In this paper the author endeavors to describe one aspect of the treatment of a male patient who has been in analysis for eight years, four-times-weekly. The patient's presenting symptom, intrusive egodystonic pedophilic fantasies, seemed initially to be the product of an obsessive neurosis organized around unconscious oedipal phantasies. The first period of analysis revealed that the conscious pedophilic fantasies were a reversed version of the mother's eroticised seduction of her son, in the absence of a substantial enough father figure to separate him from her. However, as is sometimes the case, a few years of analysis and the deepening of the transference, unveiled an entirely different configuration. Underlying the obsessive neurosis was a deeply-entrenched perverse moral masochistic functioning that was rooted in an archaic identification with a mother who operated essentially from a dramatically victimized position. This expressed itself vehemently in the transference. As the moral masochism unfolded in the treatment, with its cohort of forceful projections of sadism and guilt onto the analyst, it brought about arduous countertransferential challenges and the frequent destabilization of the author's analytic identity. Reflection on the countertranference and self-analysis allowed the author to listen to the chronic sadomasochistic dynamic from another perspective and begin to perceive the depth of helplessness behind it. To illustrate this process, we will present the initial interviews, a summary of the treatment, and some sessions dealing specifically with the topic of this paper.