Connell’s concept of hegemonic masculinities has been invaluable for prevention efforts that seek to promote a shift in hegemonic male norms driving the HIV epidemic. However, inadequate attention has been given to the internal processes of hegemony, which limits the comprehension of how to engage men in HIV prevention efforts. A narrative approach, which privileges the diversity in men’s lived experiences, could address such concerns. Fifty sexual history interviews were conducted with men sampled from three age categories: (eighteen to twenty-four, twenty-five to fifty-four and fifty-five plus), a range of cultural and racial backgrounds, and in urban and rural sites across five provinces in South Africa. For the purpose of this article, narrative analysis was conducted on three cases that provide a platform for understanding how men both conform to and resist gender norms that influence their sexual and reproductive health. Implications of the narratives for gender transformative HIV prevention efforts are discussed.