Dick Trail Share definition Flag Typically when an individual has sex with his friend's passed hookups in the order they hooked up. Bro you slept with the last 3 chicks I banged all in the same order. Quit Dick Trailing me. Dick Trail by Shitdefiner911 May 31, 2017 0 0 Get merch Get the Dick Trail mug. Buy Now — $32.95 See more merch