The School Tramp

Cassie stared fascinated as Bruce pulled back and then sank deep inside me again. Well, as deep as a four inch cock would go. I loved the feel of a cock in my ass, but this one was frustratingly small!

Dave had Cassie lean against the desk beside me and he thrust his cock back into her hot quim. As the two frat mates pounded our butts side by side, Cassie and I held hands and kissed passionately, swapping tongues eagerly. Cassie's hand squeezed mine hard as she came twice in quick succession. I was frustrated though. Bruce was enthusiastic, but lacked any technique and no matter how much I wiggled, I could not get his cock rubbing across my prostate with any consistency.

One thing that I DID like though was that Bruce grabbed my long pony tail and wrapped it around his hand. He kept yanking on it while he was thumping away at my ass! This helped him get his tiny dick into me a bit deeper. I actually liked the feeling of being dominated in this way!

Dave and Bruce both grunted and groaned and then shouted as they came. When they were done, they both left the room quickly, telling us to pull the door closed behind us. Cassie and I rearranged our clothing. As we made our way back downstairs, Cassie told me how hot I had looked. She giggled as she pointed to the cum running down my leg from my messy panties!

Chapter 8 - Contest

When we reached the ground floor, it seemed like most of the party had vanished. But we followed noises and found the stairs to the basement. As we descended, my heels rapped loudly on the steps. I still marvelled that is was ME wearing those heels. A crying girl rushed past us going up the stairs, away from the crowd in the basement.

The basement was mostly one large room and there were about 70 guys and gals forming a circle. One girl knelt in the centre of the circle. A guy was standing in the middle, asking for a volunteer, since the other contestant had chickened out. Several guys were standing around the inside of the circle, looking very eager, but most of the girls were looking at the floor, trying not to be noticed. When the guy mentioned that the winning gal stood to win at least $400, Cassie pushed me from behind and I found myself stumbling into the centre of the circle!

I glared at Cassie as everyone in the room cheered. The guy led me to kneel down two feet away from the other gal. I looked at her and realized that it was Becky Winters, the high school tramp. She smiled at me and wiggled her fingers in a brief wave. I smiled back. I was sure she did not realize I was Carl Barton.

The organizer explained that we were going to have a blow job contest. Every guy who wanted a blow job had to put in twenty-five dollars and that went to the gal who managed to make him cum, regardless of whether she won or lost. Each of the spectators who was watching had to put in five dollars. The contest would last for twenty minutes, and whichever gal got the most guys to cum, got to take home the spectator money.

The interested guys put in their money, and they put their names in a hat. To be fair, names would be drawn at random. Oh, and one last thing said the guy in charge. In order to be sure that the guys actually came, there was no swallowing. The guys had to pull out and ejaculate on the girl's face!

Well, I had wanted more sex, and I was in for it now!

Names were drawn from the hat and the first two guys stepped forward. They dropped their pants and pulled their underwear down to their knees. Becky and I each had a limp cock hanging in front of our faces . Someone had a stop watch and when they shouted GO, I immediately drew that first cock into my mouth. It took me two minutes of sucking and fisting of that dick before the guy stuttered that he was coming and he pulled out of my mouth and shot three streams of cum onto my cheek. When the second guy stepped forward I saw that Becky had a rope of cum across her nose and was working on her second cock.

My second and third cocks were fairly small and I managed to get each of them off in three or four minutes each. The second guy squirted on my chin, but I forgot myself with the third and let him cum in my mouth. I swallowed before I remembered and so he did not count towards my total!

As my number four stepped up, the crowd all giggled and clapped. I looked over at Becky to see her mouth up against her man's groin. As I watched she pulled back and a seven inch cock emerged from her mouth. She had deep throated the guy. I had never tried that, but I knew I was going to have to do that soon - but not in the middle of a contest. Becky's face had a good coating of cum on it already.

At one point I noticed several people with their cell phones out, taking pictures. Cassie was one of them. I made sure to pose for her briefly at one point, with a cock poking solidly into my cheek and sticky ropes of cum across my nose and eyebrows!

My fourth cock was a nice six inches, but he shot pretty quickly. One squirt went into my hair, but two powerful jets of cum hit my left eye. I used my finger to clear my eye, and then licked the cum off my finger.

Two or three cocks later, I glanced at Becky again. I saw her working hard on her current cock. The guy she was sucking looked to be pretty drunk and I think he has having trouble staying hard. Becky pulled down her tube top and her large tits popped out. They were gorgeous breasts, though very round and obviously fake. But that just added to Becky's overall trampiness. Becky dragged the guy's cock across her nipples and moaned. Her guy needed no more than that as he suddenly shot his jism across her tits. Becky reached for her next cock as my next one stepped forward.

The guy with the stop watch told everyone that there were three minutes left and that Becky and I were tied with seven successful blowjobs each.

My next cock stepped forward. He was big. He was black. He was hung. I looked up into the eyes of Dwight Moore, Becky's boyfriend. Yes, Becky's boyfriend had not only brought her to a frat party where she was blowing strange cocks, but he was also participating by being sucked off by her competitor.

I could see why a tramp like Becky kept Dwight as her steady boyfriend. His cock was huge. Erect it was at least ten inches and seemed as thick as a soda can. I could barely fit the knob of his cock in my mouth! I ran my hands and tongue along the solid truncheon. I wondered if I would be able to fit that thing in my ass if he ever tried to fuck me!

But for the moment, I had to get him off! I twirled my tongue around his glans, and I sucked on the head of his dick while my hands pumped up and down his shaft. The crowd cheered as Becky's guy came, his cum dripping onto her cheek and nose. The crowd counted down the seconds to the end of the twenty minutes, urging me on. I had a hard grasp on Dwight's balls and could feel the tension in his legs, telling me that he was going to shoot, but time was called before he did.

I had lost, but I was not giving up. I continued to suck and spit on Dwight's shaft. Now that time was up and his girlfriend had won, Dwight was eager to shoot. He grasped my head and began to shove his cock into my mouth. My hands were gripping his ass tight as he finally shot a thick load and I eagerly swallowed bolt after bolt after bolt of hot jism.

I smiled as I stood. The crowd applauded and Becky hugged me. I was handed $175, including Dwight's money and Becky was given her suck money, plus $350 from the crowd. The organizer then offered us each twenty five dollars more if we would lick the cum off of each other's face. Becky declined, but I said I would do it if they gave me the whole fifty bucks. The guy nodded and for the next few minutes I eagerly licked all of the thick jism off of Becky's face, and the cum that had been splashed across her large fake tits. I managed to tease her nipples with my fingers which made her moan. I kissed her on the lips and she eagerly kissed me back.

Becky Winters, the school tramp, had kissed me!

I collected my extra fifty bucks and everyone moved upstairs to resume the party. I found an empty washroom, washed my face and touched up my makeup.

Chapter 9 - Danny

The party was in full swing again. Cassie and I got separated on the dance floor and I spent the next half hour dancing and talking with various guys. All the guys were showing a LOT more interest in me and it was hard to keep their hands off of my ass as we danced. Several asked me to go to a private room with them, but I just wanted to dance for awhile. At one point I found Cassie again. Her hair was dishevelled. I wiped a bit of cum off of her chin and had her lick my finger. She giggled and said she had just blown this really cute second year college student.

A few minutes later, I felt a tap on my shoulder and turned to face a grinning Danny. Remember, he was the guy checking id at the door? The one I said was hunky and cute? Well, he still was, and I felt my heart beat a bit faster as he asked me to dance. It took only three minutes for him to suggest that we go up to his room. With him I WAS in the mood. I asked if my cousin could come up with us, as she wanted to watch.

Once the three of us were in Danny's room and he had locked the door, Cassie plopped herself down in his desk chair, and Danny kissed me deeply. I wasted little time in getting on my knees, getting his cock out and jamming it into my mouth.

Cassie pulled her panties down and was slowly frigging her clit with the fingers of one hand, and was every once in awhile clicking pictures on her cell phone with the other. Danny quickly removed all of his clothing and I realized that below the eyebrows he was completely hairless. He had even removed all of the hair from his cock and the rest of his groin. I found the sight of his bare hairless cock highly intoxicating and I knew I was going to have to do the same to myself!

Danny made to remove my skirt and Cassie started to protest. But I told her to relax as Danny knew my secret. As he deftly removed my gaff and my cock sprung free after an evening of neglected torment, Danny admitted that he was gay. Danny pushed me back onto the bed and we fell into an embrace, kissing hungrily. I reached for his cock and he reached for mine. Johnny had briefly fisted my cock once when we made love, but other than that, this was the first time that another person had touched my prick. Danny's hand was both gentle and firm as he stroked me. I moaned in lust, and Danny moved down my body and took my cock into his mouth.

Another first! And oh god, did it feel so damn sweet to have his tongue and mouth moving up and down on my dick. Now I knew first hand why the guys liked it so much when I sucked them off!

Danny spun around and presented his own cock to my mouth. I enveloped it hungrily and we were soon both eagerly devouring each other's cocks. I heard Cassie get up and soon she was taking closeup pictures of my mouth bobbing on Danny's dick. I tried to get Danny's shaft into my throat, like I had seen Becky do, but I gagged and could not. I definitely needed practise before I was going to get a dick down in my throat!

My own cock was close to shooting and I told Danny. This made him bob his head on my cock more vigorously and shortly thereafter my back arched and I shot my thick load into his mouth. As I lay there panting he reversed position again and kissed me long and lovingly. He pushed my own cum into my mouth and we swapped it back and forth before each swallowing some of it..

Danny reached into his bedside drawer and pulled out a tube of lube. He squirted quite a bit on my asshole and worked it in with his fingers. He thrust first one, then two, then three fingers inside of me, and I realized it felt quite nice to be fingered by someone who knew what he was doing.

He had me kneel on his bed and squatted behind me. Cassie moved forward and took the lube and ran her fingers up and down Danny's cock, making it slick. Wanting a very close view, she then scooted underneath me, her groin at my head, and her head underneath my dick and balls. She squealed in excitement as, just inches above her face, Danny pushed his cock against my anus. The head popped in easily and he slowly sank his entire, beautiful, thick, juicy seven inches all the way into my ass.

Oh fuck, did that feel good!

Cassie oo'd and ah'd as she watched my asshole pucker outwards as Danny pulled back, my ass trying to hold on to the invader. Her left hand began to frig her clit again as her right hand squeezed my balls. I squirmed and she giggled.

For several minutes I was lost in pure bliss as Danny's steady strokes rubbed his thick rod against my prostate. I shivered in ecstasy. I needed both hands to steady myself against the persistent pounding. Danny had both of his hands on my hips steadying himself, so I was surprised when I felt another hand grasp my cock and start pulling and stroking it.

My own sister was jerking me off as a man pounded the shit out of my ass!

When Danny noticed this, he pushed my head downwards. My arms collapsed and I found myself with my face up against Cassie's muff. If sis was willing to fist my dick, I guess I had to be "polite" to her. I gave her cunt a few tentative licks. She moaned and used her free hand to push my face more firmly into her crotch.

But I had taken only a couple of licks before Danny changed things around. Grasping hold of me, he rolled over on his back. His cock slipped out of my ass. He told me to sit on his cock. This was new for me, being on top. I steadied his cock with one hand as I lowered myself on his dick. It slid inside me easily but when I bent down to kiss him it slipped out again. I turned around with my back to his face, and dropped onto his cock again. This time, he slid inside and stayed.

In fact, my weight dropping on his cock, drove his dick deeper into me than any cock had ever been before. With his strong hands under my thighs, Danny helped me to bounce up and down on his dick. I was seeing stars as his dick ran across my prostate.

Cassie was on the floor taking pictures of the lewd sight on me dressed as Sindy (well, undressed as Sindy!) bouncing up and down on a man's dick as my own stiff rigid rod bounced around wildly.

Suddenly Danny's strong hands held me positioned in mid air and he furiously rammed his cock in and out of me. He screamed that he was cumming and I felt my bowels being washed by his cum. My own dickie let loose and I fountained six or seven streams of goo high into the air.

We collapsed on the bed, both of us gasping for air. As we started to regain our breath, Danny reached into his bedside drawer again and pulled something out. As his softening cock slithered out of my ass, he pushed a butt plug up inside me. I had never seen one of these before (and would not actually see this one until I got home.) As he kissed me, Danny suggested that I keep the plug in my ass until I got home. That way I could enjoy the feeling of his cum sloshing around inside of me for awhile longer.

We were momentarily distracted by soft moans from the floor. Cassie had just frigged herself to her own climax, and collapsed giggling onto the carpet.

Danny and I exchanged email addresses before Cassie and I straightened ourselves up. Danny decided that he was just going to stay in his room for the rest of the night.

As Cassie and I descended once again to the ground floor, I was walking strangely, due to the plug in my ass. And of course, because of the pounding my ass had just taken.

The party was winding down and we decided to leave. We paused outside to each have a cigarette. As we smoked, Cassie told me that I had been utterly, fucking amazing! When she had suggested that I dress up for one date, she had never thought I would turn into such a cock hound! I blushed at the term, but had to admit to her that I enjoyed being a cock tease and was eager for more outrageous experiences! Carl had been boring for SO long. Sindy wanted excitement!

As we ground our cigarettes under our high heels, Cassie gave me a long passionate kiss and we swapped tongues hungrily. She gave my cock a gentle squeeze and then we hopped into the car.

On the way home, I made sure she stayed awake behind the wheel. At one point she confided in me that over the last few weeks Johnny had been hinting to her that he would like to try fucking her in the ass. She had no idea why that idea had suddenly come into his head (of course, I knew why!) and she had resisted any suggestions. But after watching me enjoy it so much......

My ride home had been a bit uncomfortable due to the butt plug in my ass. I had squirmed about on the seat a few times. When we got home I headed straight for the bathroom. It took me a few tries to properly grip the base of the plug so that I could pull it out. Thankfully I was sitting on the toilet because as I got the thing out, Danny's lovely cum slid out of my ass and into the bowl.

I washed off the plug and then brushed my teeth. As I did, I could feel the air wafting up into my ass. Lying in bed, I was very conscious of my ass gaping open. It was not an unpleasant feeling. As I drifted off to sleep that night, I tried to recall the number of guys I had had sex with, but kept losing track. God, I think I was becoming addicted to sex!

Chapter 10 - Revelations

The next week was eventful. Once again on Tuesday I met up with Johnny after school so that we could share a few moments of pleasure together. I think I enjoyed the kissing just as much as I did the feeling of his long cock stuffed up my pleasure canal! But I was feeling guilty about having sex with my sister's boyfriend. I needed a steady boyfriend of my own, or rather I needed a steady COCK of my own!

Danny looked to be a good candidate for a steady boyfriend, particularly because he had no problem with my cock. We began talking by email and tentatively set up a date for the next Saturday night.

On the Wednesday, I skipped out of my afternoon classes and Cassie took me shopping. I had my winnings, or rather "losings" from the blow job contest, plus some other money I had set aside. First visit was to one of her hair salons and Cassie convinced me to get my hair dyed just a bit more blonde with some silver highlights streaked through it. We also had my eyebrows tweezed a little bit into slightly more feminine arches. My nails were trimmed and buffed and a clear varnish applied. I liked the femme make over stuff, but still had to live my daily life as Carl.

Remembering how much I liked Danny's hairless groin, I also was brave and got a Brazilian wax - all the hair was stripped from my groin. That night when I got home, I posed in front of the mirror and admired my hairless cock and balls. There was something very erotic about the hairlessness and it did not take long before I pulled out my bottle of lube and knelt on the floor positioning the head of my dildo at my ass.

The dildo... one of my other purchases. Cassie and I bought me a couple more cute outfits, plus some accessories like fishnet stockings. Our final stop was an adult sex shop where we wandered around for awhile. I eventually purchased some flavoured lube, a couple of shemale DVDs from the discount bin and a seven inch rubber cock. I had always thought of dildos as being long plastic vibrators, and I was surprised to find realistic looking cocks. I wanted one to practise deep throating, but knew it would also end up in my ass a lot. The dildo came with a suction cup base.

So indeed that night, I had the dildo attached to my bedroom wall about eighteen inches off the floor and I pushed my ass back on to it and it sank slowly into my ass. For the next ten minutes I pounded my ass back and forth on the fake cock as I ran my hands along my hairless cock. My orgasm was great, but the whole experience left me empty. I needed a warm body attached to that cock!