The School Tramp

Coach lifted me off of his dick and his cum immediately started running out of my ass. As he set me down my legs wobbled. Coach told the principal I had a fine tight ass and asked if he wanted a piece of that. Principal Henderson was already putting his pants back on. He said he would get into my ass another time but he did not feel like taking sloppy seconds at the moment.

They both talked to me for a few minutes, ensuring that I was not going to tell anyone about what had just happened. I assured them that I was not going to, so long as we could come to an agreement. They agreed that there would be no suspensions or punishments for Johnny or I. But they both wanted to see me again. I nodded in agreement and the principal left.

I had one more deal for Coach Grogan though. I put my panties back on, and sat on his couch. I lit a cigarette and relished in the feel of his cum oozing out of my ass and puddling in my panties underneath me.

I asked the coach if the rumours were true that he was giving some of the male students steroids to improve their performance. I told him that I did not need an answer about that, but I was wondering if his sources also had access to female hormones. If so, I wanted him to get me some. He smiled and said he would see what he could do. I should check with him at the beginning of the week.

He said that in return, he wanted to give me a weekly injection. He grabbed his cock and waggled it at me. I knew what kind of injection he meant, and I was more than willing to trade a bit of ass for the hormones.

Coach left and I changed back to my Carl clothes and headed home.

Mom was out when I got home. I tossed my Sindy bag under the bed and stripped to take a shower. The hot water felt wonderful on my body and I stood there for a good long time. When I got out and dried myself off, I realized that a bunch of my body fuzz was growing back including around my cock, and I decided that I would need to go for another waxing soon. I felt behind me, and then used mom's hand mirror that was always in the bathroom. I bent and twisted and finally managed to get a look at my asshole to confirm what my probing fingers had told me. My ass was still tightly closed. I had been afraid that the pounding from Coach might have left me gaping open, but my ass was young and resilient. I had a lot more fucking to do before it would begin to gape open and start looking like a pussy!

Back in my room I toyed with my cock a bit while I browsed some bondage and fetish sites, looking at all the interesting leather and other erotic wear. I had cum once that evening, without anyone touching my dick. I did love the feeling of my cock being played with, but I so much more loved my ass to be filled. With that thought, I grabbed my thick dildo and slid it easily up my butt. I climbed into bed and slowly wanked myself off as I worked the rubber cock in and out of my ass. I came into a tissue, then reached over and turned out the light. I fell asleep with the wonderful feeling of the dildo still firmly lodged in my back side.

Chapter 14 - Money

Saturday night turned out to be a significant night in my young life - or should I say in Sindy's life. Sindy was starting to consume me. Carl was starting to fade away.

Mom was heading off for an overnight with Mr. Henderson again. Cassie was going out for a girl's night with several of her classmates. That usually meant that she would be bringing some new guy back to her bedroom for the first time. So Johnny was at loose ends and he asked me if I wanted to get together again in a room at the Ambassador. I was still mad at him from Tuesday, but I was hungry for cock and had no other ideas for Saturday night and so I said sure.

The out of town football game was a lot further away so mom and principal Henderson were flying. He picked her up early Saturday afternoon. He came upstairs to chat with her as she finished packing her bag. He looked into my room and found me at my computer looking at various website. He stepped into my room and in a loud voice he complimented me on Thursday night. I looked up startled, and he added that my game at the Chess Club was the best he had seen in quite some time. He was complimenting me on my cock sucking at the same time as covering for me. He leaned down and whispered in my ear that I should not make any plans for Tuesday after school as I was going to have detention in his office!

I waited an hour after Mom left just to be sure that she was not returning for anything she had forgotten, and then I started transforming into Sindy. Cassie and I had to share the bathroom and mom's makeup mirror, but we managed well. I started with a long bubble bath and Id shave my arms, legs and as much as my groin area as I could reach. Much as I wanted another waxing, I could not afford it right now. When I was mostly done, I called to Cassie and she came in and shaved the bits of my groin that I could not reach.

Of course, she had to hold and move my penis around to get underneath and around it. She also shaved around my asshole. I did not have much in the way of hair, but it was nice to be smooth again.

Cassie teased me and got my penis erect, even taking the head into her mouth a couple of times. I implored her to suck me off, but she said no - though promising that if I was a naughty girl, perhaps later on that night she might relieve me.

She was curious about who my date was that night. I told her is was another one of the guys from the frat party we had gone to. We had been in touch by email and he was eager to see Sindy again. Cassie told me again that she was sorry things had not worked out between Danny and me, and she knew how much I wanted a boyfriend of my own, just like she had Johnny. I told her not to worry, I was having fun dating a bunch of different guys.

Cassie and I both left the house around nine pm. She was picked up by a car containing four of her classmates, including Karen Henderson, the principal's daughter. It seems she was eager to get out and play, while her dad was away!

I called a taxi. The driver looked at me with hungry eyes in the rear view mirror as we drove. I did look pretty foxy, I had to admit. The driver did not mind if I smoked in his cab, so I lit up a cigarette and practised blowing smoke rings, This got the driver's attention and he asked me if I was going to meet a date. We chatted for a few minutes and the conversation got suggestive. I eventually realized that he was trying to determine if I was a hooker. It was a fun ride over to Seneca as we chatted and teased.

When we got to the hotel the cab fare was forty dollars. That would pretty much drain all of the cash that I had in my purse. Johnny had promised to pay me back when he arrived, but I was still uncomfortable with the thought of having no money. My mind played back over my conversation with the cab driver and I smiled.

The cab driver was about fifty years old, had a pock marked face, a shaggy mustache and a fairly large beer belly, but he also had a dick.

We had parked off to the side of the Ambassador and it was dark. A few moments later I had dragged a piece of cardboard over by the cab. The cabbie was leaning back against his cab with his pants down. I had his cock in my mouth and was sucking him off in return for not paying him his fare. He offered me twenty dollars more if I would smoke while sucking him off. I shrugged, lit up a cigarette and alternated sucking on the ciggie and going down on his dick. This is the first time I encountered any kind of fetish.

It did not take long before he sprayed his cum into my mouth. I leaned back, showed him the cum in my mouth. I then took a deep drag on the cigarette, swallowed his cum, opened my mouth to show him it was gone, and then exhaled the smoke. I swear that his cock dry jerked several times!

Along with the twenty dollar bill, Carlos gave me his business card and told me that I could ride free anytime I wished, so long as I would blow him each time. I thanked him, told him he had a lovely cock (not really!) and told him I looked forward to a budding friendship.

That was the first time I took money for sex. I did not feel bad about it at all!

Chapter 15 - More Than I Had Bargained For

While I was in the cab, Johnny had texted the hotel room number to me. I bypassed the front desk and went straight to the elevators. When I got to the room, Johnny was waiting for me. He swept me into his arms and kissed me eagerly, and I kissed him back, but he was a bit cold to me too.

From the next room over I could hear the shouts of a bunch of guys as they watched a hockey game that was much too loud. The hotel room walls were very thin.

Johnny sat me down on the bed and asked me if I remembered what he had said the other night, about some of the other guys wanting to meet me. I said yes, and it was okay if he had them email me and I could set up a date.

Well, that wasn't exactly what he had had in mind he said, and he got up and opened the door to the connecting room. He took my hand and pulled me inside that room. There I found five of his classmates from the senior class. They had a bunch of pizza boxes and beer and, despite the windows being open, you could smell that they had been smoking pot too.

Upon seeing me, the guys have out hoots and hollers and started yelling, me first!

I pushed Johnny back into the first room and asked him what the fuck was going on? He said that the guys had said they could not wait to meet me. Cassie had told him about my blowjob contest at the frat house a couple weeks back, and so Johnny was sure that I would not mind giving his team mates the same treatment. I looked at him in disbelief! I told him that there had been plenty of witnesses there and it had been a controlled environment. It was unlikely that anyone there was going to lift up my skirt and find out my secret. Johnny told me that he had already told the guys that I had a dick and they were already cool with it!

I was still hesitant, but I HAD been looking forward to getting screwed by Johnny and drinking his cum. I had found it interesting to have sex with the coach and principal at the same time on Thursday night and here I now had the opportunity to not only suck off six guys, but to hopefully get fucked by several in the same evening.

We returned to the other room. One of the guys handed me a beer as Johnny nodded at them and they all cheered again.

Over the next fifteen minutes I mingled with the guys and ate pizza. They all treated me as if I was a girl. If anyone recognized me as Carl Barton, no one said a word. As I moved from guy to guy, each one was eager to touch me and kiss me. I kissed a few gently, but was careful not to get too frisky, yet.

But eventually they turned down the sound on the game and turned on some music. Someone handed me some pot and I inhaled a few times. That and the beer had me giddy and I was soon doing a strip tease. When I had my top and skirt off, all the guys oo'd an ah'd as they watched me roll my panties down past my stockings (yes I wore them over top) and my hard little prickie sprung to full attention.

I fell to my knees in front of Douglas and pulled his zipper down. I pushed his jeans down and fished his cock out of his underwear. I looked up into his eyes as I took the head of his dick in my mouth and then I swallowed his entire length. He looked amazed as I mashed my lips against his pubes. I then began to bob my head up and down.

But I did not manage to suck him long. Another hand pulled my head to the side and Jake stuffed his dick into my mouth. Soon I had all five guys standing in a circle and I moved from cock to cock to cock, sucking on each in turn as I would fist two other cocks at the same time. Johnny sat off to the side, drinking a beer and watching his teammates.

This went on for about ten minutes. I eagerly gobbled one dick and then another. When two cocks were close together, I tried to jam both of them in my mouth at the same time, but the guys seemed shy about have their dicks touching each other.

Then Gabe picked me up and tossed me on the bed. I was barely up on all fours before Gabe started working his cock inside my ass. Lucas moved in front of me and jammed his cock into my mouth and I was forced forward onto his cock as Gabe began to pound my ass.

For the next two hours I fucked and sucked the guys repeatedly in a variety of combinations. Some guys came in my ass, some in my mouth. Some spewed their jism on my face. When I was fucked on my back, I was able to suck another guy and fist one or two others.

The guys were frantic at first, but after the first hour they slowed down a bit. I was draining their energy as well as their balls.

Johnny had just sat there watching most of the time. But late in the activities, I was riding on top of Ted's dick. He was pretty tired, but I still needed more cock. I was on top of him, bouncing up and down trying to jam his cock ever deeper into my hungry ass, when I felt a hand push me forward. Johnny was behind me and I realized that he was trying to jam his cock into my ass, which was already quite full of Ted.

But Johnny persisted and soon he has managed to work is cock into my boipussy. I now had two cocks stuffed into my ass. Ted was motionless beneath me but Johnny began fucking me furiously. I moaned as he rubbed my prostate and for the first time that night I gushed my jism on Ted's chest. Johnny yelled that my ass was so fucking tight, and then both he and Ted blew their loads into my bowels!

All of the guys looked pretty drained, but Douglas was up for more. As the other guys all sat exhausted, their dicks all shrunken, Douglas took me by the hand into the other room and he fucked me on the other bed. He was on top of me, and as he lanced his cock in and out of my ass, he kissed me, despite my face being caked with dried cum and my lipstick being a mess. I nuzzled his neck and urged him on, rolling my hips and trying to increase the pleasure he was getting from me.

This was going to be a long fuck. He had cum several times already, so we talked casually about some school stuff. He told me that he had been amazed when Johnny had told him that the nerd Carl Barton liked to dress up like a girl and was a damn hot fuck! And then he mentioned that he had paid Johnny a hundred bucks to party with me tonight. I asked him to repeat that, and he told me that all of the guys had paid Johnny for the evening.

So not only was Johnny not in love with me, but he was a blabbermouth, AND he was pimping me out!

I was done for the night. More than done. I flipped Douglas over, moved down his body and took his cock in my mouth and hands. It only took a minute before Douglas's cum spewed weakly from his balls.

I told Johnny and the boys that I was done for the night. No one objected strongly. I took off my stockings and jumped into the shower in one room. When I emerged, I inspected my clothes and other than having a run in one stocking, everything looked fine. I spent a few minutes redoing my makeup.

The other guys were all gone when I opened the door to the adjoining suite. Only Johnny remained. I won't go into the details, but I screamed at him and reamed him out good. I got him to turn over the five hundred dollars he had collected for selling my ass to his friends. I also took another forty dollars from his wallet to cover my cab fare to the hotel, and another forty dollars to cover my cab fare home. He argued that he needed some of the money to pay for the room, but I told him that he was a shit and that I did not care.

I had already called Carlos and knew that I had wasted enough time. I ran from the room, took the elevator down. It was midnight when I got in Carlos cab and we drove away.

I put on a bright happy face as Carlos and I chatted amiably on the drive home. At one point I asked Carlos to pull over into a laneway, and I got in the front seat and blew him.

When he dropped me off in front of the house, I realized I'd had quite an evening. I had six hundred dollars in my clutch purse, I had blown five guys at least a dozen times and had my ass fucked eight or a dozen times. It has been hard to keep count.

One thing I was sure of though, I was never going to date Johnny again!

Chapter 16 - The Evening is Not Done Yet

As I climbed the stairs to the second floor, I could hear my sister grunting and groaning. She had obviously dragged some guy home to have some fun. Yes, Johnny was her boyfriend, but she was not exclusive to him and it was hard to imagine her going the weekend without a cock inside of her. I guess I took after her to some extent!

Her door was open a crack. I was about to walk past and just head to my room when she cried out, oh fuck me that feels so good! Jam it deeper! But I realized that was NOT my sister's voice. I had just assumed that the female voice was hers. I backed up and opened her door a bit wider.

Cassie was on the bed, but it was not her being fucked. Instead my sister was naked and had mom's strapon harness around her waist. She was laying on top of another girl and was ramming the double headed dildo into the other girl's pussy, while hungrily kissing her on the mouth!

My sister was fucking another girl!

The other girl was very vocal, telling my sister to ram the big cock deep into her pussy. Cassie had worked up a good sweat. While she pistoned the cock into the other girl, her one hand was twisting at the gal's sizable boob.

I opened the door a bit more to get a better view and I guess I made too much noise, because the other girl suddenly got startled and looked right at me. She pushed Cassie off of her, the dildo pulling out of her cunt with an audible squish. She asked Cassie, who is that?

Cassie smiled and beckoned me into the room, introducing me as her cousin Sindy. I was surprised to see that the other girl was Karen Henderson, the principal's daughter. I sat on the bed and compared the two. Cassie as thin, but athletic, with small breasts. On the other hand Karen would be politely described as plump. She was pudgy, short and had very large breasts. Her boobs were big, soft and almost pillowy - not like the large breasts that I had seen on Becky Winters at the frat party. Becky's were obviously implants, whereas Karen's were very very natural.

We sat and talked for a bit. After a couple minutes, Cassie reached into her drawer and pulled out a baggie that contained a few rolled joints and she lit one up. I was surprised that she would do that in front of the principal's daughter. The girls laughed at me and it was nice watching Karen's boobs jiggle. Cassie told me that she bought her stuff from Karen. Apparently she was supplying about a dozen of the girls and guys in school.

As we smoked the joint and talked some more, Karen and Cassie began lightly touching and caressing. Cassie kissed me deeply and soon I was kissing Karen too. Karen told me that she was a lesbian and had been hitting on Cassie for a couple of months, never expecting Cassie to respond. Cassie gave me a long lingering kiss as she said that, after fucking me a few days back, she had liked the feeling and wondered what it might be like to fuck another girl. So she had gone out tonight with the idea that she might bring Karen home with her tonight, and it had worked out that way.

Karen raised an eyebrow at hearing that Cassie had fucked her cousin. She asked me if I was a lesbian, and I said no, I had only started having sex about six weeks earlier and I loved fucking with guys - my experience with Cassie has been out of frustration, but I had enjoyed it.

Karen still did not realize that I was really a boy underneath my sexy outfit. She dragged me to her and enveloped me in her softness. Her tongue probed my mouth and I hungrily kissed her. My hands went to her breasts and my mouth soon followed. I took one then the other of her fat nipples into my mouth and she moaned lustily.