We present three male patients who had a rare presentation of anal fistula reaching the genital tract. Patient 1: a 44-year-old diabetic man presented initially to urology clinic complaining of penile and scrotal masses increasing in size for 6 months. Patient 2: a 67-year-old diabetic man presented with chronic sinus discharge from the scrotum. Patient 3: a 37-year-old diabetic man who presented with chronic sinus draining pus-like material from the scrotum for 1 year. Patients 1 and 2: following diagnosis of perianal fistula by MRI fistulography, complete excision of the fistula was done. This required tracking the fistula surgically, a perineal midline incision to release the fistula and excision of the fistula opening in the anal canal. The patients were doing well postoperative and no recurrence of fistula at 1-year follow-up. Patient 3: he refused surgical intervention. Penile mass or scrotal discharge has not been reported to be caused by fistula-in-ano.