The Chicagoist will be launching later but in the meantime please enjoy our archives.

Ask Chicagoist: Why Can't We Go On As Three?

By Thales Exoo in Miscellaneous on Aug 16, 2007 3:00PM

2007_08_askthreesome.jpgDear Ask Chicagoist,

I'm really interested in having a threesome (FMF), but I've never done that before. How do I go about facilitating something like this? What are the pitfalls that I should worry about, and what are some of the benefits that I, and my potential partners might enjoy as well? Is it possible that this could be an event that happens more than once or twice? What is the possibility that our triad could become a regular thing, if not a deeper relationship?


Is it wrong that we are naturally assuming you're the "M" in your situation? We're not (really, we're not), saying that it is completely out of the question for "F"s to have a ménage à trois fantasy (it's not just a wine anymore!), but statistically speaking we're pretty sure we're on the money here.

Still, we're all for people having healthy sex lives, and as a general rule think that people would be happier and the world would be a more peaceful place if people would just embrace their carnality rather than hide from sex in shame. But that doesn't seem to be your issue, you're just hoping to expand your areas of experience.

You want to have a threesome. Are you already in a relationship with someone? Or if not a relationship, at least a fairly reliable sex-buddy situation? We're going to assume "yes" or you're really starting from scratch and might want to consider posting a Craigslist Casual Encounter ad ("Random guy looking for two hotties for three-way action. Really. I'm expecting hundreds of real responses so please give provide a picture.") Unless, sad to say, you're hiding important aspects of your fame and celebrity from us, we would advise against holding your breath. Yes, we would imagine there's a starfuck power out there that would make it not too hard for a select few in our society to make good on this fantasy. We're going to hazard a guess though, and assume George Clooney is not writing in to Ask Chicagoist.

OK, so we'll go with the scenario where you're in a relationship (of some sort -- again, even an established sex-only relationship is fine here), she claims she's into it, and you want to find a third. Wait -- first, we don't want to sound so disparaging, and we insist we are not anti-threesome. Our personal experience is perhaps not the point, but if everyone's into it and everyone's having fun, we say go for it. It can be fun! And a little (or a lot of) alcohol may not hurt, either.

Step one we think is making absolute certain that your partner really is as into it as you. Or if not "as" into it, is at the very least not just saying "Yeah, uh-huh Honey, sure, we'll have a threesome. Pass the peas please." Really talk about it. Don't just let out a Homer "woo-hoo!" and run out propositioning every woman you meet. Figure out the ground rules. Should it be someone you know? Does she know someone? Would the random stranger be a better choice? Are there any rules during the big event? Figure out what's going to make the two of you comfortable, then go out and find someone.

An exceptionally open-minded friend who you're pretty sure would be into it is one way (you know who we're talking about, we all have that friend), a few nights out socializing with new people may be another, or of course there's the internet. There are any number of not-safe-for-work sites out there (let google be your guide) that could help you find like-minded individuals. And honestly, get to know the third person before hopping in the sack. Make sure it's an actual fit, and not just the only person who answered your personal ad. Maybe have a few "sex-free" dinners and plenty of conversation.

No ground rules needed? Casual sex only? Well keep this in mind: as open and sexual as we all can be, we can't help having feelings. Control yourself, please. Make sure everyone has some time -- equal time, in fact -- as the center of attention, and don't rush to the finish. Nothing sucks more than feeling, quite literally, like a third wheel. We all know what you, "M," have in mind when it comes to your fantasy (we've seen the movies too), but just like with single partner sex, do make sure it's not all about you. Because honestly? It's not at all about you. Let's face it, you're easy. Therefore, it's got to be all about the two women in your bed. Especially if you would like a second go-around and would like to avoid having two people pissed off at you.

Pitfalls? Well there's the omni-present sexual pitfall of STDs and pregnancy, so we hope you play smart and safe. Especially if you don't really know who you're getting in bed with! Make using condoms and dental dams a sexy part of the event. Plus there's potential jealousy, awkward feelings later if you know the "third" in real life, or uncomfortable feelings during if you don't share and take turns. There's no I in threesome. We can't emphasize enough the psychological aspects, actually, and if you are considering this with someone you're in a long-term relationship with, a trip to a like-minded therapist couldn't be anything but beneficial, just to make sure you aren't on track for creating some irreparable damage.

Benefits? We imagine you mean other than pleasure and hot sex? Better communication with your partner(s) if you handle the situation smartly seems to be one benefit. We'd imagine there's something freeing about ripping your deepest desires out there for more than one person to see. Being free, living in the moment, playing out your carnal desires -- all benefits, from our point of view.

Regular thing? Triad? That depends on you and the people you're with! We could get into open relationships and polyamory, but those seem to be topics better suited for their own questions. Anyone want to ask?

However you decide to go, good luck! Be safe and by all means have fun.

"Playing with Fire" Image via TJ_Fluffy_Online

Wanna talk about sex? Need some advice? Email ask(at)chicagoist(dot)com.