The School Tramp

I asked Karen if she has always been into girls and she said yes - she had never even kissed a boy. She thought that they were too hard and angular. She had always been drawn to females. I asked her what she might think of a pretty boy, and she said that she did not know. She would have to think about that if she ever found one.

She pushed me lower and spread her legs wide. I found myself staring at her pussy for a moment, before she pulled my face to it and told me to eat her. I eagerly began lapping at her cunt. At the same time, Cassie moved behind me. She flipped up my skirt and pulled my panties down, and off of me. She lubed up my ass, and then sank her fake cock deep into me, causing me to moan into Karen's cunt.

Karen urged Cassie on, telling her to ram that cock into my pussy - nor realizing that it was actually in my boipussy!

We worked ourselves into a frenzy for the next five minutes and then Cassie pulled me upright and whipped off my skirt. With her cock still lodged in my ass, my own cock was standing at stiff attention. Karen gasped in surprise, only then realizing that Sindy was actually Carl. She giggled as she realized that Cassie was actually stuffing her cock up her BROTHER's ass!

Karen murmured that I WAS a pretty boy and then did not hesitate to take my cock in her mouth and begin to suck me. Cassie removed the dick from my ass and lay back to watch Karen fellate her brother. Cassie lit up another joint and we all shared it as we hugged and kissed and caressed each other.

We were all very mellow when Cassie mentioned that Karen was a virgin to boys - she had had plenty of dildos up her pussy, but never a cock - and that Sindy was a virgin to girl - I had had lots of boys up my butt, but had never put my cock in a girl. Perhaps we needed to each help each other out?

And so it was that after yet another joint and a lot of kissing, I slid my cock into its first pussy and brought a gal to delightful bliss for the first time in my life. It was an interesting experience, and Karen's pussy did wonderful things to my boy cock. When I shot my load deep inside of her, I groaned and fireworks lit up my brain

But I have to honestly say, I felt SO much better when it was someone else filling MY asspussy with their jism!

(Aside: As you are aware, this IS a story. So no one gets pregnant, and no one catches any disease!)

Karen was pleased with the experiment, but said that she would prefer to stick with pretty girls, although for a boy, I was darn cute!

We all petted and caressed for awhile longer. Karen was fascinated that Cassie and I were having sex with each other, but Cassie clarified that she would not let me fuck her. Karen asked if she just meant her pussy, wondering if Cassie might let me fuck her in the ass. Cassie admitted to having let Johnny take her ass cherry the past weekend and having enjoyed it. She looked at me, and said that she did not know.. perhaps.

It was time to call it a night and so I told the girls goodnight. It took me twenty minutes in the bathroom to get cleaned up. I put on a nighty when I went to bed and drifted off to sleep.

At about four in the morning, Karen came into my room and crawled in bed with me. We cuddled and kissed a bit and then we both fell asleep. It was nice sleeping with a large warm pillow!

Chapter 17 - Sunday with Karen

When I woke up around ten or so, Karen was gone. As I made my way to the bathroom to shower, I heard the two girls in Cassie's room, moaning and groaning. I took a quick peek in and found that this time Karen was fucking Cassie. Karen waved at me and blew me a kiss. Cassie beckoned me in to the room, but I declined. I told them I would have breakfast on the table for them in an hour.

I put on some light makeup and a pair of girl jeans and a simple top.

At breakfast Cassie said that she had plans with other people for the day and would be leaving shortly. Karen asked me if I would like to hang out with her for the day. I knew that I had a lot of Carl homework to do - my grades were really plummeting - but spending the entire day as Sindy with a new girl friend was much more appealing and I said sure!

Cassie left shortly after that. Karen and I went upstairs and for an hour she helped me practise my makeup some more. Her approach was different than Cassie's and I learned a few different tricks. In the end, my makeup was a bit more garish, and a bit more slutty. That was how Karen said she liked her girlfriends, slutty.

We smoked two joints while we did this and I had quite a buzz on. As we drove around in Karen's car we had yet another joint. I ended up telling Karen what had happened with Johnny the night before - how he had pimped me out to his classmates and how I had made him give me the money.

As we drove around for the next hour or so, Karen was having very short conversations with people on her cellphone and we were frequently stopping to chat with friends here and there. Many were classmates of mine or her. I said hi to all of them, and none realized that the sexy gal in the passenger seat was Carl from school. But I realized that they were not really paying attention to me. I finally realized that Karen was making the rounds, delivering pot to various customers!

When I mentioned that I had made five hundred bucks from Johnny the night before (I did not mention the cab fare I got from him, nor the twenty I had made from blowing Carlos) Karen told me that I should never be ashamed of making money. I had killer looks and there were men and women out there who would pay to be with me. She told me I was foolish to give my ass and mouth away for free.

Karen told me that she had over twenty thousand dollars in a bank account that her dad did not know about. Most of it was from selling weed, but she also had regular gigs with a few housewives in her neighbourhood who paid her for sex with them.

I'd only had a sex life for less than two months, and had been enjoying the attention too much to think about whether I could get any benefits from it! But what Karen said made sense!

The money I had made last night was burning a hole in my pocket book and I told Karen I wanted to go shopping. She giggled and said she had a better idea. Ten minutes later we parked the car and she took me into a tattoo and piercing parlour. Karen wanted to add a new tat onto her ankle and so I hung around for a half hour while the young heavily tattooed proprietor used his machine to etch the new design onto her leg.

While the work was being done, Karen kept urging me to get inked. I finally gave in and when she was done, I had the guy put two small paw prints just above my left hip. It wasn't much, but it was a start.

However, I had also been intrigued by something else that I had seen on several gals in the porn videos I had been watching online and Karen agreed that we had time.

So I asked the guy to pierce my belly button. For fucking jeezus christ, but that HURT! Normally he would have just put a rod into the piercing and told me to come back in a couple weeks to replace it with some jewellery, but I sweet talked him into putting in a long dangly shiny bauble right away. It was my first girl jewellery!

When I say sweet talked, I had actually taken Karen's discussion to heart - when he was done, the buy put a closed sign on the door and I went into the storage room with him and pulled down his pants and blew him. He was not handsome, nor particularly likeable - but when he was ready to cum, I let him jerk off onto my face and he gave me the tattoo and his labour for doing the piercing for free. I had to pay for the jewellery since the store owner would be checking the books.

I used the washroom to clean up my face and reapply my lipstick. When I came out I found the guy sucking on Karen's tits. She had gotten her tattoo for free as well!

After that we drove back to Karen's house. Her dad and my mom would not be back until about 6 am the next morning, so we had the place to ourselves. We smoked another joint and then spent a half hour just kissing and gently cuddling with each other. Despite being a confirmed lesbian, Karen went down on me and sucked my cock until it was almost ready to explode. She then lay back and let me put my dick inside of her and we fucked for about fifteen minutes before I squirted inside of her.

As we lay there panting, she told me that she had enjoyed being fucked more than she thought she would, but she still preferred eating pussy and fucking other girls with her strapon. She wanted to be the one in charge. I told her that I also enjoyed fucking her, but that I truly loved having a big strong guy ramming his cock up my ass.

We grinned at each other and a few minutes later it was my turn to be on my back, with my legs up on Karen's shoulders as she drove her large rubber cock in and out of my tight ass! We fucked missionary style and doggie style. She stood me up and bent me over the dining room table and slammed her cock into me. She was loud and vocal as she came many times from having the nubbin on the base of her cock rubbing against her clit. I spurted my own jism twice more, once on the dining room table, and once on her kitchen counter!

When she drove me home, I have her a hundred dollars and she gave me several joints. She was now my supplier too!

Chapter 18 - Double Injections

On Monday I was called to the school office and handed a note which would excuse me from my classes at two pm. I was to go see Coach Grogan at that time. I showed up at his office and the Coach told me to come in and close the door. He was sitting behind his desk and as I approached he pushed himself back a bit and I saw that he had his dick out and was playing with it so that it was already hard. He told me to get on my knees and suck him.

I hesitate and then explained that I could not do that as Carl. I would need to go to my locker and get a few things to become Sindy. He said we did not have a lot of time. I hurried to my locker and grabbed my change bag. Back at the Coach's office, after locking the door, I pulled off my pants and shorts and put on a pair of panties. Coach smirked that those would not be staying on for very long. I took out a tube of lipstick and rouged my lips. I then closed my eyes and let Sindy slowly creep into my mind. I was ready.

I knelt and twirled my tongue around the head of that wonderful large black cock. I ran my hands up and down its length and caressed Coach's balls as I began to fuck my mouth down on his cock. Deeper, Coach said, and I obliged him my pushing my head lower and lower and lower until my nose was nestled in his pubic hair.

As I blew him, Coach caressed my head, running his hands through my hair. He told me he had the hormones for me and that each Monday I should come to his office for two injections in my ass. One being his prick, and the other being a needle. He told me his supplier had come up with something new and these hormones were fast acting. Almost immediately my skin should start to soften. Within a month, my ass should start retaining fat and grow rounder, and my tits should start showing signs of growth. Coach said that normally a girl like me should expect to be able to grow tits one size smaller than her mother's. He said that would not help me much since my mother's tits were so small. He said that he knew someone who would give me implants if I ever wanted them, but they would cost about five grand. I had not really thought about having my own breasts before. The idea was... exciting.

Coach pulled me up and backed me up against an empty wall. He lifted one of my legs and held it high as he aimed his cock at my pucker. He slid into me easily and sank his shaft easily into my ass. His was the biggest cock I had taken so far, but he slid easily inside of me. Coach used his other hand to twist my nipples. He seemed delighted by my bauble dancing from my belly button.

His cock slid across my prostate and I was seeing stars as he roughly fucked me against the wall. It took only five minutes before he spasmed and my ass filled with his cum. When his cock slid out, the cum ran down my leg.

Coach told me to bend over his desk and he took a syringe out of his drawer, filled it from a vial and then jabbed me saying that he figured that was the smallest prick I'd yet had in my ass!

I took a few minutes in his private washroom to clean up the cum, remove my lipstick and try to get the rest of his cum out of my ass. When I returned to class I was wearing the panties, rather than my Carl underwear. For the rest of the afternoon I made occasional squishing noises, as residual cum leaked out of my ass and made my panties moist.

Chapter 19 - Expanding Horizons

On Tuesday I met up after school with Douglas, one of Johnny's five friends who had gangbanged me at the Ambassador. A couple of the guys had contacted me by email. Douglas was the quickest to ask if we could get together just one on one. I told him that he would have to either get us a room at the Ambassador in Seneca or he would have to buy me some dinner. He opted for the hotel room. I think he was afraid of being seen with me in public, not being comfortable yet with the boy part of me.

I told mom I was going to go study with one of my friends and would not be back until close to eleven. She scolded me for staying out late with school the next day, but also seemed relieved that she would not have to put up with me around the house for the evening.

I walked a block away and met Carlos whom I had called earlier. I had not told him that it was Sindy who was calling and so he figured he was just picking up a regular fare. I got in and told him where to drive me. As we drove I pulled out my makeup compact and put on some lipstick and a bit of eyeshadow. Carlos was watching me in the mirror, puzzled. But when I took out a cigarette and lit and then said hello to him in my Sindy voice, he looked back in surprise. You are boy? he asked me? Do I look like a boy, Carlos? No, no. I just surprised is all! He replied.

Carlos was now one of the growing number of people who knew that Sindy and Carl were the same person. He did not seem disturbed at all when I pulled down his pants and blew him in return for the cab ride. Once again he gave me an extra twenty bucks for smoking while I sucked him off.

Douglas let me in the room and was a bit puzzled by my half-boy half-girl appearance. I told him to go for a walk and come back in a half hour. I used that time to change into the Sindy outfit I had brought along and to finish my makeup which I had crudely started in the car.

When Douglas returned he found me laying on the bed wearing nothing more than some frilly panties and dark stockings and heels. He hastily climbed on the bed and kissed me tentatively. I kissed him back as I removed his clothing. I took his prick in my mouth and was gobbling on his juicy cock just five minutes after he had come back into the room. No nice preliminaries for this boy. He was eager!

I realized how eager a couple moments later when I felt his hand grasp my cock and start to stroke it. I asked him if he had done this before and he muttered no, but said he had always wondered what it would be like to touch another guy's cock. I told him I was NOT another guy, and he stammered that he had not meant that I was a guy... just that he had been curious. His touch felt nice and we played with each other's cocks for awhile. I moved to take him in my mouth again and he swung around so that his face was in my crotch, and he hesitantly licked MY pricklet!

Soon we were both sucking eagerly on each other's hot dicks. Douglas may have been an amateur, but his mouth was warm and felt as nice as Cassie's and Karen's, and even Danny's had.

I pushed my head all the way down on Douglas's dick. He tried to do the same to me, but he choked and sputtered!

I lay back and wrapped my legs around Dougie's back, pulling his groin to mine. We ground our cocks against each other for a few minutes. Then I said to him, fuck me. Just that simple. And that is what he did. With no resistance at all, his cock slid up into my back passage and he was comfortably inserted inside me. He leaned his head down and kissed my lips. I sucked his tongue hungrily and he began to thrust his cock in and out of me. I pulled his head further down and he sucked on one nipple, and then the other. I shivered in delight.

After ten minutes of bliss, Dougie was ready to squirt. He pumped a nice load into my ass and collapsed on me.

A few minutes of rest and I thought Dougie might be done. But instead he rolled over and asked me if I would fuck him in the ass. He knew I liked being fucked a lot, and just as he had been curious about touching another guy's dick and sucking on one... he had done those, and figured maybe he should go all the way and see if he liked having a cock in his ass!

I told him I did not want to. I wanted to be the girl, not the guy. But he pleaded with me and I remembered that Cassie had gotten off so much on fucking me in the ass, that she had gone out and fucked Karen a few nights later!

I went to my bag and retrieved my bottle of lube. I had not needed it lately - it seemed that spit was all I now needed to get cocks to fit into my butt. But Doug had never even tried putting a carrot up his ass, so he was bound to be tight.

I put a couple of pillows underneath Doug's ass. I might have gotten better position if I tried to do this doggie style with him, but he wanted to watch, which meant bending him over backwards. I used a couple of fingers to smear the lube around his asshole and to push lube inside. While I did that, Dougie used lube to moisten my dick and work it to full attention.

As to fucking other people, I was a virgin other than my escapades with Karen a couple days earlier. Now here I was pushing the head of my cockette against Doug's anus, and meeting stiff resistance. Doug grunted in protest, and I almost thought we were going to stop. But I pushed a bit harder and finally my glans pushed past his sphincter. Once that was accomplished, steady pressure allowed me to sink another two inches inside him.

He told me to wait, wait, wait.. and I did pause and let him get used to the feeling. Then I pulled back a bit and pushed some more. Over the next ten minutes I slowly pushed and pulled my cock inside his ass as he grew accustomed to it. I cannot say that that time gave me a lot of pleasure. It was like having my cockette squeezed by a tight velvet vise which kept trying to push me out. Finally my entire five inches were firmly in Doug's ass. Doug was no longer complaining of pain so I took this as a sign and began to pull back and thrust harder. At the same time I wiggled my cock around as best as I could, trying to be sure I found his prostate.

I knew I had found my target when Doug began to moan in pleasure and lick his lips. His eyes were shut most of the time, but I could tell that he was beginning to like the fucking. His own six inch cock was very rigid and I grabbed hold of it and began to stroke him.

His ass was definitely a lot tighter than Karen's cunt had been. I guess anal muscles are firmer than pussy muscles. After another five minutes, Doug's face scrunched up, his leg muscles tightened, and he sprayed his cum onto his chest. This all caused his sphincter to grip my pricklet tightly and I shouted as I fountained my own cream into his rear.

We both lay panting on the bed for several minutes and then Dougie hurriedly dressed and left. Later that night I introduced Danny and Doug to each other by email. Doug never asked me out again. (Two months later I got an email from Danny thanking me for sending Doug his way. Doug had just recently told all his friends that he was gay and introduced Danny to his family as his boyfriend!)