This chapter frames Caster Semenya’s two decades struggle against the International Association of Athletics Federations’ (IAAF) definition of femininity within the long history of Black women being denied femininity and womanhood within the White imagination. In sports, women like Sharapova and Kournakova are represented as athletic, but also “girly” and sexual, whereas Black athletes like the Williams sisters are constructed as aggressive and manlike. This is the Western racist history against Black women that Caster Semenya is up against. Ever since 2009 when Caster Semenya won the 800-m title at the 2009 World Championship in Berlin, Semenya has had to justify and legally fight the IAAF for the recognition of her female gender status. The latest of these fights is the IAAF’s new rule which seeks to force “hyperandrogenic” athletes to lower their testosterone levels below a prescribed amount if they wish to continue competing as women.