Wanna Try Anal Sex? Here's How To Prepare

Everything from a vacation to a D&D campaign is better with thoughtful planning, and anal sex is no exception. Unfortunately, this popular fantasy is woefully misunderstood, leading far too many people to dive in unprepared, have a bad time, and be left thinking they don’t enjoy anal sex. When sex coaching clients tell me about their experience, there are some common trends: lack of communication, lack of preparation, lack of lubrication, and going way too fast. Luckily, these issues are easily addressed.

But first — why is anal sex so popular? When approached correctly, it can be very pleasurable. The anal area is full of sensitive nerve endings that can enjoy sensual touch. And with penetration, you can also stimulate the prostate (and even the G-spot!) Anal sex is also considered taboo by many, which can simultaneously add to the thrill and make accurate information more difficult to find.

Anal sex isn’t for everyone — and it’s totally fine if it’s not your cup of tea. Just because something is a popular fantasy doesn’t mean you must be into it. As a sex educator, I want to make sure people have complete and accurate information so they can make fully informed decisions. And if someone thinks they don’t like anal because the one time they tried it there was no warm-up and no lube, that’s unfortunate. So here’s everything you need to know to prepare for pleasurable anal sex.

Prepare Mentally And Emotionally For Anal Sex

Perhaps you’ve heard that the brain is the biggest sex organ. It might not sound very sexy, but there’s some truth to it. To enjoy any kind of sexual activity, you need to be mentally and emotionally prepared. And because pleasurable anal sex is dependent on relaxation, that’s doubly true. When receiving anal sex, the most common cause of pain is when the internal sphincter (just inside the external sphincter/anus) is still too tight, but something is pushed in anyway. And there’s no forcing that sphincter to relax — you just need to be genuinely ready.

The first step in being mentally prepared for anal sex is to make sure it’s something you really want to do. No matter how popular anal sex is in porn or how excited your partner might be to try it, anal sex isn’t for everyone. And it’s OK if you’re simply not interested.

To figure out if anal sex is something you’re interested in for your own sake (rather than to please someone else), it’s worth exploring the area on your own first. “Try exploring anal play solo and notice what comes up for you, both around tension and pleasure. Practice deep and calming breaths, which can help with mental and physical relaxation and make anal sex more comfortable,” says sex educator Amory Jane. The best way to start is with some external massage, with a single finger of a gloved hand, and plenty of lube. If that’s pleasurable, you can try inserting one finger, or starting with a small toy.

Exploration can also include reading books about anal sex or attending online classes. Jane suggests, “Talk to your sex-positive friends who may have already had anal sex, or listen to sex podcasts that feature episodes on this topic.” Here’s an anal sex podcast playlist to get you started:

• “Anal Pleasure,” Shameless Sex
• “Anal Breathing and Erotic Breathwork,” Shameless Sex
• “Anal Sex Extravaganza,” Girl Boner Radio
• “Butt Stuff For Everybody with Tristan Taormino,” American Sex Podcast
• “Speaking Of Sex — How To Have Anal Sex,” The Pleasure Mechanics
• “All Aboard The Booty Train,” Sex With Emily
• “All About Anal,” Sex With Dr. Jess

Prepare Your Body For Anal Sex

People tend to worry about hygiene when it comes to anal sex, but a simple shower is typically thorough enough. Unless you’ve recently had an upset stomach, fecal matter doesn’t hang out in the rectum. So an external cleaning is usually all that’s required. If you’d like to go a step further while in the shower, you can insert one finger up to the first knuckle and do a little swirl to make sure things are all clear. Right before it’s time to play, you can do one final clean-up with a body-safe wet wipe (like Afterglow) to set your mind at ease.

While some folks recommend an enema before anal sex (an injection of fluid to cleanse the bowel), I think enemas are best left to the pros. An enema can be hard on your system, causing cramping, and is likely to leave you feeling less than sexy. The enema nozzle can also damage delicate tissues, leaving you extra sensitive — which isn’t ideal for anal play.

Changes to your diet, like adding more fiber, can also help keep things clear and regular. “Some people choose to eat smaller meals on the day(s) they plan to have anal sex, and will make sure to have bowel movements earlier in the day so they feel empty and ready for action,” says Jane.

Prepare With Your Partner For Anal Sex

Anal sex should not be a spur-of-the-moment decision. Before any anal play takes place, it’s important to have conversations with your partner to make sure you’re both enthusiastic about trying it out and on the same page about how it’ll go.

It’s best to have these conversations “outside of a lusty bedroom moment, so as not to create a pressure to say yes,” says Jane. In other words, don’t negotiate naked. Once you’re undressed and turned on, it’s difficult to think clearly, and you’re likely to miss something important. And, as Jane says, there can be pressure in the moment to go along with what the other person wants.

Conversations about anal sex don’t all need to be serious or intense. Discussing fantasies can also be playful and sexy. “Try incorporating anal into your dirty talk or sexting, as a way to test the waters,” says Jane. Like exploring any fantasy in dirty talk, make sure you get consent first. And make it clear when this banter is meant simply as fantasy fodder for arousal, versus a promise of things to come. People are much more free and comfortable in their dirty talk and sexting when they know it isn’t meant as an indication of what they’re willing to do IRL.

When you are ready to negotiate potential anal sex, Jane says, “You'll just want to make sure to have conversations about STI status, what kind of protection will be used (gloves, dams, condoms?), turn-ons, soft and hard limits, and any relevant information about injuries, trauma, and anal experience level that may help you and your partner have an enjoyable time.”

Prepare Your Space For Anal Sex

Preparing your space for anal sex ahead of time will make it so much easier to stay in the moment once you get started. Nothing breaks the flow quite like having to go hunting through your drawers or closets to find lube or condoms when they’re needed. Even worse, sometimes people will skip using these items if they’re not found quickly (and may regret it later.)

To get ready for anal sex, here are some items you might want within easy reach:

• Lube
• Towels
• Wet wipes
• Safer sex supplies, including condoms, gloves, dental dams, and internal condoms
• Anal-safe sex toys, such as toys with a wide, flared base intended for anal use

In addition to the practical must-haves, it’s also worth making your space feel sensual and inviting. Put away the laundry, light a few candles, and turn on your favorite sexy playlist. “I tend to throw down a sex blanket or towel in advance and have all of the toys laid out, so when we get home from date night, the scene is set. I really like using a humidifier with a few drops of my favorite essential oils, so that the air has a comforting scent to help me both unwind and awaken more of my senses. I also suggest having mood lighting and a way to play music, and placing a mostly empty garbage can nearby, for easy wipe or barrier disposal,” says Jane.

Use Safer Sex Practices For Anal Sex

Safer sex is a vital part of preparing for any kind of sexual activity, and anal sex brings some specific considerations. For starters, it’s important to know about location-specific infections. This means there are some STIs you can get on your anus (or in your throat) that won’t show up during the standard STI tests that only sample blood and urine — such as chlamydia or gonorrhea. So if you’re engaging in anal sex, it’s a good idea to ask your doctor for a location-specific swab as part of your testing.

If anal sex is going to be a regular part of your sex life, you may also want to talk to your doctor about PrEP (pre-exposure prophylaxis,) a medication that can significantly reduce your chances of contracting HIV.

Don’t forget the lube! Not only does it make anal sex comfortable, but it also makes it safer. Without lube, the delicate tissues of the anus and rectum are more likely to tear, making it easier for bacteria to enter the bloodstream.

“Even if you are monogamous and you and your partner usually have unprotected sex, I would still suggest using a condom for anal,” says Jane. And that’s not just for safety. “Condoms can help prevent many STIs as well as help with glide and cleanup.”

If rimming (analingus) is going to be part of your anal play, consider using a dental dam. In addition to STIs, oral/anal contact can lead to the ingestion of bacteria that cause stomach upset and may even require a trip to the doctor for antibiotics.

With anal play, you must be careful of cross-contamination if there’s also vaginal play happening. “Using one condom for anal and a different one for vaginal sex is a must if one penis [or sex toy] is going between two holes. In general, it is best to avoid transporting butt bacteria into the mouth or vagina. This can lead to yeast infections and/or bacterial imbalances,” says Jane.

One sex educator hack for addressing this problem is to use internal condoms. For anal use, be sure to remove the internal ring, making it more comfortable (there’s less room for it to spread out in a rectum than in a vagina). But once you have an internal condom placed both in the anus and in the vagina, a penis can then move between anal and vaginal sex.

“One final pro tip: if/when someone with a penis is going to have an orgasm, please keep in mind that a warm rush of fluid into one's rectum may make your body think you're doing an enema. Some people love that sensation, but for anal sex beginners, this is another excellent reason to use condoms,” says Jane. Nothing kills the mood like a desperate urge to run to the bathroom.

Getting Started

Once you’ve laid all the groundwork for anal sex, it may be tempting to just dive in, but it’s important to maintain a slow and mindful pace. The first time you play, you may even want to stick to external massage. The whole anal area is very sensitive, and exploring touch with fingers, toys, and even tongues can be very pleasurable. Starting slow also helps your body relax and learn that anal stimulation is part of sexual pleasure, and that will help when you try more advanced play later.

When you're ready to explore penetration — you guessed it — going slowly is still key. “To begin the journey to anal sex, apply plenty of lube and start by inserting a finger. Make sure to go slowly and breathe. If you have never had anything in your butt before, start with just inserting one finger up to your knuckle and only going further/adding another finger once your body adjusts and is ready for more,” says Jane.

Sex toys are another great way to get started; just make sure you’re using body-safe toys that are intended for anal use. “Having some tapered and easy-to-insert butt plug options are key. Silicone plugs tend to be popular because they're flexible, non-porous, and easy to clean. Try small plugs/dilators for a while, and once those begin to feel easily comfortable, you may move up to larger plugs. If the plan is to eventually have anal sex with a penis, you can practice with a dildo that is slightly smaller or around the same size as your partner.”

Troubleshooting

Even if you follow all these tips and move slowly, you may still experience some discomfort while receiving anal sex. It’s important to stop and make adjustments at the first sign that something isn’t working. Pain is your body’s way of telling you something isn’t right — so don’t ignore it. “I recommend slowing down, tuning into your own or your partner's body, and figuring out what you need to feel comfortable. More lube? A different position? Less big in-and-out movements and more shallow circles? Zone in and then bring it up!” says Jane.

With a bit of preparation and know-how, plus a willingness to go slowly and listen to your body, anal sex can be a pleasurable addition to your sexual repertoire!

Expert:

Amory Jane, Sex Educator and Director of Communications at She Bop