This exploratory quantitative study examines past risky sexual behaviors among young men who were circumcised as part of a rite of passage to adulthood embedded within a cultural and traditional belief system in the Eastern Cape Province in South Africa. Following permission from the Eastern Cape House of Traditional Leaders (ECHOTL), individual face-to-face interviews using a structured questionnaire were conducted among 114 initiates. The mean age of the participants was 18.9 years, ranging from 15 to 32 years old. About 79.8% reported already having had sex with a woman prior to initiation. Of those, 89% reported that they ever used condoms when having sex, and 61% reported consistent use. Logistic regression analysis showed that consistent condom use increased with higher educational levels. Those involved in other risky health behaviors (specifically, smoking) were also more likely to report inconsistent condom use. Most participants had positive beliefs about male circumcision and STI/HIV transmission. This study provides a first look at the sexual behaviors of young men at the time of their initiation in adulthood, a process that is intended to make it socially acceptable to initiate sexual relations and highlights a major public health challenge in integrating the protective health benefits of circumcision with indigenous cultural practices.