Anal Sex Primer: Expert Tips for Your First Time

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For first-timers, anal sex may seem scary, unapproachable, unsexy, overwhelming, and maybe even a little confusing when it comes to pleasure and pain for the receiver. That’s why, Lawrence Johnson, co-founder and CEO of Pure for Men, advises the best thing to do to prepare for anal sex is self-play: “You’ll want to know and push your own limits so as to leave little doubt about what feels good, what hurts, and what works before bringing a teammate into the field.”

This is particularly significant for the receiver or receptive participant (we’ll talk about the insertive partner shortly). As the receiver, this starts by settling into a place where you feel safe and comfortable for self-play then simply use your fingers to start stimulating the rear. Sexologist Caitlin V. Neal recommends starting with a dry finger gently resting on the anus. Once you’re comfortable (and a little turned on), try circling the anus with a wet finger. If all this continues to feel good, it’s time to get lube involved (a viscous lube like silicone or water-based is long-lasting, which decreases reapplication). Lube up a finger and slowly penetrate with that finger; feel how the anus relaxes and perhaps insert another finger. If this is all still pleasurable, Neal recommends getting a toy involved. “Gradually working up to larger items, including a penis, will help the receiving partners have a better experience.”

While you can experiment with this type of progressive masturbation in one sitting or work up to it over a number of days, taking your time is key. Fabian Prado, co-founder and CMO of Pure for Men, reminds us, “that part of the body is not used to having things inserted, but as most will find, it can bring great pleasure.” Prado suggests butt plugs (try B-Vibe) as training tools that can help in anal exploration while toys like dildos can allow you to control your own pace to replicate a penis.

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“An often unshared secret about receptive anal sex is that sometimes the sensations are reversed. Many people find that the same muscle contraction we use when ‘pushing’ on the toilet is the same one that helps your body ‘receive’ during anal sex,” says Johnson. “So do the same thing during the insertive part of the process and you can reduce or eliminate pain/discomfort. It takes some getting used to!”

How to Approach the Convo: Talking to Your Partner About Anal Sex

Once you have an understanding of your likes, tolerance, and the way that anal orgasms work, you may want to start incorporating it into your sexual routine. If you’ve never talked to your partner about anal sex, Daniel Saynt, founder and chief conspirator of The New Society for Wellness (NSFW), a sex- and cannabis-friendly private members club in NYC, recommends “preparing for the conversation by asking for a safe, non-judgmental space to talk about sexual desires.”

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“Don’t be pushy,” emphasizes Searah Deysach, sex educator and owner of sex shop Early to Bed. If you’ve taken the proper time to explore your own desires and needs around anal sex, you can “explain what turns you on about it and how much you want to explore it with them in particular,” she says. Deysach also suggests using this conversation as an opportunity to find out what new activities your partner might be interested in. And if you’re still nervous, Prado suggests sending your partner content and videos on the topic to help broach the subject. Along those lines, Neal recommends posing it as a question: “I saw a movie the other day, or I read an article the other day about anal sex, is that something you’d be open to try?”

If your partner is receptive, you likely aren’t going to pounce and perform anal sex right away. Set a day and time for this exciting new concept; many partners like to prepare for anal sex with a certain diet the day before and day of, as well as a cleansing routine (to make things less messy).

“Because many people are concerned about feces, limiting your diet on the day that you plan to have anal sex can help reduce any uncomfortable experiences. The anal cavity doesn’t actually hold feces—it’s stored above in the colon—but it can still be nice to eat a diet high in fiber and low in fat and animal products the day of and the day before,” says Neal. If adjusting your diet seems like too much work, you can add a fiber supplement like Pure for Men and Pure for Her to ensure digestive cleanliness.

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In addition to diet, the receiving partner may perform a water enema. If you decide to do this, however, “leave time [about an hour] between your douche and the sex to allow your butt to recover a little,” Deysach says.

Lastly, before you even get in bed (or wherever you might experiment with anal sex with your partner), Neal wants you to remember that although you might have an enlightening experience, that doesn’t mean it’s going to translate with a partner. “Go into your first anal sex experience with high hopes and low expectations,” she says. “You don’t have to achieve full anal penetration, thrusting, ejaculation on the first time…you likely won’t.”

How to Make Anal Sex Safe

Start with traditional foreplay, then direct that foreplay to the anal region and anal stimulation. If things feel comfortable, maintain that stimulation “to get really turned on, close to orgasm,” says Dr. Lori Beth Bisbey, psychologist and gender, sex, and relationship diversity therapist, and intimacy coach. This will help the entire body relax. Since the anus is not self-lubricating, lube will need to be applied, and if you want to reduce friction even further, use a condom. Though some experts recommend desensitizing lube, Deysach recommends against relying on creams with a numbing effect as “pain is your body’s way of telling you to stop or slow down,” which is essential during anal sex.

Neal says most first-timers start anal with the receiving partner on all fours, which allows them to control depth and pace. Insertive partners should go slow and listen to the receptive partner; Johnson says, “don’t you dare just stick it in,” as that can be painful and even dangerous.

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When the receptive partner’s muscles are warmed up and relaxed, Johnson warns the receptive partner should try not to climax too early, as continuing on may make receiving less than enjoyable. That’s why he refers to anal sex as an “art.” If you’re mastering the basics and want to get more toys involved, additions like cock rings for the insertive partner may increase performance time, while beads and clit vibrators for a receptive partner with a vagina enhance the experience and can lead to a double orgasm.

Important to note: Never switch between the anus and vagina without thoroughly cleaning the penis, as this can cause infection, Bisbey says. Cleanliness is a factor throughout the sexual experience, and when you’re finished, Neal says using pre-moistened wipes are a quick way to clean up the extra lube and any mess, before hopping in the shower to refresh and unwind.

Lastly, if the experience was or wasn’t enjoyable, the most important thing you can do with your partner is communicate what you did and didn’t like to ensure you’re on the same page about trying anal again or, perhaps, deciding it’s not for you.

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