This is the first of a multi-part series by Charlie Glickman, PhD, for anal sex and health month.

You may not be ready to talk about it at the dinner table with your in-laws but anal sex is becoming less taboo and one of the most popular fantasies around. It can be amazingly fun, deeply intimate, and super sexy. But if you don’t know how to do it, it can be uncomfortable or downright painful.

For many folks, anal play is an act of trust and surrender. If you take the right steps to make that easy, your anal adventures are a lot more likely to be successful. And if you don’t create a sense of comfort and safety, none of the techniques are going to feel as good.

Like anything else, the best way to improve your odds of success is to know the basics. That starts by approaching anal play with the right attitude – and of course, knowledge of safety and best practices.

Don’t pressure

One of the most important things to know about anal play is that if the receiver feels any stress, worry, or pressure about it, that can make their body tighten up and the sex will be uncomfortable or even painful. It’s not something that they can control. The pelvic floor and the anus are super sensitive to feeling safe, relaxed, and comfortable. That starts with your very first conversation about it.

If you’re with a new partner, you might say something like, “I’ve been curious about anal sex. Have you ever tried it?” or “I really enjoy anal play. Is that something that you’re into?” With an established partner, you could try something like, “I just read an article in the Hustler Hollywood website about anal sex and I’m kinda interested in it. Would you be up for trying it sometime?”

All of these approaches make it easy for them to say yes or no, which gives them more room to relax about it. That’s especially valuable if they’ve had uncomfortable experiences in the past.

Also, don’t ever surprise someone with penetration, unless they have already told you that they want you to go for it without checking first. If you catch someone by surprise, their body will probably tighten up and sex will stop feeling good. Trust me- you aren’t being sneaky when you try to slip a finger in there. As with any sexual act or encounter, consent is the most paramount, and having a discussion about what your partner is comfortable with will ensure that both partners have an enjoyable experience.

Explore all your options

It’s pretty common for folks to equate anal sex with anal intercourse. But there are lots and lots of other things you can enjoy. Fingers, vibrators, dildos, butt plugs, combining anal massage and oral sex, rimming, prostate massage, the list goes on. Plenty of people love anal stimulation, even if anal intercourse isn’t their thing. So learn lots of different techniques and take the pressure off of that one act.

That’ll be especially helpful if your partner is nervous about discomfort, or if they’ve had painful anal sex in the past. The more varied your repertoire, the easier it is to have fun. Plus, it shows that you know lots of different ways to pleasure them, which is always a plus.

Don’t copy porn

One of the reasons for uncomfortable anal play is that people sometimes copy what they see in porn. But what you might not know is that there’s a lot of preparation that goes into a porn scene that never makes it on camera – and many anal scenes in porn are definitely not for beginners! Those performers are warming up hours or even days before they get on set, and they definitely apply plenty of lubricant. Since that doesn’t make it into the final product, it’s easy to think that it’s unnecessary.

Learning to have anal sex by copying porn is like learning to drive from watching an action movie: someone is likely to get hurt. Do a little research about it first. Get a book or watch a how-to movie. Take a workshop, if there are any in your area. Ask the staff at your local Hustler Hollywood store for more helpful tips, product suggestions, or to show you what books they have in stock. This is definitely a situation that improves when you have the info.

Let go of expectations

Even people who love anal sex have times when it just doesn’t work. Since the body’s ability to relax is a big factor in anal play, there are some days when it’s just not going to happen. If your mind and heart want it, but your body doesn’t, don’t try to force it. That only trains you to endure pain, which is not what we’re going for.

If you’re having a sexy date and anal play isn’t feeling great, stop doing it and try something else. It doesn’t matter if you had amazing anal sex last week. What’s important is what’s happening right now. It isn’t a sign of failure or being a bad lover. It’s simply that bodies can be unpredictable. If you can accept that and work with it, you’ll lay the groundwork for fun anal sex another time (or maybe even later that night). If you try to force it to happen, you’ll teach your body to expect discomfort or pain. That is not a good investment in your sexual pleasure.

Arousal is key

One of the most common mistakes people make with anal play is going for it without generating enough arousal first. Getting turned on makes anal play better for a few different reasons.

First, arousal helps the pelvic floor relax, which makes penetration easier. It works the same way as the vagina, in that regard. So start off with kissing, flirting, sexy talk, oral sex, erotic massage, or anything else you already enjoy before you add anal play to the scenario.

Second, when we’re turned on, things feel more pleasurable. Having someone bite your neck during sex feels much better than the same bite would feel when you’re writing an email. In the same way, if the receiver isn’t turned on enough, anal play won’t feel as good.

Third, and perhaps most important for folks who are new to anal, when you combine a new activity with something familiar, you help your body connect the pleasure with the new experience. Since the body is already aroused, it starts to associate that feeling with the additional activity. Some people will get to a point where they enjoy anal play without any additional stimulation, and others will find that they always like to combine the two. There’s nothing wrong with either way of doing it. It’s just a matter of how different bodies are wired, so do what works for you.

Don’t endure discomfort

Anal sex can go from amazing to ouch pretty quick. Maybe the lubricant dried up and you need some more. Maybe your leg is cramping or your partner shifted angles and it doesn’t feel good. Maybe you want to switch positions. Whatever the reason, it’s a good idea to deal with it rather than putting up with it.

The longer you endure uncomfortable sex, the more your arousal will drain away until you’re just hoping the sex will end. A lot of people keep quiet and hope that their partner will do something different, but by the time that happens, the fun has evaporated. So speak up and fix whatever needs fixing. (And if your partner asks for something to make the sex feel better, thank them for telling you. It’s not an easy thing to do, so a little thanks will help.)

What next?

Most of these tips focus on creating the right attitude to make anal play fun. While it’s definitely important to also know techniques, you can have the best skills in the world and still have bad sex because you’re rushing to intercourse or ignoring your body’s signals. So now that you’ve learned how to approach anal sex, keep your eyes open for more articles with plenty of how-to tips and ideas to make your backdoor adventures amazing!


About The Author

Charlie Glickman, PhD is a sex & relationship coach, a sexuality educator, a sexological bodyworker, and an internationally-acclaimed speaker. He’s been working in this field for over 25 years, and some of his areas of focus include sex & shame, sex-positivity, queer issues, masculinity & gender, communities of erotic affiliation, and many sexual & relationship practices. Charlie is also the co-author of The Ultimate Guide to Prostate Pleasure: Erotic Exploration for Men and Their Partners. Find out more about him on his website or on Twitter and Facebook.