The purpose of this study was to gain a better understanding of the context of heterosexual anal intercourse (HAI) among adolescents. Black and Latino youth were recruited at an urban college and an inner-city adolescent clinic. Participants completed a sexual behavioral questionnaire and the Sexual Relationship Power Scale (SRPS). A total of 61 young people, all of whom were sexually experienced, completed the survey (53 females; 8 males). Of these respondents, 20% reported engaging in HAI (N = 12), and 50% reported HAI refusal. The Relationship Control subscale scores of the SRPS were significantly inversely correlated with a history of HAI. Those who reported HAI or HAI refusal were invited to participate in an interview; 15 participants were interviewed. Most women found HAI distasteful, though some enjoyed it and instigated it. Most participants did not associate HAI with HIV-infection risk, and few used condoms. Some reported no longer using condoms for vaginal or oral intercourse after not using condoms for HAI and vice versa. The data suggest that there is no sexual script for HAI. HAI appears to be a complex behavior. Conventional views about it, as a way to preserve virginity or prevent pregnancy, may not be adequate. More research is needed to understand this behavior.