With a stratified multi-stage sampling approach, 1361 male factory workers in the Longhua district of the Shenzhen Municipality of China were selected to investigate the multifaceted determinants of sexual intercourse with non-regular female sex partners (NRP) and female sex workers (FSW) among them. The results showed that 24.5% and 21.2% of participants had sexual intercourse with NRP and FSW in the past 6 months, respectively. More specifically, at the individual level, perceived higher job stress and maladaptive coping styles were linked with a higher likelihood of having sexual intercourse with NRP and FSW (adjusted odds ratios [AOR] ranged from 1.06 to 1.17). At the interpersonal level, those who had higher exposure to information related to sexual intercourse with NRP or FSW were more likely to have sex with these female sex partners (AOR: 1.08 & 1.11). At the social structural level, perceived social norms supporting multiple sex partnerships were linked with a higher likelihood of having sexual intercourse with NRP and FSW (AOR: 1.10 & 1.11). No interaction effects were found between the variables at different levels. Providing pre-employment training to clarify roles and job duties, introducing adaptive coping strategies, and addressing misconceptions of social norms are useful strategies to reduce sexual intercourse with NRP or FSW.