In contemporary cultural life, the visibility of transsexuality is part of a larger cultural revolution reorienting the nature of identity, sociality and modes of selffashioning. The therapeutic clinic, however, lags behind: transsexuality is still considered a pathological condition. Historically, psychoanalysis has approached the experience of transsexuality through questions of “gender certainty” and “sexual difference”, often invoked as separating the boundaries between normalcy and pathology. Contemporary theories of gender (e.g. Benjamin, 1998; Dimen, 2003; Harris, 2005) attempt to de-pathologize transsexuality, although these theories often treat gender categories as sociological descriptors. Even when masculinity and femininity are approached as psychic positions (e.g. Gherovici, 2010), discussions are often limited to “the transsexual individual”. Missing is a conceptualization of transsexuality as a psychical position and discussions on how its subject formation affects the imaginary of psychoanalysis. In this book, I attempt to broaden our conception of transsexuality, shifting the focus from the “transsexual patient” to the analyst’s thought processes. I do so by considering questions of desire, sexuality and sexual difference.