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Masochistic fantasy staging can be seen as a creation of the ego in order to compensate for a psychic structural deficit that stems from being deprived of sufficient empathetic mirroring in early childhood. It consists in the inability to establish an internal empathetic object as a stable psychic structure. Using case-studies vignettes, it is shown how as a result struggle for empathy can become the central live theme and coincide with “perverse” masochistic fantasies. After a short review of the most important traditional attempts to interpret masochism, the author delineates the communicative meaning of masochistic fantasies, which are composed of the complementary roles of the sufferer, the tormentor and the spectator. By this means the patient creates an inner scene which is apt to serve as a mirror for the experience of psychic pain and to represent the preverbal childhood trauma in a symbolic way. During analysis, this inner scene is shifted to the therapeutic relationship where different roles are kept ready for the analyst: the sadistic adversary; the unobtrusive witness of psychic pain and the role of an answering, reacting object. The relevance of these roles in therapy is examined. It is also shown how by somatisation of psychic pain the struggle toward empathy can be transferred to the stage of somatic medicine with the risk of provoking there a reaction referring solely to the body of the patient.