Where Fantasy Meets Reality

By College Kid

Published on Sep 1, 2006

Gay

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Disclaimer and stuff: Don't read this story if it is illegal for you to do so wherever you live. If gay sex, offends you, this story is not for you. The characters in this story do not practice safe sex, you should. This story contains explicit sex between minors, in the real world minors don't have sex. I think that covers it all!

Please don't distribute this story or post it elsewhere without my permission. I'll likely grant it but I need to know where this thing is going ! :)

Pre-amble: The first installment of this story is mostly background stuff. There is some sex, but I don't go into much detail. Much of this story is based on reality, though names have been changed to protect the innocent. Fact and fiction however, blur often in this story. Many of the experiences I describe happened exactly as I wrote them. Others are simply what could have been, or alternate endings to events in my life that my dark depraved self wishes had gone differently. Most of the really wild stuff is pure fantasy, with only a trace of truth but what's hotter than a fantasy right?

This story details events through my life from the time I was 13 right up until the present. Everything but the sex stuff and events relating to the sex stuff is true. The first few installations will deal mostly with high school, the last few with college. If you want to know where reality and fantasy meet you can ask me :)

I've written other short stories before, and other series but this is my first attempt at a sex series, I hope you all enjoy. Please do e-mail me at gaycollegekid@hotmail.com to tell me what you think. Tell me what you'd like to see, and I might incorporate it. Just give me some feedback ! Further chapters of the story probably won't be forthcoming if there is no response to my story because as an author it is the readers reaction that drives you.

About me: I'm a 21 year old university student, attending school in Canada. I love sex and am very kinky (as if you won't know that by the end of this story). I'm 6 feet tall, with what others describe as brown or auburn hair. Really it's a mixture of all kinds of colours from blond to brown to red but blonde works. I have dark brown eyes, a toned body and Im always looking to meet new people to chat with and explore new things so don't hesitate when you e-mail me.

Happy wanking!

My sexual life began when I was 12 or 13. It's all a bit fuzzy now, but I remember that I'd just started jacking off not long before and I'd been able to cum for a while. It started with a neighborhood boy who I'd been best friends with since we were 2 or 3 (even fuzzier). He lived a few houses down and our parents never had any problems with us sleeping over at each other's houses. Our play had actually started when we were 8 or 9 and then stopped for a while, but our actual sex play began just as puberty set in.

As I said, I'd been jerking off for a while by this point and like most boys discovering their sexuality everything and anything related to sex got me going. To that end, I'd been watching late night porno movies on payperview when my parents were out on one of those illegal descrambler boxes that used to be available. I loved to watch the porn stars big dicks slide in and out of mouths and pussies and see their asses as they pounded some chick to a faked orgasm. When the male porn actors were younger, in their 20s or so, it was a special reward for me. I wasn't too interested in guys much older than myself then and I still am not now. That said, the 11pm and onwards descrambled pornos were all I had, since the internet was still in its fledgling state and I wouldn't have known what to do with it anyways.

Often, when my parents had gone out with friends or to some other social function, I'd wait patiently until 11pm then run into my parent's bedroom and turn on the porn channels and frig my little dick until I exploded. When the opportunity to do so in front of my best friend presented itself I jumped at the opportunity. Of course, you all remember what it was like at that age, anyone who had seen porn of any sort was revered, anyone who could show it to their friends was a God. It was a Saturday night, a night which my parents always saw friends on and I was having a sleepover with that good friend, his name was Matthew, though I called him Matty at the time. Anyways, around 11 o'clock Matty and I were in my parents bedroom when I flipped on the porn channel. Matty was enthralled immediately, it was his first time seeing a porno. I did not know that he, unlike me, could not yet shoot a load. I was around for his first wet orgasm ever though, and I will never forget that moment.

After watching for a bit and getting sufficiently aroused, I asked Matty if he'd like to film our own porno. When I think back on it, that was a pretty daring and risky move on my part, not the sort of thing I'd try now but it worked and moments later we were in my parents bedroom doing strip teases for the camera and playing with ourselves for each other's entertainment. I should probably describe Matty at this point. He was almost elfin in his appearance. Lithe body, longish blond hair, sleek seductive hips and a pert little ass, for a first time I got the real pick of the litter.

In the following years, until we were both 14 or so he and I got together a number of times for our sexual escapades. We filmed it most of the times we were at my house, and I stole one of my dad's mini-vhs tapes from the camcorder to keep as our personal porno storage. Later events unfortunately led to the necessary destruction of all that evidence, man what I'd give to have those tapes today though... man what I'd give.

Despite the number of times Matty and I fooled around, we never really got too far in our sex play. There were a lot of blowjobs, plenty of handjobs, and rubbing and licking of all sorts but we never got around to real anal sex. As far as we knew anal sex was a myth, all you could really do was rub your cock up and down the other boy's crack, so that's what we did. My dick at the time was roughly 4 inches, his was just really really small, I remember thinking that even at the time. We assumed my cock was just too big to fit up his asshole and we knew his was too small to do any kind of real penetrating. I rubbed my cock up and down his crack a lot ( a crack that was too often left unclean ) and he poked around between my cheeks with his micro-dick enough times, but we never had any real anal sex.

Near the end of our sexual encounters, I had already started developing my "sexual personality." Basically, I was starting to come into my own and figure out my likes and dislikes in sex, probably long before any of my peers. I knew that I had an obsession with other boy's asses, but I wasn't quite sure what I liked about them. I knew that I found the smell of Matty's really exciting, but I didn't really get much beyond that. I had also already developed a burgeoning interest in piss play, something I think I developed at summer camp thanks to another boy named Cody who really enjoyed peeing on other boys. Matty indulged me to an extent, dribbling some piss on my chest once and rubbing it in but it never went further than that.

I guess one last notable experience with Matty that I should mention, one that I still think of often was the time we were in my room on my bed. I was lying with my back on a pillow while he kneeled between my legs and sucked me off. Nothing special about that, except that during the blowjob Matty started to cum uncontrollably all over my legs. He hadn't touched himself, he hadn't been touching himself, he was just so turned on by the taste of my cock that he just began to ejaculate a constant stream of semen. He didn't stop cumming until he stopped blowing me incredibly, and my bed was soaked with his cum, an experience, which regretfully, I doubt I will ever see repeated. I guess I was just really fucking hot, even back then.

Fucking around with Matty ended when he moved downtown and I moved to a suburb. It was a long drive to see each other, and our time together slowly started to diminish. By the time I was 15 we'd stopped seeing each other entirely. It wasn't just the distance, he'd gotten into pot, something which scared me at the time (I'd practically been indoctrinated from birth) and I didn't like a lot of his friends, since he now lived in a particularly rich area of the city, and you better believe his friends acted like they knew it.

With that era of my life over, I went back to jerking off alone in my bed, until sometime during my first year of high school I got my own computer and discovered the wonderful world of free online porn.

High school, for me, was a great experience. I know a lot of people hate high school for one reason or another, but for me it was great from beginning to finish. Even though I entered the big school knowing only 3 people, none of whom were particularly good friends by the end of the first day I'd already found a female locker buddy a year older than myself, and befriended some of the most popular kids my age who'd come from the bigger feeder schools. I guess the fact that I had come from a private school and most of them had come from public schools meant that we were slightly exotic and new to each other and that was all we needed.

I was quickly established in the school. I had my own crowd of friends who I saw outside of school, but within the school I was also a 'floater.' I wasn't really concerned with what people thought about me, nor did I share in many of the juvenile prejudices that usually permeate the high school. I was pretty much well liked by most of my co-evils and most of the teachers I had also liked me which worked out well when I needed something. Grade 9 and 10 there were still some kids who didn't like me. They either viewed me as a brown noser because I never got in trouble in class, or as a nerd because I got good grades. The fact that I was friends with many of these people's friends meant that I was spared any of the harassment others received, but there was always the offhand comment, or the discouraging remark. It didn't bother me too much, and by grade 12 when I graduated my best friend and I pretty much ran the school. We were feared, or respected by everyone, teachers and students alike. How we earned those positions is a bit of a long and boring story, maybe I'll get back to it in another chapter but suffice it to say in my day to day life I was totally in control, which was in total contrast to the dark fantasies I had at night.

One of my regular fantasies involved - coincidentally - a boy named Matt. When I first saw him he was damn good looking, easily my match in the looks department, although considerably shorter than my 6 feet. He had a tanned complexion, a toned but pretty skinny body, chestnut brown hair that he wore in a fairly basic style and a cute boyish face. There were a lot of cute boys in my high school though, so very many to choose from, what made Matt a resident figure of my fantasies was a conversation I had with his best friend Jordan, one of my first friends at the school, in math class. I don't remember all of the specifics, but he'd been talking with me and a girl sitting at a desk behind us about how he, and that girl, had been measuring his penis over the phone. He seemed very proud of the fact that at 14 or 15 he had a 6 and a half inch penis.

The conversation somehow turned to the topic of matt, and how he had a HUGE cock. I already knew Jordan's dick was 6 and a half inches which meant Matt must have been much bigger, 8 inches at least I figured, maybe more?!? I distinctly remember Jordan looking at me and saying, "it's probably bigger than yours!" I guess my tremendous height - at the time, sigh - led him to believe I must have had a similarly large penis. I let him hang onto that thought secretly knowing that my cock was only about 5 inches. My cock never got any bigger and I didn't get any taller and by graduation many of the boys had surpassed me in the height department, and even more in the cock department I suspect, oh well.

Back to Matt, the revelation that he had a huge cock was a major turn on for me. I loved imagining what his big piece would look like attached to his smaller frame. Soft, hard, it didn't matter, Matt's big cock was a constant fantasy of mine. His fine body and huge cock were not all that attracted me to Matt though. As I became more interested in him, I started noticing more. Matt was an all around athlete, good at every sport and a member of a number of the school's teams. He had that cocky self-assured attitude that makes me so horny and he was a pretty intelligent guy too. He never got my grades, but he was smarter than the average guy in his circle.

I'm pretty sure my rim fantasies started with matt. I caught a couple glimpses of his bare butt when we were changing for our gym class ( I never got naked but he did often enough) His butt was perfect, two nicely rounded globes, not as bubbled as I would have liked but with his trim frame the slightly more muscular look really suited him. He had a small spattering of hair poking out the crevice of his crack but otherwise was entirely smooth. I would lie in bed at night imagining myself between his smooth as cheeks licking away as he moaned in pleasure and spewed dirty talk all the while. Little did I know I'd eventually get to live out this fantasy, only not how I expected, nor where I would have liked or when.

Being that I was a closet case, I never made a move on Matt in that first year, besides, I was too busy making new friends, having new experiences and doing the myriad of other things you do in your first year of high school. I did however do the online thing. I hooked up with a couple guys on the internet. None of the experiences was particularly good. One guy sent me a fake picture and when he picked me up I was so shocked I almost left the car and went back into my house. However, because of the lie I'd told to explain where I was going that night to my parents and how hard it would be to make up a new one I decided to go to the movie with him anyways. It ended up with us trading suck jobs in his car behind some warehouse after the movie. He sucked me to orgasm and once I'd come I told him I had to be home leaving him unfulfilled. I'd later learn just how frustrating that sort of thing could be for a person.

Another guy I met was two year older than me. He showed up at my house one evening when my parents and sister were out. He definitely wasn't bad looking, and he had the appeal of being a slightly older, more experienced playmate but he was one of those high strung, drama queen, out of the closet downtown, trend loving, confused as hell gay teens. He rang my doorbell and when I greeted him he asked if we could stay outside for a bit. He smoked a cigarette, sighed a lot and told me about his troubled life in the intervals between the awkward silence. We went to my bedroom eventually and he asked to see some of my porn collection. I showed him some of my favorites as he casually groped himself, and later me. I wanted so badly to suck him and for him to fuck me but alas it wasn't to be. My housekeeper, sister, and parents all came home shortly after we'd started getting randy (mostly because he showed up really late) and we traded a quick (and more importantly, quiet) handjob and he left. We never met up again, he probably gives blowjobs for crack now, or died of an overdose or something.

The internet experiences were what would eventually lead to my more exciting sexual encounters. It wasn't because I met great sexual dynamos on the net, only that one day I would end up talking to someone who knew me very well online and it would begin a series of events that would set me on the path to being a teenage sex slave.

It was halfway through the first semester of my second year of high school. I was still on the path towards becoming a well known figure of my year, not nearly the dominant force I was to become, nor aware of the submissive slut I'd be turned into before the year was up. As I sometimes did on boring weeknights I logged into one of the gay teen chatrooms to see if I could either A) get my rocks off dirty talking to some random guy or B) meet someone I might hook up with. I chatted with a few guys but either they bored me or they disappeared on me when the going got hot, usual bullshit.

Finally, I found one guy with a name like "suckme17" or "blowme17" I don't remember. He and I chatted for a bit about normal stuff, hobbies, school, parents etc. The guy had been slow to respond to me so I figured he was involved in other conversations but at least he had a quick wit and a pulse. Abruptly he changed the subject to sex. He asked me if I was a top or a bottom, I replied bottom. He asked what I was into, I gave some lame response. We got a little racy and I got really hot. Soon though, suckme17 wanted more, he wanted to chat about the kinkier side of sex. Tying me up, spanking me, that sort of thing. I wasn't sure about it but I was so hot, I figured I'd give him what he wanted and hope I'd get something out of the exchange.

I was getting something out of it, the chat made me horny as hell. I kept edging on, prolonging my orgasm so it would be better when the boy proposed that I say some things in the main chat channel we'd met in. I was so horny at that point I would have done just about anything. I said some pretty messed up stuff in the chat as I recall, "suckme17 owns me." "I live to suck off suckme17" After a few minutes of this I received a private message from another chat room user whose name was an unintelligible mix of letters and numbers. He asked me if I was into being a little slaveboy. In my heightened state of arousal I responded, "yes" hoping to get him going and maybe get something from him too. The chat with suckme17 died suddenly, apparently he'd climaxed and was done with me so I picked up with the new guy, who described himself as being my age - 15.

He asked lots of questions, most of them seemed a bit strange to me, but they turned me on as well.

"Do you like to lick bums?" he asked.

After deciding whether or not it would be cool to admit to this guy I did, I replied, "yea, a lot." I went on to tell him that I really loved licking an ass and that I fantasized about doing it to a school friend Matt all the time. I figured if he'd asked, he was probably into it too and wouldn't think I was weird.

I was wrong, his response back was, "That's gross, do you like to take it up the ass too?" Thinking this one was a sure fire, I responded that I did. The questions kept up, and got increasingly strange as they went on. "Would you drink my piss?" "Could I smack you on the back of the head after I came up your ass?" "Would you take me and my buddies one after the other?" I was kind of getting off on him thinking I was a dirty boy and knowing it was probably getting him hot anyways, so I replied yes to a series of questions I knew I would never actually go through with in reality.

After a barrage of questions, the mystery boy asked me where I lived. I told him I was from Toronto, he seemed amazed, telling me he was also from Toronto. We found out that we were also from the same suburb. He asked me for a picture, and promised one in return. I sent him mine and after a pause once he'd received it the boy disappeared. I felt dejected, assuming he just hadn't liked my pic. Little did I know, the truth of the situation would affect the rest of my life.

The next day in school I was headed to my locker to grab some textbooks for the next class, when I was confronted from behind, "Hey Cody!" I turned to face the voice, my locker to my back and in front of me stood two guys from my grade: Josh and Tim. We were in a slightly secluded area between rows of lockers and no one was really around at the time thankfully because the next words to come out of Josh's mouth was, "Hey Cody, wanna give me a rim job?" "Me too!" bellowed Tim.

I gave both boys a long drawn out sarcastic "Nooooo thanks!" Turning around I started entering the combination for my locker. The boys retreated and I went about my business.

After the next period at lunch I was talking with a crowd of friends when Josh and Tim approached me again. They signaled to me and called me aside, apparently they wanted to talk. I gave them a suspicious glare before walking over to the spot where they were standing. "What do you want?" I demanded.

Instead of answering my question Josh shot back another question, "Do you want to lick our asses?" he said with a smirk. I huffed, turned around on my heel and marched back to the group I'd been talking to earlier. As I stood talking I began to wonder if this might have something to do with my chat the previous night. I wondered whether Josh and Tim might be gay, but then realized I'd only talked to one person the night before. Josh and Tim weren't the best looking guys but they were definitely fuckable if not the subject of my jerk off fantasies.

Both Josh and Tim were fairly well known in our year. They weren't the most popular but they were up there on the social ladder. Both were sort of known for being shit disturbers in class and though I'd had few classes with them I knew them well enough for that reason. They knew me because I always had something to contribute in class discussions, and likely because at the time I was good friends with one of the most sought after girls in the grade.

Things were pretty quiet until Tuesday of the next week. I was walking into one of the school's bathrooms to take a piss when I heard my name from behind me. Sure enough Josh and Tim were following me into the bathroom. I wasn't particularly phased, it was a safe school and I didn't think they'd try anything. I went into one of the stalls to take my piss but I heard muffled talking coming from outside the stall followed by a clicking noise. When I finished my piss I stepped out of the stall and proceeded to the sink to wash my hands. Josh and Tim approached me from around a corner, a stack of papers in Josh's right hand.

"Listen Cody," said Josh. "We know what you are." I gave him a puzzled look and he took a step closer towards me shaking the stack of papers above his head. When he was in range he thrust the papers into my hands and simply said, "read." I was shocked to find out that it was indeed a transcript of my conversation with the numbers and letters guy online from the week before.

"So," I thought, "Josh and Tim are gay."

Easily picking up on the shock in my face Josh began again, "Now you know why we've been asking for rim jobs all week."

I smiled at him for a second then replied, "I didn't think you guys were gay, was it both of you I was talking to that night?" My comment drew a quick smack in the head from Tim.

"We're not the fags you fag." Josh and Tim chuckled at the 'joke'. "We were looking to have a laugh getting fags to spill all their gay shit to us. We never thought we'd meet someone we knew in there but SURPRISE we found you." Tim threw back some hair that had fallen into his eyes, grinned at me, then continued. "You were going on about how much you liked to lick ass, and how good it made guys feel when you did it, so when we found out it was you we figured we'd find out for ourselves."

It was Josh's turn to speak now and being the more loud and aggressive of the two he set things in motion. "The door is locked." He stated simply. "You can try and get out, but you probably wont before one of us grabs you. Even if you did get out, we'd just tell everyone about our little chat and let them decide what to do with you." Of course, I knew that the chat logs could not be directly tied to me but being that I didn't really play sports very well, except for Hockey (not sure why it was that way), I was friends with lots of girls but was never actually seen dating one, and the fact that there was no malice between Josh and Tim and myself nor anything to be gained by them doing this I figured a number of my classmates would buy it. More importantly, I was freaking out and I wasn't thinking straight and acted hastily.

With the game over in record time, I submitted, hoping that by doing so I would avoid something far worse. "What do you want?" I asked. "Rim jobs," came the simple reply from Tim. Josh nodded in the affirmative.

"Here!?" I burst out.

"Door's locked," Josh replied.

"But what if a teacher comes by, what if the Janitor comes with the key?" I pleaded.

"We'll be quick." Josh said. "Just a few licks and we'll let you go."

I looked at Josh and then at Tim, and again sized up my situation. I seriously considered bolting again at this point but the prospect of being the class fag and being tortured for it for the rest of high school kept me in place. Once I'd resigned myself to my fate, I started thinking about other things. I looked at my two classmates noticing them for the first time in detail. Josh was about 5'9 or 10, black spiky hair, white skin with a rosy complexion. He had a large mouth punctuated by large lips and a cute enough face. In contrast to Tim he had a bulkier body, having put on some size playing sports and probably lifting some weights. Tim was slightly taller, maybe 5'11, almost lanky and stood straight as a board. He had light brown hair that hung long over his ears, sometimes falling into his eyes. His skin was a very light olive colour, just slightly lighter than what you might expect of a person born in Spain but his features didn't seem European, or really from anywhere. A typical North American mutt.

For the first time I started wondering what was underneath the clothes of these boys, how big were their cocks, what did their balls look like, did they have nice asses? I was interrupted from my reverie when Josh yanked on my Abercrombie sweatshirt and pulled me towards one of the stalls. He walked in first and pulled me in behind him. Wasting no time, as promised, he started fumbling with his pants and pulled them down revealing a pair of white boxers with green and blue geometric shapes all over them. Before he pulled those down, I again tried to reassure myself that I'd made the right decision.

"You won't tell anyone if I do this right? I mean you aren't going to spread it around the school?" I asked.

"I promise," Josh said, turning around to face me briefly. Then he hooked his thumb into the waistband of his boxers, yanked them down, bent over and in a muffled voice said, "get to it, lick my ass." Josh's ass was probably his best feature. Big and bubbly, my favorite. His as cheeks had the same rosy flush as did his face, they were smooth with a nice tuft of hair poofing out his crack. I didn't have much time to think about it though before Josh reminded me I should have my tongue in his crack.

I got on my knees behind him and tentatively brought my head towards his ass. I'd dreamt of doing this many times when I jerked off, but actually doing it was something else. I stared at his hole, and at his ass and like a deer caught in the headlights I didn't move. Josh was impatient though and quickly grabbed the back of my head and pulled me into his butt crack. The first thing I noticed was the smell. I hadn't noticed anything from afar, but up close it was very evident just where my face was. I could feel the hairs in his crevice rubbing up against my cheeks, I could feel my nose pressed against his hole and all I could see was the cheeks of his ass. By the time I'd adjusted to being in Josh's ass he was yanking my hair up and down rubbing my face in it demanding again and again that I start licking his hole or else. Despite the situation, I was getting really turned on and without thinking I went in with gusto. I did my best on my very first rim job, licking up and down his crack making little circles on his hole and generally trying to make him feel really good.

After about 5 minutes of this treatment Josh pulled my head from his ass and pushed me backwards causing me to land on my ass. He stood up, did up his pants and said, "that was good fag. But next time you'll have to do better." Before I could ponder the meaning of "next time," Tim told me it was his turn. This time told me to strip off my pants. He said he thought it would be cool to see how hard I got from putting my tongue in his ass. "How did he know I was hard?" I wondered. I knew my dick wasn't big enough to be noticed even if it was hard when I was wearing the baggy jeans that were so in back then.

Figuring it would make him happy and guessing that I'd be forced eventually even if I refused I yielded and pulled my pants and boxers off. My hard five inch dick stood out from my groin proudly, a fact which Josh quickly picked up on. "Got a woody from sucking my ass eh?" he said. I blushed, and turned away from him to see Tim slowly working down his own pants. I was happy we were outside the stall this time, the cramped position I'd had to kneel in was painful.

Tim backed up so his now naked ass was in my face and slowly rubbed it up and down my face, taking pleasure in knowing that he was doing something so dirty to me. I heard Josh moving around behind me but I could only hear him when he said, "Jerk off fag. You obviously want to." He was right, so I did. I started stroking my cock furiously as Tim continued to grind his ass against my face in every conceivable way. When he was through with that game he gave me the simple "lick" command and I got to work.

Josh was moving around encouraging Tim as I licked the crack of his bony ass. At one point I heard some clicking but ignored it, already starting to worry that someone was going to bust in on us. It was a wonder I hadn't heard anyone trying to come in yet. When Tim was satisfied with my ass licking he pulled back. Unlike Josh, Tim had sprung a boner it was about 6 inches long and the tip was wet with precum. I was almost proud of myself for having done such a good job.

My temporary elation was shattered when Josh came around in front of me and waved a camera in my face. "I have pictures of you jerking off licking Tim's crack." He said matter-of-factly. "You're ours now, you do what we tell you or these go around the school." I'd been tricked, this whole thing was a setup to get a picture of me so I'd really be under their thumbs. I now understood why they were willing to take the risk of doing this at school, they'd never have another opportunity since we never saw each other outside of class. Before I even had time to think about trying to steal the camera, and before I even had a chance to pull up my pants, Josh and Tim were walking towards the door. Josh turned around threw me a wicked smile and said, "We'll be calling you when we want you again. Next time you better not give us a hard time."

I considered running to the principal then, or contacting the police. I knew if I got the police I could probably prevent the picture or the logs from ever being spread. I didn't go call the police however, I pulled up my pants washed off my face and stared at myself for a few minutes deep in thought. I wouldn't go tell the police. Why? Because I'd liked it.

To be continued...

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