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Anal orifice, esp. that of an attractive female.
After Mike played three consecutive John Mayer CD's, Ashley finally opened up her chocolate box to him.
by Psychobenzaprine August 15, 2007
a five-some with four black men and one white woman in the middle.
"did you hear that isabelle got chocolate boxed last night?!"
"yeah, she sure has a bad case of jungle fever."
by dabes May 07, 2012
A person (male or female) who is not only good-looking, but charming as well.
Girl #1: Did I tell you that Billy left a surprise in my locker?
Girl #2: No, what was it?
Girl #1: A red rose.
Girl #2: No way! That's so sweet!
Girl #1: I know, he's a real chocolate box.
by chocolate box April 20, 2006