CHICAGO — One was a teenage fan who sought R. Kelly’s autograph during his 2008 child pornography trial. Another was his 24-year-old hairdresser. According to documents released by prosecutors on Saturday, Mr. Kelly grabbed her by the head, tried to force her to perform oral sex and then ejaculated on her, leaving his DNA.

A third victim, prosecutors said, was a girl Mr. Kelly met at a restaurant during her 16th birthday celebration. Her mother was concerned about Mr. Kelly’s interest, so he helped her navigate around her parents.

According to prosecutors, he instructed the girl to take a cab to his studio after her father had dropped her at school. There, he gave her an envelope with “a large sum of money” and they began a once-a-month sexual relationship that lasted for about a year.

In revealing details of their case at a bond hearing in Chicago on Saturday, prosecutors portrayed Mr. Kelly as a man who repeatedly used his fame to draw girls and women into his orbit, and then turned them into targets for his sexual gratification.