Life as Sara. What it’s like to be a transgender woman when you’re not Caitlyn Jenner

Life as Sara

What it's like to be a transgender woman when you’re not Caitlyn Jenner

Published on July 29, 2015

Seventeen days after Caitlyn Jenner appeared in airbrushed glory on the cover of Vanity Fair, Sara Simone woke up in her rented Alexandria bedroom and considered the tools at her own disposal: a $9 bottle of Revlon ColorStay foundation — “Mahogany” — a spritz of Paris Hilton perfume, a plunging black T-shirt showcasing the breasts she had patiently earned with hormones. Was the shirt too racy? Maybe. But it was better, she’d decided when she transitioned four years ago, to have men stare at her chest than to have them scrutinize her face and ask whether she was a man or a woman. “Better they whistle at me than jump me,” she sometimes said, because in her particular existence as a transgender woman, catcalling seemed the lesser and safer of possible indignities.

Sara added a set of false eyelashes, one retrieved from the carpet where it had escaped. Two tan hormone patches, one for each buttock.

She slid gold sandals onto her feet, a gold ring onto her toe, and onto her lower half, a pair of snug neon pants which she planned to keep in rotation “as long as my legs can pull it off.”

“Pretty cute,” she declared, clipping back her long hair before heading into a world she was still learning to navigate, which was still learning to understand her.

There had never been a more visible time to be a transgender woman in the United States, but the visibility was mostly focused on the story lines of a privileged few. Glamorous Jenner, with her expensive stylists and a reality show documenting her transition. Bodacious Laverne Cox, the main reason Sara watched “Orange Is the New Black,” an actress who posed on red carpets in designer gowns.

Sara’s bedroom was lacking in designer gowns; it was, for that matter, lacking furniture. Her clothing sat in folded piles around the perimeter, a sheet on the carpet was a makeshift bed until a mattress could arrive in a few weeks. She was broke. In her 50s, she was “rebuilding,” after a chaotic span in which she lost a job, lost relationships, lost use of the sputtering pickup where she’d slept when she was too tired to keep looking for dingy motels. Her previous apartment — gone, after Sara determined that if it came down to spending $300 per month of her dwindling savings on testosterone blockers and estrogen, or putting the same amount toward housing, it was the pills and patches that were, she said, “essential and lifesaving.”

On Facebook, she railed against these setbacks to her friends, ruefully but not without optimism, noting that her experiences were shared by so many of the transgender women whose stories she’d heard. They also reflected the academic research: Transgender people were four times more likely than the general population to live in poverty (“Riddle me this, Batman; [I] have this donated canned food, but no microwave,” Sara lamented in 2012). They disproportionately experienced work and housing discrimination (“My butt will be hooking before I go through the homelessness crap again,” Sara wrote). Sixty-four percent of transgender people, in one comprehensive survey, reported being sexually assaulted. (“This man tried to destroy me, but he didn’t destroy me,” she said in a Facebook video, after ending a relationship with a man she says attacked her.) At her lowest point pre-transition, she’d considered suicide, picturing swerving off the road and only stopping herself because she needed to give someone else a ride home.

“I am very, very lovable,” she shared with her online community one day, after realizing her updates had been a string of bad news. “I am not a loser. I am lovable.”

Note: Clockwise from top left: From top to bottom: Sara Simone picks up a box of hormone medication in her bedroom at home in Alexandria, Va.; she curls her hair at home; Sara waits for her chicken and rice to cook in her kitchen.

Sara had clarity on one thing: She was happier now than she ever was in the decades she lived as a man. Her physical transformation ended years of anxiety and depression and felt “like celebrating Christmas every morning.” In the past few months, she’d re-collected, one by one, the items that she’d previously lost: a car, courtesy of some financial help from a friend; a new living situation — the Alexandria ranch house shared with two Craigslist roommates — and a job, at a Washington nonprofit where her co-workers hung pro-LGBT signs on the walls.

But the happy life was one that required Sara’s hard work, navigating a society that could still feel unfriendly, every day. Carefully applying makeup before leaving the house. Carefully monitoring the pitch of her voice, the cross of her ankles, the height of the shoes worn with her 5-foot-9 frame. She documented her attention to appearance with daily selfies from the same precise angle — a tilt of the head, a feminine dip of the chin. Careful and controlled, because she wanted to make sure the world recognized her as the woman she had become, and this was the goal, morning after morning, every moment of Sara’s new life.

Later in the afternoon, Sara set out to complete her main errand of the evening: buying a pair of eyeglasses with the insurance from her new job.

“Date Of Birth?” asked the form that the optometrist’s receptionist handed her. October, Sara started writing, in a time some 50 years ago, before “transgender” meant anything, when what she knew of gender was that the girls in her Pennsylvania middle school were developing curves and she was perplexed as to why she hadn’t developed them, too. A 10-year stint in the Army — “the most macho culture ever” — hadn’t changed those feelings, a five-year relationship and marriage to a woman hadn’t changed them, tense conversations with her mother and sisters hadn’t changed them, and four years ago she’d finally decided nothing would change them and went to Wal-Mart to buy a set of women’s clothes.

“Sex?” the clipboard prompted. Legally, she was female, having arranged a letter from a therapist that would allow her driver’s license designation to change from “M” to “F.” She hadn’t been able to afford genital surgery, but she saw no need for anybody besides prospective romantic partners to be concerned with that. Her sex drive was lower since she’d transitioned, anyway; what she wanted more than anything was someone to cuddle with.

“Do you wear glasses on a regular basis, ma’am?” asked the optometrist, leaning in to examine her eyes. He appeared to be of Asian descent. When Sara was “clocked” as transgender — an increasingly rare occasion — it tended to be by other African Americans. There was no surefire way to predict when it might happen, though, and as a result Sara went through a lot of her life feeling prepared for the worst.

Photo Gallery

A transgender woman learns how to be happy after enduring years of depression.

The long journey of Sara Simone. A transgender woman learns how to be happy after enduring years of depression.

“Which of these lenses is better for you?” the optometrist asked. “One or two?”

“One,” Sara said.

A few weeks ago, Sara went to dinner wearing a cocktail dress, her hair meticulously styled, and afterward she and a friend stopped at a hotel bar. While her friend went in search of a phone charger, a young white woman from the next table came over and demanded, Which are you, a man or a woman?

“Which is better?” asked the optometrist. “One or three?”


Sara hadn’t known how to respond to the woman at the bar. Some black ladies Sara was acquainted with possessed “this scary evil-eye thing,” the ability to wordlessly shame hecklers, but Sara made an effort to always appear demure and polite. “Why are you bothering me?” she asked finally when the woman wouldn’t leave.

She’d let her guard down that evening, having carefree fun, and so it hurt even worse when the mocking came. She’d been feeling so good about how she looked.

“Your eye pressures are excellent, Miss Simone,” the optometrist said, finishing the exam. “Awesome, perfect.”

Sara went next door to select a pair of frames, choosing a rhinestoned maroon pair and asking the clerk to check how much the insurance would cover. “I love your nails,” she told the clerk.

“They’re press-on,” the clerk confided. “You should get some!”

“They’re press-on?” Sara shook her head in admiration and, as she headed back to her car, passed a man in jeans and workboots. He stopped. He swiveled his neck. He cocked his head. He opened his mouth, and he let out a guttural growl of appreciation at the beautiful woman he saw walking to the parking lot.

Note: From left to right: From top to bottom: Sara dances with her friends Elizabeth Pavlesich, left, and her wife, Danielle Pavlesich, of Laurel, Md., at the Second Chance Saloon in Columbia, Md.; Sara removes her bright pink shoes at the bar.

Sara woke up and it was a bad morning, a shaving morning, which she disliked because of the fact that it was still occasionally necessary. “Definitely got some things here I need to get rid of,” she muttered, reaching for the razor, which she kept hidden so as not to risk questions from guests or from her housemates who, as far as she knew, were unaware that she was transgender. The housemates worked night shifts and kept to themselves; Sara only saw them in passing, which was fine with her.

Some nights when they were out, she allowed herself the freedom of puttering around in her underwear, but even when she was completely alone, she tried to never be completely naked. “If I am nude there is some ‘creative hiding of a particular part’ going on,” she explained to her Facebook friends, and such a thing became exhausting. It was exhausting, continually, to deal with having an appendage that was a part of her body but did not feel like a part of her being.

Each day was full of workarounds, creative solutions, polite responses to impolite questions. What did people mean, for example, when they asked her how she’d “known” she was a woman? Would a biologically born female be able to articulate a full answer to that question? Or what did strange men think would happen when they rubbed up suggestively on the Metro? Was this a common practice, and if so, how come she never knew men did creepy things like this when she lived as one? “I have a boyfriend,” she’d learned to tell them, though she did not.

This morning would include a staff meeting at the nonprofit where her job was helping homeless veterans find housing, followed by an intake meeting with one of those veterans. She picked through her clothing until she located a scalloped Ann Taylor top, reserved for when she wanted to look professional. She packed her always-heavy purse: golden jewelry. Pink bows. Lavender-scented lotion. A hand mirror with a long handle, which she carried everywhere. She’d acquired so many accessories as a woman. Some of them were about pampering, but some of them were necessary armor, protecting her from the men who would assault her if they knew she was transgender.

“Smile more,” she reminded herself as she combed her hair. “Giggle a little.”

Acutely aware of the military’s rigid masculinity, when Sara met new clients, she played up her most girlish traits.

“Julie from ‘The Mod Squad,’ ” she intoned now, summoning her favorite style icon.

Coffee, makeup, commute. Futzing with the GPS installed on her phone, which had somehow defaulted to Arnold Schwarzenegger’s voice, so that when she tried to turn it off, it said, “I’ll be back.” Inching up 395, remembering the early days of her transition, when her colleagues at an old job didn’t know she was transgender and she could only dress how she wanted during her drive to work. She would sneak to the bathroom to change into and out of women’s clothing. Back then, her fear of being discovered was the reverse of now. Before, the secret was that she sometimes dressed as a woman. Now, that she wasn’t born that way to begin with.

At work, the veteran introduced himself as Sara seated him at the conference-room table. She smiled. She scanned his intake form.

“You were in Panama?” she asked. She had been stationed in Panama during her own service.

The soldier nodded. “Two seasons there: wet and dry.”

“What years were you there?”

He told her the years, in the late 1970s. She had been stationed there during those years.

“What company?”

He told her the company. She knew it; it had been stationed next to her own.

Sara paused. She and the soldier might have old buddies in common, and that might have helped her bond with the client. But mentioning this would mean disclosing that those buddies knew her by a man’s name. Careful.

She cleared her throat. “I could help you revise your résumé,” she said finally. She didn’t mention Panama. She didn’t mention her own service. She smiled.

Note: Clockwise from top left: From top to bottom: Sara works for the Veterans Services Division of Friendship Place in Alexandria, Va., where a self-made display of other transgender women hangs above her desk; at her annual company picnic in Rock Creek Park in the District, Sara mingles with co-workers; after her co-workers had left the picnic, Sara remained at a bench with her computer and looked into her hand mirror, which she does frequently.

Lunch, meeting, commute back home. Work was gratifying, a piece of her life she reclaimed after the downward spiral that had initially begun pre-transition, brought on by the stress of trying to live as someone she was not. Her career was a through line in her life: She’d worked in social work for years, since leaving the military and getting a sociology degree. She liked the compassion in it; her new co-workers planned scavenger hunts and barbecues together.

Her personal life was sometimes lonely, though. She had family who was learning to accept her transition in measured doses but who, aside from her brother, did not call her “Sara.” She had good friends who she couldn’t afford to see as much as she’d like. Mostly she maintained relationships online, the place where she first learned how to transition. She’d initially tried just Googling “transsexual,” but “it was all just porn sites,” she said, and it took a while to fumble toward more helpful terminology.

Online is also where she kept a dating profile, her best hope for what she called “The Domestic Fantasy,” a lifestyle in which she would have a husband to cook for, and maybe he would have children, too. On her profiles, she’d decided to present her gender as a small facet of a full personality. “I am a pretty transsexual woman,” she wrote on one site. “I love cooking, camping, poetry, cuddling and long walks.”

Getting men to reach out wasn’t the problem; that evening when she got home, 13 messages had gathered since the last time she’d checked this profile. “What are you most likely to stay up all night talking about?” they wrote. Or, “Wink, wink.”

More difficult was getting a second message to follow the first. Most men who initiated contact did so without actually reading her profile. Once they figured out she was transgender, the ones who were still interested wrote to her as if she was a sexual conquest, something to be tried once rather than introduced to family.

“Going amazing, Honey,” she’d responded to the last decent-seeming man who asked her how things were going. He never wrote again.

Tonight, she switched to another dating site, specifically for transgender dating. There was still the chance her suitors would be after sex, but at least they would understand who she was.

A message from a suitor popped up. “Let’s go for a walk.”

Quickly, she clicked on his photo. “Oh, he’s athletic, that’s good,” she appraised. “And the water behind him, maybe he’s on a boat?”

Should she write him back? Given what she’d experienced so far? “Where do you want to go for a walk?” she typed in. “Along a serene beach or in the mountains?”

She hesitated just for a minute before pressing send.


Note: From left to right: From top to bottom: Sara, left, offers a big hug to Sydney McFadden of College Park, Md., at the Second Chance Saloon. When Sara was homeless, McFadden let her stay in her apartment; Sara, shown with Madelyn Keffer of Frederick, Md., roasts a marshmallow during the wedding celebration of Danielle and Elizabeth Pavlesich of Laurel, Md.

Sara woke up and it was a good day, a great day even, because the evening before she’d stayed out late with some fun co-workers who bought one another rounds of drinks, and because when she got home the suitor with the boat picture had written her back multiple times, and because today she had special plans to visit her brother.

She pulled on a short denim skirt and a black sweater and drove to a nearby Target, where on the magazine racks, Caitlyn Jenner was 20 days into her reign on the cover of Vanity Fair. “I think he’ll like this,” Sara said in the movie section, picking up a copy of the new James Brown biopic. Her brother had lived in a military nursing home since a traumatic brain injury left him unable to care for himself, and today was his birthday.

In front of the nursing home, an hour’s drive from her house, she pulled out her magnifying mirror, applying berry-colored lipstick and spritzing her neck with perfume. It was a 30-second walk between the front door and her brother’s room; those 30 seconds, lined with veterans in wheelchairs watching everyone go by, always made her nervous.

“Hey, big brother,” she said after knocking lightly on a door frame, to the man who was younger but dwarfed her in height. “How are you?”

“I’ve been watching this stupid thing,” he said, nodding toward the television.

“Oh, that’s Jim Carrey.” She reached up to hug him. “I got you something. For your birthday. I thought we could watch it tonight.” She produced the DVD and, because her brother now had trouble reading, she explained. “It’s the James Brown movie.”

“I love James Brown,” said the brother who had known her before she was Sara, who had loved her since they were children, around whom she did not need to be careful and controlled.

The picture came on. Instead of sitting with her ankles crossed, she leaned back on her elbows next to her brother, who sprawled in a similar position. He shimmied his shoulders along with the intro music, and so did she; he called out his favorite songs, and so did she. Before her transition and his injury, she often felt that their relationship was fraught. Filled with testosterone. Now it was a refuge, simple and tender.

“I love James Brown,” her brother said again as a dance sequence began.

“I do, too,” she said. “What kind of pizza should we order?” she asked a few minutes later, reading from a menu. “They have pepperoni, sausage, vegetarian — I like vegetarian.”

“You do?” He pretended to be horrified, pointing at the door. “Get out of here.”

“They have supreme. Hey, remember how we used to eat that? When we were little? Pizza Supreme from Pizza Hut.”

She picked up the phone to place the order — “Not a ‘sir’ — I’m a woman,” she said to the worker — and the movie finished, and Sara’s brother remembered an old tradition from their experiences in the service.

“I forgot to inspect you,” he said, beckoning her to stand.

“No!” Sara said, covering her face in embarrassment.

“Do you want me to make you do push-ups?”

“Oh, I can’t do push-ups anymore.”

“Weren’t you in the Army?”

“A long time ago.”

He waited, a demanding younger brother, until she sighed and slid to her feet. “Ready, salute!” he said. She raised her right hand toward her forehead, holding the pose for a second before collapsing in giggles. “Ready, salute!” he tried again, but she shook her head, laughing too hard to continue.

“Enough!” she said.

He laughed, and Sara remembered the birthday card she’d bought with the DVD. Her brother admired it before placing it on his bedside table.

“Do you want me to read it to you?” Sara asked. He nodded and passed the card back. “It says, ‘Happy Birthday,’ ” Sara read. “Love, your sister Sara.”

“That’s nice,” he said. “That’s good.”

“Come here and give me another hug,” she said when it was time to leave. They held each other tightly. Sara smoothed down her hair. She adjusted her skirt. She gave herself one last look in the mirror, to make sure her face was on right. She walked back past the veterans in the hall, into the late night, for the drive back home.

Lenny Bernstein contributed to this report.


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