This chapter examines how some selected Kenyan literary writers illuminate the dynamics of gendered identity construction in the context of Judith Butler’s concept of performativity. Butler’s argument is that identity is not what bodies produce, but what power produces through reiteration and repeated citation. And that identity is an effect produced through practice and named by discourse. Butler’s argument helps us in understanding how prescription of gender roles creates heterosexual hierarchy within society and how this leads to fragmentation of youth identities. It is for this reason that the study interrogates formation of youth social identities as depicted in Florence Mbaya’s Sunrise at Midnight, Bill Rutto’s Death Trap, and Carolyne Adalla’s Confessions of an Aids Victim. The study therefore uses qualitative research approaches to gather textual data from the selected texts. It applies purposive sampling of primary texts that reflect the youth living in Kenya in the twenty-first century. The selection of the three texts spaced over three decades allows this critique to locate the textual analysis within the real-life experience of gender construction over time. The study concludes that gendered identity in contemporary Kenyan society has been reconstructed and redefined.