Although I probably had a hand around my fetal penis, I didn't masturbate to orgasm until I was about 14. A kid in the 8th grade lunchroom said something about "whacking off" and made a circle with his thumb and index finger. Up and down he gestured. I waited until a quiet Sunday afternoon when nobody was home. At that time I was still small enough to fit into an old canvas laundry bag, and I wore it over my naked body. The feel of the material stimulated me. With a book in one hand and my penis in the other, I manipulated my penis, as the dictionary defined "masturbation," and felt it growing and getting harder with each stroke. The book had nothing sexual in it: I had been in the habit of lying in bed and pulling my scrotum up and around my penis so it slowly reopened like a bud. I had been circumcised according to Jewish tradition, but years of prepubescent pulling and stretching, almost automatically, only half-consciously, provided me some foreskin on my penis.
The pleasurable sensation intensified, and I finally ejaculated — that is, a milky-white liquid began flowing out onto the canvas. I was so naive I wondered if I had harmed myself somehow, so I waited an entire week before masturbating again.
Soon, though, I was masturbating usually once or twice a day onto a face towel I kept under my pillow, or into a toilet. Around the same time, I began practicing yoga. Because my mother habitually opened my bedroom door as she knocked, I had purchased and installed a door lock. After a few nights of exercising in shorts, I realized there was no reason not to be naked. In the "plow" position — legs thrown over my head and stretched out behind — my penis hung over my face. I had read of Tantalus and the grapes in mythology, and here was a big bunch so near my mouth. I must mention that very soon after starting to masturbate regularly, I started tasting my own "pre-cum" and semen, collecting it, masturbating onto my windowsill when it was covered in snow, and masturbating almost anywhere I could. So it occurred to me to stretch a bit further and try to reach the tip of my instantly and demandingly erect penis with my tongue. I remembered my breathing and pulled myself down as I exhaled. The first time I tried, I couldn't quite reach; I squeezed the "pre-cum" all the way up the shaft so there was a big drop at the head, picked it up with a fingertip, and savored the salty, viscous taste and texture.
My bed had a frame with arches at the foot. My feet fit easily into them as I flipped over again. A bit more breathing and stretching, and voila! My tongue touched the tip. I could feel the "pre-cum" oozing onto my tongue and the opening of the head. Electricity zapped through my entire body. I had to lie down and catch my breath, but very soon I was masturbating to the point of orgasm, flipping over, and ejaculating into my mouth. I could pull the foreskin down over the tip enough to either insert my tongue into the space or hold it in my teeth. I never broke the skin, but when it returned to its regular state, I could see teeth marks about 2" down from the tip.
I never actually ejaculated just from sucking my own penis, although on numerous time, I came very close. I always got so excited by the prospect of ejaculating right into my mouth that I just rubbed myself to climax. Before long I had one or two fingers up my rectum and found my prostate, making each climax even more pleasurable than the one before.
I am mostly left-handed, but I learned to masturbate with my right hand after a fall left me with a cast on my left wrist in the muggy Long Island Summer. One memorable morning I was in the bottom bunk on a group trip to Expo 67 in Montreal with the YMHA daycamp. I arose with the sun and started working my penis, which, in addition to measuring almost 7" from the base, had become thick. Eventually I grew to 6.5" x 7.5", and my testicles became the size of small eggs. So here I was stroking myself under the sheets, pantsless (having taken them off under the covers the night before), when one of the counselors — a handsome, young, hairy, bearded man who was completely nude — saw me awake and walked over to tell me I could go back to sleep for a while longer. I don't know if he knew what I was doing, but I finished off in the bathroom later while wishing I had shared my dilemma and perhaps found some assistance. That's a fantasy I still replay, even now at age 48.
In college I was "caught" masturbating in the dorm room by almost every roommate I had. If they seemed to be sleeping, I would uncover my penis, since it felt more comfortable having it sticking straight up. Two of my roomies even accused me in front of some women friends of being a "compulsive masturbator." But I was just an exhibitionist and enjoyed showing off to an appreciative audience. When my one gay friend returned from a trick, he complained that the guy wanted to masturbate, as if being with another man meant you only engaged in interconnected sexual activity. Had it been me, we would both have had a great time. I masturbated at my friends' houses, inside and out (wandering my neighborhood in the middle of the night and masturbating outside their windows), in line for a concert at college with a long parka while standing in the midst of a crowd, and more and more places as I went on.
In the sex I enjoyed with men, masturbation always played an important part. During the summer of 1973, in San Francisco, a man about my age then (20) was able to bring me to an orgasm. Perhaps it was the presence of our supposedly sleeping friend in whose apartment the act occurred. In any case, many men tried very diligently to get me off, but the touch I needed was almost always ultimately my own. So I usually have to finish the job.
While in San Francisco I found J.O. parties and gave my first completed handjob. I always feel proud and pleased when I can bring a buddy to orgasm. Group sex was fun because I was among voyeurs and exhibitionists, and some who were both. When I was taken to Land's End, Devil's Slide, and San Gregorio Beaches outside of S.F., I reveled in the opportunity to feel the sun, smell the ocean, and see the sky and the water as I masturbated — onto my hand or just anywhere the semen flew. There were group scenes, but as often as not I just wanted to masturbate in the outdoors, and I didn't care if I was alone.
Being watched was fun. When I lived on Castro Street, my windows overlooked the street. I sometimes dared display myself naked in the daytime and occasionally had the viewer stop in for some fun. At night there was a man in a raincoat who always walked his dog about midnight, and he'd stop and watch me masturbate to an orgasm and eat it. He never as much as touched himself, but I know he replayed the images when he was safely alone in bed.
On another memorable occasion, I had returned horny and frustrated from a party. I was soon out of my clothes, stretching and then standing in the window, bending over and licking my glans, when out of the corner of my eye I spied a police car. Heart pounding, I ducked behind the drape, but peeking out I could see that the car was pulling into the driveway next door. A tall, curly-haired cop with blue tinted glasses burst into the flat. He pointed to a space behind the door and said something about "getting my nut," and I meekly pulled on some overalls as the cop told me he was taking me downtown. Then his partner, who was totally uninvolved, heard a call for a real crime, so they both left. I let my heartbeat slow down then got even harder realizing what a revolutionary sexual act I had performed. Whether he was closeted or whatever, the cop was going to see pictures of me brazenly bending over and displaying my ability to suck my own penis, in his dreams and his fantasies, for the rest of his life.
I have had two long-term relationships, and masturbation was a part of both of them. Unfortunately I lost both of my partners to AIDS and have spent much time alone. In recent years I have been using genital rings, nipple clamps, dildoes, shoestrings, leather straps, wide rubber bands, etc., to enrich the masturbatory experience. Photographs and videos of myself and of other men masturbating and/or having other kinds of sex are a good addition to a session. When I have the time, I can go on for several hours. I generally stop and start, especially nowadays when I am looking at pictures on the Net.
Since 1986 I have met other men whose natural preference is for masturbation first and foremost. In the throes of relationship difficulties several years ago, I stopped self-sucking and lost the required flexibility. I still eat my semen most of the time when I masturbate at home. I am overweight, but I still entertain the idea of getting back to self-suck shape. My fantasy has been to find a younger self-sucker to coach me and practice with me.
Women play a part in my masturbation fantasies. My actual experiences have been few and far away, so the scenarios I have developed get me extra excited. I would like the opportunity to masturbate a woman to orgasm and see if a woman could get me off that way.
I'll leave off now. There's probably a nice big drop of "pre-cum" waiting to be milked out, since I have been using both hands for typing. At this point and with some Tantric education, it isn't necessary for me to achieve an ejaculation every time, but I do need to exercise my most well-developed muscle on a regular basis. I switch hands, sometimes use "grease" like Alboline, or just stretch the foreskin up and down as I stroke. Masturbation is a gift of pleasure in a world of pain. The good Lord, gods/goddesses — whatever — have provided every one of us from time immemorial the ability to make ourselves feel really good just about anytime and anyplace. As I sit here typing, men and women throughout the world are pleasuring themselves, for the first time, for the last time, for uncounted times and years, alone, one on one, in groups, in public, and private.
My mantra: I love to masturbate. I live to masturbate. Masturbation is my life.