The author of this article proposes to shift the focus usually placed on the conflict of patients toward the subjectivity of the clinician. He thus questions his identity as a metapsychologically oriented psychotherapist and his counter-transferential challenges in working with transgender adults in an institutional setting. By narrating the vicissitudes of the psychoanalytical psychotherapy of David, a composite case stemming from the treatment of several individuals with atypical gender identifications, the author describes the various means of clinical metareflection that he considered in order to adjust his stance, which was systematically compromised by the patient’s issues as well as his own prejudices and unconscious reactions. He further describes how the contemporary context of trans identities shaped by activism and political correctness is likely to hamper the analytical vocation to explore the unconscious, which is intrinsically a-normative and politically incorrect.