As a boy of 6 I stayed on my uncle's farm for the summer. His 2 daughters were older than me by 6 and 7 years. Being farm girls they knew about sex and loved to take me to the attic where spare featherbeds were kept. There we all got naked and on those big, fluffy mattresses they taught me the basics of sex. I remember my little penis getting hard, and how it felt good when they would ride it (without penetration). But they rode it so long it got sore and I insisted on playing a different game.
In spite of my childish lack of endurance and tolerance for pain, they woke me up to the fact that there was fun to be had with that little tool. On returning to the city, I was always trying to find something I could use to reproduce those good feelings with the girls. But it never occurred to me to try holding my penis with my fingers -- until one day when I was playing army in an empty lot across the street from our house. I was playing in a crater where a stump had been pulled out. An older boy cutting through the lot saw me. He came over and we talked for a few minutes, and then he asked if I was "playing with it." I said no. He asked if I knew how, and I said no. He then asked if I wanted to learn how. "You bet!" I said. So he hunkered down in that crater with me, unbuttoned his pants, and took out what I thought was a big one. He didn't have to ask -- I just reached for it, and it felt great. He asked me to take mine out, too, and I did without blinking an eye. We played with each other for some time before he (probably) had an orgasm -- I don't recall it, but then I wasn't looking for it because I was so amazed and pleased with that new knowledge. I never saw him again, but I've always thanked him in my mind for showing me how to please myself and satisfy that undefined yearning I'd been having. And for doing it so nicely, without any bullying tactics.
Of course, at that tender age I didn't ejaculate, nor did I get "that feeling" that later would become so big an element in my life. It just felt really, really good to stroke the little guy with thumb and forefinger (not yet big enough for a hand). I did notice, though, that HIS hand felt so hot and "special" on my penis, whereas my hand, though it felt good, didn't produce the same intense feeling. I've since learned (as most of us do) that there's always something "electric" about the touch of another person on our bodies.
With this new knowledge, in the next 4 years or so I masturbated 3 or 4 times a week, sometimes more, without ejaculation or orgasm. Then one beautiful spring day, I and some classmates were walking home from school. As we passed a street-sign post, I jumped up and grabbed it, locked my legs around it, and slid to the ground. I'd done that lots of times before, but apparently I was ready for this one -- I got the most delicious, warm, and wonderful feeling I'd ever had. It was just heaven. I clung to that steel pole as if it were the most wonderful thing in the world. I didn't connect that with masturbating and didn't realize until years later what had happened. But that was my first orgasm, with a steel pole as a partner. Still no ejaculation. Even though I didn't know what had happened, I'll bet I climbed that pole and slid down it 500 times after that trying for the same feeling, which I never was able to produce again.
A couple weeks later I finally got up nerve enough to tell 2 of my buddies what had happened on that pole, and it turned out they were already masturbating. They took me to a deserted old house with lots of high weeds in back, where we each masturbated ourselves and each other. I was spending lots of extra-long times in the bathroom at home playing with it. I was learning how to "get that feeling" more dependably.
It was in that bathroom when one day as I brought myself to orgasm I also ejaculated, thick and creamy. I'd heard about "wads" from the guys, but I wasn't quite sure what it was. But I DID realize it felt much better than having dry orgasms, so it was fine with me. I didn't like the mess, but since I was in the bathroom anyway, toilet paper solved that problem. Soon I learned from an older kid all about ejaculation and semen, and from then on "shooting" or "squirting" became a regular goal of my masturbation sessions -- which increased to 2 to 4 times a day most days.
My life continued, with masturbation a regular part of most days. Oh, I was always still interested in girls and shared sexual experiences with several, from limited playing to full penetration and orgasm. Still, that was infrequent, unfortunately. But I could always depend on masturbation: It felt great, I could do it as often as I wanted, and no one ever knew. I was fortunate, I guess, in that my older brothers were off fighting the war, and although our mom certain knew what was going on, she never made an issue out of it (having probably learned from my older brothers). So I never experienced being walked in on by someone. Occasionally, a neighbor boy and I masturbated together. He was about 6 years older than me, and his penis was beautiful and large and I admired it a great deal.
About this time I entered Catholic school, where I received the gift of guilt from the Church about almost everything -- but certainly about "playing with oneself." It took me many years to work through that guilt and enjoy my body without fear of purgatory, hell, or eternal damnation. Now I often wonder just how we could possibly have been so gullible as to accept the idea that it's a sin to enjoy your body. But many of us did, and probably still do. My advice: Lose those notions. They're phony from the jump.
Guilt didn't keep me from playing with myself, and sometimes with a friend. My good friend at that school (we'll call him Bobby) and I masturbated ourselves together and each other. A funny story: The first time I went to confession, he was outside in a line of girls and boys from school, waiting their turn to confess. I confessed to the priest that "I touched myself in private places about 16 times" in the week. I can't remember for sure, but I probably had to say about 20 rosaries for that. When I came out of the confessional, I noticed that every eye was on me. Bobby whispered to me that everyone had heard clearly what I said. Several of the girls were giggling about it, so I was pretty embarrassed. But the experience served as a great fantasy during several masturbation sessions. Imagine! So many cute little girls (and boys) had heard what a champion young masturbator I was! And no doubt some of them remembered me and my confession when they next played with themselves. I even considered becoming a priest so I could hear girls and boys confess to playing with themselves.
Through high school I continued masturbating regularly, sometimes to excess no doubt. Until then I was uncircumcised, and I enjoyed the foreskin feeling. But after high school, for religious reasons and to be more like the other guys in the showers, I had myself circumcised (by a doctor, of course). To me, it has made no difference in the intensity or frequency of orgasm, nor how long I have to stroke to reach climax. Yes, there is a slightly different feel to masturbation, cut and uncut. No big deal to me.
Through many affairs with women and three marriages, I continued to masturbate AND have regular intercourse. One didn't interfere with the other, perhaps because I was strongly sexed and never really seemed to get enough. I had learned to like sex books (now called "adult" books) because in their exaggeration, they helped my fantasies. Through my middle 40s I was still masturbating several times a week, sometimes 2 to 4 times a day when I was "in heat." Oddly, I never shared my masturbating habit with any of my ladies, much to my regret now that I know how so many of them enjoy the same things we guys do. I still had feelings of guilt, I guess, and thought the "sugar 'n' spice" ladies wouldn't approve. Shoulda known betta, right? Right!
A few times in those years, I'd decide to quit (usually trying to get "right" with my religion). Never worked, of course. But I remember one time I had quit and was doing things like praying and cold-showering to stay away from it. Then, on a trip one day, as I drove across an overpass I looked down and saw several brightly colored books scattered on the side road below the overpass. I just knew these were porno novels, and ALL my old urges returned at once. I turned around, came back to investigate, and -- sure enough -- there were about 15 porno novels someone had tossed, probably cleaning out their car before getting back home to the spouse. That was the last of quitting. My first orgasm, after about a month of abstinence, was especially excellent. That day and the next, I must have brought myself off at least twice for each of those novels. God! It felt great to be back in business, and I've never felt guilty or tried to quit since.
After my last wife and I were divorced, I discovered adult arcades, where you could go and watch one or more sex flicks -- and in the little private room you could masturbate to your heart's content. That was something different. Then, holes began to appear in some of these private rooms, reamed out to the appropriate size and at the right height for insertion of a penis. And guys sometimes openly invited you to let them fondle your penis, or more. I did meet a couple of guys in that environment with whom I shared mutual masturbation -- one remained a friend for a long time. There was always an intense excitement when another hand stroked me.
Now, at nearly 60 with no wife, I still masturbate regularly. No longer 2 or 3 times a day, but now 3 to five 5 a week. In the morning or evening I'm now able to spend the time it takes to raise my desire level so that orgasms are more intense and delicious. I sometimes use lube (like Wet Platinum, costly at adult stores but great), and sometimes I prefer the dry, unaided hand. I've tried most possible variations, but I still have only 2 favorites: (1) regular hand grip, usually dry, and (2) the reverse grip with thumbs down, lots of lube, and letting the entire shaft and head slide through the sleeve made by the hand. Very erotic and satisfying.
Occasionally I'll use a sex toy to simulate intercourse. Most adult stores sell flexible rubber (or vinyl) penises that are hollow inside. These are made for ladies to insert vibrators into. However, I find that my erect penis fits snugly inside these. So I get an erection, lube the inside well, and slip it over my penis, expelling the air caught inside so there's a kind of vacuum grip. Then I either simulate intercourse or just masturbate. To simulate intercourse, I lie on my stomach on 1 or 2 pillows, hold the bottom pillow as if it were a woman's bottom, and pump in and out just as I would in intercourse. This usually produces the best climax because the muscles around the lower lumbar and groin are tensed and released, as in intercourse. Such movement is a big component of the best orgasms. Here, that is combined with the pressure of the bottom of the rubber penis on the highly erotic area at the base of your own penis, simulating the pressure of the mons pubis against a woman's mons veneris during intercourse. Yum.
The second way, masturbating by hand, is done by inserting myself into the well-lubed rubber penis. This not only feels great, but there's a special visual excitement, too. The rubber penises are well designed and look very real. Since you're inside it, it adds about 1/16 of an inch in every direction all around your own, and LOOKS as if you've got a bigger penis -- always something of a turn-off for me. Be careful you don't "fall in love" with the odor of rubber or vinyl, however, or condition yourself only to climax when you sense that odor. No joke, it can happen. But not to worry, just vary your style and you shouldn't have any problems.