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Sugar On Top
  • November 02, 2012 : 00:11
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She says her friends joke, “‘I wish I had a sugar daddy,’” and she thinks to herself, Ha-ha, I do have one.

“And a sugar mommy too,” Kelly adds.

Jim and Kelly pay her tuition, from $3,000 to $5,000 a month.

Jodie says she loves the secret life. “Everybody wants to know what I do. Like, ‘Where does Jodie go? Where is she sneaking off to? Why is Jodie talking about the Opus One she drank last night? Where did Jodie get that Lilly Pulitzer dress?’ “And they’ll never know,” Jodie says. “It’s my little secret.”

The secrecy is especially delicious because Jodie belongs to a sorority where Lilly Pulitzer dresses are the thing, and she could never afford one on her own. So Kelly took her shopping and bought her a Lilly dress, and when she got back, her sisters just died. How did Jodie get a Lilly dress? She was so thrilled she sent Kelly a text message: “You turned me into a Lilly whore!”

Kelly smiles, almost like a proud mother. “Her first Lilly dress.”

Their initial meeting was on Skype. Jodie had sent Jim and Kelly a note through because their profile seemed normal and safe and especially because Kelly had once been a sugar baby on Seeking Arrangement herself. She wasn’t some wife who was pissed off because she had to do this to save her marriage. And Jodie liked how honest Jim was. From the beginning he said, “Here’s my name; google me. You know I come from a semifamous family, and you’ll see my pictures and all the committees and boards I’ve served on.”

Kelly teases Jodie for showing up for that first Skype call directly after a workout, hair still sweaty. “It’s all slicked back and greasy and she has this sports-bra uniboob going on,” Kelly says. “She’s like, ‘Yeah, I just got back from the gym. Do you think I’m hot?’ Jim’s like, ‘Oh my God, I don’t know. She looks a little too—’?”

“Sporty,” Jodie supplies with a giggle.

Flat-chested would be another word. Jim likes curvy, but Kelly liked her.

“I’m not attracted to somebody my age,” Kelly says. “It’s a fantasy for me—I don’t want to fuck myself. I wanna be with some hot young thing. That’s my fantasy.”

After the Skype meeting, they met at a hotel near Jodie’s college. Jim and Kelly seemed so normal. They were a family, raising a child together. Other than that, it was just like any other blind date. They ordered wine. They ordered dinner. Kelly gave Jodie advice on how to avoid creeps and how to cut her meat.

Jodie had a million questions. What do you guys do in bed? How many sugar babies do you have at once? How many have you had? Am I going to be hanging out with other girls?

Kelly laughs, remembering the evening. “Oh, if only Jim was 18 again.” She turns to Jim. “I don’t think you can handle yourself in a large group.”

He laughs. “In my dreams.”

She also teases him about wearing plaid. “All you need is the pocket protector and you’d be all set, babe.”

Jodie joins in. “It’s best when he pairs it with the short shorts and the high socks.”

Jim takes the abuse as gracefully as he carries his big gut, confident in his manliness.

The arrangement is especially nice, Jodie says, because Jim and Kelly don’t care if she dates other people. Instead they say, “Tell us about it.” Like this guy Jodie dated who was 36. Kelly said he was too old but not old enough.

“Young and hot or old and wealthy,” Kelly explains. “I mean, really, there’s no in-between.”

Jim’s pied-à-terre is on a high floor of a building right in the heart of Atlanta’s Buckhead district. As Jim finds a suitable wine, the conversation steers to Kelly. How did she end up a sugar mama?

Kelly grew up a math nerd in Connecticut with strict Catholic parents who had sex only three times to produce each of their three children. Or at least that’s Kelly’s theory. Her dad was an engineer, her mom a school administrator. Both were very frugal. College was paid for, but she never had a designer dress. That was wasteful. What’s wrong with JCPenney?

Sex was Kelly’s rebellion. She had three-ways in college. She went to sex clubs. Most of all, she fantasized about being a geisha. One night a rich boyfriend gave her a roll of bills and told her to buy a new bed for them to fuck in. “Like, that was just hot for me.” Next time, he gave her $500 to buy a bottle of wine. “Think of me when you drink it,” he said.

But the pull of convention was too strong. Kelly graduated from a respected college and went to work for a legendary computer company. She married an age-and income-appropriate guy and paid her mortgage six months in advance—until the day when she became fed up with her husband’s drinking problem. After the divorce, she went looking for a man who would treat her the way her rich boyfriend had.

“Even though I was making a lot of money, I was banking it,” she explains. And if a rich boyfriend offered her money? “I’m still making Mom and Dad happy,” she says, “because I can use his money to get that designer dress. I can use his money to get Jimmy Choo shoes.”

Now Kelly is like a missionary for the sugar lifestyle. She sees the college boy with his shirt open showing off his abs and thinks nothing at all. But an older guy with a briefcase and a hint of gray? Hot. With summer break coming, she’s even planning to fly Jodie to the coast to introduce her to a distinguished older gentleman (we’ll call him the Executive). This is because sugar relationships have a shelf life of about six months, says Kelly. Then it’s often on to the next thing for all involved.

After all, Jodie’s used to the lifestyle now. “It’s like a special thing,” Jodie says. “Pretty much helping me out.” Jodie is very happy to get Kelly’s advice. “Kelly knows everything in this industry,” she says.

Kelly’s eyebrows go up. “Industry?”

“I mean lifestyle,” Jodie says. “I don’t even know what to call it. She knows what she’s talking about. I mean, they even go so far as to tell me, ‘Do not cut up all your meat before you eat it. Cut it one slice at a time.’?”

“Yeah, I’m teaching her: Put your napkin in your lap; don’t suck down your wine in one gulp.… I’m teaching her, like, 10 years’ worth of knowledge in one month,” Kelly says.

This is fundamental to the sugar experience, Jim says. “When you read some of the traditional literature about sugar daddy–sugar baby relationships, one of the big attractions for young women is the mentoring aspect. That sounds trite until you experience it. It is actually one of the more valuable parts of the relationship to the young lady. And it’s fun for us too.”

Of course, the lessons extend to sex. They don’t go into detail about this, but Jim gives a hint in a smile that speaks of satisfaction with a solemn responsibility properly discharged. “I can tell you, the next guy she meets is going to be much happier than the last guy she dated,” he says.

“I tell her things that maybe her mother should but would never,” Kelly says.

“We just don’t have, like, boundaries,” Jodie says. “I mean, in the eyes of society we’re all sinners; we’ve all just thrown our morals out the window. So everything’s just out on the table.”

Back in Boston, Jodie has a serious boyfriend who wants to marry her. She doesn’t feel she’s cheating, because they have a no-tell rule while she’s at school. But it would be the end if he ever found out. At the same time, she feels really close to Kelly and Jim. “Hopefully when I’m married and I’m older,” she says, “I’ll still keep in touch with you guys.”

At lunch the next day Jim finally gets a chance to tell his own story. He grew up relatively middle-class, he says.

“Jim’s version of middle-class is my version of upper-class,” Kelly says.

“We lived in a very middle-class house.”

“You lived in the nicest neighborhood in town.”

“No, no, no, we didn’t, actually.”

“He’s lying.”

Jim rolls his eyes. “Anyway, I was middle-class my whole life, but I was very happy.”

He ended up making millions in banking and marrying a beautiful woman who didn’t much care for sex. They had kids. She got depressed. Life turned gray. Counseling failed. Finally Jim felt he had two choices. “I could stay in the marriage and be miserable, or get a divorce, which I didn’t want to do for the kids,” he says.

A third choice occurred to him, but his wife caught him and initiated divorce proceedings.

Free at last, he was ready to fulfill his fantasies. A friend advised him to play the field, but Jim quickly found that a 50-year-old man with a taste for plaid was something less than a sex magnet. He went back to his helpful friend.

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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.