According to public health research, bisexual men are at elevated risk for contracting STIs and HIV relative to other sexual minority groups (e.g., gay men, lesbian women) as well as heterosexual people; yet, no studies to date have examined contextual factors that may contribute to this sexual health trend. Using a minority stress theory framework, the present study tested the direct and indirect associations of anti-bisexual discrimination with risky sexual behaviors in a sample of 508 self-identified bisexual men (age range = 18 - 76), with internalized biphobia, bisexual identity concealment, and substance use mediating this relation. Bisexual identity centrality’s direct relations with internalized biphobia, bisexual identity concealment, and risky sexual behavior were also tested. A path analysis was used to analyze the data. Results indicated that anti-bisexual discrimination yielded significant direct positive associations with internalized biphobia, bisexual identity concealment, and risky sexual behavior. Internalized biphobia, but not bisexual identity concealment, yielded a significant direct association with substance use, which yielded a significant direct positive link with risky sexual behavior. Bisexual identity centrality yielded significant direct negative associations with both internalized biphobia and bisexual identity concealment, but it yielded a nonsignificant association with risky sexual behavior. Internalized biphobia also yielded a total indirect link with risky sexual behavior through the mediating role of substance use. Implications of these findings for clinical practice and future research with bisexual men are discussed.