This chapter highlights trans poetry’s role in shaping and challenging sexological discourses and respectability within queer and trans communities in Weimar-era Germany. During this period, concepts of gender, sexuality, heredity, and disease evolved within the burgeoning field of sexology. The poetry in the lesbian magazine Die Freundin (1924–1933) distills these ideas, engages with the slipperiness of taxonomies, and navigates the fragmented yet reifying field of sexological knowledge. The author, aligning with scholars in queer, trans, literary, and German studies, illustrates how literature, sexology, activism, and subcultures intricately intersect to shape trans identity. Focusing on three poems, this chapter examines how these interactions influence the poetic formation of trans identity. While prior scholarship often centres on short stories and sexological articles in Die Freundin, this chapter uncovers the epistemological richness of trans poetry as a medium for exploring taxonomies, communities, and respectability politics. It argues that the poetry in Die Freundin serves as a speculative space, offering nuanced perspectives on categorization and envisioning new ways of being in the world and in community with other queer and trans persons.