The First and Friendliest Finishing School For Transgender Women

(L) Donna came over to get made up but eschewed the party for a night flirting at a local bar for transgals and their admirers. ® Lady Ellen put the finishing touches on Donna before Donna headed out for a night of flirtation.

Photographs by Joel Barhamand for Yahoo Style

The short, stocky, early-middle-age man with the prominent nose and the thick Joysey accent looked a bit like a cross between a younger Sean Penn and Joey Pesci. But this snowy Valentine’s Day afternoon, he’d shown up at Ellen Weirich’s ranch house in suburban central New Jersey, with a tight black minidress, double-D breast forms, stiletto heels and long blond wig concealed in a gym bag. For this afternoon makeover session and house party to follow, he was determined to become “Michelle,” the bombshell he carries inside him.

“I’m feeling a lot of emotions,” he said, as Weirich—known to her clients as Lady Ellen, the energetic proprietress of the decade-old Le Femme Finishing School, which teaches men how to dress, walk, talk and otherwise act like ladies—applied a thick coat of theatrical foundation to his freshly shaven face, then put a black wig cap over his head and taped it to his forehead to give his eyebrows a coquettish arch. “This is very thrilling. Dressing up like a girl is the most exciting thing I experience. When I first came to see Ellen, I’d never met Michelle. Now I keep bringing her out more and more.”

What was Michelle like? “She starts out quiet and reserved,” said the man, for whom the dinner mixer to come would be Michelle’s first time out in a social setting, “but she can get pretty wild.”

“I think she’s gonna be a party girl,” said Lady Ellen, a buxom, extroverted blond “G.G.”—that’s her abbreviation for a “genetic girl,” someone born a woman biologically—who’s been helping male cross-dressers and male-to-female (MTF) transgender folks externalize their inner gals ever since her teens, when she showed a guy she met at a gay bar in a bad wig how to pull “herself” together passably and walk in heels. She’s been doing it professionally since 2005, in addition to her day job at a home for people with autism and brain disorders. She doesn’t see the two professions as that different.

(L) Jeni said that in the past she’d dressed up as a woman for boyfriends. ® Kimberly wore a red floor-length with a light wrap for the Valentine’s mixer.

Said her husband, Kurt, an easy-going disaster specialist who’s perfectly at home in his Barcalounger among his wife’s clients, “She wants to make a difference and help people. She’s a very nurturing, caring, compassionate person.”

And not only does she do private hair, makeup, dress and posture consultations, she also throws the occasional party, like tonight’s, so that her clients—gay, straight and bi, young and old, single and married, closet cross-dressers and those who live openly and full-time as women—can mingle, share beauty tips and forge friendships amid a society that’s making gains in understanding gender nonconformity but can still be a hostile place.

(L) “Sometimes I think of my clients as my dollies, like doing hair and makeup on the Barbie head when I was little,” says Lady Ellen. ® A sign in Lady Ellen’s makeover room lets clients know they’ve come to the right place.

“I’ve met a lot of cross-dressing men who said initially they weren’t going to transition fully, then they did,” Ellen said, putting a bright red lip on Michelle, who’d insisted on it over a more subtle pale pink. “Often, they said they wished they’d done it earlier.”

It’s her job, she said, to teach them the hair, makeup and style tips they never learned, such as not to paint eyeshadow all the way to the eyebrow, not to join their lipstick at the mouth’s corners, or to wear long sleeves or an A-line dress, to deemphasize broad shoulders and straight hips. Biological women “had mothers or older sisters or friends to tell them they looked like a hooker or a clown, and how to do things right,” noted Lady Ellen. “My ladies did not.”

Lady Ellen said it was common for her newbie clients, who’d often been posing secretly in lingerie, to come in wanting to dress as provocatively as possible, regardless of their age or body type, and that she was tasked with helping them blend in with other women at the grocery store or the movies. Unless, she noted, her clients were determined to be sirens.

That afternoon, such was the case with “Donna,” a slim, bespectacled man in his sixties who came into Lady Ellen’s studio and swiftly changed into a corset, black bra, extremely tight leopard-print dress and sparkly gold platform heels. After Lady Ellen made up Donna’s face, she crowned her with Donna’s flowing blond wig.

(L) A slim, sixtysomething man gets into corset and girdle to become the blond bombshell “Donna.” ® Michelle applied press-on nails. “I’d love to do real nails for just one night,” she said, but after a night out, they’d give his cross-dressing away. 

“That’s the part that clinches it, when you put the wig on,” said Donna, who wasn’t sticking around for the party because she wanted to go flirt at Amanda’s Hideaway, a nearby lounge for transgals and their admirers. “That’s when I say hi!” Donna said she’d named herself for a hot girl she knew in high school, but that her Donna was “hot, friendly, not stuck-up. When you’re a guy and the pretty girls ignore you…” Donna sighed. “You don’t want to be like that.” Donna said she was merely a part-time cross-dresser. “I have no desire to become a woman,” she said. “It’s too hard.”

Donna was a secret to her wife and two grown kids. “It would be nice if my wife knew Donna, but I don’t think she’d approve,” she said. “And I don’t think I’ll ever tell my kids.”

“You’d be surprised how kids in their twenties would take it,” said Lady Ellen, using very light makeup to deaccentuate the cleft in Donna’s chin. “They just want to know that you’re going to stay their dad.”

That was more or less the case with Ally, 66, who started as one of Lady Ellen’s clients eight years ago—“She had a pajama party with hair and makeup,” recounted Ally, “which was so liberating for me because I realized I wasn’t alone”—but has since become so close to Ellen that she’d stayed over the night before to help set up the party. Ally, who calls herself bisexual, said she lived platonically with her second ex-wife, and that though her grown kids knew she was trans, she dressed as “their dad” when with them.

“I started out a fetishist, then became a transvestite, then transgender,” said Ally, who wore funky oval glasses, ballet flats and a simple black sweater and skirt over a red shell blouse. With her preference for a homey, dressed-down look, Ally called to mind Jeffrey Tambour’s role as the father of three grown children who transitions to a woman on the acclaimed new Amazon Prime series Transparent. “Those kids are horrible!” said Ally of the show’s self-involved progeny, admitting that, in a moment that echoes one on the show, her daughter once walked in on her in a skirt. “She didn’t really seem to register it,” laughed Ally, whose kids, overall, took her trans coming-out in stride.

She was most worried about telling her son. “He said, ‘I thought you were gay because you wore jewelry. But dad, it’s fine, I love you.’ He even knew that the risk of suicide for transgender people was really high.” Since coming out to her family, “I feel unburdened of a secret,” Ally said. “I could run into one of them at the mall and it would be okay.”

(L) Margaux prefers a tasteful, understated look, shopping at high-end stores like Bloomingdale’s and Saks. ® Lady Ellen has a large selection of pumps in generous sizes.

By 7pm, with most of the gals in hair, makeup and heels, and with shiny red Valentine’s heart balloons decorating the house, it was party time. The house quickly filled with about two or three dozen women from their twenties to their seventies, some of them dressed provocatively in body-tight minidresses and stilettos, some demurely in pearls and Nancy Reagan-type suits, some like cool young hipster girls in shaggy haircuts, minimal makeup and simple shift dresses. The ladies sipped wine and complimented one another on their hair, makeup and fashion.

Dressed like near-matching Raggedy Ann dolls were Carol and Stephanie, romantic cohabitants who are part of a subgenre in the cross-dressing scene called “sissies”—those who rebuke childhood bullies by dressing up in adulthood just as frilly, flouncy and girly-girl as they please. The duo said that they dressed this way all the time and were roundly accepted in their New Jersey town.

“If I’m not in my dress when I go to Shop-Rite, the clerks give me holy hell,” Stephanie said.

(L) Allison (left) told wife Cilla that she liked to cross-dress before they married, and Cilla’s gone along for the ride—not always happily. ® Donna insisted on the tallest, spangliest heels imaginable. 

In another corner, somewhat shyly, sat Allison and her biological (or “cisgender,” to use a newish term for non-trans people) wife, Cilla, who’d left their two school-age boys with a babysitter and driven two hours in secrecy for the party. Allison, a service member turned attorney, looked a bit like a tall female Texas Republican with her carefully coiffed blond wig, tanned and made-up face, sleeveless red silk dress and tasteful costume jewelry. Cilla was considerably plainer in a black sweater and slacks. Allison and Cilla had met and fallen in love 25 years ago, at which time Allison, who’d prior only presented to Cilla as a man, disclosed her woman side to Cilla.

“I liked him a lot by that point,” recalled Cilla, “so I was willing to see what it was all about. I worried for a long time he was gay, but the longer we were together, I saw that he wasn’t.”

How so? The sex, she said.

Also, said Allison, “I would say guy things.”

“Crude Beavis & Butthead humor, like he has with our sons,” said Cilla, adding, “If she’d waited to tell me about Allison til after we got married, it might not have gone down so well.”

Absolutely nobody knew about Allison, they told me, except for one other cross-dressing husband and his wife whom they socialized with. For years, Allison had been content to dress as a woman around the house when the kids weren’t around. But in the past year, Allison had been “going out,” socializing with transgals and other cross-dressers at clubs and mixers like this one, and Cilla was feeling left behind.

“It used to be just us binge-watching Breaking Bad on the couch,” Cilla said. “Now she’s always going out to clubs and karaoke nights and I’m like what?” Sometimes Cilla accompanied Allison to trans events, like tonight. “But I felt like a wallflower,” she said. “I’m most comfortable when Allison stays home dressed up.”

Cilla said she worried that Allison was moving toward sexual reassignment surgery.

“I think I’m transgender but I don’t want to go through with surgery,” Allison assured her.

Cilla shrugged, acknowledging that the situation was complex. “He’s still the guy I met and fell in love with. It’s like being gay—you’re born this way.” And she admitted that marriage to Allison had its perks. “She buys me beautiful gifts from Yankee Candle, not like other husbands. This makes him a thoughtful, more sensitive guy.”

(L) Lady Ellen put a sign up outside to let the gals know that makeovers and merriment awaited inside her New Jersey ranch home. ® Susan and Margaux chatted the night away.

The party never got too raucous—indeed, it seemed that Ellen had trained her clients well to behave like ladies. Michelle, pleased with the approving remarks she’d been receiving all night, said she was contemplating driving home as Michelle—not dressing back into man “drab,” as she usually does. “That’s exciting to think about,” she said.

Around eleven o’clock, some of the ladies put on their wraps while others went downstairs to change back into man drab for the drive home. Hugs, kisses and cell phone numbers were exchanged. Some said they’d see each other next month, at Ellen’s bash for St. Patrick’s Day.

“Valentine’s parties are especially important to me because I hate for my friends to be sitting home alone,” Ellen said, collecting plates and cups. “I love watching girls who arrived as total strangers kiss and hug goodbye at the end of the night. It makes me feel great to help them find a place where they feel at home.”

(L) Ellen’s longtime friend Veronica cooks the buffet spread. ® Cards Against Humanity was on offer but was ignored amid the night’s chatting and nibbling. 

Photographs by Joel Barhamand for Yahoo Style.

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