This book presents an overview of present-day psychoanalytic thinking about the perverse spectrum: perverse thinking (disavowing reality), perverse modes of relating (manipulating others for one’s own gain at the other’s expense), and perverse character structure (toying with another’s sense of reality), culminating in a clinical exploration of the challenges associated with treating patients who manifest perverse transference reactions. Stoller’s contested theories about gender identity, sexual fantasy, and perversity constitute a model of male psychological development that contradicts Freud’s belief about the advantages of being born male. When a boy realizes his body differs from that of his mother, noted Stoller, the boy ceases to feel as close to her as he once felt, which is a calamity the boy must bear and mourn. The boy’s burgeoning sense of superiority, associated with the phallic narcissistic stage of development, helps counter the loss. Fixation at this stage is not the norm as Stoller had imagined, rather it helps account for what is colloquially referred to as “toxic masculinity.” The task of individuating from mother colors a man’s subsequent relationships with women, beginning with the boy’s efforts to break free of mother followed by a subsequent struggle against the urge to be reunited with the primal mother, which contributes to men’s dread of women. Rereading Stoller challenges present-day thinking about gender and gender identity, and it clarifies the role objectification/fetishization, sexualization, and perversity play in the lives of men—the extent male fantasy is tinged with hostility. With fascinating clinical vignettes and a deep understanding of the source material, this is key reading for psychoanalysts and psychotherapists working with men.