#AskPlayboy: Jenny Mollen on Threesomes

This is gonna sound kind of crazy, but my girlfriend recently proposed the idea of a threesome (the good kind of threesome, the kind with another girl), and I’m horrified. It’s not like I haven’t considered a threesome as part of a wild sex fantasy, and I’m definitely into it, but now that I’m faced with the reality of actually doing it, I’m not sure that I want to. The mechanics of it seem crazy; I just got comfortable with the idea of satisfying one girl, now I’ve got to worry about two? That’s a lot of work for me. But this is every guy’s dream, right? And she proposed it! Do I just need to put any awkward inadequacy issues aside and man up, or do I tell her that the prospect of this is scaring me shitless? Should I just watch them have at it so I don’t have to worry about underperforming?

A: Take it from me, threesomes with someone you actually care about are hard! A wise whore once said to me, “There are three things that could possibly happen here that I want to prepare you for: One, the girl could get jealous, causing the guy to freak out and lose his erection. Two, the guy could get jealous, causing him to freak out and lose his erection. Or three, everybody could be having a great time but the slightest wrong vibe could cause the guy to lose his erection.'

If you are going to do this, please use a professional. Friends or acquaintances just make things messy. If you are in a relationship with one of the people in your ménage, the undercurrent of what is actually going on psychologically can be hard to navigate and the tides tend to shift fast. Take a Viagra and just calm the fuck down. You aren’t expected to be some sort of gladiator in the sack. I’m sure part of the appeal for your girlfriend is performing for you. I can also tell you that she is getting off on your being uncomfortable. My favorite thing about having threesomes with my husband is that it is never his idea. Oscar Wilde put it best when he said, “Everything in the world is about sex except sex. Sex is about power.” If she wants to fuck somebody with you, it’s about power, most likely hers. So let her lead it. There is literally zero pressure on you. Just play it cool, DON’T ACT LIKE YOU WANT IT (because then, of course, you won’t get it) and enjoy the ride. Also, if you want further advice on what NOT to do, enjoy this blog post at my personal expense: thesmokingjacket.com

Read more of Jenny's Columns here.

Jenny Mollen is a writer, actress and all-around gorgeous sassy badass who lives in L.A. with her dog Teets and husband Jason Biggs. She writes about her life on TheSmokingJacket.com in her highly popular column What She Said. Follow her on Twitter at @JennyAndTeets and on Instagram at JennyAndTeets2.