How I Learned to Jack Off

I learned how to masturbate strictly by accident although I can’t remember exactly how old I was.

When class at school let out for recess, we would all go out to the school playground. There was a large swing set that was supported by metal pole in an “A” shape. The poles were about four inches in diameter. Some of the boys, including me, would wrap our legs around the poles and climb up while the girls were in the swings. I noticed that it felt good for my penis to rub against the pole. I learned that the trick was to hunch up the pole a couple of inches and then slide back and inch or so. This felt incredibly good. After hunching up and sliding back a number of times, I achieved orgasm. And that produced the best feeling in the world.

Of course it was a dry orgasm but what a wonderful feeling. In my kid brain I thought I had discovered something that no one else knew about. I was hooked. I did it every single recess. Surely the teacher knew what I was doing. In retrospect it had to be extremely obvious I was jerking off.

Then disaster struck. I hunched the pole and had an orgasm but also felt pain in my penis. I slipped my hand down my pants and felt wetness. No, I hadn’t cum. This wetness was blood. My hunching friction had torn my foreskin.

I only lived a few blocks from the school. I told the teacher I had an emergency and had to run home for a few minutes and took off. Both my parents worked so no one was home. Thankfully my dick had stopped bleeding by the time I got home but my Jockey shorts were soaked in blood. Miraculously, none had soaked through my pants. I cleaned myself up and threw away my bloody shorts and went back to school. The teacher never asked any questions thankfully. That curtailed my masturbation for a few weeks.

Amazingly, I didn’t figure out that I could duplicate the swing set pole activity by jerking my dick off with my fingers. That came a bit later. My best bud at the time was another kid my age named Denny. As class let out one day, an older kid told Denny and me that he had something to show us. He led us back into some bushes where he unzipped  his pants and took out his erect penis. He invited us to both do the same but we were too shy. He proceeded to jack off in front of us and very quickly produced several squirts of semen. I really can’t recall if I was aware that semen could be produced by jerking a dick, but in any case it was quite an eye-opener. I learned then that orgasms could be achieved by hand.

Now that I knew I could jack myself off with my own hand, that became a daily activity. And at some point I produced some semen. I also had regular wet dreams that were quite pleasurable, but messy.

My family lived on a large wooded 40-acre tract. The back of our property butted against Fort Belvoir and extensive training exercises took place in those woods. I used to prowl those woods and one on of my trips I ran across a group of wooden benches. It may have been a resting point for soldiers training in the woods. One of the benches had an incredibly detailed pencil drawing of a couple fucking. While I was vaguely aware that a man put his penis inside a woman’s pussy, I thought once the insertion was made, the two just lay together. Somehow I hadn’t connected the jerking of my cock with movement inside the woman’s pussy. But the drawing made it very clear with a series of motion lines behind the guy’s butt showing that thrusting was occurring. Then a light bulb went off over my head and I realized what actually happened when fucking took place as I connected that to my jacking off.  

Later I was very active in a scout troop. In fact my dad was the scoutmaster. We had gone on a two day hike  on the Appalachian Trail. There were about 12 scouts, my dad, and a junior assistant scoutmaster.

We found a spot to overnight at a little campsite that included a three sided lean-to. Four of us, along with the assistant scoutmaster, gathered in the lean-to while the rest pitched tents. Everybody had settled in for the night in our sleeping bags on the floor of the lean-to while the assistant scoutmaster was on a raised bench at the back of the hut. It was pitch dark when the voice of the assistant said, “Hey guys, look at this.”

He turned on a flashlight he held in one hand that illuminated a big red cock that he was masturbating with his other. He must have been jacking it for a while because just as he shined the light on  his dick, a large amount of cum was oozing out. I remember being very fixated on what I was seeing. My cum always squirted out when I came but his was just flowing out of his dick. It was also very, very thick and not near as liquid as I was used to. He kept the light on the flowing cum as he milked every last drop out. Then turned it off. Not another word was said and as far as I know, nobody even mentioned it to one another the next day. I wondered if I should tell my dad but was too embarrassed to bring up something like that.

The only porn that was available back then was the rare 8-page bible that would turn up and get passed around. If I was lucky enough to get to hang onto one overnight, it would produce a frenzy of jerking off. I do remember one time jacking off five times in one night over an 8-page bible. They are available for downloading on the internet now and while I find them slightly arousing, it’s also amazing to me that I would get so excited looking at one to jack off five times.

By the time I was 15 I had discovered the joys of pussy and all through high school much of the cum I produced was achieved with a partner although I still enjoyed  jacking my dick as frequently as possible.

Hard-ons in class were a constant daily activity. I had one pair of pants that had a large hole in the pocket and I would pull the head of my dick through the hole and massage it with my fingers in class. A couple of times I went too far and shot my cum into my pocket. As soon as class was over I would rush to the boy’s room for a secret clean-up. I would also try to achieve at least one orgasm a day in one of the stalls in the boy’s room. Sometimes I might jack off in there two or three times a day. Being a teen, it never took longer than a couple of minutes to shoot a load into the toilet. I’m sure plenty of  my classmates were doing the same thing but I never knew or even suspected that others were doing the same thing I was.

It's kind of amazing how easy it was to get hard back then. I could be sitting in class and just look at one of the girls sitting around me and instantly get hard. Looking back it almost seems like I was erect about 90% of the time in class. When getting up to go to the next class I would have to hold a book in front of me to hide my hard dick.

I focused 100% of my attention on the girls in high school and never paid any attention to my fellow male students who all probably had hard-ons as frequently as I did. Looking back I now wonder how many of the young female teachers were aware of all the hard dicks that were probably in their classes. I’m not sure how many of the female students were cognizant of being surrounded by a bunch of horny boys with throbbing cocks in their pants. Probably a bit different in the high schools of today where all the students are a lot more hip to what’s going on around them and way more sexually aware than when I was in high school.

At least from a sexual standpoint, I would love to be a high schooler today. Although I can’t really say I was sexually deprived during my days in high school. By the time I was a senior I had a steady girlfriend and we fucked every chance we had. At least four or five times a week. It’s a miracle we never got caught. We actually were sort of caught once by another couple who we were going to the movies with. We were at my parent’s house waiting to get picked up. I was lying on the sofa while my gf straddled me and bounced up and down on my cock. The other couple arrived way early and walked in on us.

We were both fully dressed and my gf’s skirt covered everything but there was no doubt as to what we were doing. They said they would wait in the car and left. My dick had gone limp so we didn’t finish. Nothing was ever said about it.

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