pop a cherry Share definition Flag When a virgin has sex for the first time and she bleeds when the guy pops her cherry. ALOT!!!!! "Gotta safe full of cherries cause I pop it and lock it.""Pop a cherry mofo!" pop a cherry by German sparkle party November 23, 2013 0 0 Get merch Get the pop a cherry mug. Buy Now — $32.95 See more merch