When thinking of the intrigue of the sexual body in the last century, two literary characters and two different solutions to the question “am I a boy or a girl?” come to mind: Foucault’s (1980) Herculine Barbin and Eugenides’ character Calliope (“Cal”) from the novel Middlesex (2002). We know of Herculine through Michel Foucault’s publishing of her diary in 1980. She was a hermaphrodite living in France from 1830 to 1860, attending an all-girls school who committed suicide at the age of 30. Living in different times and contexts, Calliope’s and Herculine’s complex theories of origin and becoming represent two different ways of constructing gender and the phantasized Other. Both provide the possibility of writing the sexual body, both capture the phantasies of intersex and transsexuality circulating then and now in the public imaginary, and both of their narratives touch upon a collapse of meaning, forms of madness and notions of transformation. And yet, the narrative of their gender embodiment is strikingly different.