The School Tramp

He knew! He knew I was Carl, not Sindy. And he still wanted to fuck me! I stood, took his hand and led him up to my bedroom. He explained that he had known who I was all evening - Cassie had explained the bet and during the evening had expressed disbelief to Johnny at how easily I had passed as a girl.

I pushed Johnny onto my bed and took my clutch person into the upstairs bathroom. I spent five minutes touching up my lipstick and makeup. I nervously looked through the medicine cabinet and found an old jar of Vaseline which I took with me to my bedroom. Johnny was naked on my bed and he helped me to strip off my blouse, skirt and panties. When my erect cock bobbed into view, framed by my stockings, it did not phase him at all. We kissed some more as he lay me down on the bed.

Johnny pushed my legs back and used his fingers to massage some of the Vaseline around and into my asshole. As his fingers pushed inside of me, I felt an electric tingle. He lathered more lube onto his firm cock and then he lay down upon me. We kissed a great deal more until I was feeling comfortable and I told him I was ready.

I spread my legs wide as my man placed the head of his cock at the entrance to my ass and then he slowly pushed. At first my anal ring resisted, but suddenly the head was inside me. Johnny paused for a moment to give me a chance to get used to the feeling. Then he pushed some more and slid another couple of inches inside of me. I grunted at the pain, but nodded encouragement at him. He slid back out a bit and then in again, further. Slowly over the next couple of minutes, he worked his cock back and forth, in and out and I got used to the feeling of being so very full. At one point, his cock slid over something inside of me, and I saw stars! A minute later he did it again. I soon figured out how, and where, and each time Johnny fucked into me, I wriggled my bottom so that he rubbed against that same spot.

Johnny moaned, telling me that I was so fucking tight! He loved jamming his pecker into my sweet ass pussy, as he called it! I wrapped my legs around his back and pulled his head down for another delectable kiss. My man started fucking me harder and faster. I was moaning and shouting. My nails dug into his back at one point and he howled with pain.

I was moaning and cursing him as he pounded away at my ass, his cock rubbing hard along my pressure point. My own cock was rigid between us. Finally Johnny buried himself deep inside of me and I could feel his cum gushing into my ass. My man was seeding me!

Johnny collapsed on top of me and then moved his weight onto the bed beside me. His cock slipped out of my ass and lay on my thigh. We cuddled and kissed tenderly for several minutes.

After a few minutes Johnny got dressed and I walked him down to the front door. I was just wearing my stockings and heels, the rest of my girl clothes having been strewn around my room. My cock was limp. I kissed Johnny tenderly on the lips as he left.

I walked back up to my room, my ass hurting, but in a nice way, as I did so. I looked in on Cassie. She was fast asleep. Johnny's howls and my groans had not disturbed her drunken slumber.

I lay on my bed, recalling the evening. I had had a great time at the club, sucked off two boys and been fucked in the ass. What more could a girl ask for on her first date?

In all of the excitement of the evening, I had not cum myself. I returned to the bathroom and fixed up my makeup one more time. I then went to mom's room and sat at the end of her bed, looking at myself in the full length mirror. I lit another one of Cassie's cigarettes (I was going to have to get some of my own!). I still wanted to practise that wanton slut look that I had seen on Becky Winters. I posed a couple of different ways and practised blowing out the smoke provocatively. I giggled as I realized that I was trying to emulate the school slut!

As I stared in the mirror I saw a sexy blonde schoolgirl, dressed only in dark stocking and heels, with a cute cock sticking out from her groin. I grabbed hold of that cock and beat myself off. As I reached my climax, my cum geysered high into the air several times.

I slept well that night, dreaming of Johnny, and Kenny, and Jeremy, and oh so many other boys!

Chapter 5 - Lust

The next morning Cassie was groggy and could not remember how she got home and into bed. It was a relief to know that she did not have any memory of me banging her boyfriend. I told her I had had a great time. It was pretty obvious to her that Sindy was not just a one-date wonder. She hugged me and said she would enjoy having a part time sister!

I helped her to wash the clothes I had worn and in turn she sat down with me and gave me some tips on applying makeup. When she finished she dressed me in some of her smaller clothes, suitable for daytime wear and then she drove us in her car to the local cheap mall and I spent a couple hundred dollars of my savings on a bunch of girl clothes for me - some to be worn daytime, and some hotter outfits for evenings.

When we got home, Cassie had several emails from men trying to contact me. She gave me the email addresses. In my room I set up a separate hotmail account for Sindy and replied to two or three of the guys. One was Kenny, one was Jeremy who had caught my eye.

I was still walking uncomfortably at school on Monday, but by Wednesday my ass was fine. All I had were the memories of my glorious first ass fuck!

I saw a lot of Johnny during the week. He and Cassie were always together at school, always walking hand in hand. I found many excuses to talk to Cassie and each time Johnny smiled at me. Once we briefly touched fingers and my heart skipped a beat.

My email conversation with Kenny faded into nothing in a couple of days. He had gotten what he wanted from me. I was already learning about men!

But, I talked to Jeremy a few times by instant messenger online and agreed to meet him for a date on Saturday night. Cassie agreed to help sneak me out of the house, since Mom was going to be home. I spent a nervous hour putting on my makeup and then my panties, stocking, bra, dress and heels. I had bought a larger bra and filled a couple of balloons with bird seed to give me a larger bosom. I made sure to not fill the balloons very full, since I was still a developing girl!

Cassie helped me put my hair in a ponytail again and then distracted mom as I left the house and hid in the back seat of her car. Cassie came out and a couple blocks away I hopped into the front seat with her. We shared a cigarette as she drove me to my date.

Jeremy lived in Seneca, the next town over, and he met me at a small restaurant. Cassie drove off for her own date with Johnny.

We sat in a booth as we ate our meal and talked animatedly. I knew I looked pretty sexy and Jeremy had a hard time keeping his eyes off of me. We each had a drink, and then another - being a boy, Jeremy was drinking beer, but I had a margarita, then a cosmopolitan. Drinking girl drinks was fun! As the alcohol began to affect me, I scooted closer to Jeremy and was soon holding his hand under the table.

We then went to a movie at the town's multiplex. As we sat there in the dark, I was starting to feel horny and leaned over and kissed Jeremy on the lips. He squeezed my hand tighter and tentatively kissed me back. Fortunately the theatre was fairly empty and so no one was sitting behind us, to complain of us blocking their view. We ignored the rest of the movie and kissed and kissed. At one point, I rested my hand on Jeremy's pant leg, right on top of his rigid cock, and squeezed. For the next several minutes I massaged his dick and he squirmed and moaned in my mouth.

When the movie was done, we hopped into Jeremy's car and he drove to a dark laneway, where we resumed our kissing. I unzipped Jeremy's pants and grabbed hold of his cock. Thinking back, I realized that this had been my goal for the evening. I was eager to try sucking on another cock! I rolled my fingers around the glans a few times, but when I went to suck on it, I realized that my position was too awkward - Jeremy drove a manual transmission and the damn stick shift was in the way.

We hurriedly got into the back seat. Jeremy was such a sight, almost tripping over his pants! I then put his cock in my mouth and bobbed my head up and down hungrily. It took only five minutes until Jeremy pushed my head down hard on his dick and he splashed his cum down my throat. As we finished, I licked the rest of his cum off of his penis and teased the head with my tongue.

Back in the front seat, we held hands as Jeremy drove me to the local hotel, where I got out in order to get a cab home at the cab stand there. Much as I liked Jeremy, I was not ready to let him know where I lived. He was a gentleman and got out and opened the car door for me. As we parted I turned my head so he could kiss me on the cheek, but he instead gave me a full deep kiss on the lips, with tongue. This was a boy who did not mind kissing a gal with cum on her breath!

As I left the cab I looked at my watch. I was late enough that Mom was already in bed, but I still tip toed delicately upstairs to be sure I did not wake her. I stopped off in the bathroom to tidy up my makeup and then sat in my room, wondering why I was concerned about how I looked.

Fifteen minutes later, the door downstairs thumped open, and I could hear Johnny and Cassie coming home. Ten minutes after that there was a faint tapping at my door. I opened it a crack and peered out. It was Johnny. I let him in.

He smiled at me and then kissed me hungrily. I put my arms around him and we swapped tongues for the next five minutes. Johnny explained that he had made sure Cassie had a lot to drink, and she had passed out as soon as they got to her room. Blue balls again?, I asked Johnny. He nodded and a minute later I was on my knees with his beautiful cock between my lips. Five minutes later I was once again on my back on my bed, and my sweet man had his cock buried to the hilt in my ass. The first time we did this, we had sex. This time, we made love.

My eyes smouldered as I made small mewling sounds as his cock drove in and out of me. Johnny whispered about how beautiful I looked, and how fucking sexy I was. We made love face to face, alternating tender kisses and deep tongue probing kisses.

My cock was incredibly hard and bounced against each of our chests as Johnny thrust in and out of me. Johnny then surprised me by taking my cock in his hand and slowly running his hand up and down it, pausing to tease the head.

I had to stifle my groans of lust to be sure Mom did not hear me! But it was only moments until I huskily whispered, I'm going to cum! Johnny's balls were also churning, and just as my cock spurted its fuck cream, I felt Johnny let loose his own torrent of jism deep in my bowels! We both mewed our love for each other as we spurted our cummies!

It took fifteen minutes of cuddling for our heart rates to return to normal. Johnny's cock felt so delicious in my ass, even deflated, and I was disappointed when it finally slipped out of me.

Johnny quietly left of my room, and got back into bed with Cassie.

I removed the rest of my stockings, etc and went to the bathroom to clean off my makeup.

I was back in bed soon and trying to drift off to sleep. But I heard noises from the next room, which I realized was the head board banging against the wall. Cassie had evidently woken up and Johnny was now banging my sister.

I did not mind sharing Johnny with my sister. Or course, if she found out, she might not like sharing him with me!

Chapter 6 - Skulking around

On Monday at school Johnny managed to pass me a note asking me to put together a bag of clothes and makeup and meet him after classes the next day.

Now that football season was over, the cheerleaders were practising cheers for the basketball team. Johnny did not play basketball. So he had two hours when he was free from Cassie and he wanted to see Sindy!

When the final bell for the day rang, I got my Sindy bag from my locker and hopped in Johnny's car. We drove over to Seneca - just far enough away that it was unlikely any of our classmates would see us - and he got the key to a service station washroom. I spent 20 minutes changing clothes and putting on my makeup and lipstick.

We then drove to a local burger joint and had some food while holding hands. Well, we held hands for the first few minutes. After that I was eating my burger and fries with one hand, while my other hand was under the table, squeezing Johnny's cock through his jeans. It was fun watching him squirm and drip mustard from his burger onto his shirt. He got me back by smearing a bit of ketchup on my face when he kissed me between bites.

I had a raging hardon of my own in my panties which I tried to calm down when I went to the washroom to remove the ketchup and fix my lipstick.

The sun was setting early those days. On the drive back, Johnny found a laneway and we parked hidden from the main road. We kissed frantically for a few minutes and then Johnny suggested we get out of the car. He bent me over the trunk of the car and pulled down my panties. Back at the service station I had lubed up my ass. Johnny stood behind me and slowly pushed his cock into my ass. The previous times we had fucked I had been on my back on a bed. This was my first time being stuck from behind, and standing.

I missed kissing while fucking, but Johnny did get even deeper into me than he had before. Wow! And when I shimmied my ass, I was able to get him sliding along that pleasure point. I was seeing stars and he vigorously pounded into my ass pussy! Johnny grabbed hold of my hips and set to jack hammering into me. It only took five minutes and he was spurting into my bowels! My own cock was not stimulated by being squeezed against the hard metal of the car, but I was content, knowing that my man had used me so well!

We repeated this again on Thursday after school. That time a farmer drove by us on his tractor, and just waved as he watched the young stud hammer away at his blonde girlfriend!

Chapter 7 - Frat Boys

Earlier in the week I had told Cassie that I was eager to get out on the weekend again as Sindy but had not yet decided on who to go out with. As far as Cassie knew I had only been dressed as Sindy a couple of times and sucked off my dates each time. When I told her that I had let Jeremy fuck me in the ass (not true, it was Johnny, but I could not tell her that!), and I had liked it, her jaw dropped. She told me that she definitely had to watch me get ass fucked!

The next day she said that she had found a college guy to invite us to a frat house party on the Saturday night. Johnny was going to be off doing stuff with a bunch of his friends, so it would be a girls' night out for Cassie and Sindy, and she was sure that I would be able to get as much sex as I wanted!

Getting out of the house on Saturday night was easy. Mom had a date and was long gone by the time that Cassie and I were ready to go out. Cassie helped me pick out an outfit that was more risque (can you say slutty?) than any I had worn before. I was wearing a black waist cincher and a short black skirt over black stockings. My heels were four inches this time. Cassie did up my makeup to accentuate my dark eyes. My long hair was again pulled back in a ponytail.

I had found a piece of clothing called a gaff. A loop went around my penis head and I then pulled my cock back between my thighs, giving me a smooth front. No erections for me tonight, but also less chance of unsightly bulges.

The frat house was in Springfield and Cassie drove, but only after I got her to promise that she would not drink much - she had to be able to drive home!

We did each have one drink before we left. In the car, between cigarettes, Cassie pulled out a joint. I had never done any kind of drugs or such before (remember, as a boy, I was a geek!), but what the fuck, I was exploring my feminine side and so we shared a few hits and got a bit giggly as we drove to the party!

When we reached the frat house, there were several people entering and we had to wait because they were checking id and stamping hands of the people who were old enough to drink. (Once we were inside no one paid attention to the hand stamps, it was all part of some administration bullshit). The guy checking the identifications was a really cute, bulky blond guy. The only id that I had was my Carl driver's license. He looked at me in surprise as he looked more closely at my face. Then he told me his name was Danny and he looked forward to seeing me inside later. He also told me to be careful.

The frat house was huge. It had four floors and a basement. There had to be at least sixty people on the ground floor and I could see more going up and down the stairs. All the gals looked incredibly hot and they were all being pursued by guys. Cassie and I were barely inside the door when we were handed glasses of home made punch. I took a sip and the potent alcohol almost knocked my panties off!

For the next hour Cassie and I were chatted up by most of the guys in the place. The music was thumping and we danced with several guys. Most took the opportunity to paw me on the ass and grind their pelvises into my thigh. If I was not wearing the gaff, my own cock would have been rock solid from being around all these hunky men.

Cassie's objective for the evening was to watch me being fucked by a guy, and I was eager to get that happening. We could have both dragged just one guy up to a room, but Cassie was extremely horny herself. After about ninety minutes and several drinks, we found ourselves dancing with two hot studs who were both eagerly kissing us and fondling our butts. Cassie grinned and nodded at me. She took my hand and led me towards the stairs. We asked the boys if they wanted to join us in a private room upstairs, and they eagerly followed.

It took awhile to find an empty room. We found most doors locked. Those that were open already had a guy and girl fucking or sucking each other. But one of our studs actually lived here and we went up to his room on the third floor.

When we got in the room, the guys pushed us back on the beds and began kissing and groping us. After a couple minutes they got off of us and Cassie and I were laying there. My hand touched hers and she squeezed mine. The guys suggested that it would be pretty hot if we two girls made out with each other. Cassie grinned and pulled me to her, her mouth seeking mine. For the next five minutes we traded passionate kisses and our hands wandered each other's bodies. She pulled off her top and undid her bra and pulled my mouth to her tit. For the first time ever, I was sucking on a girl's nipple, and it was my sister's nipple! Cassie teased me by running her fingers along my trapped cock in my panties. I groaned against the teet in my mouth.

By this time the guys had their shoes, pants and underwear off. Cassie and I knelt in front of them, and eagerly took their rods into our mouths. Cassie was sucking on Dave's nice 7 inch member, but Bruce's cock in my mouth was a disappointing four inches.

Dave pulled Cassie up, pushed her on her back, whipped off her panties, and in moments had his dick deep in her pussy. He was grunting and groaning as he pumped away at her. Bruce pulled me to my feet, but I had to explain to him that I was on the rag that week, so he could not fuck my pussy - but he could have my ass if he wanted. His disappointed frown turned into an excited grin.

Cassie pushed her beau off of her, saying she needed to help me. I braced myself against one of the desks in the room. Cassie knelt, and flipped up my skirt and pulled my panties down enough to expose my lubed asshole, but still keeping my cock hidden. Bruce was eager to plunge in to me. Cassie took him in her mouth and bobbed her head on his cock a couple of times to add even more lubrication. She then guided his cock to my asshole and watched as the cock easily sank into my boipussy.