First time is always the best!!
I started masturbating when I was in the fifth grade. While I was at a friend's house playing spin the bottle with Jessica and her brother Eric. Jessica's brother was in the eighth grade I think, I really can't remember for sure. Anyway, when the bottle landed on me Jessica's brother whispered in my ear his dare was for me to jack-off. I had no clue how to do it or what it was. So he said he would show me if I wanted to learn.
So we went to his room and he told me to lie down on his bed. I flopped down and grabbed a pillow and curled it up ready to learn. He sat down on the bed beside me and asked if I had ever had a boner. I really didn't know much about sex I told him. So he started telling me about sex and girls other stuff, he explained how jacking off was simulating having sex with a girl. So by now my curiosity was getting up and so was my little picker, it was as hard as a rock. I wanted to try it, the idea sounded so cool. Something that felt like having sex and you didn't need a girl to do it.
So I timidly unzipped my pants and slipped down my underwear. Eric told me just how I need to hold it since mine was still a bit small. I started working it kind of slow, my fingers kept slipping off but it felt good. I only could do it for a few minutes because the feeling was so new to my little body it hurt. When I stopped, Eric asked me if I had felt it. Once again I didn't know what he was talking about. So he explained to me that the hurting that I was feeling was the start of an orgasm and I needed to do it longer.
I tried to tell him I couldn't as it hurt and my hand was cramping really bad. So he offered to help me out so I could know how it really felt. He started out at a good pace and his hand didn't keep slipping off like mine did (more experience I guess). The feeling started creeping up on me, it was the best thing I had ever known in my life. It flooded over my little body from head to toe, I loved it. My whole body tingled even the inside of my mouth was tingling; with my hair standing on end it was wonderful, I couldn't believe it. So when I came out of his room the first thing I wanted to do was tell Jessica about the cool thing her brother just showed me. But Eric grabbed me and told me that jack off was something that you had to keep secret, you could only do it when you were alone. After that day Eric never touched me again, but sometimes he would smile and ask me if I was having fun with what he had taught me. Which I was, lots of fun!!!