Top Definition
Tailoring an asshole is a very delicate procedure where a man with a beard of great girth licks your asshole. This is a very delicate process because he must lick it like an ice cream scoop on top of a cone. His beard may touch, but only on the cheeks never getting in the way of the actual anus. Due to this delicate process a sober hobo or bum can be used, but is not recommended.

Mustaches of any kind, neck beards, goatees, and mutton chops are not suitable substitutes.
"I got my asshole tailored so good last night by some guy at the party." - White Young Female in her 20's

"Bitch, I will tailor your asshole so good tonight!" -Older Black Gentleman in his 40's
by Crusty Peas February 03, 2013
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