I read all these stories about how boys learn to masturbate from older brothers, friends, and relatives, but I learned from my younger brother, which is probably unusual.
Most boys seem to learn to masturbate from peers or older friends or relatives. For years I was embarrassed that I learned from my younger brother, but I've gotten over that silliness.
Until our teens, my brother and I shared a room and a large bed. We moved into a bigger house when I was 15, and we got our own rooms, but I never really minded sharing when I was younger.
At age 12, I was totally unaware of what you could do with your penis other than peeing. Of course I knew it was sensitive and felt good to play with it when it got hard, but I never did it long enough to know what it could lead to. I can remember falling asleep with my hand in my jockeys, feeling the pleasant warmth of a well rubbed boner, but not the ultimate feeling.
When I was 12, my brother was 10. He was a little fireplug; a lot more uninhibited than I was. He'd try anything. One night as I was drifting off to sleep, I noticed movement in the bed next to me, and turned over to look. There was my brother with his shorts pulled down, laying with his pillow bunched under his crotch, rubbing up and down. I had no idea what he was doing, so I asked him. He said he was 'getting a good feeling.' Interrupted, he rolled off to look at me, and I noticed his little penis was hard. He said he and Jimmy (his best friend) did this all the time, and it felt really good after a while. He said I should try it, then rolled back onto his pillow and continued.
I watched him with curiosity for a little bit, and got a boner myself, so I decided to try it. I pulled down my shorts and put my pillow down there, and rolled onto it and began rubbing on it. It did feel good, and since my brother seemed to enjoy doing it for an extended period of time, I kept going. I noticed it starting to feel even better, and a feeling like I was going to need to pee started to come. Then my brother sped up, then tensed and held still, panting. Not knowing what was happening, I figured he must be having the good feeling he mentioned, so I kept it up, and all of a sudden I exploded, with the most fantastic throbbing and feeling that radiated from my crotch. I didn't realize it at the time, but I yelled out and scared my brother, who shushed me, saying I'd attract mom and dad.
I just lay there reveling in the feeling, and wondering why I'd never done that before. 'Wasn't that great?' my brother asked, and of course I said yes.
Well, from then on, we both did it side by side every night, and my life of masturbation had begun.
One weekend not long after that I had a friend sleep over. As we always did, the brother without a friend slept on an air mattress on the floor, so my friend and I shared a bed. I remember wondering if he did what my brother and I did, and was soon to find out. My brother started doing it down on his air mattress, and my friend asked what the noise was. I didn't want to admit I did things like that, so just said, 'Oh, that's my brother. He plays with himself a lot.'
My friend answered, 'I didn't think someone that young could do that. Do you?'
I was scared to answer, but said, 'Sometimes.' He came back with, 'So do I, but I do it all the time. Want to now?'
Of course, I was game to do it, so we both stripped off our shorts and went to it. So there were the three of us humping our pillows happily, and a new dimension to my masturbation life had begun.