Someone who is skillful and elite enough to relocate a harden member from one hole to another without the female knowing his intentions at first, then has to accept her defeat and refer to her male counterpart as drillmaster hence forth.
Susan was bragging to her friends about the way her beau was legendary in the art of surprise during their wild romp, by giving her first anal experience before she could say a word, giggly implying "After that, I had no choice but to call him drillmaster"
by Gmoose82 May 28, 2018
Get the Drillmastermug.