I was 12 when I had my first orgasm. My two-years-older brother had mentioned something cryptic to me about rubbing myself to see what would happen. I really didn't know what he was talking about, but then I've always been a bit naive and public information and attitudes on masturbation in the 60s is not what it is today.
How naive was I? I remember not realizing that rubbing myself in public wasn't appropriate. One time I recall, my family was watching some attractive women showing their legs on tv in fishnet stocking (it still makes me horny), and sliding on the carpet to rub my crotch. This was with my family there! I recall after doing this that I turned and found my mother smiling at me (not in a sexual way, more in a motherly way--which was enough to make me realize that just maybe this wasn't the thing to do).
When I went to bed I was curious what my brother had been talking about. That night I was alone in my room. I was lying there with the lights out but my open door allowed the light to filter down the hallway from the bathroom. Not being tired and remembering my brother's remarks I decided to find out what he was talking about.
I way lying on my back and wearing pajamas...the soft terry cloth kind. I started by sort of squeezing my penis to make it a bit hard, and then when I became firm I took to rubbing along the length of my penis with a couple of fingers over the pleasantly soft pajamas. The soft pjs made a very nice feeling and I became hard within just a short time.
It felt good to rub myself, but this was no different than had been happening for some time. I knew there was something else he had meant for me to discover. Not really knowing what I was doing, I continued to rub myself through the pajamas and as I did, the feeling between my legs grew stronger and stronger. As the feeling grew stronger the speed with which I rubbed increased. After a period of time that seemed long but was probably only a matter of a couple of minutes there arose from very deep inside me a new feeling. It was very intense and stretched from my penis, up my body, and to the base of my skull. It was more than the feeling of pleasure that you get from rubbing your penis. Looking back now, it was like my entire body was in orgasm. The feeling was so strong that it scared me and I stopped rubbing. By that time, though, things had been set in motion and my body took over to deliver my first orgasm. My penis convulsed very strongly 6 or 7 times, and with each pulse it spread cum all over the inside of my pajamas.
Afterwards, the feeling was a mixture of pleasure and surprise. I cleaned up in the bathroom but with the type of material my pjs were made of there was no way to really clean them up.
This was the first and still the best orgasm I've had. I've tried to use abstinence to build up the pleasure, which works only to a point. That first time will always stand out for the intensity of the feeling.