Bupivacaine is a local anesthetic that is known for its long duration of action of up to 7 hours. Following its introduction in 1965, reports emerged of the drug’s central nervous system and cardiovascular toxicity. Moreover, when injected intravenously, bupivacaine becomes several times more toxic than lidocaine. The medical literature has well documented the practice of injecting various substances into the external genitalia for purposes of augmentation, treatment of impotence, and drug abuse. The Internet describes scrotal injections with saline and other substances for similar purposes. Such practices can lead to local tissue damage as well as death if substances enter the vascular system. The case under examination in this article involved the accidental death of a 54-year-old male who had injected bupivacaine into his external genitalia. When he was discovered by his wife, he was already dead and pornographic materials were surrounding the victim. Also located in the vicinity of the victim were syringes, Lidocaine cream, Xylocaine jelly, and three empty bottles of bupivacaine. Acute and chronic injection sites were observed on the external genitalia and contusions, scarring, focal necrosis, and calcification was discovered upon autopsy. Toxicology analysis indicated femoral blood bupivacaine concentrations of 3.8 mg/L, heart blood bupivacaine concentrations of 2.8 mg/L, vitreous bupivacaine concentrations of 1.3 mg/L, and urine bupivacaine concentrations of 11.4 mg/L. Cause of death was attributed to bupivacaine intoxication. This case serves as an indicator to the forensic and medical communities that practices of injecting various substances into the external genitalia can be fatal. Figures, references