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Back when the ladies of Sex and The City discussed anal sex, it shocked audiences. But since then butt play has been shown on Girls, hinted at on The Mindy Project, and rapped about by Nicki Minaj—to name just a few pop culture references. So perhaps it's not so taboo anymore.

The stats seem to support this theory: Between 1993 and 1995 only about 9 percent of women and men reported having entered through the back door within the previous three months. Heterosexual anal sexuality and anal sex behaviors: a review. McBride KR, Fortenberry JD. Journal of sex research, 2010, Jun.;47(2):1559-8519. Today more than 20 percent of women ages 20 to 39 and men ages 25 to 49 report having had anal sex in the last year. Sexual behavior in the United States: results from a national probability sample of men and women ages 14-94. Herbenick D, Reece M, Schick V. The journal of sexual medicine, 2011, Feb.;7 Suppl 5():1743-6109.

Regardless of how, why, or when you heard about it, if you’re curious about giving anal a go, it’s important to know the facts and how to stay safe before you dive in.

First Things First

Anal sex encompasses more than just inserting a penis in someone’s anus, says certified sex and relationship coach Charlie Glickman, Ph.D. Fingers, toys, tongues, and external stimulation (i.e., massaging or tickling the outside of the butthole) all qualify as anal sex and can each be delightful in their own right for some.

Curious how this all might feel? Since chances are you don’t interact much with what lies between your bottom cheeks, other than to (hopefully) clean it as needed, begin by acquainting yourself with the pleasures this part of your body has to offer, recommends Ian Kerner, Ph.D., sex educator and author of She Comes First.

“To get a sense of what anal play with a partner will actually feel like—and what you’ll most enjoy—experiment on your own during masturbation with a butt plug, vibrator, dildo, or simply your fingers,” he suggests. Toys fit for this very task can be found on websites like or at sex shop.

The upside of anal for men, of course, is stimulation of the prostate gland, an erogenous zone that fills with fluid during arousal and, when properly prodded, can enhance and even precipitate an orgasm, Glickman explains. And ladies may find the sensation to be just as toe-curling.

“Many women say they can experience orgasms from anal stimulation,” Kerner says. (For proof, check out Toni Bentley’s memoir-length testimonial.) “But most need clitoral stimulation.”

Glickman explains that pressure inside the rectum may stimulate the internal ends of clitoral nerves in some women, bringing them to climax. For others, the excitement and arousal from exploring a new territory, plus the actual internal or external sensations, may help push them over the brink. And since studies indicate that women who incorporate multiple kinds of sexual behaviors into their between-the-sheets routines are more likely to get off, if a woman massages her clitoris during anal sex, it may also help her orgasm and even have stronger than normal orgasms. An event-level analysis of the sexual characteristics and composition among adults ages 18 to 59: results from a national probability sample in the United States. Herbenick D, Reece M, Schick V. The journal of sexual medicine, 2011, Feb.;7 Suppl 5():1743-6109.

Talk to Your Partner

Gay Couple Walking Dog If after solo play you decide you want to bring your partner in on the fun, Glickman strongly advises inquiring about his or her interest anywhere but the bedroom. “Anal play should never be a surprise,” he says, adding that your partner may be inexperienced, hesitant, or simply caught off guard by incorporating an uncharted area of the body into their sexual routine. You can avoid potentially adverse reactions, discomfort, and breaches of trust by broaching the topic in a nonsexual setting.

Open with something like, “Would you ever be interested in anal sex? It’s something I’m curious to try, but I want to gauge how you feel about it.” Or, “I read this article on Greatist about anal sex. Would you ever be interested in trying something like that with me?”

If your partner isn't game, do not pressure him or her. Not only can this shatter trust between partners, it can also increase stress levels and cause the muscles around their anus to tighten, thereby raising the risk of experiencing pain during penetration, Glickman cautions. And if you're the one who's not interested (tonight or at all), don't ever perform anal sex because you feel like you should or you have to, Glickman adds.

But Won't It Be Messy and Hurt?

The first time you have anal sex, it's common to worry that you may, um, have an accident during the process, Kerner says. “But as long as you’ve gone to the bathroom within the last 3 to 5 hours, you can pretty much assume your rectum is going to be clear,” he says. And those rumors about butt play making you lose control of your bowels? Not true, Glickman says (at least there’s no medical evidence that it does).

However, like all activities involving exchange of bodily fluids, hygiene is of utmost importance. Soap and water should suffice to wash the skin of your bum, says sexologist Jessica O'Reilly, Ph.D.

For those who are extra concerned about rectal cleanliness, Kerner suggests using an enema, which you can find at most drugstores. Using the standard saline or mineral oil solution will likely lead you to use the bathroom, but just using warm water can suffice as a simple internal rinse to empty out your system, he says.

Once play time rolls around, Glickman advises placing a dark towel on whatever surface you’ll be having anal sex on and keeping some baby wipes or a wet paper towel within reach. So long as you’ve gone to the bathroom, cleaned up afterward, and haven’t made any radical changes in your diet within the past 24 hours, you won’t likely have any accidents, he says. “However, if you make anal play a regular part of your repertoire, sooner or later, sh*t might happen. Bodies are unpredictable.” (Hence why having anal only with someone you trust and can communicate with is so crucial.)

Also note that the tissues lining our rectums are more susceptible to certain disease organisms, which means anal intercourse carries a slightly higher risk of sexually transmitted infection, says Dennis J. Fortenberry, Ph.D., a sex researcher and professor of pediatrics at the Indiana University School of Medicine. To be safe, use a condom during anal intercourse. And if you’re exploring the bum with any other parts of your body (fingers, tongue, etc.), take advantage of gloves and dental dams as an extra precaution.

Bacteria from the rectum can also cause bacterial vaginosis (BV), an infection marked by a foul odor and excessive discharge. Though this condition can be treated with antibiotics, save yourself the discomfort by showering and switching condoms if transitioning from back to front.

Now for the Fun Part

Man and Woman Kissing in Bed Before inserting anything—fingers, sex toys, a penis—into the anus, Glickman recommends at least 10 to 15 minutes of foreplay. Think: blowjobs, intercourse, vibrators, or other toys. (Dirty talk counts too.) “Do something that’s already familiar and you know you both enjoy,” Glickman advises. “The more aroused we are, the more relaxed the muscles around the anus become.”

Because the rectum doesn’t self-lubricate like other areas of the body, it can get dry quickly, Glickman says. The key to preventing any pain is to keep things well oiled by using a lot of lube. He and Kerner both recommend silicone-based formulas, which are less likely to dry you out than water-based ones. (Wet, Swiss Navy, and Sliquid brands are good places to start.)

In addition to lube, if you’ve never experienced anything in your anus other than what’s exiting it, you’re going to have to take it easy. For positions, Kerner recommends missionary with an “adjusted” point of entry (i.e., receiver on his or her back) or a gentler doggy-style where the person doing the penetrating stands or remains steadily upright on his (or her) knees holding his penis (or her strap-on), while the receiver gently backs up (on hands and knees) into the object of insertion. Letting the receiver control the movement is key here.

Keep in mind that the goal of your first few attempts to have anal intercourse shouldn’t be achieving orgasm, Kerner says (though if that happens, all the better). Rather it should be about experimenting, establishing trust, and making sure everyone’s comfortable. Stop anytime you desire; and remember that whatever happens, you never have to have anal sex again if you decide it's not your thing.

The Takeaway

Anal sex isn’t solely constricted to inserting a penis in someone’s rectum. It encompasses a variety of potentially pleasurable behaviors, from fingering and prostate massages to oral contact or just external manual pressure. If anal play is something you want to try, talk to your partner in a nonsexual setting about how to get started—and please use these tips as a guide. If you’re not into it, do not feel pressured. Always remember to communicate clearly with your partner and never say yes to anything you don’t want to do, even if it's something you have tried in the past.

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