Male sex workers are a highly marginalised group in Hong Kong and it is increasingly so with an influx of them travelling from mainland China to work as "freelance" sex workers. This study aimed to measure important work environment variables that might affect the likelihood of condom use among male sex workers working in Hong Kong. A cross-sectional survey of 161 participants recruited by snowball and convenience sampling methods through outreach workers of a local non-governmental organization was conducted in 2007-2008. Only 27.4%, 54.7% and 42.6% reported consistent condom use when engaging in oral, anal and vaginal sex, respectively. Logistic regression shows unsafe sex was nearly four times (OR=3.41; 95%CI 1.51-7.69) as common in institutionalised male sex workers as among their independent counterparts. Lack of condoms provided at workplaces was a major barrier in this socio-legal context and was strongly associated with condom non-use amongst institutionalised sex workers (OR= 10.86; 95%CI 2.94-40.17). The present study finds that when compared with independent Male sex workers (MSWs), institutionalised MSWs were older, less educated, earned a higher income but more likely to engage in unsafe sex with their clients and their partners. Public health physicians must work with law-enforcing authorities to provide clear guidelines to remove these HIV prevention barriers.