The discovery of historical genders and sexualities offers the possibility of establishing continuities between the past and present that allow for identification and a more nuanced understanding of contemporary categories. Sexually, femininity was defined by the passive position in heterosexual intercourse, and yet, one of the principal medieval associations with femininity was sexual voracity. The survey of genders and sexualities discussed in this chapter is organized around a few configurations found in medieval literary texts. Beginning in the twelfth century, the literature of romance initiated a new model of heroic masculinity in tandem with the invention of heterosexual courtly love. Same-sex desire in the Middle Ages appears most often in the context of friendship. Virginity provided a kind of gender transitivity for women in a way that it did not for male saints. Finally, the chapter addresses literary representations of gender transgression and sexual acts between members of the same sex.