I grew up with a particular problem. The foreskin on my penis remained attached to the glans (head), a condition called phimosis. As I grew up, the skin became even tighter and was impossible to pull back, even when I sat in a warm bath. The problem worsened when my penis started its adolescent spurt of growth. The band of skin around the urethra opening stayed small and very tight as the rest of my penis grew. An erection was quite painful. I was too embarrassed to talk to my friends about it but finally asked my dad. He told me that I would grow out of it soon enough and just to laugh it off.
I heard guys at school talking about shooting cum, jacking off, etc. They talked about how good it felt but that was not how I saw it. There was no way that I would bring on an erection and try to stroke my penis - it hurt too much. So I was never sure what nice feelings they were talking about. I learned what my own cum looks like when I turned fifteen. That's when nocturnal emissions (wet dreams) began, usually once or twice a week. There weren't any erotic dreams with the nocturnal emissions though, in fact I often didn't wake up at all until the next morning. Sometimes I did wake up during the night, just after ejaculating. Usually my penis was semi-erect sometimes quite flaccid - never erect. Depending where my penis was positioned, the semen might be running down my testicles and crotch, or on my belly or sometimes seeping down my leg. It was all a real bother because I had never experienced orgasm - just this mess of cum to clean up. Sometimes I'd remembered to place a small face cloth in my briefs, over my penis before I went to bed to try to avoid making a mess. Often though, the cloth would end up shifting position during the night so there were plenty of messes to clean up. My mom never bothered me about the crusty briefs that would show up in the laundry basket.
The summer I turned sixteen I spent some time at a cottage in the Adirondacks with my cousin and his parents. We all did a lot of swimming and laying about on the beach. It was likely there that I picked up an infection of some sort. The area between my foreskin and the glans (head) became infected and swollen. I was too embarrassed about it to mention it at first but very quickly my whole penis became red and inflamed. In the morning I couldn't urinate and had severe pains in my stomach. I was hot and felt very sick. I finally told my uncle about it and he drove me to the local town clinic. The doctor said there was an acute infection and that the foreskin had to be removed right away. My uncle reluctantly agreed and before I knew it, I was stretched out on the clinic table in a surgical gown. The doctor inserted a needle into the base of my penis to freeze it (local anesthetic) and forced a catheter into the urethra. What a relief as the pent-up urine shot out of my bursting bladder. Next came the circumcision. The doctor did the procedure quickly but did it hurt - even with the freezing. I'll never forget the searing pain as he snipped the foreskin - even with the anesthetic. Within a few minutes my penis was without its hood - I was circumcised.
The antibiotics quickly cleared up the infection and the 'surgery' on my penis slowly healed. I had to get used to having an exposed glans (head) for although it was a relief not to have the tight foreskin pressing on it, the glans was super sensitive for a long time. Even months later, I would change my briefs with care not to rub too much. Nocturnal emissions (wet dreams) continued as before but still there was nothing 'pleasant' about them - just the inevitable mess of cum to clean up.
About two months after my circumcision I secretly watched my cousin Jeff masturbate. It was the first time I had ever seen anyone stroke his penis to ejaculation. He was and his parents were staying over at our home while passing through. We set up a cot for Jeff in my room. Jeff was a year older. I was asleep before he even came into the room. The next morning I awoke to the soft sounds of springs squeaking. Without raising my head, I peered over toward Jeff's cot. There he was lying naked on his back, his boxers around his ankles and the blankets rolled back. He was staring straight at the ceiling, slowly stroking his penis with one hand and cupping his testicles with the other. I watched him for several minutes, completely fascinated. Then he stiffened his legs and bent his head back. Streams of semen spurted from his penis onto his belly and chest. I stayed absolutely quiet. Jeff lay there for a few minutes and then proceeded to clean up with his underwear and headed off to the bathroom. The whole episode amazed me. I still couldn't bring myself to stroke my tender penis (although I now had pain-free erections) and I assumed that what Jeff had just done must have hurt him somewhat. Being so used to penis pain all my life, I misunderstood Jeff stiffening his legs and bending his head back. I thought it must be part of the pain that went along with masturbating. I didn't mention my 'spying' on him so my ignorance of all these delicious things continued on. And I made no attempt to copy Jeff's example.
At eighteen I headed off to college. My new roommate Don soon set me straight in the ways of men. Our first night in the dorms he asked me right out if I jerked off. I said that I hadn't tried it because I wasn't sure I could take the pain of it all. 'Pain?' he yelled back. He couldn't believe that anyone could have such a distorted view of masturbation. Needless to say, he quickly explained the delicious results of stroking one's penis and demonstrated for me to set the record straight. As I watched him go through all the same motions that my cousin had done a year earlier, I realized that there was more to this than I thought. With lots of lube I very slowly followed suit. It took awhile. But eventually I began to feel the onslaught of my orgasm. When that final crescendo of ecstatic pleasure finally began to build, I couldn't contain myself. Don's friend opened the door to our room as I as going over the brink but I just couldn't stop, I was out of control. And I didn't care. I just stroked and stroked until the semen spued from my penis like a miniature gyser. Yes, there was lots of semen. Yes, it was embarrassing afterwards, especialy with Don's friend in the room. But it was the sheer all-consuming pleasure that I remember vividly to this day. I almost fainted from it all. It was so completely unexpected. All those years and I never suspected that sex pleasure could be so intense. And never since that first masturbation session have I experienced such intensity of pleasure, either alone or with my wife.
That was twenty years ago. I quickly became a confirmed master of masturbation. Even after marrying I continue to pleasure myself whenever I can.