Data came from the experiences of The Bridge, Inc., an agency working with street youth, and from interviews with 28 male street youths involved in prostitution in Boston. Hustlers (those who perform sexual services for money, drugs, and other reward) vary in age, length of stay on the street, sexuality, lifestyle, and motivation. The youths generally reported troubled family histories and memories of parental fighting, drinking, and neglect. They also recalled poor relationships with families, adults, and friends. They perceived themselves as isolated, victimized, and unsuccessful in school and with peers. Most hustlers must work more often and for less money at later stages of their careers than earlier on. They usually set a minimum price and negotiate upward. What distinguished the male prostitutes from street youths in the study sample not involved in prostitution was the incidence of coercive sexual activity at an early age for the male prostitutes. It is postulated that hustling becomes a viable option for youths who have run away and are alone, without resources, unable to dispel the anxiety generated by sexual abuse, and forced to make a living on the street. Types of male prostitutes within the sample are identified by demography and lifestyles, and their introduction to prostitution is discussed. Female prostitution is briefly mentioned. Brief sexual histories of some respondents and 29 footnotes are included.