Masculine predatory sexual aggression, the desire to hunt and prey on feminine bodies for sexual release, infuses the erotic landscape of our cultural milieu and intrapsychic fantasies. Despite this fact, it is rarely discussed head on. Treating masculine sexual predatory aggression as a toxic substance, psychoanalytic theorizing attempts to cleanse itself of this toxin by a variety of defensive maneuvers. These include pejorative labeling, prematurely treating it as a phallic defense against vulnerability and receptivity, normalizing developmental explanations and implicit moralizing on the part of the analyst towards the patient. What often gets missed in these defensive interventions is the experience of desperation, brokenness and the feeling of being shattered and obliterated by the act of being the aggressor in penetration. A detailed case study with candid descriptions of the analyst's countertransference reveal how discomfort in the analyst towards the patient's sexual predatory desires led to impasses in the deepening of the treatment. An acknowledgment of the presence of predatory sexual aggression, including in the analyst, without defensive movements towards condemnation or moralistic theorizing can promote a more sustained engagement with the clinical work and lead to a deepening of the psychoanalytic process.