This article draws on queer psychoanalysis to explore links between homoerotic masculinity and heterosexual women under patriarchal manhood. I argue specifically that the genderqueer effects of male masochism—as conceptualized by Carol J. Clover—helps us to understand Sherwood Anderson’s exploration of a male protagonist who identifies with women’s pain so profoundly that he himself transforms into a woman who then experiences what it means to be subjected to male violence and sexual predation from that position. Anderson feels ambivalent about the extent to which this form of genderqueer masculinity is sustainable. It is a position that must be purged for the protagonist to survive, but it is also an experience that stays with him. The analysis then broadens to address the larger implications of the close reading, specifically what it means for a cisgender, heterosexual male author to depict men who see themselves in/as women.
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