Sexually transmitted infection testing rates among young men remain low, and their disengagement from sexual health services has been linked to enactments of masculinity that prohibit or truncate discussions of sexual health. Understanding how men align with multiple masculinities is therefore important for tailoring interventions that appropriately respond to their needs. We draw on 32 in-depth interviews with 15–24-year-old men to explore the discourses that facilitate or shut down sexual health communication with peers and sex partners. We employ a critical discourse analysis to explore how men’s conversations about sexual health are constituted by masculine hierarchies (such as the ways in which masculinities influence men’s ability to construct or challenge and contest dominant discourses about sexual health). Men’s conversations about sexual health focused primarily around their sexual encounters – something frequently referred to as ‘guy talk’. Also described were situations whereby participants employed a discourse of ‘manning up’ to (i) exert power over others with disregard for potential repercussions and (ii) deploy power to affirm and reify their own hyper-masculine identities, while using their personal (masculine) power to help others (who are subordinate in the social ordering of men). By better understanding how masculine discourses are employed by men, their sexual health needs can be advanced.