This article draws on ethnographic research among two categories of male sex workers in the Dominican Republic in order to describe the relationships between gay male tourists and the Dominican men they hire on their trips to the Caribbean. Drawing on both qualitative interview data and quantitative surveys, the discussion examines the usefulness of theories of 'authenticity,' as they have been applied in the analysis of tourist practices more generally, in accounting for the behaviors and practices of male sex workers and their foreign gay clients. While the flow of international remittances from 'Western Union daddies' to their Dominican 'boys' creates a continuous reminder of the utilitarian nature of the exchange, both sex workers and clients are motivated to camouflage this instrumentality in their construction of a more 'authentic,' fulfilling relationship. The article examines the consequences of this ambivalent negotiation for the emotional and economic organization of gay male sex tourism in the Caribbean.