SEE Magazine
Copyright © 1997. All Rights Reserved.



Roxy's just got a light covering today. The heavy pancake makeup doesn't exactly achieve a peaches-and-cream complexion, but what's a girl to do when you've got five o'clock shadow pushing through. "I didn't have time to give myself a close shave before you arrived," Roxy tells me.

After all, dressed down in a sweatshirt, sneakers and a smart red denim mini, Roxy had planned to spend the day unglamorously pulling up weeds in the back yard. He's the handyman about the house. He's also the girl behind the counter in Take a Walk on the Wild Side, a Toronto boutique catering to cross-dressers and drag queens, owned by Roxy's wife Paddy Aldridge.

They got married last Halloween. It was fitting. As a budding cross-dresser in small-town Ontario, fright night was the one time a year Roxy (actually Tom, a straight guy who loves women so-o-o much he dresses like them) could dress to the nines as a woman and be accepted.

Naturally, they were both brides. Tom, 49, had pretty much given up on having a relationship when he met Paddy at the store three years ago. He had one marriage fail because his wife couldn't deal with his desire to dress as a woman. "Then I met Paddy, who is bisexual and was married to a post-operative transsexual - that is, a man who had changed sex to a woman."

Go ahead - I was shaking my head at this point, too. But I had the added bonus of having this told to me by a distinctly male voice coming out of a perfectly painted mouth. Holy genderfuck, Batman! But when you think about it, Paddy and Roxy are the perfect match. "I'm man and woman enough for Paddy."

Paddy agrees. "I'm attracted to Tom, who fixes things around the house, and I'm attracted to Roxy, who is kind and submissive and does what I say."

But more important, Paddy made it okay for Roxy - Tom's feminine persona - to shine. "Roxy has taken over," he says. "I paint my toenails, and I shave my body completely. I also sleep in a nightie - just as I did when I was a child."

In fact, there are a lot of signs from Tom's childhood that explain his desire to live as Roxy. His father was never around and he was raised by his mother, her three sisters and a grandmother. "I learned to sew before I rode a bike," Roxy . . . uh, Tom tells me. "I never did team sports or guy things and I always wanted to be Annette or Darlene of the Mousketeers."

It wasn't until he wore nail polish to kindergarten one day that he realized there was anything different about this. And as the second of two sons, his parents didn't discourage his behavior. "One day, when I was dressing up for Halloween, I heard my father tell my mother, 'Marg, I think we've got the daughter we've always wanted.'"

But while both straight and gay people often presume a man in women's clothing is gay, Tom says he has never considered having sex with anyone other than females. In fact, he says, 99 per cent of the shop's clientele are heterosexual males.

"And I'm not a female trapped in a man's body," he adds. "I simply prefer the female gender. I don't do it to entice men to hit on me and I try not to offend women or gay men by dressing this way. I do it to express myself and to be more intimate with my partner."

Roxy refers to Virginia Prince, a pioneer in cross-dressing circles (now 83), who abandoned his masculine identity entirely 27 years ago. "Virginia believes gender is learned like a language. While your sex is between your legs, your gender is between your ears. He abandoned his masculine gender because he found it too stressful to live up to."

Roxy too believes men are more restricted in their gender roles. Not only do women have more options in what they can wear, but a man displaying stereotypically feminine traits such as crying or being more gentle is less acceptable than is a woman displaying traditionally masculine traits like aggressiveness.

And even more scary for a straight man than being perceived as feminine is being perceived as gay, he adds. "Ironically, when I'm Roxy, being with Paddy makes me a lesbian I suppose," he laughs. "But all these labels are bullshit."

So how does he think he cuts it as a woman? "I'm six foot one (and that's before the size 12D heels) and weigh 225 pounds. I mean, I'm a cross-dressed man," he admits. "I have no intentions of passing as a woman. When I look at myself in the mirror, I think, 'I'm having fun and expressing my feminine gender,' that's all."

It all sounds pretty logical, but I have one small beef. Femininity is about a lot more than throwing on some makeup, heels and a wig. In fact, I can't help but feel that most cross-dressers end up coming across as parodies of women; overstated, and not like any women I know (except maybe that tacky friend of my mother's).

When I express my concern to Roxy, he counters that simply wearing the clothes changes how you act as well as your attitude. "If you wear high heels for nine hours, the walk and the gestures develop," he says.

Still struggling with this, I recently mentioned it to a friend who thought perhaps it might be like lighting candles and dimming the lights to create romance. It isn't romance itself, but it shifts your thinking in that direction. That sorta made sense.


Besides being a self-described overeducated shop girl (he has an honors degree in poli-sci, bachelor of commerce degree and a masters degree in business administration), Roxy is also the corporate model for Take a Walk on the Wild Side. The shop not only supplies all the things needed to make that man the woman he always wanted to be, but also does transformations ($120 plus GST) to show how to do it right.

They also have a room on the third floor where cross-dressers can play dress-up and strut their stuff in front of mirrored walls, enjoy a Jacuzzi or even stay overnight (one night's accommodation is $50). "When we get a lot of people it's like a girl's dorm," Roxy laughs. Paddy and Roxy also encourage cross-dressers to bring their wives and significant others along, both as support and to gain a greater understanding of their partner's feminine side.

You can Take a Walk on the Wild Side at 161 Gerard St. E in Toronto or call them at (416) 921-6112. Look for them on the Internet at or e-mail them at

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