Wooly bobos Share definition Flag Slang term for testicles. More than likely it is an unshaven, unkempt, not manscaped pair of testicles. Hence the wooly. In the summer I need to be careful prior to sitting. Don't want to accidently crush my wooly bobos. Wooly bobos by M_Dubz152 June 9, 2023 0 0 Get merch Get the Wooly bobos mug. Buy Now — $32.95 See more merch