What is Jockstrap Award?
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The term 'jockstrap award' is sometimes used as slang in the same way 'coattails' is used, i.e., to imply that someone has achieved success simply by being with someone else with more talent. A jockstrap award (or jockstrap medal) is 'given' (usually tongue-in-cheek) to someone who has achieved success by being at the right place at the right time, not necessarily through their own talents.
Members of the Chicago Bulls got jockstrap awards when Michael Jordan led them to their championships.
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Similar to the Cleavland Steamer. The act of laying a fat shit on a bitches chest.
One time I was fucking this bitch and she was like...