I enjoy the stories about how guys learn to masturbate, so here's mine. This happened four years ago.
When I was 11, I joined Boy Scouts. I knew nothing about sex or masturbation, other than I knew it felt good to play with my penis in bed at night, especially when it got hard, but I had never done it long enough to orgasm.
When summer camp came, our troop went off for two weeks, and I was to learn a lot more than knot tying! I was assigned to a tent with a boy I'd known for several years, but we didn't know each other well; only in passing in school. The first thing I noticed was that he had no inhibitions about being naked in my presence when we changed clothes, etc., in the tent. And the first night I was surprised when he climbed into his bunk naked. I always slept in my underwear.
We talked for a few minutes before the scoutmaster yelled that it was time for lights out, and we weren't supposed to talk any more. It was a warm night, so my tentmate and I were laying on top of our covers, and there was enough light for me to see that he was idly fingering his penis while laying on his side. He got a little boner, and I did, too, while watching him.
Then he said quietly, 'I have to do something.' He pulled his pillow down to the level of his crotch, made a crease in it with his hand, and lay on top of it with his penis in the crack. Then he started humping it slowly.
Stupid me, I had no idea what he was doing, but he had his face turned toward me with his eyes closed, and the look of concentration on his face made it obvious that he was enjoying what he was doing. He kept it up for five or ten minutes, getting more insistent, until he stiffened and stopped, holding his penis hard into the pillow. His mouth jerked open as though he was yelling, and he started to pant. He moved his butt up and down just a little.
He lay there like that for a minute, then rolled off the pillow. His penis looked red and sensitive, and he just said, 'boy, that felt good.' Then he pulled his sheet up and just went to sleep.
The next morning, he did the same thing, much to my surprise. I again watched, and was fascinated, confused, and curious about why he was doing it. That night I finally asked, and he said, 'Because it feels good. You should try it.' I thought about it for a few minutes, while he began his ritual, and decided what the heck, I'll give it a try. So I did. I pulled my underwear off and mounted my pillow, and began rubbing on it. And it did feel good. It took a little while for the feeling to build up, but I could tell something was coming, and then it hit me: A strong throbbing in my groin, and the best feeling I'd ever felt overcame me. I was shaking in pleasure. My penis got suddenly very sensitive, and I had to pull off the pillow, but it felt too good to let the pressure off, so I gripped it in my hand as the throbbing continued.
I must have looked surprised, because my friend was smiling at me as though I looked really silly, which of course I did. I also felt really tired, so after I caught my breath, I just pulled my sheet up like he did, and fell asleep naked.
Well, I was hooked. He and I did that every night and every morning after that, and after camp we stayed close friends, going to each others' houses all the time and having sleepovers. We took every opportunity we could find to hump our pillows together, and became experts at after-school quickies up in his bedroom.
There is another aspect of this story involving his older brother (who was 13 when we were 11), which I'll recount in a future post. Suffice it to say that it was his brother who taught him this wonderful trick.