What is Check That Box?
1.
Implying that there is a list of boxes that can be checked in life, indicating the various experiences one has had, and checking off one of them. Almost exclusively in reference to sexual experiences. One's sexual resume. Various skin colors, sexual orientations, and physical features are all examples of boxes that can be checked off one's list.
I don't know if I'd do her (the shaved bald, heavily pierced, 200 lb woman across the way), but if you want to check that box, go right ahead.
Man, I'd really like to check that box (referring to the slim Asian hottie friend-of-a-friend).
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1.
A sexual maneuver in which the the girl is on top, facing the man, who is on his back. As she is riding him, a friend comes from behind ..
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"Enchilladitos, make you wanna' eat 'em"
"Enchilladitos, they make you want to eat o'"
were eating ..