5 Things You Should Know About Safe & Pleasurable Anal Sex

The subject of anal sex has historically been pretty hush-hush, but a full 46% of women report they've tried it at least once.

One of my favorite references, The Guide to Getting It On by Paul Joannides, PsyD, discusses anal sex at length in a chapter aptly titled “Anal Sex — Up Your Bum.” This section reminds us that although “some couples would rather drink goat sweat than try anal sex," "two to five million straight American couples are said to practice anal intercourse with regularity, [while] only about 50% of gay males bury the weenie in the wazoo." Whatever motivates you to try anal sex, there are some rules to heed for the safety and pleasure of everyone involved.
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This curvature and overall delicate nature of the interior of your bum is why anal sex is classified as a "risky" sex act — the one layer of epithelial cells between the penetrator and your bloodstream means there's a risk of tearing and small cuts, which could lead to STI entry into your bloodstream. Whether a penis, a finger, a butt plug, or a dildo is penetrating the anus, it's helpful to remember that the rectum is curved and somewhat fragile. This means you must enter slowly and exit slowly so as not to tear anything.

Speaking of what you're using to penetrate, keep in mind that the anus, unlike the vagina, is an eager orifice that could swallow what goes in. You really can't put just anything up your butt. Seriously. You won't "lose" your favorite sex toy while penetrating a vagina, but you may lose it in the anus. So, choose your penetrative object with care; it ought to have a flared base or handle — not only so you can control the movements easier, but also so that it won't risk getting sucked up.

The best technique is to "move the outer part of the butt plug [or other preferred toy] in a circle, or up and down, instead of in and out. Slowly withdraw the butt plug, then reinsert it," writes Carlyle Jansen in her new book, Sex Yourself. Your chosen toy should also be smooth (with no ridges) to avoid potential harm, and generally speaking, glass should be borosilicate (typically used in Pyrex dishware) as it's resistant to cracking or shattering.

An important tip for playing safely with your butt is to always use lube. Although the anal cavity and entryway are lined with many pleasure-inducing nerve endings, they are quite delicate. Any lube is better than no lube, but the more viscous, the better — which is why I often recommend the silicone variety for its compatibility with latex condoms and the fact that it won’t dry out as quickly as water-based lubricants will.
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Great sex is a goal many of us share, right? A big part of this means talking about how safer sex is the best sex. Using proper barrier methods, incorporating lube, engaging in consensual and negotiated sex acts — all of these are examples of safer sex, and practicing them during anal play is a must.

Always use condoms to avoid the transmission of STIs and HIV. Aside from latex condoms, you might consider trying insertive/internal condoms (also known as female condoms), which can be inserted into anal or vaginal orifices hours prior to play; these give the receiver more autonomy in the sexual situation.

When it comes to your barrier method of choice, if you’re playing between anal penetration and vaginal, the rule here is not to use the same condom for both. That's a recipe for bacterial spread and likely infection.

If you’re into rimming or rim jobs (which is sticking your tongue up, in, and around your partner’s anus), a light anal douche prior to this play can benefit your lover when it comes to anal flavor and, more importantly, could reduce the risk of hepatitis or intestinal parasites, especially if you’re playing with a stranger.
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If you read my piece in June, which was all about orgasms, you understand the power of a blended orgasm. Experiencing a blended orgasm that integrates anal play has been reported to be at the top of many people’s "wish lists." I've heard some people insist that their strongest orgasms occurred when anal play was included, especially when clitoral stimulation was happening, too. To achieve this level of pleasure, build up towards an orgasm by rubbing your clit and simultaneously using anal beads to penetrate your anus. Right at the moment you are about to achieve orgasm, slowly pull out the beads from your ass and bring yourself to another level of pleasure.

Any orgasm that involves anal massage or penetration is unlikely to leave you disappointed. And, as Jansen writes, “Inserting a toy or fingers anally shouldn’t hurt. If it does, add lube; slow down, spend more time stimulating the outside of your anus first, to warm you up. Or, just leave it for another time.” There’s a gradualism to butt play, and if you understand that, you may be well on your way to achieving blended orgasms each and every time.
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When we think anal sex, we often think penis or penile-shaped toy inserted into the anal cavity, but there are other wonderful ways that many of us can achieve orgasm via the anus, such as anal fisting. This method can be hazardous if you aren’t safe about it (remember that thin wall of epithelial cells — rectal prolapse is not fun), and it involves a lot of lube, deep breathing, trust, and practice.

“Anal fisting, also known as handballing, is the gradual process of putting your hand (and for very experienced players, sometimes your forearm) inside someone's ass," Tristan Taormino, author of The Ultimate Guide to Anal Sex for Women, wrote in The Village Voice. "Fisting as a term is misleading since you don't go inside all at once like a punch; usually your hand is not in a clenched fist once it is in there."

Of course, we can't not talk about prostate stimulation. Located a few inches within the male rectum, the prostate can be stimulated in a couple of popular ways. A word of warning to the penetrator: “[You] should never thrust straight in — the anus curves, and he’ll simply slam into [the] rectal wall," says Alex Comfort, MB BChir in the popular The Joy of Sex. Slowly massage the area and take cues from your partner. You can go as hard or as soft as is necessary, but leave those directions up to the person whose butt has your finger lodged inside of it. Massage of the perineum — the space between genitalia and the anus — also has had positive impact on prostate health and pleasure, as it is a great indirect way to stimulate the nerve endings that surround the prostate, as well as the prostate itself.
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No matter how you identify sexually or gender-wise, know that anal sex can be enjoyed by everyone. So, let's eliminate the stigma and open ourselves up to the possibility of fulfilling and pleasurable anal sex.

Traditionally, the anus has been seen as an “out hole” rather than an “in hole,” and it doesn't help that some religions have condemned sodomy as a practice. Then there's the perpetual slut-shaming of women who enjoy sex, including anal sex — and that needs to stop.

Know that if you’re curious about experimenting or are already enthusiastically enjoying anal stimulation, you are not alone.

Embrace your body and own your orgasms. Only you can dictate what pleasure looks like in your life. Your sex life is your own, and if that involves a little anal play every once in a while (or even every day, for that matter), just be sure you are informed and make the safest decision for your sexual health.
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