Stephen Dent was perceived, above all, to be a family man, playing ice hockey with his two sons on the weekends, vacationing in Palm Beach and Nantucket.
But behind closed doors, the 54-year-old Greenwich, Conn., multimillionaire was a "sugar daddy" and "slave master" who courted his "sugar babies" online, lavishing them with thousands of dollars in exchange for companionship and kinky sex, according to court records.
But his sex life turned sour because he was repeatedly extorted over his flings with numerous sugar babies on the dating Web site SeekingArrangement.com, according to court records. Now police are charging a young couple with blackmailing Dent.
Dating sites like Wealthymen.com, Sugardaddy.com, Establishedmen.com and others can be fertile ground for con artists who take advantage of men with deep pockets, like Dent.
"The news is unbelievable," said one family acquaintance who did not want to be identified. "I am completely blown away by this. I've always seen him with his wife and children all the time and, honestly, he seems to be a real family man."
"Anybody on the outside would say his life is perfect," the acquaintance told ABCNews.com.
Just this week, the Greenwich Times exposed Dent and the five-month long investigation by Greenwich police and the FBI.
Court records revealed that Dent -- a New England blue-blood and worth $100 million -- was the "nameless victim" in at least three sexual blackmail plots, paying out more than $200,000 to keep his online sex life secret.
In this affluent community where Dent owns his own investment company and a $4.5 million home on a private cul-de-sac, news travels fast in the country club circles.
Now, he is even ridiculed by some neighbors for driving a gaudy orange car.
"Every time I see it, all I can think about is a guy who thinks with his penis would drive it," she told ABCNews.com. "It's sort of a visceral reaction."
"It's a Corvette-ish looking thing in a loud and ugly shade of orange that you can't help but notice," said one of Dent's neighbors, who did not want her name used.
Dent's fall from grace began in the online dating community SeekingArrangement.com, where rich men who "have no time for games" can "mentor or spoil" a "personal secretary, secret lover or student."
That arrangement is mostly financial, attracting sugar babies who are "attractive, ambitious and young" -- college students, aspiring actresses or "someone just starting out."
There, the average age of a sugar daddy is 45 and a female sugar baby is 26, according to company spokesman Stephan Smith.
"This guy has two vulnerabilities," said Kenneth Lanning, a former FBI agent. "He has a sexual need and they turned on him. That is the foundation and fundamental building block of all con schemes."
The concept of sugar daddies and their sugar babies is spelled out in a new book, "Seeking Arrangement: The Definitive Guide to Sugar Daddy and Mutually Beneficial Relationships" by Brandon Wade, who owns the Nevada-based Web site where Dent met the alleged blackmailers.