1) is a situation that occurs when one is drunk and wiping their own ass. Slippage of the toilet paper occurs and the end result is fecal matter on the digits of the wiper. Rumor has it that in the Middle East everyone has a bad case of Whiskey Dew Finger because they have no trees and we want all of their oil. World peace will not be achieved until Middle Eastern people realize that Whiskey Dew Finger is socially unacceptable and tp for oil is an even trade.
2) An awkward sexual situation that is the result of unapproved anal play by the fucker dominating from the doggie style position.
Matt: “Hey Rob, you want some cheetos?”
Rob: “Nah thanks, I got a bad case of Whiskey Dew Finger”