Green’s Dictionary of Slang

1. to lure, to entice slowly.

1675		Woman Turn’d Bully III iii: O ho, are ye there? He’s at it again to drill me off, but all this won’t do.
c.1698		B.E. Dict. Canting Crew.
1725		New Canting Dict.

2. (US) to stare.

1965

R. Gary Ski Bum 32: That guy at the bar is sure interested in your behind. Keeps drilling. In America it’s breasts, but in Europe it’s always your ass.