Explicit sex and sexuality have come to figure more prominently in mainstream media and popular culture in recent years, sparking public concern and scholarly debate on how the “sexualization” of culture particularly affects women. Against this backdrop and amidst digitally reconfigured circuits of media production and consumption, ordinary women participate in, and potentially profit from, the commodification of sexual interactions and relationships. This study compares women’s practices in cultures of cam modeling and sugar dating in order to better understand their meanings and contexts. Whether performed in tandem with romantic dating scripts and roles, as is common in sugar dating, or in the intimate yet solitary context of domestic spaces, as is common in cam modeling, both practices illustrate the ways in which digital media reconfigure the sites, contexts, and cultural practices of erotic labor. They also make salient the complex and constrained ways women claim sexual and economic sovereignty in the contemporary United States, and the resistances they continue to face. Therefore, ethnographic exploration of women’s lived experiences of cam modeling and sugar dating moves beyond critical assessments of commodified sex and intimacy as exploitative or oppressive. This study takes such an approach, exploring the ways in which women “make do” within commercial relationships, organizations, and networks of sexual cultural production, opening up possibilities for agency within structural constraints, pleasure under disciplinary regimes, creative sexual expression supported by online sexual labor, and new forms of intimacy in highly mediated social environments. It sheds light on how women organize, make sense of, and derive value from these practices. It also examines how their participation might expand, constrain, or complicate the realm of meanings and identities available to them in a changing cultural, political, and economic environment.