A boy page is in love with his master. One version of this story should be familiar: shipwrecked in a strange land, Viola cross-dresses as the eunuch page boy “Cesario” so that she might serve Lord Orsino, who enlists her to woo Lady Olivia. Matters are complicated when Cesario falls in love with Orsino and Olivia with Cesario, but all plan to be married to appropriate heterosexual partners in the end.1 The story is retold less than a decade later in Francis Beaumont and John Fletcher’s Philaster; or, Love Lies A-Bleeding (1608–1610).2 Inspired by Viola’s escapades, this play features the boy page Bellario, whose master, Philaster, employs him to convey romantic messages to his fiancée, Arethusa. Bellario is besotted with his master and at the end of the play is revealed (to both characters and audience) as the girl Euphrasia.3 A few years later, in The Honest Man’s Fortune, the boy page Veramour delivers messages from his master, Lord Montague, to the Lady Lamira.4 Veramour adores his master and is suspected to be a girl in disguise who has been inspired by “two or three Plays” to dress as a boy (5.1, sig. Xxx2r). Eventually Veramour’s clothing is searched and he is declared to have been a boy all along. Each page presents a challenge to conventional scholarly understandings of the relationship between gender and embodiment in early modern culture. This article presents a critical reassessment of the cross-dressed page through the lens of transgender theory, focusing on its evolution through Viola, Bellario, and Veramour. It challenges the supposed “real” material body of the boy actor; it analyzes the importance of class, age, and imitation to transmasculinity; and it investigates the violences to which gender-divergent characters are subject, arguing for reading modern and early modern gender divergence comparatively. Drawing on trans theory, this article discusses the “real” and its relationship to deception, how imitation constitutes gender, the prosthetic materiality of gender, and the role of narrativization in constructing gender. Finally, in identifying gender divergence in characters who are never outed, it seeks to define early trans identities beyond violence and exposure.