My masturbation history begins when my penis was circumcised. I realize this is an unusual place to begin the tale, but both my technique and the way I learned to masturbate hinge on my circumcision. I've also finally come to appreciate the solo joys of having been cut.
Fast-forwarding a little, I didn't actually know my penis had been cut until a number of years after it happened. My best friend was over at my house, and we were on our way outside. We both needed to pee, though. To 'save time' he suggested that we have what he called a crossfire: basically, since we should both be able to hit the toilet at the same time, we could pee at the same time. I suppose we did save time urinating, but we ended up spending more time than what we'd saved comparing our penises. As soon as he got his out, I realized it was different from mine. From what I could see, it had no head. There was just a long tunnel of loose skin over the whole thing that ended in a narrow hole. I asked him what it was, and he told me I'd been circumcised-that I'd been born with a skin like that, but that it had been cut off. By way of demonstrating, he slid his foreskin back and showed me his penis had a head just like mine, only lighter pink and glistening wet. I don't remember much sexual excitement at the time, but I've been fascinated with the modification made to my genitals ever since.
I first discovered my penis as a source of pleasure a little while after that. I was watching a video while lying down and (I assume) absent-mindedly fondling my dick, when my head suddenly started to tingle. Before I knew what was happening, a wave of pleasure surged through my penis, starting in the head and flowing down through the whole organ. I wasn't really an orgasm-just sensual pleasure, not full sexual release-but it was so intense I had to stop touching myself.
It had felt amazing; the only problem was that I didn't really know what I'd done to make my penis feel that way. My circumcision left my head bare, smooth, sensitive and completely unprotected. Effectively, it was getting stimulated all the time from brushing against my underwear, etc. How was I to know exactly what had done the trick? Long story short, I spent as much time alone with my penis as I could over the next couple days, trying to make it feel that way again. That led to my first masturbation technique: first, I would fondle myself into an erection (not hard with perpetually horny, pre-orgasmic genitals), then rub my smooth, dry head back and forth across the inside of my thigh. I don't think I ever actually got off that way, but I could get to the intense pleasure that made touching my penis any more too joyful to bear.
The problem was friction, and the short reload time that went with not really having orgasms yet. One day, a few months after I started masturbating, I did it so many times in a row (five, I think) that a little spot on my head actually bled and scabbed afterwords. (At age 29, I still have a small scar from it.) I decided I needed a new method. Back to experimenting with my penis. Soon, I devised my current main technique: rolling my remaining foreskin back and forth over the rim of my head, held between thumb and fingertips, with my hand held so it gently brushes the side of my head. I have a loose circumcision, and spent my teens stretching the skin I have left by masturbating with it, so my skin slides back and forth very easily. The doctor that took a scalpel to my penis was kind enough to leave me with a lot of very sensitive, pink inner skin between my purple-ish head and my dark brown scar. Even trimmed and dry, the feeling of my remnant inner foreskin rolling back and forth over the back rim of my head-well, let's just say it helped.
I don't really remember the first time I got off. Actually, I'm mostly just unsure where to draw the line between pre-orgasmic pleasure and my first dry orgasm. It was sometime soon after I changed methods, though, that things started feeling different. The pleasure that would course through my cock at the end was always intense and wonderful, but it gradually started to change from an unbearable tingle in my head as I rubbed to a wave of pure physical joy that started farther and farther down my shaft as the weeks went by. Once it reached all the way to the base, I found I could bear the tingle in my head, and that it led to a crescendo of ecstatic tension and release. I guess I couldn't take much of that wonderful tension at first, so the release started out weak, and only got stronger as I learned to hold on to the longing longer before letting it go. Like I said, it was gradual-maybe now you understand why I'm not sure where to set the boundary between making the head of my penis feel amazing and giving myself orgasms.
After discovering my new method, my fingers and my penis got to know each other very well. I started connecting the sexual feelings I was having with masturbation. I discovered how much more incredible my still-dry orgasms could be when I masturbated thinking about, for instance, a cute girl in my class whose shirt hung just the right way when she bent over.
Then, one summer, stuff started coming out when I played with myself. I'd been giving myself fairly regular dry orgasms for some time, but that summer was when masturbation really became part of my daily routine. Almost every morning, I would lie in bed and rub away at the erections only boys who've never yet felt cum flowing through their penises get. At first, I would notice just the tiniest hint of wetness on the very end of my head right after finishing a particularly hair-raising masturbation session. After that, there'd be a drop or two of clear, slippery fluid hanging from the tip of my penis after my morning orgasm. Then, sometimes, the same stuff would dribble out as I was in the final spasms of getting off. That's where the gradual changes stopped, which is why I remember my first cum so much better than my first orgasm.
For the next several months, things went along just like that; wake up hard, masturbate, feel a little something thick and slippery dribble out at the end of my orgasm. I remember lying on my back in the bath tub that morning. I hadn't played with myself in bed, and I needed to get off. I don't really recall starting to masturbate, just the feeling as the pleasure started to build down at the base of my shaft. It was the same familiar feeling, but it started to get stronger; then it was more pleasure than I'd ever thought possible as I felt my cock suddenly fill with something hot and thick. Then it was flowing through my still-small penis, as I tried to remember how to breathe. I couldn't think, couldn't even wonder what was going on; my whole existence for a moment was the sudden whole body shuddering of pure ecstasy that pumped through my little dick as I squirted my first cum almost to the ceiling. There was plenty of it, too. I shot a load I'd be proud of today the first time.
After I started cuming, the next thing I had to figure out was what to do with all the sperm my balls now provided my lengthening dick with. When I masturbated in the bathroom, it was easy; either let the shower take care of it, or aim down and squirt straight into the toilet. (I do remember kind of enjoying the intensity of bending my penis down like that as I came.) Still, masturbation has always felt the best for me in bed, when I can relax everything but my hand and my penis. I tried pressing a wad of kleenex against my head as I started to cum, but that got in the way of actually masturbating. Sometimes I would pinch the tip right as my orgasm started, holding everything in until the spasms stopped, then squeezing the cum out of my penis into a kleenex afterwards, but that just didn't really satisfy. Finally, one morning in bed, I could feel an especially strong orgasm building at the base of my penis. In a quick resolution that nothing was going to get in the way of it, I just pulled my t-shirt up and squirted my cum right onto my bare stomach. It felt amazing, just letting go like that. After that, I got very used to the feeling of my own hot cum spraying onto me and pooling in my belly button.
The next real milestone was when my second girlfriend taught me about lube. I was already twenty years old. I had gotten my high school sweetheart off-fingered her to her first orgasm, in fact-but the only release I'd gotten from her was the one time I accidentally (and very embarrassedly) came in my pants while playing with her virgin clitoris. My first girlfriend in college, however, was much more experienced than I, and was ready to give me my first handjob a few days after our first date. That one was in her bed, and dry, but soon after, we were taking a shower together, and she asked if I wanted her to get me off. The answer, of course, being yes, she asked me what kind of lube I use when I masturbated. I said I didn't; she looked mystified, then shrugged, squirted some conditioner onto her hand, looked me right in the eyes, and gently took hold of my penis down at the base, sliding her hand up to my head as she started jerking me off. I can still almost feel the first time she slid her slippery hand up and down my dick. I still mostly masturbate dry, but lubing up is fun every now and again.
The next big development-maybe the most important since I started playing with myself-was getting up the courage to ask my girl to watch me masturbate. It wasn't for lack of desire; my second girlfriend got a kick out of 'corrupting' me, and was very turned on by the fact that she'd gotten to take my virginity. Periodically, she'd ask if I had any fantasies I wanted her to help me live out. I never had the guts to tell her I wanted to jerk off while she watched. Fast-forward to a couple years after college, now living with my third girlfriend, soon to be my wife. I was sick as a dog. Or at least I had been. When ever I get ill, as soon as I'm on the mend, I get really horny. This kind of sucks, because my woman (understandably) doesn't want to catch what I'm getting over. I can sympathize with this, but it didn't change the fact that I really needed to cum when we were getting ready for bed that night. I was nervous about asking, but the nerves made it even more exhilarating as I said 'Honey, I really need to get off; would you mind if I masturbated?'
She didn't understand at first. Her reply: 'Sure-do you want me to help?'
I replied, lamely 'No; I can do it.' And then at her incredulity, 'No one's ever seen me masturbate before. I'd like you to be the first.' She smiled so sweetly it almost made me cum without the need for my hand.
'Okay.' She said as she pulled up her shirt, already getting turned on. 'You can play with my boobs if you want to, too.' Suffice it to say that I did, and that my right hand brought my penis to the most incredible orgasm it had yet as my left squeezed one of her wonderful, soft breasts. Since then, we've made masturbation a regular part of our sex life; most of our foreplay is generally watching each other play with ourselves, and I'm actually quite disappointed if she doesn't finger herself during sex.
The latest is that I've finally learned how to fully enjoy the results of my circumcision. As I said earlier, my dick got cut loosely, with both a fair amount of inner skin and shaft skin movement left. The doctor that circumcised me also left me my frenulum, though, as I understand it, it's usually cut off of a circumcised boy's penis. Both it and my remaining inner skin are very sensitive. It's ironic; I actually discovered the joys of having had my penis cut from anti-circumcision web literature. Something I read told me that running a finger up and down my freunulum was the closest I could get to feeling what it was like to have a foreskin. For the record, that feels very nice. I spent several years wishing I hadn't been circumcised. Then, earlier this year, I discovered my inner skin. I'm talking about the pale pink skin between my head and my circumcision scar that would have been the inner lining of my foreskin, lying against my head, if I hadn't been cut. One day, I was playing with my frenulum, and my fingers strayed to the rest of the skin between my head and my scar. You can't fake pleasure like that. It was the first time I've shot a load of cum out of my penis without stimulating my head at all. Since then, I've spent a fair amount of time exploring the joys of a gentle touch on my dry inner skin and my dry head. I guess what I'm saying is that, even at 29 years old, I'm still learning about the wonders I can experience with my hand and my penis. I know circumcision was supposed to be a 'cure' for masturbation; all I can say is that, in my case, that whole thing totally backfired!