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Sugar On Top
  • November 02, 2012 : 00:11
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“Well, the first thing is you’re driving a Ford Taurus,” his friend said. “Go buy a nice car.”

Ridiculous, Jim insisted. Women aren’t that shallow. They’ll see through that right away.

But he tried it. “What I found is if I picked a woman up in a Rolls and was wearing a nice suit, I was going to get laid.” Fancy cars and expensive clothes were the male version of big boobs.

Then he discovered Sugar Daddy 101, a guidebook that turned his insight into an entire philosophy of modern, eyes-open intimate relationships. There was a price on everything, it argued, and wise women learned what it was. From the book he found his way to the Seeking Arrangement website, which certifies the assets of its sugar daddies and sugar couples so potential sugar babies know what they’re getting into.

Jim got certified to $10 million and began to experiment. He became obsessed with beauty, and, man, was it a rush. But like all rushes it faded, and he found himself stuck with too many vacuous beauties. So he started focusing on personality.

This led to an unexpected pleasure when one young woman he dated, someone he genuinely liked, admitted that she’d gotten deep into money problems that even Jim’s monthly sweetener couldn’t resolve. He got out his calculator and spreadsheets and helped her restructure her finances. After that, mentoring became a large part of his pleasure in the sugar lifestyle. “I really do feel like I’m making a positive contribution to society and to these girls in particular,” he says.

Jim and Kelly insist there’s a difference between a college girl paying her tuition and a full-time sex worker paying her rent. “Because then it becomes prostitution,” Jim says. (Alas, the cop who answered the phone at the Atlanta Police Department snorted in derision at this notion. “You can’t pay for sex for any monetary gain,” he said.)

“The idea that someone I’m going to be with has been with five guys already, that’s just gross to me,” Kelly says.

“We’re in a difficult position to be judging anyone,” Jim says, “but that’s not attractive. It’s just not attractive.”

“I’m very much a feminist,” Kelly says. “I think women should support themselves, not rely on a guy.”

And what about the idea that for someone as young as Jodie, being a sugar baby might be a formative experience that will warp her life?

“She was on the website already,” Kelly says. “We didn’t go drag her on the website.”

In Jim’s mind, that’s one more reason to like college girls. They’re smart enough to make thoughtful decisions. Jodie knows what she wants from life and is taking pragmatic steps to achieve it. Jim admires that. “If she thought we were taking advantage of her,” he says, “she wouldn’t be doing this.”

Let’s get a little more comfortable, shall we? Into the Rolls! Oh, how beautifully money expresses itself in stitched-leather seats and a hammered-aluminum dashboard. “Nothing bad ever happens in a Rolls-Royce,” says Jodie.

An hour’s drive brings us to Jim and Kelly’s gorgeous home in an Atlanta suburb. There’s a sitting room with a family portrait, a dining room centered around an antique mahogany table, four large bedrooms and a magnificent kitchen: elegant yet homey.

Kelly’s daughter’s room is an explosion of pink with castles and butterflies but no TV. Except for prescreened Disney movies, Jennifer has never watched TV. “I don’t want her to watch commercials and say commercial things and want things,” Kelly says.

Soon Jennifer comes home from school, a Hummel figurine in a white shirt and black skirt, her straight hair pulled back with a black headband. Kelly asks what she learned in school.


Nothing? I want to talk to your teacher!”

At dinner, Vivaldi plays as Jim talks about his kids from his first marriage, how they’re sending out résumés, looking for jobs, how tough things are now. The housekeeper sits with them. Then Kelly takes Jennifer off to bed and Jim sits down to explore the latest offerings from Seeking Arrangement. Since these relationships tend to fade out and Kelly wants a date night once a week, Jim does a little bit of this every day. Right now he’s looking for Jodie’s summer replacement. His in-box has 182 messages.

“Oh, it’s just never-ending,” he says. “We get four or five e-mails a day, on the weekends 20 or 30 a day. There’s no way you could meet all these girls.”

Here’s a 20-year-old hardbody from Turks and Caicos. “Hi, I am a young pretty sweetheart and would love to meet someone older, confident and kind.”

Jim likes her body, but she’s not educated.

Here’s Nikki, a 21-year-old from New Jersey who specifically requests a sugar couple. That’s unusual, though less unusual than it used to be. And she’s a college student who says she’s been through tough times, which is good because she’s being honest. Jim cuts and pastes one of his prewritten responses: “Hi, I’m Jim, an old-school Southern gentleman.…” Here’s a prospect from San Francisco with an amazing body. “I’m a lusty, petite and curvy woman of passion and pleasure,” she begins.

She’s overselling. Jim deletes her.

When Kelly comes in, the delete rate soars. First to go is a 28-year-old who says she wants no less than $20,000 a month. “This is crazy talk,” Kelly says. “I wouldn’t even give this girl the time of day.”

Here’s Taylor, a beauty from a small town in Alabama who “has some stresses a pretty girl shouldn’t have to fret over.”

“She’s a little chunky,” Kelly says. She stops at a young blonde. “She looks hot. I go for blondes. How old is she?”

Twenty-six. Which means she’s probably 32, Kelly says.


A professional musician strikes Jim as the perfect girl next door. Kelly disagrees. “I think this girl is a man.”

The next one’s willing to relocate. “This girl needs a place to live,” Kelly says.

Should Kelly be a little more sensitive? Is it weird for a woman who calls herself a feminist to judge her sisters so harshly?

“We just have our pick,” says Kelly. “It sounds wrong and it’s not very feminist, but it’s a fact of life. And as the recession gets worse, it gets better.”

Finally they find a prospect who looks as though she walked out of a Victoria’s Secret catalog. “If that’s really her,” Kelly says, “she’s hot.”

Jim scans the profile. “Look, there’s a comma after ‘whoever.’ And there’s an ellipsis, and it’s actually in the correct place. She can punctuate!”

“This one will never go for us,” Kelly says. “She’s gorgeous, she’s smart, she writes coherent sentences. She’ll be going for a billionaire.”

This is where Jim takes over. “We’ll find out,” he says, executing a quick cut-and-paste, sending a blast of desire along with the hydraulic whoosh of outgoing e-mail: “Hi, I’m Jim, an old-school Southern gentleman.…”

In the morning Kelly comes down to the kitchen in a pair of pink Hello Kitty pajamas. Slicing strawberries for Jennifer’s cereal, she announces her plans. “Mama’s going to be gone tonight.”

“That’s twice this week,” Jennifer says.

“I’ll be back.”

“I don’t know if you will,” Jennifer says.

“When do I not deliver on what I say? Your mom’s a rock. If I say something, it happens. You don’t have one of those flaky moms. The only thing that could keep me from making your soccer game is if there’s a delay in flights, which I can’t control.” After good-bye kisses, Kelly heads out in the Navigator to pick up Jodie; today they’re flying to the coast so Kelly can introduce Jodie to the Executive. This will probably lead to a three-way, which would be Kelly’s first three-way without Jim since they got engaged.

On the way, she tells her version of their story. She met Jim on Seeking Arrangement five years ago. At first she dated other sugar daddies, and Jim had other sugar babies. It was just fun, and Jim’s secret kink tickled her fantasy. “The idea that my dorky boyfriend was banging these hot girls with huge tits,” she says, “that turned me on.”

Gradually it became clear there was serious potential in the relationship. They clicked. Kelly is fire and Jim is earth, Kelly the hard-charger and Jim the quiet force who keeps everything in balance. Even their relatives thought so. Her mother told Jim, “Usually Kelly runs right over men, but you know when to shut her down.”

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read more: lifestyle, Sex and Dating, sex, relationships, issue december 2012


  • Anonymous
    Sexy and provocative. I loved every bit of this story.
  • Anonymous
    This article reads like it could be a very addictive reality show... :) Love every minute of it.