Sex & Pancakes

Dear Melissa,

My girlfriend and I want to try anal, but here’s the thing. She wants to fuck me with a strap-on. I’m a hetero guy and have never been the ‘catcher’ in this situation. I’m a little nervous about it and I can’t avoid it now because she keeps bringing it up.

From, Catcher

Dear Catcher,

It sounds like you’re open but nervous to the idea of pegging (when a female penetrates a male with a strap-on).

Hetero or not, anal stimulation of the prostate gland is something any man can enjoy, but you need to ask yourself if you WANT to be the “catcher.” Are you nervous because it’s something you don’t want, or because you do but it’s a new experience? Your girlfriend bringing it up shouldn’t be your only reason for doing it and if you really don’t want to then chances are you’ll be reluctant, really nervous and you might even resent your girlfriend if things don’t go well.

If you decide you’re open to trying it out, take it slow and relax. The worst way to go about anal sex for the first time is with a “let’s just get this over with” attitude. When you’re nervous your muscles tense up—including the ones in your ass, which can make things painful for you, so try easing into it with something easy like a finger or small toy.

It might also help to do this a few times before moving up to penetration with a strap-on if you’re really nervous because the more comfortable you are, the more you’ll enjoy yourself.

The anus is prone to small tears and cuts because it doesn’t produce natural lubricant so use lots of lube because it’ll make the whole experience easier. Although all sexual activity poses a risk for STIs, a condom isn’t necessary if you’re only penetrating the anus with a toy but be sure to give any toys you use a good clean before and after, as well as if you plan on using the same toy on your girlfriend. However, if you’re both using the toy you might choose to use a condom because it can make for quick and easy clean up between since you’d just need to change condoms.

Though I’m not familiar with the joys of male anal sex first-hand, I have it on good authority that it’s pretty damn awesome. I’m also going to direct you to a great site where you can get further tips on first time anal sex in case you have more specific questions. has articles on preparation and a forum where people share their advice and first time experiences with anal. It’s really helpful and a lot of them make for some steamy reads on their own.
Finally, anal sex on either partner is intimate and requires trust because like anything, things don’t always go perfectly. Do you trust that your partner will stop if you realize that it’s not for you? Do you trust that she’ll let you be in control of the pace? These are important factors and things you might want to talk about together if it’ll help put your mind at ease.

Good luck, and don’t let fear keep you from pegging!

This article originally appeared in Volume 31, Issue 20, published January 25, 2011.