The purpose of this article is to provide a close reading of a thirteenth-century Hebrew narrative by Jacob Ben El‘azar of Toledo that recounts the tale of a “sodomite” who meets a violent end. The story focuses on the amorous affair of Sapir, an adult male, his beloved Shapir, a male youth around the age of puberty, and Birsha, a nefarious old man who lures Shapir away from Sapir, though Sapir ultimately seeks out Shapir and is reunited with him. Sapir and Birsha dispute over the boy and ultimately submit their case before a judge. The judge declares that Birsha deserves the death penalty, though he is spared this sentence and ordered only to forfeit the boy. Nevertheless, Sapir and Shapir take the law into their own hands and brutally murder Birsha. At the heart of the narrative is the tension between two models of eroticism between males, epitomized by the relationships of Sapir–Shapir and Birsha–Shapir, one sanctioned and the other condemned. The question that will be dealt with here is to determine what exactly distinguished the two relationships. Was Birsha considered a “sodomite” as opposed to Sapir, despite the fact that they both loved the male youth Shapir? Were they distinguished by their age, the nature of their desire, their sexual “identities,” their sexual acts, or other behaviors? (Foucault, The History of Sexuality, argued that the notion of sexual “identity” did not emerge until the modern era and that pre-modern societies thought only in terms of sexual acts. I largely agree with this evaluation though I will maintain that the categorization in the narrative under discussion distinguished between individuals who desired males and females versus those who desired males only.) In order to unravel this complicated narrative, we must delve deeply into the construction of sexuality within medieval Hebrew literature and more broadly within medieval Jewish culture—so enmeshed within its Islamic and Christian environments. I will argue that the identification of Birsha as a “sodomite” resided in his obsessive, mendacious, and violent qualities and not in his choice of love object, much less his sexual “identity.” Before presenting the narrative and my reading, I review some of the history of scholarship on homoeroticism in medieval Hebrew literature in order to provide a counterpoint to the methodological underpinnings of the present study. Throughout the study, I engage a variety of source types—Arabic homoerotic poems and narratives, Andalusi Hebrew poems, Christian reports of Muslim sexuality, exegetic and legal sources—in order to convey the highly specific and culturally circumscribed forms of homoeroticism assumed in Ben El‘azar's story.