Sex

A Beginner’s Guide to Having Really Great Anal Sex

Whether you'll top, bottom, or both: Here’s what to know about douching, lube, and the finer points of how to ease into anal sex.
August 23, 2021, 4:39pm
How to Make Anal Sex Less Painful
Advice on the finer points of having great sex.

Whether you’re idly curious about anal sex or fully desperate to get railed for the first time, it makes sense that you’re interested in butt sex: Anal is one of the finer aspects of being alive. If you’re wondering how to best go about trying anal, let’s cover the top-to-bottom basics, from talking about it with partners to aftercare. There’s a first time for everything, and this guide will help you make your anal debut as wonderful as it can and should be.

What to Do Before the First Time You Have Anal Sex

Talk about it with your intended partner.

The best first step is to have a conversation about what you want to do with the partner you’ve got in mind. This talk will happen ideally sometime before you’re in bed together: Discussing new sexual forays outside of the bedroom gives both of you time to warm your brains up to the idea, plus reduces any unintended pressure in the moment.

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Starting the butt sex conversation with a partner is as simple as talking through what you’re curious about. As you do, be as explicit about your interests as you can to ensure both of you are on the same page—being vague can sometimes lead to mixed interpretations of what the two of you are actually asking for or agreeing to. For instance, are you hoping to top or bottom, or maybe a little of both? Want to start using butt plugs? Want your partner to strap up and fuck your behind? Want to try prostate milking? Spell it out! Don’t expect your partner to have the exact same desires you do—listen to what they want, too.

If you want to bottom, but have medical conditions affecting your control of your bowels, talk to your doctor.

Gastrointestinal conditions, such as IBS, digestive issues, chronic constipation, or Crohn’s Disease make things a bit more complex, it doesn’t mean anal sex is off the table. Patience, planning, and listening to your body are key—and so is discussing your conditions with your doctor. Listen, I recognize how uncomfortable it can be for the shy among us to talk about sex, especially sex concerning poop, with a medical professional. If that sounds like you: I’m enamored with Joan Price’s medical mantra when it comes to chatting to your doctors about sex of any sort: Price’s script spells out what to say clearly and with authority, which can sometimes be hard to know how to do in the moment.

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Address any misgivings or misconceptions about anal sex by discussing—or looking up—the facts.

No matter your gender or sexual preference: Anal sex is still sometimes associated with certain by taboos and misconceptions that some newcomers might need to work through to relax and enjoy giving or taking it up the ass. 

Yes: Anal sex is pleasurable for bottoming partners of all genders! No: Anal sex shouldn’t be painful! As you seek out information to back you up in talking through those sorts of concerns and others you might encounter: Articles like this one are great starting points, but people have written entire books that can help with other holes you might encounter as you hope to encounter new holes.

Be pragmatic about—not preventatively afraid of—the prospect of poop.

It’s best to reframe your mindset about “messiness” rather than being freaked out by what might come out of you or your partner. There are a few different ways to get ready for anal sex and minimize accidents, but shit literally happens. It’s not the end of the world. In fact, it’s a sign that you’re truly living—and truly fucking, or getting fucked, up the ass.

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In all likelihood, though, most of the butt sex you have won’t involve much more than a suggestion of shit. The way butt anatomy works is that there really isn’t much poop in the lower half of your rectum.

If you’re bottoming—and if you want, this is optional—clean yourself out in the shower or douche.

For anal play that doesn’t have a lot of depth, simply washing yourself with body-friendly soap and an exploring finger in the shower will clean your bum out enough.

If anal penetration that’s deeper than a few inches is on your to-do list, you might consider to anally douching beforehand to flush yourself out a little more thoroughly. Again, not a whole lot of poop usually chills in the lower rectum, but some can still be there. Using an enema—a tool that thrusts water into the rectum to rinse poop out—can leave you super-clean. 

You’ll want to consult a fuller step-by-step guide to learn more about enemas, but here’s generally how it works: An hour or two before you have sex, get in a warm shower with the enema. It’s important to use warm water—not hot water, which can cause scalding on your delicate tissues, and not cold water, which can cause painful cramping. Fill the enema with your warm water, use some lube on the tip of the enema, and put just that tip of the enema inside your butt. Slowly squeeze the bulb at the other end to release the water into you, then let everything come out. Do this a few times until the water coming out is clear. Once that’s the case, stop! Don’t overdo it—our bowels are sensitive. And don’t make douching too much of a habit. Anal douching too frequently can cause irritation and rid you of all the good stuff your gut produces that makes your butt happy and healthy. While there is no hard number in terms of how many times is too many times in a given period of time, educators often recommend douching no more than once a week. 

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Learn about which lube might be best for you.

I cannot—CANNOT—emphasize the importance of lube when it comes to any sexual act, but especially anal sex! Despite the glistening rectums shown in porn, our butts do not naturally lubricate! And our tissues are incredibly delicate there! We need lube before and throughout having anal sex to ensure we have the best experience. Lube enhances sensations, prevents tearing, and can make sex more enjoyable overall, for everyone. I could probably write a whole article on lube alone, but for the sake of brevity, here’s what you need to know about anal lube above all else: Keeping things slick is key. 

Annoyingly, there isn’t a single brand of lube that is going to work with every body (or every sex act). It might take a minute to find out what type/texture/ingredients work with your body and needs. Lube interacts with a body’s pH levels (yes, butts have a pH), and whatever ingredients are in the lube are likely going to get absorbed into your system as well.   

Rather than being hyper-prescriptive about one or two brands that I like best, but which might not even be compatible with you and/or a partner’s specific bodies, here’s an overview of the main kinds of lube that are readily available at sex stores and the pharmacy, including their pros and cons.

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Silicone lube typically stays slick for a longer time than water-based or oil-based lubes and are hypoallergenic. The molecules in silicone don’t absorb into your body, meaning it sits on the surface of your skin until it dissipates. (This is also what keeps silicone lube so slippery, and why spilling some on your floor sucks.) Pjur Anal Lube and Uberlube are my personal favorites. One important thing to note: Silicone lube can’t be used with silicone toys, since they can break the toy down. If you’re using a toy, pick a lube with another base.

Water-based lube has the highest chance of interacting with your body, since your body will absorb it and its ingredients, which can cause adverse affects. Annoyingly, the skin on your genitals is much more sensitive than your skin, so keeping an eye out on harmful ingredients and trial and error is the best way to find a lube that fits your bod. If you find water-based lube works for you: Sliquid Sassy has a cult following of anal aficionados who love its thick, plush feel and because it’s safe to use with sex toys.

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Oil-based lubes are often hydrating—meaning that they’re also absorbed into your skin, and so can interact with your pH. A huge caveat is that they don’t work with latex or poly-isoprene condoms, so they’re not great for anal unless you’re having unprotected sex.

Once you’ve gotten your lube—and gotten a lot of it—learn how to use it.

If you’re not used to using lube in bed, solo or partnered, in intercourse or masturbation, take a minute and get used to using it during sex before entering into anal territory. Lube should be put on every toy and part of the body making contact, on both partners: on the outside of an anus, on the toy or body part that plans to enter the anus, as well as inside the anus itself before insertion. Start by putting some of your favorite lube on your fingers and circling the butthole. (This also doubles as foreplay!) Put more lube on your finger and slowly enter inside. (More hot foreplay.)  Make sure whatever is entering the butt is properly lubed up before entering. (If you want, you can also use a lube shooter to pre-lube inside.) 

Depending on whether you’re using a silicone lube or a water- or oil-based one, lube either dissipates or absorbs into the skin. This mean it’s not going to last the full fuck session, so don’t toss the lube off the bed because it’ll be a scramble later when you need it again. Since all lube (and bodies) are different, there isn’t a set timeline for when to reapply, but if you’re paying attention, you can usually start to feel it begin to thin out or feel stickier or drier than it does slick, smooth, or wet. Also, you can and should—you will—always ask your partner if they need more lube. In my opinion, asking if someone needs lube is the same as dirty talk, and it’s always more than welcome. 

The following sentences are among the most important ones you can say to make anal sex great, and they’re certainly the ones you should find yourself using above any others (except “yes” and “yesssssss”). Repeat after me:

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– “Where’s your lube?” 

– “I need more lube.”

– “Pass me the lube.”

Fab—moving on. 

Skip the numbing cream.

Anal sex shouldn’t hurt! I’ll say it as many times as necessary! Butts take an almost annoying amount of patience and time to warm up. Some people use numbing cream to rush the process and I am here to offer a gentle word of warning against these creams. Pain is your body indicating something isn’t right, that it’s not feeling great. Numbing that pain means you can’t feel your body’s plea to stop/pause/slow down. Without listening to those warnings, the likelihood of tears, bleeding, or other painful side-effects increases. 

Try exploring butt stimulation by yourself first. 

Solo play helps get you comfortable with the sensations involved, lets you know what you do and don’t like, and can just make masturbation more fun. In the case of anal sex, it can be useful to train your butts up with toys before you try actually fucking, too.

Before you use toys, you need to learn about the intricacies of your sphincter. Around the butthole are two sphincters: one that you can control, and one you can’t. Quick: Squeeze your Kegel muscles (they’re in your pelvic floor)—you’re probably squeezing your outer anal sphincter, as well! This outer sphincter can be taught to relax and let things inside. While the outer sphincter pushes out, the inner one sucks in. The inner sphincter is more of a wild card, and why everything you put inside your butt needs a flared base: to ensure it doesn’t get sucked right up your butt. Trust me on this, it’s not a fun trip to the emergency room. 

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Now that you know where those toys are going: Solo play helps get you comfortable with the sensations involved, lets you know what you do and don’t like, and can just make masturbation more fun. In the case of anal sex, it can be useful to train your butts up with toys before you try actually fucking, too: For some people, butt plugs are the endgame. For others, they’re used to warm up and stretch your anus and anal sphincters. 

Outside of making sure any toy you use has a flared base, look for beginner plugs if you’re new. A dildo is the next phase of training after using butt plugs. They are longer and you can practice the in-and-out motion of anal sex. When you’re choosing a dildo, go for one with a flared base and that’s smooth. You don’t want any toys with bulges or ripples as that’s going to make your poor anal sphincter have to open and close rapidly. Make sure your anal toys are silicone so they can be sanitized easily (which is what you want for anything you put in your butt). 

Even if you’re more interested in giving than receiving, it’s still a good idea to play with yourself solo first. Trying out anal yourself can help you understand what your partner might be feeling. If something feels good (or doesn’t!) to you, there’s a good chance your partner might feel similar.

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When you’re ready to get your partner involved, set the scene.

Put down a dark-colored towel to keep your bed clean of any lube, fluids, and yes, poop, that might occur during sex. Even if the receiving partner showers and/or does an enema first, accidents can happen, but that doesn’t have to ruin the night or your bed sheets—you can just swap your towel for a clean one or toss it in the laundry after.

Outside of keeping your lube and toys close at hand, think about what else you might want nearby. Body-friendly wipes are nice to have near the bedside to quickly wipe off hands, bodies, and toys as you go. And, of course, use condoms to prevent STIs. 

How to Actually Have Anal Sex for the First Time

Finally!!!!

Make sure to spend time on foreplay.

Being turned on is essential for a good anal time–the more turned on you are, the more relaxed your tush gets. Your peach also probably needs a bit of lovin’ before fingers/toys/a penis can enter. Touching the butt and the anus with hands and fingers can start the night right. Light spanking and impact play can also be a great way to bring focus and feeling to the area. Rim jobs are hot... like, super hot. If you or your partner are nervous about putting their mouths on an anus, use lube and a dental dam as a barrier. 

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If you normally get off by using a vibrator, incorporating one before and during anal play is a fantastic idea in terms of staying turned on and relaxed, so you might want to make sure your favorite toy is charged before you go pound town. 

When it’s time to penetrate or be penetrated: Go slow, be careful, and talk through it.

OK: You’re on the receiving end of a toy/finger/body part that is lubed and is ready to slowly enter your butt, or vice versa! Going slow and paying attention is key. If there’s any pain, that’s a sign that both of you should pause. Add more lube if you need to, and then the receiver should focus on relaxing their outer sphincter, which can mean stimulating their genitals to make sure they’re turned on and feeling good. Then keep going and see how you do, pausing and repeating the above step if you need to.

If you’re bottoming: After the toy/finger/body part enters, you’ll feel your anal sphincters close down around it. Take a second and just get used to the sensation! Touch yourself/your partner again to keep everyone thoroughly turned on in this hot moment. If your endgame is taking a butt plug, your sphincters will close around the base and now you can move around and do any other sexual act you desire, you perv! The smaller the base, the more likely it is to stay in place.

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Incorporate thrusting with care—and figure out what speed and depth works best for you as you go.

If your encounter includes thrusting, be sure to warm up with toys and fingers first. If that’s feeling good, feel free to use a dildo or penis and get some movement going! (Some folks might find that moving from butt plug to penis is too much, too fast, in which case it’s time to put a hold on that idea and focus on doing some anal training before you try anal sex again another time.) 

If the person being entered has a prostate, a dildo with a curve (or a butt plug with a curve) can help hit the right place. If you or your partner find that they’re not enjoying the full depth of the apparatus entering their behind, try using bumpers like an Ohnut—a stack of adjustable silicone rings that can stop a dildo or penis from entering all the way inside a body—to create a buffer to prevent penetration that’s too deep to enjoy.

If you do find that anal sex is painful, don’t try to push through it. 

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Despite what you might have heard from all the schlocky, homophobic jokes you’ve probably heard about anal sex at some time or other in your life: Anal sex shouldn’t hurt! Yes, it can be a little uncomfortable as your body gets used to the sensation, but there shouldn’t be pain. If it starts to hurt, take a moment and assess the situation. If it feels like it’s stinging or there’s too much friction, lube is your best friend—dryness is usually the cause of these sensations. 

If it still hurts, and/or it feels like you can’t handle what’s inside you, it could be that your inner muscles aren’t warmed up or relaxed enough. Switch to a smaller toy or take a break from anal for the evening. Anal sex isn’t a marathon—it’s a slow jog where you stop to tie your shoes every once in a while. 

As with any sex act, things can sometimes go awry. And, as with any sex act, there are risks to consider. Micro-tears and fissures are not uncommon and caused by friction, but can usually be avoided with lube and patience. If light bleeding does occur because of fissures or light tearing, take a few days to let your body heal.

If the bleeding doesn’t stop or is excessive, it’s time to seek out a doctor. Rarely, that can be a sign of more serious issues, such as a tear in the colon from sex or rectal prolapse (where the lower part of the intestine can drop due to nerve damage from anal sex). If something doesn’t feel right, it’s better to make an embarrassing trip to the doctor than deal with an unaddressed anal issue (and still have to make the trip to the doctor once you’re facing more intense medical problems).

I want to re-emphasize: serious health affects from anal are super rare and most can be avoided simply by listening to your body, going slow, using lube, and not pushing through any pain.  

What to Do After Anal Sex

Don’t skip out on aftercare.

Your butt just went through a lot! A lot of really wonderful sensations! But now it’s time to give your ass the rest it deserves. Anal sex can be incredibly intimate—give your brain and body a moment to enjoy the afterglow. Drink some water and take a breather. Once you’ve rested a little, clean your space: Put away your towels, wash any toys that were used, and wash your hands. 

It’s normal for a booty to be tender after anal sex. An Epsom salt bath can help your muscles and body relax. Backdoor Balm can help reduce inflammation and tender skin.

The most important part of anal sex is communication, and this is vital after the act as well. Check in with your partner about how they felt about the experience. If you enjoyed it, let them know! Laugh about any awkward moments. 

Anal sex is a great way to connect with another person and yourself. It’s also a rad way to explore a new part of your body and a great excuse to try new toys. There are so many ways to enjoy anal—lube up and get going.

Follow Archie Bongiovanni on Twitter.