pinky cheater Share definition Flag A pinky cheater is a latex sheath worn over a finger while being employed in a vaginal or rectal examination. My proctologist uses a pinky cheater for sanitary reasons, but she’s still a bum doctor. pinky cheater by Cranberry Bob July 9, 2021 0 0 Get merch Get the pinky cheater mug. Buy Now — $32.95 See more merch