How to Have Great Anal Sex, According to a Buttload of Porn Stars

Load up on lube, communicate, and above all, realize it's not for everyone.

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Sep 21 2018, 7:25pm

Illustration by Lia Kantrowitz

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In case you hadn’t noticed, hetero anal sex is, like, huge right now. Just a few decades ago, outside of queer circles, it was seen as a taboo act that only about a tenth of men and a quarter of women would cop to researchers to having tried at least once. Now, anal is a fixture of mainstream pop, not to mention porn, culture. In truth, not many hetero men or women try it, much less on the reg. (CDC data shows about a third of hetero women have ever tried anal; the number who regularly engage in it is unclear, but likely much lower. Data on hetero men experimenting with anal stimulation is hard to find, although prostate massager sales have grown rapidly of late and some reporting indicates rising interest.) Still, many sexually active folk, especially hetero women, reportedly feel pressure to dip a toe into butt stuff.

Fortunately, sex educators have met this rising demand with a wealth of how-to guides and things to keep in mind for those exploring anal. Unfortunately, many people dive right in without doing much research. That means, what little anal education many first timers have often comes from porn, where anal is often portrayed as easy: just shove an unlubricated toy or peen up an asshole, with no preparation, and pump hard for, like, an hour.

But porn anal, most in the adult industry will gladly tell you, is a fantasy. “Girls train their assholes in order to take the kind of crazy poundings they take on film,” says Skylar Snow, an adult performer who entered the industry last year. That training and prep is different for everyone, but usually it involves acclimating anuses with fingers or toys for hours or days before a scene, and using relaxation tricks. Some take supplements to keep their BMs regular, fasting, popping Imodium, and doing at least one enema in the half-day or day before a scene to minimize the risk of a fecal mishap. “The controlled environment of porn really does help,” says Joseline Kelly, who entered the industry in 2015. "Because, OK, I know I’m going to have anal with this person over here and at this time, so you just feel 100 percent ready” in a way you often can’t in real life.

“I have a pretty good system down,” adds Audrey Hollander, a 14-year porn vet known in some circles as an extreme anal queen. “I can’t honestly think of all the things that have been up my anus,” she says. “But it still takes me about three or four days of prep before I can do an anal scene.”

During filming, they take cut breaks to apply lube, rarely shown on screen, address messes, and switch from anal back to vaginal sex without showing pre-switch cleaning, which is vital to avoid infections. They also, says self-described “aspiring anal queen” Della Dane, who entered porn last year, “do certain angles and positions for entertainment value that you wouldn’t normally do.” And rather than being ready for anal at any time, stars often need to take breaks of a few days or weeks between a given number of anal shoots. All-in-all, the eight-year industry vet Cherie DeVille told me last year, “you can’t expect your female partner at home to just be able to jump into” anal, especially porn-style anal; the same applies to men and non-binary folks as well.

Yet people do. “Most civilians just think they can replicate what they see in porn,” says anal pro Charlotte Sartre. “They fuck me way too rough because they only see the jackhammer fucking in the scene.” This rash anal and porn education may help to explain why, as Kinsey Institute sex researcher Debra Herbenick told me last year, “about 70 percent of American women report pain during their most recent experience of anal intercourse—quite a bit of it moderate to severe.” It may also account for anecdotal reports of increasing numbers of women suffering anal sex injuries, like tears or prolapses, often caused by overly-tense or rough play.

That is a shame, because not only can anal sex be done safely, with no or minimal risk of injury, but it can, in theory, be fun for everyone. The opening of the anus contains tons of nerve endings in people of any gender; it is also close to the "legs" of the clitoris and the vaginal g-spot, and allows stimulation of the prostate, for those who have that anatomy. “I’ve found that I love anal orgasms and get really turned on by gaping,” says Snow. “An anal orgasm is intense for males, making their whole body quiver, or in some cases causing a man or trans woman to ejaculate without ever touching themselves,” says prominent trans porn star Kimber Haven.

Even if the anal they do on screen is hardly realistic for most people in everyday life, though, porn stars (like other sex workers) still have gobs of experience with back door play. (“I know my insides pretty well,” the anal queen Mandy Muse told me, “considering I’ve gone pretty far up and touched them.”) Sure, they sometimes have nasty accidents, or suffer horror stories. And, barring one or two like Kelly, who says that in her personal life she likes to “be ripped around and stretched to the core in an anal Olympics session” like she is on screen, most say they don’t do it nearly as often in their personal lives, and certainly not as hardcore or for as long as they do in scenes. But they know anal, and are happy to share tips for how to do it well.

Not all agree on how to do anal in real life. They are unanimous on the value of a ton of lube and gradual exploration. But some stars believe in a degree of prep work even in real life, while others believe it can be done well spontaneously, in the heat of the sexual moment. And not all of their advice will be relevant to everyone, as every asshole has different needs and levels of resilience. Stars like Sartre and longtime anal expert Joanna Angel, for instance, feel like their vaginas fatigue from frequent or rough sex faster than their asses; Angel told me her body seems so well built for anal she doesn’t need to stretch even to prep for hardcore scenes. Other people, DeVille cautions, may be at higher risk of injuries than others. And most of the adult stars I’ve spoken to over the years about the topic agree that, for some people, anal just might not be a good fit. But the advice they offer below on how to approach anal sex, especially as a beginner, is a great jumping off point for individual exploration into the great anal beyond.

What should someone exploring anal play for the first time try, or consider before diving in?

Anastasia Rose : I always recommend starting with toys. There is a five-step silicone butt plug kit I highly recommend. It’s on Amazon! But also, vibrating anal toys! Try them, I promise you’ll be an anal slut in no time. I also recommend maybe starting with one finger, then two, then maybe three. The key to all of this is just to relax. Breathe steadily. Trust yourself. And if it hurts, stop.

Skylar Snow: There are lots of great toys out there to practice and play with. So see what you like.

Whitney Wright : There are so many fun, different anal toys! Inflators, glass toys, anal beads, butt plugs, dildos.

Kimber Haven: Only put things up there that are either a dick, or designed for anal play. [ Note: This means toys with flared bases so the sphincter can’t suck it entirely inside of your anus.] Every doctor can tell you a story of someone experimenting [with] sticking stuff up there that shouldn’t be in there.

What do people need to know about using anal toys to experiment with, or prep for more anal play?

Kimber Haven: If you’re not experienced, go slow and don’t pick a partner or dildo that’s, like, eight inches for your first anal. Start small, like experimenting with a toy around five to six inches at the start.

Stephanie West : Use anal training toys the right way. Smallest-to-biggest. Don’t leave them in for more than 10 minutes each.

Della Dane: I personally don’t enjoy butt plugs, nor do I need them to prep [now]. But I know lots of people who do. Find what works for your body and be willing to explore and try different things.

What do people trying to have good anal need to know about lubrication?

Skylar Snow: Pick a lube that you like (I like coconut oil) because you're going to want a lot of it.

Audrey Hollander: Even if you think you have enough lube, use even more. [ Note: Some experts argue that using too much lube can encourage anal play that’s too fast, causing unintentional injury.]

Stephanie West: There are certain lubes for anal rather than regular lube. [ Note: These are usually thicker silicon or silicone-water hybrid lubes, which reduce friction.] They are available all over the internet.

Joseline Kelly: Do not use silicone lube with silicone toys, though. With time, they will disintegrate.

Miranda Miller : Don’t use water based lube. It dries up much quicker [than silicone based lube].

Beyond the physical act, how should people looking to do anal broach the idea with someone they're intimate with?

Anastasia Rose: Try starting out with someone you trust.

Whitney Wright: When you finally get to the point right before trying anal for the first time, make sure you communicate with your partner what feels good, and what pace you would like them to go at.

Ryan Driller : You have to have a lot of discussion with your partner to see if they’re open to it. Actually into it.

Tori Avano : I need amazing chemistry with my partner in order to be able to do anal. No vibes, no anal. Also, the main thing is communication with a partner. Without communication it’s not going to work.

Is cleaning or an enema absolutely necessary if you want to do anal well?

Della Dane: I don't always prepare for it—cleaning out, enemas, etc. But I also usually do anal with partners with whom I feel comfortable communicating, and sharing a possibly messy experience.

Anastasia Rose: Some [people] feel more comfortable and confident if they clean out with an enema first. Try that first if you want. It starts to give you a feel of something in your ass.

Kimber Haven: It gets messy [if you don't clean]. If you’re the bottom, you won’t enjoy it, because you won’t be able to relax and enjoy yourself if you don’t feel clean.

Miranda Miller: Make sure you clean out. I would hate for anyone to have an accident their first time. Always use water enema and never saline. It’s better for your body that way

Whitney Wright: I always enema with warm water, and clean out an hour before. [Note: Some worry enemas can irritate the colon , leading to short-term GI tract issues and a greater disease transmission risk.]

Skylar Snow: Don’t worry if you’re not perfectly clean. It happens.

Ryan Driller: Know there’s [often likely] going to be some mess. Make sure that you [and your partner] are comfortable with that, so that you don’t kill the vibe with freaking out, or by worrying about it.

Sarah Vandella : Don't eat heavy before anal. Drink lots of water to flush your system.

Kimmie KaBoom: I would recommend not eating any hardcore meals 12 to 24 hours before anal to keep it clean.

What do people worried about initial pain, maybe considering numbing agents or painkillers, need to know?

Ryan Driller: Do not use numbing agents! This can mean a handful of Tylenol, or Analeze or abnesol. You need to be able to feel if something really doesn’t feel right or good, so that you don’t hurt yourself. Not to mention, you’ll numb his cock too, meaning no more boner.

Kimmie KaBoom: I also am against people using poppers or pills to relax muscles for the same reasons. [And] remember to practice safe sex, because STDs can still be transmitted anally, too. [Note: The fragility of anal wall tissue makes micro tears more likely, increasing the risk of sexually transmitted disease transmission significantly versus vaginal sex.]

Sarah Vandella: If you need to take drugs for anal sex, it’s probably not the right thing for you.

Charlotte Sartre: I wouldn’t even recommend taking one Tylenol before anal, because it’s not supposed to hurt. If it does, you’re doing something wrong. Either it’s not for you or you need to adjust.

Are there any particularly good positions for anal, especially for beginners?

Skylar Snow: I find lying on my back in missionary with my legs folded back is the easiest way to take anal. Your lower muscles aren't supporting your body, so your asshole will relax more.

Anastasia Rose: Missionary is also good because you can spread your ass, making it open even more.

Kimmie KaBoom: I would experiment with positions. Riding anally and doggy can penetrate deeply. But beginners might want to try laying sideways for an easy entry and more comfortable first experience.

Are there any last precautions people getting into anal should be aware of?

Kimmie KaBoom: Anal sex does [often] feel better over time and can be very pleasurable for both parties.

Anastasia Rose: You may just not like it. It's one of those things that's not for everyone. And that's totally fine!

Miranda Miller: Honestly I do not recommend doing it everyday, especially after rough anal. The asshole itself needs four days to heal from any tearing. Once in awhile is fun. Just not all the time.

Cherie DeVille: If you have any episodes of having trouble holding your stool or, heaven forbid, if you have an accident, you need to take a break and do your anal kegels until that is not an issue anymore.

Joanna Angel: I go to a proctologist a couple of times a year just to check everything out… It’s kind of important if you’re going to be engaging in anal all the time. My gynecologist recommended I go to one. You’ve got to just listen to your body. You’ve just got to know when you’re too sore and when it’s not the right day for anal. That’s important for any kind of sex, especially for women.

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