Drawing upon a post-structural ethnography of boys' constructions of gendered and sexual identities in one South African high school, this paper empirically seeks to theorise how 20 Grade 8 boys, identified as The Jokers, The Achievers, The Outcasts and The Average Ou's, simultaneously seek out spaces in male peer culture to cultivate, police and challenge hegemonic notions of masculinity. The paper illustrates the construction and positioning of masculinities across spaces of conflict, more particularly, the personal and social resources reproduced by boys in the pursuit of "desirable" masculinities across experiences of interpersonal conflict, punishment, friendship and play. Given the nature of these identity struggles in school boy peer culture, this paper highlights the need for fostering and maintaining peer conversational spaces where boys and girls are challenged to actively deconstruct prevailing gendered identities and work towards more expansive definitions of self.