Who is the most inappropriate person you've slept with?

Your mom.

fricked my future (at the time) brother in law's sister after the rehearsal dinner. She was a red head and an absolute freak. Still don't let him live it down.

I saw you're full of shite.

A friend of a friend's NOT QUITE ex-girlfriend while she was still living with him. She made it sound like they were broken up, but it quickly became apparent that that was not entirely accurate. Then, I ended it.

quote:

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This thread is going to be very, very long.

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unlike the sexual encounters themselves

Sick burn. You know what I meant.

co-workers sister

Close to what I did. I got with a friend of a friend's ex gf just a couple of days after they broke up. It was theorized at the time that she just wanted to make him jealous but I found out later that she never told him and she just always dug me. I would have never guessed. She kinda seemed out of my league to me. Oh well.

Mine would be my wife's best friend in college, but that was a couple of years before I met my wife. About choked on my beer when my wife introduced us.

The best one would be my buddy who has slept with both of his sister in laws (his wife's sister and his brothers wife), but this was before he met his wife or his brother started dating his wife. Needless to say he probably has some awkward family get together's.