We present a case of an 81-year-old man who presented with a large recto-urethral fistula resulting in prolapsing bladder through the anus. A multi-disciplinary approach with urology, colorectal surgery and plastic surgery was utilized for management of the prolapse with excellent postoperative result. This unique scenario enabled a transanal cystoprostatectomy; the procedure was completed using a natural orifice without transabdominal surgery.