Extradyadic sex is a significant source of risk for sexually transmitted infections (STIs) among men in same-sex relationships. Nonmonogamous sexual agreements are common among male same-sex couples and may serve as effective targets for risk reduction interventions; however, there is a dearth of research reporting on the social and cultural determinants of explicit nonmonogamous agreements. In this study, it was hypothesized that attitudes toward dominant cultural standards of masculinity (i.e., normative masculinity) would be associated with the types of sexual agreements negotiated among gay male couples. An Internet-based survey was used to collect data from 931 men for this analysis. Results indicated that men who reported high endorsement of normative masculinity were more likely to be in nonmonogamous relationships. Furthermore, high endorsement of normative masculinity was predictive of relationship agreements characterized as the most sexually permissive. These findings indicate that rather than simply predicting nonmonogamy in gay male couples, attitudes toward masculinity may be indirectly related to increased risk of STIs by influencing the types of sexual agreements negotiated. This is the first empirical study to emphasize the role of masculinity as an explanatory factor of same-sex relationship agreements.