Trouser Willy Share definition Flag A penis created by your trousers when you sit down and your flies roll up. Not actually a penis. "Wooaaahhh, look at how big my trouser willy is!" "Phwoar." Trouser Willy by Joelle M May 21, 2008 0 0 Get merch Get the Trouser Willy mug. Buy Now — $32.95 See more merch