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Prepare to Have the Best Anal Sex of Your Life

Thinking of Doing It Backdoor? Memorize These Tips First

June 1, 2025

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There’s a lot that goes into having anal sex (see what we did there?).

If your partner has never done it before, for example, you’ll want to do everything in your power to make it a positive experience, so that the two of you can work back door into your repertoire.

And that means doing your homework to make sure you’ve done the necessary prep work, and knowing all of the best practices when it comes to putting it in another person’s butt.

It’s also worth taking a look at what you’re using as far as lube, anal toys and techniques, in order to make sure it all goes smoothly and that you’re going in fully prepared.

Also, not surprisingly, there are a ton of things that you should most definitely avoid doing during anal sex. And then there are those commonly believed butt sex myths, which could be putting an unnecessary damper on your butt play.

To help men everywhere have better, more frequent butt sex, this is a comprehensive guide that outlines it all. From the dos and don’ts, to the techniques that work, and even how to bring it up with your partner beforehand (yes, you have to) it’s all laid out here, to make anal easier to navigate than ever before.

So here’s everything you need to know about having the best butt sex ever.

Talk About It First

If you want to be granted access to the other hole, there needs to be a conversation had prior to entry. Whether your partner has done the deed before or this is a first for your partner, anal is one of those things that both parties need to get on the same page about in advance.

The “wrong hole” move doesn’t work, and if anything, pulling that routine is going to make your partner even more closed off to the idea.

“For a lot of people, this is still a third rail that they don’t want to touch,” says relationship expert April Masini. “Have a conversation about it ahead of time, and not in the bedroom, or in bed, or undressed,” she says. “You don’t have to plan it with an alert on your iCal, but if you both know it’s on the agenda, and you’re both fine to try it, when it does come up during sex you’ll be more ready than if you don’t have the conversation first.”

“Say that you read this article on AskMen today, and ask your partner if they would be interested in trying anal play,” says sex expert Vanessa Marin. “Don’t make it a big deal — because it isn’t! Ass sex is far more common these days than most people realize.”

If Your Partner Has Had a Bad Experience

In straight relationships, anal sex has a much different vibe than it does in queer ones. If your partner is a cis woman, she may be against anal not from prejudice — but from experience. There are lots of women out there who have tried it backdoor once, and then refuse to do it again.

This is because, if the prep work for her first time was nonexistent, the experience was likely a very painful and unpleasant one. But it doesn’t have to be, and making the point to her that you’re going to do everything possible to make backdoor pleasurable rather than painful will help grant you access.

The anus is actually packed with nerves; it’s just a matter of stimulating them the right way. Proving this to her by using your fingers first is an effective way to get her interested in anal.

“Gently rub on the outside of the anus, and be guided by your partner on how much pressure to apply,” says sexologist Bianca Laureano. “Use your knuckles, as they add a different sensation when rubbed against the anus and perineum (the space between vaginal opening and anus). Fist your hand and rub the knuckles gently against her anus. Go in circular motions. If there’s too much lube or spit, blow for an added sensation onto your partner’s anus.”

Anal Sex Prep 101

Preparation is key to successfully executing anal. Here are a few steps to take before you attempt backdoor entry.

What Not to Eat Beforehand

Talking to your partner about their diet beforehand may be a bit of a mood killer, but you’ll both be happy that you took this precaution later on. Tell your partner to avoid anything that would come out the other end as, uhh, sharp. For example, nuts and seeds.

Carol Queen, staff sexologist at Good Vibrations and the author of The Sex & Pleasure Book: Good Vibrations Guide to Great Sex for Everyone also recommends staying away from things that might negatively impact bowels.

“For comfort’s sake, nothing too, too spicy, either,” she says. “For the sake of cleanliness, things that might encourage a bowel movement — coffee, or really any hot beverage — should be avoided too.”

How to Clean Out

One of the most common worries women have when it comes to backdoor sex is the amount of mess it could potentially leave. But if your partner is able to encourage a bowel movement prior to the act, you’ll both have less mess to deal with.

“If she’s had a bowel movement already on the day you have your first anal adventure, there will likely be very little fecal matter to encounter,” says Queen.

To take it a step further, use a bulb syringe or do anal rinse using an enema bag.

“Whether or not you do this step, consider putting an absorbent pad or towel down; these are easy to throw in the trash or washer and then you can cuddle on the sheets with no fear,” says Queen.

Use Protection

What’s worse than a sexually transmitted infection? An STI that takes up residence in your butthole. Usually when we think about STIs, we’re worried about them in the context of P to V contact, or oral. But according to Masini, contracting an STI from butt sex is completely in the realm of possibility.

“If you’re dating and this type of sex comes up as ‘a thing’ that one or both of you want, chances are that one or both of you have done this before,” she says. “That exposes you to health risks, so use a condom.”

Set the Mood

The key to a good anal experience is a relaxed anus, so take whatever steps are necessary to put your partner at ease and get them in the mood.

RELATED: How to Get Her in the Mood

“Muscle tension is not your friend with ass play, because it can add discomfort or pain if you don’t get past it and relax. Get her in a position for sex where you can both be as relaxed as possible,” says Queen.

If you don’t already know what it is that turns your partner on, now would be a good time to find out, and then pull out those stops. Whether it’s a bubble bath or a certain kind of porn or you dressed up in some costume, do what you need to do in order to get your partner ready to go.

Give Them an Orgasm Beforehand

A tense body makes for tough times when it comes to butt sex. Certified sex educator Anne Hodder suggests loosening things up by getting your partner off in advance.

“I like to tell clients to have at least one orgasm before having anal sex,” she says. “Anal sex can be nerve-wracking and some of us have anxiety about our first times. With anxiety often comes tense muscles — and a tense anus! The more relaxed you can get the muscles around the anus and genitals, the more comfortable it will be to ease something inside.”

RELATED: How to Make a Woman Orgasm

While you’re getting her done, keep in mind that most women take much longer to orgasm than men do — we’re talking 20 minutes at least here. So be patient, and make sure she gets off before you try entering the back door.

Give Them a Rim Job

“Rimming, where your partner licks the area around your anus, can help relax the area and increase stimulation,” says Hodder.

Of course, if the idea of doing this grosses you out, you might want to reconsider sticking your dick into someone’s butthole.

But in all seriousness, Hall suggests showering as part of your butt sex prep, which will likely help your rim job execution, as well as your attempt at anal.

“Take a warm shower to relax your body, and clean carefully in preparation,” she says.

For further relaxation benefits, incorporate scents that are proven to reduce stress, like lavender, into your pre-anal shower. There’s no shame in enjoying some loofah action pre-butt sex — especially when it’ll make entry even easier for both of you.

How to Have Anal Sex

You’ve done all the prep work, set the mood, and now your partner is all hot and bothered and ready for entry. Here are a few steps to follow for some successful butt sex.

Start Slow

Don’t just dive in there, dick blazing.”It might be good to play down there first and get the person used to the sensation,” says sexologist Dr. Nikki Goldstein, “to help them unlock the brain pathways from seeing this just as something used to go to the bathroom to a place that can also cause pleasure.”

“Try to warm your finger up under your body before playing with her. Kiss her from head to toe, play with her nipples with your fingers or tongue, then her vagina and then her anus using a little lube on your fingers,” says Nick Hawk, star of Showtime’s reality show Gigolos.

Lube It Up

Lubrication is an absolute necessity when it comes to anal sex.

“Use lots of lubrication,” says licensed psychologist and certified sex therapist Dr. Rachel Needle. “Unlike the vagina, the anus does not produce its own lubricant. The more lube you use, the more comfortable and enjoyable anal sex can be,” she says.

In addition to rubbing a good amount of lube all over your penis, from the tip to the base, you may also want to squirt some lube into your partner’s anus to make extra sure there’s lube all the way inside for any deep penetration. There are even products for doing just that called lube applicators.

Antonia Hall, author of The Ultimate Guide to a Multi-Orgasmic Life, also notes that it’s important to pay attention to the type of lube you’re using as well: rather than water-based lube, choose a silicone-based one.

These don’t go well with silicone-based toys (the lube is likely to degrade the toy’s material), but for penis-in-anus penetration, silicone-based lube is your best bet: It lasts much longer than water-based lube, which is important since you don’t want the lube drying up mid-coitus.

Ease Your Way In

It may be best not to insert your penis all the way the first time as well.

“If you hurt her, she will not want to do it again,” says Hawk. “It’s even better to let her stick it in and back into it from doggy-style or even ride you and take total control. Tell her you like it when she plays with herself if she’s not completely enjoying the experience or is unsure about it.”

Communicate

Laurie Handlers, a sex and happiness coach, recommends staying in constant communication.

“‘May I touch you here? May I enter you only at the opening now?’ Asking, ‘How is the pressure? More/less/the same? May I go further in now? And now how is the pressure? More/less/the same?’” says Handlers.

Sexual consent here is extremely important. Nobody wants stuff done to their butt without their consent, period.

Agreeing on a safe word between the two of you is a good idea, too.

“For instance ‘Red!’ means ‘Stop now!’ Agree on this ahead of time,” she says. “Make sure you both understand that if the receiver says ‘Red!,’ the giver slowly and immediately stops and removes him/herself.”

Anal sex can be intense, and the person being penetrated must be in charge so they can communicate their needs to their partner, says Queen. Saying “Slow down,” “Take it easy,” or “Stop for a minute” doesn’t spoil the fun — it allows play to go on longer by keeping things comfortable.

Be Prepared to Stop and Start Over

“As with any new type of sexual experience, things don’t always go as planned,” Masini says. “Just because it doesn’t work, or one person wants to stop, doesn’t mean it won’t go well the next time you give it a try.”

“Every sex act has its timeline in your life and it’s important to be patient, open-minded, creative and flexible about how, when and if this is something you really want to do,” she explains.

Anal Sex Don’ts

Successful anal sex is all about experimentation, trial and error. But there are a few things you should never be doing when it comes to entering the backdoor. Here are a few things to avoid during anal.

Never Go From the Anus to the Vagina

Forget everything you learned from porn. If your partner has a vagina, it’s not interchangeable with their butthole.

“The anus has bacteria that can infect the vagina,” says Handlers. “So it’s never a good idea to go from the anus to the vagina without first washing with soap and water — whether toy, finger or penis. And when using a lot of lube, it’s possible that the lube can drip from the anus to vagina if a woman is facing down with rear entry,” she says.

So, it’s important to be careful.

Don’t Go in Hard and Fast

“Take your time with penetration,” Marin says. “You’ll want to go much more slowly than you do with vaginal penetration.”

Sex therapist Dr. Kat Van Kirk also recommended starting with just the tip of the penis and gradually going in as deep as your partner allows.

Don’t Pull Out Too Fast

If your partner’s feeling pain from the anal penetration, you might feel horrible and guilty and want to end it as fast as possible. But in that situation, pulling your penis out as fast as possible is actually not the right approach.

Pulling out of someone’s butt too quickly can result in serious injury to the anus — and a trip to the emergency room is probably not how you want to remember this experience. Whatever your partner’s experience, when it’s time to pull out, do so slowly and gently.

Don’t Keep Doing It If They’re in Pain

While discomfort during anal sex is common, if your partner is in excruciating pain, you’re doing something wrong, and it’s time to slow down and reevaluate.

According to Queen, common causes of anal sex pain include not being relaxed enough, the top going in too hard and fast, or not using enough lube.

Anal Sex Myths

Alright, so now you know the stuff you should absolutely believe about ass sex. Now, for a few commonly believed anal sex myths that are completely untrue.

You Should Have Anal Sex From Behind

Positioning is important in any sex act. But for anal, sex writer John Romaniello says, it’s especially integral.

“If you watch a lot of porn, you may think that ‘doggy style’ is and should be the default position for anal,” he says, “If you read certain magazines, you might think that a spoon position is the way to go. Neither of these are correct. Both of these positions make things somewhat more difficult physically, but more importantly, can also lead to an emotional disconnect.”

So what position is best for butt sex?

“If your partner is inexperienced with anal, the only correct position is missionary,” Romaniello says. “Not only will it allow for easier entry, but the important thing is that it allows you to see their face. This obviously increases the feel of intimacy — and when your partner is trying something new, that’s hugely important.”

Not only is being able to see your partner important for building an emotional connection, but Romaniello says it’s also extremely necessary to be able to gauge how things are going from their facial expressions.

“A lot of people on the receiving end just assume anal sex is supposed to hurt, and just ‘fight through it’,” he says. “As the giver, it’s your responsibility to make sure this doesn’t happen. Sure, there may be some discomfort, but it should never hurt. When you’re having sex with someone from behind or in a spoon position, you can’t see their face and have much less of a read on them. If they’re in pain, you won’t necessarily know.”

Of course, in a perfect world your partner would speak up and just say she’s in pain. But statistically, that’s not the case. Particularly if this is your first go at anal, Romaniello stresses the importance of having visibility into your partner’s reactions.

“You have to be face to face so you can accurately assess the situation,” he says, “and know when to slow down or stop. Any time they make a face that implies anything other than pleasure, stop moving. Just wait. Don’t even breathe. Allow them to adjust and accommodate, and then proceed when they are ready.”

Anal Bleeding Is a Sign of a Serious Injury

The sight of blood is usually alarming. Seeing blood coming out of your butthole? Downright terrifying. But according to sex therapist Lisa B. Hochberger, the small tears to the anus that may occur as a result of anal aren’t the sign of anything serious.

“Blood from the anus can be caused by a few different things,” she says. Hemorrhoids — that is, swollen veins in the anal area — “make a person susceptible to bleeding, and it’s not uncommon to see blood in bowel movements or on toilet paper as a result of a hemorrhoid [after anal sex],” she says. “An anal fissure, or slight tear to the lining of the anus, may occur at the opening of the anus [after anal sex]. These tears take a while to heal because they are often irritated as a result of bowel movements,” she explains.

By now you’re probably wondering: Are there any serious injuries that can happen as a result of anal? In very rare cases, Hochberger says that a perforation in your colon could occur as a result.

“If you’re in severe pain, feel pressure in your abdomen or have a fever, it is possible that you have a perforation in your colon,” she says. “This is an extremely rare complication of anal sex. If you think you may be experiencing this rare condition, it is recommended that you see a medical care provider immediately to receive further medical attention.”

Alcohol Makes Anal Sex Easier

Sure, lots of sex has been helped along thanks to alcohol. And while there are negative implications that come with drinking too much and then trying to have good old fashioned P in the V sex, having your anal sex game plan include your partner getting a little tipsy to help themself relax is not a good idea. In fact, it could end up causing serious injury.

RELATED: How to Deal With Painful Sex

"Alcohol can act as a vasoconstrictor, and the rectum is full of capillaries,” Romaniello explains. “Getting your partner drunk is likely to make them tighter, which is not going to help. Additionally, you do not want your partner to be numb. If she’s drunk, she may not realize that you’re hurting her.”

Pain is an indicator to the body that something isn’t right, and if your partner can’t feel it, Romaniello says you’re risking serious damage that won’t be evident until the next morning. Not to mention, if there are injuries sustained from your first anal attempt, your partner is likely going to be pretty reluctant to try anal again.

“Rather than get them drunk, just allow them to relax naturally,” Romaniello encourages.

Best Products for Anal Sex

The incredible thing about anal sex is that, just when you think you've mastered this art form, a new toy or product hits the market that takes the whole experience to the next level.

Whether it's a new formula of anal lube engineered to create just the right amount of friction and slippage, or a butt plug that lets you operate it remotely, there's always a fresh take on an old classic being released at your local sex shop or favorite online store that's worthy of putting in your partner’s butthole (or your own) (or both).

Looking to place a sure bet on your next anal sex toy purchase? Look no further. These are our top recommendations for the latest products to take your anal play to a place it's never been before.

b-Vibe Anal Trainer Kit

Never tried backdoor pleasure before? You might want to invest in a kit for anal beginners before you go buck-wild with the bigger, more intense toys. As with many things in life, it behooves would be anal-izers to start small and build from there. This kit from b-Vibe includes three sizes of plugs, so you can go from one to the next once you’ve adapted, plus a manual with lots of handy anal info and a lube shooter to help ensure that all the hard-to-reach areas get their fair share of lubrication.
$95.99 at bVibe.com

Fun Factory Bootie Fem

If your partner’s a vagina-haver, do them a solid and get Fun Factor’s Bootie Fem. It’s a butt plug explicitly designed for people with vulvas; lots of anal toys are either designed for prostate-havers or anatomically neutral. It’s small and so cute and provides a great starting point for couples looking to explore anal without breaking the bank or going all-in on complex toys and gadgets.
$43.66 at FunFactory.com

Pjur Back Door Relaxing Silicone Lubricant

There’s no getting around it — anal sex has different lube requirements than vaginal sex. Whether you’re using condoms with your partner(s) or not, hitting it backdoor-style means you need a lot of lube, since, well, the butt can’t lubricating itself like a vagina does. The best approach for penis-in-anus sex is a silicone-based lube that’s specially formulated for anal — like this stellar options from Pjur, which is long-lasting and contains muscle-relaxing jojoba oil. (Though for most toy play, you should stick with a water-based lube, since silicone-based toys will degrade when paired with silicone-based lube.)
$34.99 at Amazon.com

LELO Hugo 2

Want to explore the rocking pleasure potential of prostate orgasms? Congrats! LELO’s Hugo 2 is a multi-year winner of our Dating Awards category for Best Prostate Toy for a reason. It’s incredibly well designed, powerful and intuitive. Plus, its remote control Bluetooth functionality means you can hand over all the power to a partner and let them drive you wild with anal vibrations.
$160 at Lelo.com

Fifty Shades of Grey Silicone Anal Beads

If you've mastered the fundamentals of anal, sex and relationship expert Dr. Kat Van Kirk recommends giving anal beads a try. “You will learn that you have more latitude in regards to movement and angle," she says. "Depth and force will vary greatly.” The beads on this toy differ in size; the smaller ones are easy to insert, while the large ones further down will make the receiver feel satisfyingly full. Pro tip: Moving them in and out of the anus, or pulling them out at the moment of climax, will mean lots of pleasure for the receiver. Anal beads like these should always be paired with a water-based lube, or something else that’s not silicone-based.
$19.99 at Lovehoney.com

Njoy Pure Plug

While many anal toys are silicone-based, not all of them are. Pair your long-lasting silicone lube with a metal toy like Njoy’s stainless steel Pure butt plug and enjoy. Its looped handle makes for easy insertion and removal, and the weight of the material means it fills you up better than a same-sized toy made from silicone. The one thing to keep in mind is that you’ll likely need to do some warming up before insertion — unless you’re one of those who really enjoys feeling it go from cold to warm as it adjusts to your body heat.
From $98 at NjoyToys.com

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