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“Winks” from women showing their interest in his profile—some of them alarmingly attractive in a blow-dried Laguna Beach way—started rolling in at the rate of three to four a week. The woman can choose—and Boston emphasizes in his profile that he respects her choice—either “good clean fun,” like hand-holding and small kisses, or “friends with benefits.” Beyond the costs of the dates, Boston has helped with other expenses: an Ikea bed, a transmission, a Tiffany bracelet.

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Boston was intrigued by Seeking Arrangement, a website where so-called sugar daddies can connect with “sugar babies” looking to be pampered and paid on an ongoing basis, and Whats Your Price, where men bid on first dates with women who can accept the bid or demand more.

The site’s blunt pitch to women: “Get Paid to Date.” The more subtle appeal to men: Seeking Arrangement claims to have more than 40,000 female Bay Area members, compared with just 12,000 men. Boston makes a $40 bid for an initial coffee date or dinner to vet a woman for compatibility.

Three years ago, Boston seemed an unlikely sugar daddy.