Adolescents reporting selling sex for payment were studied with respect to socioeconomic background, perceived mental health and health behavior, antisocial behavior, sexual experiences, including sexual abuse and abusive behaviors, and the use of pornography. The sample consisted of a representative sample of 4,339 students (response rate, 77.2%) from the third year of upper secondary schools in five Swedish cities. Of the participating adolescents, 1.8% of the boys and 1.0% of the girls indicated that they had sold sex for money or other reimbursements. Selling sex was associated with having an immigrant background, higher level of unemployment in the family, and studying a practical/vocational program. Adolescents with the experience of selling sex had an increased risk for different psychosocial problems, such as poorer mental health, weekly use of alcohol, and antisocial behaviors. The adolescents selling sex were also characterized by having had a greater number of sexual experiences, a greater preoccupation with sex, relatively early sexual debut, and experience with sexual abuse as victim and/or perpetrator. The index group students watched pornography more frequently than the majority and they also watched more deviant forms of pornography. The significance of the higher frequency among boys and the gray zone between normal sexual exploration and prostitution are discussed.