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

“Anal sex hurts for quite a lot of women,” explains Men’s Health Sex Professor Debby Herbenick, Ph.D., who helped conduct the Indiana survey. (She’s also the author of the Good in Bed Guide to Anal Pleasuring.) In fact, roughly 70 percent of women Herbenick polled for the survey reported feeling pain during their most recent anal sex episode. “So 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 stresses.

From the first conversation to the act itself, there are steps you can both take to lessen your partner’s discomfort and make the whole experience pain-free and fun for the both of you.

1.Have “the talk.”

Broach the subject of anal 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—like 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 girl expresses interest in anal, 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.
“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 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 and fondling your girl’s behind and anus. “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 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 fooling around, Cadell advises.

5. Grease the tracks.
Herbenick’s classroom research at Indiana has revealed a lot of people who try anal don’t incorporate any lubricants. “No wonder it hurts!” she says. To ensure everything goes smoothly, Herbenick recommends using a water- or silicone-based lubricant to reduce pain and chaffing—for your partner and yourself.

 6. Build yourselves up.

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 or your penis. This will help your partner become accustomed to the new sensations while readying herself for the main act. You could even spread these activities out over several nights to help her adjust to the newness, Cadell adds. Also, be sure to try various positions so you can find ones that are most comfortable for the two of you, Herbenick suggests.