pussywinkle Share definition Flag A person who is homosexual and afraid of everything. Dude, stop being such a pussywinkle. You're gonna have to skydive eventually, and the ass-pounding thing has got to stop. pussywinkle by jenou April 19, 2007 0 0 Get merch Get the pussywinkle mug. Buy Now — $32.95 See more merch