I can’t be going to work leaking from my vagina.”She covered her mouth and squealed—a high-pitched, infectious laugh.“The vagina is going to come next.”Natalie is both girly and fierce, playful one moment and a “boss bitch” like Nicki Minaj the next, with similarly full lips that she paints electric purple.Anna Nicole Smith and Hugh Hefner’s many Playmate girlfriends are famous in the real-life annals of gold digging.Seeking Arrangement was created as a dating platform for wealthy men like Wade, and for women eager to plunge their hands into a man’s deep pockets.Girly Natalie giggles when she talks about anything sexual.
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.
A few daddies had other things in mind besides pampering. She insisted she’s never had a sexual relationship with any of her daddies. Natalie’s father left her mother when she was younger. Natalie recently found his mug shot on the Internet: He’d been arrested for blowing up a meth lab. Natalie and her friends used to dance at gay nightclubs.
Paul, who was in his early forties, asked Natalie to dress him up as a woman and do his makeup. We were driving from the mall to her apartment complex in Glendale, a large stucco building where Natalie shares a modest two-bedroom apartment with her boyfriend of two years, Ryan; her best friend, Nick; two cats, Athena and Venus; and a black-and-white Pomeranian named Charlie. When she became a woman, she called herself “Natalie” after Natalie Mejia, the former lead singer of Girlicious, an R&B band.
On other dating sites he was “outgamed by guys who had good looks or amazing bodies,” Wade once told me.
“My mother always told me to focus on school and study—don’t worry about the women; they will come when you’re successful because then you have the means to be generous.”Sugar daddies are nothing new, of course.