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"I only go out with girls 25 and under," says Jack, whose thick head of white hair and bushy eyebrows form a halo around a red, flushed face."But I can't walk into a bar and go up to a 25-year-old. So, this is how I go about meeting them." As he continues, he repeatedly glances over his shoulder to make sure no one is listening.While he summered on Martha's Vineyard, she'd likely pass another July and August working retail in Times Square. ("Taylor" is the pseudonym she uses with men she meets online.Neither she nor any of the other women interviewed for this article permitted their real names be used.) In her profile on the site, Taylor describes herself as "a full-time college student studying psychology and looking to meet someone to help pay the bills." Photos on the site show her in revealing outfits, a mane of caramel-colored hair framing her face."Most of these young women have debt from school," says Jack, who finds most young women also carry an average of ,000 in credit-card debt.

"I just wanted to get it over and done with as quickly as possible," recalls Taylor, forcing out a nervous smile.

"College students are one of the biggest segments of our sugar babies and the numbers are growing all the time." Wade rewards students who use a email address to register on Seeking Arrangement by automatically upgrading their free, basic membership to a premium membership, allowing them to send unlimited free messages and granting them exclusive access to the site's cadre of VIP sugar daddies.

The site also includes a complimentary stamp on student profiles, certifying them as a "college sugar baby." Wade sees his company as providing a unique service, a chance for "men and women living through tough economic times to afford college." He bristles at the notion that he's merely running a thinly veiled, digital bordello, choosing instead to describe his site as one that facilitates "mutually beneficial relationships." Taylor doesn't explicitly refer to what she was doing in Greenwich as prostitution, but she now allows that her primary motivation was, indeed, money.

But once on the train and no longer worried for her safety, she started to agonize over what she had just done. Jack isn't the name that appears on his American Express black card, but an identity he uses when shopping online for companionship and sex.

Jack says he meets up twice a week with a young woman from Seeking Arrangement.

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