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The Making of Maddie

Published Sep. 4, 2005

On a warm, sunny Thursday, just after lunch, Madalynn A. Shepley steers her wood-paneled van into the parking lot of the Clearwater driver's license office. She stops in an end space. Cuts the engine. Then she tips down the rear-view mirror to check her face.

She wants everything to be perfect for this picture. So she fluffs her brown bangs, pulls a compact from her purse, pats shimmery powder across her chin.

"They might ask me to remove my makeup in here," she says. "So they can have a true representation of this person who is supposed to be me."

Maddie is 38. Her shoulder-length hair is feathered in front. Her brown eyes crinkle when she laughs. She has broad shoulders, big biceps, slim hips. She's 5 feet 5, 175 pounds. She's wearing a soft red T-shirt and new red capri pants with white flowers.

"I'm even wearing Lady in Red perfume today," she says, laughing. "I bought it to celebrate. Oh, I've been looking forward to this day for a long time."

She pulls out her wallet and finds her driver's license. The photo shows a 37-year-old man with short brown hair, brown brows and serious brown eyes. A thick, dark moustache blankets his upper lip.

The name on the license says: Andrew Shepley.

Maddie has come to change that photo _ and that name.

"They could give me a hard time in here today," she says.

Doctor's orders

Maddie shares a Clearwater condo with her friend Nickie and a gray tabby cat named Booger. She repairs roller coasters and other rides at a Tampa amusement park she'd rather not name. She plays softball on Tuesdays, goes to a Metropolitan Community Church on Wednesday nights, listens to Styx and Rush, and makes a mean pot roast.

She was born a boy.

About a year ago, she moved to Florida and started taking hormones and calling herself Maddie. She had laser surgery to remove her moustache. She softened her voice and let her hair grow. She learned to walk in heels and appreciate salad and change her van's oil without chipping a nail.

She wants, more than anything, to blend in. To be just another woman out buying groceries, pumping gas. But sometimes, strangers stare.

She wants to become a woman so badly _ needs to, really _ that she gave up her wife, her four children and her house. She got fired from a job as an RV mechanic when she started coming to work as a woman. She lost almost all her friends. Her dad and her two brothers won't talk to her. Her mom keeps calling her Andrew.

She often feels alone.

But she's not.

An estimated one in 30,000 people is transgendered. Transgendered people have the mind of one gender, the body of another. They are divided evenly between men who want to be women and women who want to be men. They have existed throughout the ages, in virtually every culture around the world.

It's a psychological disability. It's included in the Diagnostic and Statistical Manual of Mental Disorders, along with depression, bipolar disorder and schizophrenia.

Transgendered people are born that way. There is no cure.

Doctors who treat transgendered patients usually prescribe hormone therapy, counseling and trying to live in the correct "brain gender."

But society doesn't always accept that. Many people don't want to see a man wearing makeup and women's clothing. They worry: Where will these people go to the bathroom? What if one of them wanted to live in my neighborhood?

About the time Andrew Shepley moved to Florida to become Maddie, the St. Petersburg City Council was revisiting its human rights ordinance. The law protects people from discrimination in employment, public accommodations and housing. Someone had asked the council to include lesbians, gays, bisexuals and transgendered people in it.

Council members told the lesbians, gays and bisexuals: We'll protect you.

They told the transgendered people: But not you.

"You are sending a message that transgendered people don't count," activist Jessica Archer told council members.

Maddie has never felt like she counted. Long before she worried about the picture on her driver's license, she knew she wasn't meant to be a man.


To almost everyone except himself, Andrew Shepley seemed like a regular guy.

He was born outside Chicago, the oldest son of a carnival owner. He grew up riding bikes, playing baseball and cheering the Cubs with his brothers.

Even then, he said, he knew.

One afternoon, while his brothers were playing catch in the back yard, he went inside, into his mom's closet. He fished through her laundry basket and pulled out one of her slips. He still remembers how sweet it smelled, how soft the fabric felt against his skin.

He draped the slip around his small shoulders. Then he pulled on a pair of her pantyhose.

"Oh, I was in heaven," he says. "I knew this was who I was meant to be."

He was 7 years old.

His mom caught him and told him never to do it again.

If only it were that easy.

Andrew didn't want anyone to think he was a freak. So he watched other boys and tried to imitate their mannerisms. He learned to swagger in work boots, to talk tough and swear. He lifted weights and built up his biceps. He learned to fix car engines and carnival rides.

He was a good actor, he said. But he couldn't convince himself.

Sometimes, when his family planned to go out, he would pretend he was sick so he could stay home. So he could try on his mom's stockings, put on her makeup, spritz her flowery perfume on his wrists.

When he was a teenager and other boys started bragging about the girls they'd been with, he would lie and tell stories, too. But he didn't date. Didn't go to his prom. Never had sex _ with anyone. Some people assume that transgendered people are homosexual. But sex has almost nothing to do with it.

The problem is how they see themselves.

One day, while Andrew was helping his dad set up a church carnival, he met a girl. The preacher's daughter. She was sweet and cute and had blond hair. Andrew was 20. She was 16. She was his first female friend. Maybe, he thought, this was love.

Maybe he wasn't so weird after all.

So Andrew married her. They had a daughter, then three sons. Andrew worked as a truck driver, an auto mechanic and on carnivals. During his 20-year marriage, he was never with another woman.

Except Maddie.

Inside out

"There are things, like getting married, that society says we're supposed to do," says Kathleen Farrell. She is a St. Petersburg therapist who holds a Ph.D. in clinical psychology from the University of Cincinnati. Since 1985, she has worked with more than 200 transgendered patients around the Tampa Bay area. She and Maddie meet monthly.

Most transgendered people desperately want to fit in, Farrell says, so they get married and have kids. Many transgendered men try to appear more masculine by joining the military, learning to hunt or ride motorcycles, taking jobs in construction or auto repair.

But they can't change what's inside.

Andrew's wife knew he liked to wear women's clothes. He often wore her underwear under his Lee jeans. Sometimes, he slept in her pale blue nightgown.

His wife usually tolerated it. "As long as I kept it in the bedroom," Maddie says.

But over the years, Andrew's obsession grew. He was feeling more and more like he had to be a woman. He started fussing at his wife, yelling at his kids.

"Andrew basically became a jerk," says his daughter, Stacey, 18. "We didn't know why Dad was so unhappy. We never saw him wearing Mom's clothes."

Andrew prayed for answers, asked God for help. He didn't want to do anything wrong. So he read the Bible, searching for scripture that said you shouldn't change your gender. Genesis, Exodus, Leviticus . . . he couldn't find anything. He couldn't take it any longer.

So on a cold Chicago morning, just after Thanksgiving, he called his children into the living room. Stacey and the boys, ages 10, 12 and 14.

"I'm sorry," Andrew told his kids. "I'm going to Florida. I'm going to start living my life as a woman."

Turning heads

Maddie's greatest fear is that she'll be "made." In the transgendered world, this means that someone notices you're not a biological woman. Some stranger stares or, worse, snickers.

Maddie has been taking three pills twice a day to suppress her testosterone and add estrogen. The medication costs $150 a month. Insurance won't pay for it.

It won't pay for sex-change operations, either. So she has been working overtime, trying to save $15,000 for the procedure.

She wants to get laser treatments on her cheeks and chin so she can stop shaving. She wants breast implants so she can stop wearing foam forms. She could get her Adam's apple shaved so it wouldn't stick out, her vocal cords altered to make her voice higher and have a couple of ribs removed to make her waist smaller.

But even after all that, she knows she still might get made.

"I have to face that," she says. "I try to be content with the best face I can present."

Right now, she says, she needs a new driver's license more than any medical procedure. She needs identification that looks like her, that has her new name, so she can cash a check, get a library card, rent a movie. Without giving herself away.

A well-groomed woman

After waiting almost 40 minutes, Maddie makes it to the front of the line at the driver's license office. A middle-aged clerk wearing bifocals is sitting behind the counter. "Can I help you?" she asks.

"I need to update my driver's license," Maddie says.

The woman slides her glasses down her nose, peers over them. "Do you have an appointment?"


"Well, is it for an address change?"

"Yes," Maddie answers. "And for a name change."

The woman behind the counter pushes up her glasses. She looks at Maddie through the lined lenses. "Do you have the court documents?"

"Yes," Maddie says, unsnapping her purse. She pulls out two pieces of paper. The first is a copy of the order signed by a Brooksville judge legally approving her name change. She chose Maddie because it's a combination of Mommy and Daddy. Because she feels like both to her kids.

The second paper is a letter from her therapist, Farrell. "To Whom it May Concern: Madalynn A. Shepley has been diagnosed with Gender Identity Disorder, which has been persistent since childhood. . . . Ms. Shepley presents as a well-dressed, well-groomed woman living full-time as a female since December 2001. To be consistent with this life change and for her on-going safety as well as her emotional well being, this letter supports the petition to the court for changing her legal name."

The letter also says the sex designation on Maddie's driver's license should be changed to female. "To be consistent with her female gender and her legal name change."

Maddie hands both papers to the woman behind the counter. The woman looks them over. Then looks Maddie over again. "This letter doesn't say that the surgery has been performed," the woman says, a little too loudly.

Maddie swallows. "It hasn't," she says. "Not yet."

The woman behind the counter leans forward. "Well, we can't change the gender marker until your doctor says you've been changed surgically."

By now, everyone in line is listening. Other clerks are coming over.

"So you're telling me," Maddie says softly, "that until I have surgery, I'm going to be walking around with a driver's license that has a female name and photo and a gender marker that says I'm a man?"

"Yes," the driver's license woman says. "That's what I'm saying."

Maddie steps back. But she doesn't turn around. The folks behind her in line are all looking, all buzzing about her.

The woman behind the counter calls over her manager. She shows him Maddie's papers. She points at Maddie.

The manager is Frank Head. He looks Maddie up and down. He speaks loudly, so everyone can hear: "Can I help you, SIR?"

Some people in line laugh. Maddie squares her shoulders. Tips up her chin.

"You mean Ma'am," she says.

"No, sir," says the driver's license official. "I don't."

Girls like us

Maddie often wonders whether this is all worth it.

She misses her kids. She's seen them only once this past year. They call her Mom now. "Some of my friends think it's strange. But I say, "Go ahead. Whatever makes you happy,' " Stacey says. "I know since this change, she's not as uptight or as quick to fly off the handle."

Maddie's ex-wife has remarried. She wants her new husband to adopt the kids. "She thinks I'm a Jerry Springer show or something," Maddie says.

Maddie misses her friends in Chicago, her brothers and parents. Some of the guys she works with know her secret and seem to be okay with it. But she doesn't hang out with them after hours.

She's lonely a lot.

She's thought about going back to being Andrew.

She's thought about killing herself. Most transgendered people do. Half die by the time they turn 30 _ usually by their own hand. They don't want to risk everything to be who they know they are.

But they can't stand to keep looking in the mirror and not seeing themselves.

"It takes a really incredibly strong person to undertake this transformation," Farrell says.

Seventeen years ago, Farrell started a support group for her patients. Starburst has more than 40 members, including Maddie. The girls, as they call themselves, get together once a month.

Sometimes they gather at a St. Petersburg church and invite laser surgeons or makeup artists to give presentations. Or they get together at an all-you-can-eat buffet and talk about the Winn-Dixie truck driver who got fired for wearing women's clothing off the job. Or they rent a movie at Maddie's condo and laugh about whether Patrick Swayze passes as a woman.

They talk about friendship and dating. Some want to meet a man so they can be in a "regular" relationship. Some are still attracted to women.

Maddie isn't sure what she wants. She's had a few dates, all with other transgendered men who present themselves as women. "Sort of like a lesbian relationship," she says.

"But you know," she says, "the longer I'm on this estrogen, the more I realize what's so great about Brad Pitt."

Maddie and the other Starburst members dress like soccer moms, or ladies you might see at a bake sale. They wear sun dresses, short-sleeved sweaters and gold-rimmed glasses. They're parents, grandparents and former military officers. One is a 68-year-old retired Navy commander who has been "playing dressup" since age 5.

Most waited until their children were grown, or until they retired, to start living as women.

Georgia is 60. She has been married four times. She did combat in the Congo. She has been shaving her body since 1978. She used to mail-order women's clothes and have them delivered to her office at MacDill Air Force Base.

She celebrates small triumphs, like someone saying, "Excuse me, lady," at the drugstore. And finding size 14 pumps on the Internet. And waking up and for a few minutes forgetting that she spent most of her life as a man.

The Starburst girls nod and smile. They understand. For many of them, these other "trannies" are their only friends.

"Do you think if we had a choice, we would choose to give up our families and our jobs and our self-esteem so that strangers could laugh at us and stare?" Maddie asks.

"The only choice, for us, is when to stop living the lie."

Face forward

Frank Head, the manager of the driver's license office, tells Maddie to wait a minute. He walks to his office. Maddie stands at the counter, alone. Fluorescent lights glare above her. Behind her, dozens of people in the long line are whispering, smiling.

Maddie turns her back on them. She taps her red fingernails on the counter. She tries not to cry.

Head comes back, carrying a hardback book of Florida laws. He sets the thick book on the counter. Opens to Chapter 316. "Sir, please understand," he says, again addressing Maddie as a man. "Physically, if you're a male, sir, you have to have male on your driver's license."

Maddie blinks. She doesn't move.

Head looks past her, to the long line of strangers. Raising his voice, he gives his rationale for this policy. "If they're incarcerated, we're not going to put a male in the women's jail. If they get pulled over on the side of the road, do I want a female officer patting them down?"

Maddie stays silent. The manager has one more point.

"Still, anatomically," he says over Maddie's shoulder, "he's a man until he has that surgery."

Maddie clears her throat. She steps forward. She reaches onto the counter and closes the law book. She struggles to control her voice.

"Well, sir," she says. "I still need to change my name on my driver's license. And I need a new photo."

The people in line stop whispering. Maddie twists her gold bracelets around her right wrist.

The manager looks again at her documents. Then he looks up. The place is packed.

"It will take at least two hours, SIR," he says.

Maddie says, "I'll wait."

She squares her shoulders, steps back from the counter and turns to face the strangers. She walks past them slowly, her sandals clicking on the bare floor.

When she gets near the end of the line, a skinny teenage girl steps toward her and smiles.

"You're very courageous," the girl says.

Maddie stops and turns. She looks at the girl, who is about 17. She's here with two friends, all wearing tank tops and drop-waisted jeans. They're trying to get their driver's licenses for the first time.

"What?" Maddie asks the girl.

"What you're doing, I admire it," the girl says.

Her friends nod. A few other folks in line do, too.

"And I admire how you handled that man. How you didn't let him deny you."

Maddie doesn't know what to say. "Thanks," she says, finally. "Thank you for saying something."

The girl reaches out and squeezes Maddie's arm.

"You're welcome," the girl says. "I think you're a beautiful lady."

Two hours later, Maddie moves to the front of Line 3. She puts her papers on the counter, in front of another state official, and steps back while he stares her down. She waits while he types her information into the computer. Waits while he verifies her address, criminal record and driving history. Waits while he studies her paperwork, and prints out some more, and changes her address _ and her name.

Finally, it's time for her new photo.

Maddie steps in front of the camera. She fluffs her brown bangs. Everyone is watching.

"You can smile if you want to," the man behind the camera tells Maddie.

She does.


The Internet has dozens of Web sites on transgender issues. Some of the most informative:; transparentcy; and


Enchant, a support organization for the transitioning transsexual,

FORGE (The Florida Gender Equality Project), a political forum working to affect change, (813) 870-3735, ext. 258

Starburst, a support group for anyone concerned about gender-identity issues, www.starburst.bbs/us/ or (727) 523-8760

Tri-Ess, a national support group for heterosexual cross-dressers and their partners, local chapter Tri-Beta,

Tampa Bay Gender Alliance, a nonpolitical forum for all who identify as transgendered, e-mail: tbgafl

E-MAIL MADALYNN SHEPLEY: madalynnshepley


On Wednesday, transgendered people around the world will mark the fourth annual Day of Remembrance. Five countries and 30 states will hold events to commemorate transgendered people who have been killed. In the past year, at least 26 transgendered people have been killed in the United States.

Around Florida, memorial services will be held in Fort Lauderdale, Jacksonville, Clearwater and St. Petersburg. The Clearwater service is at 7 p.m. at the Unitarian Universalist Church of Clearwater, 2470 Nursery Road. The St. Petersburg service is at 7 p.m. on the west side of St. Petersburg's city hall, 175 5th St. N.

The stress shows on Maddie Shepley's face as she takes the elevator to work on her divorce papers at the Hernando County Courthouse in Brooksville.

Two driver's license photos, one person: Andrew Shepley, left, and Maddie.

Maddie works on her van in the parking lot of a thrift store near her home in Clearwater. She was able to get the van running by hitting the starter with a hammer.

Maddie puts on her makeup, left, and gets dressed, below. She taught herself to apply eye shadow and eye liner and started new new wardrobe with old clothes from her ex-wife.

About a year ago, Andrew Shepley moved to Florida and started taking hormones and calling herself Maddie. Here, she walks into the public library in Hudson. She lived in a trailer there before moving into a Clearwater condo.