Sugar Daddies and Sugar Babes

Pasternack is a large, beefy man with a deep voice and eyes that always seem to be looking somewhere else. He wears a suit to work every day — in stark contrast to his employees on the other side of the glass — and he acts and speaks the part of the smooth CEO, extending his meaty arm, adorned with an expensive-looking watch, for a firm, friendly handshake. He has the cheery, smooth manner of a man who sells dreams.

There are dozens of sugar daddy Web sites — SugarDaddyForMe.com, WealthyMen.com, MillionaireMatch.com – but Pasternack, who started Sugardaddie.com in 2002, beat most of the others by about three years. There are 200,000 paying members on his site, he says; the women outnumber the men six to one. The oldest member is Richdaddyboy, an 87-year-old Londoner, "elderly but virile," his introduction states, in possession of some £260 million. The second-oldest member lives in Florida; he likes boating, fishing, and movies, and describes himself as "a very young 82." There are sugar mommies too: The eldest is a 68-year-old jazz singer in Nevada who is looking, she says, "for the last love of my life."

Membership costs $20 per month, with discounts for extended packages. Pasternack declines to say how much his company pulls in. "That we kind of like to keep quiet about," he says, "but you can say I've been very happy with the site."

Like any dating site, users create profiles and exchange e-mails or chat online. Anonymous self-descriptions are easily fudged, of course, so much of the Sugardaddie.com staff's time is devoted to screening new profiles and handling customer complaints, which tend to involve either lying or prostitution. Not surprising, the line between asking for a little sugar and expecting payment for sex is thin.

"One [woman] was like totally drugged out when I met her," Mr. Chips, a member in his forties, tells New Times. He's been on two dates since joining the site, and found both disappointing. "She answered the door naked, and she just stayed naked the whole time I was there. I watched her blow dry her hair for about half an hour, while she just listed all the things she wanted. She told me her hair extensions were like three grand or something.

"The other girl, we went to a sports bar and had burgers, and she told me she wanted 12 grand a month," Chips continues. "I thought that was rather excessive."

Pasternack insists he and his staff don't allow prostitution on the site. "Prostitution is strictly a business transaction, where you pay for someone by the hour or by the night. There's no relationship other than money exchanged for sex. A sugar daddy relationship is about caring for each other.... If they came there and say, 'Buy me Prada and I'll have sex with you,' they're gone. But if they say, 'I like nice things'...."

Pasternack addresses the distinction with a well-rehearsed philosophy. "We're all sugar daddies," he says with a confident smile. "It's just a question of to what degree."

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Liedra Lawson, a self-described career sugar baby, literally wrote the book on the subject: Sugar Daddy 101: What You Need to Know if You Want to Be a Sugar Baby. She also moderates what is likely the largest online hotbed of sugar daddy discussion, a Yahoo group called Sugardaddies101. It boasts more than 2500 members; hundreds of messages are posted on topics like what to do if a sugar daddy defaults on an allowance and how to set up bank accounts to which sugar daddies can easily wire money from abroad.

Miami, she says, is sugar city: "Believe you me, I could blackmail some people; you'd be surprised what there is in the Miami area.... In Miami it's almost a badge of honor for a girl to say, 'My sugar daddy did this for me'; it's acceptable if you're an emerging model. In Miami you'll find that a girl has to have a rich boyfriend, or else she'll turn to hooking."

Lawson's book is more than just a how-to guide: It's a manifesto. In an interview, she says women should be realistic and practical: "Be smart about it; have the guy be a business for you. I talk about women bettering themselves with this relationship.... I'm the kind of person who for my birthday I had my guy put $6000 in my account. You have to ask for more than the bling bling." She calls Anna Nicole Smith the "queen sugar baby.... She was just smart enough to get him to marry her and leave her his millions."

Still, the road to being a successful sugar baby isn't always smooth. I met Dolly, the living embodiment of the no-nonsense sugar-search, after I posted an ad on Craigslist. She agreed to meet at a Dunkin' Donuts in Aventura.