African-American and Latino men who have sex with men (MSM) bear a disproportionately large burden of the Human Immunodefiency Virus (HIV) epidemic in the United States. To further enhance HIV prevention efforts among men of color, a survey was conducted within New York City’s house ball community; a community largely comprised of racial and ethnic minority persons. Time-space sampling was adapted to recruit participants for the survey from venues frequented by members of the house ball community. Using logistic regression analysis, this study examined the effects of perceived stigma, enacted stigma, sense of community and self-esteem on unprotected anal intercourse (UAI) among a sub-sample of men in the survey. Both perceived and enacted stigma had a modest direct effect on engaging in UAI. The direct effect on UAI was significant even after controlling for covariates in the model. The magnitude of the effect on UAI did not vary by race/ethnicity or sexual identity. In addition, perceived and enacted stigma correlated negatively to both sense of community and self-esteem scores. Although sense of community did not buffer the effect of perceived or enacted stigma on UAI, both sense of community and self-esteem were protective against engaging in UAI. However, while the direct effect of sense of community on UAI remained after controlling for covariates in the model, the effect self-esteem had on UAI diminished after adding variables to the model. Further, self-esteem was negatively correlated with both perceived and enacted stigma, but it did not mediate perceived and enacted stigma’s effect on UAI. Implications for HIV prevention strategies given these findings are discussed. Implications include developing multilevel interventions, including structural interventions, to reduce the stigma that is perceived and experienced by men of color as well as building stronger communities for African American and Latino MSM.