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Amy's Surprise

showstoppa_4114 on Transgender Stories

“Amy’s Surprise”

 

by Matthew Ford

 

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an style="font-family: verdana">Amy Carlson was a beautiful girl who lived about 3 blocks from my house in a town with less than 2,000 people. She was home schooled until she was 19, when she transferred to the high school for her senior year.

 

Amy had brown, shoulder-length hair and beautiful green eyes. Her dad was a dentist so her teeth were blindingly white. She had evenly tanned skin, was about 5’6” and probably weighed around 120 lbs. She had a nice pair of boobs. They weren’t huge, only 36B, but they were round, firm, and perfect. Her legs were long and muscular, her stomach was firm, and her ass was amazing. It was round and well sized. Somehow, it was firm and soft at the same time. The year Amy went to the high school I was a junior. I had a few classes with her, but not as many as I would have liked. She only attended classes to get the credits she required to get into the private college she wanted to attend. I was the starting tight end and line backer on the varsity football team that year. Amy wanted to be a cheerleader, but she said she was just too busy. I could understand that, she went to school in the morning and worked as a waitress in the afternoon.

       

After the start of the 2nd quarter of school Amy’s sister, Karissa, got into a car accident with Amy’s car. Since she only had liability insurance, and was saving all her money for college tuition she couldn’t get a new car. Her parents had two other children to put through college after her so she didn’t ask them. Since her house was on the way to school I started giving her rides everyday. I would stop outside, honk, and she would be ready to go. One morning on the way to school, I asked her to go to homecoming with me. She said that she would love to, but she couldn’t. No matter how much I asked she wouldn’t tell me why. I just assumed it was because she wasn’t over her ex-boyfriend, who had gone on to college that year.

       

The year went on until football and basketball were over. It seemed like the year had gone by really fast. Amy and I spent virtually all of our free time together. At the beginning of April I asked Amy if she would go to Prom with me. She said no, again refusing to give me a reason. Two weeks later after school Amy came over to my house since she had the afternoon off and I didn’t have tennis practice on Fridays. We were watching “Zoolander” in my room when the doorbell rang. I went to go answer it. It was the FedEx guy. My dad had gotten a package. I left it on the counter for him and went back to my room. When I walked in Amy was on my computer checking her MySpace account. Amy looked at me, smiled, and said, “Matt, you wanna hang out next Saturday? I can get the day off.”

 

“Next Saturday is Prom ‘Ames’. I guess we could hang though, I don’t have a date for it anyway,” I answered.

 

Amy said, “Well, if we’re gonna be hanging out anyway, and Prom is going on, why don’t we just drop in and check it out?”

 

I was stunned. “You mean…wait, do you mean you wanna go to Prom with me? Or do you just wanna check it out?”

 

“Matt, will you go to Prom with me?” she asked smiling.

 

And just like that, I had finally succeeded in getting a date with Amy, or she had succeeded with me, either way I was happy. I had to line up a tux fast. I called my friend Brandon and he hooked me up. I was excited the whole next week. Everyday I saw Amy, and everyday she seemed to flirt a little more. Then, finally, Saturday came. I spent almost the whole day getting ready. I went to town to get a corsage and I stopped by the jeweler’s. At 7:30 that night, I grabbed the corsage, jewelry box, (and stuck a condom in my wallet, just in case) then got in my car and drove to Amy’s house. I went to knock on the door but Amy opened it before I could. She was standing there in a strapless dark purple dress that went to mid-thigh and pushed up her breasts, revealing a lot of cleavage. “Let’s get out of here before my parents know you’re here. They must’ve taken a million pictures of Karissa and Brian.”

 

We went to a nice restaurant for dinner. We talked and ate in our corner booth for almost an hour before I got the bill. Amy had been touching my leg all evening, but after the waiter went to get my change she laid her hand directly over my dick. She started rubbing and I knew it wouldn’t be long before it was hard. We adjusted our seating so we were even closer. Amy rubbed my crotch until I knew I was about to cum. I started to groan, and then she stopped, saying, “Not yet. Not here.” Then she got up as the waiter brought the change back. And said she had to go to the restroom but she would meet me in the car.

 

It was a little after 9:00 when we got to the school. We presented our tickets and went inside. Every time we danced Amy would rub up against me. My dick was throbbing by the time we went to take pictures. I let her choose the pose we would use. She decided we would do the dance pose. She laid back into my arms like I was dipping her. My dick pushing and rubbing against her ass. I knew she could feel it, and I also knew she loved torturing me like that.

 

When the last dance started playing at 11:55, the Prom King and Queen took their spots in the middle of the dance floor. It was my friend Brandon and his date Stephanie. We had already congratulated them and we decided to duck out then. There were several parties we could have went to, but we decided to go back to her house. Her parents had decided to get an early start on their anniversary vacation by getting a hotel room for the night before heading to the airport the next morning, so we would have the house to ourselves until Karissa got home. We both knew that Brian would not miss a party, so we had a while.

 

As we sat on her couch making out, I broke the kiss to give her the necklace I had bought her. She said she loved it, and that she had a surprise for me as well. She stood up and unzipped her dress, lowering it enough to reveal that she had a strapless purple bra on. She smiled at me as she unsnapped it and showed me her amazing boobs. The dress was still around her waist as she came back to the couch and sat on my lap. Amy looked me right in the eye and said, “Remember the day I asked you to Prom?” I nodded “And Remember how I wouldn’t go out with you or tell you why before that?” I nodded again. “Well, I’m going to show you why I wouldn’t go out with you until tonight. Last week, when you went to answer the doorbell, I got on your computer to check my MySpace, but before I did that, I wanted to see how far you’d gotten on your Economics report. I was going to check the report I swear, but I saw a folder that I had never opened before. I was curious, so I opened it. There was another folder inside, so I went into it. Then, I saw something that shocked me. I had found your porn. I figured you had some, most guys do, but I was surprised at the kind. Now, before we go any farther, I have to ask…do you like that shemale porn?”

 

I was mortified. I didn’t know what to say. I thought she was going to freak if I said yes. But then again, if that’s what had gotten her to go out with me, maybe I should tell her the truth. “um, well, I’m gonna be honest with you Amy. The idea of a hot girl, who also has…uh, a dick, does turn me on…so, yeah, I uh, I like shemale porn.” I was really embarrassed, I was waiting for her to get up and ask me to leave.

 

Just as I expected, Amy stood up…but instead of asking me to leave, she smiled at me. I looked back at her, confused. “Matt, I love the necklace…it was a great surprise.” As she pulled down her dress she went on, “and I told you that I have a surprise for you. And I think you’re gonna like it.” With this, her dress dropped to her ankles and she stepped out of it. She was wearing a purple thong, but what intrigued me most, was the bulge in it. “I have your surprise right here. But before you open it, I need to know that you want it. And you have to promise me that this surprise will be our secret. And you have to agree to always take good care of the surprise. Now, will this be a secret?” I nodded. “Will you take care of the surprise?” I nodded again. “And finally, do you want it?”

 

“Amy,” I replied, “I want your surprise more than anything.”

 

She stepped forward and said, “Then open it up.” With that, I slowly reached my hands out, and pulled down the purple thong until an 8 inch cock sprang at me. “Suck it, suck my cock,” Amy said softly, yet sternly. I needed no more coaxing. I opened my mouth and wrapped my lips around Amy’s cock head. I popped it from my mouth, then stuck it back in. I sucked on the head for a few seconds, then I stuck my tongue out and licked the bottom of her cock. I took it out of my mouth and licked the length of Amy’s surprise several times before taking it back into my mouth. This time I went deeper, sucking about 4 inches into my mouth and bobbing my head on that for a while. Amy looked into my eyes the whole time. “Deeper,” she whispered. So I began taking another couple inches of her cock. it was pushing into my throat now, my body wanted to gag, but I wouldn’t let it, I was loving sucking Amy’s cock too much to stop. She threw her head back and exhaled loudly. I began massaging her balls. They were shaven clean, just like the rest of her body. I squeezed them softly, and she moaned quietly. “Lick my balls,” she commanded. I didn’t want to stop sucking her cock, but I did as she said. I slowly jacked her cock while I licked her balls. My face was buried in her crotch. “Suck them,” she whispered. I took one into my mouth and sucked on it, then pulled my mouth away and it popped out, then I wrapped my lips around the other, repeating this several times. I was jacking her cock with one hand, fingering her ass with the other, and sucking her balls one at a time…I was really into it. Girls had done this to me before, and I had always wondered what it would be like to be on the other end. Now I knew, and I liked it. Amy grabbed my hair and pulled so that I knew to stand up. I didn’t really want to quit, but my mouth was pretty tired. She stood in front of me, looking into my eyes. She pushed me back onto the couch and dropped to her knees.

 

Amy undid my pants and pulled my 7 inch dick out. She immediately stuck it in her mouth. As she went up and down on my cock her left hand squeezed my balls. I was so hot, I knew I wouldn’t last much longer. She stopped her expert blowjob long enough to say, “Lemme know when you’re gonna cum.” Then she lunged her head forward, forcing my cock down her throat. She was taking it all, I couldn’t believe it. Amy went all the way down and all the way back up so quickly I knew she had done it many times before. Every time she would pull her head back far enough my dick would make a ‘pop’ as it was released by her lips.

 

“Ames, I’m, I’m gonna cum…” I struggled to speak because of the amazing feeling. When I said this Amy’s mouth went into double time. She sucked harder, bobbed faster, and her tongue seemed to be everywhere on my dick at once. I moaned as I came. Shooting a good 9 shots into her mouth, surprisingly she never stopped to swallow, it just all collected in her mouth as she continued to suck. She kept working on my dick until the pleasure was too much for me to take and I grabbed her head and pushed it away. All of my cum was still in her mouth. She opened wide to show me, then closed her mouth and swallowed it in a series of 3 gulps. She smiled at me with her snow white teeth.

 

Amy stood up and said, “I love cum. That’s one benefit of having a dick, I can have nice warm cum whenever I want. I want you to finish me now, but don’t swallow. Just keep it in your mouth and we can share it.”

 

I dropped to my knees and took her cock in my mouth as quickly as I could. I wanted to take all of it like she did to me, but her cock was about an inch longer than mine, plus I had never given head before. I was able to get almost 7 inches of it. I tried to duplicate the things that she had done to my cock on hers, I could make it ‘pop’ out of my mouth, but I couldn’t suck as fast or as hard as she could. As I worked on her cock, I started squeezing her ass. I began thrusting her cock down my throat by pulling her closer to me with my hands on her ass, basically forcing her to face fuck me. After a few minutes I was able to take almost all of her sweet cock down my throat. She warned my that she was going to cum, so I started massaging her balls. I moved my mouth out so that I only had the cock head in my mouth, then I took my left hand and started pumping her shaft while playing with her balls with my right. She threw back her head and groaned as cum started spraying into my mouth. Shot after shot of Amy's jizz filled my mouth. I swallowed some of it, I remembered what she told me, and I really wanted to share it with her, but there was so much of it I had to. I swallowed 2 gulps of it and my mouth was still full to capacity. I didn’t know cumming that much was possible. When Amy finally pulled her dick out of my mouth cum was running down my chin because I couldn’t keep it all in. it didn’t taste particularly good, but it wasn’t bad either. The feeling of having Amy’s hot jizz filling my mouth was incredible. She dropped to her knees and tipped my head forward and started kissing me, her tongue stealing her cum from my mouth. Her cum dripped out of our mouths and got all over her chest.

 

After kissing and swapping the cum back and fourth for about a minute, Amy started swallowing whatever went into her mouth. I started to swallow as well, trying to get as much from her as I could. We both drank it greedily until it was all gone. Then I pushed her back, licked up what was on her breasts, and swallowed desperately.

 

We made out for another 20 minutes until Amy got up and went to get something to drink. When she came back to the living room she had 2 bottles of Gatorade and a paper bag. She threw me the bag and a bottle. I took a drink, and peeked in the bag. I saw condoms, dildos, lubricant, and a couple CD’s.

 

Amy took a drink of her Gatorade and smiled brightly, “I hope you’re not too tired, it’s only 2:15. I’m not done yet, are you?”

 

I thought for a second, and replied, “Ames, I could go all night.”

 

Just then a car pulled into the driveway. It was Brian’s car. Karissa got out of the driver’s side and walked up to the door with Brian following closely behind. They came inside together and walked right by us and upstairs without a second glance. I looked to Amy after they were upstairs and she said, “Don’t worry, we’ll see them again before we go to sleep,” then she took another drink of her Gatorade and flashes me a beautiful smile. As I looked at her I thought to myself, "My girl has a bigger cock than I do. How many guys can say that?"

Amy's Surprise 2: Enter Karissa

showstoppa_4114 on Transgender Stories

“Amy’s Surprise 2:

Enter Karissa”

 

by Matthew Ford

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“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 7th to 10th 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.

Amy's Surprise 2: Enter Karissa

showstoppa_4114 on Transgender Stories

(I just want to thank those of you who gave "Amy's Surprise" reviews. It was my first story and I was happy to see that you enjoyed it. I hope this installment will be as well received as the first one was. Please leave reviews good or bad as well as suggestions. All input is appreciated. Thanks again, and enjoy.)

 

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“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 7th to 10th 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.