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Southside Monday

A.(originating in Chicago, A sexual maneuver in which a male ejaculates into a females hair, making her resemble “Southpaw” the Chicago White Sox beloved mascot.

B.) It's where you go to the Southside and ghost ride the whip in the Comiskey Parking Lot while the tailgaters watch
I gave Jessica a SouthSide Monday yesterday. She was so mad.
by Zigmas Maloni May 9, 2022
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