The university period provides a critical developmental transition from adolescence to adulthood. During this period, young people establish patterns of behaviors and make lifestyle choices that affect their current and future health. Using the social constructionist paradigm that examines the development of masculinities as a mutual construct of individual, social, cultural, and historical context, this article explores the interactions between masculinities and sexual behaviors of young men at the University of KwaZulu-Natal, South Africa. The study used a qualitative approach and employed purposive sampling to recruit 36 young Black male students aged between 18 and 30 years. Four focus group discussions consisting of 8 to 10 participants were conducted according to the current year of study of male students. Data were transcribed, coded, and analyzed thematically. Our results show that the freedom and independence acquired from being away from home enabled students to enact their masculinities freely. Our findings further reveal that an individual has multiple masculinities which are often exerted to suit the present discourse they are in at any given point.