Many of the stories here seem to be submitted by young people or about a time when they were young. This is the latter.
I was ten or eleven when an older cousin introduced me to the world of pornography and masturbation. It was photo's that he had snuck out of his Dad's magazines, just a page here and there so they wouldn't be missed. It was tame by today's standards, but for a kid, it was the best thing ever. He was three years older than me and I looked up to him, so I wanted to do anything he did. I guess we had looked at the pics two or three times before he started to masturbate.
I was stunned, I didn't know what he was doing. I got hard when I looked at the naked girls, but I had never jerked off. Once I saw him do it, I figured if he did it, then I should too. It was an amazing thing to discover that feeling. I didn't ejaculate anything at first but I definately had an orgasm, a few of them actually.
Now, as Paul Harvey would say, the rest of the story... Apparently, our jerk-off sessions were not as private as I had thought. My cousin's older sister (also my cousin of course) was seventeen at the time and she came over about a year and a half after that first session, babysitting my seven-year-old sister and me while our parents went out someplace. Of course at that age, I thought I didn't need a sitter, so she was just there for my sister.
Anyway, after my sister was in bed around 7:30pm my cousin starts asking me if I have a girlfriend, or who I like, stuff like that. Very innocent, but to me, since she was older and I thought very hot, I was getting excited and hard as a rock. What I didn't know was, was that she was trying to do just that, because she knew about me and her brothers 'secret' jerk-off sessions. Once she had my blood flowing almost exclusively to my penis, she asked if I liked to jerk off more or did I like to have someone do it for me.
I almost died of heart failure right then and there. I don't know if my face was redder than the head of my dick at that exact moment, but it had to be close. My response was the classic 'I don't know' and tried not to make eye contact as is usual among embarrassed pre-teens. With that, she reached over to move my hands away from my crotch so the lump that was my hard dick was evident. She gave it a squeeze through my jeans and asked if she could have a look at it. I was happy to oblige, but also a little apprehensive.
She helped me open my pants and slide them down enough to fully expose my dick and balls. It practically snapped out like a spring, all four inches of it. Not bad for my age I guess. Finally, we made eye contact as she looked for the okay to take over and I guess somehow I conveyed the message because she started to rub it up and down. Probably no more than ten strokes and I was shooting cum all over my belly and her hand. It was only the third or fourth time I had actually ejaculated anything, and it was the most and thickest ever. She cleaned it up with some tissues and we talked a little about it before I went to bed. Needless to say, I got off again before going to sleep just thinking about it.
I still see her occasionally, but we live far apart now, 32 years later. We have discussed it, but it was a one time thing that I will always thank her for.