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July 9, 2010

How to Nab a Sugar Daddy

Holly Hill loves sex, wanted money, and had a plan. This is her story of becoming a professional kept woman and how she managed to get four men to pay her way.

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A few years ago, Holly Hill left her job as a psychologist in Sydney, Australia, at the request of her married investment-firm-owner boyfriend, who wanted a full-time mistress. Everything was AmEx black cards, La Perla underwear, and hot sex, until her lover got the guilts and went home to his wife. Hill was left with a broken heart, a half-written novel, and a mortgage she couldn't afford — but she had figured out where her true talent lay. She took out an Internet ad: "Attractive, professional, well-spoken, well-dressed 35-year-old woman seeks sugar daddy," it began, counting among her selling points her listening skills (thanks to the psych background), charm (a stint in PR), "discreet" parking under her building, and love of sex. She set her rate at $1,000 a week, and six months and four wealthy guys later (she interviewed more than 30), the novel was ditched in favor of a memoir, Sugarbabe. Now retired and in a not-for-profit relationship, Hill told us what it's like to be a kept woman — and what it'll cost you.

MC: What does it take to be a sugarbabe?

HH: I think 40 is an ideal age, because most men who can afford to keep a woman are older than that. They're successful, they've got time on their hands, and the last thing they want is for a waiter to say, "Oh, you've brought your daughter! How sweet." You don't have to be beautiful, but you do have to be confident and sexy. Don't spend money on lingerie — they just rip it off. And stick to a classic bikini wax. Most older men are shocked by the porn-star look. Bring wine on the first "date." Sugar daddies tend to be nervous.

MC: You're an educated professional. How do you rationalize this lifestyle?

HH: We all sell ourselves — whether it's our bodies, our brawn, or our minds. Selling a quality product is empowering when you get a lot of customers. And I had offers from dozens of men.

MC: But how is it any different from being a prostitute?

HH: Maybe I'm a sex worker, but by that definition, then so are women who only stay with their husbands for the weekly allowance. And at least I got to choose my buyers.

MC: You had four sugar daddies in half a year. If you're selling yourself as a commodity, wasn't it depressing to be "returned" so often?

HH: I didn't take it personally. They just wanted to spoil themselves with me, and spoiling isn't something people do for too long. If you have a treat all the time, it stops being a treat.

MC: Your dad cheated on your mom, and it made her miserable. How could you do this to other women?

HH: This is why I ultimately stopped. I realized that cheating isn't about sex; it's about lying to the person you love. I didn't like being a part of that. If I were to do it again, I would get the wife's permission.

MC: Do you really think there are women who would knowingly let their husbands pay you to be their mistress?

HH: I know there are women who let me have sex with their partners, because my boyfriend and I practice negotiated infidelity. And I always make a point of saying, "Thanks for the loan," and try to return my lovers better than I found them.

MC: "Negotiated infidelity"?

HH: Men are geared to be sexual creatures. If we force them to be monogamous, we're not using their biology to our best advantage, and we're going to be vulnerable. But negotiate with a man, and it makes you powerful. If he goes to a strip club, maybe you get a new handbag or frock. It's about working with nature rather than against it. It's about not being the girl who sits around wondering why he's late getting home from the pub again.

MC: But can't we buy our own handbags? Aren't your assumptions retro?

HH: What's retro is how we demonize selling sex. Why, why is selling one's vagina so very bad? It's so screwed up. Besides, my handbags are worth more to me than a lay. [laughs]

MC: You are close to your young nieces. Do you consider yourself a decent role model for them?

HH: Yes! Teenage girls need to realize that nature makes young men under the influence of testosterone for the first time unscrupulous. If we continue to fight this, future generations' marriages are going to fail just as ours have.

MC: Not all marriages fail.

HH: But many do. And since we can't change the nature of men, we must change the nurture of women.

MC: You seem highly libidinous, masturbating between dates. Should less-frisky women stick to negotiated infidelity and great handbags?

HH: When I don't feel like sex but my partner is keen, I make it my exercise. Every time I move with him, I breathe out and clench my pelvis, like a Pilates move. I do that for an hour, and it serves as the gym! Would you really rather sit on a stationary bike?

MC: An hour?!

HH: Like I said, I try to return them to their wives better than I found them.


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