This is my first masturbation experience with another guy. I loved it, and masturbation became a big part of my life after that. I always had the urge to watch other guys, but it wasn't fulfilled with my friend.
My story begins when I was nine or ten years old. By that age, I'd discovered and enjoyed my erections, and even had some orgasmic spasms (although I didn't know what or why or exactly how they occurred). I had a friend, Billy, and we did lots of things together-Boy Scouts and baseball, and hiking and also we built a fort in his basement, and went to school together every morning. Sometimes I'd sleep over at Billy's house, he had twin beds in his room. One evening, after dinner when we were alone in his room, he asked if I'd ever jerked off. I must have said something like, 'What's that?', because I remember that I really didn't know anything about it and I remember what followed was a detailed explanation of how to masturbate. Billy had been playing with himself for about six months, and wanted to tell me about it.
I listened and took his word for lots of things, like cum and climaxing. I was excited and I'm sure I got a boner pretty quick. He had a jar of Vaseline and he took a gob and gave it to me. I greased up, and tried out what he said. I remember two things-the sound of him rapidly stroking himself, and how good my own boner felt in my hand. Before then, I'd played with myself in the shower, kind of haphazardly, but nothing like this!!! I don't remember having an orgasim, in fact, I remember lying to Billy when he asked, and then much later, after more stroking, having my first full-on intentional orgasm, but being afraid to say it finally happened, because it would show my lie. (I didn't know you could do it more than once).
After that first night, Billy and I masturbated together whenever I stayed overnight, and sometimes after school, and we began to collect magazines (stolen from the local newsstands) and pour over them with flashlights under our sheets. I loved to look at my erection while I flipped through the pictures of gorgeous breasts and luscious lips. Billy did the same, and then I'd hear him stroking himself and see his knees go up under the sheets, but he always hid himself from me.
I'd seen Billy's privates a few times. Once when we changed for swimming, and a couple of times when he went to the bathroom. Once, he had a boner when he came back to his bed. I would also be sure to catch a glimpse when he changed his underwear, so I knew what he looked like, and whenever I listened to him, I would imagine his little balls and penis hot and stiff.
I really wanted to show him myself, but I was afraid. The most I could do would be to walk through the room to the bathroom, with my penis standing stiff, and hope that he was glancing and seeing me. A couple of times I did see him clearly with a hard-on, once when he jumped up to close the window shade, and one time in the 'secret chamber' of our fort. He was in there, naked, jerking off and didn't know that his mom had let me in. I saw him with his legs spread, full-on and I stayed and spied on him. Waves of thrilling heat coursed through me while I watched, and then for the first time I saw little beads of cum on the head of his penis (I didn't have any).
I knew I had to back out and pretend I was just arriving. And then I jacked off like we often did in the fort, by rubbing our pricks inside our pants. We were jacking together very often, and I know that we were doin' it together-lots of times we'd cum within seconds of each other-but Billy would never come out from under the covers. I also wanted to expose myself, and one night I said I was too hot, and pushed down the covers. Billy glanced at me, but he acted just like he always did, and never said anything. I wanted to see Billy's privates really badly, but Billy was the leader, and I knew I couldn't suggest it.