How I Discovered Prostate Orgasms

I don't remember when I discovered anal play or what led me to it. I've always enjoyed fucking my girlfriends in the butt, though I've only rarely had the pleasure. What I don't recall is when or how I discovered how the pleasure to be had from my own butt being fucked.

I would prefer to have a (female) partner do me, but only on a few occasions have I been privileged to have someone else penetrate me with a dildo or vibrator. Most of my experiences of this kind have therefore been with myself.

Before we continue, let's get one thing clear: A guy's enjoying anal penetration does not 'make him gay'. As has often been pointed out, the claim is absurd on its face. I mean, what is the argument? Gay men enjoy anal penetration; Fred enjoys anal penetration; so Fred must be gay! Well, gay men enjoy getting blowjobs, too; every man I've ever known enjoys getting blowjobs; so every many I've ever known must be gay. Right?

That argument is so terrible that it obviously can't be what really drives men (and it's almost always men) to worry that a guy's enjoying anal penetration 'makes him gay'. The real argument is quite different. It's that a guy's enjoying anal penetration makes him feminine, and being feminine makes him effeminate, and that makes him gay. The steps of this argument are pretty lame, too, but it at least makes some kind of sense. But to think that certain sorts of sex acts are exclusively 'feminine' or 'masculine' is sexist on its face. And even if it is 'feminine' for a man to enjoy anal penetration, why is that supposed to be bad? Could it be because what's feminine is inferior and men should not stoop to such things? That kind of reasoning only makes sense to people who are sexist andhomophobic.

What's really ironic about this sort of concern is that one of the joys of anal penetration for men is how it stimulates the prostate. Which, of course, is an organ only men have.^* Indeed, the main reason I like anal play so much is the kind of orgasm it gives me. I have always envied women because there are so many ways they can masturbate, and because of the seemingly endless orgasms some of them manage to have. One woman I knew used to cum five or six times nearly every time we had sex, one right after the next. I'd have sold my soul to be able to do that, but my anatomy always got in the way. Until, that is, I discovered my prostate.

My earliest anal masturbation, in my college years, involved dildos. Dildos are for fucking, and that's what I started out doing. I found out pretty fast that, if I fucked myself at the right angle, the head of the dildo would bump into my prostate, which felt fantastic. At first, I found it difficult to get the angle just right. If it was too steep, it would hit too hard, which could be painful. If it was too shallow, it would miss my prostate altogether. But when it was just right, it would cause intense sensations deep inside my body and make precum flow out of my cock like a river. Very quickly, the sensations would build towards that pre-orgasmic state, and I would find myself lingering there for a long time. It felt like, if only I could just keep at it long enough, or hit just the right spot, I'd cum. But I would always tire before I got to that point, or just getting too horny to keep at it, so I'd stroke myself to an orgasm with the dildo buried inside me. The feeling of my ass grabbing at the dildo while I came was wonderful. But I always wondered what would happen if only I could keep at it longer. I had to cum, eventually, right?

So that became my quest: To cum, just from anal stimulation.

My First Prostate Orgasm

One day, I was incredibly aroused before I even got to bed. I'd been surfing for a while, reading stories and looking at porn. The inside of my undies were covered with precum. I got out my favorite dildo, lubed it up, and slid it into my butt. I lay on my side and pulled my legs up, which I'd discovered created a good angle for getting at my prostate and helped keep my arm from tiring. The deep, intense sensations started more quickly than usual. I remember looking down and seeing a puddle of precum growing on the sheets. Soon, I was moaning loudly as I fell into a fantasy of my girlfriend fucking herself with the very same dildo while she rubbed her clit. Suddenly, to my great surprise, the sensations started to rise beyond what they'd previously been like. And then it happened: The familiar feeling of orgasm welled up slowly within my body, and then the contractions began, starting deep inside, and making their way to the tip of my cock. I shuddered uncontrollably as my whole body was overtaken by pure pleasure. It went on for a very long time, longer than any orgasm I'd ever had. When I finally came down, I looked at my cock and noticed, first, that there was no cum, just a puddle of precum, and, second, that I was still hard. And I noticed, too, with great excitement, that I was experiencing no post-orgasmic lack of interest.

I basked in the glow of that amazing orgasm for a while, and then I want right back at it. I did it slowly at first, but harder and faster as I felt the same feelings build again. It didn't take as long the second time for the waves to start crashing over my body, throwing me mercilessly against a rocky shore of overwhelming joy. That second orgasm was the most intense I'd ever had. I remember thinking, at one point, that I had no idea how long it was going to last. It only stopped when I stopped fucking myself, not because I wanted it to stop, but because I just couldn't cum so hard and keep moving my arm at the same time. And again: There was no cum, no loss of erection, no satiation. I came twice more that way, before deciding it was time to ejaculate, which I did, by stroking myself in the usual way. And that orgasm too was unusual, because there was no 'peak'. There was no building, building, building, bam! Rather, the ejaculation came suddenly. Without warning, I was just spurting huge amounts of cum so far and so powerfully that it hit my face.

So that was it: My first multiple orgasm, and I'd managed five in just one session. It turned out women weren't the only ones who could cum over and over. I was damn sure I had found nirvana, and I'd achieved my quest, in one sense: I'd cum, just from fucking my ass, though I still wanted to be able to ejaculate that way.

I wasted no time trying to have more multiple orgasms as soon as I had some more privacy. To my great disappointment, however, it wasn't at all like riding a bike. I thought I'd learned the secret and would be able to repeat the experience any time I wanted. But, in fact, I was unable to have even one of those special orgasms again for quite a while. If I could have one, I found, then I could have almost as many as I wanted. But getting that first one was difficult. I tried fucking myself in different ways. I tried getting myself really aroused before starting. But nothing seemed to work reliably. It was random, and it was frustrating.

Thus began my second quest: To find a way to have multiple orgasms when I wanted to have them.

Vibrators To the Rescue

The obvious thing to try was a vibrator. I'd toyed around with those when I was younger. I found one a Wahl vibrator at the house of a woman whose kids I used to babysit and 'borrowed' it now and again. (Yes, I know that was kind of gross. I was a teenager. Go figure.) I decided that getting some of those vibrations to my prostate would feel good. So I ordered up a couple different styles.

All of them turned out to be useful. The soft, phallic vibrators I ended up using in much the same way I had been using a dildo before. Adding the vibration definitely felt good, especially if I turned the vibrator on only after the intense feelings had started welling up deep inside me. There were times that this combination got me multiple orgasms, but it ended up not being any more reliable a method than the dildo, really.

The harder models I used in a different way: Instead of fucking myself with them, I'd just put them in my ass and set the tip of the vibrator on or alongside my prostate. That didn't work so well with the softer vibrators. Since they were soft, and had the vibrating bit in the base, there wasn't much vibration at the tip. But the first time I used one of the hard ones, I remember being shocked by the intensity of the sensation and thinking, "Oh yeah, this is going to be good". And it was. I pressed it hard against my prostate, occasionally moving it in and out, or side to side. I'd had multiple orgasms on a few occasions by then and could tell when things were going in the right direction. But I wasn't prepared for what happened next. Women often speak of finding just the right spot, holding the vibe right there, and then exploding. That's exactly how it happened for me.

I was moving the vibe around and then suddenly, there it was: the perfect spot. The sensations immediately became incredibly intense. My hips rose up off the bed, and I reached down and grabbed my balls hard, pulling them up toward me. The tension was unbearable, and I thought I was going to pass out. And then, without warning, wave after wave of the most amazing pleasure I'd ever experienced carried me along. Body-wrenching contractions started deep within my body and convulsed my entire being with their power. Even more amazingly, since I was using the vibrator, I didn't have to move my arm, so I didn't need to stop to keep it from falling off, and I was only halfway down from the first orgasm before I was on my way back up the slope to another one. Less than a minute had passed, and I was cumming a second time, with bolts of pleasure shooting out from some place deep within me that I had never even known existed, taking hold of my body, and shaking me to my core. That one wasn't as intense as the first one, but it was pretty damn good.

I don't remember how many times I came that day, but it was a lot. Seven or eight times before I'd had enough. I stroked my cock until I ejaculated, with the vibrator still buzzing away inside me. I was so turned on that I started scooping up my cum, licking it off my hands, and rubbing it all over my face. And there was a ton of it, too. That got me so turned on that I stroked myself to another orgasm. That one was more relaxing and involved only a dribble of cum. I was drained but very, very satisfied.

Once again, I thought I'd discovered the secret, and once again I was disappointed. The hard vibrator, for sure, was able to get me off a bit more reliably than the dildos. G-spot vibrators, which I tried next, were a bit better. But none of them were really reliable. And I still hadn't managed to ejaculate without touching my dick.

Prostate Orgasms on Demand

Fate was on my side, though. Several months later, I ordered a couple more toys, and my order arrived with a free waterproof vibrator. I didn't care that it was waterproof. What was cool about it was that it had the vibrating mechanism at the tip instead of at the base, and that meant that the vibrations at the tip were much more intense than those in any of my other toys. That, I figured, had to be a good thing, and I wasted no time finding out.

That vibrator turned out to be the best one I'd had to that point, and my first experience with it was beyond memorable. I came over and over and over, masturbating with that thing in my ass for over an hour, though I did pause at one point to give myself a real good butt-fucking with one of my dildos. I'd say I lost count of how many orgasms I had that day, but I was so incredibly turned-on that I was never even able to start counting.

Even that vibrator, though, was still not reliable at giving me multiple orgasms. It did, however, help me attain my other quest, totally accidentally. One day, I was playing with it and was feeling quite tired. I'd been trying to have that first 'special' orgasm, but nothing was working. So I just decided to rest for a while. I lay back and left the vibe buzzing in my ass. I rested there for probably five minutes and then started mindlessly playing with my nipples, pinching and squeezing them. Then I felt it start. I was already very excited, from what I'd been doing previously, and my nipples have always been very sensitive, so playing with them was making my cock really hard. I was about to reach down and move the vibrator back up against my prostate when, all of a sudden, I felt myself racing towards orgasm. I reached down and put my hands alongside my cock, touching my thighs, when my cock suddenly started shaking and spewing cum all over my body. It wasn't all that great an orgasm, in fact, but what was satisfying was the fact that I'd finally done it. I'd finally ejaculated just from anal stimulation!

What finally did allow me to have multiple orgasms on a regular basis was the original Aneros massager, which I purchased not long after the episode I just described. I'll talk more about it, how it is used, and some of the other techniques I've learned since in future articles in this series.

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* When I speak of "men" and "women" here, I generally mean anatomical males and females. This use of the terms is not meant to offend men and women whose bodies do not match the usual gender expectations. As I'll explain in other posts, I'm a gender-queer myself.