Carnal Knowledge: Anal Sex and Keeping Lists of Conquests

Great reader question this week about anal sex. I’ve also received a lot of emails about The List, both expressing readers’ wishes that they had started one way back when and also wanting to know more about the contents of my list, so I’ll be addressing that as well.


I’d love to get your thoughts on something. I have been seeing a lady for about a year and a half now, and we both think it might be the real thing for us. Before her I was single for a very long time and got around a good deal. One of my favorite things to do has always been anal sex. I have enjoyed doing it a number of times with most of the women I was with. Even the ones who were hesitant at first or who had a previous bad experience with trying it (not at all uncommon) were able to enjoy it after a little working into it. I am, quite frankly, skilled at the act and know how to take it gradually and let it happen.

My problem is that I don’t want to try it with the woman I have fallen in love with. She has told me of really hating her attempts at it and not being into it. She also knows about my love of it. As we settle into things a bit and explore our sexuality together she has brought it up a few times. Mentioned that she was ready to try it with me, yet I realized that I really wasn’t into doing it with her. I blew it off the first few times it came up but now she is asking me why I’m not pursuing it with her. I still sometimes fantasize about the times I did it before but just have no desire to go there with her. Tell me what you think, please! I desperately want to stay with her and need to figure this thing out. – Charming Bastard

I want to preface my answer with the statement that I am not a psychologist. That being said, my feeling about this problem is that it’s the Madonna-Whore conundrum that so many men have issues with. They want to experiment and get freaky with a wild woman in the bedroom, but when it comes to being that way with the woman who might be The One, they can’t do it.

I can’t believe I’m resorting to the upcoming reference, but it is applicable. In a season 2 episode of Sex & the City, Charlotte (the prissy one) is debating about whether to have anal sex with her boyfriend and she says, “Men don’t marry the up-the-butt girl! Who’s ever heard of Mrs. Up-the-Butt?” I also happen to know many guys that this has happened to. They can’t reconcile the idea of bondage or anal sex or threesomes or whatever with the woman that might be the future mother of their children.

Here is where the viewpoints of the parties involved start to drastically diverge. To the man, this probably seems like a good thing. To him, anal sex is something skanky girls do. The types of girls he had flings with in his younger days are the types of girls that let you fuck them in the ass. The future Mrs. Charming Bastard isn’t like those girls and therefore you have no desire to drag her down or degrade her that way.

To your partner, it feels like she’s not good enough for anal sex. It is making her feel like she doesn’t rate as cool or sexy or wild enough to be that adventurous with and it’s hurting her feelings. To the girl, this makes her feel like she’s less than the girls you had random hook-ups with before you met her.

My advice to Charming Bastard is to try to get used to the idea that the activities from when you were a swingin’ bachelor are not mutually exclusive from a committed relationship. One thing that is obvious is that you have not lost interest in anal sex. You said yourself that you still fantasize about the times you did it in the past. If you haven’t lost interest in anal sex, it means it’s something about your partner.

In addition to the Madonna-Whore issue, it might also be because your woman told you she tried anal in the past and didn’t like it. You might be afraid you are going to upset her or hurt her. You might also feel like she’s only trying it for you and that she isn’t truly interested in it.

On that front, I say: take her word for it. She says she wants to try it with you and that means she trusts youhot drinks... and loves you enough to want to give something she hasn’t enjoyed in the past the ol’ college try. That’s awesome! Take advantage of it! It’s another lame reference, but I happen to agree quite strongly with “a lady in the street but a freak in the bed.” *That* is the type of girl you want.

I mentioned in a previous column that people should follow the rule of 3 when it comes to trying something their partner is interested in: do it once to try it, do it again to get used to it, and do it a third time to see if you like it. If you don’t like it after 3 tries, then it probably isn’t your thing. Also, your partner cannot get mad at you after trying something three times and not liking it. So I advise you, Charming Bastard, to try anal sex with your lady three times. If you STILL cannot stomach doing it with her, then at least you tried it.

Finally, I want to address something about anal sex in general that I think is a myth among many males. Anal sex isn’t just pleasurable for you. I have had boyfriends who thought I was just “letting” them have anal sex with me because I was trying to be nice or do something they were interested in. Pssst! Anal sex is nice for us too. There are a lot of nerve endings in the anus and it feels good. It’s not better or worse than vaginal intercourse, it’s just different. Also, I have found that when I have vaginal intercourse doggie-style, it’s hard to stimulate my clit because the skin down there is being pulled kind-of a funny way. When it’s anal sex instead of vaginal sex, it’s easier to play with myself and then orgasm. So don’t worry about anal sex only being for you. That is NOT the case.

*The Ex List*

I threw some quick facts together about the list. I’m STILL not going to reveal actual numbers, but I have crunched some percentages and sussed out other facts that either I found interesting or were asked of me in emails.

First off, 95% of the list is men. The other 5% is women. Yes, sometimes I find women attractive. Yes, sometimes that attraction comes to fruition. I wasn’t a LUG (lesbian until graduation). It started in high school and it continues today. I even had a girlfriend, all official-like, in undergrad.

10% of the list is made up of guys named either Brian or Matt. I found that weird. 11% of the list’s last names start with M. And 33% of the list’s names start with either B or J. That fact made me giggle a little.

A reader asked if there are any people on the list whose names I don’t know. I don’t know the last name of 7% of the list. I don’t know the first or last name of 2% of the list. Now, none of these were people whose names I NEVER knew. I just forgot (usually due to alcohol) by the time I updated the list.

On my list, people are listed based on the farthest we got. So I have had sex with 26% of the list. I have made out with 51% of the list. By “make out,” I mean kissing and what the kids call “heavy petting,” but not any downstairs action. I have either (or both) give or received oral sex with 15% of the list. Of course, if I had oral sex with someone and THEN slept with him, he or she would be categorized under “sex.”

There are two sets of siblings on the list: John and Phil C. and Drew and Jordan M.

1% of the list I slept with at the same time.

10% of the list happened from 1994-1998. 1999-2002 account for 66% of the list. I guess you can tell when I was a stupid undergrad, huh? 2003 drops to 1.5% of the list because I got a serious boyfriend. 2004 jumps up to 7% of the list because we broke up. 2005 goes back down to 1.5% because I got a new serious boyfriend. 2006-2008 is 14.5% because we were on again, off again.

If anybody wants to know anything else about the list, feel free to ask.

Questions? Comments? Suggestions? Email See you guys next week!

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About Claire Sebastian Claire Sebastian is a recent law school graduate looking to hold on to the one remaining piece of her soul by penning a weekly sex column for TSB Magazine. Turn-ons include witty banter, intelligent debates, “These Arms of Mine” by Otis Redding, being kissed on her neck, singing along under your breath while dancing with her, and running your hand through her hair. She can be found writing at various other sites online but under a different name. Guess you’ll just have to wonder where…

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