With the emotional support of Hollywood and the financial ballast of the Kardashian and Jenner fortunes, Bruce transitioned to Caitlyn, an exceptionally beautiful and glamorous woman.
Five years earlier, Kai, an 18-year-old Laotian boy, was fantasizing about his own transition.
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.
He struggled to finish high school and find a steady job.
Beauty and glamour became less elusive when Kai joined SeekingArrangement.com, an unconventional dating site where moneyed older men, “sugar daddies,” pay for companionship and sex with young men and women. Instead, Kai found benefactors who wanted to help him become a woman.
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. “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.
The slang term for rich older men was popularized in the Roaring ’20s and immortalized in Gentlemen Prefer Blondes, the 1953 film starring Marilyn Monroe as Lorelei Lee, the girl diamonds are the best friend of.
Lorelei and her friend Dorothy Shaw sing “Bye Bye Baby” to Lorelei’s sugar daddy boyfriend, Gus Esmond.
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.
Since its inception, the site has frequently been derided as an online brothel. Likewise for its promotion of antiquated, cheesy terms for its users.
Despite the criticism and controversy, it continues to be hugely popular—indeed, five years ago few would have guessed that Seeking Arrangement would be touted by members of the transgender community.
“Being a sugar baby was my life,” Natalie Lima, formerly Kai, said as we left the Glendale Galleria, a shopping mall where she works as a sales associate for Coach, the luxury retail brand. “My daddies helped me get back on my feet when society wouldn’t accept me.”
Natalie is 23. At 18, Kai began dating sugar daddies as Natalie. She hadn’t transitioned yet, but she wore women’s clothes and highlighted her naturally feminine features with makeup. She started hormone therapy a year later, paying some $400 a month in sugar daddy cash for testosterone blockers and estrogen shots.
2013 was an especially lucrative year for Natalie. She was juggling six daddies and “made $150,000, roughly $6,000 a month,” she said.
Most of Natalie’s daddies were father figures: They proffered advice and money over fancy dinners. Natalie even introduced some of them to her Laotian aunt and cousins (she stopped speaking to her mother, father, and younger sister when she left home).
A few daddies had other things in mind besides pampering.
Paul, who was in his early forties, asked Natalie to dress him up as a woman and do his makeup. “He was possessive, which I didn’t like. He’d tell me I was his only friend,” Natalie said.
She insisted she’s never had a sexual relationship with any of her daddies.
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.
There, Natalie talked briefly about her family. Her parents immigrated to the U.S. from Laos in the early ’90s, settling in Los Angeles, where they worked in clothing warehouses.
Natalie’s father left her mother when she was younger. He was abusive and into drugs. Natalie recently found his mug shot on the Internet: He’d been arrested for blowing up a meth lab. Her mother remarried.
Natalie and her friends used to dance at gay nightclubs. When she became a woman, she called herself “Natalie” after Natalie Mejia, the former lead singer of Girlicious, an R&B band.
She liked “Lima” for a last name because it “sounded nice with Natalie and also vaguely Asian.” She has a dancer’s body: petite, with lean legs, a muscular butt—
“And no boobs. I want to transition fully, but I’m not the type of person to prioritize getting a boob job over having a home and a car. I have tranny friends who are like that. I need to make enough money to buy myself time to heal! 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.
Girly Natalie giggles when she talks about anything sexual. The flesh on her cheekbones puckers when she laughs, often at her own silly jokes.
She wears long black hair extensions and loves doing other girls’ makeup (she learned to do her own by watching YouTube videos). She shows you she’s vulnerable.
Fierce Natalie takes herself very seriously. She is stubborn about her convictions, like her New Age beliefs about moving and sensing energy. (“I can see visions of your darkest times,” she told me, “like when someone in your family died or when you were going through a breakup.”)
Fierce Natalie says “yes” instead of “yeah” and gesticulates when making a point, drawing the triangular tips of her fake fingernails together in front of her chest. She pretends she’s not vulnerable.
“When I first started the sugar baby stuff I came to understand how I wanted the world to perceive me. I wanted to be a woman who was classy and intellectual. She’s very smart about how she goes about her life,” she said, referring to herself in the third person.
On a website where sexual transactions are frequently part of the pay-to-play arrangement—a tacit agreement if not a predetermined one—I asked Natalie, somewhat skeptically, how she’s managed to avoid this part of the deal.
“I lay it down for these men. I tell them that I’m transgender, and that I just want to have a stepping stone in life that my parents couldn’t give me. They respect that I want a career. I’m not a piece of meat. When it comes to being a woman and having the strength and power to be yourself, you should never have to do anything in return. Never.”
Ryan used to be skeptical of Natalie’s avowed sexless relationships with her sugar daddies.
“I said, ‘There’s no flippin’ way these men are paying you to just be yourself.’ I didn’t believe it until I had a daddy myself.”
It was Friday night and Natalie’s friend, Charles, was visiting for the evening, sitting on her bed while Natalie powdered my face.
We were going to The Abbey, the popular West Hollywood gay bar, and an occasion that called for cat-eye makeup, fake lashes, and a face lacquered with concealer. (There, men and women would paw at Natalie from every direction as she ticked toward the bar on her heels.)
Before we left for the night, I learned that Charles, 26, began transitioning five months ago.
“We put him on a six-month plan for now,” Natalie said, plunging her brush into a pot of bronzer.
Charles still looks very much like a young man. He was dressed in SoCal skater uniform: baggy jeans, an oversized plaid button-up, and a black, flat-brimmed baseball hat. Only his friends know that he’s transitioning.
He lives with his parents in Corona, southeast of Los Angeles, and has a job making paint samples for a paint manufacturer in Ontario.
“I’m trying to get a corporate position, and as soon as I do I’ll move out of my parents’ place and will start fully transitioning outside of work,” he said.
The plan is to save up $16,875 for gender reassignment surgery in Taiwan, a package deal that includes setting patients up with a new passport, new ID, and a three-week recovery period in a resort setting.
Afterward, Charles will begin applying for corporate jobs as “Chiara.”
“I’ve always felt like I was a girl inside, since I was very young, but I’ve always been attracted to girls, too,” Charles said, although he’s recently experimented with men, including older sugar daddies on Seeking Arrangement, after his longtime girlfriend cheated on him with his best friend. (“I thought I was going to marry her.”)
Natalie joked that Charles went on Seeking Arrangement to work out his “daddy issues.” He wasn’t interested in their money, but older, experienced men intrigued him.
“I’m so used to taking care of everything on dates, so it was nice to have it be the other way around,” said Charles. He hooked up with a few of his daddies (“mostly kissing”), but was shy because he hadn’t been with many men before.
“It was a dominant-submissive kind of thing,” he said of being a sugar baby. He would sit in the passenger seat of his daddies’ convertibles—Mercedes, BMWs, Audis—as they cruised out to Malibu or Laguna Beach after dark.
“Some were pretty aggressive and kind of all over me, but the few other times I’d been with men I was the submissive one anyway, so I just let them do their thing.”
In Los Angeles, where traffic is as reliable as sunshine, driving from one end of the city to another is a miserable, stop-and-start ordeal.
Driving around Malibu, however—just northwest of the city—is a thrill ride of precipitous turns and cliffside views, particularly when your destination is a modernist mansion teetering over the Pacific Ocean.
And so it was for me when I visited the home of a multimillionaire Malibu sugar daddy, Mark (not his real name), who is 59 and has his own commercial real estate business.
Mark had his first date with a sugar baby a year and a half ago, after coming out of several long-term relationships, including his 24-year marriage.
Now he dates women in their twenties and thirties, all of whom expect to be financially compensated.
“This has been going on for all of time,” Mark assured me about this type of arrangement. “Some women expect certain things from certain guys, and some guys expect certain things from certain women.”
Mark has tried meeting women on other dating sites like Match.com, but he prefers Seeking Arrangement because women are “a little more direct about what they’re looking for, which I like.”
We were sitting on cushions designed by Jean Paul Gaultier, arranged into a makeshift sectional couch in the living room area, sipping bottled Fiji water and looking out at the Pacific Ocean.
Physically, Mark reminded me of Bill Maher, if Maher had chin-length, silver-blond hair and accessorized his left ear with a diamond skull-and-crossbones earring by David Yurman.
He wore a short-sleeved, black-and-gray striped polo shirt with a small peace sign in place of the traditional decal. His reedy biceps were tattooed with floral and tribal designs.
“I’m open to everything, from hookups to weekly arrangements or monthly arrangements,” Mark said. “Some women want a traditional boyfriend.”
Mark was adhering to a very specific definition of “traditional,” meaning “old-fashioned,” though he didn’t spell it out as such.
“Normally if I’m in a long-term relationship I end up supporting my partner anyway. The difference is that you do the financial thing here first and then you see whether or not the relationship follows.”
Now Mark was opening up: The longest relationship he had been in with someone on Seeking Arrangement lasted a year, and it wasn’t exclusive. He’s met roughly 50 women through the website.
“I do normal date stuff with a lot of the girls,” Mark said, like dinners, movies, concerts.
Later that night, he and one of the younger girls he met on the site, a student, were going to Beverly Hills to watch the Christmas tree lighting on Rodeo Drive.
Mark doesn’t usually bring girls back to his house unless he’s seen them a few times. “A lot of these girls are financially desperate. They might take a look around…”
Installed on the wall behind the dining table was a monochrome plank by the late, minimalist sculptor John McCracken, whose works go for hundreds of thousands at auction; one of Dale Chihuly’s large acrylic paintings hung in the foyer.
Not that Mark’s sugar babies would walk off with his art, though they might go for a Gaultier cushion. But everything looked absurdly expensive, including Mark himself.
Mark was happy to discuss his art collection, but squeamish when asked about figures, like his net worth. This quickly became a guessing game: tens of millions? Hundreds?
“Somewhere in that range,” he said meekly. He ultimately confessed to spending roughly $50,000 on sugar babies since joining the website.
The average sugar daddy in Los Angeles has a (self-reported) net worth of $12.1 million and spends $5,010 a month on his sugar baby. Mark, if he was telling the truth, spent less per month than the average daddy.
“The biggest turn-offs are the professional sugar babies,” Mark told me. “They’ll try to play you. They’ll say, ‘I don’t want to see anyone else but you.’ They think that at 25 they’re going to pull the wool over my eyes, but it’s not going to happen.”
Once, a girl messaged Mark on the site and asked if she and her friend could come over.
“We ended up having a threesome, and then they asked me for money when they were leaving!” Mark said, laughing in disbelief. “What am I supposed to do? Give you a hundred? Five hundred? A thousand? Even an escort would say what they charge up front.
“It doesn’t happen often. Most people, surprisingly enough, they want something somewhat meaningful. They don’t want to feel like prostitutes.”
Mark, ever the gentleman, showed me out the door. Down the road, his gunmetal gray Lamborghini coughed and sputtered as he passed me on the highway, racing toward Beverly Hills.
I met Giovanni (“Yanni”), another sugar daddy, at his home in Anaheim, about an hour southeast of Los Angeles. It was decidedly less chic than Mark’s house in Malibu: a gaudily decorated but cozy place that reflected Yanni’s Italian-Greek background.
Yanni, 58, was eccentric and chatty, with candid, cornflower blue eyes and an animated, handsome face.
“Seeking Arrangement is not for escort service,” he said in a heavy Greek accent, rolling his Rs. “If I want a one-night stand I’ll go to the nearest parlor. I don’t need that. Seeking Arrangement is a dating website and it’s been working amazingly for me. I’ve met so many nice people and so many trash people.
“Most of the girls in their twenties are druggies. They ask me, ‘How much are you going to pay me?’ So I play dumb: ‘Pay you? What for?’ They look at me like I’m crazy!”
“Crazy” came out as a whisper, with Yanni smiling big and shaking his head.
Wade and other reps for Seeking Arrangement have stressed that the site kicks people off who are using it as an escort service.
Yanni applauded their efforts. One woman who had offered him oral sex for money was removed from the site a day after he reported her.
Yanni is a chemical engineer and designs airplane cockpits for Boeing, though he no longer works full time. He owns a Greek restaurant in San Pedro that provides a steady income and “gives me enough for my living.”
Twice divorced, he joined Seeking Arrangement two years ago. Unlike Mark, Yanni mostly dates older women on the site—thirties and forties—and almost always asks them to come to his house before he takes them out.
“Every time they come they are full of gifts. They bring me a lot of candles.” He stood up from the couch and walked around the living room and dining area, pointing them all out to me. “They’re beautiful girls, too! If they are not beautiful I’m not going to talk to them.”
Yanni doesn’t want sex for money—not exactly. He wants a romantic relationship and a connection with someone—“sex included, vacations included”—that lasts at least a few months. Ideally, he’d like to fall in love, but he isn’t overly optimistic.
“Let’s get to the bottom here. Women who are in their thirties and forties—if they’re beautiful and not married, something is wrong,” he said, lowering his voice again. “They have a baggage of sorts, or a bipolarity, if you will.”
Yanni did not strike me as mentally unstable, like some of the sugar babies he’d been with, but he wasn’t shy about valuing women’s looks above all else. He was evidently bored and lonely, so much so that he preferred amusing himself in the company of “trash” for several hours to no company at all.
He boasted, as Mark had, of the many young girls who are disingenuous and “think they can fool you. They cannot!”
Yet Yanni has been fooled.
“I have gone out with 100 or so women on the site, and after about a month, 90 percent of them have called me up and said, ‘Yanni, I need money for rent. I need money because my car is being impounded.’”
Yanni wasn’t evasive about his net worth ($1.5 million to $2 million) or the amount of money he has spent on sugar babies (more than $30,000 altogether; $1,000 a month “at a minimum”).
“But I enjoyed it too,” he said. “The dates, the sex afterwards, the companionship—that also pays off.”
Yanni wasn’t interested in arrangements with women young enough to be his daughter, but he was especially turned off by those who tried to whore themselves out.
Indeed, a crucial component of the “sugar baby” fetish for older men is that she’s something of an ingénue, an energetic young thing whose affection may well be for sale.
That certainly seemed to be the case with Isabella, a 21-year-old sugar baby in Los Angeles whom I spoke to on the phone after returning to New York.
There was something refreshingly honest about her admitting that she had no desire to work or do anything in life but “vacation full time.”
In June, she and her friend decided to create profiles on Seeking Arrangement “as a little joke,” she told me. “We were like, ‘Let’s quit our jobs and find a rich guy to pay for everything.’ Why the hell not?”
Within a month, she was dating a plastic surgeon in his late thirties from Beverly Hills (“he does all the celebrities and stuff”) and collecting a weekly allowance of $1,500 in cash.
She immediately quit her job as a veterinary technician and never went back. They’ve been “together” for nearly five months now.
“He has two maids, a chef, and a gardener who all live on site, but I still go over and surprise him with cute little dinners,” she gushed. “I crashed his Ferrari into his Rolls-Royce and he wasn’t even mad! He was amused, actually.”
On top of her allowance, she shops online with his credit card whenever she’s at his house.
“Now that we’ve built up trust, I go over my allowance a lot. You can’t really buy a new purse with $1,500 a week.”
The sex is really good, too: “He’s very attentive, very patient, very dedicated to me.”
Another perk of Isabella’s life as a sugar baby: “I’m always out elbow-to-elbow with celebrities—Lil’ Jon, Joe Jonas, Gigi Hadid. You enter a really exclusive world that most girls don’t have access to.”
Isabella has her own connections to the entertainment industry (she starred in 11 episodes of a reality TV show on Fox “before leaving to permanently be on vacation”), so she said she knows a lot of celebrities anyway. But her sugar daddy knows more.
She said she’s still under contract with Fox and could go back to work if she wanted to. “It was fun but I enjoy vacations more. Who doesn’t like beaches and martinis?”
Somehow, she still manages to attend the occasional class at a community college in Huntington Beach, where she’s in her third year with sophomore standing.
For all her candor, Isabella still felt compelled to distinguish between prostitution and sugar-babydom.
“Being a sugar baby is an exclusive thing,” Isabella said. “It’s not like you’re getting paid to show up by the hour. You have an actual relationship with someone.”
Then, perhaps reading the site’s promotional material, she concluded that Seeking Arrangement is “just a modern twist on traditional relationships.”
Isabella is very young and not very clever. If she wasn’t blessed with a “Victoria’s Secret body,” as she described it to me, she’d be less inclined to find her calling in sugar-babydom.
The young, ambitionless, and dim-witted have little incentive to work on anything other than their figures. Inevitably, when age starts working against them, their sugar daddies will have long ago found younger flesh to invest in.
No matter what motivated each of these people to seek out transactional relationships, almost all of them felt obligated to justify or qualify the sex-for-money aspect of their arrangements.
But their stubborn qualifications often made them seem out of touch, like they were lying to themselves.
I met Sara-Kate, 26, at a Starbucks in New York to hear about her adventures as a sugar baby in Los Angeles. In many ways she was the opposite of Isabella: bookish, down-to-earth, quietly pretty.
She’d grown up in Massachusetts, where she went to an elite, all-girls private school and then to Tufts University. She didn’t have boyfriends in high school, let alone drunken hookups, though the latter was more appealing than dating at Tufts.
Meanwhile, her gay best friend was meeting older guys on Grindr and jokingly encouraging to go “husband hunting” on Seeking Arrangement.
“I associated sugar daddies with shopping sprees and expensive dinners. Then I hooked up after my first dinner date during senior year,” she told me.
When her date dropped her off and handed her cash, she hesitated.
“Getting $500 for a blow job was completely foreign to me. I walked into my apartment and freaked out in front of my roommates. I was like, ‘You guys…’ It was the easiest money I’d ever made!”
She went out with a handful of sugar daddies when she was still at school. She fellated a 75-year-old man. (“He was lovely.”)
A month after graduation in May 2011, she started a job placing Chinese high school students in private schools around the country. She’d just returned from a week in New Orleans with one of her daddies, who paid her $5,000 for the trip.
She quit after less than a week at her job and spent the rest of the summer living on her own in Concord, Massachusetts, aimless but independent—and obsessed with saving money. By the middle of August, she was involved with 20 daddies in the Boston area.
Sara-Kate spent the next few months living at her grandparents’ in Westchester, New York, rehearsing to be in an off-Broadway play in Manhattan and spending weekends at The Plaza with a new sugar daddy.
By October, she’d saved $25,000—more than enough to cover living expenses and comedy classes in Los Angeles.
“I moved to West Hollywood and had all this free time on my hands, so I started building relationships with new daddies.”
There were a lot of pretty young girls in L.A., which made her more determined to seduce as many daddies as she could.
She would end up juggling nearly two dozen of them and had sexual relationships with all but one, a 67-year-old man named Michael who wore a skirt on their first date and had a cross-dressing alter ego, “Michelle.”
“It was a novelty, so I told him come over to my place next time in full Michelle mode,” she said. “When he arrived in the trashiest clothes, I was like, ‘Michelle!’ Every time he came his self-tanner would get all over my rug. But he paid me $500 an hour, so…
“In L.A. I felt like I was in my own little world with no consequences. I would ask myself, ‘What is the least amount of time I can commit to these men and the most amount of money I can make?’ I’d always get this little high afterward.”
Sara-Kate would usually meet new sugar daddies in a public place, then invite them back to her apartment. Sometimes they would go to the Beverly Hills Hotel or the Beverly Hilton. Grinning, she noted “a few random little hotels, off the highway.”
Sara-Kate squirreled away $80,000 during the two and a half years she lived in L.A. By last fall, she convinced herself she was losing brain matter.
“I was being myself around these men, which was good for me, especially since I didn’t know how to interact with guys when I was at Tufts,” she told me. “But I wasn’t intellectually stimulated or fulfilled out there.”
She decided to use the money to pay for grad school. She’s enrolled in an MFA program in creative writing at the New School in New York. She’s also working on a book about her life as a sugar baby.
It would be cynical to view this as another money-making scheme by Sara-Kate, though the book idea is a variation of the “Stripping My Way Through Medical School” memoir. If Sara-Kate’s story was bought by a big publishing company, money would be the end result.
After years of having sex for a living, writing about it may well provide Sara-Kate with a route to what many other sugar babies desire: independence, and their own material autonomy.