Nearly 20 million new sexually transmitted infections occur every year in the United States. Traditionally, men have demonstrated much greater risk for contraction of and mortality from STDs perhaps because they tend to engage in a number of risky sexual activities. Research on masculinity suggests that gender roles influence males' sexual health by encouraging risk-taking behavior, discouraging access to health services, and narrowly defining their roles as partners. However, despite the propensity of highly masculine men to engage in high-risk sexual behavior, there is reason to suspect that men at the other end of the continuum may still be driven to engage in similar high-risk behaviors as a consequence of gender socialization. Discrepancy stress is a form of gender role stress that occurs when men fail to live up to the ideal manhood derived from societal prescriptions (i.e., Gender Role Discrepancy). In the present study, we surveyed a national sample of 600 men via Amazon Mechanical Turk to assess perceived gender role discrepancy, experience of discrepancy stress, and the associations with risky sexual behavior and potential contraction of STDs. Results indicated that men who believe they are less masculine than the typical man (i.e., gender role discrepancy) and experience distress stemming from this discrepancy (i.e., discrepancy stress) engage in high-risk sexual behavior and are subsequently diagnosed with more STDs. Findings are discussed in relation to implications for primary prevention strategies.