Genital herpes has superseded the bacterial sexually transmitted diseases (STD) as the most prevalent STD seen worldwide, with an estimated 491 million being affected. It is encountered with an increasing frequency, with a prevalence of 11.9% in the USA, and can present in atypical and severe ulcerative forms, especially in human immunodeficiency virus (HIV)-infected individuals. Though a definitive antiviral treatment with acyclovir, valacyclovir or other derivatives exists, the property of latency and reactivation leads to its increasing incidence and prevalence. The common sites of involvement in the males are the glans, prepuce, and shaft of the penis. The male condom, if used appropriately, is the most effective among the barrier methods of contraception, with an additional advantage of protection from STDs. However, it has a failure rate of up to 13%. The efficacy of condoms in preventing herpes simplex virus 2 (HSV-2) transmission has been studied in several contexts; condoms are often associated with a decreased risk of HSV-2 transmission, yet fallacies can occur. Here, we describe a male who developed a primary episode of genital herpes at the base of the penis, despite proper usage of condoms during intercourse. This presentation can be likened to condom chancre, a much-described entity of primary syphilis.