(Some of the names have been changed for privacy.)
I have enjoyed masturbation from puberty onward. It has been a sexual outlet for me when I have not been involved with a girlfriend or wife. My wife once challenged me that I could probably remember all my masturbation episodes but not more significant events in my life. She was probably right. Unlike some of the other correspondents, I did not grow up with guilt about self-pleasuring. I got the idea early on that it was OK. It was a private activity for me although no one told me specifically that it was.
I grew up during the 1970's in the suburbs of Washington when many books about sex appeared. These fueled my erotic imagination. David Hamilton photography collections featuring nude girls were also arousing of course.
The first sex book I read was 'Everything You Always Wanted to Know About Sex...But Were Afraid to Ask' which my father acquired as a gift from my teenage brother at the time. I was 10 or 11. The only question I asked was what was masturbation. My father described it as 'pocket pool'. I knew that as playing with one's pee-pee, which I often did through my pocket, not to achieve any particular pleasurable feelings, but simply because it was there to fondle. I remember once 'playing pocket pool' while talking with Dad and Mom, and my mother, seeing what I was doing, grabbed at my hand in my pocket with a smirking, 'What are you doing?' That was embarrassing; her intent may simply have been to make fun of me or to not touch myself so obviously in public. I have probably repressed this memory since then, but that episode taught me (or embarrassed me) not to do it in public. To the limited extent that I have discussed sex with my parents, I have been more open with my father and got more information and ideas from him. He gave me the biology lecture, but the mechanics of sex I mostly learned later from the books I perused and became aroused from in the libraries and book stores. Luckily they carried The Joy of Sex.
From my father I learned that masturbation, or 'doing it oneself,' was an outlet when in the Navy and away from his wife and as a way to avoid visiting brothels. Wet dreams were described as 'messy'.
From fourth grade on I attended a boys school. The experiences of me and my classmates need to be described in the first person singular only. I leave it to others to generalize about us, but this school must have had a profound effect on the psyches of all of us. I know I would have been a different person had I gone elsewhere. Sexually, I don't know. In an all-male milieu, of course there were homosexuals, perverts, celibates, and misogynists. I think there was a strong streak of homophobic paranoia which made us fear being labeled as one. I learned much later that one teacher was a molester and another may have been. The troubles of some of my classmates may have been his fault.
I was probably naïve and ignorant of much of what may have gone on with my classmates, male and female. Unlike the English public schools, most of my classmates were not boarders. In the early years, others were more knowledgeable about sex than I, probably because of older siblings who were more open about sex than was my brother. I knew of no group or mutual masturbation or homosexual activities among my fellows.
I formed only a few very close friendships, but these never entered the sexual realm. One of these friends referred to doing it (touching oneself) in the bathroom but that was the extent of personal sexual revelations by either of us.
Prior to puberty at 13, I was aware of arousal feelings, but these did not seem to focused in my penis, rather a sinking feeling in my belly and an urge to relieve my bowels. The summer when I was 13, I had my first strong erection. My family had recently returned from a trip to Japan. There, I had been fascinated by the open display of topless nudity on postcards of pearl divers. I was still sleeping in my underwear, but at our summer house it was a hot night and I pulled off my briefs late at night. What a novel sensation, to sleep nude. I had urges to go to the bathroom, but the feelings were not relieved. I remained sleepless. While trying to stick my erection in between the mattress and box spring, I fantasized about 'sticking my dick' into the 'pussy' of the girl with whom I had had my first date.
At puberty (at 13), I had wet dreams. I cannot remember if they followed or preceded the incident above. I probably wished that I could control my ejaculations because of the resultant mess. (I now regret considering them messy because I would enjoy my ejaculate more.) I do not remember how or when I began stroking myself to orgasm, but it probably began with the following incident.
I was relaxing in bed, lying on my left side. My pajama trousers must have been pulled down to expose a nice erection. I was gently running the tip of my right middle finger along the underside of the shaft and on that very sensitive area below the frenum, when all of a sudden I came with a spurt of a white, grainy fluid. Instead of glorifying in my first come, I cleaned up and went to sleep.
An early method that avoided ejaculation was to bend my semi-erect penis down between my thighs and squeeze them while tensing and stretching my legs and toes. This squeeze method was arousing in itself, or I would stroke myself and use the squeeze to bring myself to orgasm. After coming, I would hold the squeeze to keep the semen from spilling out until that urge subsided or until I could ejaculate into an old sock or tissues. This way was good while in bed and helped me to fall asleep.
My subsequent masturbations occurred during showers. I probably began by sliding my soapy hand along an incipient erection, which made it harder. As I stroked harder and faster and approached orgasm, I rose up on my toes and let my back arch and then came powerfully, with my come spurting high and far. In the shower one could wash away the evidence. No one ever challenged me about the length of my showers. I especially loved how my cock became a deep red with the stroking and how white the cum looked on the head. I generally did not continue stroking long after I came because my cock head became so sensitive.
Outside the shower, masturbation was cock in hand with saliva and pre-cum as lubrication. I sometimes watched myself in a mirror. I used pieces of a plastic garment bag to add to the sensation. To elaborate: While others enjoy friction, I enjoy lubrication, so any method to prolong the slippery feeling prolongs the pleasure. I would enfold my lubed erection in a piece of plastic from a dry cleaning bag to duplicate the sensation of either a vagina or a foreskin. This plastic also functioned as a condom to collect my cum for tasting or for subsequent use as an instant lube.
Concerning positions, I was usually on my back. I would also stand to watch myself in a mirror. Sometimes I knelt, but this became tiring later on. I remember supporting myself in missionary position and trying to slide my penis head along the plastic piece using pre-cum as lubricant. My attempts to masturbate in missionary position were unsuccessful; I needed a way to directly stimulate my cock
A very successful way to achieve direct stimulation was to simulate doggie style by kneeling next to the bed and inserting my cock in between mattress and box spring into a lubricated plastic bag. Advantages: leaning forward onto the bed squeezed the cock more, I could read erotica, and I was thrusting, which was great stimulation.
Let me differentiate stroking from sliding to describe exactly how my hands and fingers stimulated my penis. Both methods are very stimulating, of course. Grasping the shaft and moving my hand or fingers such that the flesh moved with them and my hand was not moving along the shaft can be called stroking. Stroking with two fingers on the frenum and the thumb on the upper side of the shaft, first slowly then faster, could bring me to a quick come. This method could easily lead to the following method.
Moving my hand along the shaft is sliding, which has been a great way to masturbate, especially with lubrication. In the shower soap or saliva were the usual lubricants. In bed, saliva, pre-cum, and other manufactured lubes have been my preferred lubes. A lubricated plastic bag slipped over my cock like a condom allowed my hands to slide more easily. This was very stimulating, plus the bag caught my come. From now on I'll call both methods stroking.
As for hand and finger positions while stroking, these were my variations: grasping the shaft in the fist usually with my right hand, grasping the base with one hand and sliding my fingers of the other hand over the head, playing with the pre-cum on the head with thumb or fingers, sliding a finger over the frenum.
Two handed sliding, first one hand up the cock, then the other, and repeating this action faster and faster, can get me very aroused. One time as I was doing this in the shower with soapy hands, I leaned over and began to breathe heavily. Then I just had to come by arching the back to thrust out my cock, rising up on my toes for more muscular tension, and continue sliding the hands one after the other over the head, or thrusting until I came. Whew! It's great when you just lose yourself in the act of masturbation and bring yourself to orgasm! (I loved writing that sentence!)
So those were my basic methods from teenage years onward. Early on I became curious about my anus and realized that it was the source of pleasurable feelings also. This probably began with a desire to be clean there which led to exploration by slipping my finger inside, and later my thumb. Then I discovered that shoving my thumb into my anus while stroking my cock led to very powerful orgasms. Wow! I also explored with inserting slender objects. I had a small dowel and a cigar tube (who knows how I had this) with which I experimented by inserting either into my anus.
This reminds me of my technique for cumming into my mouth. I lay on my back, head towards foot of bed, hips on pillow, legs stretched up the wall behind my bed. I would grasp the end of the mattress to pull my torso closer to the wall while 'walking' my heels up the wall until my shoulders, neck and head were supporting my weight and a pillow was (sort of) supporting my back. I was stretched up along the wall. Then I would bring myself to a quick cum by squeezing my balls between my thighs and stroking my shaft, frenum, and head of my cock. I tried to aim my initial spurt of cum and subsequent drips onto my tongue and mouth. The taste was astringent or sour, but warm.
Another method was to throw my legs back over my head and aim my cock towards my mouth. the 'spurting distance' was shorter. These methods are hard on the neck, needless to say.
As for masturbation places, summertime circumstances allowed for some adventure. After obtaining my driver's license, I was expected to find summer work. Fortunately my family had a summer place near a beach resort. Our house was in a new resort community nearby. This house had a large, enclosed outdoor shower which afforded me many opportunities to shoot my cum during a long shower after work. Although the shower was big enough for three, I did not share it until my wife came along. Circumstances were such that during those summers, only my grandmother and I were at the house. On one of my days off, I drove to a secluded area, stripped, cavorted around naked, and (probably) masturbated. On that occasion I had bought my first copy of an adult magazine, which featured a photospread of the actress who played Nancy Drew back in the '70's. Once I motored our small sailboat out into the nearby river, brought out my erection from my gym shorts (thus I was not naked; I also omitted underwear) and stroked myself (with saliva and pre-cum as lube) until ejaculating into a paper towel. It was a weekday, so there was no boat traffic. One night I snuck outside under the hot summer moonlight and slipped off the same blue gym shorts, and sat/lay on the rough grass next to a sweet gum tree in the front yard. I again stroked myself with saliva and pre-cum until my warm, slick cum coated my cock. My gym shorts retained a small white stain for years afterward. But the mosquitoes were murder. During those summers my erect cock curved upward and was very stiff. It was a wonderful time to masturbate. I was probably doing it every day.
More to cum, er, come!