<p>Diverse perceptions of paying for sex notwithstanding, it is acknowledged as a societal concern in many countries worldwide, with no consensus reached regarding the most appropriate policies. The present study directed its attention toward heterosexual men who pay for sex and sought to explore the potential influences of distress and gender role conflict (GRC) on the likelihood of sex payment, while taking into consideration attitudes toward paying for sex as a mediating factor. Data were collected from a quota sample of 934 heterosexual Israeli men. Of all sociodemographic variables, regression analysis showed that lower level of religiosity was the only significant predictor of sex payment. Above and beyond religiosity, higher level of distress, the GRC scales of Restrictive Emotionality, Success/Power/Competition, and Conflict Between Work and Family Relations, and attitudes of paying for sex as a legitimate behavior were significant predictors of sex payment. Conversely, lower levels of Restrictive Affectionate Behavior Between Men and attitudes viewing paying for sex as a deviant behavior were also found to be significant predictors of paying for sex. Moreover, attitudes toward paying for sex fully mediated the association between distress, most of the components of GRC, and paying for sex. Our findings highlight the interconnectedness between masculine role socialization and men’s psychological experiences, and the potential relevance of these associations to men’s involvement in sex payment. Furthermore, the significant role of attitudes toward paying for sex in the actualization of sex payment is discussed.</p>