"Trans Metamorphoses" returns us to the archaic figures that express gender variance in late medieval and early modern literature: the monstrous birth, the virgin, the hermaphrodite, and the angel. Drawing together trans theory, premodern critical race studies, and classical reception history, I construct a long genealogy of what we now call transgender, in which racial difference is inextricable from the assignment of sex. Through close readings of popular romance, early drama, Ovidian myth, and biblical epic, the project argues that literary figures inherited from classical antiquity can reveal racial and historical blind spots within trans studies now: until recently, the field has largely overlooked the premodern invention of race. Lurid portraits of unsexed infants in Syria and pallid hermaphrodites in Turkey tell a far different story. Each chapter, then, concentrates on a pair of texts that align fair skin and Christian faith with culturally specific and normative genders. I stress that expansive––and even offensive––classical terms such as “monstrous birth” and “hermaphrodite” show us the inadequacy of present critical vocabularies for gender and race. By attending to these distinctly literary depictions of gender variance, the project contests the hostile myth that trans-exclusive rhetoric is at once natural and historically sanctioned. In short, “Trans Metamorphoses” challenges the fantasy of premodern England as a place where knights were knights, ladies were ladies, and everyone was white.