Anal sex tips aren’t just about the right positioning or lubrication. If you’re considering having anal sex for the first time, you’re probably wondering how to do anal—how do you prepare, relax, and enjoy the intimate moment with your partner? And is anal sex safe?
These questions are becoming more common. According to research from the Kinsey Institute, more young women than ever—45%—are exploring anal play. So to answer your first-time anal sex questions, we called in the experts. And while they all shared different tips for first timers, their advice had one common thread: The key to enjoying anal sex is preparation—and consent.
“Sometimes you’re not in the mood for anal, and sometimes your butthole isn’t in the mood even if you are,” explains Luna Matatas, sex educator and the host of the anal sex podcast The Plug. “In addition to hygiene, prep, and communication, anal sex, like other kinds of sex, is hotter with more arousal in the whole body and erotic mind.”
That’s why it’s important to come prepared, and educating yourself is one of the best ways to do so. Anal sex can be overwhelming for those new to it, but luckily, there are many ways to familiarize yourself before trying it out IRL.
“Look up educational resources, research different toys, and consider the questions you may have for yourself and your partner,” suggests Kate Balestrieri, PsyD, certified sex therapist and the founder of Modern Intimacy. “Take your time to communicate your needs, fears, and hopes, and make a plan that is intentional.”
For a mantra to guide you through your first anal sex experience, Good Vibrations staff sexologist Carol Queen, PhD, suggests the following: “Relaxation, lubrication, communication.” The advice, below, is all essentially variations of that trio. Read on for more in-depth advice on how to prepare for anal sex and make your first time safe, comfortable, and pleasurable.
Note: Most of these tips are described from the perspective of someone with a vulva. They can be accomplished with a partner who has a penis, is wearing a strap-on, or is using a sex toy.
1. Relax your mind…and body.
The last thing you want to be before attempting anal penetration (or anal stimulation) is tense. “If you’re hesitant, nervous, or not into it, no one is going to get off, and what’s the point of that?” says Tristan Taormino, author of The Ultimate Guide to Anal Sex for Women.
If this is your first time trying anal sex, spend some time relaxing—take a hot bath, ask your partner to give you a sensual massage, heck, you can even meditate. To prepare for anal sex, you can also focus on specifically relaxing the muscles of your anal sphincter. To see what that feels like, tighten your butt muscles and then release.
2. Explore on your own.
Suzannah Weiss, resident sexologist for Biird and author of Subjectified: Becoming a Sexual Subject, recommends playing with yourself first to learn what you like and don’t like before including a partner in the mix. “The easiest way to begin would be with your finger,” she says. “First, warm yourself up with clitoral stimulation. Then put a water-based lube on your finger and start gently inserting it while combining it with the clitoral stimulation. That will make it more enjoyable.”
If you enjoyed that experience, she suggests moving up to a butt plug. Look for a set with multiple sizes so you can start small and work your way up as you gain confidence and experience.
“I would recommend doing those things before you attempt anal sex with a partner,” Weiss says. “You want to know that it is something you can enjoy and how you enjoy it, so you can communicate that to your partner. If it’s something you’re not enjoying on your own, it’s unlikely that you would enjoy it with a partner.”
3. Communicate openly.
Figuring out how to do anal sex with your partner starts with communication. “Talk about it first. As with all types of sexual activity, anal sex is something that should be discussed beforehand,” says Rachel Needle, PsyD, a licensed psychologist and certified sex therapist. “Communicate your fears and expectations with your partner, and make sure that you are both on the same page about things like speed, depth, etc. Trust me, this is one area in which you do not want any surprises.”
4. Establish boundaries.
Throughout the experience, it is your job to pay attention to what you are feeling, and communicate this to your partner. If something feels uncomfortable or painful, let them know. You may choose to establish a safeword to let your partner know you’re not comfortable moving forward or that you want to move a little slower.
5. Lather up.
“Many people’s fear of first-time anal sex stems from a fear of what goes on back there (naturally) and how that’s going to play into the action,” says Needle. “To cleanse yourself (literally) of such mental roadblocks, take a nice, steamy shower first.”
6. Engage in plenty of foreplay.
One of the best ways to ease into anal play is to make sure you’re extremely aroused beforehand. “The number one mistake people make is rushing,” says Taormino. Start with foreplay, vaginal sex, oral sex, or whatever turns you on. (Being one or two orgasms deep before you try any anal penetration helps.) “The more aroused you are, the more relaxed your sphincter muscle will be, and that’s going to make for a hotter and easier experience,” she says.
7. Use lube. A lot of it.
The key to really enjoying anal sex? Lube, lube, and more lube. 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, explains Needle. (It also helps prevent bleeding after sex.) If your partner is using a condom, don’t forget to make sure to apply a water or silicone-based lubricant (oil-based lubricants aren’t compatible with condoms). Weiss recommends sticking to a water-based lubricant if you’re using a silicone toy, as silicone lube can cause the material to degrade.
And don’t be afraid to reapply frequently. More lube equals better anal sex, always. “Use lots of lube and keep reapplying if it dries out,” Weiss says. “And make sure to stop if anything becomes uncomfortable—if anything tears, that could increase your chance of STIs.”
8. Assume the right position.
For first-time anal sex, the receiver (a.k.a. whichever partner is being penetrated) should be the one to control the depth and speed of penetration. However, certified sex educator Ellen Barnard doesn’t recommend the receiver being on top for first-time anal experiences because you would need to use your legs more in that position, tensing the pelvic floor and causing the anal sphincter to tighten.
For first-timer-friendly sex positions, Barnard has some other suggestions. “I recommend on one’s back at the edge of the bed, partner standing between one’s legs, and either holding behind your knees or putting your legs on your partner’s shoulders and moving into them,” Barnard says. “This allows the pelvic floor to be very relaxed and open. Spooning is also a great position and you can move back into the penis or dildo rather than them moving into you.”
9. Take it slow.
No matter how much lube you use, your backdoor is not a water slide. First-time anal sex should be approached like getting into a really hot bath tub. First, you test the waters during foreplay, allowing your partner to gently rub around the opening with their finger, before experimenting with actually inserting anything. Whether you’re using a penis, a finger, or a toy, start slowly with just the tip before inserting anything any deeper. Tantric sex can be good for slowing it down.
10. Try a toy
Using anal sex toys like a small dildo, butt plugs, or anal vibrators can be a great way to ease into things. The key here is to be gentle and communicate. If at any point things get too uncomfortable, speak up.
Barnard recommends getting a set of progressively sized anal plugs and wearing them during other sex play, whether vaginal, oral, or manual.
11. Don’t cross-pollinate.
Whether it’s a finger, a toy, or a penis, make sure to never go from butt to vagina—it’s a UTI waiting to happen. If you want to switch to vaginal stimulation after anal play, hop into the shower to keep the action going or keep a tub of baby wipes on your nightstand to sanitize in between.
12. Remember to breathe.
In those first few moments of penetration, the pressure tends to cause people to hold their breath. This results in the immediate tightening of those muscles, which will only lead to pain. Take deep, even breaths and focus on relaxing your entire body and release all tension. It may feel like you have to go to the bathroom at first, but just go with it.
13. Speak up about pain.
First-time anal play will be full of new sensations, some weird, some amazing. What you shouldn’t feel is pain. If at any point during the action penetration becomes painful, let your partner know immediately. You may want to add more lube, slow things down, or give it a rest for a while and switch to other types of stimulation.
Using props can also be a way to help with discomfort. Matatas recommends pillow props or sex wedge cushions, especially for anal missionary positions.
14. Use a condom.
Just because there’s almost no risk of getting pregnant doesn’t mean you can skip the condom if your partner has a penis. Condoms are the only way to prevent sexually transmitted infections. Just don’t go from anal to vaginal penetration with the same condom, as that can spread infections. Ditch the condom and put on a new one before penetrating the vagina.
15. Don’t forget clitoral stimulation.
There are many shared nerve endings between the walls of the vagina and the anus, so stimulating the vagina simultaneously can be pleasurable. If you feel comfortable, insert something (perhaps a finger or a vibrator) into your vagina while you are engaging in anal play.
However, if this is your first anal experience, consider focusing only on the clitoris. “Vaginal stimulation can actually increase pelvic floor tightness and make anal penetration much less comfortable,” Barnard says. “So I tell folks to focus on lots of warm-up and clitoral stimulation to help increase blood flow and arousal and make the pelvic floor muscles relax more easily.”
Queen says that, for most people with a vulva, “the clitoris is the primary driver of sexual arousal and, to boot, is much easier to stimulate than the vagina when anal is happening.” The receiver can do it themselves, using a vibrator or manual stimulation.
16. Switch things up.
As you get more comfortable with anal sex with a partner you trust, you can explore different positions. Spooning is another great pick for backdoor beginners because the position gives you shared control of your movements and adds an extra touch of intimacy, which may help you relax as well. Doggy-style position allows your partner easy entry but also puts them in full control, which might not be the best for your first time. If you feel pain at any point, have your partner ease up, stop, or switch positions.
Penetration doesn’t even need to define your anal sex experience. There are different ways to find mutual pleasure that don’t involve it. “Anal play can be both external and internal,” Matatas says. “There are so many nerve endings on the butthole. Why not tease them? Try putting vibrators against the perineum or butthole, rimming, or an anal massage.”
17. Prep your space.
Your first time trying anal sex might get a little messy, so you’ll want to prepare accordingly. “Keep an extra dark towel on the floor or on the nightstand so you can put used condoms and sex toys fresh from the butt onto the towel and worry about it later,” Matatas recommends for clean up. “Also, keep lube nearby. You will need to reapply during penetration. And use latex or nitrile gloves to help contain mess and protect the delicate anal tissue from jagged or sharp fingernails.”
18. Challenge shame.
“So many folks associate anal sex with something dirty or impure,” Balestrieri says. “They may assume it means something about them, or their partner, if they like it. It doesn’t.” It’s as simple as that.
19. Look for inspiration.
“Many tips about your first time miss that, in addition to planning for physical and emotional safety and considering hygiene, sex is also meant to be pleasurable,” says Shadeen Francis, certified sex therapist. “What about anal play makes you feel curious or excited? What is arousing or interesting?”
Anal porn is a great way to open your mind to the possibilities. Use erotic audio, photos, or video to get or stay excited and look for anal sex tips. This can also be an avenue to explore any kinks and fetishes that might be of interest to you.
20. Don’t stress over it.
If you wondering when is the right time to engage in first-time anal sex, remember that there’s no right or wrong answer. For some people, anal sex is a no-go, and for others it’s a possibility. Either way is A-OK. You can have an exciting sex life with or without butt sex.
21. Check in with yourself.
Before having anal sex with a partner, or even considering how to have anal sex, make sure you’re doing it because you want to. “Know that you don’t need to have anal sex just to please a partner,” Weiss says. “The anus has nerve endings, and because it’s close to the vagina it can be pleasurable for someone with a vulva. But you should be doing it for your own pleasure, not just your partner’s. If you’re not getting any pleasure out of it, then don’t do it.”
