The School Tramp


(From “Boy” to ” Boy oh Boy!!”)

Chapter 1 – The School Tramp

I was a virgin. I did not want to be a virgin. I asked my sister for help, and that was a mistake. Well, at the time I thought it was a mistake, but it turned out to be the best mistake that I ever made.

I was nineteen years old at the time and entering my junior year of high school. Yes, my junior year. I had been very sick when I was six and had missed two years of school. So, when I started my junior year, my sister who was only eighteen was starting her senior year at the same high school. Heck, Bigelow was such a small town that there was only one high school.

As a result of being sick, I was also much smaller than would be expected. I was only five foot four, and while I was quite strong for my size, I looked very thin and, yes, you guessed it, even a bit effeminate – or cute, as my sister constantly reminded me. She kept telling me I would make a much better younger sister, rather than older brother. She’d always had that idea in her head and that is where the mistake comes in, but I will get to that in a minute.

Back to being a virgin, and not wanting to be a virgin….

Becky Winters was the school tramp. She was a senior and was supposedly Dwight Moore’s girlfriend. Dwight was the star receiver on the football team. But everyone knew that Becky would put out for anyone who took her on a date. It was said that she’d had sex with almost all the guys in the Senior class and over half of the guys in the Junior class. She was also supposed to have blown or fucked over half of the male teachers at the school, including the principal and vice-principal.

I said she’d had sex with over half of the guys in the Junior Class., right? Well, I was not one of them. I was too shy around girls, partly due to my height, and just because, well, I was a geek, a nerd, a nobody. My school marks were terrific – but that was because I had no personal life. I did not go out for any sports, I did not go to school dances or any social events. I was too shy. My only friends were the other guys who were called geeks and nerds by the supposedly hip, cool kids who hung out front of the school smoking all day.

I spent a couple days after school in the Chess Club and Math Club with a half dozen other shy and awkward guys. I spent my weekends in my bedroom studying so I could go to University in a couple years, or playing video games online with the geeks from elsewhere who never went outside. Also, I had discovered online porn recently and had easily figured out how to not leave any trace for mom to find when she periodically checked the sites I was visiting. Looking at the pictures, and the videos, made me finally realize that there was something missing in my life.

I could not talk to a girl unless she talked to me first. I’d had exactly one date in my whole life and that was with my cousin, Lucille, when her family visited ours last Christmas. And that was a humiliating experience that I will not explain further.

I was determined to end my virginity and the best way to do that, I figured, was to go out on a date with Becky Winters. I was convinced that if I did, I would finally get my cock inside a pussy! I was too shy to ask Becky out though and so I asked my sister to help me out, by speaking to Becky for me.

I haven’t told you about my sister Cassandra yet, have I? As I said, Cassie had just turned eighteen in the summer. She stood five foot eight, had long black hair and a gorgeous face. Cassie had been dating Johnny Long, the quarterback of the football team for the past two years. (And yes, predictably, Cassie is the head cheerleader.) As of a month ago, she had been wearing Johnny’s school ring and the two of them had been fucking like animals in her bedroom a couple nights a week ever since.

Mom took Cassie to the doctor and made sure she was on the pill. Mom was very open minded and realized that her horny daughter would be banging away with one or more boys as soon as she was of age and so she made sure her daughter was well protected.

Mom had even bought me a box of condoms and had THAT awkward conversation with me when I turned eighteen last year. Dad had run out on us when I was only ten and so Mom struggled with raising her two kids. (Mom said he had run off with a woman from the next town, but I had been taunted recently by the Barlow twins who told me that their dad had said my dad was a fruit and had run away with another man!)

I’m pretty sure she was disappointed in me for NOT bringing any girls back to my room, but she never said so, in so many words.

Oh, my name is Carl by the way; Carl Barton.

So anyway, I asked Cassie to get me a date with Becky, the school tramp. I even told her that I wanted the date so that I could lose my virginity. Cassie giggled and turned things around on me.

She turned it into a bet. It doesn’t matter what the wager was, just the stakes – If I won, then she would set me up on a Betturkey date with Becky, and would guarantee that I would have sex with her; and if I lost… well, if I lost then she should set me up with the date of HER choice and I would have to do whatever she said on the date, but she would also guarantee that I would have sex.

So, either way I would lose my virginity!

A no lose bet, right? More like a no win bet, as it turned out!

Well I lost the bet of course, and so, no date with Becky Winters.

But it did explain why, the next Saturday night, I was dressed in a bra, panties, dark stockings, short short skirt, blouse and two inch heels, with a bracelet on my wrist and wearing clip-on earrings. I was wearing lipstick and eye shadow and my long blonde hair was conditioned and pulled back in a ponytail. I was carrying a small clutch purse which contained keys, lipstick, makeup compact and identification.

I was nervously waiting for my sister to come down and join me, to wait for our dates with Johnny and his out of town friend, Kenny.

Chapter 2 – The Date

When my sister told me I would be going on a date with a boy, it did not surprise me. She could be an evil bitch when she wanted to be (which was often!), and she had always told me I would look cute as a girl. She chose a weekend when Mom was out of town and then got her boyfriend Johnny to find me a date. The day of the date she spent a couple hours getting me ready. I won’t bore you with the details except to tell you that after she was finished with me, I was definitely cute – more than cute! I was a knockout. The nerdy boy was gone and the hot girl was revealed.

I had to stop looking at myself in the mirror because I kept getting a hard-on in my panties. Not only did it not look becoming for a girl in a tight skirt to have a penis outline, but it kept leaving wet spots that took several minutes to dry!

The boys picked us up on time. Cassie introduced me as Sindy, her cousin. I thought she meant Cindy, but she emphasized that I spelled it with an S, as in Sin, since I was a naughty girl all the time! I blushed as Kenny’s smile broadened.

We drove to our nearby big city, Springfield, twenty miles away. During the drive Cassie snuggled up to Johnny who drove and Kenny and I sat far apart in the back seat making idle conversation. Kenny was definitely cute himself, in a boy way of course and seemed a bit shy.

We stopped for burgers on the way and then went to a dance club. The music was seriously thumping inside! At the door we all got asked for ID. I nervously showed the bouncer my Carl ID. He looked me over, smiled, and waved us all inside.

The lights were flashing, the bass beat was so low that the floors vibrated, the dry ice was creating clouds of smoky steam on the dance floor. We grabbed a table and the boys went to buy us drinks. Cassie told me not be nervous and just enjoy the night out. I had never been to a place like this as a boy, and I was excited to be here. I sputtered at my first sip of my drink, never having had alcohol before. Kenny laughed. He was even more cute when he laughed.

He and I sat talking as Johnny and Cassie went to dance. After ten minutes I realized that Kenny was too shy to ask me to dance, so I grabbed his hand and dragged him to the dance floor. I had never danced in my life, but the small amount of alcohol emboldened me. I was going to enjoy myself, dammit!

We were on the dance floor for twenty minutes, that first time – and I ran back to the table several times for more of my drink. Kenny was actually fun to dance with and every once in awhile his hands would touch my wrist, or waist – never for long, but each time it sent a thrill through me.

When we all began to get tired, we returned to the table, but just for a moment. Cassie dragged me off to the powder room. Well, we didn’t actually go to the washroom. Instead we went outside to the smoking area so that Cassie could have a nasty cigarette. While she smoked, she asked if I was having a good time, and did I like Kenny? I told her yes to both questions. She asked me if I liked Kenny enough to let him kiss me at the end of the date. I’d already been thinking of this, and told her yes.

When we went back inside, we discovered that our seats were taken up by a couple of Johnny’s teammates and the boys were avidly talking with each other. Cassie bought us drinks and we took them up to the dance floor, put them on a sideboard, and danced with each other for the next half hour.

Well, not quite with each other, since other boys kept coming up and asking if they could dance with us. I found it quite fun dancing with different boys – tall ones, short ones. Heck a couple of them were at least in their thirties! These older guys all wanted to dance much closer and had their hands around my waist a lot of the time. I found it strangely stimulating to have guys touching me so much.

Two or three of the boys were friends of Cassie, from her Betturkey Giriş senior class. Several of the boys asked if they could call me. I was too polite to say no, but I didn’t give out my phone number – I didn’t want them phoning Carl! I did let a couple of them give me their email addresses. And I even gave Cassie’s email address to a really good looking guy named Jeremy. When I wanted to get out on a date again, he might be… wait, I was thinking of doing this again?!?

When I complained to Cassie that the heels were starting to hurt my feet, we went outside for a smoke break again. Cassie giggled at all the attention I was receiving and told me that even after a couple of hours, I was holding up well. My mind was buzzing from the three drinks I had had, and I had to admit that it had been fun flirting with the guys.

One of the girls who also out in the smoking area was Becky Winters, the school tramp who I had hoped to have a date with. I realized that I actually looked better than she did!. However she was smoking a cigarette and looking extremely slutty. I was jealous of that look. I was also jealous of her for having a man sitting beside her, his arm around her waist and his lips locked to hers every time she was not puffing on her cigarette.

I asked Cassie for a cigarette. She looked at me in amusement but handed me one. She lit it for me. I tried to hold the cigarette like Becky did, and inhaled for my first time. I then had a two minute hacking and coughing fit as Cassie laughed loudly. But I did finish my first cigarette and was determined to eventually be able to match that sexy look that Becky had!

Back inside, we danced with the boys some more. Kenny was now much bolder and held my hand a good deal of the time. I squeezed his hand several times and this made him smile a lot. At one point he held me very close and whispered that he was having a great time. I realized with a start that he had a boner and it was pressing against my thigh. I pulled back from him, because I realized that I too was hard in my panties and did not want to be pressing my own cock against him!

After awhile we changed partners and I was dancing with Johnny. Johnny was much more handsome than Kenny and a much smoother dancer. While Kenny looked at me with innocent eyes, Johnny stared at me with lust. As we danced, his hands caressed my arms and his hands touched my hips repeatedly. I was definitely getting hot and bothered dancing with Johnny. Deciding to be a bit of a tease, I actually let my hand slide along his pants and I gave his hard cock a subtle squeeze! Johnny gave a startled groan and grinned at me. I don’t know if Cassie noticed my “handling” of her boyfriend, or if she was just tired, but she decreed that it was time for us to head home.

Cassie was staggering quite a bit. While I had had three drinks, she’d had at least twice that much, as well as some shots that various guys had bought her on the dance floor.

Chapter 3 – First Kiss, and more

As we drove home, Cassie was sitting as close to Johnny as the two front seats would allow. She was constantly kissing his neck and running her fingers through his hair. From the back it was hard to see what she was doing with her other hand, but it appeared to be in his lap.

In the back seat, Kenny and I were sitting side by side with every part of my right side, up tight against his left side. We were holding hands and talking in small whispers.

After a prodding glance back from Cassie, I turned my head and kissed the shy Kenny on the lips. He kissed me back eagerly. I had never kissed anyone like this before and did not care that my first kiss was with a boy. Soon our hands were caressing each other’s bodies as we mashed lips hungrily. I soon found Kenny’s tongue in my mouth and our tongues jostled and played with each other as we took turns sucking on each other’s tongues!

A few minutes later Johnny pulled off the highway and parked the car along a dark country road. Evidently he and Cassie were very familiar with this spot. My sister and her boyfriend were soon exchanging their own deep kisses. Meanwhile, I found myself laying on the back seat with Kenny lying on top of me. As we continued to kiss, he worked his hand under my blouse and unsnapped my bra. Shortly after, my blouse was undone and Kenny was licking at one of my nipples.

Of course, being a boy, I was flat chested, but Kenny did not seem to mind. As he flicked his tongue across first one and then the other nipple, they stood up firmly pert. I groaned and Kenny moved up and covered my mouth with his own as his fingers continued to tease my nipples. I could not see what Cassie was up to in the front seat, but by her position I assumed that her head was buried in Johnny’s lap, meaning she was probably sucking on his cock.

Well, in for a penny, in for a pound! I could feel Kenny’s hard cock pressing against my thigh, and I had quite the stiff rod of my own. I didn’t need Kenny shifting position and Betturkey Güncel Giriş suddenly feeling my dick pressing against him, so I flipped us around such that I was on top. Kenny put up no protest as I undid his belt, and then his zipper, pulled down his pants and then his underwear.

Kenny’s cock sprang erect. It was about five inches long and already very messy with all the precum he had been leaking. Kenny muttered something like, oh yeah babe, suck it! Cassie’s head briefly rose up and she looked back at me, grinning broadly and nodding at me to go ahead. She watched as my lips slid down on a cock for the very first time, giggled, and then went back to her own cocksucking.

I was a boy, dressed as a girl. Should I have been doing this?

Um, let me put that another way.

I was a nerdy boy, dressed as a hot girl! From the moment I saw Sindy in the mirror, I knew I was going to enjoy being a girl for the night, much more than I had ever enjoyed being a boy. I had decided I would do whatever it took to have the best time possible. I liked Kenny, and I was eager to be the best girl I could be for him.

I eagerly kissed, and slurped and sucked on his cock. I bobbed my head up and down and swirled my tongue along that nice warm stick of meat. I had never had a blowjob, but had watched several on my computer. II knew what felt right. Kenny guided me with his grunts and his groans, and his hands were holding my head at times.

As I bobbed my head up and down, I looked forward again and realized that Johnny had adjusted the rear view mirror so that he could watch the rear seat action. I gazed directly into his eyes as I took Kenny’s cock from my mouth and kissed the head. I then blew a kiss at Johnny who grinned and winked at me. Cassie still seemed to have her head in Johnny’s lap, but appeared to not be moving.

Moments later, Kenny started breathing hard. His leg muscles went rigid and he panted that he was cumming! I held just the head of his cock in my mouth as he spurted three strong jets of cum into my mouth. Without thought, I swallowed his cum and then I licked the rest of his juices off of his dick head. As we straightened up our clothing, I noticed that Kenny was no longer interested in kissing me. I guess he did not like my cum breath!

Johnny was arranging Cassie in her seat. Apparently the alcohol had gotten to her and she had passed out with his cock in her mouth.

It was a short drive back to Bigelow. We dropped Kenny off at the house of the friends he was staying with. I got out of the car and we hugged (no goodnight kiss!). He asked if we could call me when he came to town again. I said that it would depend on if I was visiting Cassie at the same time. He gave me his email address, and I gave him Cassie’s. He kissed me on the cheek.

Back in the car, Johnny and I were both silent and Cassie was passed out. When we got to my house, I helped Johnny get Cassie out of the car, and he took her upstairs. Since they had been lovers for a couple months now, I had no problem with him stripping her and putting her to bed.

I waited up to say goodnight to Johnny. I assumed he was not going to stay over, since Cassie was in no shape to have headboard thumping sex with him. As I waited I scrounged in Cassie’s purse for a cigarette, and I grabbed a coke from the fridge.

Chapter 4 – Johnny

When Johnny came back downstairs he was feeling chatty, so I handed him another coke and we sat on the couch, side by side. I explained that I would be sleeping on the couch while visiting my cousins. My aunt was out of town, Cassie was sound asleep in her room and, I assumed, Carl was asleep in his. Johnny made as if to get up and leave, but I told him to sit down, I enjoyed his company.

We chatted about the evening and the club. I told Johnny I had a great time and that I had never been to a club like that “back home.” He told me that I looked really hot, even better than Cassie had described when she asked him to set me up on a date. I told him that I thought he was pretty hunky and it was too bad that Cassie had dibs on him. I leaned in to him slightly and he met me halfway, our lips meeting in a delicious tender kiss.

For the next five minutes we kissed and sucked each other’s tongues. My hands roamed over his strong back and then reached for his belt. I giggled and said that I noticed that Cassie had not finished sucking him off, coyly asking him if he would like me to finish the job for him? In reply, Johnny rolled down his jeans and underwear and spread his legs. For the first time in my life, but by no means the last, I knelt in front of a man and worshipped his cock.

Johnny had a nice firm seven inch dick and I eagerly engulfed it in my mouth. This was my second cock of the night and it seemed so much more alive – firmer, spongier, tastier. While I sucked up and down its length, my fingers toyed with Johnny’s balls. Johnny moaned appreciatively and I could tell he was getting close to shooting his load. But then he pulled my head off of his cock.

Johnny pulled me up on his lap and I sat straddling him. His mouth hungrily found mine and we kissed passionately. I felt his rampant cock rubbing along my ass crack. Then he said, I want to fuck you, Carl!