A young woman who came for treatment of anxiety and depression is presented in a detailed case report. She developed an erotized transference that was predominantly sadomasochistic and included her intention to torture and castrate the analyst. The author demonstrates how the analyst's behavior, including countertransference contributions, assisted in shaping the vicissitudes of sadomasochistic transference paradigms. A collusion was established between patient and analyst in a manner that enabled the analytic dyad to work productively toward an eventual resolution of the patient's conflicts. The author discusses the case's complexities pertaining to enactments, while emphasizing the importance of carefully monitoring and addressing countertransference experiences that mold and shape such a collusion.