Q: My new girlfriend is a dynamo in the bedroom. She loves giving blow jobs, taking it from behind, being spanked, etc., and wants to have sex four times a week. Because she is so outgoing in bed I would like to approach her about pegging, something I have wanted to try but didn’t have the opportunity to discuss with my past sex partners who were less open-minded. I’m only hesitant because the things she seems to like the most are the times where I’m in a dominant role and she’s in a submissive one. I don’t want to get shot down and have it affect this great thing we have in the bedroom. How can I approach her about this subject and not completely turn her off if she’s not into it?

 

A: Pegging, for the I’m-new-here crowd, is when a woman dons a strap-on dildo and uses it to anally penetrate her male partner. It’s typically and perhaps falsely associated with BDSM scenarios in which the woman uses various apparati to inflict pleasurable pain. Some misinformed members of the peanut gallery might also say that enjoying pegging is a sign of bi- or homosexuality, because anything that has to do with a dude’s butt automatically equals gay, duh. Esteemed readers of this column know better. The anal opening is full of nerve endings that can provide pleasure for men and women when stimulated just so. Men also have the prostate tucked just inside, which can make for mind-blowing orgasms when prodded.

I’ll assume you’ve at least messed around with anal play, whether it was a partner wiggling a finger in your butt during sex or playing with a dildo during masturbation. If you’ve never had an item inserted in your anus before, brace yourself for a special kind of awkward sensation that may abruptly make you wish you were the only person in the room. On the other hand, you might bellow in pleasure and beg for her to go deeper. Pegging is a totally different experience, not just physically but psychologically. As a man accustomed to being dominant in bed, you know there is a power exchange that happens when the clothes come off: Suddenly, you’ve got nearly all of it, and that’s enjoyable for you. Likewise, some women, when assuming a more masculine role in bed, will take that power and run with it. If your girlfriend gives pegging the green light, you need to first sit down and establish a protocol. You have to be safe, which means using ample amounts of lubricant and starting out slowly and gently. You must also be communicative, which means letting her know if and when you’ve had enough and want to stop.

If she seems hesitant about the potential role reversal, remind her that that pegging doesn’t have to be done while you’re on all fours and she’s behind you. You can easily be penetrated while you’re in the missionary position, or just seated on top of her. You’re able to watch her do her thing and she can watch you stroke yourself as you both get off. If she’s down to be tied up, incorporate a little light bondage. She can remain her submissive self while you stay on top, calling the shots.

To broach the topic of getting pegged, try a neutral setting when you’re both relaxed and you’re not going to catch her off-guard. If she already lets you put things in her butt on the regular, and you’ve just had a steamy, all-inclusive sex session, bring it up in the post-coital cuddle. Ask if she’s ever thought about doing the same to you, and if she’s interested in trying it sometime. Tell her that she makes you feel open and uninhibited about sex, and you want to explore other possibilities with her. Given your sexual chemistry, I’m sure she’ll be open to sharing a new experience together, or at least give it some genuine consideration.