Hi Pillowtalk,

My girlfriend wants to peg me. I’m really struggling with whether or not I want to do it—but I do want to try new things, and she seems really excited. Do you have any advice on how to get comfortable with it?

My first and foremost advice is to never do anything you don’t want to do. My second piece of advice is that it’s sometimes a good idea to expand your comfort zone! It can make sex more exciting and more fun, especially if it’s gotten a bit monotonous. That said, peer pressure is a big issue, especially coming from a partner. Be wary of that when making your decisions—are you being coerced at all? Will you regret making this decision?

In reply to your question about getting comfortable, though, I have some more practical advice. Read some people’s positive and negative reviews of anal sex! Search the questions you have, maybe watch a little homemade porn and read a blog post. Get the gist of the experience you’re anticipating.

Talk to your partner about your concerns, and ask how she sees it playing out. Visualize the experience, collaborate with each other around boundaries and comfort, and see if that influences your comfort with the concept.

I’ll give you some anatomical context and advice too. As you may know, pegging refers to anal sex, usually anal sex where a man is penetrated by a woman. Anal sex is a really common form of sex, especially for people with a prostate (assigned male at birth). The prostate is very easily accessible through the anus, but can also be stimulated through the perineum (or “taint”). The prostate is a gland that contributes fluid to semen. It can be reached a few inches up the anus towards the front of the body and has been compared to a walnut in size. For most people, prostate stimulation is a big factor in trying pegging for the first time.

To get comfortable with this, try incorporating anal elements in your masturbation. Take a shower and take a look down there, familiarize yourself with the area. Use so much lube it seems ridiculous, and start slowly by just touching the outside and combining that with a stimulus you find arousing. Try using your fingers when you get a little more into it. Or, integrate it into your foreplay with the same intention. Use so much lube, and use fingers or tongues to play a little and get more comfortable. If you find yourself incredibly turned off by it and don’t want to continue to penetrative sex, that’s fine. If you find yourself really liking it but not ready to move forward, that’s okay! You can keep those activities in your repertoire without having penetrative anal sex.

Or, keep going! Buy a dildo, or get a beginner set of strap-on accessories with multiple sizes and a good bottle of body-safe lube (not flavored!). Work your way up to comfortable penetration on your own, or along with your partner, before putting the dildo on your partner and having them control it. 

If you do decide to have anal sex, keep a few things in mind! It might be messy. That’s a risk you have to take. Enemas or anal douching can make it less messy, but they can also thin the mucus in the anus and cause microtears that can lead to infection. If you use an enema, use a liquid safe for anal use, do your research beforehand, and use so much lube. Luckily, if you’re using a dildo, cleanup is pretty easy. You can also use a condom for easier cleanup, and put a towel down just in case. Poop beforehand, and you should be just fine!

Go very slowly! The anus is a sphincter and has a fundamentally different kind of “stretch” than the vagina. Most of the grip will be in the outside ring of muscle, so it’s important to increase girth gradually to prevent tearing and pain. Stop if there is blood.

Overall, just take it slowly, communicate a lot and continually evaluate your comfort and pleasure. And, as always: use so, so, so much lube.