Men who have sex with men (MSM) continue to bear a disproportionate HIV and sexually transmitted disease (STD) burden. The current study examined the frequency and associations of sexual risk reduction behaviors among a sample of MSM in the greater Boston, Massachusetts area. One hundred eighty-nine MSM completed a one-time behavioral and psychosocial assessment between March 2006 and May 2007. Logistic regression procedures examined the association of demographic, psychosocial, and behavioral factors with risk reduction practices. Twenty percent of the sample reported rimming, mutual masturbation, digital penetration, using sex toys, or 100% condom use as a means to reduce their risk of acquiring or transmitting HIV in the prior 12 months. In bivariate analyses, risk reducers were more likely to disclose their MSM status (i.e., be ''out''; odds ratio [OR] ¼ 3.64; p < 0.05), and report oral sex with a condom in the prior 12 months (OR ¼ 4.85; p < 0.01). They were less likely to report: depression (Center for Epidemiologic Studies Depression Scale [CES-D] score 16þ; OR ¼ 0.48; p < 0.05), a history of one or more sexually transmitted diseases (STDs; OR ¼ 0.40; p < 0.05), and meeting sexual partners at public cruising areas (OR ¼ 0.32; p < 0.01). In a multivariable model, risk reducers were less likely to report: alcohol use during sex (adjusted odds ratio [AOR] ¼ 0.33; p < 0.05), depression (CESD score 16þ; AOR ¼ 0.32; p < 0.05), or meeting sexual partners at public cruising areas (AOR ¼ 0.30; p < 0.05), or via the Internet (AOR ¼ 0.12; p < 0.05) in the previous 12 months. Identifying and understanding such factors associated with risk reduction behaviors may be important to consider in designing effective prevention interventions to promote sexual health for MSM.