A term originating in the Chicago metropolitan area describing a particular style of semen facial where the man lovingly and perfectly bisects his partner's face with his ejaculate as to avoid said partner's eyes. A Chicago Ending typically describes the man's intent rather than deed, as it is difficult to execute a perfect Chicago Ending in practice.
OMG, Andy took me out to dinner in Chicago last night, and later gave the me the best Chicago Ending. It was so sweet and fitting.
by Gans November 30, 2012