Sleeping Cindy Share definition Flag It is when you are in a hotel room and have sex with your girlfriend while her mom sleeps in the bed right next to you. Johnny is the only kid I know that has enough balls to pull the Sleeping Cindy. Sleeping Cindy by DeputyDean March 8, 2008 0 0 Get merch Get the Sleeping Cindy mug. Buy Now — $32.95 See more merch