New medical advances and options for transitioning along with an array of gender representations have provided gender diverse children and adolescents liberating possibilities. The transitioning youth's demands for recognition and/or support for initiation of medical intervention pushes against the analyst's theories of gender and challenges conservative understanding of sexual identity, moving it closer to the multidetermined nature of dreamwork. In this article, the author traces recurrent metaphors in discussions about gender transitioning with a focus on selected articles recently published in the International Journal of Psychoanalysis, particularly an essay authored by David Bell (2020) entitled “First Do No Harm.” The author focuses on three images—contagion, the naturality of gender, and amputation—to ask, what do these apparently disparate signifiers reveal about the anxieties in the field?