Jill-Head Share definition Flag A skanky woman with pigtails that serve as handles when masturbating with her mouth. Hey, look at that old ditz with pigtails, I bet she gets jill-headed daily. Jill-Head by Juan Carloz August 30, 2010 0 0 Get merch Get the Jill-Head mug. Buy Now — $32.95 See more merch