How I Learned to Masturbate

By Five Hole Punch

Published on Nov 29, 2014

Gay

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How I Learned To Masturbate Supplement One

Here are a few more that I have received from readers.

  1. Hans

"I can't say whether I learned on my own or from observing my companions first. I definitely went into the woods with my schoolmates well before puberty and we would show our penises and buttocks to each other. We would masturbate, before we could ejaculate, so we were about nine or ten years old. We looked at pornographic magazines that we stole from our houses, fathers or older brothers. We looked at the pictures, but it was just exciting to do forbidden and naughty things together, like smoking cigarettes and using curse words. We danced around, moaned like we imagined people having sex would, rubbed against trees and each other. We would masturbate standing before each other or sitting next to one another on a fallen trunk.

One thing about my masturbation as a boy was that I really abused my genitals. I handled my penis and testicles roughly, stretching and slapping them. I would pull my foreskin far forward and it would pull my testicles forward, also. I could tighten my stomach and make my testicles pull up in my scrotum and make my penis jump without touching it. We handled each other roughly, also. I should mention that no one had pubic hair and my penis was only about 8 centimeters when hard. I would have pleasure that was like pain, my muscles would tighten, especially my abdomen, but I did not have mature orgasm until I was thirteen years old."

  1. Gerald

"I learned what fun my hard penis was when I was only five or six. I was at the playground on one of those spring mounted metal rocking animals, a duck as I recall. The metal was cool on my legs and I got hard in my seersucker shorts on a hot summer day as I rocked against the neck of the duck. I worked to achieve the right rhythm, too fast and it hurt as the spring sprung back with too much force. Once I had the right rhythm I concentrated on the feelings tickling my privates; they were intense. I imagine it was noticeable to anyone paying attention as I really spent some time rocking, at least five minutes non-stop. I did this regularly when I went to the playground. Later, I casually played with myself in the bath off and on throughout elementary school. The bubbles covered my penis when necessary. No intense feelings, but I still did it more than not when taking a bath.

I didn't achieve an orgasm until I reached eleven. We had a small in ground pool and a very small pool house next to it. It really was just half a storage area for pool equipment and half a changing room with a small five foot wooden bench, cubbies for towels and clothes, a sink and counter and a small refrigerator. I used the changing area like a playhouse where I could be alone and, most importantly, be naked. I knew that if I got caught naked I had the excuse that I was changing into my swim trunks. I never really had to use the excuse, though.

I would take my clothes off and stay naked for quite awhile. I masturbated sitting, standing, and humping my hand lying on the wooden bench, which was rather uncomfortable, even with a towel under me. I fingered my butthole, too. It was the summer I turned eleven when I had my first real orgasm. I was sitting with my back against the wall and my legs up on the bench when the feelings in my cock got more and more intense. I pushed back hard against the wall with my neck and my butt muscles tightened. My cock started throbbing and I went to heaven! This was my new favorite game that summer and for long after."

  1. Scott

"My masturbatory education began with my big brother, Bill, who is six years older than me. We shared a bedroom in till I was 7 or so, and he was a horny, cum-filled 13-year-old.

Bill was a lanky kid, with a wavy dark brown hair and a bad attitude, though because of our age difference we didn't see a lot of each other and got along just fine when we did. Me, I was just a little, shy blonde kid.

Naturally, I was usually in bed well before Bill, but occasionally I'd be up late enough that we would be getting ready for bed together. One night, as we were undressing, he asked me if I wanted to see something cool. Of course, I said `sure,' probably expecting to see some new addition to his sport card collection or a new catcher's mitt. Instead he dropped his jeans and white jockeys to reveal what looked to me like an immense, throbbing boner, probably 6 or 7 inches long.

Mesmerized, it seemed to me the most natural thing in the world to reach out and wrap my hand around his hard cock. I don't remember asking permission and he certainly didn't object. And it seemed just as natural to start slowly moving my hand up and down the shaft. `Show me yours,' he ordered, so of course I complied, pulling down the bottoms of my flannel PJs our grandmother sewed for me. He grabbed my little prick, though what he did seemed more like tugging then jacking. No doubt there wasn't that much to hold onto and I suppose he was more interested in what I was doing for him.

We went on exploring each other for a few minutes, but Bill wanted to speed things up so he replaced my hand on his cock with his own, finishing himself off. I thought watching him shoot white, creamy stuff over his hand was pretty cool, but we soon covered up and headed for bed like nothing happened.

This scene was repeated several times before we move to a new house. Bill and I scored our own rooms, he discovered girls, and our fun wasn't repeated.

But that wasn't the end of his contribution to my education.

Thanks to Bill, I had a new appreciation for my little penis and happily played with my hard-on every chance I got, though I usually manhandled it like the stick shift of a sports car or ground it mercilessly into my pillow. I had yet to discover the joy of orgasm.

That changed when I was 11. I hit puberty early, my hair darkening and beginning to appear on my legs, under my arms, and around my dick. Even better, my cock expanded at a nice rate and I enjoyed showing it off with my buds or to neighborhood girls in exchange for a glimpse of some hairless pussy. When the parents were out, leaving me in the care of a cute high school girl, I'd bone up and, carefully positioning my shaft for optimal tentage in my PJs, casually display myself in front of her. Not for the last time, a hot girl ignored me.

Fortunately for me, Bill dispensed with the trading cards and built himself an impressive collection of porn. In those pre-Internet dark ages, we're talking about magazines like Playboy and Penthouse, and a few grittier titles like Hustler and Club. They were all neatly arranged on the bookshelves in his bedroom across the hall from mine.

I remember my mother complaining about this to my dad, who defended my brother, saying he was `just curious.' They didn't mention any perceived risk this stack of smut posed to the morals of their youngest son, but I guess they assumed I was too much of an angel to snoop.

But, snoop I did. My brother was rarely home, and when my parents were out, as they often were, they'd leave me alone or with a sitter (who would disappear down stairs in front of the TV as soon as I went to bed) and I'd soon be in Bill's room pilfering his stash. (All it took to give me a raging boner was the smell of my mom's perfume, because it was a signal that my parents were ready to go, leaving me free to satisfy my pubescent porn addiction).

Before long I'd be back in bed, my PJs on the floor, drooling over an airbrushed Playmate or studying a particularly enlightening letter to the Penthouse Forum. My free hand would be wrapped around my aching cock and I always stroked it slowly to prolong the pleasure. Of course, I didn't know that the best was yet to come.

Anyway, this one night I was happily home alone and, after enjoying a particularly long and sweaty wank, I felt the building sense of urgency my groin. Convinced I was going to wet the bed, I tossed the magazine aside, grasped my raw, throbbing prick, and dashed to the bathroom. I remember laughing out loud, realizing even then how ridiculous I must've looked, a skinny 11-year-old kid racing bare-ass down the hall with a death grip on his cock.

Of course, I made it to the toilet and relaxed my grip in time to see a few streams of white stuff shoot into the bowl. Thanks to my earlier education, I realized right away what it happened: `So that was my fucking sperm!' I said in awe.

I made my way back to my bed, feeling both very satisfied and suddenly adult. Grateful to have discovered such an amazing new skill, I made sure I was jerking off and shooting jizz whenever and wherever I got the chance. My mom couldn't have helped notice the sticky mess her little angel was leaving on the sheets and in my briefs every day, but she never said a word. I guess she assumed it was her baby, like his big brother, just being curious."

  1. Doug

I began to masturbate at the age of 11 ¾ when I discovered the good feeling of rubbing the head of my penis with a wash cloth one day while taking a bath (I had overheard guys at school talking about jacking off, but I really had no idea what they were talking about). As I continued to rub it, I was soon overwhelmed by my first orgasm, dry, as all my muscles tightened up and I felt like I was going to jump right out of my skin!

I almost immediately discovered that I could achieve the same feeling using my hand and soon I was masturbating nearly every day, almost always at night and in bed. I soon found out that by trial and error, I could have multiple orgasms during any one session. Now it usually took four to five minutes of stroking to achieve the first orgasm which was always very intense. All my body muscles would tighten up as I climaxed and my stroking arm would actually lock up; I couldn't have continued stroking if I wanted to.

The first couple of times I jacked off it felt so good that I tried to start stroking again as soon as my muscles relaxed enough to allow that - maybe five or six seconds after the orgasm hit. I found that to start stroking again so soon actually hurt - my body and especially my cock head was still way too sensitive. After some trial and error, I soon realized that if I waited about twelve to fifteen seconds for the intensity to diminish and my muscles to relax and the sensitivity to wane, I could start stroking again and bring on additional orgasms with only about fifteen to twenty strokes on my penis.

Boy was that great! I was essentially going from one orgasmic high to another without having to start all over again from scratch, a process similar to that which some women experience. What I had discovered was what I called my "window of opportunity." As noted above, I had to wait for the sensitivity to decrease until the right moment to begin stroking again. However, if I waited too long I would "lose it" and have to start all over again from scratch. Anyway, I almost always had four or five orgasms and sometimes as many as six or seven during one session. I was always exhausted at the end of each session and quickly fell asleep.

About a month before my 13th birthday I was having a session as usual and notice when I orgasmed I had a drop of clear oily substance on the head of my penis. I had had my first ejaculation!

During the next several weeks I noticed many significant changes in the way my body was functioning sexually. First, I noticed the time necessary to achieve the first orgasm dropped rapidly. As noted above, the first orgasm used to take four to five minutes with approximately 500 strokes needed. This fell to where I was consistently able to reach that first orgasm in a little over two minutes with only about 200 strokes needed. That was the good news.

The bad news was that I rapidly lost the ability to achieve additional orgasms per session and soon had to "start all over again" if I wanted additional orgasms. At age thirteen that really wasn't a problem as I could achieve a second orgasm and ejaculation (with less cum) with an additional 200 strokes. The waiting period was generally only a couple of minutes and sometimes I even maintained an erection during the "recovery period." The additional work needed to have multiple orgasms and ejaculations meant that I soon, by age fourteen or fifteen, was content to have only one orgasm and ejaculation per session.

The other bad news is that the intensity of the orgasms diminished considerably. As noted above, I had been consistently having very intense orgasms, even after having several in rapid succession. Then the nature of the orgasms changed; I was now having multiple muscle contractions needed to shoot several spurts of cum out of my penis when ejaculating. I found that from the day that I noticed the first drop of clear cum on my penis, it took about four to six months before I was ejaculating the usual amount of creamy white cum. This usually took place in two spurts (ropes), each approximately two inches long, which shot six to nine inches (occasionally to twelve inches) up on my chest and an additional muscle spasm which resulted in additional cum oozing out of my penis.

It is only been in the last few years that I've come to realize that my experience as a young boy and my ability to have multiple dry orgasms in quick succession is a somewhat rare phenomenon. Perhaps less than 15% of pre-pubertal males have the same experience which I had. The rest experience pelvic muscle contractions, just as they do later on, just no jizz comes out when they experience a dry orgasm.

Although I've always enjoyed my masturbating sessions through these many years and the resulting orgasms and ejaculations, I often long for the days of pre-puberty and those wonderful, intense multiple dry orgasms (and with no mess to clean up!).

  1. Tino

"I was getting boners at ten that seemed to last longer than they had when I was younger. I would touch them, but not really masturbate, just touch. My parents had gotten a computer and I tried it out just because it was new. It wasn't long before I discovered pictures of naked people doing stuff I had never seen before.

I liked to get naked when I was left alone in the apartment. I got naked and looked at these pictures and really fingered my cock. It felt great. I spread my butt and fingered my butthole with my fingers like the ladies in the pictures were fingering themselves. I sat on my thumb and masturbated my cock with my other hand. I came dry. It was unbelievable. I wanted to cry out. It hurt and felt so good at the same time. I came a bunch of times."

All Rights Reserved. Copyright 2014.

Next: Chapter 6: Supplement 2


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