This chapter provides a discussion of the anxieties within (conventionally cisgendered) communities faced with the complex realities of transgender identities, sexual binarism and dysphoria. Ancient discourse tended to reduce this to a simple binary according to which conventional constructions of cisgendered bodies contrasted with a single representation of anomaly: the hermaphrodite. The story of Hermaphroditos, however, reveals that sexual hybridity and ethnic categorization (Karians and Greeks) operated in tandem and recursively: one group’s culture hero (as founder of marriage) become another’s intersex monstrosity. Hermaphroditos is only one example of a body undergoing sexual transformation, and other figures, such as Teiresias, Kaineus and even cross-dressing Achilles, illustrate that there existed a space for imagining alternatives to conventional categories. But an imaginative space is not a manifesto, and sexual anomaly (as it appears in ancient thinking) illustrates a trajectory of Greek culture: hybrids and anomalous bodies become partly decorative and, in literary works, interesting paradoxes, while their power to shock was largely relegated to the sphere of magic.