Liberal versions of sexuality, which mark South Africa's new democracy, have had a number of highly contradictory consequences for women and men, as old notions of masculinity and male privilege have been destabilized. The transition to democracy has precipitated a crisis of masculinity. Orthodox notions of masculinity are being challenged and new versions of masculinity are emerging in their place. Some men are seeking to be part of a new social order while others are defensively clinging to more familiar routines. Drawing on in-depth interviews with young African working class men, this paper explores new masculinities in contemporary South Africa. It examines how men negotiate their manhood in a period of social turbulence and transition. Masculinity, male sexuality, and the expectations which men have of themselves, each other and women are contested and in crisis.