The frequent positioning of men's sexual risk-taking as driving the HIV/AIDS epidemic in South Africa has triggered interest in men's sexual and reproductive health (SRH) perceptions, attitudes, and practices. Much research, however, presents men as a homogenous group, and focuses on the quantifiable aspects of male sexual behaviors, providing an inadequate basis for understanding men's SRH needs and addressing the gendered aspects of HIV prevention. This study used sexual history narratives to yield more nuanced and contextualized understandings of male sexuality as it relates to SRH. Fifty sexual life history individual interviews and 10 focus-group discussions (FGDs) with men, as well as 25 sexual life history interviews with women, were conducted with participants purposively sampled from three age categories: (18–24, 25–55, and 55+ years), a wide range of cultural and racial backgrounds, and in urban and rural sites across 5 provinces in South Africa. Interviews and FGDs elicited stories of participant's early knowledge of sex and sexual experimentation and then explored sexual relationships and experiences in adulthood—including engagement with HIV risks and SRH management. The data were analyzed using a thematic approach. Many male participants conformed to dominant norms of masculinity associated with a high risk of sexually transmitted infections including HIV, such as having regular unprotected sex, reluctance to test for HIV, and poor SRH-seeking behaviors. Yet, the narrative accounts reveal instances of men taking steps to protect their own SRH and that of their partners, and the complex ways in which hegemonic gender norms influence men and women's SRH. Ultimately, the study points to the value of sexual biographies for gaining a deeper understanding of male sexuality, and the social structures, meanings, and experiences that underlie it. Such insights are critical to more effectively engaging men in HIV prevention efforts.