Anal with aplomb

Dear Sasha, I’ve had a serious thing for a lady’s asshole, and, at least, the concept of anal sex since my mid-teens. I’m 31 now. So far I’ve had miserable luck finding women who’ll let me indulge my fantasy, which, as you know, is not that off-the-wall nowadays. This makes it all the more discouraging. For some soul-crushing reason, I always fall in love with women who are uncomfortable with that part of their anatomy.

I’ve only had a handful of opportunities to have anal sex (mostly with one woman), and I’ve dated quite a bit. The woman with whom I had my first experience, and had hoped would share my interest, grew to hate anal sex and we eventually ended the relationship for other reasons.

Now, I’ve fallen for yet another woman who insists that “I will never have the pleasure” of knowing her that way. I’m not sure what to do. I feel like life is maybe playing a bad joke on me. I know the percentage of women who actually get off on it isn’t that high, but I figure there’s got to be a like-minded someone out there for me.

The big question is, at what point does one say to themselves that their sexual fantasies mean enough to them that they should give up an otherwise perfectly good relationship?

And also, at what point is someone holding on to an unrealistic dream/expectation, or is possibly exhibiting an unhealthy obsession?

Ironically, I started consuming porn in my teens to satisfy my love of a lady’s posterior, but now I almost can’t watch (but sadly have to) because it breaks my heart to see how common the act is today in the medium.

-Slowly Dying Inside

I have slept with porn actresses and even they have boundaries in recreational exchanges. So keep in mind that when you’re watching them on film, you’re watching them at work being paid a good deal of money to have their asses pounded off.

And let’s talk about this handle of yours, one that implies there has been some runny-nosed begging involved. Unless this is part of an agreed concept, if we want to have sex, we do not beg for it. And we most particularly do not beg for anal sex, especially not from girls.

Girls do not like being viewed as the Keepers of the Anus. To know so vividly that a man has such an overriding anal sex obsession is unattractive. We have to imagine where it stems from and then we have to imagine you in short pants at church sitting beside your mommy. Not sexy.

In my experience, there are several types of heterosexual male anal sex aficionados, but for the sake of argument, let’s group them in two common categories: There’s “I’m Gonna Fuck Your Ass, Little Bitch” and then there’s “I’m a Little Bitch Who Wants to Fuck Your Ass.” Let’s say you fall into the latter—bluntly put, the creepier one. Of course, generally speaking, we anal sex fans are creepy—we like anal sex because it’s dirty and defiling and utterly fixating. But my feeling is, if you’re going to be creepy, at least do it with the gusto and aplomb that defines the former.

All that said, I barely know any women who don’t do (and like!) anal or haven’t at least given it an admirable try, so here’s my closing theory: you are not simply ending up with girls who don’t want to have anal sex, you are choosing them. Because for Little Bitch Who Wants To Fuck Your Ass, that’s part of the deal. Little Bitch feels lasciviously ashamed of his obsession. And what better way to fuel that obsession than to choose someone who adamantly denies him?

Got any questions for Sasha? E-MAIL: POULEDELUXE@YAHOO.COM