True Story:

I had this friend who was 4 years younger than me. I met him through mutual friends when i was a senior in High School (17yo) and he was a freshman (14yo). He has a very boyish look to him, even to this day. Big eyes, lips and since he skated alot he had a toned body. Oh and a cute bubble-butt. One day we all went to a friends house to go swimming. There were about 5-6 of us and we decided to change into shorts. We did this in the same room in front of each other. I couldn't pass up the opportunity to catch a glimpse of what was under his pants (boxers or briefs?). It turned out that he has a pair of white cotton briefs on. He was very comfortable in his simi-nude state. This gave me ample time to take in the site. He filled in his briefs very nicely, both the back and the front. I could see that he was well-endowed.

Well, from that day on I developed several fetishes: Briefs/underwear, voyeurism and a crush and this boy ;) Some time later we all went to the theater to watch the movie Baseketball. There was the scene where they show the hunky guys in speedos. Since I was sitting next to the object of my obsession I decided to slowly work my hand over to his leg. At first it was subtle enough to where it was possible that I might have misplaced my hand. As the movie progressed though I became more brazen to the point of almost cupping his crotch. Being the straight guy he was he quickly brushed my hand away. After the movie he didn't say anything. Partly because of this my fantasies of him in his underwear became stronger as the years went by.

Fast forward 4 years and I hadn't done much with my life. One failed attempt at a Technical school had got me nothing but dead-end jobs locally. Now it was his turn to venture out into the world. He decided to go to another (accredited) school. I expressed interest and had him put me into contact with the recruiter. One month later, him, me and 3 other guys that we had met through the housing program were all sharing a 2-bedroom apartment while attending the same school. Logically, me and my friend shared one room and the others shared the second room. Mind you, We left in such short notice that we had little furniture. In fact, my friend and I slept on the floor together. Well, technically we had different blankets but still, we were pretty close.

To my discontent my friend had changed from being a brief man to a boxer man. This I found out by once again how comfortable he was with his body. Often he would come out of the shower with nothing but his boxers on. A very defined bulge in his crotch roused my curiosity to the point of madness. One night while we were settling down for bed I decided that I wanted to touch his dick and see how big he really was. It took me a while but luckily for me he was a deep sleeper. I pretended to roll over ever so slowly just in case he thought my motions were intentional. I managed to get a hand on his thigh. The thrill of my accomplishment had my heart pumping, to all the important places if you know what I mean. Before I knew it I was cupping his cock and balls in my had. While still flacid, I could tell that he was gifted with a big member. His balls also pretty big and just the right amount of loose. It didn't take long before his dick started pulsing to the point of arousal. The whole ordial to this point took some 20-30mins. The whole time I had a strange excitement coupled with a fear of getting caught. As his dick began to grow I reveled in the thought of my best friends cock expanding in my hand just underneath the thin material of his boxers. The boxers were barely enough to contain his massive cock. He got so hard that his cock poked out of the opening in his boxers. It was too dark to see but I finally felt the full extent of his girth. He was uncut like me.

It must've been 7 to 7.5" big, and thick too. Thicker in the middle than at the base or nearer to the head. I slowly began to stroke it. stopping at any sign of him waking up. The more I stroked it seemed, the harder he got. At the same time I was stroking my own dick. I knew for sure that If I made him come, he would wake up. So I made the decision, as if I had a choice, to come before he came. That night was the best orgasm I had ever had. I wouldn't dare risking putting his dick back into his boxers so instead I left him just like that. Part of me wondered if he would suspect anything when he woke up with his dick outside of the boxer slit, part of me wanted him to know.

To be continued...