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Missy Elliott’s engagements with the queer female pleasures and possibilities of role playing extend to the accompanying music video for “Whatcha Think About That.” While the majority of the video finds Pussycat Dolls prepping backstage in lingerie, the scene shot for Missy Elliott’s rap is drastically different. This chapter examines three different artists and songs and how these black women and femme artists approach and articulate non-normative pleasures in play: Betty Davis’ 1974 song “He Was a Big Freak,” “Shockadelica” by Prince’s genderqueer femme alter ego Camille, and deals with Rihanna’s 2010 hit song “S&M.” Most consumers of popular culture are familiar with Prince’s play with and disruptions of norms of racialized gender and sexuality. In the spirit of genealogies of black women and femmes in BDSM, the chapter presents a brief discussion of Rihanna’s 2010 hit “S&M.”