This essay on the American literary history of trans before the inception of modern transness examines such practices and their critiques prior to modern technologies and taxonomies of trans subjecthood. By reading slave narratives, poetry, short fiction, and other genres from the eighteenth through the twentieth centuries, the chapter unravels the preoccupation with individual figures as trans or otherwise gender diverse in order to highlight how the uneven processes of colonial biopolitics attempt to discipline the messiness of lived collective expressions and embodied experiences. By foregrounding works on transing and gendering by Black, Indigenous, Latinx, and Asian writers alongside writings better known about white gender nonconformity, this chapter unsettles the racial innocence of transness and triumphalist claims about gender variance as universal. Through attending to structures that produce embodied legibility and practices of meaning-making, the aim is to orient readers to historically informed and theoretically nuanced ways of reading American literature before the twentieth century against tendencies to approach transness through the overrepresentation of whiteness.