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Looking to queer and trans cultural texts from DIY zines to classic queer literature to contemporary experimental cinema, this article considers how sailors represent boyhood as a trangressive embodiment that reworks masculinities and processes of representation. By locating the youthful transmasculine body as a representational norm, queer/trans films like Maggots and Men (2009) create spaces through which sailors reshape meanings assigned to maleness, boys, and men. A linked analysis of Micah Bazant’s self-published Timtum (1999) and James Baldwin’s Giovanni’s Room (1956) raises further questions about the signs and codes of sailors and postadolescent boyhood in opening up new embodiments for gender non-conforming adults. Investigating how trans sailors become icons of youthful nostalgia and queer masculinities, this paper also questions correlations between sailors and Whiteness, boyhood, colonialism, migration and race.