This chapter interrogates William Burroughs’ construction of queer masculinity across his life and work, tracing how trauma, sexual repression, and homophobic cultural conditioning shaped his macho queer persona and his artistic output. Ian MacFadyen analyzes The Wild Boys and Port of Saints as exuberant departures from earlier narratives of abjection, projecting a militant, erotic utopia of all-boy societies free from female influence. Through Burroughs’ letters, routines, and cut-up techniques, the chapter tracks the evolution of a self-sustaining erotic textual system – simultaneously revealing and concealing the vulnerability that underpinned his hostility and misogyny. MacFadyen contrasts Burroughs’ rejection of effeminacy with his fascination for sexual fluidity, exploring the cultural contradictions of queer identity in the mid twentieth century. Through close readings, the chapter considers Burroughs’ boy fantasies as both a symptom of and response to social trauma, while critically assessing his lasting legacy – and limitations – as a radical figure of queer cultural disruption.