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When Anal Sex Doesn’t Work

Here’s a question that showed up in my in-box today:

Sometimes, when my boyfriend and I have anal sex, it’s really fun. But other times, it just doesn’t work. That doesn’t happen when we have regular intercourse. What are we doing wrong?

It’s sort of hard to give you a specific answer since there are lots of things that make anal sex awesome and you need to do them every time. But there are two thing in particular that I think might help with your on-again, off-again enjoyment of anal play.

First, you need to know how the anatomy of the pelvic floor and anus work. The external anal muscle (the first one that you would touch with a finger or toy or penis) is made of skeletal muscle. This is the kind of muscle that you can consciously control, like when you move your arm or foot. But the internal muscle is made of smooth muscle. These muscles are in your organs, your digestive system, your blood vessels, etc. No matter how much experience you have with anal play, you can’t ever get 100% control over the internal muscle.

That’s important because the pelvic floor tightens up when you get stressed out. Think about how a cat or dog tucks their tail when something scary happens. Your body does the same thing, and it doesn’t really matter where the stress is coming from. If you had a really busy day, or if you were stuck in rush hour traffic for two hours, or if you’re worried about whether anal play will be fun this time, it can make things tighten up. And that can make anal sex less fun. Even folks with lots of anal play experience can have it not work after a bad day.

So if that’s part of your situation, don’t let it stress you out more. Do something that does feel good, even if it’s not anal play. Or have fun with external anal stimulation without penetration. Or use a finger or a slim toy, rather than a penis. You can still have a great time. And the next time will probably be easier since you’ll know there’s no pressure.

Second, it’s important that you seduce the ass. Every time.

What I mean by that is that since your body can respond so differently from one day to another, you’ll have the most fun with anal play if you start every session as if you were brand new to it. Take it slow and invite your body to relax and open up. Don’t rush it, no matter how turned on you are and no matter how easy it was last time.

When you do that, you’ll be able to give your attention to your and your partner’s response. If that means that this time, you have to keep things slow or not go as far, you’ll know that before things get uncomfortable. And if your anal pleasures come together more easily, you’ll be able to ramp things up with more confidence. So take it easy and start off as if it’s your first time.

Have fun!



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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One Response to When Anal Sex Doesn’t Work

  1. Vic says:

    Hi Charlie,

    Straight guy here who loves and has always loved anything anal related but of course, has kept it under wraps for fear of discovery. My desire to be penertrated by another male is constantly on my mind. I back-burner it (no pun intended) because I have no clue as to how to go about realizing my desire. Like, where should I even look for that! Oh Lordy, I know you probably can’t even answer that … But maybe you might drop me a clue. Am I alone?


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