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On a Sunday morning in late May, Taylor left her Harlem apartment and boarded a train for Greenwich, Conn. She planned on spending the day with a man she had met online, but not in person.

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 changed into his swimming trunks, she put on a skimpy bathing suit, and then, by the side of his pool, she rubbed sunscreen into the folds of his sagging back — bracing herself to endure an afternoon of sex with someone she suspected was actually about 30 years her senior.

Taylor doubted that her client could relate to someone who had grown up black and poor in the South Bronx. While he summered on Martha’s Vineyard, she’d likely pass another July and August working retail in Times Square.

A love match it wasn’t. But then again, this was no ordinary date.

A month prior, faced with about $15,000 in unpaid tuition and overdue bills, Taylor and her roommate typed “tuition,” “debt,” and “money for school” into Google. A website calledSeekingArrangement.com popped up. Intrigued by the promise of what the site billed as a “college tuition sugar daddy,” Taylor created a “sugar baby” profile and eventually connected with the man from Greenwich. (“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. 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.

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