This article examines how a series of California court cases in the 1910s and 1920s recast the boundaries of American masculinity by tackling the ambiguities of sexual and social interaction between male adolescents and Asian migrant workers. Specifically, the prosecutors and police characterized South Asian and Chinese men as the importers of "unnatural" sexual practices. Police suspicion of illicit and immoral activity remade the spatial locations of contactÑthe streets, alleys, boardinghouses, labor camps, and ranches where migrant workers congregatedÑinto borderlands spaces. My critical approach tracks the transit of migrant workers and how their presence proliferates borderlands spaces along and beyond national borders. The surveillance of interracial contact and alleged sexual activity remade transient domestic and leisure spaces into sites of public scrutiny. My analysis tracks how prosecutors and judges deployed categories of normality and degeneracy to create racialized and sexualized typologies of masculinity to police the relationships of roaming male youth and foreign migrants in the early twentieth century. I argue that the jurisprudence in these cases reinterpreted and combined three seemingly distinctive strands of case law Ð sodomy, statutory rape, and vagrancy Ð to both explain and punish the contact between Asian migrants, domestic transients, and male adolescents. Yet the sexual and moral ambiguity of male adolescence confounded the jurists, forcing them to consider whether a youth was innocent, criminal, or delinquent. The protection of a specific male victim, however, became secondary to the protection of American society and civilization and the affirmation of normative masculinity. By extending the interpretive methodologies of queer borderlands scholars, this analysis denaturalizes the normalizing project of American nationality, masculinity, and heterosexuality. The policing of internal and external nomadic subjects revealed the ambiguity and insecurity of cross-racial and cross-class intimacy and intensified the fixing of new social boundaries of perversity and normality in the first decades of the twentieth century.