This chapter explores what it means to negotiate embodied ‘gendersex’ as part of engaging with transmedicine. It draws in the main on two trans men’s narratives about their trajectories to undertake gender-affirming surgery, with one man travelling from Denmark to Serbia and the other shifting from publicly funded trans-specific healthcare to a private hospital within Serbia. I use the concepts of navigation and negotiation to move beyond theoretical discussions about whether medical transition is transgressive or compliant, and look instead at individualized orientations regarding surgical interventions. I utilize a framework of biomedicalization to consider how these processes involve negotiating surgeries and navigating in borderlands between different (public and private) healthcare systems, and across international borders, as well as in borderlands between the capitalist logics of body modification as a commodified good, the logics of medical transition as validated within a framework of pathologization, and emerging logics of self-determination. The chapter offers insights into contemporary sites where the organization of transmedicine is changing, and where knowledge about how to chart a course through medical transition is largely created in trans people’s multi-sited networks online and offline.