Will It Hurt?

The most direct way to massage the prostate is through anal penetration, and a lot of folks worry that penetration will hurt. Many people have had painful or uncomfortable anal penetration attempts, or have heard from others who have. So it’s not surprising if you or your partner are worried about pain. But trust us: with a few simple steps, anal penetration can be easy. In fact, a lot of guys like anal stimulation on its own, even before they find the prostate.

In order to insert a finger or toy into the anus and reach the prostate, you need three key ingredients: relaxation, lubrication, and communication.*


Contrary to what you might have seen in porn movies, anal penetration isn’t about stretching the anus open. Instead, it’s about the receiving partner being able to relax the anal sphincters – the two rings of muscle that hold the anus closed. That takes a bit of practice, but we have lots of good tips to make it easier.

The ability to relax the anal sphincters and accommodate penetration is strongly influenced by your state of mind. If you’re stressed out or worried, it’ll tend to tighten up in much the same way that a scared dog or cat will tuck its tail between its legs. It’s a protective mechanism, but your body can’t tell the difference between being anxious about work or being nervous that anal play will hurt–they both make things tighten up. In a vicious circle, the tightness makes penetration uncomfortable, so things tighten up even more. At that point, you might decide that it’s just not going to work and give up. Or worse, you may force penetration, and not enjoy yourself at all.

Fortunately, you can learn to relax and control the anal muscles. And since you can have an amazing prostate experience with nothing more than a finger or a slim toy, you can explore the prostate even if you are still learning to relaxing the sphincters. As you become more familiar with the sensations and get more practice, you might enjoy more fingers or larger toys, but there’s no reason to get goal-oriented about it. The point is to enjoy what works best for you. Check out our page Relax Into It for some tips.


Since the anus and rectum don’t lubricate in the way that the vagina often does, you’ll be much more comfortable if you use a lubricant. There are a lot of different choices out there and we describe the pros and cons of the various sorts here.

Even if you start off with enough lube, you’ll probably find that it feels better to add more every now and then. Some lubricants dry up after a while as your body absorbs the water in them. But even oils and silicone lubes disappear during a longer session. So keep the bottle handy and add some more whenever you need it.


Being able to talk with your partner about sex before, during, and after is always one of the best ways to make sure you’re both having a great time and to build trust between you. That’s especially true for anal play, since the anus and the rectum are so sensitive. Telling your partner that you’d like to try a different position, or that you need more lube, or that you want to see what another finger feels like will help ensure that you both have fun.

That’s even more important if you feel any discomfort. Your partner might try a massage technique that simply doesn’t work for you. Or they might accidentally poke your prostate instead of stroking it. Or the dildo might go a bit too deep. Whatever the reason, there’s no reason to tough it out!

Although it’s easy to say “talk about it,” you or your partner might find that more challenging than you expect. We have lots of suggestions for talking with each other, before, during, and after your prostate exploration!

Don’t Copy Porn

You might have noticed that a lot of porn movies make anal sex seem really easy without incorporating any of these tips. The performers dive right into it without any warm-up, there’s rarely any lube, and they certainly don’t talk about what they like or dislike. We’ve spoken with quite a few people whose anal experiences are uncomfortable or painful because they copied porn.

You wouldn’t know it from the movies, but the performers do warm up and apply lube. It just happens before the camera starts. It’s kind of like a cooking show- you don’t see the washing and chopping. All you see is the ingredients already prepared. They do that to keep things moving quickly, but it can sometimes create unrealistic expectations.

If you enjoy erotic movies, fee free to use them as inspiration. But don’t expect them to show how to make anal play work. As we like to say, learning how to have sex from watching porn is like learning how to driveĀ  from an action movie. Somebody is likely to get hurt.

For many more tips on painless and pleasurable anal penetration, our book has everything you need to get started!

* We’re indebted to Dr. Carol Queen and Dr. Robert Lawrence for teaching and talking about anal play, and for sharing this language with the sex education world.