I don't remember when I discovered anal play or what led me to it. I've always enjoyed being on the giving end of anal sex with my girlfriends, though I've only rarely had the pleasure. What I don't recall is when I discovered how much pleasure was to be had from being on the receiving end of butt play.
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. 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 fear that having certain sorts of sex might suddenly cause them to fall in love with a man. 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 all pretty questionable, 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? (And what's so wrong about being gay?) 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 and homophobic.
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 orgasm 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.
As I'll explain, it took me quite a long time to learn how to have prostate orgasms reliably. It's a tale of extraordinary pleasure and equally extraordinary disappointment. I got there in the end, and, if you have a prostate, then you, in all likelihood, can get there, too. But doing so means learning something new about our bodies that no one, probably, has ever begun to tell us.
Before I start giving advice, though, let me tell you my story.
My First Prostate Orgasm
My earliest anal exploration, 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 penetrated myself at the right angle, the head of the dildo would bump across my prostate as I moved it in and out, 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 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 get 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?
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My SO (who is male-bodied) reached orgasm from prostate stimulation alone when using this for the first time, so it's pretty damn effective. – PyrgusMalvae | https://www.edenfantasys.com/vibrators/anal-vibrators/eden-flexi-vibrating-anal-dildo| Eden flexi vibrating anal dildo]
One day, I was incredibly aroused before I even got to bed. The inside of my underwear was soaked with precum. I got out my favorite dildo, lubed it up, and slid it into my rectum. 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. I fell into a fantasy and was moaning loudly when 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 the contractions began, starting deep inside me and spreading outward. 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 noticed first that there was no cum, just an even larger 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 went 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 stimulating 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.
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.
My Quest for Reliable Prostate Orgasms
I was sure I had found nirvana, and 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 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 different angles and different positions. I tried getting myself really aroused before starting. But nothing seemed to work reliably. It was random, and it was frustrating.
The obvious thing to try was a vibrator. I'd toyed around with those when I was younger. I figured that getting some of those vibrations to my prostate would feel good. So I ordered up a few 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. 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 moving them in and out, I'd just put them inside myself 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 very slightly in and out, or side to side. I'd had multiple orgasms on several 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 erupting. 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 ramped up. My hips rose up off the bed, as if searching for something. The tension was unbearable, and I thought I was going to pass out. And then, with body-wrenching contractions starting deep within me and convulsing my entire being with their power, wave after wave of the most amazing pleasure I'd ever experienced carried me along in orgasmic bliss. 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 my arm 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, 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, before I'd had enough. 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 predictable.
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 stronger than with any of my other toys. That, I figured, had to be a good thing, and I quickly set to 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 for nearly two hours, though I did pause at one point to give myself a real good pounding 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.
It had taken me about five years to find the right toy, and to learn enough about my body, but at that point, finally, I was able to have multiple orgasms almost whenever I wanted to. Not long afterwards, I purchased the original Aneros massager, and then I was really on my way. Now, I have a large collection of prostate toys, and I regularly have fifteen, twenty, or more orgasms in a session. I'll talk more about the various techniques I've learned over the years in the third article in this series.
In the next one, I'll answer a simpler question: What is a prostate orgasm anyway?
Footnote
* When I speak of "men" and "women" in this article, I 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.
** In retrospect, using this toy anally may not have been the best idea. The vibrator in question does not have a flared base, which means it would be possible to lose it inside oneself---not something one wants to have to explain to the doctor at the emergency room. In general, only toys that have a base large enough to prevent the whole toy from entering the rectum should be used anally.