My boyfriend has a real thing for anal sex. I had never done it before so I was nervous but I’ve heard from lots of girls (and from you talking about Eloise, obviously) that anal sex is awesome, so I was down to try. We did all the stuff everyone recommends like using lots of lube, starting with fingers, moving up to dildos, then eventually to a cock, etc. No matter what we did I hated it. It was painful, not sexy, and generally just a bad time for me in every way. I told my boyfriend that I gave it a shot and am just not into it, so I guess it won’t be happening anymore.

However, he won’t drop it. He asks for it all the time, brings it up all the time, just won’t stop thinking about anal sex. I’m not entirely opposed to trying again but really: how much do I have to try and like this before he accepts that I just don’t?

-Not Into Anal

This is a tough one and I’m not sure you’re going to like my answer.

First off, kudos to you for trying anal sex. Although I talk a lot (and Eloise talks a lot) about how stupid it is that anal sex is stigmatized in American culture as being so gross and painful and awful, that disdain does not prohibit me from understanding that it can be a very daunting thing for girls. And as anal sex becomes more accepted in society it will become more “expected” which will only make it more difficult for girls who don’t like it to avoid situations like the one you’re in.

Normally I tell everyone to try everything twice. I can’t tell you the amount of women in my life that have told me they don’t like a specific sexual act and then have changed their minds about it 100 fold once they’ve tried it again under different circumstances. This is especially true for anal. Their first anal experience may have been an accident (“Whoops, wrong hole!), a rape situation (“Whoops, wrong hole! But I’m not going to stop now.”), or any other number of negative situations. Since they’ve now done anal, they think they know that it is 100% bad and never want to do it again, when they don’t realize that if they did it in a prepared way with someone they know and trust in the right environment they may very well enjoy it. So that’s what I say.

But it seems from your letter that you did just that. You took all the right steps and were a good sport and tried to be a great girlfriend for your boy, but in the end you just didn’t care for it. Encouraging you to go through that again seems to me to probably be a lesson in futility. However, maybe it’s not, maybe you should try it again. Let me put it this way…the worst that can happen if you try it again is that you have a bad time with it, but the best that can happen is that you like it more than you did the first time. Ultimately, the choice is up to you.

Let’s assume that you try it again, making it twice that your boyfriend has put his dick into your ass, and you still hate it just as much as you do now. To me that is more than enough to solidly declare to your boyfriend that you don’t like anal sex and never will and that it is now permanently off the table. If he disagrees and continues to whine and moan about how he wants to fuck your ass then you need to lay the smack down and say, “It’s me, or anal sex. You can’t have both. So pick.”

The problem is that either way will probably be bad. If he picks to leave you then that will obviously suck. But if he picks to stay with you without anal sex, he may grow to resent that he can’t get his anal rocks off while he’s with you. That resentment could permeate through the relationship creating a slow and drawn-out death. It could not go down that way but if anal sex is really that important to him, it likely could. So you’re damned if you do and you’re damned if you don’t.

As of right now you are dating a guy who really loves anal sex and you are a girl who really does not like anal sex, which you may not believe but makes you fundamentally incompatible. Unless you want to open up your relationship so he can get his anal kicks from other more willing ladies you may both just have to accept that you’re not the right fit for eachother. Sorry for the bummer of an answer, NIA, but sometimes the hard truth is what you have to lay down.