The average reported age of sexual debut for youth in the United States is 14.4 years, with approximately 7% reporting their sexual debut prior to age 13. While the research literature on sexual debut for youth addresses gender and ethnic differences (with males and African-American youth experiencing earlier sexual debut), there is limited data regarding factors associated with sexual debut for young men who have sex with men (YMSM). Early sexual debut poses potential health risks, such as contracting HIV with an increased risk of unprotected intercourse. Given current high HIV infection rates for racial/ethnic minority YMSM, learning more about their sexual debuts and associated risk factors of this population is of great importance. This study investigated risk behaviors and emotional distress, and their association with MSM sexual debut for a multisite cohort of racial/ethnic minority YMSM living with HIV. We hypothesized that a MSM sexual debut younger than age 16 would be associated with engagement in more high-risk sexual behaviors (unprotected sex and exchange sex), substance use, and emotional distress than a MSM sexual debut at age 16 or older. Results indicated that participants having a MSM sexual debut before the age of 16 reported more exchange sex; drug use (specifically marijuana); emotional/psychological problems related to substance use; and a history of suicide attempts, compared to participants with later MSM sexual debuts. Comprehensive interventions that are racially/ethnically sensitive, inquire about initial sexual experiences, and focus on sexual health and healthy relationships are needed to improve health outcomes for this population.