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A tip drill is another name for runnin a train on a girl. Comes from baseketball where players line up at the free throw line and tip it [off the backboard] consecutively, one after another. [Think of it] in the sense of a group of men runnin a train on a woman. First man in line hits, next man follows until everyone has had a turn... If the nelly song is [the first time] u have heard this term try listening to the lyrics more carefully. Just cause they say " it must be your ass cause its not your face" doesnt mean a tip drill is a chick with a big botty and an ugly face.
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