Best Way To Introduce Anal Sex

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Let’s be real. Even for those of us who have a generally open-minded, been-there-done-that attitude about sex, the thought of anal sex can still seem a little scary if you’ve gone there. For one reason or another, anal is usually the final frontier sexually — and there can be a whole lot of buildup.
But our greatest fears often lie in anticipation, and once you give anal a go, you might just find that you’ve been missing out on something that can actually be really hot and satisfying. We checked in with some experts and asked them to take the mystery out of anal sex, and they schooled us on some positions that can help ease you into your first time to actually make it an enjoyable experience.
Arm yourself with these tips and a lot of lube, and you’re on your way to one kick-ass time.
In the traditional cowgirl position, your partner lies down while you mount on top — yeehaw! As the partner on top, you can ease into anal penetration by moving up or down as needed. Pro tip: Make sure your bottom partner does not begin to thrust until you’re good and ready.
Certified Master Sex Expert and Educator, Sex Coach and “So Tight” Sensual Fitness Personal Trainer Nikki Ransom endorses the cowgirl position for anal newbies. She explains, “This position will allow you to control the pace and depth that his penis goes inside of you. Remember to go at an easy pace and stay relaxed. It helps to have had an orgasm already and be highly aroused.”
Jessica O’Reilly (a.k.a. Dr. Jess, Ph.D.), author, international speaker and PlayboyTV’s sexologist, offers an alternative to the cowgirl in her book The New Sex Bible, “If she doesn’t like the sensation of deep penetration, but he desires more stimulation against the base of his shaft, she can reach backwards with a warm, wet hand to grasp the lower half of his shaft. Her hand becomes an extension of her butt while providing a physical buffer to ensure only shallow penetration.”
This position is most often associated with anal because it has major advantages. As the partner on the bottom, you can stay loose as you control penetration to increase pleasure. Getting busy on all fours may be your best bet if you have attempted and found anal painful in the past.
Patricia Johnson and Mark Michaels, co-authors of Designer Relationships, Partners in Passion, Great Sex Made Simple, Tantra for Erotic Empowerment and The Essence of Tantric Sexuality, recommend doggy style for first-timers and those who may have had an unpleasant experience before. The couple says, “Anal sex should never be painful. Always use plenty of lube and proceed slowly and gently.” Ransom adds, “Rub and stimulate your clitoris too to make it even more pleasurable.”
In The New Sex Bible, Dr. Jess has a different take on doggy-style anal sex. She recommends the modified doggy to give the receptive partner more control, support intimacy and provide the opportunity for double penetration. Dr. Jess explains, “She assumes a kneeling position with her butt cheeks on her heels and her knees spread wide open. She places her hands on her knees or the bed for support. He assumes the same position behind her and adjusts his height so that the head of his [penis] rests below her bum. He remains static as she lowers herself onto his head and takes a few deep breaths before sliding farther down his shaft. She drives her butt and hips up and down at her own pace as he reaches around to fondle her breasts or rub her clitoris.”
This position is preferred if you are looking for extra intimacy during the act. Start with your partner sitting as you mount his lap, face-to-face. Once again — as the partner on top, you can control depth of penetration to stay comfy. Face-to-face anal has the added bonus of extra stimulation for a woman: breasts, clitoris, go crazy!
Johnson and Michaels love face-to-face anal for the toe-tingling intimacy it provides. They confirm, “This position facilitates using eye contact and breath to build even more arousal.”
Dr. Jess agrees. She says, “I like this position as it allows the ‘mounter’ to exercise a good amount of control of the depth and rhythm of penetration. Wear a vibrating c*** ring for this one to provide extra pleasurable sensations as the top partner grinds against his shaft.”
A version of this post was originally published January 2015. 
Still want to change things up in bed? Our sex position bucket list has all sorts of moves to try: 
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How to Prepare for Anal Sex, According to Actual Doctors
Let’s talk about butt sex, shall we?
Whether you’re new to anal play or a total expert, knowing how to prepare for anal sex is the key to a pleasurable time. Okay, not just pleasurable. Preparation is just as important for safety as it is for comfort. Don’t worry, though—as long as you take the proper precautions and time to prepare, anal sex is generally safe. And luckily for you, that preparation is exactly what we’re covering in this article. So let’s get on with it!
Below, learn how to prepare for anal sex, as well as everything else you need to know about making anal sex safe, comfortable, and enjoyable, from prep to cleanup.
This is where the real preparation happens. Consider this everything you need to do before heading to the bedroom (or wherever you’re getting your anal play on).
1. Decide what kind of anal play you’re interested in.
Because spoiler alert: You have options! Sure, anal sex typically refers to penetrative sex—meaning, something going into your anus—and penetrative sex typically requires the most preparation. But anal is a wide umbrella, and knowing ahead of time what you’re interested in can help you prep however you need to. So the types of anal sex to be aware of include:
Penis in anus: Pretty self-explanatory—P-in-A sex is what many people think of first when you talk about anal sex.
Toy in anus: You have a lot of variety when it comes to anal sex toys. There are anal dildos that can be used for penetration much like a penis, sure, but your options don’t end there. There are also plugs, which are smaller and designed to be left in place. With anal beads, the pleasure is in the removal as much as the insertion. Prostate toys are uniquely shaped devices designed to massage the prostate—kind of like the anal toy equivalent of a G-spot vibrator or dildo.
Digital penetration: Exploring anal play with your fingers is excellent, especially for beginners who might be worried about size. Also, it’s also worth noting that if you’re going to explore penetration with a penis or a toy, a little bit of digital penetration will likely be involved as you “work up” to it. So you should always make sure your hand hygiene and nails are on point—and by that I mean clean, filed smooth with no rough edges, and fairly short (unless you really know what you’re doing).
Oral: Also known as anilingus...or rimming, tossing salad, or your other favorite oral-anal euphemism. If you’re not already a fan, oral sex on the same place poop comes out might make you squeamish, but you have nothing to worry about. If the receiver has had normal, regular bowel movements, anilingus is generally hygienic. But more on the poop of it all later.
Listen, we recommend lube in most sexual experiences anyway, but using lube is an absolute must during penetrative anal play, Joseph Frankhouse, M.D., medical director of colorectal surgery at Legacy Health in Oregon, tells SELF. That’s because while the vagina produces natural lubrication, the anus doesn’t. Anal penetration without adequate lubrication can cause the tissue in your anus to tear.
Not only is that painful, it also makes you more susceptible to sexually transmitted infections, like gonorrhea and HIV, board-certified ob-gyn Jacques Moritz, M.D., tells SELF. That’s because these tears create openings in the skin, potentially allowing infection-causing pathogens to enter.
When it comes to lube, you pretty much have three options: oil-based, silicone-based, and water-based. Oil- and silicone-based lubes are thicker and longer lasting, making them great for anal play. But oil-based lubes (like coconut oil) can break down condoms and render them less effective, so if you’re using a condom, steer clear of that kind of lube.
If you’re bringing silicone anal toys into the mix, you’ll want to avoid silicone-based lubes, since this kind of lube erodes silicone toys. But don’t worry—if you want to use silicone-based lube and toys, there are other toy materials out there that work just fine, such as glass or metal.
With all that in mind, if you’re engaging in anal play, using condoms, or using silicone toys, you’ll typically want to stick with water-based lube. Water-based lube is perfectly serviceable too—you might just find yourself having to reapply more often.
JO H2O Anal Water Based Personal Natural Lubricant, $19, amazon.com
Überlube Luxury Lubricant, $28, amazon.com
Shibari Personal Lubricant, $8, amazon.com
3. Make sure your toys are safe for anal.
Repeat after me: Not all toys are anal-safe! When it comes to toys for anal play, the most important rule is to make sure it has a flared base so it doesn’t get lost inside you. Because yes, you can get a toy stuck in your butt and it’s a thing people actually go to the emergency room for more often than you’d think.
Other than that, sex educator Jill McDevitt, Ph.D., recommends toys made of an easy-to-clean material like silicone, since it’s nonporous and hypoallergenic. For beginners, it can help to use toys that come in incremental sizes so you can “start small and then use larger ones as you wish,” says Dr. McDevitt. If you’re a beginner and want to go for a glass or metal toy, maybe err on the smaller side—these materials can be heavy, so you’ll likely feel full even without extra size.
Tantus Ultra-Premium Silicone Anal Butt Plug, $24, amazon.com
Real Vibes Anal Trainer Kit, $14, amazon.com
b-Vibe Petite Remote Control Rechargeable Blue Vibrating Rimming Butt Plug, $145, lovehoney.com
At least, under most circumstances. Unless you and your partner(s) are sexually monogamous and have all been tested recently, you should use condoms (or dental dams for oral) during anal sex to reduce the risk of sexually transmitted infections and HIV, Natasha Chinn, M.D., a New Jersey-based ob-gyn, tells SELF. Yup, you can get STIs via your butt.
Even if you are in a fluid-bonded relationship, using condoms is especially important if you’re switching from anal to vaginal penetration. Otherwise, you risk moving bacteria from your anus to your vagina or urethra. Your anus is home to all kinds of bacteria your vagina and related parts aren’t used to—namely, gastrointestinal (GI) bacteria, like E. coli. When this bacteria reaches your vagina, it can cause vaginal infections, like bacterial vaginosis, which can lead to vaginal itching, burning during urination, a “fishy” vaginal odor, and gray, white, or green vaginal discharge, according to the Mayo Clinic. It can also spread to your urethra, where it can cause a urinary tract infection (UTI). According to the Mayo Clinic, this can cause symptoms like constantly needing to pee, then a burning sensation when you do, along with cloudy urine and pelvic pain.
Long story short? If you insert anything into your anus, clean it off and/or roll on a new condom before putting it into your vagina.
Worth noting: Even if you and your partner aren’t worried about STIs or planning to switch between anal and vaginal penetration, using a condom may make you feel more comfortable if mess is a concern. Speaking of…
5. Be aware of how your poop might impact anal sex.
Whenever we talk about anal sex, questions about poop inevitably pop up, so it can be helpful to know going in what you can expect. So first, let’s walk through what actually happens inside your body when you poop. Food starts in your stomach, where it gets broken down. Then it passes through your small intestine, where it gets digested even more. The remaining food waste—that’s poop—gets stored in your large intestine, which is a long tube also known as the colon, according to the National Institute of Diabetes and Digestive and Kidney Diseases.
When there’s a bunch of waste in your colon that needs to come out, your colon contracts and pushes the stool into the rectum, an eight-inch chamber that connects the colon to the anus. Your brain receives the signal that you need to head to the bathroom sometime soon, and your rectum stores the stool until you voluntarily contract it to push the poop out.
In anal play, once you get past your anus itself, anal sex takes place in your rectum, which isn’t a storage area for poop unless a bowel movement is imminent. That means the odds of you actually pooping on your partner mid-act are very, very low, Dr. Moritz says. If you’ve recently pooped and you don’t have any health issues that make pooping a bit less predictable, like ulcerative colitis, a ton of feces probably won’t sneak up on you mid-anal.
Unfortunately, there’s a bit of a catch here, which is important for expectation-setting. When you poop, your body should expel all the stool in your rectum, but some fecal matter might get left behind. While you probably don’t have to worry about pooping on your partner, you should know that they may be exposed to some visible or invisible fecal matter, Dr. Chinn says.
That said, no one needs to panic. It’s as simple as washing it off with soap and water (or changing the condom), washing your hands, and continuing on with your life, whether or not that means getting back to anal sex. But it’s definitely something that all parties should be aware of before you start.
One last thing worth noting: The are a few more precautions and things to keep in mind about anal sex if you or your partner has a GI issue. For more information, you can check out this article on the topic.
Don’t get us wrong: Getting your bum ready for anal sex can be as simple as cleaning the area with water and a gentle washcloth so it’s as pristine as possible before you dive in. But some people prefer to take the extra step of doing an enema, and that’s cool too.
An enema involves pumping water or saline into the rectum to dissolve any stool that’s hanging out in there, making it easier to poop out. Since it’s pretty convenient to just grab an enema kit at your local drugstore or online, some people suggest doing this before anal to avoid any feces’ making an appearance in the bedroom. Fleet enemas ($8, Amazon) are a popular option (and incidentally, a big reason why so many people were laughing about Twitter’s new Fleet feature).
Again, you don’t necessarily need an enema. As we just established, the chances of you pooping on your partner mid-act are slim to none. But there’s usually no harm in doing an enema as long as you’re not doing it often enough to irritate your rectum, Dr. Frankhouse says. He recommends only doing them once every few months and following the instructions every time. If your butt starts feeling irritated when you do an enema, that’s a sign you should quit. Other than that, you can concentrate on external anal hygiene.
7. Try some anal masturbation first.
Whether you’re a total beginner to anal sex or an anal pro, it’s not just something you can jump into. But if you’re completely new to anal and planning on doing it with a partner, it could be worth it to do some solo exploring first. This can mean taking some time to work anal into your next masturbation session, whether by stimulating yourself with your fingers or sex toys.
This step is totally optional, of course, but it’s a good rule to keep in mind. “I always recommend people try most things on their own first before a partner,” says sex educator Dr. McDevitt. “It helps you gain comfort and confidence, learn what you like, want, and don’t like and don’t want.”
A big part of preparing for anal sex actually happens during sex itself. Beyond that, it might be helpful to brush up on these tips ahead of time so you know how to have the best experience possible.
If you’re exploring anal with a partner, you’ll definitely want to reserve some time for foreplay before anal the same way you would for any other kind of penetration. That’s to give your body time to relax. Your rectum is designed to keep poop in with help from a muscle called the anal sphincter. This can make anal penetration a little challenging at first, Dr. Moritz says.
You can start by asking your partner to give you a massage or do something else you know will loosen you up. “It takes a bit of time to relax [the anal sphincter],” Dr. Frankhouse says.
Then, when you feel cool, relaxed, and ready to start exploring anal play, you or your partner can use a finger or sex toy to massage the outside of your anus. This can help you get familiar with the sensation before any kind of penetration happens. Once you’re beginning to enjoy yourself, Dr. Chinn says you can experiment with sticking a finger or sex toy in your anus bit by bit based on what feels good, using plenty of lube, of course.
All of that said, Dr. McDevitt points out that when we talk about “working up” to anal, we’re only talking about taking the proper steps to ensure you’re ready for penetration if you want it—it doesn’t mean anal penetration has to be the end goal. “Anal play doesn’t have to mean anal penetration,” she says. “Certainly it can include that, but you don’t have to ‘work up to’ that if you don’t want to.” Instead you can stimulate circles around the anal opening with a finger, tongue, or pointed vibrator.
Numbing creams that use anesthetics like benzocaine are widely available. That doesn’t mean you should use them for anal, says Dr. Chinn. Your nerve endings are sensitive for a reason. They alert your brain to pain so you can prevent yourself from getting seriously injured, Dr. Chinn says. While numbing creams might make anal penetration feel easier, they don’t make it any easier physically. By numbing your anus, you or your partner could be pushing your body past its point of comfort without even realizing it.
Instead, just take things slowly and communicate with your partner. Anal play can be a lot of fun, and you shouldn’t have to numb yourself to enjoy it.
10. Try beginner-friendly positions.
Though there’s no one-size-fits-all guide to anal sex positions, Dr. Chinn says being on top might make first-time anal sex a little easier. That allows more control over how deep the penetration goes and how slowly it happens. As a bonus, there’s also the chance to add some clitoral stimulation, if that’s your thing.
If you’re more experienced with anal, you can have your partner penetrate you from behind through dogg
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