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Everybody is getting confused because tip drill is used a couple ways: (1) using the tip of the penis in the crack of a woman's ass without penetration, and (2) the type of woman who who do the act - has a big ass and is a freak, but not necessarily a pretty face (see Nelly's song "Tip Drill"). It's analogous to calling someone a chicken head, except instead of performing oral, they perform ass grinding.
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