My first orgasm, at the age of eleven, was a mix of pleasure and the most exquisite agony a pre teen could fathom. I was alone in the house, I had my pants around my ankles, and like other afternoons before this one, I was gleefully playing with myself, letting the foreskin role up and down as I humped the plastic inside of a roll of scotch tape lined with cloth to make it nice and soft. It felt great, and my dick was small enough that it did not get stuck when I was hard. 1950s medical dictionaries were all I had for reading material on anything relating to puberty. I had some wisps of black hair around my dick, and knew, from reading that medical dictionary, that I would have something called a 'first emission' soon.
I did not know what it was exactly, I assumed it was like peeing in a way, except there was supposed to be a 'pleasurable sensation radiating out from the penis' otherwise called an orgasm. It all sounded rather complicated, and I was not sure if I could only do it during sex or if I could do it on my own. The section on masturbation had very little detail on how boys could masturbate, only that they did. I had what I now know to be dry orgasms before this point. That was why I was stroking myself this particular afternoon. if I did it long enough and touched myself here and there, it felt really, really good, reminding me of the times I played doctor with a neighbor boy and girl. So, in search of this good feeling, I gently slid my foreskin back and forth. I had a few hours before anyone else would be home, and could take my time. I felt like I needed to pee, but peeing when erect was harder than when I was flaccid, so I resolved to hold it until the expected good feeling. The urge increased, however, but I kept stroking, more earnest now, grip tightening around my foreskin and glans. And then it happened.
I thought at first that I was going to pee, but my cock had never felt this good before doing that, so it must be something else, and indeed it was. As my foreskin slid down, I ejaculated. I was screaming as shot after shot of semen squirted out of my cock and ran, warm and thick, over my fingers. My body was rocked with a wave of indescribable pleasure as I kept stroking even after I stopped cumming. I realized I needed to clean myself off, so I grabbed a nearby box of tissues and wiped my crotch dry, relishing the smell of my ejaculate as I did so. I flushed all but one of the cum sodden tissues, keeping one as a reminder of my first orgasm.
I would have to tell my friends about this new discovery.