He is known as Jack Stones on his Facebook page, and authorities said he used that alias last Friday when he tried to enroll as a 15-year-old freshman at Marion High School in Illinois.
But by the following Monday, suspicious school officials had called the FBI and learned that Jack was born Jennifer May, and was actually 24-year-old Jack Jay Kaiser, a California woman in the midst of switching her gender to a man.
Today, Kaiser is being held in Williamson County jail on $20,000 bail, charged with lying to officials at the Illinois Department of Children and Family Services about his age and about having been abandoned or homeless.
"It's really sketchy," said Marshall Stone, supervisor special agent for the FBI's Springfield, Ill., unit. "We were initially involved because we were concerned if he was a trafficking victim and needed to be identified."
Now authorities are looking at a Web site created to research the "identities and pursuits" of pedophiles that may contain information about Kaiser.
"We are still investigating all aspects of this case. If warranted, more charges could be filed," said special federal officer Eric Breeze, who is working with the FBI Cyber Crimes Task Force assigned to this case.
Wikisposure, which is part of Perverted Justice, a nonprofit group that targets alleged sexual predators, described a 24-year-old Jennifer "Jack" Jay Kaiser who was transgender and used the online name "Lyrical Cancer," and who allegedly had associations with pedophile groups.
Gartner passed on the information she found on the site to the FBI, who said some of what was there matched what they were learning about Kaiser.
"A lot of the information on that Web page about that person is the same information we have about Jack Kaiser," said Breeze. "Especially that he was born female and was in the process of transgender and legally changing to Jack Kaiser."
"It's crazy," said Breeze, who said others in the task force, which handles child predator and computer intrusion crimes, likened the case to an episode of "Law & Order: Special Victims Unit."
But for now, the FBI will not comment further on the case and insists it is being handled as a local matter unless there is a federal violation involving exploitation of children.
The public defender assigned to Kaiser's case received the file Tuesday and was not available to discuss it with ABCNew.com.
Authorities said the incident began Oct. 9 when Kaiser -- calling himself Jack Stones -- and an older man identified as a professor from a local college attempted to enroll the youth as a high school freshman.
But school officials immediately became suspicious and kicked off safety protocols used in cases of noncustodial parents.
"An associate professor from a local university brought in a person who he passed off as a 15-year-old male," said Marion District Superintendent Wade Hudgens. "He had no forms, no birth certificate, Social Security number or anything. Our guidance counselors pay very close attention to these things to make sure people are who they say they are."
The boy had indicated on the school forms that he was a female transitioning to a male, Hudgens said.