Let me start out by saying that this is a complete and total work of fiction. This story also will depict, at times, sexual activity between teenage boys. If this is in any way aginst the law in your state, or if you are not old enough to view such material, i suggest you leave now, but if not, continue on and enjoy the story.
Chronicles of a Mispent Youth Part 1:
09-19-1996
I've decided to start this journal because of some events that have occured over the last couple of weeks in my life, and I thought I would jot them down for proterity and what not. Let me start off by introducing myself. My name is Ryan, I am 16 years old, and I live in an all boys boarding school in upstate New York. I have been living here for about 5 years now, and it has become just as much of a home as anywhere else I have lived in my life. I still spend summer and holidays with my family, but when it comes to the everyday events of my life, they occur here at the school. The boys here are like my brothers. We do everything together, and every significant event that has occured in my life, has occured right here in this school. Well, I am a normal enough guy, I make good grades and stuff, and I like all kinds of sports. I try to stay active to keep myself in shape by playing football, baseball, basketball, and soccer. I don't really excell in any sport, but I can pretty much hold my own against just about anybody. I am 5'9", 135 lbs, brown hair, and brown eyes, I have a pretty good body, its just not as defined as I would like it to be, but I am definately working on that.
As most people could probably understand that growing up in an all boys school, that you are pretty much limited to the types of sexual activities you can partake in, but most guys here are pretty cool about such things, and they realize that "a guy has to do what a guy has to do." Well, I discovered a couple of years ago that I actually enjoyed being surounded by these hot guys day in and day out. I didn't dare let anyone know my secret, but it was there inside of me bursting to get out. I am gay, it has taken me months to actually say that outloud (of course to myself when noone else is around).
Now as I mentioned before the guys at the school usually did things sexually together, but they just got off and left, there was no feeling between the two, or more, participants. I made it a mission to try and find someone that I could connect with, and share my intermost thoughts with, someone I could love and he could love me back. I wanted a relationship, not some fleeting hand job in the bathroom stalls, or some quick blowjob before lights out. I wanted a boyfriend, and I was going to make it my point, no my mission, to find one, even if I got killed in the process.
I remember it as if it were yesterday, the day that I started my mission. I began to look through certain prospects in my classes. I knew that to get to some of the boys I had to make it a sexual encounter first, and then I could probably talk to them about their feelings afterwards. I started with the first guy I had ever fooled around with at the school. Chris Phillips was the hottest guy in the class, and the richest, and most popular. Chris was the guy that everyone went to when they needed to get something that they couldn't otherwise access themselves. He ran a pretty good business that way, and that was one of the reasons that he was so popular with everyone, and another reason was that he never mentioned to anyone what someone else asked him to get for them, this wasn't a policy of his, but it was sort of an unwritten rule, and I decided to use this to my advantage.
It was late one night, about thirty minutes before lights out, and I knew that this was the time that Chris always showered, so I decided to approach him while he was in the shower, and I thought more vulnerable. I walked into the shower, and I immediately heard the unmistakable sound of a shower running, and I was delighted when I could only make out the sound of one showerhead. I slowly approached the shower, and when I saw Chris standing there with his back turned to me, I almost gasped at his sheer beauty. He has the greatest body I have ever seen on a boy, and to see him standing there with the water slowly trickling down his back was unbeleavably erotic. Now, let me describe him to you before I get any further in my story. Chris is about 6' tall, he has blond hair and blue eyes, he is about 165 lbs of pure and solid muscle, he has a really tight body with a six pack and a tan that makes him the envy of every other boy in the school. Chris also has the best ass in the school, and I was getting a good look at those nice tight cheeks right now. Before I realized it, I had been standing there for a good two minutes, and it appeared that Chris was getting ready to finish his shower, so I went and got in position at one of the sinks in the adjoining room, and started to shave (even though I didn't really have anything to shave, most of the guys were doing it, and I just thought I would do it to fit in). Anyways, I had gotten the water to my desired temperature, and I started lathering up my face when Chris walked into the room. He took up a space in the sink next to me, and began shaving as well. He was only wearing a towell, and I was starting to get a little nervous about the conversation I was about to have with this gorgeous half naked guy standing next to me.
"Hey Ryan, how's it going?" Chris asked making eye contact with me for the first time.
"Pretty good, just running a little late getting ready for bed, you know how it is." I replied trying to sound as normal as possible.
"Yeah, I always like to shower this late, its usually alot less crowded in here, and I like to be alone in the shower if you know what I mean." Chris said with a wink
"Yeah, I know what you mean." I replied trying to stay cool "Hey Chris, you think you could get something for me? It's kinda personal."
"Yeah sure, trust me, I don't think I've heard anything yet that has surprised me." He replied not taking his eyes away from the mirror.
"I was wondering if you could get me some K-Y Jelly." I blurted it out almost unsure of exactly if I had said it outloud
"Yeah sure, you would actually be surprised at how many guys ask for that stuff, I actually have some in my room if you could wait here for a second." Chris replied, not even acting like he was surprised at my request.
After he finished shaving, which I am sure was more out of neccesity than to fit in, he told me to wait right there, and he would be right back. He left the bathroom, and I was nearly shaking with nerves when a few seconds later, he reentered the bathroom with something that looked like a tube of toothpaste in his hand. He handed the tube to me, and I looked at it, it had the words KY on the label. I put the tube in my pocket and told him thanks, and then turned back towards the sink and began to brush my teeth. He did the same thing, he had left the towel back at the room, and he was standing there in just his boxer shorts.
"So, you finally get tired of jerking off with just your hand and a little spit, I know what you mean, its allot better with that stuff." He said nonchalantly
"No, I was kinda gonna use it for another kind of fun." I said looking at him with a slight grin on my face.
"No shit. Who's the lucky guy?" Chris said in a joking manner as most of the guys would while standing in the bathroom usually half naked.
I decided to continue with the joke, and my mission both at the same time. "You." I stated continuing with the joke.
Chris looked at me a little startled at first but I guess he figured I was just joking, so he decided to go along with it.
"Oh, I see now, you were going to get me in here, and wow me with your charm, and then take advantage of me in one of the bathroom stalls is that it?" Chris laughed
"Something like that, but I was kinda hoping that you would be the one to take advantage of me." I said completely taking the joking tone out of my voice. I was really nervous and scared, but I decided that I had gone that far, and couldn't really turn back now.
I turned toward Chris, and allowed myself to make eye contact with him so he would know that I wasn't joking anymore. I decided that if he freaked out, then he would leave, if he didn't he would stay there, and the night would take a much more interesting turn. When his eyes met mine, I knew that I had him. Without saying a word, he started walking towards one of the bathroom stalls. I stood by the sinks frozen, not wanting to do anything to scare him off. When he reached the farthest stall, he started to go in, but he suddenly stopped and turned back around towards me.
"You coming?" He stated a little seductively.
"Not yet." I said, and made my way toward the same stall that he was in.
Once we were both in the stall, all conversation ceased to exsist. I started to slowly rub my hands up and down his chiseled chest, I was surprised at how soft and smooth his hairless chest was. I began to slowly pay attention to each nipple, which I had read was some kind of erogenous zone or something like that, it was supposed to drive the guys crazy. Chris didn't seem to interested in any erogenous zone, or any other zone for that matter. He began to put pressure on my shoulders, lowering me down till I was sitting on the toilet with his crotch right in my face. I knew exactley what he wanted me to do, so I didn't waste any time in slipping my hand into the fly of his boxer shorts, I began to slowly message his cock, trying to get it as hard as possible before I exposed it for the first time. When I got him to the point that I had wanted him to be at, I slowly began to release his cock from its silk confines. When his cock came into view, my breath was nearly taken away. It wasn't really the biggest cock I had ever seen, but it was the most beautiful thing I had ever seen. It was about 6.5" long, and pretty thick, but the thickness was well proportioned throughout the entire length of the shaft. I wasted no time, and slowly began to insert the head of his cock into my mouth. This action caused a moan to escape the lips of this gorgeous hunk. As I began to slowly take his cock in and out of my mouth, he began a slow rocking motion as if he were fucking my mouth. As he was getting closer to cumming I got an idea. I slowly took his cock out of my mouth.
"What are you doing?" Chris asked a little pissed off that I had stopped the blow job that I was giving him.
"I have an idea, hold on." I reached down and pulled out the tube of KY that he had given me earlier. "I want you to fuck me up the ass." I said as I applied a good deal of the lubricant into my hand and began to lube up his cock with slow strokes. "What do you think?" I said looking up at him.
Chris was really getting into the lubricated hand job that I was giving him, so it didn't really take much to get him to agree. "Sure, just make it quick, I don't think I can hold on much longer." He said breathing really heavily
I got up out of my sitting position, and began to take off my shorts, and this was also the first time I had release my cock from the fabric confines that had been holding it in throughout this entire episode. I was amazed at how hard my 6" cock had become, and even more amazed by the amount of precum that was dripping out the head. I stood up, and let my pants fall down to my ankles, then I began to apply a generous amount of KY to my still virgin ass.
When I thought I was lubricated enough, I turned around, bent over and placed my hands on the seat of the toilet, thinking that this would be the best position for Chris to enter me.
"Go slowly until I get used to it." I told Chris, a little afraid of the pain that I knew was going to come with him entering my ass.
I tried to relax as Chris started applying pressure with his cock to my unwelcoming hole. He kept applying pressure until finally with a hard thrust, the head of his cock entered my ass. I let out a muffled scream at the amount of pain that was being applied to my rectum. Chris held his position there until I was ready. When I felt that I could handle more, I slowly started moving back on his cock. I guess he thought that it was an invitation that I was ready for more, so in one thrust he rammed his entire cock up my ass. The pain was excrusiating, I had never felt anything this painful before in my life, and I thought I was going to pass out.
"GOD DAMMIT!!!!!!!" I screamed
"What?" Chris asked a little perplexed.
"Nothing, just don't move until I get used to the pain, I will TELL you when I am ready for you to continue." I said a little disgusted, but I could tell by my still dripping cock that I was not turned off by this in the least.
About a minute passed, and I felt that I was ready for him to begin fucking me, and I couldn't wait, because this was what I had been dreaming about for so long. "OK, I'm ready, just go slow." With that, Chris began to slowly move his cock out of my ass. When he got almost all the way out, he slowly pushed it back in. He continued this motion for another minute or so.
"God your so tight, I don't think I have ever felt anything so warm engulf my cock before, this is the best feeling." Chris gasped
"Yeah, I'm in heaven." I breathed out, moaning from his fucking motions. I was really starting to get into this, and I wanted him to continue. "Faster." I moaned, and he answered me by picking up the pace big time, before I knew it we were moving like a well oiled machine, and he was fucking me for all he was worth. After a couple of minutes of this action, he hit a spot, and I thought I was going to explode from the sheer feeling of it, one thrust later he hit that same spot again, and then again. The last time I did explode.
"OH GOD!!!! IM CUMMING!!!!!!!" I exclaimed running out of breath. I shot my load all over the floor, and it was the most I had ever shot in my life up to this point. The contractions of my ass from my orgasm pushed Chris over the edge.
"I'M GONNA CUM!!" he screamed
"CUM IN ME PLEASE, I NEED YOU TO FILL ME UP!!!!!!!!" I exclaimed still out of breath from my orgasm. Chris began cumming, and I thought the first shot was going to go straight through me it had so much force behind it. The rest, I could feel filling my ass up to the point that it was leaking out and oozing down my leg. When his orgasm subsided he collapsed into me breathing really heavily. He slowly exited my ass, and began to clean himself up with some toilet paper off the wall.
"I might just have to keep you around, your one hot little fuck." Chris exclaimed smiling down at me while I was busy cleaning myself up as well.
"Yeah, your hot too. Actually I was wondering if we could see more of each other, you know like a couple or something." I said still feeling the effects of my lingering orgasm.
"What? Are you nuts? I just meant that you would be good to have around when I needed to get off, I ain't no fucking queer, and I don't want to start a "relationship" with you. What are you, some kind of faggot?" Chris looked down with a disgusted look in his eyes.
"Well, I just thought..........." I couldn't get the whole statement out.
"Well, you just thought wrong. I'm outta here pansy ass." Chris said as he stormed out of the bathroom.
I was devestated. I thought for sure that I had found the guy that I could confide in and share what I couldn't share with anyone. I started thinking, as I finished cleaning myself up, that maybe I would never find the right guy, and that I would be alone with my secret forever without anyone to talk to about it. I left the bathroom feeling really depressed. As I made my way to my room, I was thinking about what had just occured in the bathroom. All in all it was a good experience, I mean I had a great time, but it would be a long time before I dared try anything like that again. I couldn't let something like that get around the entire school. I knew Chris wouldn't say anything, because he would have more to lose than me, but I couldn't let that many more people know. As I entered my room, I found my roommate was already asleep. I crawled into bed, and turned off my light, really depressed, I feel asleep.
09-24-1996
I've decided to stop feeling sorry for myself, and start back on my mission. There has been a new development in my life, in the form of a transfer student from Paris, France, his name is Stephen....
********Well, thats the end of the first chapter, or part, of the story. I hope you all enjoyed this entrance. I will try to finish the next chapter soon, but until then please let me know what you think of the story so far. You can email me at GABigflamer22@aol.com. Thanks for all your support.