My fiancé wants to try anal sex. I have to admit, I’ve always been curious about it. But now that I’m with my future husband and he is actually interested in doing it, I’m very nervous. I’m afraid it will hurt, or even cause me to bleed. I’m also nervous that I won’t like it but he will and that this may cause friction in our relationship. Finally, is it really possible for me to experience pleasure this way? Several of my girlfriends have done it and none of them list it as their favorite thing. Isn’t anal sex all for the benefit of the one on top? I need both practical and emotional advice.

He Said: I think this question calls for a good bullet point how-to-guide, from the practical to the philosophical:

Make sure you use plenty of lube, perhaps twice what you would normally apply to vaginal sex.

If you are not using condoms, which will make the experience much more pleasurable, make sure you both get tested for all STDs, including HIV, and have been monogamous for several months—since you are engaged, this shouldn't be a problem. Remember, STDS are much easier to transmit anally.

Create a safe environment for experimentation. Have a glass of wine to relax your body and get in the mood. Since women do not have a prostate, anal sex tends to be less pleasurable than for men. Gay men enjoy bottoming so much, in fact, that they constantly complain that there are too few tops. Nevertheless, many women, and even a few straight men, report that anal play has added a whole new dimension to their sex lives.

Douche carefully in advance (Immodium is very helpful), as there is no worse way to ruin the mood than, well, you know. It is also nothing to panic over if a slight mess does occur. That's what the shower is for. And perfume.

Make sure you’re the one in control, at least at first. Most of the discomfort comes from stretching the sphincter too quickly. Start with a finger and when that feels okay, move on to two fingers. Eventually, guide the penis into the rectum slowly, making your fiancé stay still while you move at your own pace. Once you’re relaxed, he can begin moving.

You and your fiancé need to talk this through in advance. If you don't like it—or take a while to get into it—it would be totally unacceptable to pressure you. You must have 100 percent control over your own body and activities. The fact that you are willing to give it a good old-fashioned try is more than enough.

She Said: I wanted to get some feedback from straight women, so I did a random, anonymous poll of 10 ladies, and the results varied widely. I asked them simply: How often have you had anal sex, and on a scale of 1 to 10, how much did you enjoy it? The answers ranged from “Once, and I hated it,” to “Probably 30 percent of the time I have sex, and enjoyment is between 8 and 10.” This pretty much confirms what you already suspect: You may hate it, or it may prove wildly erotic. It's typical to feel apprehensive, but rest assured that if you’re in general good health, go slowly, listen to your body, and use a lot of lube, chances are nil that you will cause yourself any real injury. We all have primal fears and taboos about this region of our body—that’s part of what makes anal sex attractive. Don’t deny your fears, but stay open to other sensations that might lie beyond them. To start, peruse The Surrender by Toni Bentley. Though it’s unlikely you (or anyone, really) will enjoy anal sex as much as she does, you can think of it as an enthusiastic guidebook to a foreign land you’re about to visit. As for practicalities, I have a few points to add to the above:

Many people do not douche, use enemas, or take anti-diarrheals beforehand. If you save anal sex for a time when you haven’t eaten a heavy meal and have had your daily constitutional, so to speak, a simple shower with soap and warm water should more than suffice.

You might want to start with a toy that’s bigger than a finger, smaller than a penis, and that vibrates. Good Vibrations carries many of them, and also has a great primer on anal sex here.

Keep in mind that insertion is probably the most uncomfortable moment in the entire act. Once you relax, the sensation will change and likely become much more pleasurable. Though women don’t have a prostate, we do have several nerves that run directly from the clitoris to the rectal area.

Lastly—and most importantly!—stimulating your clitoris during anal sex can make a world of difference, not only relaxing the surrounding muscles but multiplying your pleasure. A gentle vibrator that you can hold is the perfect adjunct; and if you start with that, transitioning into penetration will prove much easier.

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