Sissy Chrissy Share definition Flag A cute gay boy. Often wears pink polo shorts and yellow or pink pants. Often not very smart or athletic, hence, "sissy" Hey! Look! That Sissy Chrissy had to stop playing basketball because his nipples itch! Sissy Chrissy by The C School September 29, 2005 0 0 Get merch Get the Sissy Chrissy mug. Buy Now — $32.95 See more merch