Three's a Crowd

by Frank Pittarese

Dear Frank,
I am a 22-year-old female who is currently single. I don't consider myself a prude, but you won't catch me on those "Real Sex" shows, if you catch my drift. I work in a mid-size office part time, and have become friends with a girl who is a few years older than me. She's much more open sexually than I am and has recently approached me to ask if I would be interested in a three-way with her boyfriend. She's done them before--she says she is not bisexual but is experimental. (I've never experimented--not with group sex and especially not with lesbian sex.)

This would be her boyfriend's first three-way and he's met me and is 'into it'. I'm the hold-out. It's not something I would initiate, but I admit I am intrigued. Her boyfriend is very good looking and she is clean and attractive. My reservations are not so much about the act, but about the 'before' and 'after.' If I do this, what precautions should I take, both physically and emotionally? I've heard there is a 'social discomfort' factor following these kinds of things. But, truth to be told, I will probably get a new job soon enough and probably lose touch with this friend. Advice?
--Three's a Crowd...Maybe

Quite Frankly:
It sounds like you're not one of those people who gets wiggy about screwing co-workers--or about casually swimming in the gay sex pool. It also sounds like you're more than halfway towards romping in the sack with this couple, so bravo to you on all counts!

Keeping that in mind, I'd say that all you really need to do beforehand is have an honest discussion with your co-worker friend about what you all expect before, during and after your three-way.

Obviously, you want to keep this situation a private one, so you need to make it clear that this experience should not be shared with other co-workers. You also might want to set up some definitive rules about what may or may not happen in bed. What do she and her boyfriend expect from you? How far are you willing to go in terms of lesbian sex? Are there things that YOU want to do that might unsettle either of them?

I doubt there will be much "social discomfort" coming your way from your co-worker, since she was bold enough invite you to bed in the first place, but you need to ask yourself if this event will pose a problem at work BEFORE you go through with it. If you don't think you can deal with the aftermath, then don't take off your skirt. If, on the other hand, you can screw the both of them and come out smiling the next day, ready to talk shop, then have at it.

Remember, they're a couple--which automatically makes you the outsider no matter how friendly they are. You still have to go home alone at night. As long as you keep your emotions out of the situation, and treat it like the hot sex that it hopefully will be, you should be able to keep things in perspective.

Oh, and physical preparation? Take a shower first. Nobody likes a stinky vagina.