Tits and Ask: The Delicate Art of Balancing Two Lovers

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How can a woman have sex with two different guys on regular basis and not have it totally confuse her heart and head?

KEN SAYS: I can’t tell from your email whether you’re a woman desperately trying to balance two lovers, or a guy slowly falling to pieces from being the side piece. If you’re the woman in question, I have to commend you, since I have a hard enough time trying to hold one lover’s interest. And even that gets tough once they realize my roommates aren’t really Michael Buble and Branford Marsalis, as I’d claimed back at the bar, and that the “after hours jam session” I invited them to was really just a veiled reference to me helicoptering my cock and balls.

That said, in those rare, all-too-fleeting periods of my life when I was actually seeing two women simultaneously, there was usually solid reasoning behind it. For example, in grad school, I dated Amy, who was sexually conservative but had a sense of humor that dovetailed nicely with my own. We laughed a lot, and it felt really, really good.

At the same time, I was also seeing Jennifer, whose conversation barely strayed past the latest “Gilmore Girls,” but whose way of saying “hi” involved greeting me at her apartment door, throwing me down on the hardwood and sitting on my face until my jaw seized.

Both women were great, and each brought unique attributes to the table that the other one, for better or for worse, lacked. In my mind, it was a great arrangement. At least until that fateful day that Amy stopped by unexpectedly while Jen was riding my face like a jockey coming into the home stretch of the Kentucky Derby. Needless to say I spent the next day contemplating my misdeeds while a surgeon carefully extracted a size 5 Jimmy Choo from my colon.

The fact that you’ve asked this question means you’re ready for a little soul searching of your own. Are you feeling slightly guilty about having two lovers (assuming you haven’t already set down some awesome polyamorous arrangement that everybody’s cool with)? Are you mentally exhausted from trying to remember whose name you’re supposed to be yelling out when a tongue snakes up your south 40? Are you, like me, drawn to individual traits that each lover has that you can’t seem to live without? if so, you may be doing yourself a favor by eventually choosing one or the other, or opting for bachelor number three, who you haven’t even met yet.

All I know is this: settling down means forever (at least for some people). If you can keep your cool while spinning two plates in the air (which, of course, is French for “screwing two guys at once”), why the fuck not?

ARIEL SAYS: To be frank my dear, I’m not sure that your dilemma is necessarily gender-specific. I believe there are also many men who, when faced with the actual logistical nightmare of multiple partners, may regret that they’ve attempted to recreate Skinamax in their normal, dull, tax-paying, Trader Joe’s-shopping lives. So I gather from your query that you have two Toms (with two dicks) and it is totally confusing your heart and your head. Methinks you are trying to be all the rom-comz, re-enacting “Love Actually” but screwing up the English accent so you sound vaguely Norwegian, and be the BEST SEXXXXIEST GIRLFRIEND EVER. But wait, WHICH Tom did you tell about your fifth grade trauma involving a Sit ‘n’ Spin?!?

It doesn’t have to be so confusing and traumatic. Are you being safe, i.e., using protection? Are all parties involved well aware that they are not the only ones invited to said party? Any there other parties that would be hurt or devastated by this part–i.e., wife, girlfriend, children, pets? (Pets can be pretty damn possessive. Ever try to compete with a ferret?)

If the answers are no, I say pass “Go” and collect $200 in sexxxy dollas. (NO, I NEVER SAID YOU WERE A HOOKER!!! I WAS JUST TRYING TO BE FUNNY!!! OH GAWWWD…)

My girl, there’s nothing wrong with enjoying the company of two men. This is indeed a time to be selfish; think of yourself as the sexual 1% while we 99-ers sit at the Jack in the Box drive-thru and pretend the cashier was really turned on by our pajamas. If you are not getting the ultimate enjoyment and satisfaction, if it is causing you more headaches and anxiety rather than 2 orgasms for the price of one, you are free to break up with either or both of them.

Because that’s what Living Single is all about. Right, Synclaire?

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