The association of trauma exposure and coping style to sexual risk behavior has yet to be fully examined in the context of primary and casual sexual partnerships. The current study assessed a high risk sexual behavior-unprotected anal intercourse (UAI)-in a high risk population of HIV-positive men who have sex with men (MSM) with a history of trauma. Using audio computer-assisted self-interview technology, 132 HIV-positive MSM completed measures of trauma exposure, trauma symptoms, coping strategies, and sexual risk behavior. Hierarchical logistic regression analyses indicated that completing more years of education and having experienced sexual abuse were positively associated with UAI with casual partners. Additionally, use of active coping was negatively associated with UAI with casual partners and the final model significantly predicted variance in UAI with casual partners. However, no variables were significantly associated with UAI with primary partners, suggesting that sexual risk behavior with primary partners may be associated with factors not commonly assessed in risk prediction or prevention research. We discuss the results in the context of developing new or modifying existing interventions to address rates of sexual risk in the relationships of HIV-positive MSM.