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Learning About and Enjoying Masturbation

My first recollection of deriving pleasure from my penis was around age 9 or 10. At that point, it was nothing more than a few of us boys in the neighborhood showing each other our dicks. It was not uncommon for us to stop to take a pee when we were wandering in wooded areas, so we had seen each other's dicks at various times. But, we began to make a "game" of it even when we didn't have to pee. I guess it was the excitement of having our dicks out of our pants outdoors or indoors just to show off. We teasingly stroked our dicks as if aiming a pee stream at each other. If we got hard, we didn't have any real association to it.

I had toyed with my dick while laying in bed at night for as long as I remember. After showing off with the other boys, I'd still be a bit excited and my dick would get hard recalling the earlier events. I found it pleasurable to stroke my smallish dick and found that the longer I did, the better it felt. I knew nothing about ejaculation and didn't have one at that time.

About the time I turned 11, an older boy of about 15 in the neighborhood approached me. I was a bit leery because he had a reputation as a bad boy. He did nothing threatening to me and offered no more than an opportunity to explore an old garage together. Little did I know what he had in mind. After exploring a bit, he said he had to pee and asked if I needed to pee also. He flopped his dick out and aimed his pee stream against the wall of the garage. I took my dick out and started peeing also, then put it back in and zipped up when I finished.

Of course, I could see the other boy’s dick and the pee stream, which was no big deal since I had seen most of the other boys. This boy's dick was larger and it got even larger while he was peeing. I couldn't take my eyes off of his dick and he seemed to enjoy me watching him stroke it bigger and bigger. He asked if I knew about jacking off and I said I didn't. He asked me to stoke his dick, which I did for a moment. Then, he took his dick back in his hand and finished masturbating and ejaculating. I wasn't quite sure what to say or do, but he seemed satisfied that I had watched him jackoff.

After that episode, I became more eager to see if I could do what I had seen him do. The event with that boy was never repeated, for some reason, but he gave me a lot of insight into the pleasures of playing with one's dick. I can't say that I played with mine any more than before, but I understood the objective much more clearly. Very soon, I began to ooze a drop or two of semen when I stroked my dick until I thought I couldn't stand it any more. Before seeing the other boy cum, I always stopped stroking my dick when the feeling got too intense. When I felt how good it could be, I tried to cum every time I masturbated.

It was about that time that I realized my dick was starting to get bigger. Before long, my ejaculations became larger and I understood how to jackoff for more pleasure. I never had much pre-cum but by letting my cum flow back down over my dick the intensity was fantastic. Needless to say, I had developed a whole new appreciation for my dick!

The other boys I played with all the time noticed my dick getting bigger when we would pee together. They ranged in age from one to about three years younger than I was. Since my dick was getting bigger, they admired it and some of them touched it, especially when I got hard. One day when we were in the woods and had finished peeing, I kept my dick out and stroked it until I was very hard. I dropped my shorts to feel more fresh air on my body and stroked my dick until I shot a nice stream of cum. The boys were amazed and asked how that happened. I explained that’s what happens when a boy’s body is ready and he strokes his dick long enough.

By the time I was 12, I had a nice bush of pubes and my dick was almost 7 inches long. I played with my dick as much as I could – probably too much, but it felt too good! The other boys and I still liked playing with our dicks together and they especially enjoyed seeing me cum. One of the other boys would jackoff with me but not cum. Then, one day, I had jacked off and he kept stroking until a couple of drops of cum oozed from his dick. He was excited and I felt good for him!

Those types of events continued until my parents bought a new house and we moved when I was 13. There were a couple of boys around my age in the new neighborhood but I didn’t know how to approach them about what I had enjoyed with the boys in my old neighborhood. I enjoyed solo masturbation a lot, so I wasn’t really missing much! There was a wooded area near the house and I enjoyed being able to go to a secluded area and taking all of my clothes off to have a jackoff session.

I had become more interested in girls by this time in my life, of course. Unfortunately (or maybe fortunately), while I liked to make out with them, I had no idea how to get started on intercourse. Most girls wouldn’t go all the way during those years anyway. I got to feel some breasts and a couple of them let me play with their pussies. After a nice make-out session, I could hardly wait to get alone so I could jackoff and relieve my hardon.

After finally getting my dick inside my first pussy at age 19, I was hooked! When I could have “real sex”, it was great but it didn’t stop me from masturbating frequently. A few months after getting my first pussy from a long time girlfriend, I began to date another girl. We soon became lovers and I really enjoyed the regular sex. I still had to jackoff occasionally because it felt different and I could control the feeling better. Of course, the more I learned about intercourse pace and methods, it was fantastic!

I’m now retired and still have the love affair with my dick! My first wife would watch me jackoff when she was in her period and sometimes she would stroke me off. My current wife and true soulmate has no issue with me masturbating, although she’s always ready for a nice session of sex. I’ve jacked off in front of her a few times but the usual way we watch me cum is for me to pull out when we’re fucking in the missionary position and shoot my cum on her tummy.

Another pleasure I’ve enjoyed a few times is having a male friend watch an adult movie with me. It takes little time for a man who is straight as can be drop his pants and stroke his dick in that situation. I’ve never considered that type of situation to be even remotely “gay”, just a couple of men doing what we men do all of our lives.

Thanks for reading my life story about masturbation. Send me a PM if you’d like to share with me.

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