To start the story off let me describe myself. I'm about 5'7', blue eyes, blond hair, and a little muscular. I go to a high school in Chicago and this involves one of the new freshman who just moved there, his name is Nick (not real name). Nick is about 5'9', with brown hair, brown eyes, and also a little muscular. He just moved this year and joined the cross country team, which I'm on.
Nick was not in any of my classes, but I saw him on the cross country team and thought he was cute. I started to talk to him over the next couple of weeks and couldn't decide if I liked him or not. He was arrogant, but he was also nice and smart. Something that I noticed right away about him was that in the changing room he wore very tight underwear. Whenever we changed my eyes would be glued to the little outline his dick made in those briefs.
After a while, Nick and I became close friends. He came over to my house, and I came over to his. We would chat about things like school, girls, music, and other things like that. Once we became more comfortable around each other our conversation started to turn to things like sex, porn, and masturbation.
The sexual aspect of our relationship started about one month after school started. Nick was over at my house and I pretended to steal some money from his wallet. I shoved the five dollars down my pockets and bated him, 'what are you gonna do?'. He started to chase me until he tackled me to the floor of my basement. We wrestled for a little bit, both of us covered in sweat, when he remembered the money. He reached into my pocket to grab it and felt my hard dick through my jeans. He faltered for a moment, but then he grabbed it. He started to rub my penis through my jeans for about a minute until he decided to just go for it.
Nick took his hand out of my pocket and slowly started to unzip my pants; I was speechless. He pushed my jeans down to my knees and lifted my shirt over my head. My bulge was obvious now, and I decided to take it a little further. I unbuttoned his shirt, button by button, savoring the moment. Then I unzipped his pants and saw the outline of his dick through his tight underwear. It was a little small, but still cute. I took his underwear and his five inches sprang to attention. I ran my fingers through his obviously trimmed pubic hair and gripped his penis. I wasn't used to jacking off something so small but I got used to it. After a couple of minutes of this he took my hand off his dick and took my manhood in his hands. The head of his penis was red and leaking pre cum, but now it was my turn.
Nick got in between my legs and started masturbating me with both hands. He did this for about five minutes until I told him I was going to cum. 'Wait.' He said. Nick pushed my chest down on the carpet and wrapped his legs around mine. Our penises were touching now and he started to rub up against me. The feeling was incredible with out pre cum mixing and the thrill of the possibility of being caught. He kept humping me a little faster each time until he exploded onto my stomach. This immediately set me off and I came the most I've ever cum in my life.
We cleaned up with his underpants and I asked when we could do this again. He simply replied with, 'Come over to my house tomorrow.'