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Dear Sophie,

My boyfriend has been wanting to try anal, but honestly I can’t see any good in it. I’d imagine that it would be painful and not feel good for me at all! Isn’t my vagina good enough?

Of course your vagina is good enough. Your vagina is charming and there is not a thing wrong with it. Your boyfriend doesn’t have a problem with your vagina; he just wants to try something different (and to many people, the idea of anal sex is pretty “forbidden” and “taboo,” which can be exciting). If that’s your primary concern, don’t worry. You should bring it up with your boyfriend, though, so you can hear from him and not just me that your vagina is his favorite thing in the world.

If you’re more worried about the potential pain, see my excruciatingly extensive answer to the question below.

Dear Sophie,

My boyfriend wants to try anal. I have heard terrible things about how it hurts and just isn’t worth it. What is your opinion on the matter?

As a matter of fact, probably the majority of people don’t go about anal sex the right way and can run the risk of injuring themselves. Here’s the most important thing you need to know: If it hurts, you are doing it wrong. If you do it the right way, it should never hurt, bleed, or anything else. At best, it can be an amazing experience for everyone involved; some women even have better orgasms from anal sex than from vaginal sex. At worst, it might be weird and unpleasing. But it shouldn’t be painful. The bad news (actually, forget it, this is sort of good news too) is that you have to be very careful, patient, and honest in the way you go about it.

If you want to make the commitment to anal sex—yes, it’s a commitment and a process, not just a one-off thing—I highly recommend that you buy The Ultimate Guide to Anal Sex for Women, by Tristan Taormino. It’s a really terrific resource that debunks myths about anal sex, explores common fears, and details a safe way to go about the process. (The Ultimate Guide to Anal Sex for Men also exists, incidentally. And pegging is a wonderful thing.) But before you get the book, here are some tips to start you off:

1) Don’t do it unless you sincerely want to do it, or are at least sincerely very comfortable with trying it. I mean, this goes for basically everything sexual, but bears repeating. You should never approach anything sexual with feelings of resentment or fear, because it will not end well. Plus, my favorite quote from The Ultimate Guide: “You must, must do this because you want to do it…Of all the parts of your body, nothing knows a liar like your anus. So if your mind is saying ‘Yes! Yes!’ and your heart is saying ‘No! No!’ your anus will always listen to your heart.” Um, that’s adorable, I’m just saying.

2) You (the receiver) should always be very clear and honest about how you’re feeling and what you like or don’t like. Although this sounds counter-intuitive, you need to be the one in control of the situation, because you are the one who could potentially get hurt. Your boyfriend can keep a lid on things until you get comfortable, no matter how long that takes.

3) Don’t assume that his penis is going buttwards the first time you try any anal stuff. It really is a process, and will take some time. Start with stimulation around the area, then gentle fingering, then toys (or more fingers), before you get to that point. (Mind you, this should probably be spread out over a series of sessions, not just one night. And I’m really sorry I just said “sessions,” that sounded so clinical and gross.)

4) Use so much lube. Use boatloads of lube. BOATLOADS, DO YOU HEAR ME.

Those are probably the most useful pieces of information I can give you, but the most important thing is for you to both do your research and communicate very openly with each other. Best of luck, and of course don’t forget to practice safe sex!

Got a problem of your own? Tell me about it at my Formspring.