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.
"Toot that ass up mama put that dip in ya back and let me tip drill just let me tip drill" and "see now i wanna let you ride but the rubber might slide you's a tip drill girl you a tip drill".
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