My youthful experiences mirror many described here. My best friend and I would go to my house after school. My parents both worked and mother did not get home till 4:45 giving us about an hour a day alone. We would mess around the way kids do, and that included wrestling around. We both sensed the sexuality of this but for a long time did not acknowledge that we really did it because it felt so good to be touching each other. At about age 13, my friend tore his shirt while we were at it, and after that he would strip to his underwear whenever we got into wrestling, which was just about every day. I would do the same. It made sense for him since it was not his house and he had no other clothes to put on, but I could have just put on old pants. We both accepted the oddness of my not doing so without comment. In our underpants (jockys) we could not hide from each other that we were getting hard every time, and we eventually started to include squeezing each others balls as part of the wrestling, with the goal being to make it hurt. It pretty quickly got to the point where we would put our hands inside the other's shorts to do it, and squeeze not only the balls but also each others' dicks. I never masturbated up to that point and neither had he. I had had night emissions before that, though, so I knew about cum. One day as I had him pinned and was squeezing his balls and very hard dick, he started shaking and stopped struggling completely. I didn't know what happened and thought I hurt him. I stopped squeezing but did not move my hand. Then I felt my hand getting wet. I thought he was peeing for a second but then realized he was doing what happened to me when I had sex dreams (some of my sex dreams involved wrestling with him). He quickly pulled down his underpants and we both watched the thick cum slowly rolling out. It did not shoot just sort of rolled out for a long time.
We both examined it and discussed what happened. He kind of had an idea what it was, but I knew more and my explanation reassured him, as well as hearing that it happened to me when I was asleep. We were both still concerned about not wanting the other to think we had a sexual attraction to them, so our face-saving pretext was that I had squeezed the cum out of him. As soon as we came up with this fantasy, I told him I wanted him to squeeze the cum out of me now. So I pulled off my underpants too, and laid back. He took my balls and now very swollen dick in his hand and squeezed (but not too tight) and let go and squeezed and let go. It felt better and better and I was so aroused by then that I had my first waking orgasm too. Mine shot up in the air a good way, and it was a discovery for both of us, that it would do this.
We instantly developed a daily habit and did this together every chance we got. I had no need to masturbate since I had his hand for that purpose and I did not masturbate myself until more than a year later when we stopped our sessions. Then, as now, one of the images that always went through my head when I was close to coming were our 'wrestling' sessions.
There is just a little more to the story. Two summers ago I walked in and caught my son (14 then) with another boy wrestling in their underwear. I felt bad about walking in because it painfully embarrassed them both, and none of us knew what to say or do next. Red faced and humiliated they grabbed their pants and started to pull them up over their bulging boxers. Finally after a very long silence, I broke the ice and said I was glad they had sense enough not to wrestle in their school clothes. We never talked about the incident again. I hope he will have sweet memories of his youthful experiences as I do.