An online relationship that began on a “sugar daddy” web site ended in a series of extortionate demands by a Florida woman who threatened to distribute nude photos sent to her by the 56-year-old male victim, according to investigators.

Stephanie Starling, 26, was arrested Monday in connection with her alleged shakedown of a married Las Vegas businessman identified in court records by his initials, “H.T.”

As detailed in a felony extortion complaint, Starling, seen at right, met “H.T.” on sugardaddyforme.com, a “dating” web site that matches women in need of money and men with said money. “H.T.” told FBI agents that he joined the site (which charges up to $53.85 a month) in mid-2012 and “began an online relationship” with Starling in September or October.

Starling, “H.T.” recalled, claimed to be a 21-year-old college student from Jacksonville. The photos she first shared with “H.T” actually depicted a blonde model who appeared in porno films. Starling is pictured above in a photo from her Facebook page.   

During their initial communications, “H.T.” voluntarily agreed to send Starling $7000 to cover “various school and living expenses.” The pair also exchanged “several revealing and nude photographs of each other.” But while “H.T” sent Starling explicit photos of himself, she sent naked images of another woman she found online.

Starling claimed she signed up to sugardaddyforme.com because she was “struggling to pay bills and feed” her young son. Starling, who said that “H.T.” “told me he wanted to have me as his side girlfriend,” told agents that she had relationships with “approximately five or six men” she met via the web site.

In late-November, after “H.T.” declined to send Starling any additional funds, she began threatening to send his naked photos to his family, employer, and various social networking sites. “H.T.” wired Starling an additional $1200 via Western Union after she assured him, “You have my word you’ll never hear from me again.”

That pledge lasted about three weeks.

In a series of escalating threats, Starling warned “H.T.” that if he did not send more money, “I’m messaging your wife.” Referring to money being sent to her, Starling texted, “I better have a tracking number by 6pm my time or I’m making you famous.”

In subsequent messages, Starling threatened to harm “H.T.” and his family. “I’m gonna come to Vegas,” she wrote, adding, “I will never fucking stop until I get my money or you die.” In one February 23 text to “H.T.,” Starling reported, “Stalking your Twitter now.” As seen on Starling’s Twitter page, she sent “H.T.” two messages that day: “found you” and “you should answer me back.”

After "H.T." contacted the FBI, agents opened an investigation in early-February. Investigators traced the extortion demands to Starling’s Jacksonville home, which they searched Monday. During the raid, Starling spoke with FBI agents and admitted sending “H.T.” threatening communications. “I will never do that again,” she said. “I know what I was doing was wrong.”

In a four-page handwritten confession, Starling said she was “in college aspiring to become a dentist” and was “sorry for the stress and pain I caused him.” She added, “I want to be able to go home to my son tonight.”

Starling, who was jailed following her arrest Monday, was scheduled today for a detention hearing in U.S. District Court in Jacksonville. If convicted of the extortion rap, she faces a maximum of 20 years in prison.