard pushed me away. I fell on the bed gagging, sobbing and coughing; trying to breathe. He reached down and grabbed my hair and pulled my face up again so I was looking at him from level with his waist. His face was bright red, florid and sweaty. His jowls dripped sweat down his shirt. Without a word he rubbed his now deflating penis all over my face mixing his semen with my tears and my makeup. Then he put his cock inside his pants, zipped up and walked away. I had never felt so humiliated in my life.

 

I lay on the bed sobbing. I looked up through the tears, makeup and semen in my eyes and noticed that the blue light on the intercom was mercifully extinguished. I reached out slapped the switch to turn on the orange busy light. The intercom suddenly crackled and I heard Mabel, the crossdressed old con who was our 'madam'.

"Take half an hour hun, it's gone quiet for now and it's getting late; get cleaned up and give me a call."

I half groaned into the intercom,

"Sure."

I wanted to just lay on the cot and cry myself to sleep but I knew that Carmel was right, I had to harden up if I was to survive. I had to find out as much as I could about this sick operation so that I could tell someone in authority so they would get me out of this nightmare.

I stood and stripped off my stained nurse's uniform, slid out of my high heels and pulled down the tattered pantyhose. I threw the hose in the bin, stripped off my remaining underwear and placed it with the uniform in the washing basket that was tucked away in the corner. I noticed the little ridiculous nurses cap on the floor and picked that up on the way. I pulled off my wig and put on the satin robe. All of these movements caused me significant pain. My head ached from the slapping I had received, my back passage felt like someone had put a red hot poker up there, and I was now immensely tired. I had no watch but guessed it was after 3:00am.

I padded out of my cell with my makeup case in hand and made my way down the dim passageway. I deliberately tried not to look in the other darkened cells but in the subdued red lighting I could see Carmel was kneeling on her cell floor and fellating a con who was sitting on her bed. His head was propped back on a mountain of fluffy pillows, his eyes closed as he enjoyed her ministrations.

As I passed the end cell on the right I heard muffled yelps and couldn't help but peek. I saw a fat crossdressed 'working girl' dressed in a French maid's outfit, baby-doll blonde wig and heavy makeup; a skinny little con was riding her doggy style on the bed. He had her black satin maid's skirt rucked up over her back and her black satin panties hung from one fat, black-stockinged ankle as he humped her and smacked her plump white ass as he did. She yelped every time he smacked her, but she seemed to be smiling and pushing back to meet his thrusts. If my life weren't so tragic I would have found the sight immensely funny I suppose.

I continued on to the shower-block and let the scalding hot water wash away my makeup, tears, and the semen from two different men. I was so close to crying again but held back. I heard the shower next door suddenly splash into life.

"Hello?" I asked with a trembling voice.

"Hi hun," I heard the response as a male falsetto.

"I'm Charlotte. No Charlotte the Harlot jokes please!" she laughed.

"Welcome to E Block Michele," came the voice over the shower cubicle.

"You know who I am then?" I asked.

"Oh of course hun, it's always the talk of the nick when a new girl starts working for Eddie."

I turned off the water and towelled myself dry thinking about what Charlotte had said: 'talk of the nick'?

Charlotte emerged from the shower with a huge silk bathrobe wrapped around her generous proportions. She was the French maid I had seen on my way out of the cellblock. She made her way over to the line of stainless steel mirrors and began to apply makeup to her plump but pretty face.

"What do you mean by 'talk of the nick'?" I asked taking a seat beside her and applying foundation to my face.

"Well Carmel should have told you everything; didn't she?"

I went on to explain to Charlotte what Carmel had told me and also what I had figured out for myself. I made no mention of my plan to escape this hellhole; Charlotte like Carmel seemed to accept the situation and even seemed to like what was happening to her.

"Well you seem to have it figured out pretty well hun. Eddie owns us girls, Steve is the muscle, Mabel is the Madame; and up until yesterday darling, you used to be the accountant and secretary."

"I suppose you still are Eddie's secretary," she said sarcastically.

"Lots of us girls started out working for Eddie in other roles; as runners, dealers, or small time worker bees. Eddie seems to have the knack of knowing which cons will look like sexy women when they're crossdressed; feminised if you will."

"Some of the prospects are so obvious because they are 'femme' when they arrive in the nick; some convert to homosexuality as part of prison life and Eddie feminises them as willing subjects, and some like you are forced into it."

"To be honest I think Eddie likes it better when he has to force them," she smiled, smoothing on a second coat of bright red lipstick.

"How many of us are there? Crossdressed prostitutes I mean?" I asked incredulous.

"Oh not that many; about a dozen or so at any one time, but only six of us work in the workrooms."

"Some take up full time with cons who can afford to pay Eddie enough to keep them; some are just let go when Eddie has made enough from them or they break down and are sent to the psycho ward."

"Take Carmel for instance, she still works for Eddie even though she has a prison 'husband', she does it because she likes the money, she likes the gifts from Eddie, but mostly she likes the life."

"Then there is Mabel who did this for so long that she got too old to work the cells so she's Eddie's hostess, Madame, whatever; but will still give a con great time if doesn't mind mutton instead of lamb if you know what I mean?" Charlotte winked and concentrated on applying another thick coat of mascara.

"But what about the Warden? I know lots of the guards are corrupt from my time here already, but how the fuck does Eddie get to run a stable of crossdressed prostitutes out of a prison wing? I know it's this is a small disused block, but fuck me its prison property!!!!"

"Oh my god Michele for some one who is so smart you are so dumb!"

"Who the fuck do you think is Eddie's partner? It’s the Governor you fucking idiot!"

I let that settle in. So it was going to be no use going to the prison authorities with my complaints; I would just have to figure a way to use my money and outside influence to go higher up the chain of authority to rescue me.

I looked at myself in the mirror; it amazed me how quickly I had got the hang of applying makeup. I had on thick coat of foundation and powder, rouged cheeks, heavily lined and mascaraed eyes, mauve over pink eye shadow, and my dark ruby red lips. I sure knew how to look like a slut after only one night!

Charlotte's makeup was even heavier than mine, and her plump bright red lips and chubby face, gave her a slutty girly look. She picked up her makeup case and stood to leave,

"Did Carmel tell you not to leave anything in here? Those other bitches will steal your knickers while you're still wearing them if they can get away with it!" she laughed.

I fell into step beside her,

"But what did you mean by me being 'talk of the nick'" I asked again.

"Oh whenever a new girl starts the punters are always interested. Eddie can charge them more because you are new, undamaged goods, but of course he has throw the senior guards a few 'freebies' to keep them on side."

"He will probably limit the amount of punters you see for the first few nights, but after that you will be the most popular girl at the ball!" she laughed.

"You like this don't you; this life?" I asked trying to keep the disgust out my voice.

"Oh Michele, I didn't like it at first, but now I love it! I work all night and sleep all day and Eddie gives me anything I want!"

"I hated it so much when I first started that I though if I got fat none of the punters would want me. I was already a bit plump so I put on another 10 kilos; guess what? Some of the punters just love us larger girls!" she giggled.

"After six months of hating myself I started to realise I liked it. I bet you have already had a few twinges in the clitty whilst those naughty men have had their way with you?" she chuckled.

"See ya," she whispered as we came adjacent to her workroom cell and slipped though the door.

I though to myself: 'How can she know? Twinges! Twinges!! I have had an orgasm for god's sake!!!' My god I hope I never get to like this wretched existence like the other wretched girls!

I entered my cell and sat on the bed. It appeared none of the other girls had punters either for now as they were either adjusting their makeup in their wardrobe mirrors or changing into robes to go to the shower and bath block. Through the bars I saw Carmel lounging on her large work cot surrounded by her mountain of satin pillows; she had the obligatory menthol cigarette and was reading a fashion magazine by the dim red light of her lamp.

To my disappointment it looked like this night's training had paid off; I knew exactly what to do next! I had been brainwashed to some extent. Without further thought I selected a brunette shoulder length wig and adjusted it in place. I opened the drawer and took out a set of matching white satin full cut panties, bra, and garter belt. I put the bra in place and tucked the breastforms into the cups. I selected a pair of diaphanous skin toned stockings that were embellished by black seams and black, reinforced heel and toes. I slipped into the garter belt, sat on the bed and slid the exquisite cool nylons onto my legs, fastening them to the garter clips. I smoothed each stocking out along my legs and adjusted the seams so they lay in the centre of the back of my legs.

I sat there stroking my legs, feeling the luxury of the expensive nylons sending little electric waves of pleasure though my body. I don't know how long I had been caressing my nyloned legs when I snapped out of the reverie.

"I will not surrender to this perversion!" I told myself.

I slipped the sleek white nylon panties up my legs and stood to adjust them in place, the little electric shocks from the swish of the nylon on nylon as they slid up my legs caused my penis to spasm involuntarily. I concentrated and pushed my wrinkled penis into the snug silken gusset of the full cut panties.

I walked to the robe and selected a white leather miniskirt and peach satin blouse. The satin of the blouse on my bare skin was again cool and luxurious; I had trouble with the buttons because they were on the wrong side. I sat on the bed again and put on the strappy white high-heeled open toe sandals that I had selected. The reinforced heels and toes of my nylons made a sexy display. I stood up and stepped into the white leather mini and hitched it up, tucking the blouse into the waistband and zipping the skirt at the side.

I went to my jewellery box and selected a small plain gold bracelet, which I fastened around my ankle. It glowed in the dim light, set off by the contrast of my silky flesh toned stockings, reinforced nylon stocking heels and the white leather ankle straps of my high heels.

I selected a simple gold chain for my neck and plain gold drop earrings. I slipped two gold and emerald rings onto my fingers. I noted my ruby red fingernail nail polish was chipped, but in this light who cared. I wondered how much, if any, of this jewellery was real.

I looked at myself in the full-length mirror. I saw a mature, sexy woman with brunette shoulder-length hair, wearing heavy makeup and a lovely peach satin blouse. Her jewellery was exquisite, the emerald rings on her finger contrasting with her red polished fingernails, the simple gold neck chain resting where the hint of her breasts began to rise in the satin blouse.

Her tight white leather skirt stretched across her tiny little pot belly and clung to her well formed thighs, the hem resting against her sheer nyloned thighs, displaying just a hint of dark nylon stocking tops. Following her well-formed legs down, they are encased in gossamer thin, flesh toned, nylon stockings with sexy black back-seams. The black reinforced heels and toes of her stockings peeked through the high-heeled sandals, a glimpse of red nail-polished toes just visible through the nylon. The strappy white high heel sandals pushed her feet up at the heels so that her toned calves glittered in their nylon casing, the gold anklet smoulders in the red light.

I reach out and apply a coat of powder to my lower neck and decolletage where it disappears into the satin blouse. The final touch. I look gorgeous, sophisticated but highly desirable. I look eminently fuckable!!!

I turn around and Carmel and Charlotte are in the corridor leaning on the bars of my cell and looking in; cigarette smoke drifts past Carmel's heavily made-up face and creates a halo around the jet-black hair she is wearing teased high on her head and descending past her shoulders. Her heavy Goth makeup, red lips and pale skin make her look like the caricature of a vampire in the movies. This image is reinforced by the skin-tight, black satin sleeveless dress that clings to her body and descends to her ankles. The dress is split up to the waist and one leg encased in sheer black nylon is on display to up to her thigh.

'Sheer to the waist pantyhose,' I thought to myself, then: 'Stop thinking like that; you are not a woman!'

Carmel's outfit is completed with black, satin, opera length gloves, patent leather spiked high heels and a profuseness of silver jewellery. She has a huge silver cross around her neck, long silver ear drops and silver bangles on both wrists.

Charlotte has gone punk and even though she is a big girl she carries it off somehow. The heavy makeup she applied in the shower block has been enhanced even further with more black eyeliner surrounding both of her bright blue eyes. She has extended the dark pink blush from her cheeks to the corner of her eyes and added a powder blue blush to it as a contrast. Her bright red full lips have been glossed and she has added glitter to the abundant multi-coloured eyeshadow that extends from her eyelids up to her eyebrows. Her plump pretty face is framed in a shocking, frizzy, bottle blonde wig that has pink and blue streaks running though it.

She wears a black sequined top that is slashed and torn, her red lacy bra visible in some places through the tears. Written across the front of the ripped garment in silver sequins are the words: "Fuck Slut". She is wearing a red Lycra mini that barely covers her crotch; the waistband bulges around her big belly. She is wearing ripped black fishnet stockings attached to red garters that match her bra. The fishnet stockings stop halfway up her fat thighs and I can see she is wearing shiny taupe dance tights underneath as a foundation garment; the heavy lycra shimmering in the dim red light. Her feet are clad in the tallest high-heeled pumps that I have ever seen; the heels have to be ten inches high. Charlotte has finished the outfit with outrageous jewellery. She has four gold studs in each earlobe, so many gold chains around her neck that I can't count them, and as many bangles on both wrists. Ornate safety pins decorate her torn blouse and micro mini. A gold chain runs from one earring to a gold stud in her nose.

"You look gorgeous Michele," Carmel whispers through the bars.

I wondered if she had read my mind when I was standing in front of the mirror admiring myself.

"Well, I have to say you girls are looking something special. Special fetish requests from the punters?" I enquired.

"Well no Michele; there are no more punters tonight; we're closed for business." Carmel responded lighting yet another menthol cigarette and blowing a cloud of blue smoke towards me.

"Thank fuck for that," I breathed with a sigh of relief.

"Now I can get out of these stupid fucking women's clothes and get back to my own cell!" I said, relived that the evening had come to an end.

Carmel and Charlotte stepped into my workroom cell, silently closed the door, and leaned back menacingly against the bars,

"Oh no Michele, you don't understand! We've finished with punters tonight, but WE haven't finished with you!!!"

 

To be continued……………………………………………….

“What did you think?” Amy asked.

 

“Well, let’s see…” I started to answer, “You gave me the best blowjob I’ve ever gotten, sucking your dick was about the best thing ever, and sharing your cum with you was incredible…all in all, I’d say it went well.” Amy smiled and walked over to sit with me on the couch. We sat quietly drinking our Gatorade for a few seconds until I decided to say something, “Ames, when you came, I swallowed probably a third of it, quite a bit dripped from my mouth, then a lot spilled on your boobs, and there was still so much…do you always cum that much?”

 

“Not always, but most of the time it’s pretty close to that. You did a really good job sucking me off though, that definitely helped. I didn’t think there would be that much ‘cause I jacked off before you picked me up tonight. I’ve had to do that a lot lately…I’ve been really excited about tonight.”

 

“Do you always swallow your own cum? ‘Cause, if you do, I gotta say, I’m impressed. You must really like it.” Amy just smiled as some blush showed on her cheeks.

 

“What about you? Did you like it?”

 

I thought for a second and responded, “Well, it wasn’t bad. I mean, it didn’t taste great, but it felt great. Feeling your warm cum going down my throat was awesome.” Just then sounds started coming down from upstairs. It surprised me at first, until I remembered that Karissa and Brian had hurried to her room when they got there. I could hear Karissa moaning. “They must be having fun.”

 

Amy had started laughing mildly when Karissa’s whimpers of pleasure reached the living room. “She does enjoy getting pounded. I’ve never known anybody who likes it as hard as she does.” This brought a thought to my mind.

 

“So, she doesn’t have, I mean, she isn’t like you?” I asked.

 

“No, she’s a normal girl. And she’s got a really small, tight pussy.”

 

After a short pause, I asked, “So do you two ever…?”

 

“Not as much as we would like,” Amy answered before I finished asking, “We do it probably once a week. Our mom is home a lot. When we used to share a room we would do it almost every day, but when Nathan left for college and I took his room that kinda stopped. Now I sleep downstairs, and it’s just too hard for either of us to sneak into the other’s room without waking up our parents. Whenever mom and dad go out we can really go at it, but other than that we have to just fool around a little bit here and there during the day. Karissa loves anal though, I usually butt-fuck her when our parents are out. That butt-plug you’re holding is hers.”

 

I had been looking through the paper bag that Amy had thrown me earlier. “Wow,” I said, “This has actually been in her ass? All the times I fantasized about her ass, and now I’m holding her butt-plug.”

 

Amy suppressed a small giggle and said, “Yeah, I bought it for her for her birthday last year. We both use it, but I only can when she isn’t, which isn’t as often as I’d like, she loves that thing,” Amy laughed a little bit as she said this. “When she gets home from track practice, she usually puts it in and keeps it there till dinner. Sometimes she even sleeps with it in!” I was amazed at this, I had no idea anybody could like having something in their ass that much. Just then Karissa let out a loud moan followed by several repetitions of “oh my God.” I knew she was cumming. I drifted off into a daydream about her. Karissa was the cutest sophomore at our school, she had blonde hair that went just past her shoulders, brown eyes, a really white smile (just like her sister), and since she ran track, her body was pretty thin. Her legs were muscular, and her ass firm. She had small boobs, I’m not sure what size, but I’d venture a guess that they were mid-A cups. Karissa always wore tight jeans and colorful, loose tops, which was a good wardrobe choice since it accentuated her great lower body and made her small breasts appear larger. She had started at the high school her freshman year because she wanted to get the “high school experience”. That year, when I was a sophomore, she was a football cheerleader, she distracted me every game, which I didn’t mind too much since I hardly ever played anyway.

 

As I was thinking about Karissa’s body and imagining what she would look like under her clothes Amy spoke up, “You know, I’m sure that if I was given a few minutes I could convince Karissa to join us.” Just as I was about to tell her how much I would love that, Brian let out a loud groan, he had obviously climaxed as well. “Okay, if you want her to, you’ll have to give me some time to talk to her. She never lets guys stay for very long after they finish, so you go and take a shower in my bathroom, and I’ll go upstairs and talk to her and make sure Brian leaves. Make sure you’re in there for at least 20 minutes ‘kay?” I was going to say ‘alright’ but before I could she hopped up and headed toward the staircase. Amy looked back and said, “Hurry up,” then quickly went upstairs. As she went I watched her tits and cock bounce. When she was out of sight I leapt to my feet and hurried to her shower.

 

As I was showering I made sure to clean my dick and ensured that my sphincter was clean. Tonight I could have Karissa’s butt-plug or even Amy’s dick in it, and I wanted to be ready. I periodically poked my head out from behind the shower curtain to glance at the clock. After 20 minutes had passed I got out and dried off quickly. I put the towel around my waist and stepped from the bathroom. I walked through Amy’s room and into the living room. I expected to see Amy and Karissa fucking on the floor, but to my surprise, I saw only Amy, sitting alone on the couch watching TV. I looked out the window and saw Brian’s car was still there. “Oh well,” I thought to myself, “Hell, I got Amy, I guess wanting Karissa too was selfish. I can still fuck Ames, and maybe she will fuck me too…” I had desperately wanted to fuck Karissa though. I sat behind her in U.S. History, and I fantasized about her almost daily. I had had a crush on her for years after I met her. From 7^th to 10^th grade she was all I thought about, but I had never been able to get close to her. “And here, tonight,” I thought to myself, “I was foolish enough to think I might get to fuck her…”

 

I walked up behind the couch where Amy sat, naked. I stood behind her and looked down at her body. Her boobs showed remnants of where her cum had landed, and where I had licked it off. Her nipples were perky, and her dick was semi hard. Just as I was about to tell her that not getting Karissa to join was alright and that all I needed was her, I heard somebody in the kitchen. I looked to my left and stopped in my tracks. Karissa walked into the living room completely nude with a bottle of water in each hand. Her breasts may have been small, but they were round and perky. The nipples were small and pink. Her stomach was firm and she was tan all over. When my eyes finally came to rest on her pussy, my mouth dropped open. It was shaved clean except for a small rectangle of very light brown hair on her crotch above the pussy. Karissa walked over to the couch, handed Amy a bottle of water, then turned to me and asked if I wanted one. “Sure,” I said. She turned to go back to the kitchen and when I looked to watch her ass as she walked I saw the square base of her purple butt-plug sticking out. My eyes widened at this as Amy reached over the back of the couch and wrapped her fingers around my now hard cock.

 

“I thought you’d like her. Wait till you’re in her pussy…it’s amazing,” Amy said as she looked into my eyes. I went around the couch and sat next to Amy. I laid my hand across her lap and started squeezing her cock. “I think you should put this on,” Amy said as she held up a condom, “I don’t know how long Karissa is gonna wanna wait.” Amy then opened the condom package and started rolling it down my dick.

 

“What about Brian? Is he in the kitchen?” I asked.

 

Amy smiled and replied, “No, he was pretty drunk so Karissa called Kyle to come get him. You have us all to yourself.”

 

Karissa walked in with another bottle of water and handed it to me. She stood in front of the couch between where Amy and I were sitting and said, “Well, well, well…” she bent down, grabbed my cock head with her thumb and forefinger, and went on, “A bit presumptuous, don’tcha think?” I smiled nervously and looked to Amy, who just smiled wickedly at me. Karissa continued, “I’m gonna jump in the upstairs shower for a few minutes, you two have fun.” She turned around and bent over slightly and asked in a really seductive voice, “Matt, will you get that for me?” I reached out, grabbed the base of the purple butt-plug, and started pulling it out. However, Karissa tightened her rectal muscles, and as I started pulling harder she opened her mouth and moaned slightly. When it finally popped out she let a sexy whimper leave her mouth. Karissa stood back up and as she started walking up the stairs she looked back and said, “It’s a good thing you got it out, you’ll need it more than I will.” She then winked at Amy and disappeared down the hallway.

 

It was then that I felt Amy pulling the butt-plug away from me. I looked over in time to see her start rubbing KY Warming Liquid on it. “Roll on your side,” Amy whispered sweetly with a smirk on her face. I hesitated and she continued to say matter-of-factly, “Well come on, your ass isn’t going to loosen itself up.” I leaned to my right, away from Amy and when I was on my side, I felt her fingers massaging my ass with the KY. When she removed them at first I was disappointed, but when I felt the butt-plug start to poke into me, I was nervous. I was just about to ask Amy to wait when she pushed it in seemingly as hard as she could. I groaned in pain as it stretched me. She started pulling it out and then rammed it back in, she did this again, and again, fucking me with it. After probably 30 seconds she forced it in and left it there, telling me to sit up. I did and as I did I could feel my weight pushing it in farther. I closed my eyes and Amy’s hand began rubbing my dick. I looked down and she was lubing it up with the KY. She then stood up, and still facing away from me, maneuvered herself over me. She lowered her body until she was almost on my lap. Amy reached down and adjusted my dick so that it was at the entrance of her amazing ass. Then she lowered herself onto it slowly, but before all of it was in she rose back up just as slow as she had come down. After repeating this several times, Amy suddenly slammed her ass down into my lap and my cock was thrust into her. She rapidly began riding me. Every time Amy’s ass hit my lap it forced me lower which, in turn, forced the butt-plug farther into my ass. Both sides felt great, and I knew that it was just a matter of time before I blew my load. I reached my hand around and grabbed Amy’s rapidly bouncing 8 inch cock and started pumping her as quickly as I could, although as fast as she was moving it was difficult to maintain a normal “jacking” motion. “Aww yeah…jack me off…” Amy commanded, “And tell me before you start to cum…”

 

After a couple minutes of Amy slamming her ass down, (virtually impaling herself on my dick), having the butt-plug driven into my ass, and feeling Amy’s nice big dick in my hand I knew I was going to cream in the condom so I let the words escape, “Ames, I’m gonna shoot…” As soon as I said this Amy leapt from my lap.

 

I expected her to drop to her knees and begin sucking for her life, but she just turned around and said, “Not yet…has our purple friend got you ready?” I felt a little cheated, but I didn’t want to upset the girl who was making my dreams come true so I simply nodded. “Good, it’s my turn then…get on all fours on the floor.” I did as she said and not a second later she was on her knees behind me. Amy pulled the butt-plug from my ass and rammed it into her own as she whined with what sounded like pleasure mixed with relief. She wasted no more time as she reached back and pulled a condom from the paper bag. Immediately, the extra-large rubber was opened and on her sweet meat. Amy started rubbing her cock-head against my anus, and after a while I just wanted it inside me. Finally Amy took hold of my hips and forced her big member in my body. There was no slow stuff like when she first started riding me, I was being straight up fucked in the ass by the hottest girl in school…and I was loving it.

 

Karissa came slowly down the stairs and walked up to where I was getting hammered. “I think I’ll just lay down here.” She laid on the floor with her pussy right under my face, looked at me, and said “Do it, you know you want to.” Did I  ever! I dove forward licking and sucking everything I could get to. I buried my tongue deep in her pussy and licked like there was no tomorrow. I pulled my head away and took her left pussy lip in my mouth and sucked on it desperately. I then moved to the right and did the same. After I had had enough of her delicious lips, I pulled my head back, looked her straight in the eyes, and looked at her as if I was asking permission. “Yes, do it! Suck my clit!” she begged me. Who was I to deny such a sweet and innocent girl such a simple wish. I popped the small pink bud in between my lips and started sucking on it like a pacifier. “Fuck him Amy…pound him good…” Karissa moaned roughly.

 

Amy’s cock was sliding in and out of my ass and I was going wild on Karissa’s pussy. My dick was throbbing, so I took my left arm, keeping my right steady for balance, and started jacking myself off. Karissa was moaning desperately now, I knew she was getting close so I kicked my mouth into overdrive. Licking up and down her pussy frequently stopping to suck on her clit. The pussy in my mouth started convulsing and Karissa’s juices started flowing freely. I kept sucking her clit until she cried out, “Oh God…stop, stop, stop…I can’t take it anymore…” as she pushed my head away from her sweet spot. She laid their spent for a couple minutes as Amy fucked me relentlessly. Karissa slowly rolled over and crawled up to me face-to-face and grabbed my hair. She then pulled my head closer to her and started kissing me deeply. Karissa’s tongue darted around my mouth as she kissed me and Amy’s cock slid smoothly as she fucked my ass.

 

All of a sudden Amy pulled her dick out of my ass, stood up, and walked over to where I was kissing her sister. Karissa rolled the condom off her sister’s cock and grabbed its base. Amy said, “Deep throat it.” Karissa wasted no time, she plunged her head forward; instantly the 8 inch cock disappeared. My jaw dropped in amazement as she pulled her head back and thrust it forward once more. As Karissa deep throated the cock in front of her I leaned in and began licking Amy’s balls. As I was taking one at a time into my mouth and gently sucking on it Karissa was working her sister’s member like an expert.

 

Karissa pulled her head back to catch her breath and Amy’s dick bounced freely. I took this opportunity to slide the nice warm rod into my own mouth, and began sucking with vigor. I looked up to see Amy starring at me smiling. I pulled my head back so just Amy’s cock-head was in my mouth. I sucked on it hard before popping it out of my mouth, then sucking it back in. I repeated this several times and Amy’s smile widened as she started giggling. “You actually enjoy sucking me don’t you? I didn’t think any guy would ever wanna give me head,” she said laughingly.

 

I popped Amy’s cock-head out of my mouth once more and replied, “Well, what can I say? I just can’t control myself, you’ve got one delicious cock here Ames. I’ve been into shemale porn for a while, and I’ve imagined sucking a girls dick before…but I never thought it would be this fun.”

 

“I am so glad I found you…” Amy said, “You know, Jaymes only sucked my dick once, and I had to get him really drunk. He never let me fuck him either.”

 

I was a little surprised at this. Jaymes had been Amy’s boyfriend before he gone away to college that fall. I asked, “How did you get off then? I mean, if he never sucked you, and didn’t let you fuck him, did you guys have sex very much?”

 

“Well,” as Amy began speaking I felt breath on my cock and realized Karissa had gotten bored with the conversation and decided to busy herself. I felt Karissa bring my dick into her warm mouth as Amy continued. “We did fool around a lot, usually he would have me suck his dick for a while, then he fucked my ass until he was almost ready to cum, then I would finish him. Sometimes after he came, he would give me a handjob, but most of the time he would kiss me or play with my boobs while I jacked off. He always made sure he got off first though. Except for once, he had me jack off and cum in a glass. Then while he was fucking me he poured my cum all over my boobs and had me give myself a cum-covered tit massage.” She paused and then addressed her sister, “Karissa, when he cums don’t swallow all of it, save me some.” She responded with a muffled “mmm-hmm” before Amy went on, “Anyway, enough about him…I’m just happy I found a guy who not only sucks me off, but swallows my cum!”

 

Amy continued to giggle as I tossed my head back and enjoyed the sensation of my cock in Karissa’s mouth. “She’s good isn’t she?” I opened my mouth to answer Amy’s question but before I could she continued, “Wait Karissa, I’ve gotta better idea. You’ve got to let him fuck you…her pussy is so tight, it’s unbelievable.” Karissa let my dick slip from her mouth and rose to her feet. She walked over to the couch and laid down with her legs spread. I hurried over and got between those muscular tan legs, reached down, grabbed her ass, and lifted her pelvis up off the couch cushion, level with my cock. Amy was standing beside the couch and spread Karissa's pussy lips for me. I pressed the head of my member up against Karissa's opening, it was so wet and so hot I almost felt like I could blow my load then. I pushed forward with my pelvis and I began entering her. Amy was right, I had never felt a pussy so tight before. I pushed until I was about 1/3 of the way in, then I withdrew a bit and pushed back in, deeper this time. I continued like this until my cock was inserted to the hilt every time I went in. At this point I began thrusting harder and faster. As I increased my speed and force Karissa started to get more into it. “Pound her, just pound the slut. I want you to fuck my little sister harder,” Amy had long since removed her hands from Karissa’s pussy and was providing verbal encouragement.

 

Amy stepped up onto the couch with a leg on either side of her sister facing me. She inched closer to me, her cock bobbing in front of me was too enticing to pass up. I stretched my neck out so my extended tongue could reach her wonderful dick. I licked Amy’s cock-head while I fucked Karissa. Amy moved closer, I was then able to start sucking her properly. I closed my eyes and enjoyed the sensational feelings I was experiencing as my cock slid in and out of Karissa’s pussy and her sister fucked my face. I felt Amy’s cock as it filled my mouth and pushed down my throat when she would thrust forward. After several minutes, Karissa started breathing harder and moaning as her orgasm built. When she finally came she was almost screaming. The friction of the blonde’s pussy combined with her brunette sister’s cock was like heaven, but when Karissa’s pussy started to spasm I wished it would never end. The pleasure was too much though, and I felt myself getting ready to cum. I attempted to pull my head away from Amy’s cock to tell them I was close, but Amy had her hands on the back of my head and refused to let her dick leave my mouth.

 

Luckily for me, Karissa had become over sensitive after cumming and panted, “Amy…let him go…I can’t take any…more of this…” Amy released my head and withdrew her penis from my mouth. I slid my cock out of the tight pussy that I had been so enjoying and told them I was about to cum. Karissa immediately whirled around and engulfed my dick, trying to suck the cum right out. It didn’t take very long. I shot 2 or 3 shots in her mouth before she pulled it out and positioned it so that the next 3 or 4 shots landed on her face. She sucked the rest from my member and gathered all that she had collected in her mouth and gathered it on her tongue, which she stuck out for Amy and I to see. She drew her tongue back inside her mouth and swallowed. Amy sat beside Karissa on the couch and began licking and slurping the rest of my cum of her sister’s face.

 

I just sat and watched as the two sisters shared my cum and kissed. I was spent, and I knew I couldn’t go much longer. But Karissa and I had came twice, and Amy only had once, I knew that my work was not done. I turned my head from the beautiful sight before me to check the time, it was now 3:45 am. I was looking forward to the rest of the day.

Once back at my place I got us another drink and settled in on the couch.  I live alone because it gives me greater freedom with my "relationships."  Also it spares the girls from taking the infamous "walk of shame."  I could tell Irene was nervous so I made small talk to help her relax.  When I sensed the time was right, I leaned in and kissed her.  She responded by wrapping her arms around me and thrusting her tounge inside my mouth.

Slowly I kissed down her neck and bared her perfect breasts.  I sucked first one and then the other of her nipples, gently tugging them with my teeth.  She pushed me onto my back and undid my pants.  Pulling off my pants and boxers in one motion, she seized my cock and began sucking on it like a fiend.

I was in ecstacy.  This was positively the best blowjob I had ever had, bar none.  It wasn't long before I was jetting my cum into her mouth.  She swallowed my load and continued sucking until she had drained every last drop of cum from my cock.

Sitting up she licked her lips and said, "That was fun."

"It's your turn now," I replied.

"I should go now."

"Why? Because you're a lesbian?  I can still give you a good time."

"You don't understand," she pleaded, "I'm different."

Taking her hand I said, "It doesn't matter."  I kissed her lips in an attempt to relieve her tension.  I laid her back on the couch and began gently kissing her neck.  While continuing to kiss her neck, I pushed her dress off of her hips and pulled off her panties.  Rubbing the inside of her thigh I slid my hand upward toward her crotch.  And recieved the biggest shock of my life!

"Holy Shit!!" I cried as my hand grabbed a huge hard on.

"I tried to tell you," she said as tears began to fill her eyes.

Recovering from my initial shock I just stared, completely transfixed.  She tried to get up but I held her down.  Slowly I took her cock in my hand and gave it a gentle squeeze.  She let out a low moan so I began to stroke it.  She moaned louder and started to thrust her hips with each stroke of my hand.

What the hell was I doing?  Here I was with my hand on someone else's cock!  It was absurd!  I couldn't control myself anymore.  In a trance like state I lowered my head towards her cock, gingerly touching my tounge to the head.  There was a drop of pre-cum and I could taste its salty sweetness.

Slowly I took the head of her cock into my mouth.  I couldn't believe it, I was actually sucking cock!  I worked more and more of it into my mouth until I had the entire length of it and her balls were resting against my chin.  I withdrew it slowly before plunging all the way back down again.

Irene placed her hand on my head and began moving her hips back and forth, fucking my mouth as if it were a pussy.  She increased tempo and began burying her cock in my throat with each thrust.  Her breathing became ragged and she thrust  deep into my mouth, shooting her cum down my throat.  I swallowed all of it and continued sucking until she went limp.

Releasing her, i moved up and kissed her lips.  I carried her into the bedroom and laid her upon the bed.  Taking her cock in my mouth once again I began sucking until She had a rigid hard on again.  Irene leaned forward and kissed me and had me lay on my back.  She started sucking my cock again but quickly moved down to my ass hole.  She licked my sphincter for a minute, lubing it with her saliva.

When I was good and lubed, she lifted one of my legs over her shoulder and placed her cock at the entrance to my ass.  Very gently she pushed forward until my hole gave way and allowed her to penetrate me.  I cried out in pain but she very slowly began to move back and forth, going a little deeper with each stroke.  After she was all the way in she began to fuck me very slowly. 

At first the pain was almost unbearable but it soon faded and was replaced with sheer pleasure.  She continued to fuck me, moving faster and faster until she was pounding my ass like a cheap whore.  Reaching down I grabbed my cock and began stroking it in time with her thrusts.  It wasn't long before I shot my load all over my chest.  Almost immediately Irene drove all the way into my hole, let out a deep groan, and filled my ass with her cum.  Collapsing on my chest, she kissed me passionatley, and we drifted off to sleep.  This was one hell of a way to win a bet. 

The micro reactors were so cheap to make that they were immediately mass-produced on such a scale that within ten years every object produced my man that required an energy source was powered by a GAC micro atomic generator. Poverty disappeared; wars ceased to be fought; pollution was a dim memory of the past; and every power station in the world was dismantled. Unbeknownst to anyone GAC micro atomic generators emitted powerful zeta radiation that could not be detected by any man made instrument at the time. Zeta radiation is not life threatening to humans and has no effect on any other organism on the globe. It does have one effect on the female of the human species that was not to become apparent for some time.

At 1600 EST on March 13 in the year 2050 AD the UN announced that General Atomics Corporation had destroyed mankind. By then it was proven beyond any doubt that the zeta radiation emitted by GAC micro atomic reactors was the reason every woman in the world was sterile. The world was doomed.

At 0917 EST on April 16 in the year 2125 AD the last human being walking the planet Earth died. Clocks continued to tick, elevators waited for passengers that would never appear, automatic machinery continued to run, vacant offices and department stores were kept cool by air-conditioners and every man made appliance was fully functional; after all, they were powered by GAC micro atomic generators, and they had a one thousand year guarantee.

Five years before GAC had released its world saving (and world destroying) invention on the world, the governments of the first world countries of the world had agreed to conduct a radical experiment. At a number of secret locations throughout the modern world, volunteers had been placed in suspended animation in cryogenic facilities. The volunteers were mainly single men. They had no special skills or scientific training; they were simply ‘guinea pigs’ with no families or friends to miss them. The plan had been to see if humans could be preserved for extraordinary periods of time in the event that global warming put an end to man’s existence.

The experiment was really mute once GAC announced the invention of their micro atomic generators and the resultant reprieve for the world’s environment; but the scientists decided to continue with the test as it may provide useful data about extended hibernation in the event that the micro atomic generators could be used for inter-stellar travel. In fact all of the cryogenic facilities were retrofitted with GAC micro atomic generators to ensure they had an inexhaustible power supply. The volunteers in their cryogenic stasis were blissfully unaware of what had happened to the world while they slept peacefully for a hundred and fifty years. By the time the clocks ticked over to 0001 on January 01 in the year 2130 AD they were the only living human beings on a planet that had hundreds of fully functioning modern cities but was devoid of human habitation. My story begins.

My name is Michael, a forty four year old male, and I was one of the volunteers who participated in the extended stasis experiment. My cryo-chamber opened on time, and I emerged, along with my fellow cryo-volunteers, from my extended sleep to find all of the machinery and paraphernalia required to enable human existence was fully functional and yet the world was abandoned of human life.

It took myself, Steve and Jeff about a week to figure out exactly what had happened to mankind. At first we were stunned and then, when we got over the shock, we decided to make the best of a world abandoned by its creators. We moved into a secure compound, and foraying into the nearby city, we acquired all of the trappings we needed to live comfortably. We had three separate houses with all of the latest gadgets. Everything ran perfectly and mostly automatically, powered of course by GAC micro generators. We filled our houses with every form of entertainment available: three-dimensional holographic video projectors, fully integrated sound systems, and the latest computer games. Of course there were no interactive Internet websites, although most websites were still running; their servers and super-computers run by GAC micro atomic generator.

We found food abundant; advances in cryo technology meant that produce could be frozen and remain edible for centuries (the irony of this was not lost on us). We had everything we needed to sustain us for the rest of our lives. Everything except contact with other humans beside ourselves; and of course no women to fulfil our sexual desires. Jeff acquired a powerful transmitter and we spent days trying to contact the other volunteers of the cryogenic experiment who must have emerged at the same time as we did in their secret locations around the globe, but we had no success. Because of the secrecy surrounding the project we didn’t even know who they were, how many there were, or where they were located. We eventually became resigned to our fate and settled down to live out our lives in as much comfort as possible, leaving the transmitter and receiver to operate automatically.

After a six months of each other’s company we pretty much retired to our own homes within the compound. It was a sad reality that we craved the company of other human beings but were sick of our own company. This arrangement and the privacy we now all craved actually suited me more than I was prepared to say. You see I have a secret that the other two know nothing about; that very few people had ever known anything about. It was a secret that I had lived with before I volunteered for the cryo experiment and a secret I have no intention of sharing with my two male survivors. I am a transvestite.

Jeff, Steve and I agreed to meet every Friday at one of our houses in the compound on an alternate basis. Why we chose Friday (the start of the weekend had no relevance to us now) was beyond us; we just mutually agreed to the day. We would not disturb each other outside of our Friday evening get togethers unless there was an emergency. We all craved our privacy, me most of all. Now that I lived in relative privacy, I decided that I could practice my crossdressing peccadillos as often as I wanted.

I drove into town and acquired all the trappings I needed to fulfil my transvestite fantasies. I went to various shops and took makeup, perfume, jewellery, lingerie, shoes, wigs, skirts, blouses and suits. From chemists shops I selected a variety of shavers, hair removal cream, and lubricants. I visited sex shops and helped myself to vibrators, dildos, a life-like male sex doll, fetish clothing and holographic transvestite video pornography. I smuggled it all into my house, locked the doors, closed the curtains and commenced to live my life as my alter ego: Michele.

I took all of my acquisitions into the second bedroom and ensuite bathroom of my house and filled the drawers, shelves, cupboards and wardrobes with my girly goodies. I put black satin sheets on the bed, installed a computer, a holographic video player and set up a digital video camera. I put in a huge dressing table complete with lighted mirror, wig stands, makeup case and jewellery box. When I had the bedroom and ensuite set up exactly as I wanted, I installed a phone line and intercom system to the front door and then put a huge deadlock on the bedroom door. My plan was that while I was in this room, which I called ‘Michele’s Playroom’, I would be Michele and play whatever girly games took my fancy. The intercom and phone systems would give me some time to transform back into Michael in the event of an unannounced visit from either of the other two men with whom I shared planet earth.

I knew it would be risky; being dressed up as a woman with the only other men in the world (that I knew existed anyway) living close by; but I figured I had reduced the risk as much as I could. If I had to live in a world without the comfort of contact with women; then I would enjoy as much time as I could pretending to be one. I am not gay but I have been crossdressing all my life since my early teens. I must admit to having fantasies of being with men whilst I am dressed as Michele but I have never acted on them other than masturbation. All of my sexual encounters have been with women and I have enjoyed every one of them. But there are no longer any women in the world; my sex life will consist of fantasy, pornography and masturbation. There is no way I could even conceive of revealing my transvestite lifestyle to Jeff or Steve.

One evening when I decided I had done all I could to ensure that I could enjoy my solitary transvestite fun without getting caught out, I went about making the changes I needed to transform from Michael to Michele. I entered Michele’s Playroom and carefully locked the door.

I had already begun to allow my nails to grow long; not long enough to be too noticeable, but long enough to be feminine when filed and painted. I took a long bath and after soaking for an hour I carefully shaved my legs, feet, arms, hands, under-arms, chest and stomach. I had trimmed my pubic hair right down to stubble before I entered the bath and I now shaved my pubis to a nice shape and then carefully shaved my scrotum.

I have only a small thatch of hair in the small of my back, which I shaved with the razor to the best of my ability. I got out of the bath and dried myself and then applied hair-removing cream to the remaining stubble in the small of my back and over and in between my buttocks, paying particular attention to the area around my anus. I shaved my face carefully, twice, so that there was no rasping when I ran my hands over my chin, cheeks and neck. Finally I trimmed my eyebrows and shaped them as best I could so that they would not look too feminine when I was dressed in drab as Michael.

I showered to rinse off the hair remover and remaining suds, towelled off and then slipping into a satin bath robe I sat before my dressing table ready to begin my first transformation from Michael to Michele in over one hundred and fifty years. Although it was over a century in real time, to me it seemed like only a few months since I had dressed as a woman because the stasis condition induced by the cryogenic chamber made it seem just like being asleep for one night. But as any committed transvestite or crossdresser knows, a few months without dressing felt like an eternity.

My usual ritual began; I looked at the amassed cosmetics, wigs and womanly accoutrements laid out before me, sighed with bliss and began to work on my makeup. First I applied a liberal amount of foundation, a slightly shade darker than my natural skin tone. Next I brushed a coating of face powder all over my face to set the foundation. I reached out and took a sip from the glass of the red wine I had poured prior to entering the Playroom; a nice Australian Shiraz, vintage 2125. I then went to work on my eyes.

I like to do my eyeliner next so that if I get it wrong I can clean it off and start over; if I apply the liner after I have my eyeshadow right, I get annoyed. I applied a thick line of black eyeliner to my upper and lower eyelids and then painted my eyelids with a blend of light blue and pink eyeshadow. I covered my eyelids and brushed it up to the top of my eye sockets. I brushed lashings of mascara on to my upper and lower eyelashes, allowing the mascara to set between coats whilst I sipped the Shiraz. No need to rush after all its not as if I’m going out or meeting anyone!

Having finished with my eyes and happy with the results I rouged my cheeks and then applied two generous coats of liquid lipstick. Perfect! I was happy with the results; my face was heavily but carefully madeup; a sort of middle aged slut look that I liked. I applied a final light coating of face powder to give my face a lovely glow. I took my time applying two coats of plum red nail polish to my finger and toenails; gulping red wine between coats and refilling my glass. I selected a raven black bob wig that just brushed the nape of my neck, the fringe falling across my eyebrows. I loved the result!

I rummaged in the jewelbox and put two silver necklaces around my neck and matching bangles on both wrists. I clipped silver drop earings to my ears and laid out an anklet for later, after I had put on my stockings. I was now getting a little aroused and a droplet of clear seminal fluid dripped from the eye of my penis. Now for the best part of dressing; slipping into my lingerie!

I shimmied into a black satin garter belt and slid fully-fashioned taupe stockings on my legs. I smoothed the sleek nylons taught, straitening the seams and pulling the reinforced tops up to the tops of my thighs and attached the garter straps. Then I slid into a pair of pink nylon boy-leg panties, pushing my penis between my legs. I clipped the silver anklet around my right ankle being careful not to ladder my stocking.

I was so happy that despite the passage of time, sexy lingerie had not changed, right up until their extinction women had still craved sensuous slinky underwear. Next I slipped into a black satin push-up bra; I stuffed the latex breastforms I had taken from a sex shop into the cups and adjusted them to look as natural as possible. I eased a white satin full-slip over my head and let it fall, shivering with pleasure as the diaphanous material slithered down my body, especially when the hem ran down my stocking legs creating sparks of delight at the feel of the satin against the lycra and nylon hosiery.

I slipped into a navy blue rayon mini skirt and pulled it up and secured it at the waist and then pulled on long-sleeved white nylon blouse and tucked it into the waistband of my skirt. I had my usual struggle with buttons because they are on the ‘wrong side’. After collecting a pair of patent leather black high-heeled pumps I sat on the bed and slipped them on my nylon encased feet. I stood and looked in the full-length mirror.

"Beautiful Michele," I whispered and kissed my reflection.

My cock started to thicken, trapped in my nylon panties and I couldn’t help but slide my hand under my skirt and run the tips of my red fingernails over my panty clad silken cock. I closed my eyes and imagined it was a handsome man doing this naughty act. What I didn’t realise was that I actually did have a handsome man in my house!

When I opened my eyes a minute later I had the biggest shock of my life; right in front of my face was a huge throbbing penis! I looked up in surprise and there was Jeff smiling down at me, his hard cock sticking out of the fly of his jeans.

"Well don’t just look at it; swallow it you fucking queer!" he snarled and pushed his cock against my face.

Jeff rubbed his cock all over my face; laughing as he humiliated me.

I was stunned; how had he got in here? Why was he doing this? What could I do to stop him?

"Jeff; please, don’t do this. I won’t tell anyone ok?"

"You have to leave," I begged.

"Leave? Won’t tell anyone? What do you fucking think is happening here you stupid cunt!" he snarled.

"The world has ended; there are no women left. But there is this fucked up bloke who lives next door who likes to dress like a woman. He even calls himself Michele! So now by default you Michael, by changing yourself into Michele, have become the last woman in the world!"

"And now Michele is going to suck my dick or I’m going to punch her in the face," he hissed and pushed his engorged penis against my red lipsticked lips.

"Now open up bitch!" he warned and pulled my head into his groin.

Jeff’s cock filled my mouth and I started to gag. Jeff then held my head commenced raping my face. He thrust his pulsing, penis in and out of my mouth grunting as he fucked my face. I was stunned and had no way to react other that to sit there and let him commit this unspeakable act. My head was spinning trying to figure out how Jeff had hid in my room. How did he know I was a Transvestite? What could I do; it’s not like I could call the police is it?

It was strange feeling a cock in my mouth for the first time. It was not unpleasant; in fact in a way Jeff was forcing me to live out my fantasy. My lips clamped around his turgid penis and my tongue slid along his shaft; it was like I knew instinctively how to fellate a man. Jeff pushed my face back until just my lips circled his plum coloured knob; then pulled me forward against him as he thrust forward, forcing his turgid meat into my mouth. As a reflex I flicked my tongue along his shaft and glans and began to sense his enjoyment. Now he increased his attack on my virgin mouth and I tasted more and more of his pre-seminal fluid. He was groaning and panting.

"Yeah fucking whore! You like this don’t you! Take my cock bitch!" he growled.

He slammed forward hard and pushed my face into his groin and held it with two hands at the back of my head. His penis throbbed and erupted in my mouth and I felt the hot salty taste of his seed as it exploded from his glans. I started to gag and tried to force myself free as his semen flooded my mouth and slid down my throat.

"Take it bitch, take it!" Jeff howled in his orgasm.

"OH Yeah baby, on your face yes! On your face!"

Jeff pulled my face out his groin and held it close to his crotch with one hand; with the other he rubbed his still ejaculating penis all over my face. His ejaculate shot across my cheeks and landed on my eyelashes, a string of hot semen running across my face. Another spurt shot against my lips and up my nose. I felt stream after stream of semen scald my face and start to run down my neck. The thick gobbets of milky come smeared my cheeks, nose and lips. Looking out my eyes I could hardly see because of the ropes of hot come across my eyelids and lashes.

Jeff's orgasm started to subside and he continued to rub his cock all over my face. He smeared his spend all over me, it combined with my lipstick and makeup to make a hot sticky film that covered my face. Jeff stepped back and looked down at me, sitting on the bed, may face covered in come. Gobbets of semen glistened on my navy blue skirt and soaked into my taupe nylon stockings because some of Jeff’s fluids had run off my face.

Jeff smiled down evilly at me and began to unbuckle his belt.

"You’re not too fucking bad a cock sucker for a bloke Michele," he sniggered pushing his jeans down and unbuttoning his shirt.

"Now let’s see how the last woman left on the planet knows how to fuck?"

Â

To be continued…………………………………………….

Â

"Now I can get out of these stupid fucking women's clothes and get back to my own cell!" I said, relived that the evening had come to an end.

Carmel and Charlotte stepped into my workroom cell, silently closed the door, and leaned back menacingly against the bars,

"Oh no Michele, you don't understand! We've finished with punters tonight, but WE haven't finished with you!!!"

 

Part VII

'Oh no!' I think to myself, 'all the degradation I have had to put with over the last seemingly endless hours, and now, just when I think it's over, these two have come for their pound of flesh!'

I look at the two transvestite hookers who have ominously just stepped into my cell, one is a seductive 'Vampira', the other a sexy slut punk, the shock and bewilderment is obvious on my face and for umpteenth time tonight I started to cry.

"Ok girls; please just get it over with as quickly as possible, and please don't hurt me, I'll do whatever you want but I don't want to get hurt any more," I implore, hoping they will take what they want quickly and then let me go.

"Oh Michele sweetheart," Carmel sighs moving towards me with her arms open, "you poor, silly sweet thing; we aren't here to hurt you; we're here to comfort you after your first night at work. Look!" she says, pointing at Charlotte.

Charlotte is smiling and holding up a bottle of whisky, which she been concealing behind her back.

"Come on hun, lets sit down and have a drink," she smiles and leads me to the bed removing her black satin opera gloves and dropping them to the floor.

I sit down with relief and cross my legs. The swish of my nyloned thighs rubbing together sends a little jolt of pleasure through my body. Carmel sits beside me and offers me one of her menthol's whilst Charlotte pours large measures of whisky into three tumblers she has found somewhere in one of the cupboards in my workroom.

I extend my trembling fingers, my fingernails glint a dull red in the subdued light, I take the proffered menthol and bring it to my lips. Carmel extends her bright red fingernailed hand and flicks the bic lighter into life; I drag back on the cool menthol cigarette and blow out a plume of smoke towards the ceiling. I look down and am surprised to see the filter of my cigarette is ringed with lipstick. I laugh to myself at the red, lippy stained cigarette butt and flick a lock of hair out of my eyes.

Crossed legs, lipsticked cigarette butts, flicking my hair! I have adopted all these female mannerisms in such a small time; 'It's as if I was born to this!' I think to myself.

'No!!! Never!!! I won't give in to this sick life!' I force myself to say in my mind, 'I'm a man, a man, a MAN!!!!!

I bring my head up and my face is level with Charlotte's chubby knees. Her ripped black fishnet stockings are indeed being worn over shiny taupe tights as I suspected. My eyes move up her thick but shapely legs, past the tiny tight Lycra mini stretched taught on her thighs, past her slashed T-shirt with the words "Fuck Slut" printed on it in silver sequins. She is proffering me a tumbler of whisky, and, as I reach out to take it I look up into her plump pretty face and whisper,

"Thank you."

"Your welcome honey," she smiles back, her heavily made up face and punk bottle-blonde, pink and blue streaked wig make her look sexy in a 'street whore' kind of way. Her heavily eye-shadowed and mascaraed eyes gleam in the darkened cell.

Charlotte pulls up a chair and sits directly in front of me offering a drink to Carmel and accepting a lighted cigarette in return. I take a pull on the tumbler and the fiery liquid burns my throat as I swallow it; I take another hard pull on the menthol and erupt into coughing fit. The coughing continues as my throat, sore from the abuse it has taken from the 'punters', spasms from the irritation of the smoke and strong liquor.

"There, there," offers Carmel as she takes the drink and cigarette from my hands and hands them off to Charlotte who places the cigarette in an ashtray and the drink on the bedside table.

Camel pulls my head to her shoulder and gently strokes my back as the coughing fit slowly subsides. I can smell her perfume, I recognise the brand as 'Poison,' and my head nestles in the crook of her neck. My arms instinctively wrap around her and I return the hug. I hug her gently as I start to sob into her neck and she continues to stroke my back and slowly rocks me back and forth in the light embrace. She whispers in my ear,

"It's alright Michele; It's alright honey."

I start to drift off as my senses experience the wonder of this sensuous embrace. My satin blouse slides stimulatingly over Carmel's tight, body hugging black satin dress and I can feel the heat of her body even though her breastforms. Our knees are lightly touching, the diaphanous nylons delicately stroking each other, her black pantyhosed leg peeking through the split in her dress and my silk stocking thighs become further exposed as my skirt rides up as we continue to embrace.

In my reverie, I feel the beautiful soft butterfly of Carmel's breath as she exhales sweetly in my ear and whispers,

"There, there, honey; it's all better now; Carmel's here sweetie, Carmel's here."

I raise my head and look into her heavily made-up eyes; my gaze roams over her red lips and pale skin as my right hand moves up and gently strokes her cheek, my ruby-red nails in stark contrast to her pale Goth makeup. My hand continues up to her lustrous black wig and entwines itself in the silky softness of the fine hair. I gently pull her face to mine and our lips brush; I slip my tongue across her lips and taste her lipstick.

Carmel looks into my eyes deeply and reciprocates; her hand slides into my hair and she pulls me forward until our lips softly meet; her tongue cautiously extends and brushes my lips. Then, at the same time, we open our mouths and mash our lips together, our tongues entwine and our bodies push against each other, satin and nylon come together to create an exquisite rasping sensation that causes my little penis to awaken in its silken panty prison.

The strangest feeling envelops me, our caress is so soft and gentle, feminine, comforting and at the same time sexual. My head is spinning with the new sensations that course through my body; after the brutal treatment I have received over the last pitiful hours the tenderness that Carmel is bestowing upon me has me entranced.

Carmel eases me back on the bed until my head comes to rest on my pillow; our kiss is not broken and a sense of urgency seeps into our embrace. Carmel strokes my face and showers my lips, cheeks and eyelids with soft loving kisses; my head spins in a heady sensation of soft feminine yearning. She adjusts herself so that she is half on the bed, her legs straddling mine as her silken, nylon clad knee rubs softly against my stockinged thighs.

My penis has now freed itself from between my legs and is rampant in the front of my panties. Carmel sighs sweetly in my ear as she softly kisses my lobe, her perfume mingling with mine to create a dizzy cloud that further heightens my senses.

"Michele, honey; you are so lovely," she whispers.

Her hand slides up my inner thigh and my penis pulses, the light rasp of her nails on my stockings sends waves of pleasure through my body. I pull her body harder against me and pull her soft lips against mine, our tongues intertwining in a sweet symphony. Carmel's hand slides under my skirt and I gasp as she tenderly strokes my erect member through my silky soft nylon panties.

I suddenly realise what I am doing!

"No! Stop! This isn't right!" I cry as I push Carmel's body away from me.

Carmel lowers her face to mine again and tries to kiss me but I squirm and turn my head away.

"Fuck off you pervert!" I sob.

"This is sick; I won't be like you! I won't submit to this twisted, sick existence that you and your perverted friends seem to enjoy. Get off me you fucking transvestite hag!"

Carmel pushes herself over me so that she is straddling my waist, the split in her skirt is wide open and the garment has ridden up around her waist. She grabs my wrists and pushes my hands back behind my head locking them there. She looks into my eyes with a cruel sneer on her face, her pale makeup making her look much more like a vampire because of her pale skin, red lips and dark made-up eyes; her teeth glint evilly in the lamplight.

"Well 'Little Miss I'm too good for you', I guess we have tried being nice. Obviously you only understand pleasure when it's forced upon you. We know you have really enjoyed the night's proceedings; Eddie told me you came when he fucked you and that bulge there in your knickers is a dead give-away." She sneered.

"Charlotte, plan B," she laughed.

I am pinned down with Carmel straddling me, forcing my hands back against the bed-head I twist my head to the left to see what Charlotte is up to. She rummages in the drawers of my dresser, gives a triumphant yelp, and comes over towards the bed with a pair of stockings in her hands. Before I have a chance to move she has lashed my left wrist to the iron bedpost and has started working my right.

I fight and buck trying to dislodge Carmel and pull my arm free from her grasp, but I am spent from the evening's ravaging and eventually I give up. Charlotte lashes my right wrist to the other iron post with the remaining stocking. Again I am forced to succumb to my captors.

"There now that's better; our spoilt brat has been tamed," gibes Charlotte.

"Now Michele, I'm going to tie your ankles to the bed just like your wrists and if you struggle Carmel is going to belt you; aren't you dear?"

"Oh please struggle honey, there's nothing more I'd like than to belt you one across your smug, pretty face." Carmel replies.

'Why are they being so cruel' I think to myself, bewildered. 'They had so been so nice earlier on!'

I submit while Charlotte finds another pair of my hose and lashes my ankles to the bed-base; she has to tie one end of the stockings to the steel bedpost and the other to my ankles because my feet do not reach right to the end of the bed. This allows me some small movement in my legs due to the stretchiness of the nylon stockings.

"Now; lets get started shall we?" smirks Carmel to Charlotte.

Carmel lowers her heavily made-up face to mine once again. I struggle and turn my face to one side to evade her kiss. Whack!!! Carmel slaps my face with her open hand.

"Come on Michele, you liked this before, now stop playing coy," she smirks.

Carmel lowers her lips to mine as I force myself to hold still while she does to me what she wants. Her soft lipsticked lips gently press themselves against mine, my lipstick smears and mingles with hers as she pushes harder and her lips crush themselves on mine.

Carmel's tongue pushes between my lips and slowly slides over my teeth. I capitulate and open my mouth and run my tongue against hers and taste her sweet mouth. My penis hardens again and rustles against my nylon panties. Then I feel a cool hand slide up my stockinged leg and under my skirt; it strokes the top of my thigh and slowly the fingernails scrape up the bare skin where my stockings end and up to the bulge in my silken full-cut panties. The nails slowly scrape across my nylon-encased cock and I sigh into Carmel's mouth and push my lips harder against hers. I surrender; the stimulation is too much.

I realise that Charlotte has moved down the bed and it is her ministrating to my engorged penis. The feeling of Carmel's soft lips against mine, her silken body straddling me as she forces her kisses on me, and the slow torture of Charlotte's fingernails against my panty-clad member are too much to fight against; I push against my bonds lifting my face to reciprocate Carmel's kisses and raise my skirted ass up off the bed to encourage Charlotte's caresses.

"Oh the bitch likes this after all; maybe all she needed was a little persuasion," Charlotte giggles.

"Let's try some more persuasion and see what happens," she laughs.

I feel my skirt being rucked up and bunched up around my waist. I can't help but assist by raising my ass off the bed; Charlotte now has my hard cock firmly gripped in her hand through my sheer nylon panties and is slowly working her fist up and down it; the feeling is delightful. Carmel has adjusted herself so she is lying on top of me, her upper body encased in her skin-tight silky dress is pushing against my satin blouse crating little butterflies of sensation. One hosed leg slides up and down my stockinged leg driving me wild with lust.

Charlotte's hand reaches inside my panties and frees my erect member pulling it out of the waistband; she strokes it gently now, slowly up and down, dragging her fingernails over the sensitive glans at the top of the up-stroke. I groan again.

"Oh Carmel! Oh Charlotte! You naughty girls!" I whisper into Carmel's mouth as she continues to kiss me deeply.

She is now stroking my face and pulls her face away from mine briefly; she looks in my heavily made-up eyes and whispers back,

"I knew you would like this; I'm going to make this special for you Michele."

Carmel then lowers her luscious lips to mine and we continue our passionate kiss. Then I feel Charlotte's hot breath on my thighs, she is kissing my stocking tops as she slowly wanks me with one hand and caresses my panty-clad balls with the other. Her kisses move up my thighs and across my nyloned balls and then I feel her hot wet mouth engulf me.

I groan again and rise my ass up off the bed in acceptance of Charlotte's oral worship of my shaft. My tongue is wildly exploring Carmel's mouth and I strain against my bonds to kiss her harder. Charlotte is working her mouth up and down up erect member, her tongue fluttering against the glans. I am close to coming. Carmel pulls her face away from mine briefly and whispers,

"Look!"

I raise my head as much as my bonds will allow and look down my body as Carmel slides over to one side so as not to obstruct my view. Looking down I see my legs spread; my ankles tied with the stockings which are lashed to the bedposts. I see my slender legs encased in silky flesh toned stockings, the reinforced nylon stocking heels visible in my strappy white high heels. My white leather miniskirt is bunched up around my waist and there is Charlotte's head buried in my groin.

Charlotte lifts her head slightly and turns to look up at me; she is beautiful for a plump girl. Her face is framed by the shocking, frizzy, bottle blonde wig with pink and blue streaks running though it, her heavy makeup with black eyeliner, dark pink and powder blue blush, and glittery multi-coloured eyeshadow. Her glossy bright red full lips grip the shaft of my penis.

"See," giggles Carmel, "I told you we came to comfort you."

Carmel now straddles me again and as our nylons rub my cock spasms in Charlottes mouth.

"She's ready for you Carm," Charlotte declares removing her head from groin, "and you better be quick!"

I wonder what she means……………..

Then it dawns on me as Carmel adjusts her position over me, she reaches under her dress and I hear a ripping sound as she tears the gusset seam of her pantyhose with a fingernail.

"Just relax honey," she whispers and kisses me briefly.

Then she adjusts herself again so that she is sitting over me with her lovely ass over my erect penis. She hitches up her dress. With one hand she pulls aside her panties and torn pantyhose gusset whilst with the other she grips my penis and positions it against her puckered anus.

Carmel slowly lowers herself onto me and I slide into her all the way. She pushes down and her panty-clad ass cheeks rest on my thighs; the nylon of her panties and torn hose rub against my shaft and balls as she slowly starts to ride me, putting her hands on the bed behind her to support her weight as she fucks my rock hard clitty.

Charlotte moves up to the top of the bed and begins to kiss me slowly, her tongue throbbing in my mouth as my penis throbs deep in Carmel's ass. My cock feels so snug and tight as Carmel rides me, her sleek back passage spasming against my invading member. Carmel is groaning and moaning,

"Oh Michele, fuck me!"

"Michele Fuck Me!"

"Michele………FUCK ME!!!!!"

I am delirious with passion, my clitty is trapped deep inside Carmel and as she rides me I push up to meet her as she slams her pantied ass against my groin. My silky lingerie is sending little explosions into my groin where it comes into contact with Carmel as she bucks over me, the rustle of silk, and nylon and satin becomes the background music to our groans and sighs as we approach orgasm.

I open my eyes because has Charlotte stopped kissing me, I am disappointed because her lipstick kisses were adding so much to my stimulation. I turn my head to see that Charlotte has freed her short stubby cock from her panties and is viciously wanking it. She looks down into my eyes and I see the pleading there.

"Please?" she whispers.

"Ok," I whisper in capitulation.

Charlotte kneels on the side of the bed, her stubby clitty sticking out from her groin, her sleek dance tights are pulled down and her fishnet stockings strain on the red garters where she has roughly adjusted her underwear to allow access to her angry little cock. She has pulled off her Lycra mini and dropped it around her high-heeled feet.

I can't move my head too far because of my bonds but I turn my head to one side and greedily suck Charlotte's hard fat clitty into my mouth. It tastes salty but clean and I immediately begin to suck it and slide my tongue all over it. The sight of my fellatio act must have aroused Carmel further because she is now bent forward over me and is slamming her ass up and down on my cock in a frenzy. My penis is now throbbing with excitement and I can feel my orgasm build as Carmel's hot ass pulses against my cock and drives itself up and down my shaft.

Charlotte is now groaning in time with Carmel as I suck and lick her fat little hard clitty-cock. I can feel it begin to spasm.

"Fuck me Michele!" Groans Carmel.

"Suck me Michele!" Groans Charlotte.

And I do! I fuck and suck and I come! My penis explodes deep in Carmel's ass and I rise up to thrust it in as far in as it will go. Carmel responds and pushes down grinding her pantyhosed ass against my panty-clad balls as I unload steam after stream of hot semen deep in her back passage. At the same time Charlotte grips my head and pulls my face into her groin as she jets huge globs of her seed into my mouth.

The experience an orgasm like nothing I have ever felt. My cock is exploding with the friction and pulsing of Carmel's tight ass; my balls are electrified by the sensation of Carmel's panty and hosed ass rubbing against their silky nylon panty prison; my mouth and lips are on fire as I suck and swallow Charlotte's hot seed, the feel of her stubby member invading my mouth is beautiful; and all over my body, the silky satin feel of my lingerie, skirt, blouse and stockings is amplifying the electric pulses of the most fantastic orgasm of my life.

After about three minute of intense pleasure, Charlotte removes her flaccid penis from my mouth; a trickle of her spend drops onto my chin as she tucks her angry little weapon back into the gusset of her sheer dance tights. Carmel eases herself off me, giggling as my cock plops out her ass. She stands next to the bed and adjusts her clitty inside her hose and panties and smooths down her black satin sheath dress. It's only then I notice the semen stains on her underwear and realise she has ejaculated whilst I was fucking her.

I lie there, my hands and feet tied, my skirt hiked around my waist; nyloned legs spread, my slowly deflating penis sticking out of the waistband my sheer panties. My makeup is smeared and wig tousled due to the passionate struggle I have just endured and enjoyed. The single drop of Charlotte's semen glistens on my chin.

"That was wonderful!" whispers Charlotte.

"Wonderful!" whispers Carmel.

"Wonderful!" I whisper.

"Fucking wonderful ladies; I really enjoyed the show. Now who the fuck gave you permission to play those sort of games!"

Oh my God! It's Eddie. He's looking though the bars of my workroom cell pushing his sticky, gnarled cock back into his pants. A pool of semen glistens at his feet in the low light.

"Now; how the fuck am I going to punish you girls for using something that I own and that everyone else has to pay for to use!"

"YOU!!!!!" he screamed pointing his shaking finger at the three of us.

 

 

To be continued……………………………………………….

“Amy’s Surprise 2:

Enter Karissa”

 

by Matthew Ford

 

“What did you think?” Amy asked.

 

“Well, let’s see…” I started to answer, “You gave me the best blowjob I’ve ever gotten, sucking your dick was about the best thing ever, and sharing your cum with you was incredible…all in all, I’d say it went well.” Amy smiled and walked over to sit with me on the couch. We sat quietly drinking our Gatorade for a few seconds until I decided to say something, “Ames, when you came, I swallowed probably a third of it, quite a bit dripped from my mouth, then a lot spilled on your boobs, and there was still so much…do you always cum that much?”

 

“Not always, but most of the time it’s pretty close to that. You did a really good job sucking me off though, that definitely helped. I didn’t think there would be that much ‘cause I jacked off before you picked me up tonight. I’ve had to do that a lot lately…I’ve been really excited about tonight.”

 

“Do you always swallow your own cum? ‘Cause, if you do, I gotta say, I’m impressed. You must really like it.” Amy just smiled as some blush showed on her cheeks.

 

“What about you? Did you like it?”

 

I thought for a second and responded, “Well, it wasn’t bad. I mean, it didn’t taste great, but it felt great. Feeling your warm cum going down my throat was awesome.” Just then sounds started coming down from upstairs. It surprised me at first, until I remembered that Karissa and Brian had hurried to her room when they got there. I could hear Karissa moaning. “They must be having fun.”

 

Amy had started laughing mildly when Karissa’s whimpers of pleasure reached the living room. “She does enjoy getting pounded. I’ve never known anybody who likes it as hard as she does.” This brought a thought to my mind.

 

“So, she doesn’t have, I mean, she isn’t like you?” I asked.

 

“No, she’s a normal girl. And she’s got a really small, tight pussy.”

 

After a short pause, I asked, “So do you two ever…?”

 

“Not as much as we would like,” Amy answered before I finished asking, “We do it probably once a week. Our mom is home a lot. When we used to share a room we would do it almost every day, but when Nathan left for college and I took his room that kinda stopped. Now I sleep downstairs, and it’s just too hard for either of us to sneak into the other’s room without waking up our parents. Whenever mom and dad go out we can really go at it, but other than that we have to just fool around a little bit here and there during the day. Karissa loves anal though, I usually butt-fuck her when our parents are out. That butt-plug you’re holding is hers.”

 

I had been looking through the paper bag that Amy had thrown me earlier. “Wow,” I said, “This has actually been in her ass? All the times I fantasized about her ass, and now I’m holding her butt-plug.”

 

Amy suppressed a small giggle and said, “Yeah, I bought it for her for her birthday last year. We both use it, but I only can when she isn’t, which isn’t as often as I’d like, she loves that thing,” Amy laughed a little bit as she said this. “When she gets home from track practice, she usually puts it in and keeps it there till dinner. Sometimes she even sleeps with it in!” I was amazed at this, I had no idea anybody could like having something in their ass that much. Just then Karissa let out a loud moan followed by several repetitions of “oh my God.” I knew she was cumming. I drifted off into a daydream about her. Karissa was the cutest sophomore at our school, she had blonde hair that went just past her shoulders, brown eyes, a really white smile (just like her sister), and since she ran track, her body was pretty thin. Her legs were muscular, and her ass firm. She had small boobs, I’m not sure what size, but I’d venture a guess that they were mid-A cups. Karissa always wore tight jeans and colorful, loose tops, which was a good wardrobe choice since it accentuated her great lower body and made her small breasts appear larger. She had started at the high school her freshman year because she wanted to get the “high school experience”. That year, when I was a sophomore, she was a football cheerleader, she distracted me every game, which I didn’t mind too much since I hardly ever played anyway.

 

As I was thinking about Karissa’s body and imagining what she would look like under her clothes Amy spoke up, “You know, I’m sure that if I was given a few minutes I could convince Karissa to join us.” Just as I was about to tell her how much I would love that, Brian let out a loud groan, he had obviously climaxed as well. “Okay, if you want her to, you’ll have to give me some time to talk to her. She never lets guys stay for very long after they finish, so you go and take a shower in my bathroom, and I’ll go upstairs and talk to her and make sure Brian leaves. Make sure you’re in there for at least 20 minutes ‘kay?” I was going to say ‘alright’ but before I could she hopped up and headed toward the staircase. Amy looked back and said, “Hurry up,” then quickly went upstairs. As she went I watched her tits and cock bounce. When she was out of sight I leapt to my feet and hurried to her shower.

 

As I was showering I made sure to clean my dick and ensured that my sphincter was clean. Tonight I could have Karissa’s butt-plug or even Amy’s dick in it, and I wanted to be ready. I periodically poked my head out from behind the shower curtain to glance at the clock. After 20 minutes had passed I got out and dried off quickly. I put the towel around my waist and stepped from the bathroom. I walked through Amy’s room and into the living room. I expected to see Amy and Karissa fucking on the floor, but to my surprise, I saw only Amy, sitting alone on the couch watching TV. I looked out the window and saw Brian’s car was still there. “Oh well,” I thought to myself, “Hell, I got Amy, I guess wanting Karissa too was selfish. I can still fuck Ames, and maybe she will fuck me too…” I had desperately wanted to fuck Karissa though. I sat behind her in U.S. History, and I fantasized about her almost daily. I had had a crush on her for years after I met her. From 7^th to 10^th grade she was all I thought about, but I had never been able to get close to her. “And here, tonight,” I thought to myself, “I was foolish enough to think I might get to fuck her…”

 

I walked up behind the couch where Amy sat, naked. I stood behind her and looked down at her body. Her boobs showed remnants of where her cum had landed, and where I had licked it off. Her nipples were perky, and her dick was semi hard. Just as I was about to tell her that not getting Karissa to join was alright and that all I needed was her, I heard somebody in the kitchen. I looked to my left and stopped in my tracks. Karissa walked into the living room completely nude with a bottle of water in each hand. Her breasts may have been small, but they were round and perky. The nipples were small and pink. Her stomach was firm and she was tan all over. When my eyes finally came to rest on her pussy, my mouth dropped open. It was shaved clean except for a small rectangle of very light brown hair on her crotch above the pussy. Karissa walked over to the couch, handed Amy a bottle of water, then turned to me and asked if I wanted one. “Sure,” I said. She turned to go back to the kitchen and when I looked to watch her ass as she walked I saw the square base of her purple butt-plug sticking out. My eyes widened at this as Amy reached over the back of the couch and wrapped her fingers around my now hard cock.

 

“I thought you’d like her. Wait till you’re in her pussy…it’s amazing,” Amy said as she looked into my eyes. I went around the couch and sat next to Amy. I laid my hand across her lap and started squeezing her cock. “I think you should put this on,” Amy said as she held up a condom, “I don’t know how long Karissa is gonna wanna wait.” Amy then opened the condom package and started rolling it down my dick.

 

“What about Brian? Is he in the kitchen?” I asked.

 

Amy smiled and replied, “No, he was pretty drunk so Karissa called Kyle to come get him. You have us all to yourself.”

 

Karissa walked in with another bottle of water and handed it to me. She stood in front of the couch between where Amy and I were sitting and said, “Well, well, well…” she bent down, grabbed my cock head with her thumb and forefinger, and went on, “A bit presumptuous, don’tcha think?” I smiled nervously and looked to Amy, who just smiled wickedly at me. Karissa continued, “I’m gonna jump in the upstairs shower for a few minutes, you two have fun.” She turned around and bent over slightly and asked in a really seductive voice, “Matt, will you get that for me?” I reached out, grabbed the base of the purple butt-plug, and started pulling it out. However, Karissa tightened her rectal muscles, and as I started pulling harder she opened her mouth and moaned slightly. When it finally popped out she let a sexy whimper leave her mouth. Karissa stood back up and as she started walking up the stairs she looked back and said, “It’s a good thing you got it out, you’ll need it more than I will.” She then winked at Amy and disappeared down the hallway.

 

It was then that I felt Amy pulling the butt-plug away from me. I looked over in time to see her start rubbing KY Warming Liquid on it. “Roll on your side,” Amy whispered sweetly with a smirk on her face. I hesitated and she continued to say matter-of-factly, “Well come on, your ass isn’t going to loosen itself up.” I leaned to my right, away from Amy and when I was on my side, I felt her fingers massaging my ass with the KY. When she removed them at first I was disappointed, but when I felt the butt-plug start to poke into me, I was nervous. I was just about to ask Amy to wait when she pushed it in seemingly as hard as she could. I groaned in pain as it stretched me. She started pulling it out and then rammed it back in, she did this again, and again, fucking me with it. After probably 30 seconds she forced it in and left it there, telling me to sit up. I did and as I did I could feel my weight pushing it in farther. I closed my eyes and Amy’s hand began rubbing my dick. I looked down and she was lubing it up with the KY. She then stood up, and still facing away from me, maneuvered herself over me. She lowered her body until she was almost on my lap. Amy reached down and adjusted my dick so that it was at the entrance of her amazing ass. Then she lowered herself onto it slowly, but before all of it was in she rose back up just as slow as she had come down. After repeating this several times, Amy suddenly slammed her ass down into my lap and my cock was thrust into her. She rapidly began riding me. Every time Amy’s ass hit my lap it forced me lower which, in turn, forced the butt-plug farther into my ass. Both sides felt great, and I knew that it was just a matter of time before I blew my load. I reached my hand around and grabbed Amy’s rapidly bouncing 8 inch cock and started pumping her as quickly as I could, although as fast as she was moving it was difficult to maintain a normal “jacking” motion. “Aww yeah…jack me off…” Amy commanded, “And tell me before you start to cum…”

 

After a couple minutes of Amy slamming her ass down, (virtually impaling herself on my dick), having the butt-plug driven into my ass, and feeling Amy’s nice big dick in my hand I knew I was going to cream in the condom so I let the words escape, “Ames, I’m gonna shoot…” As soon as I said this Amy leapt from my lap.

 

I expected her to drop to her knees and begin sucking for her life, but she just turned around and said, “Not yet…has our purple friend got you ready?” I felt a little cheated, but I didn’t want to upset the girl who was making my dreams come true so I simply nodded. “Good, it’s my turn then…get on all fours on the floor.” I did as she said and not a second later she was on her knees behind me. Amy pulled the butt-plug from my ass and rammed it into her own as she whined with what sounded like pleasure mixed with relief. She wasted no more time as she reached back and pulled a condom from the paper bag. Immediately, the extra-large rubber was opened and on her sweet meat. Amy started rubbing her cock-head against my anus, and after a while I just wanted it inside me. Finally Amy took hold of my hips and forced her big member in my body. There was no slow stuff like when she first started riding me, I was being straight up fucked in the ass by the hottest girl in school…and I was loving it.

 

Karissa came slowly down the stairs and walked up to where I was getting hammered. “I think I’ll just lay down here.” She laid on the floor with her pussy right under my face, looked at me, and said “Do it, you know you want to.” Did I  ever! I dove forward licking and sucking everything I could get to. I buried my tongue deep in her pussy and licked like there was no tomorrow. I pulled my head away and took her left pussy lip in my mouth and sucked on it desperately. I then moved to the right and did the same. After I had had enough of her delicious lips, I pulled my head back, looked her straight in the eyes, and looked at her as if I was asking permission. “Yes, do it! Suck my clit!” she begged me. Who was I to deny such a sweet and innocent girl such a simple wish. I popped the small pink bud in between my lips and started sucking on it like a pacifier. “Fuck him Amy…pound him good…” Karissa moaned roughly.

 

Amy’s cock was sliding in and out of my ass and I was going wild on Karissa’s pussy. My dick was throbbing, so I took my left arm, keeping my right steady for balance, and started jacking myself off. Karissa was moaning desperately now, I knew she was getting close so I kicked my mouth into overdrive. Licking up and down her pussy frequently stopping to suck on her clit. The pussy in my mouth started convulsing and Karissa’s juices started flowing freely. I kept sucking her clit until she cried out, “Oh God…stop, stop, stop…I can’t take it anymore…” as she pushed my head away from her sweet spot. She laid their spent for a couple minutes as Amy fucked me relentlessly. Karissa slowly rolled over and crawled up to me face-to-face and grabbed my hair. She then pulled my head closer to her and started kissing me deeply. Karissa’s tongue darted around my mouth as she kissed me and Amy’s cock slid smoothly as she fucked my ass.

 

All of a sudden Amy pulled her dick out of my ass, stood up, and walked over to where I was kissing her sister. Karissa rolled the condom off her sister’s cock and grabbed its base. Amy said, “Deep throat it.” Karissa wasted no time, she plunged her head forward; instantly the 8 inch cock disappeared. My jaw dropped in amazement as she pulled her head back and thrust it forward once more. As Karissa deep throated the cock in front of her I leaned in and began licking Amy’s balls. As I was taking one at a time into my mouth and gently sucking on it Karissa was working her sister’s member like an expert.

 

Karissa pulled her head back to catch her breath and Amy’s dick bounced freely. I took this opportunity to slide the nice warm rod into my own mouth, and began sucking with vigor. I looked up to see Amy starring at me smiling. I pulled my head back so just Amy’s cock-head was in my mouth. I sucked on it hard before popping it out of my mouth, then sucking it back in. I repeated this several times and Amy’s smile widened as she started giggling. “You actually enjoy sucking me don’t you? I didn’t think any guy would ever wanna give me head,” she said laughingly.

 

I popped Amy’s cock-head out of my mouth once more and replied, “Well, what can I say? I just can’t control myself, you’ve got one delicious cock here Ames. I’ve been into shemale porn for a while, and I’ve imagined sucking a girls dick before…but I never thought it would be this fun.”

 

“I am so glad I found you…” Amy said, “You know, Jaymes only sucked my dick once, and I had to get him really drunk. He never let me fuck him either.”

 

I was a little surprised at this. Jaymes had been Amy’s boyfriend before he gone away to college that fall. I asked, “How did you get off then? I mean, if he never sucked you, and didn’t let you fuck him, did you guys have sex very much?”

 

“Well,” as Amy began speaking I felt breath on my cock and realized Karissa had gotten bored with the conversation and decided to busy herself. I felt Karissa bring my dick into her warm mouth as Amy continued. “We did fool around a lot, usually he would have me suck his dick for a while, then he fucked my ass until he was almost ready to cum, then I would finish him. Sometimes after he came, he would give me a handjob, but most of the time he would kiss me or play with my boobs while I jacked off. He always made sure he got off first though. Except for once, he had me jack off and cum in a glass. Then while he was fucking me he poured my cum all over my boobs and had me give myself a cum-covered tit massage.” She paused and then addressed her sister, “Karissa, when he cums don’t swallow all of it, save me some.” She responded with a muffled “mmm-hmm” before Amy went on, “Anyway, enough about him…I’m just happy I found a guy who not only sucks me off, but swallows my cum!”

 

Amy continued to giggle as I tossed my head back and enjoyed the sensation of my cock in Karissa’s mouth. “She’s good isn’t she?” I opened my mouth to answer Amy’s question but before I could she continued, “Wait Karissa, I’ve gotta better idea. You’ve got to let him fuck you…her pussy is so tight, it’s unbelievable.” Karissa let my dick slip from her mouth and rose to her feet. She walked over to the couch and laid down with her legs spread. I hurried over and got between those muscular tan legs, reached down, grabbed her ass, and lifted her pelvis up off the couch cushion, level with my cock. Amy was standing beside the couch and spread Karissa's pussy lips for me. I pressed the head of my member up against Karissa's opening, it was so wet and so hot I almost felt like I could blow my load then. I pushed forward with my pelvis and I began entering her. Amy was right, I had never felt a pussy so tight before. I pushed until I was about 1/3 of the way in, then I withdrew a bit and pushed back in, deeper this time. I continued like this until my cock was inserted to the hilt every time I went in. At this point I began thrusting harder and faster. As I increased my speed and force Karissa started to get more into it. “Pound her, just pound the slut. I want you to fuck my little sister harder,” Amy had long since removed her hands from Karissa’s pussy and was providing verbal encouragement.

 

Amy stepped up onto the couch with a leg on either side of her sister facing me. She inched closer to me, her cock bobbing in front of me was too enticing to pass up. I stretched my neck out so my extended tongue could reach her wonderful dick. I licked Amy’s cock-head while I fucked Karissa. Amy moved closer, I was then able to start sucking her properly. I closed my eyes and enjoyed the sensational feelings I was experiencing as my cock slid in and out of Karissa’s pussy and her sister fucked my face. I felt Amy’s cock as it filled my mouth and pushed down my throat when she would thrust forward. After several minutes, Karissa started breathing harder and moaning as her orgasm built. When she finally came she was almost screaming. The friction of the blonde’s pussy combined with her brunette sister’s cock was like heaven, but when Karissa’s pussy started to spasm I wished it would never end. The pleasure was too much though, and I felt myself getting ready to cum. I attempted to pull my head away from Amy’s cock to tell them I was close, but Amy had her hands on the back of my head and refused to let her dick leave my mouth.

 

Luckily for me, Karissa had become over sensitive after cumming and panted, “Amy…let him go…I can’t take any…more of this…” Amy released my head and withdrew her penis from my mouth. I slid my cock out of the tight pussy that I had been so enjoying and told them I was about to cum. Karissa immediately whirled around and engulfed my dick, trying to suck the cum right out. It didn’t take very long. I shot 2 or 3 shots in her mouth before she pulled it out and positioned it so that the next 3 or 4 shots landed on her face. She sucked the rest from my member and gathered all that she had collected in her mouth and gathered it on her tongue, which she stuck out for Amy and I to see. She drew her tongue back inside her mouth and swallowed. Amy sat beside Karissa on the couch and began licking and slurping the rest of my cum of her sister’s face.

 

I just sat and watched as the two sisters shared my cum and kissed. I was spent, and I knew I couldn’t go much longer. But Karissa and I had came twice, and Amy only had once, I knew that my work was not done. I turned my head from the beautiful sight before me to check the time, it was now 3:45 am. I was looking forward to the rest of the day.

"You are one very naughty school girl," Davey groaned, and closed his eyes and relaxed, content to let Michele have control of the situation.

Michele found this empowering. Most of the men she had had sex with in Chelmsford had forced themselves on her or forced her into capitulating. Even when she had been playing a dominant role with the Warden she was not really in control. Davey was showing her the utmost trust by just lying there and allowing her to take charge of situation. She found she genuinely wanted to please him.

Michele stroked and caressed Davey’s engorged member, sometimes slow and gentle, sometimes hard and fast. Davey expressed his appreciation with a contented smile on his face and with occasional moans of pleasure. He reached out and caressed her face with his fingers. Michele drew one of his fingers into her mouth and sucked on it; twisting her tongue around the digit.

Davey put his hand under Michele’s chin and gently bought her face to his. He looked longingly into her eyes and said,

"You are truly beautiful Michele," and then bought her mouth to his and kissed her tenderly.

The smokiness of the scotch they had drunk earlier had mixed with his sweet breath and she responded to his kiss. She kissed him harder and her hand started pumping his long hard cock in a steady rhythm.

Davey groaned again in the back of his throat and Michele gently lifted her lips from his. He sighed his disappointment; but not for long. Michele slid her stockinged knees along the floor so that she was positioned adjacent to his crotch. She lowered her head and kissed his cock. She kissed it all over leaving telltale smudges of lipstick on the shaft and head. She rubbed it against her cheek and placed the glans against her eye and batted her eyelashes teasing him with ‘butterfly’ kisses.

Michele was totally in control of the situation and was actually enjoying what she was doing to Davey. Not only did she feel empowered, she felt aroused; for the first time since she had been forced into becoming a transvestite she totally loved being a woman and pleasing her man.

She bought her mouth down to Davey’s scrotum and kissed and licked his balls, feeling him tense up and sigh at this new attack on his senses. Then she licked all along the length of his penis and finally took his member inside her mouth. She ran her tongue all over his glans as she commenced to gently suck and move her head up and down.

"Oh Michele you are wonderful," Davey whimpered.

"But take it easy I’m so close," he half complained.

Michele had no plans to take it easy; she was in control and wanted to make Davey climax. In her head she imagined him coming; then they would cuddle and caress until they were both sufficiently aroused and he would make love to her like a woman. She could hardly believe her own feelings but she wanted Davey to fuck her. My god she was changing! She examined her feelings and found that yes; she loved being a woman with Davey and she wanted Davey to want her. She didn’t try to analyse her feelings any further; she was too confused, she got on with her most immediate pressing need; to please Davey.

Michele clamped her lips around Davy’s now throbbing member and sucked hard and bobbed her head up and down as fast as she could. Davey started to convulse and Michele tasted the first beads of pre-seminal fluid and then the hot jets of his seed as his penis convulsed and shot streams of warm salty sperm into her mouth.

Michele kept up her hard and fast fellatio, swallowing his issue as it filled her mouth. In response to Davey’s climax she felt her own clitty harden in the silken purse of her panties. Slowly Davey started to relax as his orgasm subsided and Michele felt his organ begin to slowly deflate in her mouth. She took it out and rained kisses all over the cute member as it shrank back into flaccidity.

Davey reached out and gently assisted Michele up onto the bed so that she was lying beside him. He gently stroked her hair and softly kissed her.

"I think I’m falling for you Michele," he whispered in her ear.

"I think I’m falling for you to Davey," she whispered back and snuggled up closer to him.

They caressed and chatted easily with each other for a while until eventually they fell asleep in each others arms; like lovers.

Then – Crash! The door to the cell flew open and Eddie strode into the cell. Michele and Davey sprang to their feet; Davey taking a step forward in a defensive position to protect Michele.

"Just look at these two lovebirds would ya!" Eddie sneered sarcastically and reached for the scotch, gulping down a swallow.

"Fuck me Davey, I warned you about this bitch!" Eddie whinged.

"She’s fucking trouble mate; I don’t care what she’s done or said to make you all gooey over her. She’s more fucking trouble than she’s worth."

"If I could sell the bitch for a profit I’d get rid of her, but I ain’t even made the money I invested in her," Eddie went on, waving his hand at Michele as if she was just a commodity not worthy of consideration.

"She’s wonderful Eddie," Davey shot back.

"You just don’t appreciate a precious jewel when it’s staring you in the face," Davey continued.

"And I want her!" Davey demanded in a menacing tone.

Michele was stunned; she couldn’t believe what she was hearing. Was Eddie’s best friend and business partner prepared to take on Eddie over her? She felt flattered but at the same time confused.

"If she wants me that is?" Davey looked deep into Michele’s eyes with a questioning look.

Michele was now totally confused. She knew that prisoners kept transvestite inmates as ‘wives’; in fact some of Eddie’s ‘girls’ were ‘married’ to inmates but continued to work in the brothel to provide money for their ‘husbands’. The more privileged inmates, the ones who really ran the jail, had full time transvestite partners; wives, who ‘stayed at home’ and lived with them in their cells.

"You’re fucking joking aren’t you Davey? You ain’t going to let this big arsed bitch get in the way of our friendship are you?" Eddie sounded astounded.

"No I’m not Eddie," Davey replied, "If she wants to move in with me I’ll see you right, but she stays with me; exclusively!"

"But only if that’s what she wants to do," Davey added this time turning to Michele and taking her hands in his and looking deep into her eyes.

Michele felt completely feminine; at that moment the remnants of her male alter-ego ‘Mike’ disappeared. She was a woman who wanted the man standing before her. She tried rationalising her feelings; being Davey’s concubine was a better prospect than being forced to work in the prison brothel; but deep inside she knew it was more than that. She had become Michele; she was Michele, and she wanted to be Michele all the time, and to be with Davey.

"Yes Davey," Michele’s whisper was barely audible, "take me home please; take me away from this place."

"Oh you fucking dopes," Eddie laughed.

"She is going to cost you heaps Davey," he warned; "You’re not getting her off me for nothing!" he insisted.

"Eddie you’re my best mate in this place and we go back a lot of years; we scratch each others backs and work the joint for a share of the profits; but if you keep talking about Michele like that in front of her I’ll fucking well smack you!" Davey retorted angrily.

Eddie laughed, "Ok, ok, don’t get your knickers in a twist! She’s yours; we’ll settle the price later."

"Michele, go and see Charlotte and Mabel and get them to move your things out of here into Davey’s cell in A block; I’ll clear the move with the warden tomorrow." Eddie said.

"And as wedding present you can keep the clothes, wigs, shoes and the rest of the stuff I bought you free of charge. I hope you will both be very happy," Eddie said half sarcastically.

"Now run along girl; me and Davey have business to discuss," he ordered.

Davey reached out and kissed Michele gently on the lips, "Don’t worry about him honey," he smiled; "get out of here and I’ll meet you in my cell in a couple of hours."

Michele walked out of her workroom for the last time that evening and didn’t bother to look back. She found Mabel and told her Eddie’s instructions. Mabel didn’t believe her at first and ran down to Michele’s workroom to see Eddie. She came back flabbergasted.

"Well I’ll be fucked," she said, "Good on you girl; now get out of here and me and Charlotte will bring your things down to A block," she smiled good naturedly.

When Davey finally completed his business with Eddie that evening he was considerably out of pocket. Michele had cost him plenty but he smiled as he walked back to his cell, two minders at his side, she was worth every penny. Besides he would soon make his money back with his other business dealings with Eddie; they both made more money than they could spend in this shithole. The only thing his money couldn’t buy was freedom; he had many years left to serve; but at least he would be happy and contented with Michele by his side.

Davey arrived at his cell just after midnight. His cell was actually three cells combined into a living area with all the modern furniture and electrical gadgets you could want, and a large bedroom with an enormous bed set against one wall. As he closed the door to his cell he noticed all the lights were out and the place was completely dark except for the flicker of candlelight coming from his bedroom. Davey stripped naked, kicked his clothes aside and strode towards the bedroom.

Michele was lying on the bed; surrounded by deep red satin sheets, her head resting on a mountain of white satin pillows. She was exquisite! Her hair was a sea of raven curls hanging down to her shoulders and her dark, heavily made-up eyes shone brightly beneath the fringe. Her full mouth a ripe red plum waiting to be kissed, and her rouged cheeks emphasised her sharp cheekbones and the elegant lines of her pretty face.

She wore a full length white silk nightgown thrown open and spread out on the bed like angel’s wings. A matching white bustier adorned her body, the garter straps clipped to white nylon stockings. He could just make out the triangle of white satin panties between her legs which were slightly spread apart; her feet were shod in white open-toe high-heeled sandals, her toes peeking out of the high-heels, her white stockings gossamer thin and stretched taught over her red painted toenails. She wore a pearl choker necklace, matching earrings and bracelets. She held out a hand and beckoned.

Davey strode towards the bed, his manhood erect before him, a rope of gleaming, clear pre-seminal fluid leaked from the eye, and Michele reached out and took him in a firm grip and pulled him onto the bed. She opened her legs wide and he knelt between them; neither of them saying a word. He bent down and kissed her passionately on the lips and she responded and moaned deep down in the back of her throat.

She still held his manhood in a firm grip as she slid herself underneath him and eased her panties aside with one hand and positioned his member at the entrance to her special place. She lifted her white nyloned legs up high and bought her calves up around Davey’s lower back so that her high-heels were high in the air and almost touching. Michele pulled up her lower body and at the same time guided Davey’s beautiful hard slick member inside her. They never stopped kissing. Michele rose up and locked her heels behind his back as Davey thrust forward so that she could force all of him inside her. They rode the waves of mutual pleasure slowly; Davey taking his time so that Michele’s orgasm would come at the same time as his.

He released streams of his hot seed deep inside her and she responded by rising up and holding him tightly against her as she emptied her own emission into her white satin panties. Michele could feel Davey’s hot spend lubricating his throbbing glans as it stimulated the sensitive organ deep inside her. Davey could feel Michele’s secretions saturating her panties, soaking through, warm and sticky against his lower belly. Their lips had never parted throughout their lovemaking. Davey begrudgingly drew his face away from Michele’s just far enough so that he could look adoringly into her pretty blue eyes.

"I love you Michele," he whispered.

"I love you too Davey," she whispered back. Michele smiled.

 

The End

 

 We talked for a good while on yahoo messenger (like 3 or 4 months) and one day we both had our web cams on and started talking dirty and things got heated between us…very heated. As she talked about kissing her way down my body licking my chest and stomach as she went then unzipping my pants and pulling out my dick and sucking it till I shot all in her mouth……well that started make’n my 8 inch cock really stiff. Then I replied by telling her I would kiss her deeply then tear off her cloths and lick her tits and as I kiss and lick her body I would stroke her cock, then kissing my way down and sliding my tongue down her body and over her cock and balls and not stopping till my tongue touches her hot ass hole. She type that I had turned her on and made her want me….so I said well lets fuck on cam and she quickly replied yes. We both striped and her nice smooth slim sexy body laid on her bed rubbing her self all over softly stroke’n her cock and rubbing her tits as I stroked my dick I type’n to her that I wanted to fuck her so hard. She said well I guess I’ll pretend this is you…..as she pulled out a nice sized dildo about 7 inches maybe and she started sucking on it and rubbing her balls and ass at the same time. I jerked my dick looking at her sexy body as she sucked her dildo, then she moved it down to her ass and pressed it against the hole and slid it in and I could tell by her face she was moaning deeply. My cock got even harder when she started fucking her ass with that dildo she sat up and started bouncing on it as if she was ride’n my dick and I felt like I could explode already from be so turned on, but I kept stoke’n holding back my load. She started bouncing faster and faster then I saw her scream out and cum shooting out of her dick as she fucked that dildo wildly….as I saw that I started stroking faster and faster then shot my load all over my stomach and hands…….well cleaned up then started talked about her moving here to the U.S. since we had been talking for so long and just had a great session of cyber sex, we talked long about it and decided that she would move here and live with me in 2 weeks.

 Those 2 long weeks almost every night I dreamed about me and her make’n love and going out to places but before I knew it the day was here I had to pick her up from the air port. As I drove to the air port many things of what I should do when I see her ran through my head. As I was waiting for her to come through the doors I thought that I would grab her and kiss her deeply, and then there she was walking to me she ran and jumped into my arms and we kissed make’n out for about 10 minutes at least haha…..On the drive back to my house we talked and as we talked I noticed that her skirt she was wearing had slid up her leg a bit and I just could resist rubbing that oh so sexy leg, so I did and she looked at me and we saw in each others eye what was to come when we would get home. As soon as we walked through the door I was carrying her bags and she walked in front of me I dropped the bags and shut the door grabbed her spun her around and lifted her around my waist and pressed her aginst the wall kissing deeply I rubbed her ass and she started taking off my shirt and I let her down tore off her shirt and slid her panties down and she pulled my shirt and pants off then slowly took my dick head into her mouth and slowly started sucking me and it felt like nothing I had ever felt before it was amazing and I rub and grabbed her hair as she lick and slurped my cock. She stopped and with only her skirt still on she walked over to the bed room and called me with her finger and walked in an laid on the bed,  I quickly followed her and she laid now completely naked with her legs spread and I came to her dropped down and started licking her ass hole slowly and deeply as she moaned and called for me grabbing my hair and the sheets I stroked her dick as I ate he hot ass she told me to suck her before I fuck her so as I took her cock into my mouth I pushed my index and middle finger into her ass she gasped and moaned as I fingered and suck her. I stopped lifted and pressed my dick to her hole and slide it in slowly and she looked at me moaned telling me to make love to her so I bent down and laid on top of her and kissed her as I worked my dick into her she gasped and moaned as we kissed I slowly moved in and out of her swirling my hips as I glided my rock hard dick in and out of her. After a few minutes of making love to her she said I was make’n her even hotter as I worked her then she bit my lip and rolled us over and at my surprise she still had me in her and she started rolling her body make’n her ass move in a way that felt so good I could feel my cum boiling in my hot balls, she asked me if I liked that (I replied with a kiss and yes) and then she pressed her hands on my chest rolling her ass moaning….softly saying my name tell me she loves my cock, I told her that her ass felt amazing and she then stopped and sat up and started bouncing  up and down now screaming as she bounce I rubbed her body and tits, then started stroking her dick make’n her moan and scream more. I stopped her bouncing and started thrusting up into her make my hips slab her ass she now screaming my name and telling me harder that she is about to cum, I then grabbed her hips and as I started thrusting up I made her body bounce up and down she is scream as we sweat and moan kissing and biting each others lips, she screams that’s she is going to cum and as I lay there I stop and she sits all the way down on me I starts jerking her and she shoots all over my belly and chest after she cums she slowly swirls her ass around and scoops up her cum on her 2 fingers and puts it to my mouth so I start licking and suck her finger swallowing her cum (I never tasted cum but when I licked hers it tasted of a sweet nectar) as she grinds on my dick I tell her that I want her to swallow my cum too and she simply nods and lifts off and I get of the bed now standing and she lays on the bed and pulls my cock into her mouth sucking it deeply and rubbing my stomach and balls looking at me and asking if it feels good and I moan and rubbing her head telling her yes and that I love when she sucks me. I tell her that I’m about to cum and she opens her mouth and stokes my dick until I bust my load all in her mouth as I cum she starts sucking me again swallowing all of me then I lay down beside her kissing her as we rub each other all over tell that we love each other and then drifting asleep naked holding each other.

*If I Get good comments on this and good review I will post more about this topic*

<!--[if !supportEmptyParas]--> <!--[endif]-->

All of a sudden I heard the door open, it was Kim and she saw what I was doing.  I told her to not tell anyone.  She said,   “So you like chicks with dicks huh, you little slut.”  She had a weird smirk on her face as if she was going to blackmail me.  I said, “Lets just keep this a secret between you and me”  She locked the door behind her and slowly started walking towards me.  I could see her eyes focused on my boner, my heart was racing. “Kim, please…” I said, but she just put her finger over my lips to tell me to keep quiet.  She slowly leaned over and kissed me.  It had always been a fantasy of mine to fuck her, it was as if my dreams were coming true.  She took my hand with both of her hands and put it on her chest.  Slowly, she slid it down to her crotch and slipped it in her pants.  Before I knew it, I had a hand full of penis.  My blood rate shot through the room.  “You want some” she said.  I replied, “I want the whole thing,”

<!--[if !supportEmptyParas]--> <!--[endif]-->

I went and sat on the bed, stroking my dick to keep it hard.  Kim took off all of her cloths, I finally got a view of her penis.  It was a good 10 inches long.  I layed down on the bed, and she layed right on top of me in a 69 position.  I sucked her dick like there was no tomorrow.  The smell of her ass was nasty, but in a way it smelled good.  She then got up and said, “You’re my bitch tonight”  I put my legs over her shoulders as she got behind my ass.  Slowly I could feel her dick penetrating me.  My dick got rock hard instantly.  She got her hand and began stroking my dick.  She was thrusting in and out for the next 5 minutes.  It was heaven on earth, it was the greatest feeling in the world.

<!--[if !supportEmptyParas]--> <!--[endif]-->

I couldn’t hold it in any longer, and a giant shot of cum shot straight up and landed on my chest.  After 4 more shots of cum pooling on my body, it stopped.   Then Kim screamed, “I’m gonna cum…” and took out her dick and put it over my face.   I opened my mouth wide and closed my eyes.  I could feel shots of cum hit the back of my mouth.  A few seconds later, my mouth was full of her cum, and I swallowed it all.  As I lay there, she started licking the cum from my body.  When it was all cleaned up, she put her hand behind my neck and raised my head to kiss me.  I could feel her tongue as she was spitting the cum into my mouth.

<!--[if !supportEmptyParas]--> <!--[endif]-->

At the end, she rolled over and lay next to me. “Next time, your on the bottom” I said.  And she replied, “Yea, wait till you meet my friends”  My dick rose up again, I couldn’t wait for the next day.

"That was some performance there Michele; for a girl who only sucked her first cock a few hours, ago you sure learn fast," he said.

Ellie took her face out of the cop’s lap and turned her head towards Michele.

"See, I told you that you would probably end up liking it didn’t I," she gloated.

The fat cop pushed her face back down on his stubby cock."

"Shut the fuck up and suck my cock bitch," he laughed, "You let those other boys worry about her; you just take care of me."

The fat cop screwed up his eyes and reached down with both hands to push Ellie’s face onto his penis. He bucked in his seat and face-fucked Ellie with short hard strokes. Ellie was working hard at sucking his member and Michele could distinctly hear the sucking and slobbering noises Ellie made as worked on the cop’s cock. Ellie was rocking on her knees, the toes of her black high-heels dug into the cheap carpet, her short black dress had ridden up at the back revealing her white satin panties and matching suspenders clipped to the gauzy taupe stockings encasing her long sleek legs. She looked very sexy. Slutty, but definitely sexy.

Michele felt her penis begin to harden in her sticky panties. She couldn’t believe she could become aroused again so soon after her last orgasm! The sight of Ellie fellating the fat cop was also having its effect on Steve, Joe and Bill; Michele noticed that they were also in various states of arousal.

Joe sauntered over to where Ellie was fellating the cop.

"Mind if I use the other end?" he sniggered at the fat cop.

"Do what you like with her Joe; just so long as she doesn’t lose her rhythm," he laughed back.

Ellie didn’t even flinch; she just carried on sucking away on the cop’s stubby cock. Joe grabbed Ellie’s high-heels and spread them apart, her stockings rasping on the cheap dirty carpet. Joe positioned himself between Ellie’s sleek nyloned legs and took hold of his cock and began to rub it in the cleavage of Ellie’s satin pantied buttocks.

Michele felt her own cock harden and then she became aware that Steve had slid his member into her loose fingers; without conscious thought she gripped the thickening member and began to stroke it. She was mesmerised by what was happening across the room. Bill shifted to the other side of Michele and put her hand on his cock. Michele lay there masturbating the two men while the three of them watched Ellie suck the fat cop while Joe rubbed his cock on her panty clad arse.

Joe reached down and slid the silken gusset of Ellie’s panties to one side and exposed her puckered sphincter. He wet his finger with his tongue and probed at the wrinkled crack. Ellie kept fellating the cop but she also pushed back with her body and Michele watched fascinated as Joe’s finger disappeared inside Ellie’s anus.

"God that looks good," Michele whispered.

Bill heard Michele and took that as his cue. He moved down the bed and slipped his hand under Michele and gently eased her over on her side. She could still see Ellie and the two men across the room and she was still wanking Steve’s hard shaft. Michele didn’t take her eyes off the trio across the room even as she felt Bill slide his hand under her nylon panties and insert a finger inside her semen lubricated passage. She gripped Steve’s cock harder and wanked away at it.

Joe removed his finger from Ellie and spat into his palm then rubbed the spit on his member. He positioned himself directly behind Ellie and nestled the glans of his penis against her sphincter. He reached down and gripped each of Ellie’s silken stockinged thighs in each hand and began to push. He groaned as Ellie pushed back against him until his belly was hard against her bottom and he was buried in her to the hilt. Ellie wriggled her skewered arse and began to suck harder at the fat cop’s stubby member.

Bill rucked Michele’s black leather mini up around her waist and moved down the bed and knelt beside Michele’ pantied rump. He pulled her panties down, the nylon material of her panties whistling on her hosed legs, and left them around one slim ankle. He pushed Michele over further and lifted her leg so that she was lying on her side with her legs scissored open. Bill lay down behind Michele and put his rock hard cock at the entrance to her back passage. He pushed and Michele groaned at the pain as Bill’s glans forced open her tight sphincter.

"Easy honey," Bill whispered into Michele’s ear and the nuzzled her neck, "just relax and it will slide right in; Steve’s already lubed you for me."

And it did! Michele relaxed and then felt Bob’s hard cock slide right up inside her. She was still fascinated by the other trio having sex across the room but she was now very aware of Bill’s body rubbing against hers and his grunts and groans as he fucked her. She loved the feeling of her anus being filled and the shivered with pleasure as Bill’s cock rubbed against her prostate.

Steve had now moved to the edge of the bed and was watching the sex going on around him as he slowly stroked his own cock.

Joe was pounding himself in and out of Ellie; he had moved his hands down to her feet where he gripped her high-heels and rode her like a sleigh. Ellie was a lovely sight to behold with her black chiffon dross rucked up around her waist, her gossamer taupe stockings clipped to her white satin suspenders and her matching satin panties, the gusset eased aside to allow Joe access to her arse. Her pretty face was buried in the fat cop’s lap, sucking his engorged manhood and she bucked back and forth on her knees keeping rhythm with Joe’s pace as he fucked her. Joe was groaning and moaning and the fat cop had his eyes screwed shut and pushed Ellie’s face down into his lap. They groaned in unison.

"I’m coming; oh god I’m coming!"

Michele felt Bob quicken his pace as he hung on to her and pounded his cock in and out of her come slicked anal passage. Michele pushed back against him and wriggled her bottom. Lying on her side like this she was unable to thrust back and forth but her wriggling and pushing caused the glans of Bob’s penis to massage her prostate gland bringing her closer to orgasm. Bob suddenly wrapped his arms around Michele and pulled her back hard against him and Michele felt his cock begin to shudder as streams of hot semen flooded her anal passage. Bob’s manhood spasming against her anal gland caused Michele to climax too and she wriggled her bottom and pushed back against Bob as she shed her spend into her already come-sodden panties.

Steve spun around on the bed and aimed his cock at Michele’s heavily made up face. He groaned and shot stream after stream of hot semen over her face, rivulets of his juice ran down over her eyes, nose and on to her lips. Michele gobbled the salty offering, slavering the fluids with her tongue and licking it into her mouth as her own orgasm shot through her anus, testes and penis. She was experiencing one of the most intense orgasms of her life.

The fat cop pushed Ellie’s head down into his crotch and held her there as he came, he bucked and squirmed in his seat as his emission erupted out of his throbbing cock and deep down Ellie’s throat. Ellie wriggled and struggled tried to pull herself free to prevent herself from drowning on the fat cop’s semen. Joe used Ellie’s struggles for his own gratification and plunged his turgid penis deep into her pulsing anal channel and expended his load, flooding her with a deluge of hot semen. Ellie was nearly asphyxiated when her own orgasm ripped through her and she flooded her panties, a wet stain spreading across the front panel of the white satin garment.

Everyone in the room had climaxed almost simultaneously and they all fell apart and gasped for breath as they came down from their respective orgasmic highs. Ellie was sprawled on the floor heaving in deep breaths. Between her gasping breaths she guzzled the remainder of the fat cop’s spunk. She pushed herself up on her knees and reached up and slapped the cop playfully across the face.

"You bastard," she wheezed, "I know we have played at erotic asphyxiation before; but not when I’ve had a big cock inside me at the same time!"

"Fuck it was incredible though," Ellie smiled and turned around and kissed Joe passionately on the lips.

She looked across at Michele,

"Well was I right or was I right?"

"I told you most of the girls eventually like what they experience here; and I just knew you would be too much of a slut not like it too."

"When our friend in blue here," Ellie nodded at the fat cop, "told us that you had continued on to the party after he made you suck his cock in that parking lot; we knew you would eventually become a willing participant in our little orgy."

Michele was still catching her breath and doing her best to wipe Steve’s coagulating semen off her face.

"Well I’ll tell you what Ellie; you’re a arsehole at work and you’re a cunt of a friend outside of work. But if you ever plan another orgy like this; you better count me in" Michele replied, a smirk breaking out on her face.

Everyone in the room burst into laughter.

As Michele drove back to her sister’s house in the early hours of the morning she pondered on the previous evening’s events. Michele’s sister Angie had revealed that she knew her brother Malcolm (Michele’s alter ego) was a closet transvestite (and seriously hinted that she herself was a lesbian!). Michele’s workmate Jill had let Malcolm make love to her whilst he was dressed as Michele; and Eddie had turned out to Ellie, the most perverted transvestite you could imagine!

Michele had fucked and sucked and been fucked and sucked and had totally fallen in love with the secret underworld of transvestite sex. Ellie had said she would arrange another transvestite and admirer party for the following weekend and Michele was already planning what to wear. What a marvellous twenty-four hours it had been!

When Michele arrived at her sister’s house it was dark and totally silent. She let herself in and staggered to the spare bedroom, shucked off her semen encrusted clothing and wig and fell into bed without even bothering to clean off her makeup. She fell asleep immediately and didn’t wake up until late Saturday afternoon.

Malcolm woke up to find Angie sitting on the end of the bed with a cup of hot steaming coffee in her hand.

"Drink this, shower, shave, brush your teeth, and then come and tell your older sister all about your evening, oh brother of mine!" Angie giggled.

"From the mess your clothing was in you certainly got up to something exciting," she went on.

Malcolm looked groggily around the room.

"Where are the clothes I wore last night," he asked inquisitively.

"Cleaned, pressed and waiting for when Michele re-appears. I even washed, blow dried and brushed your wig," Angie replied.

"In fact after you have cleaned yourself up; why don’t I help you transform yourself again. Yesterday was fun and I’m sure you learned a lot," she smiled.

"I don’t know? I feel kind of weird letting my sister dress me as woman and do my make up," Malcolm frowned.

"Oh fuck that! I know you liked it; now get up and get yourself sorted and meet me in my bedroom. Once I've transformed you into ‘Michele’ I'm sure you will feel more comfortable about telling me all about what happened last night. Let’s just call it ‘girl talk’," she winked, and then got up off the bed and left the room.

Malcolm did as his sister bid and brushed his teeth, showered and shaved. It took a while to remove the caked-on makeup that he had not removed before going to bed but liberal use of moisturiser removed most of it. He was wondering what his sister was getting up to, wanting to help him dress again. The last time she did it, now nearly two days ago, she had put her hand under his skirt and touched him through his panties. What was that about?

Malcolm had been crossdressing for so long now that his mind automatically switched from thinking of himself as Malcolm to Michele as soon as he began to transform himself.

When he came back into the bedroom wearing only a bath towel around his waist he found Angie sitting on the bed surrounded by a selection of feminine clothing, most of which Michele had worn the previous evening. It was now cleaned and pressed. A packet of Kaiser Ultra Sheer stockings replaced the laddered and come-spattered hose he had worn home. Michele’s wig and makeup were arranged on the dressing table.

Angie was wearing a pleated navy blue skirt that came to just above her knees. She wore a white satin blouse that exposed her cleavage, navy-blue high-heels and sheer tan hosiery. She was also wearing full makeup and jewellery. She looked quite hot for a woman of her age.

"Where are you going dressed like that?" Malcolm asked.

"Nowhere. I’m going to help transform you into Michele and then we are going to discuss what happened at the party," Angie answered walking over the dresser and patting the chair, indicting Malcolm should take a seat in front of the mirror.

"You do your makeup this time and I’ll only help if you need me to ok?" Angie said.

"Ok," Michele replied, taking off her towel and sitting down at the dresser completely nude.

Michele’s finger and toenails retained the two coats of glossy plumb red that she had applied on Friday afternoon so they only needed touching up where the nail polish was chipped. She applied a thick coat of foundation to her face and then set it with matching face powder. She brushed dark blue eyeshadow onto her eyelids and then applied a coat of pink out to the far corners of her eyes, lightening the makeup and blending the two shades. Next she applied jet-black eyeliner to her upper and lower eyelids, applying three coats and touching up here and there when Angie directed her.

"So far so good Michele," Angie cooed, "But of course you’ve had years of practice you naughty closet queen," she giggled.

Michele applied thick black mascara to her upper and lower eyelashes, and then blush to her cheeks, feathering it along her cheek-line and smoothing it up so that it almost merged with her eyeshadow. Then she dusted her whole face and neck with a coating of sheer-glow finishing powder, being careful not to smudge her mascara and eyeliner.

She painted on the base coat of the two-coat plum coloured lipstick just like she had been taught by her sister, being careful not to smudge her lip-line applying the clear top coat over the base colour coat.

Michele positioned the wig on her head and adjusted and brushed it until it was sitting perfect with the fringe straight.

Michele had again made the transformation from a plain, smooth-faced man to a heavily made-up middle-aged whore with brunette hair framing dark exotic eyes, rouged cheeks and seductive red lips.

She turned towards her sister, who looked at her critically and said,

"Wonderful Malcolm; you have again transformed into Michele," Angie said and stroked Michele’s face gently with her long red fingernails

"Let’s see you get dressed then," Angie said, helping Michele to her feet and leading her over to the bed.

Angie patted Michele playfully on the buttocks.

"You look good enough to eat," she laughed.

Michele was again confused by her sister’s actions.

"Angie," she whispered, "are you some kind of a lesbian or something?"

"I’m an ‘or something ok’?" Angie answered.

"I like men; no I love men; but I like certain kinds of women too."

"I’m bisexual I guess. I’m a lipstick lesbian."

Michele looked at her sister confused. Angie went on,

"I like to have sex with feminie women; not the hairy ‘man-hater’ type of lesbians that are often the stereotype. Do you get what I mean?" she finished.

Michele nodded and sat down on the bed and started getting dressed.

She slid into the red lace suspender belt and adjusted it so that it sat around her waist and then took the stockings out of the packet and slipped the hosiery over her pretty painted toes and slid the sheer nylon up her legs. She clipped the stocking-tops onto the garters hanging from her suspender belt. She carefully straightened the back-seams keeping the nylon taught; smoothing out the wrinkles as she went. Next she slid the red satin bikini panties up her nyloned legs and pulled them snug around her buttocks and crotch.

Michele hooked the red brassiere around her chest stuffed the cups with the old pairs of pantyhose that she had used to fill them with before. She stood up and stepped into her black leather mini and adjusted it at her waist ensuring the hem was nice and straight at mid thigh. Next she pulled on the leopard-skin nylon blouse, buttoning the blouse and tucking it into her skirt.

Michele walked back over to the dresser and sat down. She clipped on the silver mounted ruby drop earings clasped the matching necklace around her neck and the matching bracelets on both of her wrists. She slid the four large silver rings on her fingers, two on each hand. Michele bent down and slid her feet into the black leather high-heeled sandals; buckling the thin straps which came to just above her ankles. She sprayed a liberal amount of ‘Poison’ perfume all over finishing with a quick spray under her skirt.

"There; transformation complete," Michele turned her pretty face up to her sister’s.

"Not quite," Angie said and kneeled at her brother’s feet.

"You forgot this," she said fastening the silver anklet below Michele's left ankle.

Michele felt her penis stir as her looked down at her sister’s attractive face so close to her crotch and felt Angie’s slim hands slide over her stockinged ankle. She wondered what was going on here between her and her sister.

Angie slid her manicured fingers up Michele’s sleek leg and her hand disappeared under the black leather mini. Her fingers stroked the naked skin above Michele’s stocking-tops and she looked up at her brother.

"Come on Michele, sit next to me on the bed and tell your sister all about what happened to you last night," Angie said removing her hand from under Michele’s skirt.

Angie stood and helped Michele up on her high-heels and led her to the bed. They sat side by side close to each other and Michele began to tell her sister the full story of what had happened from the minute she had left her Abgie’s house for the party yesterday, until she returned in the early hours of this morning. Angie hung on every word.

"Absolutely fascinating Michele," Angie said.

"I wish I had been there! But you must have been quite scared when those guys had you tied to the bed like that. Men can be such pigs sometimes," she said, and put her arm around Michele.

Angie looked into Michele’s pretty painted eyes and Michele stared back into Angie’s heavily made up face. She hadn’t before realised how sexy Angie looked when she was dressed and made up like this. Angie moved her head forward so that their faces were only centimetres apart and parted her red lipsticked lips. Michele felt her cock harden in her panties.

"Angie; we shouldn’t. We’re brother and sister." she whispered.

"We’re Angie and Michele," Angie responded and kissed Michele deeply, their lipsticked lips mashing together and their tongues intertwining.

Michele gently pushed Angie away and stood up on her high heels, her hard cock tenting the front of her skirt.

"It’s incest Angie; it’s wrong," she whispered.

"As far as I’m concerned you are Michele, a hot fuckable woman who happens to have a real penis instead of a strap-on; not my brother Malcolm!" Angie replied.

"You’re no different to all the other women who I have fucked over the years," she went on, "and I can see you like what we are doing," she said pointing to Michele’s erection visibly tenting her leather miniskirt.

"Wouldn’t you like some this," Angie said and lifted her skirt.

"I expect you’ll be very busy indeed," Eddie’s laughter faded as he disappeared down the corridor between the cells.

I cringed at the thought of another night in this caged prison brothel, forced to service some of the roughest men I had ever met. At the same time I was feeling confused as to how quickly I had acquired female mannerisms; how I had become aroused by wearing the lingerie, makeup, wigs, and heels that Eddie forced me to wear. I was also amazed at how, after only a brief introduction, I was developing the skills of the feminine art in applying makeup.

I was more disturbed however, by how I had responded to the sexual attentions of some of the punters and the ministrations of my crossdressed sisters. I could not deny that, despite the fact that during this torrid night I had been repeatedly orally and anally raped, I had experienced two of the most intense orgasms of my life this evening. I decided that I was just too dog-tired to think about it; I needed to sleep. I was even too tired to be angry with Charlotte and Carmel, who although they had obviously enjoyed the sexual encounter we had just experienced together, had obviously been put up to it by Eddie so that he could enjoy the ‘all girl’ show.

The two vixens in question, (who had just introduced me to my first transvestite lesbian experience), slunk out of my workroom cell. They both glanced back and blew me a kiss.

"Nightie-night sweetie," they giggled in chorus, the sound of their laughter and the clattering of their high heels diminishing as they moved on down the corridor.

Mabel came in and dumped my prison fatigues on the bed and pointed to the door with the words,

"Out! Shower. Get changed!"

I got the message and slipped out of my feminine attire and deposited it in the laundry bin in the corner of the cell. My heels and breast-forms went inside the large wardrobe. I removed my wig and put it on a vacant wig-stand then took the towel Mabel proffered, cinched it around my waist, and headed once again down the passageway between the cells carrying my fatigues to the shower block.

The overhead lights suddenly clattered on revealing the workroom cells on either side of the passageway. Through the open bars I stared at the oversized double beds, rumpled satin sheets, large armoires and dressers with makeup mirrors, totally incongruous in this disused prison wing. The workroom cells were like islands of perfumed femininity amid a sea of stink created by caged men.

Mabel poked her head out of my cell and barked orders to a couple of prisoners who I recognised as weaker individuals who had ‘no muscle’ and therefore had shitty jobs working in the prison laundry. They were stripping the beds and dumping sheets and pillowcases into large wheeled washing carts. They were also emptying the laundry bins from each cell into individual oversized prison laundry bags; I noticed the laundry bags were each labelled with the cell numbers and the feminine names of the ‘working girl’ that used each cell. As I passed one of the laundry hands I saw him bring a pair of soiled panties to his face and rub the bulge in the front of his denim jeans. I scurried past disgusted.

The laundry was a big money maker for the prison. It catered for the needs of the prisoners, the guards, and also took in work from nearby hotels and a hospital. Eddie controlled the prison laundry, as he did just about everything in Chelmsford prison. Obviously also had the laundry workers working overnight to wash and dry the bedclothes and clothing that belonged to his ‘working girls’. To make his prison prostitution operation work he must also have the laundry dry cleaning service clean the ‘girls’ skirts, blouses, jackets and other items of clothing.

The cleaning of feminine clothing had to be being done overnight as I had made many trips to the prison laundry during the day whilst working as Eddies accountant and I had never seen any items of female attire in there. I knew Eddie made a considerable amount of money from the laundry; and of course, he was paying off someone high in the prison authority so that he could run the laundry business. As his accountant I knew he would also be charging the ‘girls’ for the laundry service; Eddie made money off everything, he gave nothing away.

When I got to the shower block I ran the water as hot as I could get it and soaked myself for half an hour in the shower trying to wash away the shame and humiliation of the last few hours. I scrubbed my face repeatedly to remove the caked on makeup. The blush, lipstick and eye shadow came off easily but I had to scrub at my face continually with the washcloth until it came away bearing no traces of foundation or mascara. I poured nail polish remover onto a cloth and cleaned the red nail polish from my fingernails.

I moved to the mirror and was glad to see that I looked like a man again; but then I noticed that some mascara was still clumped here and there on my eyelashes and little clots of eyeliner were smudged in the corners of my eyes. I picked up a bottle of moisturising cleanser from the shelf under the sink and removed the last traces of ‘Michele’ from my body.

I winced as I pulled on my denim prison uniform fatigues and felt the scratch of stiff cotton on my body instead of the luxurious feel of satin, silk and nylon. ‘Stop it!’ I told myself as I found myself wishing I could exchange the scratchy denim and cotton work-wear for the soft feel of feminine garments; ‘this is how you are supposed to be dressed Mike; as a man!’

I made my way back to my accommodation cellblock without further incident. I was amazed to find my cell unlocked and unguarded. Fucking Eddie ran the whole prison I was sure if it! I let myself into the relative privacy of my own cell. With only a peephole in the door for the guard to look through instead of the open bars of the workroom cells in E Block it was as private as one could get in prison. As my head hit the pillow my mind was spinning with what had happened to me, how drastically my life had changed in one day. The last thing I noticed through teary eyes before I fell into a deep sleep was the clock on the wall ticking over to 2:30am.

I awoke the next morning and looked straight at the clock; it was 9:30am. Eddie must have arranged it with the guard on my wing to let me sleep in. I was tired and sore from the events of the previous evening and the early hours of this morning, I just couldn’t believe what had happened to me. I seemed normal enough (or as normal as one could be when you are a guest in Chelmsford prison); just Mike. Mike brushing his teeth, Mike combing his hair, Mike changing into clean fatigues. Mike drinking coffee alone in the deserted cafeteria. There was no sign of Michele or her feminine ways; Christ I wished it were all just a bad dream!

I looked down at my hands holding the coffee cup and noticed that there were little crescents of red nail polish under the cuticles of some of my fingernails. "Fuck!!!" I exclaimed. Then I heard the voice I feared most; Eddie had snuck up on me and whispered in my ear,

"Come on Secretary you’ve got a lot of work to do. Just because I’ve found you some after-hours employment, doesn’t mean you can neglect your day job," he snickered.

I followed him and took up my usual post working on Eddie’s books as I had done every day for the last few months. I couldn’t bear to bring up with him the events of last night or even look him in the eye. What I did do though was to pay particular attention to those parts of Eddie’s business that had now come to directly effect me. Because Mabel ran the books relating to the prostitution ring, I had never really paid them too much attention before, except to check the bottom line for profit against loss; today I paid them special attention.

how Eddie’s prison business works and how Mike/Michele ended up becoming Eddie’s accountant and ‘secretary’.

A note for those of you who haven’t read Part I of this story; you probably need to read it now to understand

It was all there, the amount each punter paid Mabel for a ‘session’ with each ‘girl’ (there were various codes that I didn’t really understand but as some sessions cost more than others, I could only deduce those punters wanted ‘special services’ and paid accordingly). Here was listed the earnings made by each of Eddie’s transvestite hookers against the costs involved in running his secret prison brothel. Payments were listed to Mabel, the guards (although a lot of the guards seemed to take their payment in ‘trade’), and the inmate ‘minders’ Eddie employed (I shuddered as I though about how ‘Iron-bar Steve’, his most vicious minder, had used me).

The costs of female attire, lingerie, cosmetics, perfumes, wigs, shoes and other accessories were carefully recorded against each girl’s name and deducted from her earnings. It appeared that despite these costs, and even after Eddie had taken the larger part of the profit for himself, the girls still made a substantial amount of money. By prison terms they were rich; in fact they probably made more money than your average streetwalker did on the outside.

Then I looked up the ledger entries Mabel had made against me, ‘Michele’; I was astounded at how much money Eddie had made from me last night, even though only a couple of my ‘tricks’ were paying customers. Then I looked in the debit column at how much money I owed Eddie; I was flabbergasted. I owed him thousands of dollars for the clothing and accessories he had purchased for me!

"What the fuck Eddie?" I turned around and shook the ledger book at him.

"This is bullshit! I’m a rich man outside but it will cost me double the money I owe you in bribes to have that much smuggled in!"

"I suppose I have no fucking choice, It would take me weeks to pay this off earning the money you expect me to make in your filthy whorehouse!"

I couldn’t believe that in my outrage I was shouting at Eddie like this.

"Oh no Secretary bird; months at least; probably a year to clear that debt!" he laughed.

"What the fuck?" I stammered.

Eddie reached out and grabbed my slender throat,

"You can only pay for the goods and services I provide for you with the services you provide to me!"

"What the fuck does that mean?" I asked. "Why can’t I just pay you out from money I have on the outside?"

"All of your clothes, makeup, wigs, nylons and those nice frilly things I have you wear, you have to pay for out of the money you make in the workroom. That’s the deal. How do you think I keep my little harem working for me?" he responded.

"And of course you will always need more of those lovely things, because, as you can imagine, they tend to get worn out quickly and suffer more than their fair share of wear and tear during the working day; or should I say working evening," he laughed.

"And I can’t have my punters complaining that my girls dress like shit now can I?" he mocked.

"Besides; look on the bright side, you get to keep everything you pay for and I’ll let you keep any tips; pardon the pun," he laughed.

"In a few weeks, once you get to like the work, you will be asking for more and more clothing, lingerie, and girly luxuries, all my girls do," he finished.

"Girls?" I stammered.

"Girls! Girls! Fucking GIRLS!!!!!"

"They’re crossdressers you dolt! They’re men! Men! MEN!!!"

"And so the fuck am I! I’m a fucking MAN not a GIRL!!!!!"

Whack! Everything went black.

I woke up on my bunk in my cell my head throbbing.

"Christ!" I groaned.

Eddie had obviously belted me during my outburst and knocked me out. I raised myself off my bunk and looked in the mirror. No visible damage done; just a bump on the back of my head. Eddie was too smart to mark his latest money-spinner.

I noticed my cell door was closed and on further inspection locked. Then I noticed a suit-bag hanging on the end of the double-bunk. On the disused top-bunk was a pair of black high-heeled open toe sandals, a makeup case, a pair of expensive Italian pantyhose still in their wrapping and some boxes that when opened contained white satin lingerie. A wig composed of a shiny black bob, with discrete cerise highlights was perched on a wig-stand. I recognised it as one of the wigs Carmel had had me wear last night. The wig had been cleaned, combed and styled; the harsh prison light bulb picked up the highlights in the hair.

I walked over to the suit-bag and noticed a note pinned to it. It read:

‘Get dressed. Be ready by 1pm and make sure you look good for a special friend of mine. Steve will pick you up.

Or don’t get dressed, your choice!

If you’re not dressed when Steve gets there you won’t need to get dressed in anything but hospital pyjamas for at least a month!

Love Eddie

XXX’

Resignation came crashing down on me yet again; I would not be able to get out of Eddie’s clutches until I was released from Chelmsford…or… a glimmer of hope formed in my mind…transferred!!! That was it! I would get a transfer! I had plenty of money outside; sure it cost me double every time I tried to get any of my money smuggled in, but if Eddie could bribe the guards, surely I could too! All I needed to do was to find out the right person to bribe. I made a resolution right there and then. I would withstand whatever depravity I had to until I could arrange a transfer to another prison. With this resolve firmly in my mind I started to get dressed into the clothing that had been bought into my cell whilst I was unconscious (probably delivered by Mabel in her male alter ego: the washed up trustee lifer).

I shucked out of my prison fatigues and stood naked in the centre of my cell. Short, slim and well proportioned with all of my body hair removed my body did not look especially feminine; but it was more womanly compared to most of the inmates in here who were either bodybuilders or had resigned themselves to lives of flabby inactivity. Maybe I could fatten myself up so that I wouldn’t be attractive to men? Then I remembered Charlotte, the chubby whore from last night, being fat had not worked for her, it had just made her more attractive to men who liked larger women (BBW’s as they were referred to in men’s magazines).

I opened the large makeup case and investigated the contents. It contained plenty of makeup, a small bottle of perfume and some jewellery in the upper compartment tray. I removed the upper tray to discover that in the bottom compartment was a pair of breastforms. The two silicone tits looked forlornly up at me from the bottom of the case. Breastforms! This time yesterday I wouldn’t have had a clue that the fucking things even existed. I selected the ruby red nail polish out of the makeup case and sat down on my bunk and painted my toe and fingernails contemplating the future. Eddie obviously had a special trick lined up for me this afternoon; what he didn’t know was the trick I was going to play on him; if I could just find out who I needed to bribe to get out of this nightmare.

I laid out the makeup on the shelf in front of the mirror over the sink and started the transformation from Mike to Michele.

I applied a layer of heavy foundation from my hairline all the way down to the bottom of my neck. Next I applied a second layer of Revlon foundation that matched my natural skin tone and then set the foundation with a lighter shade of face powder. I rouged my cheeks to highlight my sharp cheekbones, applied another light dusting of powder, and then went to work on my eyes.

My eyebrows were thin anyway and just required a light touch of pencil to form the arches. I applied a pinkish hued eye shadow to my eyelids and then blended a light aqua from there to just under my eyebrows. With a fine brush I applied black eyeliner in a thin line on my eyelids as close to my eyelashes as possible, top and bottom. I took the line right into the corners of my eyes as I had been taught. I applied lashings of black mascara to my eyelashes, only having to clean up a few little flecks that dropped onto my face. Next, three coats of the same plum coloured lipstick that I had worn last night, carefully applied inside the matching lip-liner. I pulled the black bob onto my head and adjusted the wig so that it sat correctly. I clipped a pair of silver and diamond encrusted sapphire drops to my ears and a matching pendant around my neck to finish the effect. I looked gorgeous; Carmel would have been proud of my efforts I thought to myself.

Now, to the foundation garments! I unwrapped the expensive looking Italian pantyhose. The diaphanous sheer black nylons were fully fashioned with dark reinforced cuban heels and toes; a neat black seam ran up the back of the legs to the top of the waistband. The gusset was as sheer as the rest of the hose with no joining seams or cotton insert that is usually found in the crotch area of most pantyhose. The nylons were decorated with tiny little rhinestones just above the heels.

I sat on the edge of the bottom bunk and slipped on the sensuous hose being careful not to snag them. My legs looked stunning, the little rhinestones made the pattern on the outside of each of my calves, the cuban heels tapered into the back-seam. I adjusted the seams to run perfectly centred up the backs of my legs. As I smoothed the hose little sparks of delight flew up my legs and I felt myself begin to stiffen. Before I could become further aroused I pushed my penis between my legs and held it there with the tight nylon gusset. These hose must be really expensive I mused.

Next I slid the white satin panties up my legs sending more little darts of pleasure into my body as they rubbed on the nylons. I stood and pulled the panties into place around my bottom and crotch. They were pure white, sleek and discretely laced around the waistband and leg openings. The full cut white panties stood out dramatically against the black nylon pantyhose; the seat of the full-cut panties encased the globes of my buttocks perfectly and the front panel was tight against my crotch with just my little package spoiling the effect.

I removed the breastforms from the makeup case and stood before the mirror and put them in place. I had applied a liberal amount of artist’s gum to my chest and the back of the breastforms as directed by the label on the tube I had found in the case. The directions on the gum promised to hold them in place ‘for hours on end’; they certainly felt secure. I just hoped the fucking things weren’t glued there permanently.

I put on the white satin bra next. Still a novice, this proved to be the hardest garment to get into. In the end I clipped the catches at the back of the bra together and pulled it on like you would a T-shirt, arms in first then pulled the back strap over my head. I wrestled the garment into position and smoothed out the sleek satin cups over my false breasts and untangled the straps over my shoulders and around my back. It was a lovely fit, perfectly matching the satin panties with a lace trim along the top of the breastcups with a single pale pink satin rose nestled between them.

The last item of lingerie in the packages was a full slip of the sheerest translucent white nylon. I slipped the item over my head and pulled it down so that the bodice fit snugly against my torso; the slip flared at the waist and finished mid thigh. The hem was trimmed with lace matching my bra and panties. The gossamer thin garment felt luxurious and when the material stroked against my nyloned thighs little explosions of pleasure ran up my legs.

I stepped into the patent leather black high-heeled sandals, my painted toenails visible through the reinforced toes of my stockings, the pretty cuban heels accented by the ankle straps of the shoes. I bent down and fastened a silver anklet around my left ankle; the chain sparkling as the light reflected off it accentuating the miniature rhinestones on my sleek hosed calves.

I stood up and unzipped the suit-bag. Inside was a navy blue suit and sheer white nylon blouse. I slipped into the blouse, the cool feel of the nylon sleeves sliding up my arms, the light material whispering against the full slip as I buttoned the garment. I stepped into the skirt; it was snug at the waist and tight around my hips and bottom, the hem coming to just above my knees. I pulled on the wide lapelled jacket and my transformation was complete.

I looked in the mirror stepping back so I could see as much of my reflection as possible. I was no longer Mike, the weak willed accountant; I was Michele, a power dressed executive; a ‘fem fatale’ in a business suit. I sprayed liberal amounts of perfume on my neck, behind my ears and then as Carmel had showed me, under my skirt.

I was about to sit down when my cell door slammed open. ‘Iron Bar’ Steve stood there in the company of one of the guards.

"Oh fuck me Steve she’s fucking gorgeous; I’d love to shag her bent over the bunk dressed just like that!" the dimwitted guard exclaimed.

"Fuck off stupid, you couldn’t afford a fucking hand job off her, she’s out of your league," Steve responded.

‘How chivalrous,’ I thought to myself, ‘A brain-dead thug defending the honour of a crossdressed inmate prostitute to a corrupt prison guard!’ I couldn’t help but smile at the irony of the situation.

"Oh you won’t be smiling for long honey," laughed Steve, "Eddie’s special friend doesn’t like jokes from fag inmates one little bit."

"Who are you calling a fag Stevie? You couldn’t get enough of me last night could you?" I clipped sarcastically.

Steve raised his hand but I stood defiantly in the doorway of the cell. I knew that Steve dare not touch me at the moment as I was all prettied up for some special punter. It was good to actually feel a slight empowerment for once. I sashayed though the cell door deliberately taunting Steve but I paid the price as I passed him; he reached out and squeezed my pantied buttocks through my skirt.

"Don’t touch the merchandise Steve," I taunted again, turning my pretty face to his and pouting at him.

"Oh don’t worry Michele, I’m just here to escort you to your special date, but you will be well used merchandise when you return," he laughed.

I looked around the cellblock and noticed it was empty. All of the prisoners were at work of course, but I couldn’t see any guards either, other than the dimwit who had unlocked my cell and was now making his way back to the guard’s office at the end of the block.

"Oh don’t worry honey, you’re getting the red carpet treatment, no one is going to see where your going except for a select few in the know," Steve said, tapping the side of nose..

Steve led me through a series of doors and deserted corridors. I never saw another soul; the doors opened electronically when Steve swiped a keycard though each of the card reading devices fitted next to the door-locks. ‘Who the fuck is Eddie’s special friend?’ I thought, ‘He must have some clout to be able have a crossdressed prisoner led halfway through the jail without anyone seeing it happening.’ ‘And who the fuck gives prisoners like this maniac escorting me the keys to the jail; this was just fucking insane!’

We finally arrived at a set of fire stairs, the door to which Steve opened with a swipe of his card. He led me up three flights of stairs, me tottering on the high-heels I was still unaccustomed to wearing. He opened the door at the top of the last flight and held me back as he scanned the corridor for a few seconds.

"Ok, quickly now," he said grabbing my wrist and pulling me into the corridor behind him.

"This is his private entrance; I’ll pick you up from here in hour. Behave ok!" Steve whispered in my ear, kissed me gently on the earlobe, and pushed me through an unlocked wood paneled door and slammed it shut behind me.

I half fell through the door and as I glanced up I could just make out the name embossed on the door; in faded gold leaf lettering it said WARDEN.

Warden Stone was a large man and as I fell though the door he caught me in his strong arms.

"You must be Michele," he smiled, gazing directly into my eyes.

"Here take a seat," he insisted leading me to a large leather divan set against one wall of the large office.

I was mesmerised; I knew that things were obviously way out of the ordinary in this fucked up jail. What with Eddie running every legal and illegal activity he could, including a lucrative brothel staffed by crossdressed feminised prisoners, corrupt guards and inmates running around with the keys to the doors; it was just farcical. The lunatics were literally running the asylum. But this! The Governor admitting a crossdressed prostitute, delivered by a messenger from the hardest criminal in the jail, into his private office; this was beyond comprehension!

But then again; in some fucked up way it made sense. How could Eddie possibly get away with what he did in here without the blessing of the Governor. In fact it made even more sense as I quickly caught on to the enormity of the situation; this was where Eddie’s largest payments went to; the Warden, they were obviously partners. The Warden ran the jail but Eddie ran everything inside the jail and the Governor got his cut; including the fringe benefit of access to Eddie’s working girls whenever he wanted. How else could all this be explained?

At the same instant another lightning bolt struck me; I was now with most powerful man in Chelmsford prison, if anyone could get me a transfer out of here it was him! I decided right then and there that I was going to be very nice to the Governor; no matter how disgusting his needs were, I was going to tend to every one of them willingly. After all, this could be my only shot at getting out of this nightmare. ‘So Mr Stone,’ I thought to myself ‘You’re about to have the wickedest hour you ever spent with one of Eddie’s whores!’ I mustered my resolve and made my move.

"Why thank you Warden Stone," I offered him by biggest smile and sat down, crossing my legs in a ladylike fashion so that the hem of my skirt rode up to mid thigh.

I noticed his eyes open wide and heard a sharp intake of breath as he heard the soft rasp of my nylons rubbing together and stared at my thighs encased in their gauzy nylon sheaths.

"Stanley please," he smiled back.

"And you are Michele I’m told," he went on.

"Well Michele let me paint a picture for you; I’m sure you are not naïve and understand why you are here. But there is no need for this to be unpleasant for you; I assure you that I can behave like a gentleman, and this scant hour we have together can be a welcome break for you from the filth and depravity you experience very day in my prison."

"So Michele, shall we spend a nice relaxing hour together?" he asked expectantly.

"Why Warden, I mean Stanley; if you are the gentlemen you already appear to be I’m sure I can behave like the lady you want me to be. Perhaps we can even accommodate each other in other ways if you would like to discuss a proposal I have for you?" I responded maintaining my painted smile.

Warden Stone’s face clouded over at my proposal; I had gone too far too early; I went into damage control.

"But of course that’s for later, please sit with me," I patted the leather couch next to me and batted my lashes like a good little coquette.

Stanley smiled again and managed to drag his gaze away from my legs to my eyes.

"Lovely, but please, allow me to get you a drink; scotch?"

"Please," I smiled back and he turned to an expensive looking oak cabinet to pour the drinks.

‘I might as well make the most of this,’ I though to myself as I glanced around the Warden’s impressive office. As one would expect it held all the trappings of power; a large desk, chunky furniture, the wall adorned with certificates, trophies and pictures of the Warden with other powerful men. On his desk I noticed a picture of the Warden and his family. His wife appeared mousy and his daughter was a skinny teenager with dank hair; they were smiling painfully for a picture obviously posed to project family harmony. I wondered what his mousy wife would think if she knew that Stanley’s peccadilloes ran to intimate encounters with crossdressed prison inmates?

Stanley returned to the large sofa, stopping off to turn out the overhead lights and check that the door to his outer office was locked and the shades lowered. He set the drinks down on side table and adjusted the one remaining lamp to a diffused glow. ‘Very cosy,’ I thought to myself; ‘I bet his receptionist is on an errand for an hour or so.’ I wondered how often he did this?

The Warden handed me my drink and indicated the vacant place beside me on the sofa,

"May I Michele?" he asked smiling.

"Of course Stanley," I smiled, again patting the seat beside me.

Stanley sat down heavily beside me and the cushion gave way under his weight so that I leant in towards him slightly, the golden liquid and my red fingernails glimmered in the diffused lamplight as I raised my glass to him.

"Cheers," I whispered and drank heavily from my glass.

"Cheers," he responded, downing the spirit in one huge gulp.

Stanley had to be over a hundred and thirty kilos and close to two meters tall; well proportioned but large; I noticed the beginnings of a paunch hanging over his belt as his suit jacket opened. ‘Ok this is it,’ I decided; ‘lets get this façade over with!’

I reached out and took his empty glass from him and placed it on the side table beside mine, a crescent of lipstick decorated the rim of my glass.

I turned to face the Warden and reached out to him, gently taking his head in my hands, I pulled his face towards mine seductively opening my lips slightly. Stanley groaned and pressed his lips lightly against mine. He kissed me softly, with his mouth closed; then he reached out and put his strong arms around me and eased me against him as he smothered my face with feather soft kisses. He kissed me all over my face; my lips, my cheeks, my forehead, and placed little butterfly kisses on my lightly closed eyelids.

"You are so beautiful," he whispered in my ear, gently nuzzling my earlobe.

My hands were now on his powerful shoulders and we embraced each other for a few minutes; softly kissing each other, I felt the heat slowly growing in him as he became aroused.

I felt his hand slide down my body and come to rest on my knee; he softly massaged my leg, slowly working his hand higher, lightly stroking the inside of my stockinged thigh. His breath was becoming heavy now but he made no attempt to force himself on me; his mouth remained closed as he tenderly rained down soft kisses on my mouth and face.

I reached out with one hand and placed it on his thigh feeling the hard muscle through the material of his trousers; the back of my hand brushed briefly against his tumescent member; he gasped.

"Oh Michele; you naughty girl!" he whispered, his hand sliding under my skirt came into contact with my slip.

The Warden wrapped his hand in the silken material and began to slowly glide the slip up and down my thigh. The feeling of the delicate fabric rubbing on my pantyhose was exquisite; my member began to awaken in the silken gusset of my hose; my tight white panties holding it in place as it slowly thickened and elongated.

I moved my hand across the bulge growing in the Warden’s trousers and found the zipper on his fly. He removed his hand from under my skirt and gently moved my hand away.

"No Michele, I want to taste all of your sweet treasures before we consummate our little interlude," he said and took hold of my upper arms in a tight grip.

‘Quite the wordsmith,’ I though to myself; ‘I wonder what sweet treasures he intends to enjoy?’

Stanley kissed me fully on the lips, pressing his torso hard against me, slowly sliding his tongue into my mouth; I tasted my own lipstick on his tongue as he gently explored my mouth. Then he pulled his face away from mine and eased me back against the padded armrest of the divan. I guessed that now he would want more than just kisses and caresses and as he adjusted his position on the sofa I made to remove my suit jacket.

"Oh please no Michele; I want you dressed just as you are. I love a woman who can pull off the whole power-dress performance thing and still look feminine and sexy."

"Do you like the lingerie? I had Eddie acquire it for you just for this occasion; and those nylons, God, I could eat you up in those. In fact I think I just might," he chuckled.

I relaxed back against the padded armrest and Stanley bent down and lifted my legs so that I was lying lengthways on the divan. I was lying with my back supported by the padded armrest and my legs across Stanley’s lap.

"That’s better," he smiled and began to stroke my legs with his hands.

"Oh that feels so sensuous, and I just love those little rhinestones sprinkled on your stockings," he said.

He bent his head and raised one of my legs to his mouth and commenced planting sweet little kisses all up and down my calf. He moved his lips slowly up and down my lower limb and then licked the back seam of my stocking all the way down to my high-heeled sandal. He kissed my feet, and pushed his tongue into the darker reinforced extremity of my hose and sucked on my painted toes through my open toe sandals. I must say it felt quite erotic.

Stanley used his free hand to stroke my other leg sliding his fingers far up under my skirt, stroking up and down my leg slowly and sensuously.

"Mmmmm let me see," he groaned and lifted his face from my feet.

He opened my legs slightly and raised my skirt up around my waist. He gazed upon me lying there with my stockinged legs in his lap with the hem of my slip coming halfway down my thighs, the pure white nylon slip in contrast with the dark hosiery.

"Lovely," he said, and began to kiss me up and down my legs again.

This time he buried his head under my slip and continued up my legs right to the top of my thighs. He kissed the front panel of my satin panties whilst stroking my legs. After a minute or so of placing soft kisses on my panties and thighs he made his way back down my legs and began to suck on my nylon sheathed toes again. His hands were now sliding the soft material of my slip up and down my thighs creating wonderful sensations through my body. My member was stiffening further and was becoming uncomfortable being held in place under my crotch by my pantyhose and tight panties.

Stanley was now licking my shiny black patent leather sandals, holding both my feet in place by the spikes of my heels. As he worshipped my feet and gazed up my legs, his eyes glazed over with lust; then he started sucking on the spiky high-heels, taking them into his mouth and lovingly caressing them with his tongue; first one then the other; as if fellating my heels.

He was panting and groaning as he worshipped my legs and feet. Then he moved one hand down to his fly and pulled on the zipper. His hand disappeared inside and rummaged around eventually freeing his erection; it protruded stiffly from his trousers, red, angry and engorged.

Stanley lifted my feet and re-positioned them one on either side of his hard cock and slowly started to fuck my feet. I realised what he was doing and assisted him. I slowly started to masturbate him with my feet, slowly lifting them up and down, letting my soft stocking foot caress the head of his penis and then the patent leather of my shoes.

Stanley threw his head back against the cushioned divan and let me foot fuck him. He renewed his carnal attack on my legs as I wanked him with my feet. I trapped his member my feet and stroked hard. He moaned and writhed in ecstasy.

Then he looked at me again and gently moved my feet out of his crotch. He stood up and re-positioned himself on the divan so that he was kneeling between my spread legs. With trepidation I thought, ‘Here he goes; he’s going to fuck me.’ But he didn’t. Stanley closed my legs and lifted my feet up to his mouth and began to worship them with his lips and tongue again. I was lying down full length on the divan now with just my head pillowed on the armrest, my skirt and slip rucked up around my waist with my legs lifted up whilst Stanley took oral pleasure on my feet and calves. Now I knew what ‘sweet treasures’ the Warden wanted to taste; he was a foot fetish. ‘Well at least I might leave here without having to gratify him in some other disgusting way,’ I thought to myself.

Stanley was now in a frenzy, lapping and sucking at my shoes, toes, and feet; he was panting, his face red and sweating. Stanley actually looked quite pathetic dressed in his full suit with just his stiff penis poking out his trousers as he paid homage to my peds. He stopped briefly and quickly fumbled at his waist, undoing his belt and pushing his pants down around his thighs. Then he gripped my ankles, lowered my legs and pushed my feet together. He pulled my feet between his legs so that his cock lay in the silken valley created by my calves. Then he started to fuck my legs.

He rubbed against me faster and faster and I could feel the friction of his hard cock against my nylons. Stanley groaned and whimpered. His gaze alternated between my face and my pantied crotch as he pushed his cock against me harder and faster.

I decided that I would assist him with his fantasy and placed two slender, red-nailed fingers on the gusset of my pure white satin panties and began to stroke. Stanley reacted immediately.

"Oh yes Michele! You naughty, naughty girl!"

"You are such a pretty girl, but such a naughty girl," he chanted.

"Oh Michele, you naughty nyloned princess I’m going to come; I’m going to come all over your pretty toes and feet; would you like that?" he begged.

"Yes Stanley please; please come all over me!" I role-played for him as he approached his climax.

He shifted his grip to my ankles again and pulled my feet up to his quivering member. I knew exactly what he wanted and began to masturbate him hard and fast between my feet; pushing back and forth with my legs so that my high-heels and stockinged feet ran up and down the length of his shaft. At the same time I furiously rubbed the front of my panties; a parody of a woman pleasuring herself.

"Come for me Stanley; come on honey, come for Michele baby," I cooed.

Stanley’s face screwed up and went bright red as a shattering orgasm washed over him. Ropes of creamy semen jetted from his penis splashing up my legs. Spatters of his spend formed sticky white pools on my calves and feet; they glistened in stark contrast on my black stockings. My diaphanous black hose became darker still in the places where Stanley’s semen soaked into the nylon.

A silvery thread of Stanley’s ejaculate hung down from the heel of one my shoes forming a sticky necklace between my foot and his deflating penis.

"Oh Michele, that was wonderful," Stanley gasped and collapsed on top of me.

His weight nearly knocked the breath out of me as he started to cover me my face with soft kisses again. I pushed lightly against him until he took the hint and rolled off me so we were lying side by side. Stanley pulled me close against him, one arm over my body caressing my buttocks, slowly stroking the sheer nylon slip against my panties. His kisses grew harder and his tongue now invaded my mouth; I could hardly breath. I managed to pull my face away from his.

"I’m glad you liked that Stanley; was that how you wanted to take me?" I whispered in his ear.

"Oh yes Michele, but that was just an entrée sweetheart; I recover very quickly," he whispered back.

"Perhaps a drink Stanley, before we play some more?" I asked.

I was getting confident now; the Warden was obviously a submissive, I had read that powerful men often liked to take on a submissive role during sex play. I decided to test my theory.

"Come on Stanley, pour me another scotch and we can discuss a proposal I have for you. If you are a good boy and treat me nice I might let you have some more," I teased.

I was not prepared for what happened next; I had hopelessly misjudged the situation.

The Warden used his powerful build to roll me onto my back and pull himself up so he straddled my waist. One huge hand came across and swiped me on the side of my face, stinging and numbing me.

"Oh I don’t think you realise the situation here bitch! I’m the fucking Warden of this jail and you’re just another slag who Eddie provided for me to use as I see fit."

"Don’t try and offer me proposals! I make the fucking proposals here!" he screamed at me.

"Now here’s a fucking proposal; lift your fucking trollop arse up off my lounge," he yelled.

Warden Stone stood up and dragged me off the divan and shook me like a rag doll. I was terrified; the man had turned from being a gentleman to a demon in the space of seconds.

"Here’s another fucking proposal," he barked and shoved me hard towards his desk.

I tottered on my heels and reeled over towards the desk; one of my shoes flew off and my stockinged foot slid on the polished floor. I reached out trying to grab the desk for support but I collapsed on the floor beside the desk, legs akimbo.

"And here’s my final proposal," the Warden bellowed and moved in, pulling me up off the floor and bending me over the huge oak desk.

One bear-like hand grabbed my skirt and tore it from my body; the side seam splitting with a loud rip. The Warden pushed me down harder on the desk, he put one hand on the back of my neck and mashed my painted face onto the hard surface of the desk. With his free hand he pulled my slip up and over my back and I realised how exposed I was in this position. I was bent over the desk with my skirt ripped off, my slip hiked up, tottering on one heel, my satin pantied buttocks raised and exposed.

Warden Stone let go of my neck briefly but it was no relief; I was horrified by what he did next. He put both hands on my hips and yanked my panties and pantyhose down in one swift movement. They tangled in a bunch at the top of my thighs.

"No! Please, Stanley don’t do this," I whimpered.

"What you mean this, you cocksucking whore," he taunted and I felt him position himself behind me, his swollen penis probing at my buttocks.

"No! No! Please!" I begged.

"Well what do you think of my proposal Michele?" he grunted and pushed forward with all his weight.

"Ohhhhhhh god no!" I moaned as his member slid all the way up inside me.

I felt as though I had been split open. It was so tight and he was in me so deep that I could feel his groin hard against my bottom. Then he raped me. He just fucked me like a whore. Bent over the desk I could offer no resistance as Warden Stone commenced thrusting in and out of me. I don’t know how long he ploughed himself into me; at least ten minutes; he obviously had plenty of staying power having just recovered from an orgasm only minutes ago.

He grunted and groaned, calling me filthy names and slapping my buttocks as he fucked me hard and fast. His cock pistoned in and out of me and his groin slammed against my buttocks. I forced myself to relax my sphincter but the pain was still excruciating. Eventually the lubrication from his pre-seminal fluid eased some of the pain as his invading member continued to rape me.

Eventually he bellowed, grunted and puffed and suddenly I felt the hot ooze of semen inside me. The Warden wasted no time and pulled himself out of me immediately. He yanked my panties and pantyhose up over my buttocks and I felt him wipe his penis clean on my buttock; his warm spend left a wet patch on the cheek of my bottom. I remained bent over the desk, silent and humiliated, feeling vile and debased as the Warden pulled up his pants and shoved the tails of his shirt into the waistband of his trousers.

There was a gentle rapping at the wood paneled door through which I had entered the office only an hour ago. The Warden grabbed my arm in a vice-like grip and dragged me across the office. He opened the door and threw me outside like a piece of garbage; I tripped and fell to my knees on the hard polished floor tearing my beautiful pantyhose. I looked up to see ‘Iron-bar’ Steve smirking down at me. The Warden briefly disappeared back inside his office, then returned to the doorway and threw my shoe and my ripped skirt at me.

"Tell Eddie I’ve finished with this for now. She’s one of his better whores, but she has too much of a mouth on her," Warden Stone barked at Steve and slammed the door shut.

 

 

 

 

 

Malcolm was a middle manager in a small business in a large city.  Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life.  Malcolm had a few girlfriends over the years but never anything serious; he kept himself to himself and rarely socialised outside of a small circle of colleagues and close friends he had cultivated over the years.  Malcolm was boring really; but he one closely guarded secret.  Malcolm was a crossdresser.

 

Once or twice a week Malcolm liked to lock all the doors of his modest two-bedroom suburban home, close all of the blinds, take the phone off the hook, and dress like a woman.  It had started as nothing really serious; as a child he had liked to play with his older sister’s panties and nylons; he loved the feel of the garments against his skin and occasionally he would wear his sister’s underwear for an hour or two and then carefully place it back in the laundry basket.  His fetish continued into his teens and when he finally left home and got a place of his own be bought his own panties, stockings and pantyhose and would spend the odd evening dressed in the silky articles.

 

Malcolm enjoyed his fetish alone and never talked about it to anyone, not even to whoever his current girlfriend might be at the time.  Every now and again he was successful in talking a girlfriend into wearing stockings or pantyhose during sex and he loved the sensation of fucking her as she wrapped her nylon encased legs around his body; but it was not the same as wearing them himself.  After a few years he also added petticoats, slips, suspender belts and other lingerie to his collection.  Then the internet explosion happened.

 

Like most men Malcolm went searching for pornography on the net and concentrated on searching for sites which contained lingerie and hosiery fetish.  Then one day he typed “men in pantyhose” into his web-browser and as he explored the matches to his search he came across a few sites dedicated to crossdressing.  He followed the links further and further into the cyber-world of crossdressing and he was fascinated by it.  He saw so many pictures of guys dressed not only in lingerie but fully dressed as women; wearing women’s clothes, shoes, wigs and makeup.  He became hooked.

 

Eventually he summoned up enough courage to acquire some clothes, makeup, shoes and a couple of wigs.  He would buy the items whilst he was away on business; never in his home town; he was terrified of being caught.  And so Malcolm went on year after year, dressing up once or twice a week, home alone and surfing the net where he entered chatrooms to chat on line with other closet crossdressers about all sorts of TG issues.  He soon discovered that the world of the Transgendered was often confusing and mostly secretive.  A few of the girls he chatted with on line were Transsexuals and wanted to live their lives as women.  Some Crossdressers dressed so well that they could pass as women but were not at all interested in becoming women; they just loved to dress as women and sometimes they got together.  They called themselves Transvestites and some of them met up to share their experiences or just to be in each other’s company; some of them belonged to an organisation called the Seahorse Club.  Other Transvestites met up to have sex with each other or with men. He discovered that the men who liked to have sex with Transvestites were called Admirers and they trolled the chatrooms and websites looking to arrange meetings.  But most of his online friends were like him; for reasons many and varied, all they wanted to do, or most often all they could do, was to dress up at home and enjoy what they could of their fetish, alone or in the cold world of cyberspace.  A lot of them were married men who kept their crossdressing activities secret or ‘in the closet’ as the colloquial term was known. 

 

Yes it was a very exciting but confusing world out there in TG land and up until now Malcolm was content with his lot; he never dreamed of going out dressed as a woman and even though he sometimes fantasised about meeting other Crossdressers or Admirers he was too scared to do so.  Malcolm was just too terrified of being caught; he was horrified of what the consequences might be if his colleagues and friends; or even worse his if his family found out about his secret.  A couple of times he had summoned up the courage to wear pantyhose and panties to work under his male attire and even though it had thrilled him he had one bad incident which had scared him from ever doing that ever again.

 

Malcolm got on with everybody, especially everyone at work; he was friendly, cheerful, a good listener and worked hard.  But there was one person there who just didn’t like him.  The guy’s name was Eddie and he was the office jerk.  If there was an office prank or someone was the butt of a practical joke, then you could pretty much guarantee that Eddie was behind it.  He was annoying, but harmless enough and very productive; the bosses liked Eddie and turned a blind eye to his misgivings because he earned well for the company.  In fact the only other manager whose department earned more than Eddie’s was Malcolm’s; maybe that’s why Eddie was particularly vindictive to Malcolm with his petty practical jokes.  Malcolm mostly ignored Eddie’s jokes and snide comments but one day he let his guard down and paid a hefty price.

One day Malcolm had gone to work one day wearing black sheer to the waist pantyhose and pink nylon panties under his business suit and was enjoying the thrill of being dressed that way secretly in public.  On the rare occasions he went to work wearing pantyhose and panties he was very careful to make sure that his secret was safe; if he had to go to the toilet he would use the cubicles that had full length doors and when seated at his desk he checked every few minutes to ensure that his shirt remained tucked in, in the unlikely event that the waistband of his pantyhose or panties might show.  This day he had to go pee and went to the men’s room and locked himself in the end stall, contented that he could lower his trousers and do his business without being caught dressed in panties and hose.  He hung his suit coat on the hook on the back of the cubicle door, lowered his pants and sat on the toilet seat with his panties and pantyhose bunched around his ankles.  What he didn’t know was that Eddie had followed Malcolm into the toilet to play a prank on him.  Malcolm never found out what the prank was; all he ever knew was that it somehow involved Eddie standing on the toilet in the stall next to his and looking over into Malcolm’s stall; maybe Eddie was going to throw a glass of water over  him or something equally inane. 

 

What did happen was that Malcolm heard snickering and looked up to see Eddies grinning face peering over the adjacent stall. Malcolm was horrified and just looked up slack jawed. Eddie just said,

 

 “Nice underwear sweet-cheeks,” and his face disappeared from view.

 

Malcolm spent the rest of the day, then the week, and then month in agony waiting for Eddie to torment him and ridicule him in front of his colleagues; he thought up ridiculous excuses as to why he might be dressed that way but the best he could come up with was that it was a bet; but with who?  As it turned out Eddie never said anything to anyone else; he just occasionally sidled up to Malcolm and whispered,

 

“Are you wearing them today?” winked and walked away.

 

Eventually Malcolm decided that Eddie was too scared to bring up what had happened because he would have to explain his own actions; spying on a man doing his business in a toilet stall.  Malcolm figured Eddie was content to just torment him occasionally with the question as to wether he was wearing female underwear to work.  Malcolm never wore female underwear to work after that; he remained content to just play dress-up at home.  Until one day………………

 

Every year on the anniversary of firm’s founding, the bosses paid out for a big party; it had become a tradition.  The party was fancy dress and it was held on the evening of the last working day before the Christmas break.  Over the years it had become customary for the party to have a theme; and the theme had a twist. The twist was that whatever the theme was, the women dressed in the male or dominant role and the men dressed in the feminine or submissive role.  One year it was ‘cops and robbers’; where the women came along dressed as policemen or prison warders and the men arrived dressed as criminals or prisoners (lots of horizontal striped shirts and black masks that year; like the Beagle Boys in the Scrooge McDuck comics).

 

One year had been ‘toffs and paupers’; lots of the women dressed in top hats and tails and the men dressed in the rags similar to the scallywags in Oliver Twist.  There had been ‘cowboys and Indians’ (girl cowboys, boy Indians); ‘heroes and villains’ (girl heroes, boy villains); and last year, the best yet, had been ‘knights and damsels’ with the girls dressed as knights, valets and lords of the realm, and the men dressed as medieval princesses and ladies of the court.  Everyone had a big laugh at that one, especially the men who had really got into the spirit of the thing with lots of them dressed up in drag in crinolines and ball gowns.  It was a big laugh for everyone.  Malcolm was tempted to dress up in his favourite lingerie, a ball gown, wig and makeup; but in the end had chickened out and came dressed as a court jester.

 

This year it was Malcolm’s turn to choose the theme because he had been voted the worst dressed at last year’s party.  The judging panel had decided that his court jester’s outfit was a copout on the theme and, as per tradition, the person voted worst dressed had to choose the theme for the following year.  It was considered a task not to be taken lightly; the more outrageous the theme the more acclaim it received; and the person who chose an interesting and outrageous theme became the most popular man in the company; for at least a few months anyway.  Malcolm had wrestled with the decision as to what the theme for this year’s party should be.  Malcolm being Malcolm, everyone expected something boring like ‘spacemen and aliens’ or some other safe subject matter, but they were all surprised and delighted when in late November Malcolm posted the theme for this year’s party on noticeboard. It was ‘Whores and Pimps’.

 

Of course Malcolm had his own secret agenda; for years now he had wanted to go out in public dressed as a woman.  Not like last year, dressed in a costume, but dressed in real women’s clothing, fully made up and feminised.  This was his big chance, and of course the more effort he made to be feminine the more he could justify it; after all, as the party’s organiser it was expected that he would endeavour to dress up as realistic as possible in keeping with the spirit of the theme.  The only concern he had was when he received an email from an anonymous address that simply said; ‘I might have guessed’, Malcolm was sure that Eddie had sent him the email but after a few days he pretty much forgotten about it.

 

Malcolm agonised for weeks as to how he could get away with dressing up as realistically as possible and to have a valid excuse as to why he looked so good dressed as a woman.  Last year the men who had dressed as ‘damsels’ had looked pretty ordinary; sure they had hired great costumes, crinoline ball gowns, tiaras, ladies slippers and so forth; but most of them had five o’clock shadow and their makeup was garish and clown-like, their wigs cheap and knotted poor facsimiles.   Then he had a brainwave; he would get his sister to dress him and make him up!  He could answer any questions as to why he looked so good dressed as a woman truthfully; “My sister dressed me and made me up,” and if anyone asked her, she would verify his claim.  She would be his unwilling alibi.

 

Malcolm hit the chat rooms in the days leading up to the big party and all his online friends encouraged him and offered advice; everything from “Don’t do it!” to “Go for it honey; stay out all night and pick up a nice man!”  Malcolm was a little perturbed about that last remark because sometimes, when he home alone dressed as a woman, he fantasised about what it would be like to be with a man whilst he was feminised.  He also hit lots of Transvestite web sites like TVChix, KTM, Crossdress World and so forth looking at pictures of Transvestites he admired to find the right ‘look’ for the party.  He wanted to look slutty but not trashy; sort of up market streetwalker.  He found a lot of girls in the UK and Europe had mastered the look he wanted capture; that dark haired beauty Lyn in the UK had the look; so did Janet Petteflet in Holland, Wendy Stockings in Scotland, and Cherry in Melbourne Australia.

 

Malcolm finally made up his mind as to how he wanted to look for the party; and then he had a dilemma that he hadn’t thought of before; one of his online girlfriends had asked him what fem name he was going to use.  When he was online he just used the handle ‘loves-to-dress’ and because he had only ever dressed alone he and had never talked to anyone in the real world about his transvestism, there had  never been a reason to have a fem name.  It would be easy to think up some trashy name to use at the party; everyone wore nametags at the party and they were usually the same absurd double entendres you heard on bad British comedies.  Names such as: ‘Sir Shagsalot,’ ‘Baron Ivor Bigun’ and ‘Princess Swallows’ had been some of the more ridiculous names used by partygoers last year.  He wanted a name that he could use at the party and that he could keep forever as his own secret name for when he crossdressed.  He thought about it for a few days and finally decided on a name.

 

He wanted a first name close to his male first name, but not so close that it was obvious; and his crossdressing had originally started out as a fetish for panties and hosiery; so the name came to him in an inspiration.  He played with the name Melanie for a while but decided that it was too close to his real male name.  He settled on Michele; Michele with one L, because it was a little bit different.  Malcolm decided his fem name would be Michele Nylons.

 

By the time the day of the party arrived Malcolm had made all of the many arrangements required of him as the organiser. The venue was the small function room of one of the cheaper city hotels, the catering, drinks and entertainment were part of the venue’s package; the firm paid for the party but they didn’t lend themselves to extravagance; after all the party was just really an excuse to dress up stupidly, get drunk and let off steam.  Also the firm’s thirty or so employees preferred the venue to be at one of the cheaper hotels because, as most of them and their partners got drunk at the party, they usually rented hotel rooms at the venue.

 

The previous weekend Malcolm had called his sister on Friday evening and explained to her about the party and his need to dress up as a whore for the theme; he then went on to clarify why he needed to look as realistic as possible because he was the host and organiser it was expected oh him, and begged her for her help.  He went on to say that he had some ideas as to how he wanted to look and that he had even got hold of some pictures off the internet to help him decide how he should look.  As he had no idea how to dress like a woman she would have to help him.  She eagerly agreed and was pleased that the normally quiet, reserved Malcolm was coming out of his shell for this event.  She told him to bring along the pictures on Saturday morning and they would go shopping for everything they needed so that Malcolm would look as whore-like as possible; it would be fun!

 

When Saturday arrived Malcolm met his sister Angie in the city outside of a large department store.  He had already figured out that he needed to behave naive when it came to world of women’s clothing and makeup; but he was determined to ensure he got exactly the look he wanted; he would have to be cunning that’s all.

 

“Hi Angie,” he said, and kissed her cheek when she arrived outside of Myer; one of the better stores in town.

“Hi Malcolm,” she responded.

“Let’s get you feminised then, you hussy,” she laughed, and Malcolm blushed; ‘If only she knew the truth,’ he thought.

“Come on; lingerie first,” she said enthusiastically and took his hand and led him into the store.

They made their way to the lingerie section of the store and started looking around.

“When you say you have to look as realistic as possible does that mean underwear too?” she asked.

“We can get away with some cheap foundation garments if you like; we can squeeze you into a cheap bra and you can just wear your own underwear under women’s clothing if you like?” she added.

Malcolm was horrified at the prospect.

“No; definitely not!” he enthused, “If we are going to make me look like a hooker, then lets go all the way; I want to win best dressed and who knows how good some of the other guys will look; it can be quite competitive you know and it might come down to who is wearing the best knickers!” he laughed, hoping he hadn’t gone to far and given his real motive away.

“Alright then; lets turn you into a complete slut,” Angie giggled, “This is going to be fun!”

“My boring, unadventurous, brother is really getting into the swing of things.  It’s about time!” she added.

Angie led Malcolm to the brassiere section of the lingerie department and he pleaded ignorance as she expounded the various virtues of the different types of brassieres.  They eventually settled on red satin full cup, size 14C.

“Red is definitely a whore’s colour,” she chuckled “and your panties should match; they usually have a matching panty for the better quality brassiere you know?”

“Do they really?” Malcolm responded feigning ignorance of such things.

“Here they are!” she quipped, delighted at having found the matching item on the rack of panties below the bras.

“Now I reckon any whore would love these,” she laughed, “here; what do you think?” she asked holding a pair of red satin bikini panties up for him to see.

“How the fuck would I know Angie? And do you have to hold the fucking things up for everyone to see they’re for me?” he pretended to be angry.

“Oh don’t be silly Malcolm; if anyone asks we just tell them the truth.  Besides you will have to try on some of the clothes anyway, at the moment I’m just guessing your sizes,” she responded.

“You mean women have different sizes to men?” he quizzed.  Malcolm knew exactly what size he was in women’s clothes and shoes but he couldn’t let on.

“Of course; at the moment I’m guessing your about a 14; a larger size for a woman even though you take a medium size in men’s clothing.”

“Ok,” Malcolm tried to sound befuddled but she had nailed his size in one guess.

“Now if you want to look like a real whore then we had better get you some stockings; we can get stay-ups or we can get the type that require garters or a suspender belt; what do you think?”

“Definitely suspender belt!”  Malcolm responded a little to eagerly.

Angie looked quizzically at her brother and he reddened.

“Angie; I’m a man so I have seen plenty of pictures of scantily clad women in my time and the sexy ones always wear suspenders and stockings,” he responded.

“Suspenders and stockings it is then,” she laughed.

“Oh I just love this one; and it matches the panties and bra,” she said, reaching for, and then holding up a red lace garter belt with six long red suspender straps hanging from it.

They wondered over to the hosiery section and began to browse.  Angie rummaged around and eventually held out a package to Malcolm.  ‘Sheer Fully-Fashioned Seamed Stockings by Kaiser” the label said.  A little clear window in the package displayed that the stocking were black.

“Perfect,” Angie said. “Whores always wear black stockings.”

“Mmmm,” she mused, “Show me your legs.”

“What?” Malcolm responded caught unaware by the request.

“Show me your legs stupid,” she repeated and reached down and pulled up one leg of Malcolm’s pants up to his knee.

“Just as I thought; hairy! That will never do!  Even though these stockings are black your hairy legs will show through; we’ll have to get you some pantyhose to wear under them,” she went on; dismissing Malcolm and rummaging again amongst the many packages of hosiery on the shelves.

“Just the thing!” She sounded delighted and flung another package at Malcolm.

This time the label said ‘Kolotex Sheer To The Waist High Sheen Pantyhose.’ ‘Colour – Taupe’.

“Jeeze, I didn’t realise it was so hard being a woman?” Malcolm laughed; again pretending ignorance but secretly pleased at all of the selections Angie had made so far.

“Ok buster; now comes the hard part; skirt and blouse.” Angie went on and led Malcolm further into the store.

“Didn’t you say you had some pictures?” Angie asked.

“Well I got these off the net,” Malcolm said. “Apparently the women in the photos are really men; Transvestites I think they are called.  They look realistic to me though.”

“Malcolm; you are the dark horse; I never dreamed you would know about such things!” Angie looked shocked as Malcolm handed her the pictures.

“Well I never did know anything about this until I had to organise this fucking theme party!” Malcolm pretended to be angry again.

“I just entered a few keywords into my browser and these are some of the pictures that it came up with.  And I’ll tell you what; some of the other pictures were actually pornographic.  Do you know there are some sickos out there that actually LIKE dressing as women?” he went on.

“Malcolm you have led a sheltered life haven’t you,” Angie answered but she was now too busy looking at skirts to carry the conversation on any further.

Angie looked at the pictures and looked at some skirts on a rack.  She poked around for a while selecting items and then putting them back. Finally,

“Yes; this is it!” she squealed.

Angie held out a black leather miniskirt looking extremely pleased with herself.

“It’s just like this one the girl; well man; well whatever; is wearing in this picture,” she said; pointing to a picture of Janet Petteflet which Malcolm had downloaded from KTMGirls. 

“Now for the awkward bit; you will have to try it on.”

Malcolm paled; he hadn’t though of that.  He knew that he was usually a size 14 in a skirt but also knew that sizes varied; he had a couple of 12s and even a 16 at home.

“It’s no good frowning and looking sorry for yourself.  If you are going to spend all this money to dress up for one stupid party we at least better make sure the clothes are going to fit you.” Angie scolded.

As it turned out it wasn’t that difficult.  Angie being Angie just went up to the floor supervisor and told her the truth; that Malcolm had to dress up in drag for a party.  The supervisor, an attractive woman in her fifties, was only too delighted to help.  She led them to a single fitting room that had a full length door that was separate to the rest of the female fitting rooms.

“We keep this room for special clients and the handicapped; It’s separate to the rest of the fitting rooms and very discreet.  Just find me when you have made your selections and I’ll see to you personally,” the floor supervisor smiled.

“Right; now a blouse!” Angie went on and charged on through the women’s clothing department to where there were what looked like thousands of blouses.

Malcolm was so glad that he had though of using his sister as a ruse; she seemed so enthusiastic and was actually having fun selecting clothes for him.  This was going a lot easier than he thought it would; he didn’t have to explain what he wanted at all; Angie was taking the lead and selecting just what he would have chosen to wear himself.

“Finally!” Angie exclaimed holding up her prize after what seemed like eternity as she waded through a sea of blouses and tops.

It was a sheer nylon leopard-skin patterned, longsleeved blouse and it was perfect to go with the black leather miniskirt.

“Right lets get you sorted brother of mine; go and wait by the fitting room.” Angie dictated and stormed off back towards the skirts.

A few minutes later Angie returned with the floor supervisor; her arms loaded with clothing.

“I’ve got the skirt and blouse in size fourteen and sixteen,” she said “Try them on in there and make sure they fit properly; can you do that?”

“I know,” she went on, “take this in with you and try to make sure you look as good as the girl in the photo,” she said, handing him the picture of Janet Petteflet.

Malcolm went into the booth knowing that the size 14 skirt would be perfect; and it was.  The size 14 blouse was too short in the sleeves and tight in the shoulders; the size 16 would have to do even though he would have preferred it to be tighter around the waist.  Malcolm came out of the fitting room and handed his selections to Angie and the others to the floor supervisor.  Angie wasted no time and dragged him over towards the footwear department.

“The fucking blouses button up the wrong way,” Malcolm whined; again pretending ignorance in the matter of female attire.

“No they don’t; men’s shirts button up the wrong fucking way, you lummox,” she quipped, and continued to drag him along by his sleeve.

When they got to the ladies footwear section it was blessedly easy.  Angie went straight to a pair of black, patent leather, high heeled sandals. Malcolm made a stupid gaffe as Angie looked at a size chart,

“Size ten,” Malcolm said, not thinking of the consequences.

Angie spun around and looked him quizzically.  Malcolm blushed a deep red and stammered,

“I read somewhere that women’s sizes are two sizes smaller than men’s.  You know it’s one of those bits of useless information you pick up,” he offered as an explanation.

Angie continued to stare at him questioningly for a minute and then turned back to the rack of shoes and selected a pair of size tens.

“Here; try these,” she said handing him the high heels.

“There’s no one around, just try them on ok,” she warned before Malcolm could offer a protest.

Malcolm sat on a stool and removed his loafers and socks and tried them on; a perfect fit.

“Lovely! I’ll show you how to walk in them tomorrow Malcolm; you will find it difficult but no self respecting whore would wear anything except high heels,” she laughed, regaining her previous joviality.

“Accessories and makeup next!” Angie charged ahead again.

“Accessories? Makeup?” Malcolm quizzed.

“Oh just go to the in store coffee shop Malcolm and I’ll meet you there later,” she tried to feign anger but laughed.

Malcolm did as he was told and Angie joined him about twenty minutes later.  Sipping on a latte she showed him what she had acquired in his absence.  There was a slim gold belt with a silver buckle, a gold clutch purse, a selection of makeup (to which he showed absolute ignorance for sake of appearances), and what seemed to be far too much jewellery for one night’s dress-up.  They finished their coffee and took their selections to the checkout where thankfully Angie presented the purchases to the cashier and all Malcolm had to do was hand over the cash.

Angie again led the way and this time they stopped in hairdressing salon.  Angie explained that it was her favourite salon. And the best hairdresser in town worked there.

“I could take you to a fancy-dress store and rent something tacky or we could go to a novelty shop and get one of those awful novelty wigs but you did say you wanted to look as feminine as possible so I’m afraid you will have to fork out for something good.  On the bright side; if the wig looks good on me too I might buy it off you after the party,” she said.

Angie took charge of the situation and entered into a deep discussion with one of the hairdressers whilst Malcolm stood there with his hands full of shopping bags trying not to look embarrassed.  Eventually he was led into a small room at the back of the hairdressers where he was seated and introduced to Stephan, Angie’s hairdresser.  Angie and Stephen then seemed to have the time of their lives trying different wigs on Malcolm.  They finally both agreed on one, and Stephan held up a mirror so that Malcolm could see.  It was brunette with some lighter highlights; the hair was straight but curved slightly at the neck and fell to just on his shoulders; the fringe just covered his eyebrows.  It was lovely but of course Malcolm just said,

“Well if you think its ok we’ll take it” and paid up.  He made a fuss about the price, secretly pleased that the wig was perfect for the shape of his face.

Outside the hairdressers they parted ways; Malcolm was disappointed when Angie took all the purchases from him,

“It’s not as if you need them until next Friday is it? And as you are coming around my place to for me to dress you properly and make you up I might as well take them home,” she said cheerfully, kissing him on the cheek and walking off towards where her car was parked.

“Thanks for all the help,” Malcolm responded and walked away excited. He could hardly wait for next Friday.

All week the office was abuzz with talk of the party; many of the staff discussed how they were going to dress.  Some were just going to squeeze into their wives clothes; some had gone to costume-hire specialists.  The girls were having a great time rummaging out old flared purple pants, platform shoes and other outrageous seventies pimp apparel. Malcolm kept quiet despite the friendly ribbing that he copped from some of the staff; they joked that boring old Malcolm wouldn’t know a whore from a boar or that he would probably come looking more like a washer woman than a prostitute after last year’s feeble effort.  The only quip that disturbed him was an aside from Eddie,

“She’ll look gorgeous I’ll bet.”

Malcolm didn’t know if Eddie was joking or being sarcastic but he didn’t care; he was too excited and looking forward to the party for reasons that none of his colleagues could imagine; Michele was making her debut!

Friday afternoon finally came and Malcolm drove around to his sister’s place in eager anticipation.  The firm had finished work early and he had a few drinks after work with some of the staff and they had said cheery farewells until later that evening.  He arrived at Angie’s place as instructed at five o’clock having showered and shaved as close as possible ensuring his face was smooth and without a trace of stubble. He had a gin and tonic to steady his nerves before leaving home and Angie greeted him at the door with another.

“To help you relax dear brother,” she laughed and led him through the house into her bedroom.

Angie had unwrapped all of last week’s purchases and they were laid out on her bed; Malcolm get excited just looking at them and gulped down his drink. Angie went to fix him another.

“I’ve been thinking Malcolm; how serious are you about looking as feminine as possible?” she called from the lounge.

“I really want to win the prize Angie; I want to really make up for last year,” he shouted back.

Angie returned with a drink for both of them.

“Well there is only one thing for it then,” she said and reached into a draw in her dresser and held out a pink plastic object that looked like some sort of alien ray gun.

“It’s my Lady Shaver,” she responded to his quizzical look, “were shaving your legs ok?”

Malcolm was now a little drunk and laughed out loud,

“Well if that’s what it takes Angie; let’s do it!”

After a brief argument in which Angie explained that she had seen her younger brother naked when she bathed him as a child.  She also went on to explain that in her eyes seeing a man in his briefs was no different to seeing a man in his swimming costume so Malcolm stripped down to his briefs and sat on the chair in front of the dressing table.  Angie ran the shaver up and down his legs until they were hairless; this was achieved with much howling and complaining from Malcolm who was reminded by Angie that women had to suffer far worse to look good for men; as he was about to find out.  She shaved the hair off his feet and toes and examined her handy work.

“You’ll still have to wear the pantyhose I’m afraid; your legs are lily white and some of those varicose veins look like roadmaps. It’s a trick I used when I was younger when I couldn’t be bothered shaving my legs before a date; just wear two pairs of nylons,” Angie explained.

“You’re the boss,” Malcolm chuckled and took another sip of his drink.

“Ok; sit still, keep quiet and just do as I say and we’ll have you looking like a girl in no time,” Angie laughed and moved in front of him and went to work.

She had quite an assortment of cosmetics laid out on the dressing table along with various sized brushes, sponges and applicators.  Malcolm forced himself to relax and let Angie go to work.  He had made himself up hundreds of times before but now he was going to be made up by an expert so he payed attention to every detail so that he could pick up any pointers.

First Angie patiently painted his finger and toenails; two coats of glossy plumb red.  She told him not to smudge the nail polish before it hardened and went on to explain how women often tried to match their nail polish with their lipstick.

Angie applied a thick coat of foundation to his face and neck and then set it with a liberal dusting of matching face powder.  She then went to work on his eyes.  Next she brushed dark blue eyeshadow onto Malcolm’s eyelids working from the inner corner of each eye to the centre above her pupils. She worked the powder upwards right up to his eyebrows and then she applied a coat of lighter blue out to the far corners of his eyes, lightening the makeup as she worked it up to his brows and blending the two shades where they merged.

“I’m no expert at hooker makeup,” she said, “but I’ve seen enough movies to know that usually go for these garish colours.

“Whatever,” Malcolm said pretending to feign interest whilst paying close attention.

Angie tut-tutted a little and reached for some pink eyeshadow and applied it liberally around the edges of the two coats of blue that she had already applied; blending the eyeshadow with a small brush and making final adjustments with her fingertip.  Malcolm loved the effect and filed the snippet away for future use.

“Ok brother; keep very still now and just close your eyes half-closed for me; here comes the hard bit; the eyeliner.” She said, concentrating on her task.

Angie applied jet black eyeliner to his upper and lower eyelids as close to his lash-line as possible. She started in the very corner of her each eye and worked outwards applying three coats and touching up where necessary so that his eyes were framed by the black makeup.

“Open your eyes; lift your head up but look down at my tummy and keep still for me sweets ok; I’m going to do your mascara next.  I hope you are taking mental notes so that you can touch up your makeup during the evening.” Angie said.

“What do you mean; touch up my makeup?” he asked; knowing full well what she meant.

“We girls don’t stay looking good all night without touching up our war-paint you know” she giggled, “that’s why we spend so much time in the john; why do you think we call it the powder room!  I bought you some makeup yesterday that you can take with you tonight; you can give it to me later as you won’t be needing it,” she explained.

She applied plenty of thick black mascara to his upper and lower eyelashes; fiddling a little as she worked.  She explained that as his eyelashes were very fine she had to apply lots of the product to get a good effect,

“I wish we had bought falsies,” she muttered.

Malcolm laughed inside because he had three sets of false eyelashes at home.

“Ok nearly there,” she sighed and took a sip of her drink.

Angie applied blusher to his cheeks, feathering it along his cheek-line and smoothing it up so that it almost merged with his eyeshadow.  Then she dusted his whole face and neck with a coating of sheer-glow finishing powder, being careful not to smudge her mascara and eyeliner.

“Ok Malcolm I want you to play particular attention to how I do your lipstick; you will definitely have to touch up your lippy tonight,” she lectured.

She opened a long slim box that contained two slim tubes and unscrewed the first tube to reveal a slim applicator coated with plum coloured liquid lipstick.

“This is the first coat and it is long lasting colour; be careful how you use it honey because it is really hard to get it off if you fuck up ok?” she instructed, “so pay complete attention and when you touch it up tonight make sure you don’t go outside of the lip-line that I put on you.”

Malcolm had never used a two-coat lipstick before; he just used ordinary cheap lipstick at home and he paid very close attention as Angie coloured his lips with the first coat of colour and then took the other tube which she screwed at the bottom to reveal what looked more like the lippy he was used to, but slimmer and it was clear not coloured.  She waited a minute and then applied the clear top coat over the base colour coat.

“Perfect,” she whispered more to herself than him, “now leave your lips parted for a second until its dry ok?”

Angie took the brunette wig off the wig stand and brushed it out while Malcolm sat still and let his makeup set and lipstick dry.  After a minute or two Angie put the wig on his head and fiddled with it until it was sitting perfect with the fringe straight.  She brushed it here and there and then stood back to admire her work.

“You look stunning; take a look,” she said, pointing to the mirror.

 The transformation was astounding; from a plain, smooth-faced man he had become a heavily made-up middle-aged whore.  Her brunette fringe framed her dark exotic eyes and her bangs caressed her rouged cheeks and highlighted her luscious red mouth.  Malcolm now started to think of himself as Michele the whore; not as Malcolm, the boring manager of a small department in a small business.  ‘From now on, for the rest of tonight, I AM Michele!’ she convinced herself.

 

“Ok let’s get you dressed then,” Angie said.

 

“You can have a quick drink and get into your pantyhose and knickers you hussy,” she laughed, playfully kissing his cheek.

 

“I’ll step out and freshen our drinks while you do that I think; I don’t want to see your wiggly bits,” she laughed, “put the pantyhose on first then the panties over them ok?  You’ve seen one of your girlfriends put on pantyhose I take it? You don’t need my advice,” she joked; then added as she walked out the door, “don’t ladder the fucking things!”

Michele sat on the edge of Angie’s queen size bed and kicked off her men’s briefs; they now seemed ugly and inappropriate for a lovely whore like her. She eased the pantyhose from the slim packet and slipped the hosiery over her pretty painted toes and slid the sheer nylon up her feet one foot at a time.  She carefully eased the pantyhose up her legs keeping the nylon taught; smoothing out the wrinkles as she went.  She stood up and pulled the waistband of the pantyhose up over her crotch and smoothed the nylon gusset around her midriff to just below her bellybutton.  She slid the red satin bikini panties up her nyloned legs and pulled them snug around her arse and crotch. Michele felt the beginnings of an erection and nearly panicked; but then the though of her sister finding her aroused soon made it go away.

“Ready sis;” Michele called through the door.

“Oh lovely,” Angie joked as she came back into the bedroom with two more gin and tonics.

“Ok let’s get a move on, I don’t want you to be late for your own party,” she said in determined tone.

“Stand up and just do as I say buster,” she joked; but in a tone that bore no argument.

Angie took the red lace suspender belt and adjusted it so that it sat tightly around Michele’s waist and so that the top of garment covered the waistband of the pantyhose.  Next she knelt down and drew the diaphanous black nylon stockings up Michele’s legs one at a time; the stockings sighed their nylon on nylon whisper as they glided over her pantyhosed legs.  Angie carefully adjusted the back-seams so they lay straight and centred along the back of Michele’s legs and then clipped the garters hanging from the suspender-belt to the reinforced stocking tops.  As Angie smoothed the nylons along her legs Michele suppressed the shiver of excitement and felt a little uneasy about experiencing such emotions; especially with her sister’s face so close to her sex organs.  Michele swallowed and tried not to think too much into it. 

Next Angie hooked the brassiere around Michele’s chest and settled the cups into the right position; she walked over to a drawer and took out several pairs of old pantyhose which she stuffed into the cups of the bra to fill them.  Then she had Michele step into the black leather mini which she pulled at and played with until it was adjusted nicely at the waist and the hem was nice and straight at mid thigh; she left it unzipped for now.  Angie handed Michele the leopard-skin nylon blouse to put on while she went to the dresser and took a drink.  She gave Michele a sip of her own drink and put the glass down on the table.  Michele noticed that she had not left any lipstick on the rim of the glass as she often did when she was dressed at home. ‘That two-coat lipstick really works,’ she thought pretending to struggle with the buttons because they were on the opposite side to men’s shirts.  Angie came over and finished buttoning the blouse and tucked it into Michele’s skirt and zipped it up. She buckled the slim gold belt around Michele’s waist and adjusted it so that it sat nicely.

“Nearly there; just jewellery and shoes to go” she sighed.

Angie opened the packet which contained the cheap costume jewellery that she had bought for her brother last week. She clipped silver mounted ruby drops to Michele’s ears and hung a matching silver and ruby necklace around her neck and matching bracelets on both of her wrists.  She put on four large silver rings, two on the fingers of each hand; the rings were set with emeralds and rubies. 

Angie sat Michele back on the bed and slid her feet into the black leather high-heeled sandals; buckling the thin straps which came to just above Michele’s ankles. 

“Now for fuck sake be careful when you walk in these Malcolm,” Angie said; “ lean a little forward and make sure you come down on the balls of your feet first, not the heels, when you walk.  It will take some practice but it’s only for one night.  You should know what we girls have to put with when we wear those fucking death traps anyway,” she chided playfully.

Finally Angie fastened a silver anklet below Michele’s left ankle; another fake ruby glittered as it hung from the thin silver chain fastened to the anklet.

“You’re done honey; take a look in the mirror,” Angie said and helped Michele to her feet. Michele stood up and walked over to the mirror and looked at herself.

She looked stunning; the best she had ever looked dressed as a woman.  She had just the look she wanted; in her mind she decided the look was to be called ‘London streetwalker’ because she looked just like the English prostitutes she saw in the TV shows.  Michele walked over to her sister and kissed her on the cheek and said,

“Thanks Angie; you are a doll.  Oh! One more thing; pin this on for me will you?”

She handed Angie a large white name bar embossed with the firm’s logo in one corner and a Christmas tree in the other; in gold pen script in the centre of the name bar was written: MICHELE NYLONS.  Angie pinned the badge to Michele’s left breast.

“Michele Nylons; cute name,” Angie said.

“Ok Malcolm; err I mean Michele; lets do the last finishing touch.”

Angie went to her dresser and took a small green bottle of the cologne ‘Poison’ and sprayed a liberal amount of the perfume on Michele’s neck and décolletage; then she reached down and playfully sprayed under Michele’s skirt and on her thighs.

“Just in case you get lucky honey,” Angie teased.

Michele blushed a deep red,

“Fuck off Angie!” Michele responded a little hurt.

“Don’t be such a girl Malcolm; here take this,” she said dropping the small bottle of ‘Poison’ into the small gold clutch purse that they had purchased last Friday and holding it out.

“The purse has got powder, eyeshadow, mascara, eyeliner, blush, and lippy in there sweety; so you can touch up your makeup as you need to.  There’s also a hairbrush; everything an old whore needs to ply her trade,” she laughed.

Michele stepped forward and took the purse from her sister and bent to kiss her chastely on the lips to bid farewell.  Angie shocked Michele by pulling her into a tight embrace and kissing her, closed mouth but forcefully, on the lips; then Angie astonished Michele completely by sliding her hand under Michele’s skirt and gently stroking her manhood through her panties.  Angie whispered into Michele’s ear,

“I know about you, you know!”

Michele pushed her sister away and looking absolutely stunned; she gasped,

 

“What do you mean; you know!”

 

“Oh Malcolm; I mean Michele.  I’ve suspected since we were kids.  All the times I found my nylons and panties dishevelled and stained; who else could it have been?  One day I even saw you putting a pair of my pantyhose in your pocket as you left the bathroom.” Angie explained in a soothing voice.

 

“And last week you knew your ladies shoe size; you insisting on wearing a suspender belt; you had those pictures of Transvestites; and you pretended not know that blouses button on the opposite side to shirt.  You sat uncomplaining while I put on your makeup; but the real give away was the way you walk in those high heels honey.  It took me fucking months to master high heels when I was a teenager; and you glide around my bedroom like you were born wearing the fucking things!” Angie finished.

 

“It’s nothing to be ashamed of; your secret is safe with me.  And you look positively gorgeous; if you weren’t my brother I’d fuck your brains out; now get the fuck out here and go and enjoy yourself before I throw you on my bed and ravage you.” Angie pushed Michele towards the bedroom door.

 

Michele was stunned but accepted what she had just heard and realised that she had been stupid to think that she could get away with using her sister to help her crossdress and still keep her secret.  In hindsight Michele knew that she would slip up some how.  Then a question lanced into her head; ‘What did Angie mean about ravaging her? And what the fuck was that passionate kiss and quick fondle all about?’

 

“Angie; are you a lesbian or something?” Michele asked her sister as they walked to the front door.

 

“I’m an ‘or something’ ok; but that’s a conversation for another day; now get the fuck out of my house and party til you drop bitch! Oh; and come around for coffee tomorrow afternoon and tell me all about it!” she laughed and pushed Michele out of the door and into the night air.

 

Michele walked over to her car, stunned at what had just happened; even though she had lost count of the number of gin and tonics she had drunk over the last few hours she now felt completely sober.  She dropped in behind the wheel and her skirt rode up revealing her stocking tops; she smoothed down her skirt and slid her hands along her stockinged thighs and sighed with desire at the feel of her feminine attire.

 

Michele smiled to herself and drove off into the night trying to get her head around the last few minutes.  Eventually she settled down enough to realise that she had been particularly stupid drinking so much alcohol with a three quarter of an hour drive ahead of her from the suburbs to the city; the police were ruthless when it came to alcohol breath testing during the festive season.  She decided to use a little used back road that bypassed most of highway into town; it would put an extra twenty minutes or so onto her journey but she was better safe than sorry.

After she had driven a few kilometres down the dark road she realised that the effects of the drinks she had imbibed earlier had far from worn off; she had to really concentrate and to make matters worse she had never considered the difficulties of driving a car whilst wearing high heels.   Michele checked her mirrors and then reached down and attempted to unbuckle her right shoe so that she could better control the brake and accelerator.  It was a huge mistake; as she struggled with the buckle on her high heel her car swerved violently to the right and she had to correct the vehicle quite quickly on the dark narrow road.  As she gained control of the car and was congratulating herself for avoiding disaster she saw blue and red flashing lights in her rear vision mirror.

“Fuck!” she exclaimed, and pulled her car over into a darkened rest area at the side of the road. 

She followed the small dirt track to series of marked parking bays behind a darkened toilet block and pulled into one of the spaces; she looked around and saw that the rest area was deserted except for her own car and the police cruiser that had now pulled up beside her.  A fat policeman squeezed from behind the wheel of the police car, turned on a large black torch and sauntered over to her driver’s side window; Michele wound down the window terrified.  She didn’t know wether to be more worried about being out dressed up in drag or being over the prescribed alcohol limit.  The fat policeman shined his torch on her face, smiled and said,

“You were all over the road back there miss; have you been drinking?”

Michele summoned up all of her courage and answered,

“I had a couple of drinks an hour ago officer but I’m sure I’m under the limit; I swerved to avoid a small animal on the road,” she lied.

The policeman looked at her for a nearly a full minute shining his torch inside the car and up and down her body and back to her face.

“Jesus Christ you’re a fucking guy aren’t you?” he asked incredulously.

“Yes officer; let me explain…….” and Michele went on to explain that she was dressed in drag to attend a theme party at work.

After listening to her story for a few minute the officer cut her short.

“Well that may be sir, ma’am; whatever.  But I still think that you are under the influence of alcohol and I intend to issue you with a roadside breath test.” He said and waddled back to the cruiser and returned with an alcometer.

He pushed it through the window in front of Michele’s face and said,

“Put your lips on the tube and blow; words I’m sure you quite used to;” he added cruelly.

Michele did as she was told and heard the machine beep rapidly after a few seconds.  She hung her head and contemplated what would happen next.  She would be taken to the police station and have to suffer the indignity of waiting around for bail dressed up in drag.  Undoubtedly the policemen at the station would ridicule and taunt her.  Even worse; what if they put her in a holding cell?  She had read about what happened to some young men in prison at the hands of jailhouse thugs; what chance would she have dressed as she was?  Could she ask for protective custody?  Her head was spinning.

The Policeman took the machine away from Michele’s lips and looked at the reading and smirked.

“You’re shit out of luck tonight sweety,” the cop smiled evilly at Michele through the window.

He turned on his heels and wobbled back to his cruiser; ‘He’s calling it in or whatever they do!’ Michele thought to herself.  She was on the verge of sobbing.  She looked across at the police cruiser and by the light of the dome light she saw the fat cop leaning inside talking on the radio.  Then the flashing lights on the top of the police car went out, closely followed by the head and tail lights.  The cop slammed the door and the rest area became hauntingly dark and deathly silent.  Michele could just make out the dimmed glow of the policeman’s torch as he returned to her car; as he approached she saw he was shading the light with his other hand.  He leaned on the roof of her car and it lurched under his added weight.

“Look honey, I’ve dealt with your type before ok; you don’t do thirty years on the force without dealing with the occasional trannie now and then.  You are in all sorts of problems here; the reading on my little machine there says you’re at least twice the legal limit to be driving.”

“Now, we can sort this out one of two ways; you can accompany me to the police station, and I’m sure the ramifications of that option have crossed your pretty little mind; and also you will lose your license and cop a hefty fine.  Plus I’m betting someone who drives a car like this has a job where a DUI will not be particularly welcomed,” the fat cop droned on.

“Or I can get in the passenger seat there and we can settle this quickly, painlessly; and to both our advantages if you know what I mean?” he finished.

Michele was now totally confused; was there a way out of this?  Was he asking her for a bribe?  Thank god! There was a way out of this! All she had to do was let the cop get in passenger seat and she would hand him some cash and he would be gone.  Yes; it made sense!  He wanted to sit in the car so no one passing by could see her handing him the money; that’s why he turned off his flashers and headlights.

“Well sure officer; get in and let’s settle,” Michele sighed, relieved.

The fat cop had trouble squeezing into Michele’s small BMW but he finally got settled and closed the door.  The dome light went out and Michele heard a rasping sound that she couldn’t quite figure out.  ‘Of course he’s opening the zipper of his wallet to hide the money,’ she concluded.

“Turn on the dome light honey; I want to see you do it,” the cop said.

That made sense to Michele; he wanted to make sure he was giving her the right money; when you take bribes you have make sure the person paying the bribe isn’t ripping you off.  Michele turned the dome light on and turned her head towards the cop and started to say,

“How much?” when she glanced down and saw the policeman’s stubby fat penis sticking out the front of his uniform trousers.

“Well I won’t be long honey; I haven’t had any for ages,” the cop chuckled and reached out and pulled her head into his lap.

Michele was horrified; it finally dawned on her what he had been talking about all this time; she had completely misunderstood his intentions.  These thoughts sped through her mind just as her lips came into contact with the man’s fat smelly cock.  Michele sputtered and tried to move her head but the heavy cop held her down.

“Suck it good babe; come on,” he moaned; and he pushed down harder and Michele had no choice but to take the appendage into her mouth.

Michele sputtered and blubbered trying to spit the fetid member out of her mouth.  Her efforts to get away from the cop’s penis in fact stimulated the glans of his organ as Michele’s lips and tongue lashed at the stubby little cock trying to spit it out.  The cop pushed down so hard on her head that it hurt, and at the same time he pushed upwards, lifting his fat arse out of the seat; Michele had to open her mouth or choke and as she did the whole of the diminutive fat member slid inside her mouth and started to convulse and throb.

Michele gasped as a torrent of semen filled her mouth and then she started to gag.

“Don’t you spit it out bitch!” the cop warned, holding her head down in his lap.

“Yeah baby that’s it; swallow it; oh fuck you’re good! Suck it baby; suck it! I’m coming; oh yeah,” another stream of obscenities issued forth from the policeman as he ejaculated into Michele’s mouth.

Michele was helpless; held over the cop’s small throbbing cock as it continued to flood her mouth with sperm.  She had no choice; Michele swallowed.  The policeman’s secretions were not actually that foul; they tasted musty and creamy.  She sucked and swallowed knowing she had no choice.

“Ok baby; daddy’s finished now; just lick it clean and I’ll be on my way,” the cop chuckled.

Michele realised the worst was over; she licked the fetid member clean and swallowed the last of the cop’s secretions.  The cop lifted Michele’s head out of his lap and leaned over and kissed her full on the mouth before she had time to react.

“Thanks hun,” he whispered in Michele’s ear; then zipped his fly and struggled out of the passenger door.  He walked away towards his police car and waved over his shoulder without glancing back,

“Drive careful now sweetheart,” he shouted and climbed into the police car and drove away.

Michele sat there stunned; she couldn’t believe what had just happened; not only had that fat smelly, little dick cop raped her mouth; she was rock hard in her panties.  What the fuck was going on?

To be continued………………………………………

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The predator had defiled five women so far, all sophisticated, attractive and well dressed ladies in their forties or early fifties. He made a point of that; that they be dressed attractively. He had been known to make his victims get out of bed and apply makeup and dress in their finest lingerie and eveningwear before he spent his time playing his sordid games with them. Some victims reported that he made them parade before him wearing differing ensembles until he was satisfied with how they looked before he ravished them.

The predator had arrived at his current destination by sheer luck. He usually followed his intended victim for a few days, and then planned his attack when he was sure that the victim was alone in her home. Tonight he was returning from a bar and decided to cruise a well-to-do neighbourhood just to see if there was anything special that might be worth following up. He was slightly drunk and stopped his car next to an alleyway separating two townhouses so that he could relieve himself. He ducked into the darkened alley to urinate when he noticed the shadow on blind. The silhouette on the blind was unmistakeable to a predator of his kind; a woman either dressing or undressing; her movements and mannerisms playing out like a shadow-puppet on a movie screen. He couldn’t help himself; he had to see what might be on offer here. When he had splashed the last of the hot stream of his urine against the wall he climbed up onto a garbage bin hoping he would be able to see more through the window.

The predator was in luck and managed to secure a position where he could see through a chink in the blind where it had not been fully extended. The view provided by the chink took in half of a woman’s bedroom. He could see most of the bed, scattered with lingerie and women’s clothing lying in a heap, the coat-hangers still attached to the skirts, blouses and jackets. There had to be at least six outfits lying on the bed surrounded by the small piles of assorted lingerie. He could see a dressing table littered with makeup, perfume bottles, jewellery boxes and the sundry items that women seemed to be unable to do without in their endeavours to look attractive. A wine glass, half full of red wine was set to one side. A small shelf above the dressing table held three wig stands. A blonde bob sat on one wig stand and a black long haired wig sat on the second; the third wig stand was bare.

The predator was pleased to see that this woman had such good taste in clothing and obviously looked after herself. The mountains of lingerie, makeup, jewellery and the wigs bespoke of a woman who was most attentive to her appearance – the sort of woman he fantasised about.

The predator allowed his eyes to consume the sight before him. The woman presented herself sideways to him, sitting in front of the mirror at the dressing table making final adjustments to her appearance. She looked to be in her early forties, solid but not fat, and dressed just to his taste. His eyes started with her face and worked their way down her body. Straight brunette hair hung just to her shoulders, the fringe framing her heavily made-up eyes; her cheeks were rouged, her lips full and painted plum red. A glint of light betrayed the simple sparkling earrings that undoubtedly matched the diamante necklace around her neck. She was wearing a black nylon full-slip, the rise of her small breasts emphasised by the tight bodice, the laced hem of the slip resting on her sleek nyloned thighs just above her knees.

The predator liked the way her taupe stockings glistened in the lights from the makeup mirror. Her hands slid down one leg, her fingernails painted a matching plum red to her lipstick, and adjusted her stocking; pulling the sleek nylon taught on her shapely leg and momentarily disappearing under the hem of her slip as she adjusted the clip on a garter strap. The predator shuddered. His eyes continued down her leg and lingered on the black, patent leather, open toe high-heels and he caught a glimpse of her painted toenails on display, encased in the gossamer of her sheer stocking, as she waggled her foot back and forth back as the admiring her own pretty foot. She stood, and then advanced towards the bed presenting herself front-on to the predator.

The predator took in the whole visage of the woman that he had now determined was to be his next victim. Mature, attractive, heavily made-up, tall and well built; she was just to his taste. If he had not spent the evening in the bar and was in a sober frame of mind he might have been more cautious, but the sight she unknowingly presented to the predator sealed the woman’s fate. The predator slid silently off the garbage bin on which he had been standing and made his way back to his car. He scanned the street and saw no one. Most of the lights in the adjoining townhouses were out and the street was quiet. He checked his watch: 11:30pm, perfect he thought, and reached into the back seat and took out his burglary tools. Fuck the risk! He had to have her. Now!

Michele sat before the makeup mirror twirling the wine glass in her fingers watching the light sparkle in the red Shiraz. The dark red wine matched the colour of her fingernails and she briefly giggled to herself at the complement. She was slightly drunk from the half-bottle of wine she had already consumed and she set the wine glass down carefully and began to add the final touches to her makeup.

Michele was actually Michael, a divorcee in his mid forties who lived alone and had come to transvestism late in life after suppressing an urge to crossdress for most of his adult years. Like most crossdressers he had urges to dress-up and become a woman for short periods of time and often dressed in his wife’s underwear when she was away. After an amicable divorce some five years earlier, Michael now transformed into Michele whenever it pleased him to do so. Living alone and having the privacy to dress when it suited him, he had developed the persona of Michele over a period of years.

Michele’s male alter ego had fought a battle with his weight for most of his life and he had allowed himself to balloon out during the later part of his marriage. When the opportunity to fully crossdress whenever he felt like it presented itself, Michael decided he didn’t want to look like a middle-aged frump. He dieted and exercised until he could eventually fit into a size 16 and some times even a 14; a great effort given his large frame, and he now carried very little fat.

Michele had acquired an extensive wardrobe, first at opportunity shops and later at larger specialty shops; insisting to the shopkeepers that he was buying the clothes as presents for his wife. Lingerie was easy to buy as it is never considered unusual for men to buy nice underwear for their wives or lovers.

Michele bought his first pair of women’s shoes from an opportunity shop and once he knew his woman’s shoe size he purchased many styles of high-heeled pumps and sandals; again insisting to inquisitive shop assistants that they were presents for his wife. He sometimes had the boxes gift-wrapped to maintain the façade.

Michele had dabbled with his wife’s makeup with various degrees of success and failure during the years of his marriage and easily obtained all the makeup he needed by purchasing a couple of complete makeup kits ("its for my niece’s birthday; she’s just turned thirteen") and then simply added to his makeup collection by throwing any item he desired in with the week’s groceries; no one ever questioned him at the checkout; husbands just picked up whatever their wives had written on the shopping list after all.

Michele could purchase women’s jewellery easily of course, but his biggest problem was how to get his hands on some nice wigs. The problem was solved when he was sent to a large city interstate on a business trip where he visited the part of town frequented by the gay community. Here a sympathetic old lady in a wig shop who was used to dealing with ‘his kind’ helped him pick out and try on three different styles and hair colourings. He purchased the wigs and then went into another ‘specialty shop’ where he bought breastforms in two sizes.

Michele loved being Michele; Michael transformed into her at every opportunity and spent most evenings and weekends dressed and fully made-up. More and more often though he had been fantasising about taking his transvestism a step further; whenever he was dressed as Michele he became aroused, he always had, but for the last year or so he had fantasised about being with a man. He did not consider himself gay; in fact when he wasn’t Michele his sexual fantasies revolved around women; but when he was Michele he wanted to be with a man or to have a ‘lesbian’ encounter with another transvestite.

Michele was terrified that her secret life would be exposed. When dressed she kept the doors locked, the shades closed and never answered the door. Although she had become adept at applying makeup and dressing en-femme, and she believed that she made quite an attractive mature woman, she would never dream of going out dressed as Michele. She contented himself with reading books and looking at magazines and movies where transvestites had hot sexual encounters with each other and with male admirers. Although masturbation bought relief, Michele longed for ‘the real thing.’ She was thinking a lot lately of either placing a discreet ad in some of the sex shops she visited or advertising her availability in a contact magazine or in some of the internet chat rooms she frequented.

Michele was not aware that she was about to have her first encounter tonight, nor that the Predator would be her first man. The Predator was not aware that the woman he lusted after, as he spied on her through her bedroom window, was in fact Michele; a transvestite.

Michele had opened a nice half-bottle of Shiraz earlier in the evening and then poured herself a warm bath. She painted her toe and fingernails and allowed them to dry and then poured herself a glass of wine and stepped into the steaming, scented water. She spent a luxurious hour soaking, during which she had shaven her legs and chest and closely shaven her face. She had also drunk three glasses of wine.

Michele towelled herself off and carried a full glass of wine from the ensuite bathroom into her bedroom where she sat at her dressing table and looked at herself critically in the mirror. She was showing her age but was still respectable and with the magic of makeup would soon be transformed into a presentable, if slightly sluttish, middle-aged woman. She giggled to herself and realised she was slightly drunk.

Michele went through the labour of applying her foundation; she had a product from Max Factor which closely matched her skin colour but covered up the few scars and blemishes that she had acquired during in her life. Next she liberally coated her face and neck with face powder one shade darker than her foundation; she now had the blank canvass she liked to achieve prior to applying the rest of her makeup. She loved this next part; the application of colours and shading which changed the whole look of her face from bland maleness to feminine fox. She giggled again and took a gulp of wine before continuing.

Michele applied her eyeliner next. All the books and magazines in which she had read makeup tips said you should do this later but Michele had learned that this was the hardest part of applying makeup and if she screwed it up (which she often did, especially after drinking), she could wipe the eyeliner away, apply more foundation and start again without ruining her eye-shadow and mascara. The eyeliner was applied liberally to her upper and lower eyelids, from the inner corner of her eyes to the outer corners, gradually thickening the line as she went. Having achieved the desired result she looked for a suitable palette of colours for her eye-shadow.

Michele selected a pale blue which she applied to her eyelids and then blended it into a shade of dark pink which she brushed onto the upper part of her eye sockets and right up to her eyebrows. She wished she could shape her brows but that would be too noticeable to her workmates, family and friends so she just kept her brows neatly plucked. Next she rouged her cheeks to define the lines of her cheekbones. She used more rouge and eye-shadow than is the fashion nowadays but she preferred the more colourful makeup styles of the eighties over the current subdued ‘less is more’ look.

Michele next applied a light coating of ‘skin-glow’ face powder all over her face and neck to set the makeup she had already applied and to give her face a subtle radiance. She carefully brushed lashings of mascara onto her lower and upper eyelashes. She knew from painful experience that if she put too much mascara on her lashes that it would congeal and look unsightly; even worse it could end up ruining her eye-shadow or face makeup if globs of the mascara came loose from her lashes. She did like to wear lots of mascara though and found a Maybelline product that did not clot and was easy to apply.

Michele took her time putting on her lipstick. Having completed the rest of her face she didn’t want to ruin the effect with a sloppy job. She took time to line her thin lips just outside her lip-line so that her lips would seem fuller; she also knew that the wine she had drunk was having its effect and realised that caution here would save her tears of frustration if she slipped and made a mess of her lipstick. The colour was a deep plum red and matched the nail polish that she had painstakingly painted on her toe and fingernails prior to her bath.

Michele reached up and studied the three wigs sitting on their stands. ‘The brunette,’ she thought to herself and lifted the wig from its stand. She brushed the wig with the special brush that she been advised to purchase by the nice old lady who had sold her her wigs. She started her brush-stokes at the extremities of the hair and worked her way up to the crown, admiring the sheen of the artificial hair. She positioned the wig on her head and adjusted it so that her fringe was straight and hung level with her eyebrows.

Michele looked in the mirror and admired her transformation. ‘I look quite attractive’ she thought; ‘I bet Michael would like to fuck me’ (she giggled to herself at the absurdity) and reached for her wine glass.

Michele went to the closet located on the right-hand side of the bedroom; Michele’s closet. The closet on the left was Michael’s closet and contained his suits, shirts, ties and boring male underwear, socks and shoes. Michele’s closet contained the soft, luxurious, feminine attire that so excited her. She rummaged through the lingerie draws and threw a pile on the bed; next she took down half a dozen ensembles and threw them in the centre of the bed amid the strewn underwear. It looked like a messy, awkward way to select an outfit but it worked for her. She would often get nearly fully dressed and then change her mind and she had found over the years the best method for her was to take a selection of clothing and throw it on the bed and then once she had finished dressing, put away whatever clothing she had decided not to wear.

The predator at this time was just leaving the bar having been unsuccessful in locating a suitable woman as his prospective next victim. He had drunk more than usual, and frustrated at not finding his next target, stumbled to his car and took off towards the better part of town to prowl for a fitting quarry to stalk.

Michele tore open a packet of cheap flesh-toned sheer to the waist pantyhose. She wore pantyhose as a foundation garment to help flatten her tummy, hold her male genitalia out of the way between her legs, and to help cover the small nicks and varicose veins on her forty-year-old thighs and ankles. She felt a small tingle of excitement as she smoothed the pantyhose up her legs and over her tummy and buttocks. She carefully manipulated the sheer toes around her painted nails ensuring she didn’t ladder the cheap hose.

Michele selected a pair of red nylon full-cut panties from the midden of lingerie on her bed. She stepped into them and slid them up her nyloned thighs, savouring the rustling sound of nylon on nylon. She adjusted the waistband on her hips so that the cute little lace bow was centrally located below her belly button. Michele could not understand the modern woman’s obsession with thong panties; they were uncomfortable and unflattering on women of her solid build. Besides she liked the way the tight nylon panties caressed her buttocks.

Michele next chose a black satin garter belt; her mother had called them ‘suspenders’ she remembered. She clipped the garment together and stepped into it carefully pulling it up her hosed legs and over her panties so that it sat snugly around the bottom of her waist. She carefully adjusted the garter straps ensuring they did not snag her pantyhose.

Michele decided on a matching black satin bra, again clipping the fastenings at the back of the bra together before donning the garment. She giggled yet again when she thought about all the troubles she had had as a young adolescent Michael attempting to undo his girlfriend’s bra so that he could caress her budding teenage breasts. She took another sip of wine and pulled the garment over her head, adjusting it on her chest in the mirror and straightening the straps on her shoulders. She had breastforms if she wanted to use them but this bra was slightly padded and with her ‘man boobs’ gave her a pleasing if subtle cleavage without being overly busty (although sometimes, when she was in the mood, she liked to stuff her bra with the largest set of breastforms she had and parade around like Mae West).

Michele dithered over which stockings to wear; it would depend greatly on which ensemble she finally decided upon. Should she wear black, grey, taupe, flesh-toned; fully fashioned, Cuban heeled or sheer toe? She had so many pairs! She settled on a pair of high sheen taupe lace tops. She loved the way they emphasised her shapely legs, and with the flesh toned pantyhose underneath the stockings, her legs would look magnificent. Michele thought her legs were the best part of her body. She slid the stockings on and connected the clips on the garter straps to the lacy stocking tops. She reached for her jewellery box and selected faux diamond earrings and a matching pendant necklace. As she clipped the earrings to her ears she lamented the dearth of good quality clip-on earrings. She dare not pierce both her earlobes as it would be too noticeable to others.

Michele went back to her closet and selected a pair of black, patent leather, open toe high-heels and placed them beside the chair next to her dresser. She chose a black nylon full-slip from the mess of lingerie on the bed and pulled it over her head being careful not to ruin her makeup or hair. She smoothed the garment to her body, the tight bodice clinging to her breasts and hips and the skirt flaring around her thighs, occasionally sticking to her stockinged legs because of the static electricity. She loved the feel of the lacy hem; like butterfly wings brushing on her thighs.

Michele sat down in front of the dressing table and slipped her feet into her high-heels; although a size eleven her feet were not grotesque because they matched the proportions of her body. After all she was a small size eight in men’s shoes and her feet were considered quite small for a man. She turned her chair sideways to the dresser so that she could adjust her stockings; she pulled the sleek nylon taught on her shapely leg and her hand disappeared under the hem of her slip as she adjusted the clip on a garter strap. She waggled her right foot from side to side, admiring her own pretty feet in the high-heels and appreciating the gleam of the lights on her high sheen stockings. Little did she know that she was not the only one admiring her legs and feet!

Michele stood and advanced towards the bed to select an ensemble for the evening. She finally decided on a white ‘Carla Zampatti’ A-line skirt and a mauve satin long-sleeved blouse she had purchased from Supré. She always wore long sleeved blouses or jackets because although she kept her fingers and the backs of her hands free of hair, she could only lightly shave her arms with a beard trimmer. Her tanned arms had only a light sprinkling of fair hair but she felt that fully shaving them would be too noticeable when she wore T-shirts and Polo’s when she was Michael.

Michele donned the blouse, fumbling with the buttons; she was still not used to them being on the opposite side to men’s shirts. Then she stepped into the skirt and pulled it up around her waist, tucking the blouse into the skirt and closing the zipper at her waist. She went back to her dresser and mooched through the jewellery box and decided upon two matching silver bracelets for her left wrist and a silver amulet set with a large black opal for the right. She slipped a matching opal ring set in silver on the ring finger of her right hand and a diamante ring set in white gold on her left ring finger.

Michele pushed her hands out before her and admired the effect of the jewellery against her slim wrists and her plum-red painted fingernails; she had taste she thought, but she still projected that slightly sluttish style she favoured. She looked at herself in the mirror and was pleased with the result. She twirled around and admired her ample but well-proportioned bottom; the A-line skirt was a snug fit. She drained her wine glass and tottered on her high-heels as she started from the bedroom to the kitchen to open another bottle of wine. She was drinking a lot lately; but what did she care? As long as she kept her weight in check; it’s not as if she had a boyfriend to keep sober for. She sauntered down the hallway towards the kitchen, her heels clicking on the slate tiles as she did her best vamp imitation, swinging her buxom sexy bottom from side to side and giggled to herself again.

The predator had let himself in easily through the kitchen window whilst Michele was making the final adjustments to her clothing in the bedroom. The kitchen window looked out over a small garden, dark at night, and well hidden from the main road; the lock was cheap and easily defeated. The predator was silent as he climbed through the window and dropped soundlessly to the tiled floor; he’d had plenty of practice after all. He heard the clatter of high heels on the tiles and a little giggle from the hallway. ‘Oh this bitch would not be giggling for long!’ he thought, as he hid behind the opened door that led into the kitchen from the hallway.

The predator quietly lowered the bag containing his burglary kit to the floor and reached inside it to take out a gag and a pair of handcuffs. He didn’t like using the gag on his victims because it ruined their lipstick and distended their faces. He liked to look into their pretty faces while he did things to them, and once they learned resistance was futile (and they all learned that lesson pretty quickly) he liked to kiss them. The woman who had excited him enough to risk what he was about to do had affected him strongly; he wanted to take her as soon as possible, his member was so hard that it was uncomfortable in his pants. He would take her quickly in the kitchen and then they could retire to her bedroom for the rest of the evening’s entertainment. he thought to himself.

The predator heard her high-heels getting louder now as she approached the kitchen door and his drunken mind reflected on his last glimpse of her before he had jumped down off the perch outside her bedroom window. Her heavy makeup, the black nylon slip in contrast to her sheer taupe stockings (he preferred women who wore stockings instead of pantyhose), and those shiny black open-toe high heels. He would take her fully clothed, right here in the kitchen; he would take her in such a way that she would know he was in charge and that resistance was futile. He would take her in a way that a woman of her breeding had probably never experienced before.

Michele walked into the darkened kitchen and headed straight for the wine rack above the breakfast bar. She didn’t bother turning on the light as the light spilling in from the hallway was ample for the task; besides she hadn’t closed the curtains in here and even though her kitchen window was not in open sight of the road she was still paranoid about anyone seeing her dressed en-femme. She was thinking of whether to open a bottle of Shiraz or merlot when she felt herself being pushed heavily from behind and she collided heavily with the kitchen table.

The predator pounced on her when she was halfway across the room. He used his weight and strength to propel her towards the kitchen table. She was a big woman and he was taking no chances; as she crashed into the table he pushed her shoulders down and pulled her hands up behind her back and clamped the handcuffs on her wrists. He lifted his knee and slammed it into her well proportioned behind to hold her against the table and pulled up on her cuffed wrists. As expected, she pushed her upper body upwards and back in an effort to escape, but this only assisted him. As she rose up and gasped, a prelude to either to a scream or cry for help, he pulled the ball bag over head and into her mouth, securing the straps tightly around her neck. He now had her where he wanted her.

The predator pushed down on her shoulders so that she was bent over the kitchen table. In the dim light he could now see her mauve satin blouse and the white A-line skirt; subconsciously he approved of her style, he loved it when they dressed nicely for him. He wasted no time. The predator kicked her heels apart so that her legs were spread as far as the tight skirt would allow and released one of his hands from her cuffed wrists and undid his flies and released his erect organ.

The predator was extremely aroused and he could smell the stale alcohol on his own breath as he panted in excitement. He reached under the woman’s skirt with his free hand and grasped the waistband of her panties and yanked them down. He was puzzled when her panties came to an abrupt halt at the top of her thighs and then he realised that she was wearing her garter belt over her panties and because of this her panties could be lowered no further without releasing the clips on the garter straps attached to her stocking tops. It didn’t matter, her panties were down far enough for him to carry out his intentions.

The predator stepped in close between her splayed high-heeled feet; his crotch close to her buttocks, one hand gripping her handcuffed wrists and pushing her body down hard on the kitchen table, the other hand under her skirt pulling her panties down so that they bunched around her thighs. He bought his free hand out from under her skirt and spat in the palm of it; then he spread the glistening spit over his tumescent penis, ensuring his glans was completely lubricated.

The predator lifted the woman’s skirt up and thrust forward. His cock came up against a membrane of sheer nylon, and for a moment he couldn’t figure out what had happened. Was the silly bitch wearing two pairs of panties? Then he figured out what was preventing him from reaching the object of his desire; it was the gusset of the woman’s pantyhose. The dumb cunt was wearing pantyhose under her stockings! Why the fuck would she do that?

The predator took no time to try to answer these questions, he was now so stimulated that he was close to climax. He pushed forward with his hips and felt his member force the nylon membrane of the pantyhose into the crease between the woman’s buttocks. He pushed harder still and felt his glans nestle into the woman’s anal bud, her silken hose wrapped around the sensitive head of his penis stimulating it into bringing forth a trickle of pre-seminal fluid; the clear liquid combining with his spittle to further lubricate his member. He grunted and pushed forward with all his bodyweight and actually felt the heavy table move an inch or two as he thrusted.

The predator felt his iron hard cock tear through the gossamer thin pantyhose gusset and then slam against the woman’s tight sphincter. His cock paused briefly at her resisting puckered entrance, then his weight and the lubricant did their job and his shaft slid slowly and steadily inside the woman’s tight back passage. The Predator’s crotch slammed hard against the woman’s soft round buttocks and his scrotum rested in the silken purse of her bunched panties stimulating him to extremis. He ground his crotch in a circular motion against the woman’s lovely soft arse and pulled her back hard against him and unloaded stream after stream of hot semen into her tight channel.

The predator howled and shuddered as his orgasm shook through his body; he ground his hips harder against her and stimulated his scrotal sac by rubbing it against the silken gusset of her pantyhose. His climax over, he pushed the woman forward and pulled back from her. He watched in awe as a trickle of semen seeped out of her and ran down her thighs, staining her stocking tops and pooling in the crotch of her panties. He had only just started with this bitch; he was going to have some fun tonight!

Michele lost all thoughts of red wine as she was propelled forward and slammed hard against the heavy wooden kitchen table. She was confused as to what was happening; her thought processes slow and fuzzy because of the wine she had drunk. She realised a stranger was in her house and that she was being pushed down across her own kitchen table but couldn’t figure out why. For one second she stupidly panicked at the thought that someone had found her dressed as a woman; and then a split second later she realised that she had a lot more to worry about than the exposure of her transvestism. She realised she was in serious trouble when she felt the handcuffs clamp on her wrists.

Michele’s fighting instinct took over and she used all her strength to lift her body up off the table so that she could yell a protest to the man who was assaulting her. She understood now that the perpetrator believed he was dealing with a woman; if she could just let him know that he had handcuffed a man, not a woman, maybe the intruder would let her go, or at least think twice about what he was about to do. Maybe she could negotiate with the trespasser; offer him money, her car, anything to get him out of her house without any further indignity.

Michele never got a chance to say a word; as soon as she opened her mouth the rubber ball gag was pushed into it. She started to hyperventilate, being forced to breathe in and out through her nose; then her chest was slammed downwards on top of the kitchen table and she couldn’t move. She stumbled as her heels were kicked apart and her legs spread to the full extremity allowed by her tight skirt. The home invader held her tightly against the table so that she wouldn’t fall, and then terror struck her she felt his hand reach under her skirt.

Michele was horrified at the prospect of what was about to happen to her. A glimmer of hope surfaced; he would realise she was not a woman and let her go, surely! Then she felt him yank her panties down and was actually relieved when her panties entangled in her garter straps and would go no further. As soon as the pervert reached under her to touch what he thought would be female genitalia he would be in for a terrible shock. He would be shocked by what he found there and would stop what he was doing. He would be disgusted to find out that she was a transvestite and may even beat her, but at least he would stop this perverted attack.

Michele’s glimmer of hope faded when she heard his flies unzip and the sound of him spitting into his hand. She was about to attempt one last struggle when her attacker’s full weight pressed against her backside pinning her to the table. She screamed to herself in her head as she felt her skirt being raised and the gusset of her pantyhose stretch as her attacker’s penis nestled in the bud of the entrance to her back passage. The fool didn’t realise she wasn’t a woman! He thought she was the lady of the house and he intended to defile her in this despicable manner to gratify his primal urges! Then she felt her attacker’s hard hot member tear through her pantyhose and begin to invade her.

Michele screamed into the gag at the intense pain as the hot cock forced its way inside her. No sound would issue forth around the gag but that silent scream would live in her memory for a long time. The man’s member slid slowly but inevitably deeper and deeper inside her; surprisingly after the initial shock and intense pain she felt as he had entered her, the feel of the invader’s lubricated penis became less painful; it just felt uncomfortable and filling.

Michele felt the intruder’s crotch press hard against her soft buttocks and realised with some relief that he was now fully inside her. She felt him pull her soft bum back hard against him and the gyrations of his hips as he worked his turgid member around inside her tight passage. Then she felt the hot gush of his semen as he spent himself deep inside her; she heard his groan and could smell the stale alcohol on his breath as he bayed and howled with his climax.

Michele was absolutely astonished at what happened next. As her defiler’s glans pulsated and throbbed against her sensitive prostrate, washing it with his hot seed, she felt a stab of exquisite sexual pleasure pulse through her lower regions and she simultaneously stiffened and ejaculated into the crotch of her pantyhose. She couldn’t suppress the pleasure she felt even though she felt utterly debased. She collapsed against the kitchen table as her orgasm subsided and she felt her attacker pull himself slowly out of her and was surprised that it did not hurt but in fact was mildly pleasurable.

Michele could feel that the tight bud of her back passage was left slightly open after the ravaging it had taken and she felt her attacker’s warm sperm run out of her and down her thighs where it pooled in her panties and stained her stocking tops. The front gusset of her pantyhose was soaked with her own spend whilst her attacker’s semen ran down her thighs into her bunched up panties. Her head was spinning with the realisation of what had just happened to her; then she began to wonder what would happen next.

To be continued…………………………………