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Think how you look in the mirror when you are flossing your teeth - you are trying to show your teeth as much as possible to get at the plaque. This is where this term is derived from. [Originally] "invented" in the New Orleans projects and popularized by the Cash Money Brothers, namely Juvenile. This term is applied as a way of [showing off] as you are doing something [because you are] smiling with a wide grin showing all your teeth, as if you were flossing your teeth. In context: Slim be flossin' as he roll through in his new Caddy.
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