I was sitting at the desk in my den, wearing one of my nicer black suits, when I heard a knock at the door. She was told to only come in when dressed and in character. The show was about to begin. "Come in" I said, eagerly awaiting the appearance of my "student".



She slowly made her way through the doorway to the center of the room. She was not even quite 5 feet tall, weighing in at about 90 pounds soaking wet; a 21 year old body that would make a fitness model jealous. Her medium length blond hair was in pig tails and she wore bright pink lipstick. She had an unbuttoned white blouse tied up underneath her proportionate B-cup breasts. Just below her perfect belly was red plaid pleated skirt that could barely qualify as clothing. The garment started about a 1/4 inch above her pelvic bone and traveled only about 2 inches past her brazilian waxed pussy and butt. Firmly snug around the bottom of her toned thighs were the tops of her white stockings, which led down to her black 3 inch heels. Her cheeks were already rosey with embarrassment. She was not this type of girl. She would be tonight though at my orders.



"You wanted to see me Mr. Jackson?" she asked in her best schoolgirl voice.

I was pleased with this sight, but I wanted to see the rest. I quickly said to her, "Yes, get me my notebook from the bottom drawer of that cabinet."



She walked with tiny steps to the cabinet, her sexy hamstrings twitching with every step. Normally she would have squatted down to retrieve the notebook, but she knew what was expected of her. Instead she briefly paused then bent over at the waist to get it, displaying her perfect ass. It was so firm and tiny that every stitch of fabric on her white thong that covered a sliver of her ass crack was visible. After a few seconds of frantic searching, she stood erect with the notebook, walked back to the desk, and laid it in front of me.



"There you go Mr. Jackson" she said.

"Jennifer," that was her name tonight, "we need to talk about your grades. You are failing my class! Not even your final exam could give you a passing grade. You need to take your education more seriously!"

"I'm sorry," she stammered, "is there anything I can do to pass?"

"I don't think so, you are just too far behind." I responded.

"Please Mr. Jackson, I'll do anything!" she pleaded crossing her fingers together and bending slightly at the knees.

"Anything?" I said devilishly.

"Yes..." she replied nervously, unsure of what she was agreeing to.

"OK then... I have a very special lesson for you... you want some extra credit?"

"Yes, please Mr. Jackson."

"Alright, come over here" I motioned her to my side of the desk.



She walked around the desk carefully, keeping her hands on the bottom of her skirt to stay covered. As she approached me, I put my hands on her hips and positioned her standing between me in my chair and the desk.



"I teach a few subjects. If you can pass a small test in each one, I will improve your grade each time. How does that sound?"

"That sounds great Mr. Jackson", always saying my name as though I was a drill sargeant.

"OK then, it's time for your first test. Its an easy subject: basic arithmetic"

"I can do that" she said.

"Glad to hear it... now lay back on the desk" I instructed.

"What?!" she said shocked.

"Do as you are told or you will never pass this class... now lay back on the desk!"



She looked into my eyes briefly as I observed in my chair and then did as she was ordered. She put her hands on the edge of the desk, boosting her tiny frame onto it. Her bare ass cheeks were against the cold wooden desk. She then slowly laid back on the desk leaving her legs together, dangling from the edge, her pigtails hanging over the opposite side of the desk. Unpleased with the conservative position, I stood up from my chair, roughly grabbed her ankles and put them on the edge of the desk. She was now exposed like a gyno exam and mortified, her thong her only barrier. She covered her face with one hand and tried to pull her skirt down over her thong with the other.



"Put your hands on your tits" I coldly ordered.

She was always squeamish about dirty talk. With obvious shame in her eyes, she complied with my request.

"Now close your eyes and we'll begin your first test."

She closed her eyes, her knees instinctively trying to go back together, only to be pushed apart again by me.



Wasting no time, I took my left hand and pushed the fabric of her thong to the side, displaying her tight pussy and giving a glimpse at her virgin asshole. She flinched from the sudden exposure. I then laid my right hand flat over her vagina, sliding it slowly back and forth, feeling her juices start to flow. Her breathing started to speed up. Then, with a slow push, I inserted my middle finger completely into her pussy. She let out a soft moan and then I said to her:



"How many fingers are in your pussy?"

"One Mr. Jackson" she replied sexily.

"Very good Jennifer" I said as I started to rock my finger in and out of her pussy getting it sopping wet in only a few seconds.

"ready for your next question?" I said.

"God yes Mr. Jackson!" she replied ecstatic.



Staying in the rhythm of my finger fucking, I seamlessly slipped my index finger in her along side my middle finger. She responded with a short grunt followed by heavy, staggered breathing.



"How many fingers is that Jennifer?"

"It's... 2... Mr... Jackson!" she responded, each word coming out with a heavy breath.

"You're doing well Jennifer"



Her pussy was now dripping juice onto the desk and she was starting to slowly squeeze her tits as she was fingered. Pretty amazing considering this girl never had sex with the lights on before I made her my toy. But her pleasure was not my goal. Her unwilling submission was. To that end, as she squirmed back and forth from the sensation, I decided to quickly force my ring finger into her untouched asshole. Her pussy juice running down her ass, her relaxation, and her gyrating hips created the perfect storm of circumstances that allowed my finger to penetrate her virgin hole completely. She yelped in pain and became motionless, except for her hands which flew from her breasts and attempted to push mine away.



"Put your hands on your tits" I said mechanically.

"But... it hurts!" she cried, breaking from her little schoolgirl voice.



Ignoring her loss of character, I stayed in mine.

"Fine, then you fail my class!" I said, looking at her disapprovingly.

"I... I..." she stammered in labored breaths. With her will broken long ago, she did what she was manipulated to do.

"Yes... Mr. Jackson"

"That's better. Now how many fingers are in your pussy?"

"2" she said quickly, hoping her asshole would soon be left alone.

"That's good. Now how many fingers are in your ass Jennifer?" I said slowly.

"1... Mr. Jackson" she said shamefully.

"Very good Jennifer, now there's just one more question."



I removed my fingers from her pussy and ass elliciting a sigh of relief from my sex toy. I grabbed her by the butt and stood her in front of me. She looked away from me, still embarrassed from having her asshole penetrated. I pulled her close to me, still gripping her ass, and pushed my stiffening cock into her belly. I leaned into her ear and said:



"How many inches is my cock?"

She looked up at me unsure. She knew I was huge for her, but had never guessed a measurement.

"This is an open book question Jennifer" I said leading her along.



She gave me half a smile and looked down at my crotch, her hands starting to undo my zipper. She reached her tiny hand inside and pulled my semi-hard cock from its cage. Without hesitation she began to pump me with both hands like she was churning butter. Quickly I was fully erect, my manhood as thick as her wrist. She had never inspected my member so closely and actually seemed shocked at the size.



"10 inches Mr. Jackson?" she guessed.

"Close enough Jennifer, 9 1/2. Well done! For that my dear, I can bump your grade up to a D, but I bet you aren't satisfied with that are you?"

"No Mr. Jackson" she replied.

"Good, then on to the next test: Engineering"

"Sounds tough Mr Jackson."

"Don't worry Jennifer, you'll do fine. Now back on the desk."



She released her grip on my cock, letting it fall and rattle like a diving board. She quickly boosted herself back onto the desk and laid back like before, still keeping her legs together.



"Now Jennifer, using only your legs, show me what a L joint looks like."

Pausing for a second to think, Jennifer then lifted her closed legs in the air, pointing them straight to the ceiling. Her perfectly toned legs and ass were on full display.

"Excellent Jennifer! Now show me a 45 degree angle"



She paused again, this time because she knew how exposed she would be. Still, under my spell, she tilted her legs back even further til they pointed at the wall behind her. Her ass came off the desk and her cheeks spread apart. Her thong was hanging on for dear life, revealing the edges of her asshole on either side of the thin fabric.



"Now Jennifer, " I said as I pulled her hips and brought her tender ass to the edge of the desk, "how much force does it take to put a rigid member in a small elastic opening?"

"I... I... I don't know" she said puzzled.

"Let's find out"



I yanked her thong from her hips to her knees, still up in the air. Pushing forcefully on the back of her legs I drove her knees down to her chest. Next I grabbed her by the wrists and forced her to cuff her own legs. She grabbed the opposite elbow on each arm and kept her extended legs pinned to her chest as though she was an olympic diver. With one hand on her hip and the other guiding my massive cock, i pushed deep into her pussy. She gasped as the mouth of her vagina split to 3 times its normal size. Though only 4 inches deep, the shear girth of my cock sent her into a near seizure of discomfort and arousal.



"You're... huge... Mr. Jackson!" she grunted through my steady pumping.

"I know Jennifer. Let's see how much force it will take to go all the way in"

She gave me a look of nervousness that quickly turned to pain as I thrust my hips forward into her womb. She let out a scream as my cock pushed against her cervix, still an inch from reaching full depth.

"How much force does it take Jennifer?" I asked heartlessly.

"This.. much... Mr. Jackson!" she said in a painful tone.

"Very good Jennifer, I think you've earned a C now. Want to go for a B?" I asked, as though she had a choice.

"Yes... Mr. Jackson"



As I rocked in her pussy, she slowly began to adjust and the pain became overwhelmed by the sexual sensation, but it still hurt. She started to like it, so it was time to stop. Her pleasure was not a priority, in fact, quite the opposite.



"Now its time for your Anatomy test. This is a 2 parter. The first part is hands on. The second will be an oral exam. Now get down on your knees" I said smirking, knowing what I had planned.



She could have blown me standing with our size difference, but I wanted her on her knees. She slowly lifted herself from the desk. In one smooth, but hesitant motion, she slid from the edge of the desk down to her knees in front of me looking directly at my dick. I could feel her hot, nervous breaths on the end of my penis. Her tiny white panties were still resting around her knees.



"Take my cock in your hand."

She quickly complied, grabbing at the base of my shaft. It looked as though she could fit 4 of her hands on it at once.

"When I say a body part, I want you to hit your body part with my cock. Make sure you hit it a few times so I know for sure." I instructed.

"Yes Mr. Jackson" she seemed ready for this one.

"OK, let's begin. Where are your breasts?" I asked.



She got herself straight up on her knees to bring her chest out towards me. With gentle taps, she identified her breasts, hitting herself above the nipples.



"You can do better than that Jennifer. Now where are your breasts."

She did the same again, this time hitting herself a little harder, enough to make some light slapping sounds.

"That's better, but not much. You'll have to improve if you want that B. Now where are your lips?"

She firmly tapped my cock on her pursed lips a few times.

"Much better Jennifer. Where is your tongue?" I asked, eagerly awaiting the answer.

She stuck her tongue way out, her face red with embarrassment, and tapped the head of my cock on the middle of her tongue.

"hmmmm...", I said disapprovingly, "I didn't feel the whole tongue. Try again."



Once again with her tongue forced out. She opened her mouth as wide as she could and put a few inches of me in it. Even with her mouth gaping, the thickness of my cock nearly filled the void. With a couple subtle shakes of her hand she rattled my cock inside her mouth, vibrating it between the roof of her mouth and the base of her tongue. On her final shake she gagged slightly as the weighty head of my dick touched the opening of her throat.



"Excellent Jennifer! You passed the hands-on test! Now onto the oral part of the exam. But first, we need to make sure you aren't tempted to cheat." I said smiling, "Stand up and bend over the desk."

She clumsily stood up, her panties dropping around her ankles, and leaned over the desk, facing away from me. Her tiny skirt revealing all my the very top of her little ass.

"All the way down Jennifer"

Without further instruction she laid her chest on the desk, her torso now perpendicular to my own.

"Put your hands behind you back and grab your opposite elbows"

She obeyed, drawing her shoulders back in order to be able to reach her elbows with each hand.

"Now hold still" I said coldly.



I reached into the desk and pulled out a roll of duct tape. With one quick tug I pulled out a long length of the tape. The tearing sound of the adhesive separating from the roll made her jolt as though struck by a bolt of lightning. She had never done any bondage before, and this was not going to be an easy introduction. She broke character for a moment and protested:



"Jackson, no, I don't want to"

But I didn't leave character, "I said to hold still Jennifer!"

"Please Jackson, I'm scared" she pleaded.

In the instant of that comment, I reached back and slapped her ass almost as hard as I could. She screamed out in pain as my hand print quickly turned from white to red, nearly covering her whole ass cheek. Her upper body jumped off the desk in reaction.

"Jennifer, this is your last warning, hold still or you will fail and be punished severely!" I said sternly.

"Yes..." she said with tears in her eyes, "Mr. Jackson."



Whimpering from the pain of the slap, as well as the fear of total loss of control, she then silently complied. Slowly she lowered herself back onto the desk, still gripping her elbows. I wasted no time binding her arms together, encasing her forearms from wrist to wrist in layers of duct tape. During the process I repeatedly grinded my dick up and down her ass cheeks and between her legs, again covering my member in her wetness. I grabbed her by her bound forearms and lowered her back into her kneeling position in front of me.



"Now its time to complete the oral part of this examination."

She looked terrified. Not only was she totally at my mercy, but now my cock was covered in her own pungent pussy juice, which she was undoubtedly going to have to taste. The very thought made her gag.

"Using only your mouth, you are going to make my dick point to the body part I tell you. Understand?" I said.

"Yes Mr. Jackson" she said in a low voice.

"Good. Its a short test, just one question and a bonus. Let's begin. Where is your esophagus?"



Her face lost all color. She knew I wasn't going to settle for my cock touching her neck. She knew she was going to have a mouthful of her own cum. She knew she had never taken a dick in her mouth her than about 2 inches. She knew she was going to hate this. She hesitantly opened her mouth and took the end of my penis in it. She grimaced as she tasted the bitter moisture of her own cunt on her tongue. Her shoulders lunged back and forth from gagging. She got my dick no further than usual before quickly turning her head to the side and letting me fall out of her mouth.



"As I said before Jennifer, you only get one warning, and you don't want me to have to show you where it is. Now, where is your esophagus?"



Again she tried, but to no avail. She reached the back of her tongue before her gag reflex and disgust at her own juices caused her to convulse and spit out my cock again. She looked down defeated and swallowed the saliva welling up in her mouth, too embarrassed to spit it out on the floor.



"I'm disappointed Jennifer. I guess we'll have to do this the hard way." I said casually.



I lifted her back onto the desk, just as before with her chest on it. This time I pushed her onto it further so that her hips were up on it, her legs pointing straight out off of the desk. Once again I pulled out the duct tape, pulling off her useless panties, and this time I began wrapping her ankles together.



As I looped the tape over her tights she writhed and protested saying "no, no, no" over and over.

"Do you want another spanking?!" I said menacingly.

"No Mr. Jackson" she said sheepishly, her ass cheek still glowing red from the last one. She laid still and let me continue my work.



Now, with her arms and legs bound I finished by fully hog tying her. I looped the tape around her bound ankles and also around her arms, bringing the two together. She looked as though she was unwilling grabbing her heels, with her belly down on the desk. I walked around the desk and stood in front of her, my imposing cock sitting at the edge of her lips.



"Now Jennifer, let's find that esophagus"

And with that, I starting burrowing my huge cock into her forbidding mouth, forcing it to open to its extremes, her bright pink lipstick highlighting the opening. Every inch that went in caused her to gag and squirm on the desk. Her only ability to protest was the muffled yelps and gagging sound she made as I mercilessly invaded her mouth. As I reached the back of her tongue, I gave a short quick thrust, feeling the tight warm embrace of the top of her throat. Tears were now streaming out of her eyes, her face was turning red. I pulled my cock out of her mouth quickly. It was followed by a painful gasp and lots of drool falling to the floor.



Mortified by her appearance and forced behavior, she pleaded, "No more, no more!"

"Don't you want the bonus question Jennifer?" I said devilishly.

"I... I.. can't... I... Yes Mr. Jackson." I love insecure girls. They will do anything if properly trained.

"Good Jennifer, " I said, bringing my cock to the opening of her gasping mouth, "now lets find your STOMACH!"



I grabbed her by her pigtails and violently forced my cock into her mouth. She was already gagging and whimpering. I pushed forcefully, once again reaching the top of her throat. Saliva was now pouring from the small cracks between my thick cock and the edges of her bright pink lips. She was fighting against her restraints frantically, but they would not budge.



Tickling the back of her throat with my cock, it was not even halfway in. I heartlessly jolted my hips forward, pulling hard on the ends of her pigtails as though they were reins. 2/3 of my engorged cock drilled visciously into her throat as she tried to scream, her cheeks now blown up like balloons. To finish reaching for the deepest recesses of her throat I put one hand on the back of her head and the other holding her under the throat. I then pushed the rest of my suffocating cock into her throat, her nose now resting firmly against my stomach. She let out a deep, strained gag over and over as I held my dick inside her. Her face was beet red and slowly turning blue from lack of oxygen. I was so deep that I could actually feel my dick with the hand I had gripping her throat.



Pleased with myself, I yanked my dick from her mouth. A fountain of tears and thick, ropey saliva followed and hung from her gaping mouth. Her shame knew no bounds now as she was gasping, weeping, and spitting large wads of throat juice onto the floor.



A normal girl at this point would be screaming for me to stop, screaming for help, screaming for anything that could help this end. But not one of my girls. No, the only thing going through her mind now was that she should have gotten my dick into her throat herself the first time. She had been brainwashed into thinking that she deserved her punishment and that she would do better next time. Her level of self-esteem was measured in my satisfaction, which almost always came at the cost of pain and shame. Every time I had my way with her, she became more ingrained with this belief.



"You earned your B Jennifer. Maybe next time you'll finish your assignment by yourself, huh?" I said.

She brought her gaze slowly up from the floor to my eyes and stammered, "Yes... Mr... Jackson."

"That's right." I replied, repeatedly slapping my sloppy wet cock on her cheeks and forehead, "Now for your final test. You do want an A don't you?"

She flinched from the cock slapping and said, "Yes Mr. Jackson".

"Good, this one is Public Speaking. Its short, but it the toughest one yet."



I went around to the other side of the desk, leaving her there, bound, to wonder what was coming. I went into my desk drawer and retrieved a pair of scissors. I cut the tape binding her ankles to her arms, still leaving her arms and ankles bound. I dragged her hips back so that she was once again bent over the table, her skirt now up around her waist. Even being only 90 degrees bent and having her legs firmly tied together, her miniscule asshole was perfectly presented. Her ass was so tiny and lean that her firm cheeks did nothing to protect her virgin hole, they could only frame it.



"All you have to do is say your ABC's. If you can do that without stopping, you'll get your A. Sounds easy right?"

"Yes Mr. Jackson", but she knew it wouldn't be that easy.

"Then let's begin"

"OK... A, B, C, D, E..eeeeeeeEEEEEEEEEE!!!!!!" she shrieked as I jammed my left thumb into her bare ass without warning.

"Start over Jennifer" I ordered, rocking my thumb deep in her ass as it desperately tried to flex closed.

"A, BbbbeeeeEEEEEEEEE!!!!!!" again she screamed, accompanied by the sound of her cheek being slapped roughly directly over her prior red welt.

"Again" I said coldly.



She began reciting very quickly. As she did, I took my big, thick cock and aimed it at her disproportionately tiny asshole.



"...Q, R, S, T AAAAAAAAAAAAAAAAAAAAHHHHH!!!" she screamed like a victim in a horror movie. In unison, I had retracted my thumb and plunged nearly the full length of my thick, 9 1/2 inches into her formerly innocent butt. She continued screaming and flopped around on the desk like a fish out of water, but there was no escape. She was mine. And she knew it.



"Again" I said as I slowly pushed the remaining inch and half of my cock into her rectum causing her to straighten her spine. I began gently swaying my hips in and out, moving my cock only about an inch. How I got my cock that was as big as her lower arm into her impossibly small, untouched hole was a mystery, but one I was enjoying immensely.



Her screams gradually dissipated into labored grunts and yelps. I could almost hear her gritting her teeth to cope with the pain from the extreme stretching of her inexperienced asshole. Over and over again she began reciting the alphabet, only to have me periodically interrupt with a violent slap, a tear at her pigtails, or a powerful thrust into her throbbing asshole. For nearly ten minutes she unsuccessfully tried, her ass cheeks totally red and speckled with black and blue, her face still tear and spit stained, her butt split open like she never imagined. But with this pain and torment came acclimation. Her ass was still in a great deal of discomfort, but she could now bear my incessant pumping.



Her vice-like ass was finally bringing me to climax, so I decided to take it relatively easy on her and let her finish.

"...X, Y, Z!" she said in a mix of exhaustion and triumph.

"Congratulations Jennifer! You earned your A in my class!" I said happily, still ramming her hard enough to rattle the large wooden desk.

"Thank you... Mr... Jackson" she struggled to say without sobbing.

"You know Jennifer, I might be able to make you valedictorian. What do you think of that? I said.

She took a long pause. She thought she was done. She was already taken past her physical limits. But, as one of my girls always does, she complied, answering "I'd like that Mr. Jackson"



I pulled my cock from her gaping asshole, watching it slam shut in the blink of an eye. I then lifted her 90 pound frame from the desk and positioned her kneeling in front of me. Her ankles and arms still taped, she pushed her knees apart to maintain balance. She knew what was coming and was mortified. She had never had sperm on her face before, ever. To her, as she told me in the past, it was the most demeaning thing a man could do to a woman sexually. She instantly clenched her whole face, shutting her mouth and eyes like a safe. This was going to be great.



I began feverishly stroking my cock in front of her face, every now and again slapping my dick, covered with the insides of her mouth, pussy, and ass, against her face. Then I started in with the final humiliation:



"You love having cum on your face don't you?" I asked.

"Yes Mr. Jackson" she said, opening and shutting her mouth quickly.

"You want my huge, hot, sticky load all over you, don't you?"

"Yes Mr. Jackson"

"Then say it"

"I want your load"

With a sharp flick of my cock in her face, I said again "Say it dirtier!"

"I want your hot, sticky load on my face!" she replied quickly.

I love forcing women to beg for perversions they are disgusted by. "Keep begging for it til I cum! And it better be dirty!" I ordered. The obscenities she spewed after this (with a little guidance from me) to avoid any further "punishment" would have her Church group calling for an exorcism:



"I want to swallow your thick sperm!"

"I'm your little jizz whore!"

"I love when you fuck my ass and cum on my face!"

"Blow your load all over my pretty face!"

"Let me taste your salty semen!"



I was about to explode, so I grabbed the back of her head and pointed my cock directly at her face with my right. With her eyes still shut, she was about to make another filthy request for my load. As her mouth opened, I shot a thick stream of cum directly to the back of her throat, stopping her sentence. Simultaneously I ordered, "Swallow it!" before she could spit it out. She did as she was told, following with a small gag and a grimace across her face, her mouth now slammed shut.



The load that followed could only be described as freakish, as are most of mine. I fired hot, thick jets of cum over every inch of her face. She would jolt as though slapped by every one of them, each one blasting away at her nearly non-existent dignity. I came on her eyes, forehead, hair, cheeks, lips, nose, and even ears as she attempted to turn away, acting as though I was shooting acid at her. The massive load ran from the pools on her face down onto her tits and even her exposed thighs as I continued to paint her. With her face totally encased in the sticky white jizz, I shot my last few streams onto her tits as I aggressively pulled her bra down.



I stood back from my "student" and picked up her thong. I wiped the excess cum off of my dick with it and threw it back to the ground. I took a final satisfying look over my "innocent" little girl: Her schoolgirl uniform tattered and in disarray, her pigtails frazzled, bound with duct tape, her no-longer-virgin asshole throbbing, her rectum shredded, covered head to toe in a quart of my sticky cum, and she still kneels before me anxiously awaiting more instructions.



"Well Jennifer, I think you are #1 in the class now!" I said cheerfully.

"Thank you Mr. Jackson" she mumbled, being careful not to get any more cum in her mouth.



I stood her up and grabbed my scissors. I carefully cut the tape around her arms and ankles so as to separate them, but the tape remained on her skin. Her eyes still closed, she immediately went to wipe the cum from her face, to which I shouted, "Stop! Leave it alone til you are out of my office. Now go enjoy the weekend."



She slowly dropped her hands down and then put them in front of her. She couldn't see as her eyes were sealed by thick layers of cum, so she guided herself across the room, reaching out with her hands. It was a sight to behold: Her tiny, perfect body hobbling across the room, blindly, in heels, the pain of her bruised ass cheeks and deflowered anus making every step seem like a mile. This was definitely one of my more memorable "session," one she certainly wouldn't forget.



As she made it to the door, I heard a car door slam outside.

"Jennifer, I think that's my secretary Rebecca. Show her into my office when she comes in."

"Yes Mr. Jackson." she agreed disappointed. After the ordeal she endured, she was not even good enough to keep me satisfied for the day she thought.

"I'll try harder next time" she said, looking for encouragement.



But I ignored her final statement as she exited. I was too busy reveling in the thought of how terrified "Rebecca" would be when she saw "Jennifer." It would be another fun "session." But that's another story.