A Player and Pimp, a kid who gets all the bitches without trying. He doesn't swim in pussy He drowns in it. He is the coolest kid you'll ever meet. A Wingarnder will either be found In his 200 million dollar mansion or your local strip club. A Wingarnder is truly a pimp. A Wingardner can also be called A professor. A Proffesor in Fucking your Bitch.