The first time I fooled around with another boy was in second grade, so I would have been seven or eight. My best friend was named Craig, and we played together a lot. We had frequent sleepovers, mostly at his house since I had a live-in grandmother who was crotchety and was annoyed by the racket made by two young boys.
One cold fall night we got ready for bed, which meant stripping down to our underwear. The room was cold, but Craig had an idea. The heating vent was right next to his bed, and he pulled the covers over so they kind of made a tent over the vent, and the warm air billowed into the tent. For some reason, Craig pulled off his underwear and got naked, and I followed suit.
We had played 'pull down pants' games before, which is common among young boys, so it wasn't any real revelation or anything. But it felt really good to be naked under the covers with the warm air blowing over us. We were pressed together under there since there wasn't much room, and we started a kind of slow motion wrestling, accompanied by running our hands all over each other. I don't know how this game started, but it was fun to be feeling each other up, and of course it wasn't long before we were fondling each others' genitals, which felt great. We both got little boners, which we rubbed all over each other. We must have rubbed around on each other for over an hour before we got sleepy and just dozed off. When we woke up in the morning still naked, we did it some more until his mother called us to breakfast.
We did that on several occasions, and I really enjoyed the body to body contact. It wasn't anything overtly sexual, but it felt good and was fun. I looked forward to it.
Then one day I was at his house on a Saturday afternoon. His mother announced she was going to the store, and was leaving Craig's older sister, who was around 12, in charge. Well, his sister always totally ignored us, and we knew she wouldn't pay any attention to what we were doing, so as soon as his mother drove off, Craig and I rushed up to his room, closed and locked the door, crawled under the covers, and got naked. We wrestled and fondled and rubbed our little boners on each other, and it was great. Then all of a sudden I found myself laying on top of Craig. He was on his stomach, and my boner slipped into his butt crack. Boy, did that feel good. I rubbed it up and down his crack. He said it felt good when I did that, and it certainly felt good to me, and I kept it up. I guess it was instinct, but I found myself humping his butt crack harder and harder, and I started to get an intense feeling, then it hit me: My first orgasm. I had no idea what was happening, but I loved the warm throbbing and tickling feeling I got as my little penis jerked in his butt crack. I suddenly felt really tired and relaxed, and told him he should try that. We reversed positions, and he started humping me, and he had been right -- it did feel good to have his boner rubbing up and down my crack. After a few minutes I could feel him stiffen and he held still, pushing hard, and I could feel little jerking movements. Then he relaxed and rolled off of me, and we both lay there panting.
That was the end of that session, but I knew we'd do that again. And in fact we did, many times. Our butt humping became a staple; always the end of our bedtime games.
Both of us joined Boy Scouts when we turned 11, and of course tented with each other on campouts. We both had the same kind of sleeping bag, so after lights out we'd quietly open them up, zip them together, and have one big, double bag. We'd get naked and wrestle until we got to our favorite part, and hump each other to a dry orgasm.
We did that together for several years, only stopping when we hit puberty and things got messy. But we transitioned to jacking off together, which also was fun.