I sent in my story of how I first discovered masturbation as a young boy (called Commando Adventures), and it was so fun to see my own story posted, I thought I should post more. All true adventures of mine.
This one is about the first time I masturbated with another guy, my next door neighbor named Rusty. It was when I was 12 and he was 13. We often camped out in the yard on warm summer nights. Nothing of a sexual nature had ever happened before; in fact I had stopped masturbating for a year or two (in my earlier story I told about how I humped the bed, etc.). I don't know why -- I just seemed to lose interest for some reason.
Anyway, this night Rusty seemed horny. He got talking about dicks and stuff, and I got a boner at the racy nature of the conversation. Then out of the blue Rusty asked me if he could show me what he did with his pillow. Certain that it involved sex in some way, I said OK, and he pulled off his underwear and mounted his pillow, humping it. I recognized it as the same thing I used to do, and was immediately interested, since I didn't know other boys did that. I also noticed that his penis was bigger than mine, and had just a little hair above it. Then he asked if he could do it on me. I said yes, so he told me to take off my underwear and lay on my stomach. I did, and he mounted me, with his knees on either side of my legs as he lowered himself onto my back, carefully positioning his penis in my butt crack. Then he started humping me slowly, and I was surprised at how good it felt.
He did that for a while, then said I should try it on him, so we changed places. Boy, it felt neat to have my penis in his butt crack, and I went to it.
Before I got to orgasm (I could feel it coming) Rusty said we should change places again. So we did, and he went back to work. He seemed to be concentrating more this time, and I could feel him breathing hard. After a while he became very tense, then stopped, and I could feel his penis twitching in my crack, and could feel a warm wetness. He scrunched forward a little and put his penis into the wet area and rubbed back and forth in it. I vaguely knew what it was, so wasn't too surprised. I didn't realize until later that the lubrication of his own semen made his penis feel even better.
Then we switched places again and I started humping him in earnest. It didn't take long for me to come, and it was the strongest orgasm I'd had until that time. It just wiped me out. Afterwards I lay on top of him for a long time catching my breath.
I don't remember the conversation afterwards, but we agreed that felt really good. I felt kinda funny about it, like it was wrong or something, but somehow I knew we would do that again. And we did. Over the next 2 or 3 years we did it every time we had a chance. We never tried penetration, probably only because neither of us thought of it at the time. If we had, I'm sure we would have done it.
Those experiences are still very memorable to me.