Early Masturbation Experiences (and some later ones too)

Early Masturbation Experiences (and some later ones too) When I was very young, my best buddy was a kid named Denny. We were inseparable. We knew nothing about sex or jacking off. One day as the two of us were leaving school, an older kid who was probably 14 or so beckoned to us and said he had something to show us. He led us back into some dense shrubbery quite near the school grounds. He unzipped his pants and took out his penis and started masturbating. He encouraged us to follow suit. First of all, I was totally shocked by this kid’s actions. I had never even seen anybody’s penis but mine. Plus, I wasn’t about to expose my own dick in front of this kid or Denny. And I am sure Denny felt the same way. Denny and I just stood there transfixed on what the kid was doing. Neither of us knew anything about jerking off. Within a fairly short time the kid ejaculated a few streams of semen. This was even more shocking to Denny and me. After shaking the cum off of his dick, the kid zipped up and walked away. I was so shocked about what I had just witnessed that I didn’t know what to say. So, I said nothing. And neither did Denny. We never discussed it.  A couple of years later after my family had moved from the Midwest to the East coast, I discovered the joys of masturbation on my own but at the time did not realize what it was and in no way connected it to what the kid did when he masturbated for Denny and me in the bushes.  The school I attended had large swing sets supported by fairly tall A-frames constructed of steel tubing. The tubing was about four inches in diameter. It was common for us boys to shinny up these support poles. I discovered that I could wrap my legs around the pole so the bottom of my penis was pressed against the pole. After some practice I learned that hunching up the pole, and slipping back a bit, then hunching and slipping back, felt incredible on my dick. After a few minutes of this up and down motion on the pole, I got an incredible feeling…which of course was my first orgasm. It was dry because I wasn’t old enough for an ejaculation. At the time I thought I was the only person in the world who knew about this. And every day at recess I was out there on one of the poles giving myself an orgasm. I am shocked that none of the teachers ever said anything to me. It had to be incredibly obvious what I was doing.  My pole masturbation came to an embarrassing end when I overdid it one day and managed to somehow tear my foreskin. It hurt like hell and then I felt wetness in my pants which turned out to be blood. I only lived a couple of blocks from the school. I told the recess teacher I had an emergency and had to go home and took off running. By the time I got home my dick had stopped bleeding. I washed up the bloodstains on my crotch, changed to clean underwear and threw away the bloody pair. And went back to school. I was afraid to do any more pole hunching for fear of further damaging my goods.  I honestly don’t remember how I eventually learned how to masturbate myself the conventional way. And I don’t remember my first cumshot either. But I do vividly remember the next time I saw another person masturbate and shoot his cum. I was about 14 at the time and a member of a boy scout troop. We were on an overnight hike on the Appalachian Trail. On the overnight stop there was a lean-to built along the trail. There was room for about five or six of us under the lean-to and the rest of the troop pitched tents in the campground. I was one of the scouts in the lean-to. Our Junior Assistant Scoutmaster was also in the lean-to. I am guessing he was 19 or 20 while the rest of us were 13 or 14.  After the talk had died down and we are all about to go to sleep, the Assistant Scoutmaster called out “Look at this.” He turned on a flashlight and shined it on his cock that was being masturbated by his other hand. His cock seemed to be huge. After just a couple of strokes he started cumming. I remember that his cum seemed much thicker and more voluminous than any of my own cumshots. He didn’t shoot but it just kind of poured out of the tip of his reddening cock. It just kept oozing out and running down over his hand. It reminded me of oatmeal except it was white. After he finished, he turned off the flashlight. Nobody said a word. I don’t know how he cleaned up because there was a lot of cum and it was pitch dark so I couldn’t see what he did. We all went to sleep and the next morning not one single word was said about it by any of the scouts. At least not that I heard. My dad was the scoutmaster of our troop at the time and I knew I should tell him what the guy did but could never work up the courage to do so. I only had one other sexual experience as a young teen. And it was pretty tame. At the time a neighbor kid named Donny was my best friend. My previous friend Denny was left behind in the Midwest when my family moved to the East. Anyway, Donny and I had what we called a “club” with us as the only members. Donny and I were probably 14 when this occurred. There was another younger neighbor kid who used to hang around us and he constantly bugged us to let him join our “club.” So, one day Donny told him he could join but he had to suck our dicks first. This really kind of shocked me because Donny and I had had very little conversation about anything related to sex. After much negotiation the kid agreed to suck each of our dicks for 30 seconds. I really wasn’t very keen about the idea because I was always very shy about showing my dick to anybody. I don’t believe that anybody other than my parents had ever seen it at that point. Maybe a doctor.  I happened to have a stopwatch that we were going to use to time the length of the blowjob. We flipped a coin to see who would go first and I won. So, I took my dick out of my pants. I’m not sure it was even very hard. Maybe semi-hard. The kid put it in his mouth and just held it there while the seconds clicked off. He didn’t suck, just held my cock stationary in his mouth. It really didn’t feel like anything and wasn’t remotely exciting. After the 30 seconds was up, the kid moved over to Donny. Donny already had his cock out and it was fully hard. He had been masturbating while the kid took his turn on me. The kid slipped his lips over Donny’s distended prick and proceeded to just hold it there. Donny moved his hips back and forth but frankly I could tell that there was nothing about it that was very arousing. After the 30 seconds was up, that was the extent of it. Again, there was no conversation between us and the three of us went on about our business as if nothing special had taken place.  It was legal to drive at 15 in the state where I lived, and I got an old car that I bought for $75. But before I got the car, I got around quite well on my bicycle. By now I had a girlfriend. I can’t remember the specifics but for some reason, I ended up spending the night at her family’s house. It may have been too late to ride my bike home. I was sleeping on the sofa in the living room. From where I was situated, I could see the staircase leading to the second floor. Shortly after waking up as I lay there, my girlfriend’s dad came down the stairs. He was only wearing boxers and a t-shirt. However, his entire cock and balls were outside the boxers and flopping from side to side as he came down the stairs. He had an unusually large penis, at least to my 15-year old eyes. Nothing ever came of it and to this day I always wondered what the hell that was all about? For the short period of time I dated his daughter, I never felt that he approved of me so why would he expose himself to me? Once I got my car, I got very serious about dating. I was quite successful from a sexual standpoint with a number of high school girls but for whatever reason, masturbation was never part of my plan. Which upon reflection, was probably a big mistake. My goal was always to get my dates to fuck. While quite a few of my dates were compliant, many weren’t. If I had been smart at the time, a nice handjob would have likely been a successful fallback position. It was only much later in life that I learned that a handjob was a nice alternative.  After my second marriage bit the dust, I hooked up with a sexy little gal who was more of a fuckbuddy than a serious relationship. While we did everything under the sun from a sexual standpoint, she loved to jack me off. She also got a huge kick out of watching me jack off. Prior to one of our dates, I would edge for a couple of days so that once she and I got down to business, I could deliver a major cumshot. She really loved to see me shoot. She was so into it that a couple of times the crazy little gal would get out a tape measure and measure how far across the floor I would shoot my streams of cum. My all-time record was just an inch short of 5-feet.  Around this same time, I organized a couple of circle jerks. Several with just guys and even one where a girlfriend participated and jerked off each of the guys in attendance. That was really hot. I also participated in several one-on-one sessions where the two of us jerked each other off. I remember one of those where I jerked off my partner but then instead of him jerking me off, I did myself but sprayed my cumshot all over his cock and balls. A real turn-on.  My early shyness about showing my cock is a real thing of the past. Now in any group setting, I am always the first to unzip my pants and get my hard dick out on display.  ##################