A 32-year-old male presented with a history of urinary retention and difficult catheterization. An antegrade urethrography revealed multiple strictures in the bulbous and membranous urethra as well as diverticulations in the bladder wall. He was diagnosed with gonococcal urethritis likely caused by Neisseria gonorrhoeae due to his history of multiple sexual partners. Complications of gonorrhea can include urethral strictures, prostatitis, and infertility.