Transgender subjectivities are becoming an increasingly popular area of inquiry for relational psychoanalysis. Postmodern feminist analysts, perhaps especially, grapple with the seemingly contradictory position that the trans subject embraces both binary and multiple, both essentialist and constructivist, modes of being sexed and gendered. Using a composite clinical example, this paper explores some of the dynamics between a transmale psychoanalytic psychotherapist and his transmale patients. Through a close-up lens on the trans–trans analytic dyad, and with an emphasis on metaphors and experiences of the body in both flesh and fantasy, this paper illustrates a model of transmasculine subjectivity in which the language of material substance carries interpretive power. It is suggested that a post-postmodern theory of gender and sex is needed to fully articulate transgender subjectivities.