chilly willy Share definition Flag slang for small cock Based on how cold shrinks the penis Guy strips; girl takes one look and says, "I'm outta here, I didn't eat a roofy just to get it on with some chilly willy! chilly willy by cyberpope67,BC,Canada June 19, 2009 0 0 Get merch Get the chilly willy mug. Buy Now — $32.95 See more merch