The first I can remember receiving pleasure from touching myself was when I was a young boy, probably around age 5 or so. Saturday and Sunday mornings were always quiet around the house, as the older people recuperated from the week, and I was allowed to lounge around in my PJs and watch cartoons in the den. Usually I was alone, and I can remember idly playing with my penis with my hand down in my pants. Unlike many of my friends who wore underwear under their PJs (a habit I could never figure out), I was loose and free, and I can remember that it felt good after being constricted in tight underwear all week. (Boys all wore "tighty whities" when I was a kid; boxers were for old men. The only time I ever saw a boy wearing boxers was in the changing room at the pool, and everyone stared at him. Turns out he had a bad rash in his crotch and the doctor told his mother to get him boxers until it went away.)
I would lie on my side on the couch and watch cartoons, and just play with myself for long periods of time. I don't know what age I first got erections while doing that, but it was also pretty early — perhaps I always did. My recollection was always that I was stiff when doing it, and I realized it felt better that way. Mostly I would hold my penis between my thumb and forefinger and gently roll the head around, which felt really good. Once in a while I would stroke up and down on my penis, which also felt good, but not as good as rolling the head.
I have read that many people, including some "experts," don't believe very young children can experience orgasm — that it happens only at puberty. But I can say with absolute certainty that such is not the case, as I had frequent, and excellent, orgasms from a young age. When I was 7 (I remember the age because it corresponded with the death of my friend's mother), I was doing my thing, and it kept feeling better and better, so I kept rubbing my penis more and more, and I had my first orgasm. Of course I didn't know what it was, but I did know it felt really good, and I knew I wanted to do it again. I was kind of afraid, since I didn't know what happened, and my penis felt a little sore and I felt tired for a little while. But the next day I did it again to see if it really was as good as I remembered, and it was even better, since I was looking forward to it.
Of course I was hooked on doing that whenever I could. I called it "my good feeling." On some mornings I'd do it two or three times. I also discovered that I could get the same feeling by putting a cushion from the couch under my crotch and humping it, and that felt good. The problem was that I had a brother two years older, and though he didn't like to watch cartoons in the morning like I did, he would wander in once in a while, so I had to keep a good lookout if I was humping the cushion because I didn't want him to see me. But it was much easier to pull my hand out of my pants if I was doing it that way.
So for years I did that, and would play with my penis almost the whole time I was watching cartoons, which was 3 or 4 hours until my mother chased me out to play. Nobody in my family ever did or said anything to lead me to believe there was anything wrong with playing with myself, but I somehow knew it was something to be done in private, and I didn't want anyone to see me doing it. I wasn't hung up or anything; I just knew it felt good and that if it felt good, there was nothing wrong with doing it, at least in private.
I can also remember in first and second grade doing that in my seat during school. My teachers rotated kids around to see who might have vision or attention problems and therefore should sit in the front. I had good eyesight, so frequently I sat in the back. One day I was sitting there bored while the teacher read a story, and I put my hand in my lap. I could feel my penis, and I began to wish it were Saturday so I could rub myself. Thinking about it, I got a little boner in there, and I rubbed it gently through the fabric. It felt good, so I put my hand in my pocket and was able to grip it and rub it, and after a while I got my "good feeling." The feeling was so powerful and good that I felt lightheaded and felt like I was going to faint.
I didn't do that often, but I enjoyed it when I did. That habit kicked itself when one day my second grade teacher asked me to stay in the room a minute when it was time for everyone to go to the playground. She told me it wasn't good to play with myself in public, and to please not do that again. She said she'd seen me doing it two times that week (I'd done it three!). I was really embarrassed and said I wouldn't do it again. I didn't, and she never said anything else about it. I was afraid she'd tell my mother, but as far as I know, she didn't.
Sometimes on weekends I stayed over at a friend's house for a sleepover, and one morning when I was about 9, we were watching cartoons and I noticed he had put a pillow in his crotch. I could see his arm on the other side from me slide into his crotch under the pillow and make slight movements, and I could tell he was doing the same thing I always did. So I got a pillow and did the same, and we sat side by side on the couch playing with ourselves, pretending we didn't notice each other doing it. The difference was that my friend was more obvious when he had an orgasm. Though I was careful to not make any noise or outward sign (I think someone looking at me would never have noticed), he hunched down over his pillow and tensed, and let out a soft combination of a groan and an "ahhh." It was pretty obvious what had happened.
We had more frequent sleepovers after that first time, and we'd masturbate side by side. We didn't do it openly until several years later.
I had a hard time masturbating in bed at night. I wanted to, but I still shared a room with my brother. But by the time I was 11 he was in middle school and had to get up earlier than me, so I had a little time alone in bed in the morning during the week, and I would do it then. I longed for the weekend when I could do it for a long time, but a quick "good feeling" was better than nothing, so I did it nearly every morning before getting up for school.
My situation changed one night when I was having trouble sleeping. I had been sick and had slept all day, but I was over it and wasn't tired at all. Trying not to disturb my brother, I just lay there quietly. I usually fell asleep almost immediately after I got into bed, and I guess my brother was used to that, so shortly after I got into bed I heard some rustling, and out of the corner of my eye I could see him pull the sheet down on his side, slide his underwear down, and hold his erect penis. He was 13 at this point, and a lot bigger then I was, but not fully developed. I don't think he had pubic hair at this point. Anyway, I was surprised to see him start to stroke his penis, and I realized he was doing what I did, which was a revelation to me. I thought my friend and I were the only ones who did it. And this was the first time I'd seen my brother, or anyone else for that matter, with an erection.
My brother went to it for a while, probably 5 minutes, and I saw him tense like my friend did, and then several jets of white stuff came shooting out of his penis, landing on his stomach. By now my brother was lying perfectly still, holding his penis, concentrating. After a minute he reached for a tissue on his bedside table and cleaned up, and then he pulled up his underwear and went to sleep. I was really excited by what I had seen. I don't know how I knew, but I had a feeling what the white stuff was, and I was jealous that my brother had it and I didn't.
The next morning after he got up I went looking for the tissue, and it was in the trash can, along with a lot of others. I realized then he probably masturbated every night, and I never knew. That excited me, and I did it to myself before getting ready for school.
From that day on I tried to watch my brother masturbate at night whenever I could stay awake. He did it almost every night. I felt a little guilty watching him like that, but it was fascinating and exciting. I began wanting him to see me doing it, but I didn't know how to do that since I was afraid.
My chance came one day when I was about 12. My brother didn't have to go to school that day for some reason (doctor appointment?) and I wanted to do my usual morning "good feeling" before getting up from school. My brother was asleep, so I decided to start and figured that if he woke up and saw me, it would be okay. So I gently pulled the sheet down and opened my PJ bottoms and went to it, just like he did. It didn't take long for my brother to wake up, and I could tell he was watching me. It was strangely exciting having an audience, and it felt really good. It was still a dry orgasm, but I remember it being very intense.
When I was done my brother said, "I didn't know you did that." I told him I'd been doing it for years. He said, "Me too." I told him I knew, that I had seen him do it at night. I was afraid he'd be mad, but he wasn't, and laughed. "Now we don't have to hide it, since we both do it." So that night we lay side by side and masturbated, and I felt closer to my brother than I had ever felt before. Over a period of a couple of weeks we graduated to masturbating each other, and that was a lot of fun. In fact I began ejaculating around this time.
I began thinking of doing it with Billy, the friend who did it under the pillow while we pretended to watch cartoons. I was afraid to try anything with him, until the day we had sex education class at school. Unlike all the stories I have heard about content-free sex-ed classes, the teacher who taught the boys' class was surprisingly open about it and explained a lot. I was especially interested in his discussion of masturbation. He didn't go into much detail, but he did say that almost all boys our age did it, and it was nothing to be ashamed of. I noticed a lot of snickering around the room, and I looked around and saw a lot of knowing smiles, and a couple of guys giving the universal hand signal for masturbation, which wasn't hard to figure out. I suddenly realized they all did it, too. I looked at Billy, and he gave me a sheepish smile, and I did the same to him.
The one thing the teacher said that really got my attention was when he mentioned that many boys do it together, and that it didn't mean they were gay or anything; it was just mutual exploration. I looked at Billy again, and he returned my glance, and I knew something was going to happen.
So the next time we had a sleepover (I don't remember which house we were at, but if it was at my house it was in the extra bed downstairs, since there wasn't enough room in my room with my brother there) we were talking, and I put my hand in my PJs and played with myself. He did, too, and pretty soon we were both openly masturbating. Like with my brother, we soon began doing it to each other, and had a great time. That turned into our favorite pastime after school and on sleepovers.
We developed a routine. As soon as we got into bed, we'd both strip naked and we'd talk for a while. Billy liked to be masturbated first, which was nice, since I found it exciting to do it to him, so I liked to have him do it to me after I finished him off. I'd usually sit cross legged next to him and masturbate him long and slow. I never tired of watching his reaction as his breathing changed and his stomach tensed as he approached orgasm. I liked to feel the throbs in his penis. I never noticed when I did it to myself, but doing it to him, I could pay more attention. I would always feel one sharp pulse, which was my signal to hold my hand tightly on his penis but not move, then several rapid pulses. By the third the semen would start coming out. I often took my free hand and held it under his testicles, so I could feel the pulses in the root of his penis. I don't know exactly where the muscle is that ejects the semen, but it feels even stronger down there, so it must be close. Unlike me, who shot onto my stomach and sometimes onto my chest, his just seemed to dribble out and run down my hand, but I didn't mind it. His pulses always seemed much stronger than mine did, which made me wonder why he didn't "shoot" — but the important thing was that I could tell he always enjoyed it.
Then he would masturbate me the same way, though he usually sat between my legs and did me from there. Billy's hand was always so gentle but firm, and he knew just how to avoid contact with the head of my penis when it was the most sensitive while I was ejaculating. Just a little touch there at that time was almost painful. He seldom got my semen on his hand, since I usually shot clear.
