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Couples 2014

Brian and Debbie McCloskey: He Wears a Dress. She's Fine With That

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Thu, Feb 13, 2014 at 4:00 AM
click to enlarge Debbie and Brian McCloskey, photographed at the Ricardo Montalban Theater - PHOTO BY STAR FOREMAN
  • Photo by Star Foreman
  • Debbie and Brian McCloskey, photographed at the Ricardo Montalban Theater

See our entire Couples Issue 2014 here.

When Brian and Debbie McCloskey got married two years ago, Debbie wore a lovely little neutral-colored dress. So did Brian. It was, perhaps, the happiest day of both of their lives. Brian is a transvestite, which means he likes to wear women's clothes. His wife is totally fine with that.

Transvestites confuse people, Debbie says, sitting in their cozy jumble of a Santa Monica apartment. Both McCloskeys work for the city of Santa Monica - he at the main library's front desk, she in finance. He isn't gay, she says. He does not want to become a woman. He just wants to dress like one.


Brian and Debbie met a decade ago reading one another's blogs. His was "I'm an Idiot, What's Your Excuse?" Hers was "Cheaper Than Therapy." Brian was an Irishman living in Venice; Debbie was still living in her native Kentucky.

The luck of the Internet brought them together. At the top of the page on Blogger, you could hit the "next blog" button and the software would take you to a random blog on the network. Blogger dealt Brian to Debbie.

His wasn't like any other blog out there. He kept lists of license plates of cars parked in front of his apartment building. He'd do crazy surveys, like "cat or lamp?"

"This guy's clever," she thought, and filled out one of the surveys.

"No one had ever done that before," Brian says. "Someone's actually on my wavelength? Somebody gets it."

They became friends. At the time he was cross-dressing in private, but he confided in his long-distance friend. He'd come home from work and slip into a dress and tights for a few hours before bedtime. He'd joke about it. She'd kvetch about getting a rip in her pantyhose at work. He'd say, "Oh, I hate that. You should be keeping a spare in your desk drawer like I do."

"So I would think," she pauses for a moment. " 'Sound advice!' "

How did she feel about it?

"Aah, pfffft. He was my friend. So what? Plus I'm all the way out in Kentucky and don't have to deal with it day-to-day."

Day-to-day eventually came. She lost her job, moved to Los Angeles and became his roommate. Friendship turned into romance.

"In person, this guy's very nice," she says. "Very kind. You know how some people can fake it for a while? But no, this was, like, consistently. Pulled his weight around the house. Helped out. Not that I had low standards. It was, like, oh, here's someone who could be an actual partner." She caresses his wrist and with a sly smile says, "It's not just that you do all the laundry and the dishes."

"Still got my own hair and teeth," Brian says. "Feed the cats."

"It's not just a breakdown of what they do," Debbie continues, serious now. "I know that I'm supported. Do you know that you're supported?

"Yeah," he says.

"It wouldn't matter what you wore. You could wear a cheese costume every day, and what difference does it make? It doesn't change who he is. And if wearing a cheese costume makes him as happy as wearing this dress does, I'm not gonna stand in his way and demand that he conform to some arbitrary standard."

He isn't glamorous, like RuPaul. Or creepy, like some weird, bearded guy in a bikini. Or twisted, like the psychotic killer in The Silence of the Lambs.

Brian is a slender, willowy brunet who dresses like a prim and proper lady out of a Talbots catalog: classy, conservative, covered. He favors A-line, knee-length dresses and tights, with a cardigan to hide his arms and "man shoulders." He's a modest sort of transvestite.

It isn't an illicit thrill for him. He isn't a "hotel door" guy - his term for men who cross-dress only while away from their wives on business trips. "They throw a dress and pantyhose into their suitcase - "

" - Or get some while they're there," Debbie adds. Then they snap a few photos in their hotel room.

Brian knows their happiness and their sadness - the happiness of true self-expression, and the sadness of hiding it from everyone who matters to you.

Though he started wearing women's clothes privately in his mid-30s, it wasn't until two years ago, at 44, that he finally got up the nerve to do it in public. It was during Santa Monica's Living Library program, where you can "check out" a human being for 30 minutes for conversation: gang members, drug addicts, teen mothers, Muslims, gay parents - anyone you might have a preconception about but never actually spent time with. The program slogan is "Don't judge a book by its cover." Brian decided to allow himself to be "checked out" as a crossdresser.

He was nervous. He was excited. How would he do it? Change at work? Bring clothes?

No, he decided, he'd change at home. He got his dress drycleaned, selected new tights, bought a new cardigan. In the middle of the night, he awoke in a cold sweat at the thought of walking the two blocks along Sixth Street from home to the library in full view.

He need not have worried.

"I was fully booked. People wanted to talk to the transvestite. I felt fantastic." It was a bit of a blur. He can't remember what people asked, except that one older lady did quietly inquire, "Do you get sexually aroused when you're wearing a dress?"

"Well," he told her. "Sometimes." But that has more to do with being a man than being in a dress.

Returning to work the following Monday in shirt and tie again felt awkward. "After a couple weeks of stewing, I said to Debbie, 'I think I want to do this.' "

Debbie didn't mind. Neither did his supervisor, who said she didn't care if he wore dresses to work.

He persisted. "Remember when we had that sexual harassment training?" he said. "They said we have to notify HR and there are steps to be taken."

"You notify Human Resources so if anyone else has a problem, they have to go to awareness training," Debbie explains.

At work, the most common reactions from colleagues were "Good for you" and "Surprised it took you so long." And as time went on, "You always look so put together."

"I am the world's luckiest transvestite," he decides now.

Theirs is a good life. A humble, routine, "boring" life, filled with laughter and conversation. Debbie sits on the right side of the couch playing video games, Brian on the left, listening to music with two cats underfoot. "Seriously," he says, "this is us of an evening." Grocery shopping at the local Albertsons is the highlight of their week. Cashiers fight to ring them up.

On the rare occasions they go out, bathrooms are the only time Debbie feels any trepidation. Is it dangerous? Will people harass him?

"So far so good, I guess. We even went to Disneyland," she says. "You used the men's restroom without incident."

"Because I'm a man. I'm not trying to pass. I'm not a lady. I don't think I belong in the ladies' room."

Usually, though, he tries not to use public restrooms at all. He's always hated them.

"But that's always my concern when we're out," Debbie continues. "I don't know that I can protect him. Or need to. That would be the one place I couldn't go and know if anything happened. If he goes into the men's restroom. And there's some crazy thugs in there who freak out?" She pauses. "When we were there, it's like, well, we're gonna be in Disneyland for 12 hours."

Brian grins. "Even I can't hold it that long."

Occasionally people stare. Or they sneak clandestine pictures of him in the grocery store, as one tourist family did the other day. Debbie chuckles. "They don't even know. If they'd just asked, he would have posed for them."

Brian is not offended. He finds it genuinely amusing. "If you look around any supermarket in Southern California," he says, "I'm probably not the weirdest thing you're going to see."

Occasionally, waiters or store clerks make honest mistakes. An earnest, "How can I help you, ma'am?" is followed by the inevitable, awkward, "Oh, I'm sorry, sir."

"Then they feel bad," Brian says. "Then I feel bad because they feel bad."

Though he doesn't necessarily feel more attractive dressed as a woman, there are certain times when he does feel "kind of pretty."

"It was the Ann Taylor," he says, turning to Debbie. "You know, the black-and-white one? When I wore that last month, I was walking to work and I was kind of skipping? Swinging my purse and skipping."

He never felt like a man trapped in a woman's body. More like a man trapped in the wrong clothes. He doesn't know why he likes wearing women's clothes, can't even remember a time when he didn't want to wear them.

"I wish that I could tell you this light-bulb moment went off in my head," he says. "I'm sure there must have been. But I've always been interested in what girls my age were wearing."

As a teenager attending an all-boys Catholic school in Ireland, he didn't care for what the boys wore. But he liked the uniform of the girls' school across town. A lot. It was a sleeveless wool pinafore worn over a white collared blouse with gray tights. "Obviously could never wear it. Never had a hope of wearing it."

As he got older, he would check out a pretty woman in a nice outfit and think, "I would totally wear that."

"It's not women's trousers," Debbie says now. "It's not blouses, or skirts. It's dresses. It's a specific piece of clothing."

These days he is partial to Calvin Klein. The same garment, in multiple colors. He may dress like a woman, but he shops like a man: Find something you like and buy eight of them.

The tights also are essential. "To me, yes, they're functional, but they're something else. And I don't know that I can put into words what that is."

Walking into the bedroom, motioning to a tiny bureau wedged between the foot of the bed and the wall, he pulls out one of the drawers to reveal rows of neatly folded pairs of tights, arranged by thickness. "This is the principal tights drawer," he says, tucking a stray hair behind his ear. He keeps his hair long. Debbie keeps hers shortish. Neither bothers with makeup, though Debbie has offered to help him figure out how to apply it if he wants.

To avoid repetition, he tracks his outfits via spreadsheet. When he first started cross-dressing in public, he figured, "I'll mix it up." Boy clothes one day, girl clothes the next. Two weeks of that was enough. To hell with it, he said, and moved all his shirts to the back of the closet. "I'm not wearing these again."

In the years since, after detailing his decision on his blog, Brian has received emails from guys all over the world. "You're so brave," they write.

"I don't think of myself as being brave," he'll write back. "And I don't think of myself as anybody's role model. Or hero. The hero of my story is Debbie. It's the people I work with. It's the male colleague who tells me, 'You look great today' without worrying if that makes him gay. They're the role models."

Turn the page to see what Debbie has learned.

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