In the first two chapters of this book, I explore the figures of male characters who dress as and pass for women in terms of their effect on a sex/ gender system and their place in the patriarchal marriage economy. In this chapter and the next, I turn to perhaps the most charged aspect of representing male-to-female (MTF) crossdressers: how desire, sexuality, and sex are represented in the queer context of crossdressing. While the MTF crossdressers I discuss here are still very much in relationship with large-scale systems of power, these chapters turn to a more intimate kind of relationship, a queer dyad. Judith Butler describes the imbrication of gender and desire: “Although being a certain gender does not imply that one will desire a certain way, there is nevertheless a desire that is constitutive of gender itself and, as a result, no quick or easy way to separate the life of gender from the life of desire.”1 While crossdressed, MTF characters become subjects of the erotic gaze from both men and women and participate in sexual encounters that are technically heterosexual/opposite sex (between a man and a woman), visually homosexual/same sex (between two seeming women), and undeniably queer and grounded in a queer heterosexuality. Moments of desire and sexual encounters in early modern texts representing MTF crossdressing offer a unique opportunity to explore the overlap and interplay of sex, gender, and desire in the early modern imagination. In this chapter, I address this issue through the idea of “queer heterosexuality” in instances of romantic and sexual contact between a MTF crossdressed characters and their lovers; in Chapter 4, I address it through a discussion of “gender labor,” wherein romantic partners co-create their MTF crossdressed lover’s gender.