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Beauty and glamour became less elusive when Kai joined Seeking Arrangement.com, an unconventional dating site where moneyed older men, “sugar daddies,” pay for companionship and sex with young men and women.

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Seeking Arrangement launched in 2006 as a passion project for founder and CEO Brandon Wade, an MIT graduate who couldn’t get girls to go out with him.

On other dating sites he was “outgamed by guys who had good looks or amazing bodies,” Wade once told me.

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But beauty, glamour, femininity—achievable through hormone therapy, breast augmentation, and gender reassignment surgery—were elusive for Kai, who was 16 when his mother and stepfather kicked him out of their home in Hollywood because he was gay.