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I’ve known Gary Page for 20 years. The foreman of a moving crew, he’s helped me move my furniture and belongings on four different occasions. At five-eight and 220 pounds he looks like an outside linebacker for the XFL, and he has all the attributes you’d expect of a great mover: he never drops anything, he knows how to get my jukebox down a winding flight of stairs, and he doesn’t talk all the time.

A couple of summers ago, as we wound down another move, Page invited me to a party at the Golden Flame banquet hall in west Jefferson Park. Like most movers and clients, we’d seen each other only at our worst, so I decided to take him up on his offer. I figured there would be cold beer, good music. You know movers.

I didn’t know my mover. The night of the party I arrived at the Golden Flame to find more than 120 colorfully dressed members of the Chicago Gender Society (straight, gay, lesbian, bisexual, transgendered) and the Society for Second Self (a support group and social club for heterosexual cross-dressers). Page introduced himself as “Miss Gina.” He wore a purple-and-silver sequined gown and five-inch stiletto heels with silver rhinestones across the toe and arch. I was–well, moved.

Most of the guests were friends and customers from Page’s other business. Skyscraper Heels, at 2202 W. Belmont, sells high heels, corsets, and women’s accessories to men–and more recently, women. It has a few competitors in southern California, but there’s nothing else like it in the midwest. Once in a while Page will hand out one of his pink business cards during a move, but he’s fairly circumspect about it. “Nine-tenths of those customers don’t come in,” he says. “And I don’t tell them about the cross-dressing.”

At 57, Page can’t remember the first time he tried on high heels. “It was so long ago.”

“Gary walks pretty damn well in a five-inch heel,” says Luci Lindstrom, who manages the store. “He walks better in them than I do….There used to be a saying about, when you went to a party, look for the person with the highest heel and it’s probably a guy.”

Women’s shoe sizes are usually about a size and a half larger than men’s, though boots or pointed stilettos might run two and a half sizes larger. The stock at Skyscraper Heels ranges from size 4 to size 17. The store’s walls are lined with high heels, corsets, garter belts, and breast forms, the hot pink decor a sort of Cupid-meets-Lewis Carroll. “We get cross-dressers, dancers, drag queens, strippers,” says Lindstrom. “But there’s a lot of straight women out there who love our style of shoe. I’m saying women in their 20s. I’m saying a lot of straight guys buy these heels for their girlfriends. They’re only going to do one thing with them–and they’ll never leave the house.”

Page says that one of his clients is a federal judge. “She has big feet and says she’s tired of the drag queens buying all the good shoes.” Last Valentine’s Day, cops from the 19th District picked up seven pairs of shoes to give to their wives or girlfriends (that’s what they said anyway). Around Labor Day, when Chicago hosts the Miss Continental beauty competition, drag queens from as many as 17 states drop by the store. Ginger Grant and Chili Pepper, both performers at the Baton Lounge in River North, shop there for their heels. “We couldn’t get Chili Pepper in here for the longest time, until Nordstrom’s discontinued her shoe.”

Not too long ago a Polish woman in her mid-60s walked into the store. “We had three drag queens on the couch,” says Lindstrom. “I had a guy coming out of the bathroom with his mistress and a stripper dancing on the floor. The Polish woman acknowledged everyone, tried on some shoes, and bought some. We fit into the neighborhood. We low-key it.”

According to Lindstrom, when the store opened in June 1998, 65 percent of its clients were men, but now the ratio is fifty-fifty. “We have lawyers. Policemen. A lot of construction workers. We also don’t know who a lot of people are.” People from all walks of life patronize Skyscraper Heels, though it’s awfully difficult for them to walk.

“Women have gotten lazy. We’ve forgotten how we’d allure the guys when we were younger. The stiletto does two things: it tightens the calves and lifts the ass. It makes you walk a little sexier. You become a woman when you’re in heels.”

“That’s what heels do,” says Page. “You have to put your foot down completely–even pressure, heels and sole at the same time. It causes your hip to sway.” No wonder this guy never drops anything.

“Gary has always had a shoe fetish,” says Lindstrom. Page studied engineering at the Illinois Institute of Technology but left without earning his degree. During the late 60s he sold bicycles in Lincoln Park, and after burning out on that he became a bus driver here and later in Minneapolis. In 1977 he started his moving service, Gary Moves It.

On July 3, 1990, he was walking down to Grant Park to watch the fireworks when he noticed a shoe store on Michigan that was going out of business. “I’d sold industrial shelving when I started moving,” he recalls, “so I wandered in to see what their backroom shelving looked like.” The store’s inventory floored him: 90 pairs of pumps between size 10 and 13, with five-inch stiletto heels. He called his friend Lita Sweeney, the owner of Translucere, a large-size lingerie boutique then on Lincoln Avenue, but she told him she couldn’t afford to stock such expensive shoes. “I called the manufacturer and said I’d like to put in an order,” says Page, grinning. “He said, ‘Who are you?'”

Page started buying shoes and selling them on consignment at Translucere, and his side business began to grow. “I was never at Translucere on a daily basis,” he says. “I was just trying to help her succeed.” Lindstrom, who was waiting tables at Mitchell’s on Clybourn, started working at the store on Saturdays after it moved to Belmont in 1997. The next year Page decided to expand the store’s stock to include women’s heels so that he could buy even more shoes. During one trade show in Las Vegas he dropped $25,000. As Lindstrom recalls, “Lita told him over the phone to quit buying shoes. When Gary got back from Las Vegas he asked if I wanted to be a waitress all my life. I said, ‘No.’ He said, ‘How would you like to run your own store?'”

Page opened Sky-scraper Heels that summer with money from a couple of real estate deals. He never developed a business plan; he just rented a storefront to house the booty he’d brought back from Vegas. The store now has 250 shoe styles. Shoes sell for $29 to $129, and boots run as high as $279. Corsets imported from England range from $169 to $500. For people with pony fetishes there’s the all-leather black Grand National pony boot with lace-up sides. “Actually, the fetish people haven’t been buying it lately,” says Page. “It’s been more of the artsy-fartsy crowd.” The ultimate S-M footwear is the eight-inch ballerina boot or shoe; the heel is a fraction longer than the toe, which means you can’t stand in them. The shoe shifts your weight forward from your knees. “You slip down,” says Lindstrom. “It’s strictly a posing shoe.”

Lindstrom says she now dates a younger straight cross-dresser (who dresses only at home). “With a guy who dresses, there’s this guy part of him that goes to work every day. Then he has this softness side, because he knows what it takes to become a woman. He knows how much time it takes to put on makeup, to actually allure someone. That softness is what I like about a cross-dresser. Yet my boyfriend still has this little bit of macho little boy still in him.”

Tina Slash stops in one Friday afternoon. The maid in attendance at Gallery Domain, a private club in Wicker Park, he wears his work outfit of fishnet stockings, seven-and-a-half-inch platforms, and a corset over his minidress. He owns 20 pairs of women’s boots, 50 pairs of women’s shoes, and 31 French and English maid outfits. (But don’t refer to him as “she”; he’s a fetishist, not a cross-dresser.)

“These platforms go with all the outfits I wear,” he says. “Part of this, for me, goes back to my days in the military. I spent years in marches in high school, college, and 11 years in the army. I’m always conscious of where my feet are. That’s why it’s easier for me to walk in these than a lot of other people.” I ask him what dressing up does for him internally. He pauses for a few moments. “That’s a good question,” he says. “Actually, it helps you put on an attitude. Especially if I’m wearing the right boots or the right clothes. Then nothing bothers me. No matter what anybody says outside, I’m dressed. I’m ready to go.”

Art accompanying story in printed newspaper (not available in this archive): photos/Lloyd DeGrane.