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1.
When you hook up with multiple girls in one night (not necessarily at the same time but can be at the same time), thus making them gain swag and making you an epic pimp.
Person 1: "So you're going to hook up with Sarah and Rachel tonight?"

Person 2: "I'm not just going to hook up with them, I'm gonna Bag Em' and Swag Em'"
by Bag Em' and Swag Em' June 07, 2011