How I Learned to Masturbate

By Five Hole Punch

Published on Jan 26, 2023

Gay

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  1. Zach

"What I remember is starting at around 6 years old. I know I was 6 because I was missing my front tooth when I discovered the fun of playing with my cock. Two things led to this discovery, both happened about the same time and I can't say which caused the other.

The first was a terry cloth robe that I put on after my bath. For some reason the terry fabric felt great on my body. It would be partly wet and I would go and lay on my bed before putting on my pjs and rolling around in the partially untied robe would give me a boner. It felt good just to let the opening of the robe and the belt slip around and across my boner. The damp fabric on my back and on my butt felt great too.

The second was my friend Anthony who started me on the "I'll Show You Mine" game. We did this a lot and soon other boys joined in when we hit 1st grade. We showed soft and boned up. I had a long cock then and now and other boys liked to get a look.

By age 7 I was consciously masturbating most every day. I would yank it out of the leg of my shorts and enjoy playing with it all over the place but where I really did it full on was doing it in my bed after school or at night. I would definitely finger my asshole as part of being butt naked in bed. I jerked it hard and VERY fast and definitely had orgasms, they were short peaks but I could have more than one. I would say three at least. If I didn't jerk hard my cock would go down fast if I stopped for any amount of time. Before age 11, I had to jerk fast to get it all the way up and off. It was around 11 and 12 that my hormones kicked in and that started the path to adult boners and coming.

I did jerk my cock with Anthony who was a bad, bad boy (another story!) but didn't really do it "for real" with other boys until around 11. Then I went on a binge with any boy in the neighborhood who wanted to do it. This lasted for about two years and included mutual hand jobs, butt crack humping, and some sucking.

Thanks for the series, I love reading this shit!"

  1. Dario

"I didn't know jack about jacking or sex or anything like that as a kid. I was an only child and my parents were real old so there was no talk about sex and I was real quiet so I didn't have the sort of friends that would do dirty stuff. I don't even remember hearing about any boys doing that. I was around 12 years when I found out about the sex part of being a boy.

What happened was I got hard in class; I guess it had happened to me before but not in school. I was adjusting it, and another boy was joking around about my "getting a boner" and he made enough of a deal about it that it got the teacher's attention. I was sent to the office and it became obvious to the principal (female) that I had no clue that "touching myself" was bad behavior. I got sent to the nurse and she gave me the basic facts about boys maturing and that erections happen. They didn't tell my parents so that was all the information I had until a few months later when they gave the boys and girls a separate talk and we (the boys) were told about wet dreams and ejaculation but not masturbation which many boys knew about already. I now got a clue what all the comments they were making were about.

Some personal information; I was physically larger than other kids, my dad was over 6' 4", but I was no athlete. I had some belly fat but was just "big boned." Which brings up (ha ha!) why the boy in class noticed my boner. My uncut penis and testicles were long. I didn't measure my cock until I was 13 but it was 4 inches soft and six hard back then (it's 5 and 7 and a half now). I was probably 5 inches at 12. I did pay more attention to getting a boner when I was at home after the nurse's talk and I played with it but I didn't do more than get it hard. I didn't know to do more until the sex class a few months later.

After that class I decided to try for "ejaculation" when I could be alone. I went home and took off my pants and socks and sat in my bed. I looked at my cock for a time and started rubbing it. I rubbed it like you wax a car, round and round. I got hard but nothing really exciting. I examined my nuts which were hanging. I did get to sliding my foreskin and that was exciting. I did this for some time but not long enough. I quit and gave up trying to ejaculate after trying this a few times. I was getting boners more and more and I got a few comments from other boys about how big it looked.

Finally, a boy that I was friendly with came over and showed me a stroke magazine that was making its way around. He said I could use it but he had to have it back so he hung around. We went to my bedroom and I did what I did before, got naked form the waist down. He saw my soft cock and said "wow" it was big, bigger than several other boys in our class. He didn't jerk with me (!) but went over to play with some of my cars and stuff out of my direct sight and I got on with trying for "ejaculation."

I looked at the magazine and it had men and women having sex. I saw a naked painted picture of a lady before but never saw a hairy naked pussy before. The guy was real hairy too. I had started to get pubes by this time above my cock but not on my balls. I rubbed my cock and got hard. I rubbed my body because of the pictures and got hot. Somehow I went to stroking the skin back and forward on my cock, I guess it was the pictures of fucking. I went into a dreamy state. I turned over on my chest and knees and stroked my cock like I was fucking. I could feel a tickling in my butt and balls. I got harder and more excited. I must've groaned a little because my friend asked if I was done. I said no.

I rolled over because I kept hitting my cock head on the bed and my neck was getting sore. I lay flat out and started stroking up and down on my cock. I was watching my hand jerking it. My legs twitched and my stomach tightened and relaxed. I rubbed myself with my other hand and then jammed it under my balls and squeezed my legs. Something was going to happen. I went "ah ah" and my asshole began clenching and I thought I was going to go to the bathroom on my bed for about a fraction of a second and then my cock jerked a few times and I got maybe one or two semi white drips on my cock and hand.

I jumped up, still worried about "having an accident" and clamping my ass tight. I looked down and saw the slimy stuff on my half naked cock head. My friend asked me if I was "done now" and I said "yes." I stood on my bed and pulled my foreskin all the way back and rubbed my ejaculation with my thumb testing the new feel of it. My friend came over and I was standing there with my cock hanging and he said again, "Wow! You've got a really big one." I got dressed and gave him his magazine. When he left I felt really relaxed and layed in my bed feeling good.

That was how I started and my first ejaculation. I didn't jerk with my friend but I did show my cock in the boys room to some of the other boys who asked to see it. I think this is where I started thinking about guys and showing my cock and jerking of in front of them. I ended up doing this when I got in my twenties and is still what I like doing, showing off and seeing other guys do it too."

  1. Mort

"My brother taught me. He was twelve and I was eleven, 14 months between us. We had a big house with a big basement area that was used to store stuff and we had a play area down there where we could be noisy and left alone. It was full of old stuff including an old couch/bed that was very sturdy. A few times Dave had told me to get out of the basement when I came down. I knew I interrupted him. He was on the bed.

Later I asked him what was going on. He told me he would let me in on a big secret but I couldn't tell mom or dad. I agreed, of course. He explained that about a year ago this guy named Miles that was in the Scouts with my brother had taught him about jacking off with moisturizer. Dave said he would teach me and he did by pulling his Scout shorts down and lying on the old bed.

My brother greased up his cock and started jacking. I never saw my brother with a boner before and he had gotten much bigger in the peter department. It was fat for sure. He had some pubes, red, we are both red heads. My brother jacked and told me what he was doing. His jacking made sloppy squishing sounds with each stroke. He talked less near the end and went real fast pausing a few times. He lost his grip once or twice he was jerking so fast. He made funny faces as he got near coming and I laughed and he told me to shut up. He came with his cock pointing up and I did see some thin jets of come.

He wiped on an old towel, we had cum rags down there for years. He told me to try and I got in position and started doing what my brother told me. I thought it was messy, didn't have pubes yet, but I put on too much moisturizer the first time. After I got hard it got more interesting. I didn't get the rhythm right the first time, too fast, but I did get to the point where I got a tension in my body and stopped. Dave told me to keep going and soon I had a quick trip to the moon and stars but no "blast off." I got to shooting come about a year later.

I did it a few more times with my brother but mostly just by myself or I got into jerking with a friend for a while when we were twelve. We did it at both of our houses and once we had another guy over for three of us. My brother and me both used the basement a lot up until about fourteen and the couch held up without squeaking and giving us away."

  1. Doug

"A boy one year older than me showed me how to jack when I was 12. I didn't know about it at all. We took off our clothes in a dump out in the woods full of old concrete pipes and junk. His cock was three times as big as mine and his balls hung down with hair. My balls hadn't even dropped yet. He showed me how and I copied him. I couldn't get my skin back all the way then. I watched him cum. A different time I sucked him under a bridge but he didn't cum in my mouth. I would done anything he wanted but that's all we did. I did suck another boy in a wrecked house a few times later on and eventually ate his cum."

  1. Brandon

"I can't remember when I started playing with it but it was before I made friends with Rusty in 6th grade. That's when I really got sexual about it. It wasn't long before Rusty introduced me to hand lotion in his rec room. We'd get naked and "cream up." We beat our hairless meat for quite a long time. I didn't get come and Rusty didn't too but we enjoyed the slippery delight of jacking our cut cocks and jacking each other. We were both on the chunky side of things and we'd rub on each other belly to belly standing up and lying on each other on the couch "crushing" each other with our full weight. We'd "fuck" which was sliding on the other guy and rubbing cocks and rubbing on each other's belly. Great times! I came a year later using hand cream jacking and rubbing on my hand in bed."

  1. DJ

"Name is DJ, I was 12 yrs old and had hit puberty early with a 5 inch dick and a good bush of hair starting to grow. I had heard my mates talk about wanking and had handled my hard-on a fair bit so assumed I was a 'bator like them. A mate gave me a Playboy from his Dad's stash for the weekend. My folks went out for dinner at the neighbours and left my bro and I to watch a movie. I snuck out a few times to flick through the magazine. I remember the pages were crumpled from my mate or his Dad's cum - but I didn't know that at this point. After a bit of fondling I started to play with my foreskin more and the sensation heightened. I found I couldn't pull my hand away and within a minute I started ejaculating. About 6 big spurts hit the bedspread and my legs quivered. I was panting and in shock. So THIS was masturbating I thought! Since then I've jerked off at least once a day."

  1. Cole

"First thing I recall? Going in my closet and sticking my hands down my pants front and back and feeling myself. Must've learned it from another boy, 8 then. I went in the closet not to be found out. Got real excited when I joined the swim team, 10 at the time. Had boners half the time wearing that nylon and seeing the other boys near naked. I saw other boners and I know the other boys saw mine. I got to rolling around and rubbing my cock in that suit in my bedroom, 7th heaven! A neighborhood high school boy lured me in to his car when I was 12. We was in his garage. I think he knew my nature. He asked if I played with it and said he'd show me the best way to do it. He got my pants open and jerked me stiff. Then he got his out! It was big and dark and his head was purple and shiny poking out. I was breathing hard I was so excited to see it. I knew what I was interested in right then. He felt me some more and I just about lost it. He quit then, I don't know why. I went home and jerked off and came thinking about it. Twice. That was my first jerk off for real. I never stopped since. I went after boys and they knew they could get me to suck them. It was good for a time then they got all scared of being called a homo for liking it. I still sucked some of them after, though."

All Rights Reserved. Copyright 2018.

Next: Chapter 12: Supplement 8


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