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Taylor, a 22-year-old student at Hunter College, had confided in her roommate about the trip and they agreed to swap text messages during the day to make sure she was safe.
Once in Greenwich, a man who appeared significantly older than his advertised age of 42 greeted Taylor at the train station and then drove her to the largest house she had ever seen.
He said he lives next door in a penthouse apartment overlooking Central Park South and pays ,000 a month in rent.
But unlike other dating sites, where a user might also list preferred hobbies or desired traits, Taylor instead indicates preferences for a "sugar daddy" and an "arrangement" in the range of $1,000 to $3,000 a month.
Saddled with piles of student debt and a job-scarce, lackluster economy, current college students and recent graduates are selling themselves to pursue a diploma or pay down their loans.
"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 after taking a big hit in the financial crisis and being forced to downsize, Jack says he had to part ways with his private jet due to what he describes as "reduced circumstances." On the site, he lists his annual income as $1 million and his net worth as something between $50 and $100 million.