I like reading about people's first time experiences. Here's mine.
The first time I remember masturbating, other than idly playing with myself while watching Saturday morning cartoons, etc. in my pjs, was on the playground in first grade. I was 6 years old. The playground had these large swing sets, and lots of boys liked to climb the vertical poles to get to the top and hang from the top horizontal pole with their legs wrapped tightly around the vertical pole so they wouldn't slip down. Sometimes they'd hang there like that for five minutes or so with a blank, dreamy expression on their faces. I thought they were showing off that they could climb that far and stay up there, so I decided to try it. I quickly found the real reason, as when I wrapped my legs around the pole, my penis rubbed on the pole, and it felt strangely good. I could feel I got hard down there, and it felt even better.
I did that several times before I let the good feeling get the better of me, and suddenly one day I felt this wonderful throbbing in my penis, and my whole groin area got really sensitive and a great feeling overcame me. I just held on tightly, holding myself against the pole as the throbbing happened, then slid down, feeling very tired.
Well, that was a real revelation to me, and an activity I repeated nearly every day during recess. I don't remember how many other boys did that, but it was a significant number. Ever since then I've seen boys hanging on poles like that ever so often, and it is pretty obvious what they are doing, and I enjoy watching them. What I can't figure out is how the teachers at my school could ignore what the little boys were doing on the swing sets. No one ever said anything about it, but they must have known the pleasure they were giving themselves. I have long wondered if they enjoyed watching us, too, or just decided to leave us to our vices.
Anyway, sometime during second grade I began to realize how obvious it must be what I was doing, and I stopped doing it at school, instead doing it on my own swing set at home. Other boys seemed to have the same reaction, as my classmates stopped doing it in public, but younger kids did it. It seems to have been an age thing; in first grade there were always a few uninhibited boys who discovered the technique, but by sometime in second grade got self conscious enough about it to stop doing it publicly. I didn't know if they did it at home like I did, but I figured they must have.
When I did it at home, I knew my mother could see me if she looked out the window, but it felt so good I didn't care until I got older, and then I'd do it when she wasn't home or sneak out at night and do it in the dark so no one could see me. I eventually graduated to other methods (using my pillow then later my hand), but I remember with great fondness my sessions on the swingset. The funny part is that I almost never used the swings which were, of course, the reason for the poles to be there in the first place. It was almost as though the swings were put there as an excuse to have the pole to masturbate with.