This study traces the influence which the medical model of homosexuality, conceived and formulated largely by German physicians, exerted upon works of prose fiction and dramas written between the late 1880s and 1914. This Third Sex, as it was named, inhabited a space created between the heterosexual male and female, and its members rapidly proliferated in literary works. Combining historical, narrative and feminist approaches, the author analyzes over three dozen works in terms of both their social contexts and the aesthetic strategies they employ in presenting homosexual characters. The writers studied include: Frank Wedekind, Elizabeth Dauthendey, Robert Musil, Maria Janitschek, Thomas Mann and John Henry Mackay. Jones’ readings of these texts reveal that these depictions evolved from a rather exact mirroring of the medical model for homosexuality into a more varied presentation in which we find the genesis of a specifically German literary discourse on homosexualities.