Research suggests that sexual silence, family loyalty, and homophobia foster health-compromising behaviors among adult Latino gay males, but little is known about the effect of these sociocultural factors on the lives of Latino children and young teens characterized by gender nonconformity and homosexual orientation. This exploratory study of Puerto Rican men who have sex with men (MSM) used multisession qualitative interviews to examine early life experiences related to gender identity and homosexual orientation, and the place of drug use and risky sexual behavior in sexual identity formation. Gay male and transsexual female participants described at least one sympathetic family member, usually a female, who accepted cross-gender behavior and/or homosexual orientation. Half of the participants experienced unwanted sex as minors, and all were subjected to bullying by schoolmates. As pubescent youth, participants frequented adult gay venues where they were exposed to high-risk sexual and drug-related behaviors. Interventions for sexually questioning and gay/transsexual Puerto Rican youth are proposed. (Contains 1 table.)