Attempting to masturbate as many times as physically possible before your dick falls off, during the time between fall and spring semester.
Guy 1: "Just finished my last final!"
Guy 2: "Let The Winter Break Challenge BEGIN!"
Guy 1: "Already jerked one out on the way over."
Guy 2: "Let The Winter Break Challenge BEGIN!"
Guy 1: "Already jerked one out on the way over."
by otterpark May 15, 2014
Get the The Winter Break Challengemug.