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JackinWorld Biography #97

Part One of a four-part series.

This is a shameless account of the masturbatory experiences of a man who has masturbated regularly since he was 14 and who now, as he approaches 60, considers masturbation to be one of the most enjoyable sexual experiences of all and an art in its own right.

My discovery of the existence of masturbation, although not the pleasures it offered, was at prep school at age 12. I had, of course, experienced erections but had not associated them with particularly pleasurable feelings. In the dormitory we paired off and got into bed with our partner and played with each other's penises, but I never got an erection doing this, even though my partner did, and I was never aware of anyone doing anything except "fiddling." Then, one evening, a classmate — who was considerably more sexually developed than I, with a bush of pubic hair and a thick penis — persuaded me one evening after "lights-out" to join him in the classroom to do some "homework" — something we "prefects" in charge of dormitories were allowed to do. We were in our pajamas, and as soon as we sat down he put his hand inside the front of mine and started stroking my penis. I was surprised, but not particularly shocked as I was a little in awe of him and the size of his penis, and also he had done the same to me once when I was in the bath. He took my hand and put it on his penis, which was erect. My penis remained flaccid, and he told me to try to pee into my pajamas — why, I couldn't think, though the idea attracted me. I tried but did not succeed, and my penis remained limp. He encouraged me to rub his penis up and down which I mechanically did, and eventually he took out his handkerchief, covered his penis and continued to rub it himself. A damp stain suddenly appeared on the handkerchief, and I innocently thought he had peed into his handkerchief, the pleasure of which I could understand as I took pleasure in peeing a little in my pajamas after lights out and had recently been accused of wetting my bed because of the yellow stains discovered on my pajamas and sheets.

So I first experienced masturbation without having the slightest idea what it really was. When I moved to a grammar school, masturbation ("wanking") was the main topic of conversation, and I was made to look a fool — it was obvious, from my reactions to the accounts of their exploits, that I did not do it. They would talk about "shooting" competitions that took place on "the island" on the river where the school went swimming. It seemed that the idea was that each boy masturbated in turn, shooting his sperm as far as possible. The furthest point reached by his sperm was marked, and of course the winner was the firer of the longest shot. Mutual masturbation was also rife, though of course I was left out of it and had no idea it was happening, and eventually the authorities decided to bring it to an end. Each boy was given a questionnaire that asked with whom he had done it and how often. Being still naive and innocent I thought this was referring to "pilling," which was quite simply playfully grabbing at one another's private parts, another popular pastime. I had done this occasionally to another new boy and dutifully admitted as much when answering the questionnaire. Fortunately they realized I was not a mutual masturbator and I was not sent to the headmaster for a caning, the punishment administered to all the self-confessed onanists. Later I was to regret not having gone through the mutual masturbation phase — it is still among my fantasies.

The "unlucky" ones seemed to have learned their lesson as talk of masturbation all but ceased — in fact, it was now generally considered something one "didn't do." It was all right for them, but it was something I had never tried, probably simply because I was a late developer; I was 14 before I had anything like a reasonable bush of pubic hair. I enjoyed playing with my penis, I would often get an erection, and I enjoyed rubbing it up and down — but so far it had gone no further than that, even though I knew something should happen.

Then, one evening as I was doing my homework, I started playing with my erect penis and a wonderful feeling came over me. I could feel something happening down there, something that required me to continue rubbing more and more vigorously. I did so, the blissful sensation intensified, and suddenly something welled up inside my penis and it exploded. A thick white liquid leapt out in spurts and went all over my desk, my trousers, my hands — and the feeling was out of this world! I had masturbated and experienced my first orgasm. Of course I could do nothing about the feeling of guilt that overwhelmed me — but even that could not detract from the pleasure I had experienced.

The next morning, however, it became clear God had punished me for my sin — my penis was crooked! It curved in a semicircle and looked most strange and unnatural. How could I appear naked in the shower? Everyone would know what I had done. I rubbed it into an erection — and the situation was even worse. It was deformed! I felt awful for all of 2 days, and then the urge to masturbate again became stronger than the shame at the deformation of my penis. At least I now had nothing to lose! I masturbated without any feeling of guilt — and when the erection subsided I had the impression the curve was less obvious. Well, I had better make sure. True enough, after 2 or 3 more sessions of sheer bliss, my penis was straight as an arrow. The only difference between my pre- and post-masturbatory penis was that the foreskin had started to recede, which eventually gave the impression that I had been circumcised.

I was now definitely a masturbator — nothing could alter that — so I masturbated regularly, but of course kept it to myself. By that point masturbation was rarely talked about at school, and when it was, it was usually presented as something other boys did. I began to feel I perhaps shouldn't be doing it. But I continued — and not always privately. I found that by tucking my erect penis under my left thigh I could, by sitting on my left hand, masturbate during lessons. I was once seen by a schoolmate who accused me of committing the forbidden act, but I rather unconvincingly denied it, and no more was said. Whether there were any semen stains on the back of my trousers, I don't know. There should have been, considering the amount I usually ejaculated.

For some reason, the best mathematician in the class, a rather strange boy who had an uncoordinated walk, was known to be a regular masturbator. Perhaps it was well known because other boys had done what I was destined to do with him. One afternoon he and I were alone in the classroom doing some revision and chatting, when he started rubbing his trousers. He then opened his fly and took out his penis, silently suggesting I do the same. I needed very little persuading, and when we both had firm erections we each spontaneously took hold of the other's penis. His was smaller than mine — thinner at least — but it was a thrilling experience that heightened the excitement welling up inside my penis. I ejaculated very quickly, spurting sperm all over my trousers. He seemed not to want to ejaculate, as he immediately pushed his penis back into his trousers. I think we then both went our separate ways and no more was said about the occurrence. It had a traumatic effect on me, though — I was mortified at what I had done, and I think this act was the driving force that made me want to become a priest, as if to do penance for committing an unpardonable sin.

There was no more mutual masturbation after this, but I did take part in a very harmless "circle jerk" session with a group of schoolmates at the home of one of them one Saturday afternoon after school. We were sitting in his room chatting, and it became obvious that one fellow who had a massive penis (everyone knew that as we all swam nude in the river) had gotten an erection. We joked about it, but this ensured that most of us got aroused, too. Nobody took out his penis, but one by one we started masturbating, and it was pretty obvious we all ejaculated in our pants. The fellow with the large penis fascinated me — I used to sit next to him in the chemistry lab, and one day he drew my attention to his erection. I playfully nudged his leg with mine so it squeezed his penis against his other leg, and he silently encouraged me to continue. Afterwards he mentioned you didn't have to actually touch someone's penis to masturbate him.

Go to Part Two.


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