Literature on masculinities in South Africa lacks in situ examinations of how teenage boys draw upon heterosexuality as a key resource to make sense of identities. Beyond recognition that heterosexual masculinity is key to understanding male culpability in the triple challenge of HIV, gender inequalities, and violence, there is a lack of attention to race- and class-based realities in the production of young masculinities. To address this gap, we draw on focus group discussions with coloured teenage boys (aged 15-19) in a Durban township, and examine their understandings of heterosexual relationships. The data suggests that heterosexuality was a compelling force informed by dominant expectations of how to be a 'real' man. Indeed, relationships with girls were frames for ratcheting up 'compelling heterosexuality' and risky hypersexual performances based on misogyny, the subordination of women and girls, and male sexual entitlement. We argue that, in a context of socioeconomic marginalisation, underpinned by the legacies of apartheid, race and class inequalities continue to emasculate men and boys. Heterosexual performances offer ways for perceived male weakness to be mediated through power expressed within oppressive gendered cultures.