A sample of 498 sexually active first-year students matriculating at a historically Black college in North Carolina was used to determine correlates of risky sexual behaviors. In an Ordinary Least Squares regression, the self-esteem element "I take a positive attitude toward myself" (B=1.12, p=.05), non-condom use because of partner issues (B=.53, p=.05) and being drunk or high (B=1.20, p=.001), oral sex (B=1.74, p=.001), anal sex (B=.61, p=.04), and bisexuality (B=.85, p=.03) all increased the number of these behaviors. Higher scores on the condom usage scale (B=-.38, p=.002) were found to decrease the number of risky sexual behaviors. Illicit drug use was an underpinning of the surprisingly positive relationship between positive self-image and risky sexual behaviors. It was concluded that school-based social workers, mental health care professionals, and community-based prevention providers can play a critical role in the training of peer facilitators, development, and supervision of peer-driven risk-reduction programs to address the complex interplay among self-esteem, sex, and substances.