Male genital self-mutilation is an infrequently reported occurrence in the medical literature. The reports describing such cases have focused mostly on surgical repair. The case reports written from a psychiatric point of view have outlined possible risk factors contributing to this behavior. Typically, reports depict cases of a single episode of self-mutilation. To date, we have found twelve cases that have addressed the specific issue of repeated episodes of genital self-mutilation. In this article, we report the case of a 49-year-old man who succeeded in castrating himself after sequential episodes of genital mutilation. We will review previous cases of repetitive male genital self-mutilation and draw comparisons between those and our patient's case to arrive at common risk factors that may alert the clinician to this type of behavior.