Four Things You Need To Know To Have Awesome Anal Sex

It probably won’t surprise you to hear that I love anal sex. After all, I’m one of the authors of The Ultimate Guide to Prostate Pleasure, and I teach lots of workshops about anal play, prostate massage, and related topics. Of course, that’s not all I do, but given how many people fantasize about anal sex, it’s no wonder that I get a lot of emails and questions about how to do it and make it fun.

The tricky thing about anal play is that you really do need to know what you’re doing if you want want it to feel good. The nerves in and around the ass are exquisitely sensitive, so they have a lot of erotic potential. That also means that if you don’t do it right, anal play can go from amazing to ouchy really quickly. My book and workshops have all of the how-to tips to make it pleasurable, but the right attitude is even more important than the technical skills. So here are a few tips to help you make the most of your anal adventure.

1. You’ll Get There Faster When You Slow Down

One of the many ways in which porn is terrible sex ed is that the performers almost always just dive right in, without any warm-up or lube. That’s because all of that happens before the camera gets rolling. Unfortunately, when viewers copy what they see on the screen, they can easily hurt themselves or their partners. Many of the messages I receive are from folks who want to know how to make anal sex more comfortable and more often than not, part of the problem is that they’re going too quickly.

The number one best suggestion I have for making anal sex amazing is to slow down. Way down. Even slower than that. Trust me.

There are a few different reasons why this can help. First, the internal anal muscle is controlled by the autonomic nervous system. As a result, while practice and experience can help us influence it, it’s not entirely within our control. It’ll squeeze and tighten up anytime we feel stress, anxiety, worry, or discomfort. So if you’re moving faster than the receiver’s body wants, their ass will probably clamp down in a protective response. The best way to keep that from happening is to go super slow and invite their ass to relax.

Second, the slower you go, the more attention you can give to the small changes in your partner’s arousal and make adjustments as needed. Even folks who are very experienced with anal play can enjoy the experience more when you start off slowly.

Third, there are two distinct sensations that can affect how someone enjoys anal play. First, there’s the relaxation of the anal muscles as they open up. A lot of people like the way that that stretch can feel. Second, there’s the in-and-out feeling as a finger, toy, or penis moves back and forth. If the muscles aren’t relaxed enough yet, there can be too much friction with that in-and-out sensation because the anus is squeezing and increasing the pressure. That friction can be uncomfortable, even when there’s plenty of lubricant. The slower you go, the less friction there is. Once the receiver is more relaxed and turned on, that becomes less of an issue.

One of my favorite kinds of hands-on coaching sessions with couples is demonstrating just how slow I mean by showing it on the receiver, and then guiding the giver as they practice it. More often than not, the giving partner thinks that they’re slowing down enough, and I tell them that they’re at a 7 when I want them at a 3. It makes a difference.

Of course, people who are familiar with anal play, and know both what they like and how their bodies respond can often speed things up. But that’s something that comes with experience. So it’s usually a better idea to start more slowly and then speed up than to go quickly and make it less fun than it could be.

2. Let Go Of Your Expectations

When most people think of anal sex, they assume it means intercourse or at the very least, penetration. But you don’t need to do that to have a great time with anal pleasure. In fact, it can feel wonderful to focus on the external muscle and the skin around it, without any penetration at all.

The more pressure you put on your partner or yourself for a particular outcome, the more difficult it can be to enjoy the erotic possibilities because the resulting stress can get in the way. And even folks who have plenty of experience with anal play can sometimes not be into it because they had a rough day. I’ve worked with a lot of people who have tried to make their bodies enjoy something that just wasn’t in the cards that day, and the more they tried to force it, the worse it felt.

If you can let go of any expectations about what kinds of pleasure you’ll be exploring, and focus instead on what feels good in the moment, you’ll create much more room for enjoyment and arousal. Sometimes, that might create opportunities for penetration, but don’t worry about it if it doesn’t happen. In fact, if you learn how to have fun without pushing for a particular kind of anal play, you might find that a future session goes more smoothly because both know that you’re enjoy the ride no matter where it goes.

The more you can follow the pleasure without expecting any specific route, the more you and your partner will enjoy anal play. It helps if you know lots of different ways to do that, and you might be surprised to discover just how many options you have. There are a lot of pleasures your hands and fingers can bring to your partner’s ass. It’s not complicated, but it’s also not always intuitive. The DVD Anal Massage for Relaxation and Pleasure will show you everything you need to know and you can find it on Amazon or you can stream it from the New School of Erotic Touch. You can also learn a lot from Jaiya’s DVD, Exquisite Anal Massage.

3. Don’t Forget To Include Other Pleasures

Whether your anal play includes penetration or not, one of the best ways to make it feel awesome is to bring your partner’s other erogenous zones into it. It’s easy to get so focused on what you’re doing to help them relax and feel good with the anal pleasure that you forget the rest of their body. That means you’re missing out on a lot of the erotic potential.

This is especially important for folks who are just beginning to explore anal play. I’ve found that a very effective way to bring something new into your sex life is to make it an add-on to a familiar pleasure. Arousal makes things feel better, and doing something that you know you like makes it feel safer. Think of it as making the new thing a side dish rather than the main course.

It can be tricky to give your attention to your partner’s ass while also pleasuring their penis, clitoris, vagina, or other sensitive spots (don’t forget the nipples!), so one great way to make it work is to have them use their hands or a sex toy while you focus on their butt. Remember that anal play doesn’t have to be only about the ass, unless they want it to be.

4. Touch Them With Care

In addition to being full of sensitive nerves, the anus is a place where a lot of people hold many different emotions. In particular, we often hold challenging feelings like anger, fear, or shame in the pelvic floor. And when those emotions are linked to past experiences of painful sex or sexual trauma, they can be held even more tightly. So it’s quite common for people to have many different feelings come up as they learn to relax the pelvic and anal muscles.

One of the most important things you can do to make anal sex fun is to touch your partner with care. Bring kindness to your hands and you’ll tell their body that you care about them and how they feel. That doesn’t mean you can’t have hard, raunchy sex. Touching with care doesn’t require you to be gentle. Consider how an intense, deep back massage can be given with care while also being quite powerful. If you want to have intense anal play, you can still do it with care.

When you give your attention to your partner, you bring yourself into to the present moment, rather than getting caught up in your fantasies or your expectations for how things will go. That gives you the room to focus on how you touch them and what you communicate to them through your fingers. People can feel that, even if they don’t know how to put it into words. And when your partner feels your care for their body, their pleasure, and their heart, they’ll feel more safe. That creates more relaxation and expands their capacity to feel good.

This All Sounds Familiar

Of course, you don’t have to only do these things with anal play. Slowing down, releasing expectations, including more of your partner’s pleasures, and touching with care can make any kind of sex hotter and more fun. That’s because they lay a foundation of safety and comfort, which is what makes it possible to build the passion and energy.

At the same time, the anus is so physically and emotionally sensitive that creating that foundation can be even more important than for other sexual pleasures, at least for many people. That’s especially true for anyone who has ever been pressured into having anal sex that didn’t feel good, or for anyone who has been sexually assaulted. I coach a lot of people who have had partners talk them into anal sex that they didn’t want to have, or who didn’t understand how to do it right, or who have had painful anal experiences, or whose consent and autonomy have been violated. Anytime those folks decide that they want to explore anal pleasure, I tell them that these four steps are essential. If they (or their partners) don’t feel confident in their ability to do all of them, I help them learn those skills as part of learning how to make anal play feel good. They often find that the rest of their sex lives improve, too.

Where Can You Learn How To Do All Of This?

One of the challenges that I see couples face is that anal sex is much easier to do when at least one partner knows what they’re doing. When both of them are newbies, there’s a lot more room for missing some of these steps. Fortunately, there are some great resources out there. In addition to The Ultimate Guide to Prostate Pleasure and the movies I mentioned above, I also recommend Tristan Taormino’s The Ultimate Guide to Anal Sex for Women. Tristan also made three great how-to movies: The Expert Guide to Anal Sex, The Expert Guide To Advanced Anal Sex, and The Expert Guide To Anal Pleasure For Men.

You can also come to one of my workshops on anal play, which I teach all over the US and Canada. If you don’t see one scheduled in your area, I’m available for private classes. If you have a group of friends who’d like to bring me out to you, get in touch with me and let’s see what we can make happen.

And lastly, if you want customized instruction, I’m a certified somatic sex educator and I offer hands-on educational sessions. Bring a partner and I’ll coach you through everything you need to do to make anal play amazingly fun for both of you. You can find out more about that here.

And in the meantime, remember: slow down, let go of your expectations, include other pleasures, and touch with care. If you do all of those things, you’re on your way to awesome anal sex.



I'm a writer, blogger, teacher, workshop facilitator, sex & relationship coach, and a certified somatic sex educator. I teach workshops and seminars on many different sexuality topics, including sex-positivity, sex & shame, communities of erotic affiliation, many different sexual practices, gender & masculinity, and sexual politics. Contact me for more information, to arrange a speaking engagement, or to find out how I can help you create an amazing sex life.

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Published by Charlie

I'm a writer, blogger, teacher, workshop facilitator, sex & relationship coach, and a certified somatic sex educator. I teach workshops and seminars on many different sexuality topics, including sex-positivity, sex & shame, communities of erotic affiliation, many different sexual practices, gender & masculinity, and sexual politics. Contact me for more information, to arrange a speaking engagement, or to find out how I can help you create an amazing sex life.

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  1. Charlie


  1. Hi

    I’m having trouble locating the prostate on my wife of 43 years. Is it an age thing? Or am I not doing something right?

    Many thanks,

    Lewis (Lew for short)

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