Male sex workers (MSW) are a particularly high-risk subset of men who have sex with men in Lebanon and report higher numbers of sex partners and lower rates of condom use. The purpose was to explore the factors influencing sexual risk behaviors and HIV testing among MSW. Qualitative interviews were conducted with 16 MSW living in Beirut and working in bathhouses (hammam) or as escorts; content analysis identified emergent themes. Escorts reported more consistent condom use with clients and HIV testing than hammam MSW, with influential factors including HIV risk knowledge and perceived risk susceptibility, job security, and internalized stigma and related feelings of self-worth and fatalism regarding health and HIV risk. In contrast, both groups of MSW typically opted not to condoms with nonclient sex partners, in an effort to differentiate sex for work versus pleasure. The uptake of HIV testing was limited by concerns about the confidentiality of the test results and fear of repercussions of a positive test result for their health and employment. The respondents described an insular existence within the sex work culture, in part to limit exposure to stigma, which has implications for access to support as well as the influence of peer norms regarding sexual risk behavior and health seeking behaviors such as HIV testing. Further research is needed to tailor prevention and HIV testing efforts to reflect the distinct sexual health “cultures” that distinguish these two populations of MSW in Lebanon.