In recent years, a global reckoning with sexual misconduct has inspired renewed interest in understanding how men and boys succumb to toxic sexual cultures. In South Africa, the setting for this study, concern has been raised about young heterosexual masculinities predicated upon sexual coercion and misogyny, which increase girls’ vulnerability to sexual risk. This paper seeks to understand how a group of teenage working class boys accommodate ‘hegemonic’ constructions of masculinity, and how particular performances of heterosexuality consolidate a culture of misogyny in the schooling environment.South African scholarship 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, this paper draws on focus group discussions with ‘coloured’ teenage boys (aged 15–19) in a Durban township, and examine their understandings of heterosexual relationships. The study draws from a larger qualitative research project titled ‘Stop the Violence’ examining through close-up interview methods enabling young people’s own perspectives of gender, sexuality and inequalities. The data suggest 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. I argue that, in a context of socioeconomic marginalisation, underpinned by the legacies of apartheid, race and class inequalities continue to emasculate men and boys.A culture of predatory and otherwise troubling heterosexuality is evinced by narratives of sexual assault, unsafe sex, and pejorative language describing women and girls.Heterosexual performances offer ways for perceived male weakness to be mediated through power expressed within oppressive gendered cultures—and this underscores the need to address young masculinities in schooling- which is a key focus of this , gender equality and schooling. As the call for bringing boys and men as partners in ending gender inequalities is increasing in much of Africa, the paper ends with some implications for how schools can enable a feminist consciousness and gender justice which are key principles of South Africa’s democracy.