In the last decade, public attention to the problem of commercially sexually exploited children (CSEC) has grown. This exploratory qualitative study examines adolescent pimping relationships, including how urban youth perceive these types of relationships. Study data stem from interviews with three young adult informants with first-hand knowledge of adolescent pimping, as well as three gender-specific focus group discussions with a convenience sample of 26 urban high school students who have first- or second-hand knowledge of adolescent pimping. Findings indicate that respondents believe teen pimping exists in their schools and communities, and that those exploited typically do not self-identify as victims. Respondents also believed that younger pimps are more likely to use violence to induce compliance among the girls they exploit, whereas older pimps are more likely to emotionally manipulate young women into exploitation. Further, respondents indicated that some young people agreed to exchange or sell sex for money as a favor to their boyfriends or girlfriends, and some young people believed that selling sex is acceptable under certain circumstances. The growing attention to CSEC provides an important opportunity to expand prevention efforts to reach those most affected and at risk for exploitation. The findings highlight critical areas for augmenting traditional content in school-based HIV/STI and sexuality education classes.