Bleeding as the result of a leech in the male urethra is very rare. We describe a 13-year-old boy who had a leech in his urethra. In the emergency department he persistently squeezed his penis in an attempt to prevent the leech from going deeper into his urethra. Manual removal by forcep failed and cystoscopic removal was recommended. Penile block with lidocaine 1% relieved the pain and enabled him to squeeze his penis harder until the leech was pushed out making forcep removal easier. Post-removal he had hematuria and penile pain for 2 days. A description of his presentation and management, along with a review of the literature is presented.