This is the second of two chapters that examine ways Stein’s increasingly experimental writings during the first three decades of the twentieth century gradually work through dominant early twentieth-century genders, loosening up rigid constructs of masculinity she encountered in Otto Weininger’s misogynist Sex and Character. Chapter Three argues that her innovative writings from the 1910’s and 1920’s—such as the long poems “Lifting Belly” and “Patriarchal Poetry” (1927)—use Toklas’s feminine positioning to establish Stein’s masculinity. Whereas Stein’s earlier fiction presented more subtle challenges to Weininger, Stein’s experimental poems from the 1910’s and 1920’s explicitly and jubilantly use linguistic innovation to articulate a flexible and feminist transmasculinity.