I love the stories of first-time experiences. Here's mine
The first time I can remember noticing how good it felt to stimulate my penis was in second grade. Like most boys, I would get bored of class after a couple of hours, and would fiddle with anything. One day I was fiddling with my pencil, and accidentally started tapping it on my crotch. When I hit my penis, I noticed it felt good, and the inevitable happened: It got hard. It was of course pretty tiny, but it still felt good, and I found that rubbing the pencil up and down on it felt even better. I did that for a while before stopping, and was surprised at how good it felt.
It was probably the next day that I thought to do it again, but this time I noticed I had a small hole in the seam between the legs of my crotch, and I could fit the pencil into it. I found I could then push the pencil up and down on my penis, for more direct stimulation than through my pants. All there was between me and the pencil were my thin underwear. That felt really nice.
Devious as I was, I made sure the next day that my pants had a similar hole. In fact I think I cut the threads so there would be one, and this time I left my underwear at home, so I was naked underneath. My pencil fun was great that day. I did it repeatedly, any time I thought no one could see what I was doing.
Then one day I noticed I had a hole in my right front pocket. That opened up new ideas. At first I put my pencil into my pocket and massaged my penis that way, and it felt really good, but I discovered that I didn't need my pencil. I could put my hand deep into my pocket and slowly work it around until I could grip my penis, and then work my penis into the hole so I was holding the head and upper shaft between my thumb and forefinger. That felt better than the pencil ever did, and I sat there slowly rolling my penis around between my fingers.
That became my secret little hobby every day at school. I don't know how many times I did that before I discovered the ultimate pleasure, but I remember it like it was yesterday. I was slowly rolling my hard little penis with my fingers and it started to feel better and better, and I felt a strange urgency, when all of a sudden, WHAM. My penis swelled and throbbed, and my whole crotch went into spasms and it felt SO SO good. It throbbed like that five or six times, then left me limp, tired, relaxed, flummoxed, you name it. I knew I had discovered something special. And of course that became a daily routine.
The only drawback, at least at first, was that I couldn't carry anything in the pocket of any of my school pants or shorts, because I had made holes in every pair, and things would fall out.
I was caught, though, by one of my friends, who sat beside me. One day after school he made a remark about me playing with myself in school, and I asked what he meant. This was the first time I had ever heard the term 'pocket pool,' as he said, 'You play pocket pool every day.' I admitted it, and he said he did it, too, but not in school. He said he wasn't the only one who saw me do it; several of the boys joked about it. I thought I would die. But that didn't stop me, at least not that year. I did it in third grade, but stopped after that, preferring to do my thing in more privacy.
But the memory is still with me, and its fun to remember those innocent times.