Recent meta-analytic work has endorsed a lack of any meaningful, direct relationship between internalized homonegativity (IH) and high-risk sex. It may not be possible to observe a direct association, however, if heterogeneity in response to IH is considered. This investigation used data from 1,669 men who have sex with men who completed an online survey of sexual behavior in 2005 to consider two potential intermediate variables (compulsive sexual behavior [CSB] and the frequency of sexual partnering) that could increase (CSB) and decrease (frequency of sexual partnering) the probability of having unprotected anal sexual intercourse. We used Mplus (Version 5.1) to estimate confirmatory factor analysis and structural models. Statistical mediation models identified indirect associations through both CSB (positive association) and the number of male sexual partners (negative association). The different directions of association, when combined, cancelled out one another. This contributed to the observed lack of association between IH and high-risk sexual behavior. Future work on risk behavior that incorporates IH will need to consider heterogeneity in how individuals respond to the construct and how these different processes are associated with risk behavior.