Excerpts from prolonged analytic work with a multiply traumatized young man who deliberated a sex-change operation are presented, highlighting some problematics in the treatment of transsexualism, a gender-identity disturbance that may become significant in recent psychoanalytic and cultural discourse on self and gender. The paper aims both to report some “technical” issues in such an analysis and to throw some light on such themes as identification, domination and submission, sadomasochism and guilt and shame, narcissistic entitlement and empowerment, desire and recognition, gender and difference, and the vertiginously multiple meanings and emotional elaborations of masculinity and femininity. The analytic itinerary is recounted with emphasis on diverse relational approaches that were attempted to fit the delicate balance of the patient's needs, his quasi-delusional transferences, and his capacity to persevere in a mutually “nightmarish,” though possible and feasible psychoanalysis.