May 15, 2009 -- 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.

Sugar Daddies Have 'No Time for Games'

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.

Law enforcement experts say Internet dating sites can be rife with predators.

"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."

Sugar Daddy Web Sites

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.

"The modern sugar daddy is not a rich, decrepit captain of industry exploiting empty-headed vixens for hedonistic pleasure, but a mature gentleman seeking fun and pleasure with women of substance," writes Wade, a pen name. "Nor are Sugar Babies all young bimbo-victims, but women who know what they want and go after it."

Wade, whose real name is Brandon Wey, is a 38-year-old MIT-trained engineer and self-proclaimed "geek" who is now married to his own decade-younger sugar baby.

Wade denied that his site was connected to prostitution or blackmail schemes and has created several features that help its 320,000 members spot a potential con artist, including software that blocks spam and flags language used by escort services.

EstablishedMen.com does not allow the "money for sex element" that typifies many of the other sites, according to CEO Simone Dadoun-Cohen, banning girls from asking for an "allowance."

However, he told ABCNews.com that "with any relationship service there is an inherent risk of deception between users which we cannot 100% control."

To counteract that risk, the site has a 24-hour "customer care team" that monitors profiles and "risk mitigation" technologies similar to those used by credit card networks.

Sugar Baby Offered $30,000 a Week

One sugar baby from SeekingArrangement.com would only use her initials AC when talking to ABCNews.com about her budding relationships with three sugar daddies who have offered her $20,000 to $30,000 a month.

"Ultimately, they want someone who is very physically attractive and a female that is sexual," she said. "A couple of them have been married, but their wives were beautiful, but not into that."

The California 37-year-old -- once married and now an entrepreneur and film maker looking for operating cash -- sees it as a business arrangement.

"One guy was so over-the-top and pretentious," she said. "He showed up in a big black Bentley with a driver and a security guard."

But recently, she has met a man who "understands women have needs" and like the fact that she is "business-minded and ambitious."

"He told me he was able to set me up and help me maintain my dreams," AC said. If the "chemistry" is there, they will sign a contract for their "arrangement."

AC said she doesn't feel like that arrangement is prostitution. "As an entrepreneur, you are constantly thinking outside the box," she said. "I have to be creative with the resources I have and we all know the economic situation and lending and investing is not available right now."

"Right now, people do all they can do to survive," she said.

Couple Arrested for Blackmail

Greenwich police arrested Dawn and Christopher Jessop, a young couple with three children, in a sting at a hotel where Dent was making the final $50,000 in a $100,000 pay-off, according to police reports.

"When I found out, I was absolutely devastated," said Christopher Jessop's mother, who runs a gourmet coffee shop in Mansfield, Ohio.

"He made decent money, so it's all about being greedy," Kelly Jessop told ABCNews.com.

Jessop's lawyer Mark Sherman said his client had "a tough decision to make."

"After a full investigation and at the appropriate time, he will accept responsibility for his conduct," Sherman told ABCNews.com.

"These kinds of problems go hand in hand with the Internet and all that comes with it," he said.

Dawn Jessop's lawyer said she, too, has entered a not guilty plea, but that was just a "starting point."

"We want to come to some agreed settlement," said Greenwich lawyer Mickey Sherman. "Her husband's accepting responsibility will help Dawn."

But, he told ABCNews.com, "The facts are pretty clear. There is a paper and Internet trail to everything."

Blackmail and the Internet

At least two others are accused of trying to blackmail Dent in the last two years, including one New York man -- the husband of a sugar baby - who was arrested in 2007.

Despite Dent's e-mail offers to pay for sex, police elected not to charge him with a crime, saying they did not want to deter other victims from coming forward, according to Dent's lawyer.

"I was surprised that people are so interested in this story," said Stamford, Conn., lawyer Stephen Frederick. "It seems to be about him, rather than the crime that was committed against him."

"He understands he made some terrible mistakes and regrets those mistakes and is paying for those mistakes," Frederick told ABCNews.com.

Those mistakes include explicit e-mails that were obtained by the Greenwich Times.

"I can only meet during the weekdays around midday," Dent allegedly wrote. "In general I am not available at night or during the weekends. Furthermore, we would need to meet only when my wife is away. Regarding your financial assistance, my initial thoughts are cash compensation in the range of $2,000 to $3,000 per meeting, assuming that we meet about twice a month, plus expenses."

Sugar Daddy as 'Gentleman'

"That sounds like an escort," said Wade. "We don't allow escorts on the site."

"These kinds of messages are not what sugar daddy dating is supposed to be," said Wade. "You don't have to be a millionaire to be a sugar daddy. You need to be a gentleman, generous and treat someone with respect."

Wade acknowledged that the site had fielded calls from two other men who thought they were being blackmailed and notified the FBI, but he downplayed the dangers of this kind of Internet dating.

"You can only do so much to protect your clients and there are always bad apples," he said. "And the thing about the Internet is that everything is traceable and you can get caught."

But law enforcement experts say that sites that promote wealthy sugar daddies are rife with possibilities for blackmailers.

Sugar Daddies Are Vulnerable

"On all these unmonitored Web sites, participants are in effect targeting vulnerable people," said Brad Garrett, former FBI agent and ABC News consultant. "They create a great environment for cons."

"It's like going back to the door-to-door salesmen who tried to find older, widowed women who live alone," he told ABCNews.com.

"Actually, it's a heck of a lot easier," he said. "Now you don't have to burn up the leather on your shoe. You basically go online and can even protect your own identity."

"The Internet is a dangerous place," acknowledged Dent's lawyer Frederick. "He hopes some good can come out of this. He cooperated with police to ensure that the perpetrators were brought to justice, despite personal risk."

Meanwhile, Dent is undergoing "treatment," according to Frederick. "These types of behaviors are not as unusual as people think."

And, he warned, "People don't understand the Internet is not as anonymous as it seems."

But Dent, whose 1986 New York Times wedding announcement boasted that he was the great-grandson of the business titan Alfred du Pont, may have been ultimately hoisted by his own financial petard.

"He's good-looking guy and very successful.... He was too rich and too bored," one Greenwich resident told ABCNews.com.

ABC reporter Jessica Golden and information specialist Gerard Middleton contributed to this report.