Dear Miss Single USA,

I could use with some advice regarding sexual practices, specifically anal sex. Much secretiveness is associated with this, be it through the state legalities or perception, religion etc. My concern is, can a woman enjoy it or is it something they do just to please a partner?

Thanks muchly,
Assman

My new roommates and I are currently in the market for a cheap tandem bicycle. Seriously, how cute would it be for two girls in pigtails and bikinis to ride a tandem to the beach or to the grocery store?! Anyway, I’ve been doing some regular searches here and there on some online Chicago classified sites – you’d be surprised how expensive tandems are nowadays! Last Monday as I was doing my weekly search on craigslist and I decided that I’d waste a little time in the personals section of the site, mainly in the men seeking women category. One of the first ads that popped up had a title that inquired if I was feeling “adventurous.” Always up for a good adventure, I clicked on it. And this is what I found –

OK, so here's the deal. It was a very uneventful weekend. And I'm not ready to wait another week until Friday gets here. So, this is what I think we should do this Sunday afternoon. Let's meet for a drink or two. We can share a few laughs. Then, if the day is going well, allow me the pleasure of going down on you! :). What do you say?? Could be quite the evening for the both of us. Plus, can you think of a better way to start off the week?

Of course I responded. I haven’t heard anything back yet, but I’ll keep you all posted.

What I’m trying to say, Mr. Assman, is that there are all sorts of things out there that people are into and that many of us never knew about. For example, I never thought that there would be a guy who all he wanted to do was go down on yours truly without any strings attached specifically because I was adventurous enough to click on his craigslist posting. Yes, people are secretive about such things but that’s basically because a lot of people are sexually secretive in general. I don’t know about all of my friends’ kinks and fetishes and I think that’s probably for the best. It would probably alter my personal outlook on my best friend if I suddenly found out that she was into blood play and scarification, but hey, who am I to judge?!

To answer your questions, yes, Assman, women really can enjoy anal sex. Not all women do, but some do and I know some who REALLY enjoy it. I wouldn’t necessarily say that they prefer it over vaginal intercourse, but I have had a girlfriend or two (after a few cocktails) tell me how she just wants to find a guy who really knows how to bang her in the bottom. Just like my craigslist friend who likes to spend his time downtown, people are into all different things.

But just because some people are into anal, it does not mean that all girls want it. Just like some men enjoy having their prostate tickled during intercourse or oral sex, there are many who get freaked out by it. Yes, some women do it specifically to please a partner and usually some sort of schedule is worked out – once a month, only on birthdays, New Years Eve, etc.

If anal is something that you definitely need to perform in a relationship with your girlfriend, then I suggest bringing it up as early as possible in things. Just be straightforward about it. What’s the worse that can happen – she’ll say no and call you a freak and throw you out of her apartment? Big deal. She wasn’t the one for you, Mr. Assman. If she’s up for giving it a go, try to make it the most pleasant experience for her that you possibly can. Let her associate anal with love rather than the blinding pain that may cause her to pass out in her shower. Just a suggestion.