Commercial sex workers (CSWs) in the Russian Federation are at high risk of HIV infection and transmission as a result of unsafe sexual and injecting behaviors. Their clients might be at increased risk of acquiring HIV; however, little is known about the population of men purchasing sex services. This study aims to investigate factors associated with a history of purchasing sex services by men in Saint Petersburg and Leningrad Oblast, Russian Federation. Data were collected as part of a cross-sectional study offering free anonymous rapid HIV testing in Saint Petersburg and Leningrad Oblast in 2014; in total, 3565 men aged 18 years and older provided information about their behaviors associated with risk of acquiring HIV during face-to-face interviews. Prevalence of CSW use in our study was 23.9 %. Multivariable analyses using log-binomial regression were stratified by self-reported HIV testing during the 12 months preceding the study interview. In both strata, older age, multiple sex partners, and a history of sex with an injection drug user (IDU) were associated with an elevated prevalence ratio (PR) for history of purchasing sex services, although the strength of the association differed by strata. Among men who reported recent HIV testing, condom use (PR = 1.22, 90 % confidence interval (CI) 1.0, 1.48) was associated with a history of purchasing sex services, and among men who did not report recent HIV testing, having a consistent sex partner was associated with purchasing sex services (PR = 1.23, 90 % CI 1.1, 1.37). The high prevalence of CSW service use and associations found in this study raise serious concerns about potential for sexual HIV transmission and should be investigated more closely.