I have never masturbated with somebody but I thought it may happen and here is why. For a long time like three years I think, a few times a week I would hang out with this friend of mine Karl who was almost 14 at the time, as tall as me and we weighed the same. We always started goofing and wrestling after a while together and I got at least a little bit of a boner from it.
Sometimes I was real hard when I got my legs wrapped around him. I thought he liked it the same way too but we never talked until this thing happened.
We were wearing our jeans or sweats and so I could only tell he was liking it because sometimes I could feel him hard when we got wrapped in a tight hold. But this time he was on top of me and I was about pinned facing him and he was sitting on my waist and holding my arms back and I saw his arms were trembling real hard and he just stayed that way holding me and got a weird look in his face and sort of teared up and then his hips started pushing at me for a few seconds and he just let go and stood up and was running to the bathroom saying he thought he wet himself.
We never talked about masturbation before and I just always thought he did it same as me which is at least once or twice every day. But it turned out he didn't know much about it and never did it all the way and what happened is that he cummed in his pants from rubbing on me. He didn't understand what was happening but I knew right away. I said he should take off his underpants because there would be gooey white stuff all over them. He did that and brought them out and sure enough they were soaked with cum.
I told him about masturbation and that I make that stuff come out every day. He acted like he knew all about masturbation but he asked me some questions about how I did it and finally told me he never did it except he played with himself sometimes but not long enough and never had the orgasm. I knew a lot about it from Solo Touch and from my older brother and I told him I didn't mind that he cummed from pressing on me.
We got together once after that but couldn't wrestle because his sister was around. I was really excited and all the time now I was thinking about the next time because I thought it was going to be so good. I get hard just thinking about it now.