Everything You Need To Know About First-Time Anal Sex

Illustrated by: Natalia Spotts
Anal sex can be one of three things: terrifying, terrible, or terrific. Maybe you’ve heard horror stories (thanks, Tucker Max) and you’re not even remotely interested in letting something, let alone someone, go up there. Perhaps you’re tempted, but you don’t know where to begin. There are reassuring, pleasurable ways to go about anal sex, though, and it can be glorious if you know what you’re doing — and so preparation is key.
"It's not as easy as it looks in porn," sex psychologist David Ley, PhD tells Refinery29. "If you try to do it the way most porn does, it will be like learning to shoot from watching Steven Seagal movies: Somebody will get hurt."
Step away from the porn, and set aside your worries and fears about the back door. All you need is this step-by-step guide to having comfortable, communicative, and mutually satisfying anal sex, which we'll be updating regularly. Click through, then go forth without fear — and have fun!
The gap between what we learned in sex ed and what we're learning through sexual experience is big — way too big. So we're helping to connect those dots by talking about the realities of sex, from how it's done to how to make sure it's consensual, safe, healthy, and pleasurable all at once. Check out more here.
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One of the best ways to prepare for partnered penetrative anal sex is to first explore anal play by yourself. Tantric sex coach Devi Ward suggests starting out by inserting one finger into your anus using plenty of lube. When you've become comfortable with a small finger, move on to toys. "Anal beads can be a nice size for beginners," Ward says. "You get a nice stimulation when you pull them out one at a time."
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Rimming refers to performing oral sex on your partner's butthole. You might have also heard it referred to as salad-tossing or analingus. While rimming is delightful on its own, it's also an excellent form of foreplay to warm up for penetrative anal sex. If you're looking for a rimming technique, Jessica O'Reilly, PhD, a Toronto-based sexologist told Refinery29 about a move called "tongue twister," in which you spread apart your partner's butt cheeks using your hands and twirl your tongue in circles around their anus.

As with any form of anal play, since the rectum harbors bacteria from the GI tract, just make sure that the receiver washes up with water before rimming.
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Sex expert Kenneth Play says that an optimal position for first-timers is spooning. "Spooning allows intimacy, visibility, and keeps your hands free," he says.

Traditionally, the person doing the penetrating is in the big spoon position, but they can also be up on their knees while the little spoon stays down (that way, you can maintain eye contact).

"It can be helpful to have the little spoon spread their butt cheeks so you can get better lighting on the anus to get the correct angle of penetration," Play says. "A lot of anal penetration is about alignment, so getting the right angle from the get-go can make a huge difference in your experience."

One anal "sex hack" Play recommends is for the little spoon to open up their sphincter (by pushing with the same muscles they use to poop) once the strap on or penis is right outside the opening.
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If you have a vagina, adding clitoral stimulation can help you relax and reach orgasm during anal sex. You can incorporate this into foreplay or during penetrative anal sex, and either you or your partner can take the lead on this one (ain't no shame in taking matters into your own hands).

Not sure how to stimulate your clit for maximum pleasure? Try the DJ method, in which you flatten a few fingers and rub your clit in circular motions, or try moving your hands in a more diagonal motion if that feels better. (And don't forget to check out our handy guide on clitoral stimulation if you're still unsure about how to go about it.)
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If you're someone who lives in a legal state and enjoys using cannabis, consider adding it to your anal sex routine. Studies suggest that cannabis can increase physical sensation, which could heighten the pleasure butt play already provides. If you're uninterested in getting high but curious about the benefits of combining cannabis with anal sex, you can try a cannabis-based anal suppository like Foria Explore. The makers of Foria Explore claim that it promotes relaxation and increases blood flow without getting you stoned.
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Illustrated by: Natalia Spotts
Since the receiver has good control over depth and speed of penetration when on top, sex and relationship coach Charlie Glickman, PhD, author of The Ultimate Guide to Prostate Pleasure, says that position is a good way to get started. Don’t be afraid to try other positions, though. “Missionary works well if you put a small pillow under the receiver’s hips to lift them up a bit,” he says. “Or have them at the edge of the bed and the giver can stand on the floor.”
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Illustrated by: Natalia Spotts
Just as with other kinds of sex, make anal sex an experience that addresses the whole body, not just the anus. Don’t forget about other erogenous zones, including nipples, clitoris, testicles, and so on — in fact, many people with clits find that anal-clit stimulation combination explosively orgasmic. Anal play as just one part of lovemaking.
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Illustrated by: Natalia Spotts
Regardless of what you’ve heard about or seen in porn, anal is not about forcing. The receiver, rather than the giver, sets the pace. If anyone is experiencing discomfort, slow it down! You also don’t need to insert the whole length of the penis or dildo. It could be that half is the perfect amount.
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Illustrated by: Natalia Spotts
According to Kyla Black, a sex therapist and clinical social worker, there's really no right amount of lube: “It very much depends on the person who will have lube on or in their body,” he says. Err on the side of excess, since the anus doesn’t self-lubricate, and choose the right lube. Avoid lubes that contain parabens, phthalates, or propylene glycol, and keep in mind that silicone-based lubes generally last longer than water-based lube: “The anus is a mucosal membrane, which means that it absorbs water rapidly and will dry out water-based lubes,” Bogdonoff says.

However, if you’re using toys, make sure to only use water-based lube with silicone toys and be careful with oil-based lubes, which can cause condoms to rip or deteriorate. Bogdonoff recommends Pjur Backdoor, a silicone-based lube that contains jojoba to increase the skin’s flexibility and softness.
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Illustrated by: Natalia Spotts
There are a ton of ways to prepare for anal penetration, including using vibrators, rimming plugs, anal beads, and even dildos. These will not only open the anus but also arouse you before penetration. Sex and relationship coach Charlie Glickman, PhD, author of The Ultimate Guide to Prostate Pleasure recommends using a vibrator to learn to relax the anus; be sure to use one made with a body-safe, non-porous material and a smooth, flared base to prevent it from going too far into the anus. Glickman suggests b-Vibe’s Rimming Plug, which takes the technology of the famous rabbit vibrator and adapts it for an anal toy.
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Illustrated by: Natalia Spotts
Anal has long been tainted with stigma and fears — that it’ll hurt, that something will go wrong, that you'll poop in the middle of it. But the shame surrounding anal sex "assumes that anal sex is unhealthy and should be rare," Ley says. "That’s a morally-based assumption, not a scientific or medical one." The best way to bring up the idea of anal sex to your partner is when neither you nor your partner is aroused. This way, you can talk about it without feeling pressure to do things too soon or in a way that feels rushed.
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Illustrated by: Natalia Spotts
With new sexual territory, boundaries are key. "It can be helpful for both partners to be aware of each other's’ 'dos and don'ts' and anything in between," says Black.

Ley suggests broaching the subject by discussing anal play as part of your sex life. "Discuss including anal stimulation in a variety of ways, with fingers, toys and tongues," he says. "This is how a couple can introduce the anus as an area of pleasure and sensation, without jumping too quickly to the theoretical finish line of penis-in-anus sex."
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Illustrated by: Natalia Spotts
In order to keep things comfortable, you’ve got to continue the conversation. Ley says that couples should be aware of each other’s fears around any new sexual behavior, especially one that’s often associated with pain. He suggests broadening the conversation so you and your partner can avoid anything that could hinder the pleasure of anal.

"When [people] believe their first experience with sexual intercourse will be painful, it often is. When they don’t believe that, it isn’t," Ley says. "The difference is the expectation, and the psychophysiological connections with that expectation. If you think anal sex is going to hurt, you prepare for that, tighten up in fear, and it does. If you prepare to enjoy it, negotiate it, prepare your body for it, and discuss ways to manage the experience, then discomfort is absent or greatly lessened."
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Illustrated by: Natalia Spotts
Whether anal sex is new for you or not, every partner will be aroused differently and will have different levels of experience. "This may be an easier conversation than you expect, but a lot depends upon sexual characteristics of the couple," Ley says. "If you’re a couple that has limited sexual experience and only ever has sex in missionary position with the lights off, then it’s going to be a much more challenging conversation."

Bogdonoff says that anal, like all sex, is part psychological and part physical. "The anus will naturally relax, making insertion easier, when you're relaxed and aroused," he says. Talking to your partner about how you want to warm things up for both of you will help you both relax.
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Illustrated by: Natalia Spotts
Make sure you both are aware that the person on the receiving end of anal sex might have a bowel movement, or that fecal matter might otherwise make some sort of cameo in your sex. There aren’t exactly numbers out there on how many people experience a bowel movement during anal, but it does happen — and the best thing is to agree that you’ll move on from it if it does. Pooping is normal, and no one can control what comes out of the anus, says Bogdonoff. "The worst thing that can happen to someone during sex is that they're shamed for have a normally-functioning body," he says.
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Illustrated by: Natalia Spotts
Some research has suggested that giving unprotected anal intercourse with a penis can increase the risk of a prostate infection from bacteria getting into the urethra, Glickman says. And of course, unprotected anal intercourse is much riskier for STIs because of how delicate the rectum is. The FDA states that condoms are more likely to break during anal intercourse than vaginal “because of the greater amount of friction” — all the more reason to relax and prepare with foreplay and lube.
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Illustrated by: Natalia Spotts
If your bowel movements are generally solid, you should be fine. If you have loose stools or are really concerned about fecal matter, consider avoiding lots of fiber before anal in order firm up your stool. Otherwise, just use the bathroom beforehand and gently scrub around the anal area to ensure you don’t have to deal with any errant flecks of fecal matter (no enema required!).
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Illustrated by: Natalia Spotts
“When you hold your breath, as lots of people do during sex, the anus tightens up,” says Glickman. Mindful breathing will not only help calm you down mentally, it’ll relax the anus, making it much easier to start any insertion or even anal play. Tensing up the entire body, including squeezing the anus, is directly linked to stress, so Glickman suggests trying breath work to quell anxiety. Partners should try to breathe together, which will not only make things easier but more pleasurable, too.
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Remember the cardinal rule of anal sex hygiene: Never ever go from anal to vaginal intercourse without washing up first. “Transferring the bacteria that naturally occur in the GI system into the vagina can cause serious problems,” Glickman says. “And just changing condoms isn’t enough, since condoms often don’t cover all the way down the shaft.” Wash the penis or toy with soap and water after anal play to remove any lube or body fluids before switching to vaginal sex. “Or even better, save anal for last,” Glickman says.
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Anal sex in porn is often depicted as hardcore banging from behind, but it can actually be slow, sweet, and filled with love. If rough anal is making you anxious, know that it only has to be as fast or slow as you want — you set the pace. Especially in positions that allow for eye contact, such as missionary, when done properly, anal sex can be a very romantic sex position.
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Yes, you can come from anal. The anus happens to hold the second highest concentration of nerve endings in your body. Vagina-possessing receivers also have a perennial sponge, which sits between the anus and the vaginal opening, and is part of the "internal network of erectile tissue" that contributes to your sexual pleasure, Ward says. All of this means that anal penetration stimulates your G-spot from new, highly sensitive angles, making an orgasm much more plausible than you might think.