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 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 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. Read more »