In this paper we focus on South American trans* masculine existence. First, we recuperate historical subjects who are often read by historians through a cissexist framework as examples of “strategic transvestism”. We attend to these subjects’ narratives, histories, and first-person accounts, suggesting that, rather than examples of strategic transvestism, these subjects are of interest to a broader trans* masculine archive. Second, we highlight the narratives, practices, and experiences of individuals who transitioned during or soon after the region’s dictatorial period in the twentieth century. In doing so, we suggest differences in the conditions of possibility for the emergence of trans* masculine communities and subjectivities, in departure from the contouring force of Anglo-centric histories. Finally, we underscore the work of South American trans* masculine activists from the 1990s to the present, calling attention to their contributions on a local and global scale.