Green’s Dictionary of Slang

1. a gigolo.

a.1690

‘Whigland’ Harleian Mss. 6913.383: Debauch’d with filthy Lucre, this nauseous Drill Prostitutes his Honesty to all that will.

2. (US) the penis.

1916		H.N. Cary Sl. of Venery I n.p.: Drill. The penis.
1948		T. George ‘Long John Blues’ 🎵 He took out his trusty drill and he told me to open wide / He said he wouldn’t hurt me but he’d fill my hole inside.
1972		B. Rodgers Queens’ Vernacular.