From the first I can remember, I always had erections, and always enjoyed pulling and playing with my penis. I learned to be careful about such activity, though. My parents were strict Catholics and scolded us severely whenever they would catch me, or my brothers touching ourselves. Still I remember many languid evenings, just before going to bed when I would stroke and pull my little cock until I finally fell asleep.
When I was in first grade, we lived next to a family that had a pretty red-haired girl about my age. Her name was Joanne, and we became friends. One summer day we decided that we would play 'Show and Tell', specifically 'you can watch me pee and I'll watch you.' We carefully went into the basement, which was little more than a crawlspace. The only light was from the louvered vents in the concrete block foundation walls. As soon as we decided we were safe, Joanne raised her dress and removed her panties, and I followed suit by dropping my pants and briefs to expose my little dick, which hardened immediately. We were squatting in front of each other, and I was looking at a naked pussy for the first time in my life. (I had seen my mother's bush through her nightgown a few times, but now that I was getting older, she noticed that I was noticing and was more careful how she dressed in front of me.) Joanne's pussy was pink and smooth, with nothing but a dimpled cleft in front forming a deep slit that ran between her legs. I couldn't figure out where her parts were. Then an amazing thing happened. A stream of golden urine jetted from that slit to puddle up between our feet! When she was finally finished she smiled and said it was my turn now. I tried and tried, but my little penis was standing up as hard as it could be, making it impossible for me to urinate. No matter how hard I strained, I couldn't make any water. Finally, Joanne got mad, slapped my penis, and left, saying I wasn't fair. We never attempted it again and didn't play together so much after that.
My brothers and I were latchkey kids but with three brothers and their friends around all the time, there wasn't much privacy. But one afternoon when I was about eleven, I found myself home all by myself and took this opportunity to explore my penis some more. The guys in school were talking about sex and doing It and stuff, and I didn't know what doing It was. I was in a Catholic school, so the talk was probably more restrained than in a normal school, and since I hung out mostly with the girls I never got any details, but I very much wanted to find out what It was.
My parents had given me the birds-and-bees-and-sperm-and-eggs-and-nocturnal-emission talk already and told me I could talk to them about sex if I needed to (like this would ever happen). This had given me some idea of what to look for: arousal, stimulation, climax and emission. So I was home alone and eager to experiment. I removed my pants and lay back on the bed and soon had pulled up a great hard-on. I kept rubbing and pinching and squeezing my penis all over. I spread the little hole and looked inside myself, until this became uncomfortable. I began stroking the underside of my little shaft, which I always liked. Soon I was using the fingertips of both hands to stroke the underside of my penis, from the head to my balls. This was feeling better and better. I found that the harder and faster I stroked, the better it felt, and before long, I placed both of my thumbs along the top of my penis to help increase the pressure, and pulling the loose skin up and down the shaft. This was even better! So there I lay with three fingers from each hand rubbing along under my penis on either side of the ridge formed by my urethra, and my thumb tips together and rubbing in unison along the top of the shaft. It felt great, and soon I was really stroking hard and fast. Soon some very new feelings began occurring; a strange pressure from my balls and somewhere near my bladder, as well as an urgent feeling that I couldn't quit now. Before long, I experienced a shattering explosion of pleasure that convulsed my whole body and made my penis twitch and jump like it had a life of its own. As my penis slowly went soft, and I recovered from the waves of my first orgasm I realized two things: there was no sperm like my parents had talked about, and my dick was sore. Still, I was elated. I had discovered what it was, and this revelation changed my life. From that moment on I couldn't stop. I rubbed myself off every chance I got. Soon my dick had a semi-permanent abrasion soreness under the shaft along both side where my fingertips worked. I still continued to use my two handed method, though since it was all I knew. I discovered that if I moved my thumbs atop my penis in the opposite direction of my fingertips while I stroked, created different, very enjoyable sensations before I came. I also tried using one hand or just a few fingers but I always reverted to my two hand method as my climax approached to make sure I got the good result.
Masturbation also changed my outlook on religion. I was the oldest son of a very Catholic family, and it was expected that I would go into the priesthood. I was fine with this, and began studying Latin, doing the altar boy thing and generally trying to be 'pious'. Then all of a sudden I had to start confessing to the parish priest that I was 'abusing myself' two, three, or four times a day, which was very embarrassing. I also didn't understand the whole 'abusing' thing. What I was doing was more like worshipping myself. I didn't see how it hurt anyone so why was it a sin? And if masturbation was so good, real sex had to be phenomenal. How could I give up on this possibility to live the celibate life of a priest? So for the first time in my life I began questioning the teachings of my parents and the church and rejecting the culture of guilt they supported.
Although I was very pleased with my masturbatory experiences, I was very secretive about doing it. I often suffered the pangs of guilt afterwards because I knew I would have to confess another sin. I would sometimes try to stop, but after a day or two of abstinence, I felt the pressure to cum more than ever, and always succumbed, with great relish, to the temptation. I also continued to be troubled by the raw places on the underside of my penis, which was often sore afterwards.
Then I learned a new way to do it. One day on a scout camping trip we were getting everything ready to turn in and Luther, one of the boys in my patrol commented that he couldn't wait to get into his tent, and with the comment he made a pumping gesture with his circled fingers. I new immediately the significance of the gesture, although the circle his hand formed seemed odd. Luther also asked if I wanted to be his bunkmate. Since I was the patrol leader, I had the choice of whom I camped with. I declined his invitation, being too nervous to acknowledge any masturbatory interest. Beside all the guys said that Luther was homo, although this was a common charge leveled at everyone in sixth grade. So I shared a tent with my brother.
Once I was in my sleeping bag, and I knew my brother was asleep, I began my evening ritual of pulling my cock into an erection. Often it was hard even before I touched it, and never took more than one or two pulls to make it stand up. I wanted to try the one-handed method, and so I caressed myself gently to maintain my erection until I was sure that my brother was asleep. Then I gripped my penis in the classic fist grip and began stroking with the same rhythm and pressure that I was used to. This was ok! I didn't know why I hadn't tried it before. As I did this, I tried varying the stroke, pulling over the circumcised head (didn't like this...too sensitive) wiggling my fingers a bit in a rippling fashion (niiice!) and even twisting a little as I stroked (interesting, but straight was better). I finally settled into a preferred pressure and stroke and before long the now familiar sensation of orgasm rolled through my body. I was excited to learn that there was more than one way to make the orgasm (although I didn't know that was what it was called.) I was also pleased to note that my dick was not as sore afterward, and this quickly became my preferred method. About a year after this, I had my first wet orgasm. I can't say I noticed much of a change in the intensity of the experience, but it certainly changed the dynamics. Now I had to be aware of the potential for making a mess in my pants or surroundings. I took to always carrying a handkerchief or Kleenex with me at all times.
More later, and happy strokin'!