A guide to fun, safe, shame-free anal sex

Out of all the items on the sexual menu, anal gets arguably the worst rap, an undeserved stigma that likely comes from a widespread lack of knowledge about butt stuff.

According to Alicia Sinclair—a certified sex educator and founder of b-Vibe, a sex toy company dedicated to anal play—one common explanation for squeamishness is a lack of preparedness. When people start experimenting with sex, they typically confine touching to their genitalia. This leaves out an orifice that, for many, turns out to be pretty pleasurable.

“The anal sphincter is really strong and it’s also really delicate and it has a lot of nerve endings, so it’s important to just remember, just like every other part of your body, you probably want to have a learning curve,” Sinclair told the Daily Dot. Vaginal sex tends to feel better when people play around with their own bodies before enlisting a partner, building up to penetration. Most of us don’t spend equal time figuring out what works for our anuses, though.

“When we talk about butt stuff,” she continued, “it’s kind of like, ‘Oh yeah, we just tried it one day.’ It’s from 0 to penis, there’s no investigation, no touching, no feelings, no kind of getting used to the sensation.”

One of the stories she hears most often, Sinclair said, is agreeing to anal to please a partner and ending up with a painful experience because both parties wandered into the act blind. If pain, fear, and guilt “are what you associate really early on with anal sex,” Sinclair added, “it is going to be a scary thing that maybe you’re a little bit reluctant to try.”

anal sex first time

But anal sex, despite the taboos and stigma, is something that a solid number of people have tried: According to a 2017 survey by Skyn condoms, 36 percent of millennials surveyed sometimes have “female anal sex” and 15 percent have “male anal sex.” As Cosmopolitan reported, rising numbers of young people seem to be engaging in anal sex, with 40 percent of 20-to-24-year-old participants in one study having tried anal, and 20 percent of women ages 20 to 39 having had anal in the past year. While numbers on a page can’t tell us anything about how much those people enjoyed their experience, they can at least help us gauge popular interest.

Anal sex needn’t be intimidating, nor any less safe than any other kind of sex, so long as you’re using protection. In other words, without bulletproof certainty that you and your partner are both mutually monogamous and unless you’ve both recently cleared in a screening for sexually transmitted diseases, use some kind of condom regardless of the orifice involved. Stern warning aside, here are Sinclair’s top DOs and DONTs for fun anal sex.

How to have anal sex: Dos and don’ts


Take the time to learn about anal

Do your research before you get started, reading up on any elements that might make you nervous or about which you might have questions. Don’t be afraid to use yourself as a test subject.

Sinclair suggests testing the waters while you shower. “Just taking a minute or so and putting a finger in and sort of just feeling around to say like, ‘Oh, yeah, how does this sensation feel and what would it feel like if someone was doing this to me?’” she said.

Solo play affords you the chance to be “both the giver and the receiver,” Sinclair said, a point that may be of particular importance when it comes to integrating sex toys. Naturally, Sinclair likes butt plugs for escalating anal pleasure but recommends taking yours for a spin by yourself first. Familiarize yourself with what might be a very new sensation before involving a partner.

anal sex first time

Talk with your partner before you try anything

“I totally understand, sometimes it’s hard to be like, ‘Hey, I’m interested in playing with my butt, are you interested?’” Sinclair said. “Having that initial conversation will set the tone for the entire experience, especially if you do it outside the bedroom, not in the dynamic where it’s five minutes away from having sex.”

Maybe you’re thinking, OK, but it’s not like I can just broach this topic over Wednesday night chicken in the same breath as I ask to be passed the salt. But the thing is, you can. I’d say, you should. Ask whenever you feel comfortable—this ultimately isn’t a big deal question.


Take a moment to pre-clean

As a teen and into my twenties, I occasionally heard a secondhand story about an acutely embarrassing anal-sex-induced bowel movement on some anonymous parents’ white sofa. I remember the details vividly enough that I could likely convince a stranger I was there. You may have heard some version of this same story, and you may worry that anal sex will trigger the kind of shitty interruption that becomes fodder for adolescent sleepovers from now until forever.

If you’re concerned about what your partner might find up your rectum, or if it’s been a minute since you’ve voided your bowels (Stress! Dietary irregularities! Constipation never strikes at sex-conducive moments!), or if the possibility of poop worries you, consider a pre-clean. Sinclair suggests alcohol-free baby wipes, and if you can/it makes you feel more comfortable, going to the bathroom 30-60 minutes before sex. Enemas might also appeal, but NB: Use too much water, and you might invite more mess. Sinclair recommends just a couple cups of warm water (test it on your wrist) one to two hours before anal play. Follow the instructions on an enema bulb for more specific guidance.

And, if you are using toys, please do wash them in hot soapy water between uses.

how to have anal sex

Take small steps

Many readers will be unused to an object of any size penetrating their anus. It’s an excellent idea to start small and scale up, taking the time your body needs to adjust to new sensations. Sinclair recommends starting with fingering if you’ve just begun solo play, graduating to larger-sized toys or a penis. That’s advisable whether you’re working with a partner or not. Go slowly, whether you’re giving or receiving.


Use lube!

The anus does not self-lubricate, and unlubricated penetration can translate to tears in anal tissue that make it much easier to spread STIs. Add lube, liberally, keeping in mind that water-based lubes—while great for silicone sex toys—evaporate quickly and require frequent reapplication. Coconut oil makes a good natural lubricant, but no lube can guarantee your anal skin won’t tear, so again: Go slowly.


Double dip

“The anus and the vagina are two very distinct ecosystems, and you don’t want to spread bacteria from the anus to the vagina,” Sinclair advised. The anus houses different bacteria than the vagina does and introducing microbes from the former into the latter can result in uncomfortable infections like bacterial vaginosis. When engaging in butt stuff, wash hands and genitals before switching from orifice to orifice, and use a fresh condom or gloves when changing holes.

anal sex

Surprise your partner

Consent is key to a mutually satisfying sexual encounter. With that in mind, let’s maybe abandon the shocker: As Sinclair put it, “surprising your partner with a new sexual experience is never a good idea.” Unless you and your partner have established that a finger in the butt would be welcome at some point during the sexual encounter, maybe don’t jam a digit up there, and certainly, don’t stick your dick or your dildo in anyone’s butt before they tell you it’s okay to do so.

Editor’s note: This article is regularly updated for relevance.