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Benefiting from unprecedented media attention and academic interest, the situation of trans people is raising questions. The contribution of gender studies and human sciences to psychoanalysis has led some authors and practitioners to rethink subjection and subjectivation through gender, particularly with regard to gender transitions. Without claiming to exhaust the topic, this article aims at contributing to a psychoanalytical framing of gender and sex transitions by looking at how the real is interwoven with the symbolic and the imaginary. To this end, we first return to some defining elements of transitions. We then examine Judith Butler’s rereading of Lacanian psychoanalytic theory. This rereading allows us, on the one hand, to consider subjects’ psychic constitution in relation to their social context and, on the other hand, to promote the subversive force of the imaginary in the face of the symbolic. Finally, we investigate the instance of the real, defined as that which eludes symbolization. Approached by way of the real, trans situations are thus reinscribed in the dynamic of invention of subjects struggling with their jouissance.