rolling the cigar Share definition Flag A guy fondling himself by grabbing his cock on the outside of his pants and squeezing in a rolling manner to cause the shaft to swell and get noticed. Whore 1: "Ooo - check him out!" Whore 2: "Nice! He's rolling the cigar! Times to go gets me some!" rolling the cigar by RNPS April 13, 2008 Get the rolling the cigar mug.