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This study examined the circumstances surrounding a homeless youth’s “decision” to trade sex for food, money, shelter, or drugs. Forty homeless youth in 4 Midwestern states participated in individual, in-depth qualitative interviews. Interviewers recruited youth through both service agencies and street outreach. The findings revealed that approximately one third of the sample had some experience with trading sex, whether it was in the form of having traded sex, having been propositioned to trade sex but having refused, or having friends or acquaintances that had traded sex. Young people ‘s reports indicated that they had traded sex for things they deemed necessary in order to survive (i.e., food, shelter, money, or drugs) and that they did not want to trade sex, but did so because they were desperate and lacked alternatives. Additionally, others were coerced, manipulated, or forced to do so, indicating that the decision to trade sex is not always voluntary. We discuss the implications of these findings in terms of cumulative effects on youths’ later development. Directions for future research among this population are also discussed.