According to a national sexual health survey from Indiana University’s Kinsey Institute, roughly half of all men and women have attempted anal sex. But “attempting” and “enjoying” anal sex are two different things. And for a lot of couples, the fear of discomfort — or even pain — associated with anal sex scares them away from any follow-up experimentation.

So let’s be clear: if your partner is totally not into the idea of having anal sex, absolutely nothing you can say is going to convince her otherwise, nor is it a good idea to pressure her in the first place. “If a woman says she’s not interested because she’s tried it and it hurts, or she’s afraid it will hurt, listen to her,” Herbenick says. No sex act is worth making your partner feel uncomfortable or putting her through pain. Period. End of story.

But if you’ve both expressed interest in dabbling in some backdoor action, and both of you are on the same page, there are steps you can both take to lessen your partner’s discomfort and make the whole experience of anal sex pain-free and fun for the both of you. Here are just a few of them.

1) Have “the talk.”

If you’re interested in trying anal sex, the first thing you need to do is talk to your partner about it — and like any important conversation, there’s a right and wrong way to do it. Broach the subject of anal sex at the wrong moment, and your partner may think you’re unsatisfied with your current love life.

Instead, wait until a time when you’re both relaxed — say, after dinner, or after you’ve had great sex.

“Make sure to let your lover know how happy you are with your intimate life,” Herbenick says. If your partner expresses interest in anal sex, tell her you want to hash out any concerns she may have. “This is crucial for both parties to be able to relax and enjoy the experience,” Herbenick adds.

2) Don’t drink.

You might be tempted to have a romantic glass of wine or two to set the mood. But “it’s best to try anal sex while completely sober,” Herbenick says. Why? You need a clear head so you can accurately observe and assess your partner’s mood and comfort her throughout the experience. “Stop immediately if she says to stop, and check in with her during the act to make sure she’s enjoying herself,” Herbenick adds.

3) Wash up.

Take a bath with your partner and take turns washing each other—especially your nether regions, advises Ava Cadell, a doctor of human sexuality and author of NeuroLoveology. Cadell suggests spending extra time lathering up her butt. “This is a great way to warm her up to the idea of being touched back there,” Cadell explains. A thorough cleansing will also help you both feel more comfortable with your foray into anal sex.

4) Request permission to board.

Even if you’ve agreed to give anal sex a try, don’t assume it’s going to happen the next time you’re intimate. Make sure your partner is ready and willing before you start to approach anal sex, Cadell advises.

5) Grease the tracks.

Herbenick’s classroom research at Indiana revealed that a lot of people who try anal sex don’t incorporate any lubricants at all. “No wonder it hurts!” she says. To ensure everything goes smoothly, Herbenick recommends using a water- or silicone-based lubricant to reduce pain and chafing, both for your partner and yourself. We recommend the water-based Shibari Personal Lubricant ($10.09, buy it here).

6) Build yourselves up.

You know that saying, “Rome wasn’t built in a day?” Well, the same can be said to building up to anal sex. Foreplay is crucial to any sexual encounter, and anal is no exception: you have to put in a fair amount of prep to ensure that it’s pleasurable for her.

To begin, try penetrating her with just a finger, Herbenick suggests. (And again, don’t neglect the lube!) When she gives you the green light, move on to two fingers, followed by a small sex toy. This will help your partner become accustomed to the new sensations while readying her for the main act. You could even spread these activities out over several nights to help her adjust to it, Cadell adds.



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