Much scholarship on the history of sexual science in relation to trans history has tended to focus on two related areas of sexological activity: the invention of diagnostic categories to produce fixed and stable identities, and the development of surgical and hormonal technologies to alter the physical appearance of trans bodies over the course of the 1920s and 1930s. As a result, sexual science is mainly remembered for implementing a medicalized framework that produced rigid diagnostic labels and put emphasis on the physical or somatic aspects of trans experience. This paper presents an alternative account of the relation between trans history and sexual science by focusing on a slightly earlier historical period, the decades between 1880 and 1920. At a time when surgical and hormonal interventions were not yet within immediate medical reach, understandings of what is nowadays described as trans identity emerged through sustained dialogue between scientific and literary writers who shared ideas concerning the role of Einfühlung (empathy), fantasy, dreams, the imagination and creativity in enabling an individual to experience and achieve cross-gender identification. Starting with British sexologist Havelock Ellis’s concept of ‘sexo-aesthetic inversion’ and Ellis’s exchange with modernist writer Bryher (Annie Winifred Ellerman) in the late 1910s, the paper works backwards to trace the intellectual roots of the scientific-literary framing of trans subjectivities. These include late nineteenth-century scientific studies of colour hearing, sense perception and aesthetics as well as works by literary authors like Olive Schreiner, Vernon Lee and William Sharp/Fiona Macleod to name but a few. Through its investigation of this earlier moment, the paper moves across the Victorian-Modernist divide to illuminate previously overlooked forms of exchange between literary and sexual scientific writings and to offer an alternative account of modern trans history.