This article presents an ethnographic and narrative portrait of Semonpiru, a middle-aged Bolivian Guaraní man who challenges social norms in various aspects of his life, including his sexuality and performance of masculinity. Drawing on over a decade of ethnographic research and a long-term relationship with Semonpiru, and from a reflexive positionality, the article examines non-normative masculinities, naming practices, and gender categories in everyday life among Bolivian Guaraní communities. Focusing on the local category kuña-kuña (“woman-woman”), applied to men perceived as insufficiently masculine, it shows the ways in which Guaraní gender norms shape social life and how Semonpiru’s singular subjectivity intersects with categorizations and the normative gaze of his social milieu, thus highlighting the ambivalent balance between regulating deviance and acknowledging its existence on their own terms.