Pole Sister Share definition Flag Pole SisterTwo prostitutes who have had sex with the same man in a short period of time. Candy, you had sex with Big John the last night, that makes you my pole sister as I just did him on Monday Morning. Pole Sister by Cristy Cupps November 25, 2009 0 0 Get merch Get the Pole Sister mug. Buy Now — $32.95 See more merch