I'm the most sexual person of all my friends. Whenever a joke is made in a movie or on TV about masturbation, everyone looks at me and laughs. I even got the nickname 'Tad', (twice-a-day), from them. None of them are as open about it as I am. None, except for maybe Tom.
Tom and I have been friends more or less since fifth grade (we just graduated high school). I was the first to go through puberty of all my friends, and I also believe I was the first to discover masturbation. I actually learned it while watching cinemax when I was nine. I saw two lesbians together, and I kid you not, my reaction was, 'If they can use their fingers and pretend like they are penises, I wonder if I can pretend my hand is a vagina.'
I did and it was great. I told my same age step-brother about it, but we never did anything together. From the very beginning, I've been very curious about the male body. I always tried to catch peeks at mens penises in both porn and not porn movies, as well as showers in real life.
Once on a band trip, I finally let my friends know about my addiction to masturbation. We were in eigth grade, and I was rooming with Tom and whom I consider my best friend Bradley. I managed to convince them both to show their dicks with me. Bradley was uncut, unlike me. Tom, who is jewish, was more like me, in that he was cut, but as it turned out hadn't entered into puberty at all. The next night we watched a pornesque documentary on HBO and I jacked off under the covers. Bradley did too, but he didn't finish. Tom couldn't, he had never done it before and couldn't even get hard.
Years later, I was traveling in France and Spain. Most of the time we had three or four people in the room, but whenever it was just two, it was me and Tom. By now, Tom was the tallest person in the class, if not the entire school, and his penis had changed a lot from that small two incher. We would walk around in the nude freely in the room, even opting to sleep that way. We would also jack off under the covers. The second night, I told him, 'You know, if you ever wanted to, I would jack you off.' He seemed disgusted and treated me like I was gay, even though I assured him that plenty of straight guys did it together (because I had this wonderful website as proof). So I shrugged it off and went to sleep.
Later, on the last day there, we had just finished a quicky in the room when he came over and pushed down on a pillow I was using to hide myself while I came down from the orgasmic high. He rubbed it for a second and I said it felt good, so he did it some more. Then I tried it on him. The pillow was thin, and I could wrap my hand most of the way around his shaft through the pillow. He said we should try it with just the pillow case, so I took the pillow out. He tried to do it to me for a little bit, and I loved it, but he wanted me to try him. He said, 'You know, I don't want to touch you, but if you don't have a problem with it, you don't have to use the case.' So I threw it on my bed and went to work on him. It was amazing. Here I was stroking my friend's sixteen-year-old cock. It wasn't the first time I had held someone else's member, but it was the first time I did it to a close friend (and with the lights on). It was slightly bigger than mine just short of six inches, coming in at six and a half. He also had the biggest balls I have ever seen.
I stroked him for a long time, but he wouldn't let me get near him in any other way, so I couldn't get close enough to get good leverage. He also didn't make any noise or facial expressions like I do. He just covered his eyes with his arm and lay there. After a while, he said I was doing it wrong, and took over, finishing himself off. I should have had him do me before finishing himself off, because he lost interest, and when he tried me (with the pillow case) he didn't put any effort into it and it actually hurt, because of the fabric.
He decided I couldn't be gay because I was bad at it, and we laughed off the awkwardness of the situation. I now know that I should have used lube on him, but at that point, I hadn't ever used it. That wasn't the last of our experiences together. We remain friends to this day. I'll write about other experiences later. Others have much better endings, but that was the first.