Ready to Try Anal? Here's How (Without Freaking Out)

Since becoming an adult, there are a few things that pretty much no one likes to talk about except for me: money, the Jonas Brothers, Vine, privilege, my acne, and anal sex.

Get over the stigma

First of all, basically anyone can have anal sex. According to Bailey, if you have any ailments such as anal fissures, you’ll want to talk to your doctor to know what precautions you’ll want to take during sex; but otherwise, all consenting adults can have and enjoy anal sex, regardless of the stigmas and bad press it often gets.

However, it is very common to be uncomfortable about trying it for the first time. I mean, it is a totally different sensation that doesn’t exactly seem all that pleasant when you first think about it. Bailey explained that once women educate themselves on it, though, they’ll begin to unravel those stigmas. “Many women desire to have anal sex, and it can be a source of great pleasure and some pretty intense orgasms,” Bailey said. But don’t overthink it too much—it’s just another normal sexual act that lots of people love, and you might too! She went on explaining that a big tool in educating yourself includes talking about your reservations, fantasies, and questions with a person you trust: a partner, friend, or therapist/sex therapist.

With those trusted confidants, you can begin discussing your fears. Are you afraid of having a bowel movement (I haven’t talked to someone who’s said this hasn’t gone through their mind!)? Are you worried it will hurt? Are you afraid of not enjoying it? These fears are important to discuss with a partner so you can comfortably communicate and address if these fears do come true. (As for the first one, it’s not as likely as you think!)

Set boundaries

Deciding to have anal sex is a big decision, and don’t let someone else tell you differently. Your body, your rules. If you feel as if your partner is pressuring you into having anal sex, think inward about if it’s something you truly want. “Setting boundaries with partners include … owning your own emotions and actions surrounding anal sex,” Bailey said. Tell your partner how you feel about it and what exactly you want out of the experience. Maybe you want to start with finger play first to see if you’ll like it. Bailey said to communicate with your partner in a way not to make them feel shamed or embarrassed for asking or discussing this with you as well. “Be sure to not pressure yourself or feel guilty for setting limits,” Bailey said.

Prepare yourself

Many people know they have to prepare physically for anal sex, but it’s also a good idea to prepare yourself mentally too. Bailey recommended starting with “knowing your why” by asking yourself why you want to experience it, is it something you desire, are you just trying to please your partner, do you feel pressured—asking yourself these questions to make sure you have a strong understanding of why you want to try it. If you feel pressured or are just doing what your partner wants, it’s unlikely you’ll enjoy it.

Bailey explained women should educate themselves on solo anal play, anal hygeine, and anal toys. “The more informed you are, the more confident one can feel,” Bailey said. As far as anal hygeine, she recommended emptying the bowels 30-60 minutes before engaging in anal play (whether with a partner or solo). Then, wash the area with soap. She also said using an enema 1-2 hours before can deep cleanse the area as well.

Before you even try anal with your partner, it’s a good idea to try solo anal play. Being comfortable with that area on your own will make it a lot easier to feel comfortable with your partner and to help tell them what it is you like and dislike. Bailey gave us the 411 on trying an external anal massage for the first time. Lay down a towel underneath you. Apply lube to your fingers (you can use hypoallergenic gloves if you’d like). Begin by lightly touching one spot—Bailey explained this should be relaxing, so you can take in how the sensation feels. Then, you can start tracing your fingers in circular motions around the anus. Once you feel comfortable with that, you can increase the pressure and go at a faster pace. Bailey then recommended trying different breathing techniques, which are important in showing you how the anus expands while you’re breathing. This should be relaxing and full of pleasure, rather than tense and uncomfortable. Make this a sexy moment. Put on lingerie, play some music (I love The Weeknd and Drake’s Take Care album for sexy music), and let loose. Bailey suggested lightly touching yourself elsewhere (such as your legs, your breasts, your stomach—the works) to keep your arousal up.

Anal isn’t just like vaginal sex; it’s not made to have things go inside of it. It’s not elastic, it’s a muscle, and muscles need to be trained just like your bis and tris. Once you’ve done anal play on yourself, you can start trying with a partner. Place your focus on anal play with fingers at first, getting used to the sensation and preparing your anus to try this fun, new thing! Make sure to use lots of lube, go slow, and be open and honest about communicating with your partner.

Don’t forget to use condoms

Just because you’re not at risk of pregnancy doesn’t mean you can’t spread bacteria and STIs through anal sex. If you’re into natural condoms, here are the ones we recommend.

Try different positions

Although doggy style is the position you likely first thought of for anal sex, it might not be the best for you and your partner. You on top allows you to control the speed and depth, putting you in charge of what’s going on down there, which might make you feel a little more at ease. Missionary also allows a little bit of control on your end and might feel really comfortable and familiar. Spooning is also a good position to try as a beginner; you and your partner are able to get really close while also sharing the control. Trying different positions allows you to know what works best for you. If you feel any pain or discomfort, stop, take a break, and bust out a different position to see if that eases up.

Breathe and go slow

Like we said, the anus isn’t meant to take penetration like the vagina, so it’s important to calm down, breathe, and go slow. There was never a more prevalent time to say “go with the flow” than when you first try anal sex. It will feel awkward, weird, and maybe like you have to go to bathroom—and that’s exactly how it should feel. Take deep breaths through it, and keep going with it (unless it does become painful or uncomfortable enough to want to stop—this is where boundaries and safe words come in). This is also why it’s important to have your partner thrust in very slow and controlled movements.

Remember when you first had penetrative sex and it hurt a lot and then felt fine and then felt pretty good? That’s how anal sex goes too. If you’re having sex with someone with a penis, the head is, generally, the widest part, so once you get past that, it’ll start to feel better.

Add toys

If you want to try anal play but aren’t quite ready for penetration, toys are a great way to get yourself up to it.

On the other hand, you can also use vibrators while you’re engaging in anal play to add clitoral or vaginal stimulation. While your partner is penetrating you anally, grab a vibrator to up the sensations.

If you use any toys anally, remember to properly clean them before using them vaginally (and after every use, of course).

Never go from anus to vagina

If you and your partner decide to move on from anal to vaginal sex, make sure your partner cleans themself or whatever toy they’re using first. Bacteria can easily travel from one to the other, and we don’t want any UTIs, BV, or yeast infections right now.

Don’t like it? No problem

If you hated it, you never have to do it again! That’s the joy of trying new sexual things—there’s no obligation to ever do them again. What ever will you try next?

Ready to Try Anal? Here’s How to Do It (Without Freaking Out)