Empirical evidence on the heterosexual partnerships of long-haul truckers suggests connections among occupational stressors, substance misuse, structural factors, and risk for sexually transmitted infections and HIV. Yet the potential risks associated with same-sex partnerships of truckers and truckchasers (men who specifically cruise for truckers) remain largely unknown. Drawing from diverse sources as well as primary and secondary data from 173 truckers and "truckchasers," we discuss how trucking and cruising contexts, in conjunction with Internet fora, jointly create a risk-enabling environment for truckers and their sex contacts. Findings point toward an elusive but extensive sexual network that spans across the Internet and highways and takes advantage of truckers' mobility as it bridges disparate epidemiological spaces and populations. The delineation of cruising within the hypermasculine occupational sector of trucking adds new insights to the study of sexual health, which is particularly important considering the riskladen sex contacts of truckers and truckchasers and potential for infection spread.