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Castration anxiety is a contentious issue for contemporary psychoanalysis and necessarily occupies a central position in the theory that Freud developed, at the crossroad between the individual and his desires, the individual and his sexuality, and the individual and civilization. In this wider sense, castration anxiety describes a state of mind in which individuals, women as well as men, must battle throughout the course of their lives against limitations and, hence, so-called safe pleasures (security, reproduction, family, etc.) brought about through the constraints imposed on them by civilization. From this perspective, castration anxiety can be seen as a primary gesture toward a sexuality that becomes enmeshed in conflict and obscured by a sense of shame and guilt. Exploring the works of contemporary British artist Sarah Lucas, the Italian writer A. Moravia, and the Italian director M. Ferreri, followed by a series of brief clinical vignettes, I underline and discuss the oppositional and unfulfillable search for lust encapsulated in Freud’s castration anxiety concept and the eternal mysteriousness of sexuality.