The purpose of this study is to examine how men who sell sex to men perceive the risks in this activity and what experiences they have of actual denigration, threats, and violence in their relations with customers. We also discuss the self-defense strategies they have used to protect themselves. The study is based on an Internet survey on Swedish websites. Statistical analyses have been carried out, and in interpreting the results, Finkelhor and Asdigian’s revised routine activities theory has been used. The results show that the vulnerability of sellers of sex is greatest during the time when the sexual act is being performed, and that this is primarily linked to the customer’s antagonism and seeking gratification by overstepping agreed boundaries, particularly with regard to sexual services including BDSM. Their vulnerability was also connected to the seller’s diminished capacity for self-protection due to personal and external pressures. A smaller proportion of the men described risk prevention activities. These involved refusing a customer after an initial contact, protecting themselves from infection, being on their guard during the whole process, selecting the place, and deciding not to carry out certain sexual acts. An important implication concerns the occupational health and safety that men who sell sex to men can develop for themselves, while remaining within the law. International studies have demonstrated that selling sex in collective, indoor forms provides the greatest security. For decades, Swedish prostitution policy has had the ambition of reducing prostitution through targeting those who purchase sex, and those who promote prostitution in criminal legislation. This effectively prevents more systematic and collective attempts to create safer conditions for selling sex. In conclusion, it can be stated that while it is legal to sell sex in Sweden, this is done at the seller’s own risk.