Straight into a dress

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In the end, surprisingly enough, it was much less painful making my penis vanish than having my eyebrows plucked.

The instructions for the device I had been handed – called a “Jayne belt,” it looks like a thong and is designed to “get rid of the male genital bulge” – didn’t inspire confidence. “Push each testicle up inside the body into their respective cavity. With one hand, hold the testicles up inside and with the other hand, push the penis down and back toward the rear,” stated the instructions. “This is called ‘tucking.'”

Now, if you’ve never tried this, it’s harder than it sounds. I’ve heard that sumo wrestlers are trained to retract their balls into their body prior to a match. I don’t have that facility. I had also heard that fear had somewhat the same effect. Apparently not. But when I finally get everything in position, get the strap of the belt secured firmly up my ass and pull on a pair of tight, but tasteful, black panties, it’s actually much less uncomfortable than I would have thought, had I ever imagined the situation before.

But wait, I’ve skipped the torture that had taken place four days earlier.

That was the Tuesday I had gone to do a preliminary interview with Paddy Aldridge, the owner of transformation specialists Take A Walk On The Wildside, and the woman in whose hands I would be placing my very masculinity, so to speak. She decided we might as well start preparing for my Saturday session then and there, by plucking my eyebrows into a slightly more feminine – less bushy and prickly – appearance. Upending me in a modified dentist’s chair, she proceeded to attack my eyebrows with tweezers and slightly demented enthusiasm. Fuck, that hurt! With tears streaming down my face, I contemplated the possible ruin of my ruggedly handsome features and wondered how I had got myself into this position.

Now wait again. Maybe I should start at the beginning.

It had all begun several weeks earlier. Being one of the few straights on staff at Xtra, I was approached to do a story on the overlooked world of straight crossdressing. And so, on a 40-degree June Saturday afternoon, I arrive at Wildside’s downtown building, with my bio-female friend Wynne in tow for moral support and my eyebrows looking surprisingly well-groomed and becoming.

The business is located in a three-storey house near the gay village. The main floor is taken up by a store, with everything the crossdresser – novice or experienced – might need: blouses, skirts, dresses, boots, bras, panties, padding, wigs, makeup, devices to conceal this, to accentuate that. The second floor has a small kitchen and a brightly decorated living room that doubles as a Saturday night karaoke venue and a stage for small plays. On the third floor are small bedrooms, where clients, especially those from abroad, can stay overnight. In the basement is a transformation studio.

I arrive prepared for the worst. Which promptly happens. The photographer has arrived to take the before shots. I hate having my picture taken at the best of times. Given what’s about to transpire, and the fact that he’ll be back for the after shots – which will be shared with Xtra’s millions of devoted readers – this doesn’t seem like it’s going to be the best of times. But I grimace and make the best of it.

Then Paddy Aldridge arrives and drags me down into the basement for my transformation.

***

Paddy is happy to tell you about her life before she started Walk On The Wildside in 1987, about how she was a stripper, a hooker and a Ryerson theatre arts student before she became Toronto’s crossdressing maven. It’s not clear from listening to her which of these she regards as a step up.

Paddy says that when she started the business, she was just drawing on past experiences.

“When I was a stripper, I travelled with the drag troupe The Great Imposters. I was the stripper in the afternoon, and they were the show in the evening. Guys in drag were the norm for me.”

But Paddy says she hadn’t counted on the differences between drag queens and straight crossdressers, and the pressures on her straight clients.

“No one trained me to do this. The psychological pressure on me at the beginning was tremendous. I would spend hours listening to them cry. I started to develop a fear. I never knew when someone was going to freak out.”

Paddy says she saw countless marriages fall apart when the husband began dressing as a woman. “Most women don’t like it when their husbands crossdress. I’ve got a guy who wants to put a dress on and his wife is standing there with her hands on her hips, saying, ‘I don’t want to be a lesbian.’ I would say, ‘It’s harmless,’ and I could eat my words. It’s not fucking harmless. A lot of men will have latent homosexual fantasies. And crossdressing is worse than being gay. If you’re caught crossdressing, there is a chance you could lose your job, your wife, your family, everything.”

Only a small number of her clients have undergone gender reassignment surgery since crossdressing with Paddy.

That sense of being psychologically responsible for her clients, coupled with the sheer volume of business, drove Paddy into addiction.

“We were so busy in the first five or 10 years, that to deal with the demand I would just snort another line or drink another glass of wine.”

But now, clean and sober, Paddy sees some similarities between her clients’ needs and her own addictions. To her, some of her clients are addicted to crossdressing, and they would be healthier without it. However, she’s decided that her clients will have to be responsible for their own motivations and their own lives.

“I’m responsible for myself,” she says.

In fact, Paddy says some of those motivations are certainly not what one might expect. Strangely, revenge against a particular woman who has rejected or done something to the man is a popular reason for crossdressing.

“When they’re all dressed up, they say, ‘I look more fabulous than you. People are looking at me. I’m a star.'”

***

Down in the basement, I’m feeling like anything but a star. With everything tucked and retracted and my eyebrows plucked, I’m slipping on a pair of panties. Now, I have worn women’s panties before, but only as part of some SM sex games. Today, sex just isn’t anywhere on the menu.

The next step is to deal with my legs. First, a heavy pair of tan pantyhose to cover up the abundant hair and to shape the legs. Then a pair of black sheers for sexiness. And I have to admit, my legs look pretty good. I’m heartened when my friend Wynne curses this fact.

Unfortunately, my ass – which I had thought might be good enough as is – just doesn’t pass muster. My hips and ass just aren’t feminine enough, so it’s time to break out the padding. I slip on a pair of padded briefs, and suddenly my ass is jutting out and I have child-bearing hips. From the waist down, I think I’m doing okay.

But we’ve now moved on to the torso. It’s time for me to grow tits, and, judging by the size of the silicon fakes Paddy is handling, pretty fucking big tits. First though, I need to put on a bra, a quite tasteful black one, presumably to match the rest of my underwear. Then the silicon is stuffed into the bra, and suddenly I’m sporting 40DD tits. Now, I’ve always been more of an ass man than a breast man, but I admit it, I’m impressed. Paddy urges me to jump up and down to see them bounce, although I seriously doubt that any woman with 40DD breasts spends much time jumping.

Next I’m going to get dressed. I had thought of a nice tasteful business suit, something modest and restrained. But it just isn’t to be. I get a short, tight black skirt that comes down only to mid-thigh. Now I’m worried about looking slutty.

The top is a tiger-print crewneck that requires a little cosmetic shaving at neck and wrists. It doesn’t really match my personality, but I think I can pull it off. But it does demonstrate what is obviously going to an insurmountable problem. Not the Adam’s apple, which is surprisingly unobtrusive. But there’s just no way of concealing the width of my shoulders or the male V-shape of my upper body. Even with the huge tits, it’s an upper body that doesn’t look typically female.

But I’m soon distracted from these worries because it’s time for the main event of this makeover: my face.

I learn that apparently a man’s neck and face don’t match in colour the way that a woman’s does. The solution is to make them match by using a shit load of foundation. Then it’s a lot of powder, which apparently, “Gives your makeup stamina.”

I can’t actually see what I look like at this point, because I’m fully reclined in the dentist’s chair, what Paddy later refers to as, “being laid back in the psychiatric position.” But the sheer volume of makeup being applied to my features does not make me feel confident.

Now we move on to my eyes, starting with eyeshadow, followed by liquid liner and mascara. Then it’s a liberal application of blush for the cheekbones and, finally, lipstick – a nice red shade, the exact name of which I forget to note. Finally it’s the wig, a long, rather 1980s-looking brunette thing, whose big hair is designed in part to draw attention away from my square jaw.

I’m finally able to sit up in the chair, and get my first look at the new me. At first glance, I look like a geisha. At second glance, it looks a little better, but it’s not a face I’m ever going to call pretty. Worst of all, I think it makes me look older.

I try on a pair of high heels and nearly break an ankle just trying to walk across the room. I settle for a far more modest heel on a much plainer pair of shoes that still hurt my toes. I also have to learn to hold my new purse, not slung across my shoulder like a knapsack, but daintily, as if inviting a pursesnatcher to do his best.

The photographer returns for the after shots, and tries to conceal his amusement under compliments. Oddly enough, I feel more comfortable being photographed like this than I do normally. But I quickly learn that as a woman wearing a short skirt, I have to sit rather differently.

I remember something Paddy said about the way a lot of men want to look as women. “They want to look like the girls they want to fuck.” Well, I don’t think I would want to fuck myself if I had a paper bag over my head.

But the real surprise for me is not my lack of sexual self-attraction, it’s how little effect dressing and looking like a woman is having on me. I’m never unaware of my new look, but it’s not making me feel any different. Paddy seems disappointed. I think she was expecting a complete personality change, but I feel like the same man, just in very different clothes. I can’t even bring myself to try the breathy, faux-Marilyn voice that Paddy wants me to try.

***

I discuss this issue of personalities with several of Paddy’s other clients at the Saturday night karaoke session in her living room, and I get differing responses.

TJ, a 26-year-old Asian, is the most convincing woman I see all night. In fact, it takes me a while to be certain she’s a crossdresser and not a biological woman. She credits this verisimilitude to the great deal of money he’s spent ordering custom-made padding for hips and breasts.

“I couldn’t have been more than 16 when I realized that otherwise I would just look like a guy wearing a dress. Now, once or twice a week I get dressed up and I go for a walk downtown.”

Even so, she says the need to crossdress is not conducive to beauty. “If you want to feel good and look good – they’re mutually exclusive.”

But TJ still admits to a need to crossdress, and has been coming to Wildside events for a couple of years. “Deep down we do this because we need to. Deep down, there’s a sort of compulsion.”

But she says her personality doesn’t really change.

“I’m a little freaked out by people who change completely, who become a completely different person when they crossdress.”

But for Valerie Fox, that change seems to come with the territory. Valerie has been part of Paddy’s group since the start, and before that, would dress up on her own.

“I’ve always felt that I’m a man trapped in a woman’s body.”

But Valerie says she’s afraid of what could go wrong in gender reassignment surgery or with hormone treatments.

“This gives me an out, lets me forget my troubles. Valerie is her own person, she has no troubles.”

Valerie stresses that she has no sexual interest in men, but says that the gay community is as close to welcoming as anyone gets.

“The gay community has been very supportive. We don’t have our own community. I feel like we’re tolerated. But we don’t mean any harm to anyone.”

I don’t share any of the compulsions or needs the men gathered at Wildside have. I will probably never do this again. But I still want to try to get some sense of what these crossdressers have gone through in their struggles, especially what they experienced the first time they ventured out in public dressed as a woman.

Paddy, Wynne and I decide to go for dinner at a Thai restaurant around the corner from Wildside. En route nobody seems to look twice at me. In the restaurant, neither the staff nor the other customers even blink. The food is very good, and I take a certain pleasure from leaving lipstick on the rim of the glass and the straw. As we discuss the history of Wildside over the meal, even Paddy seems to forget that I’m supposed to be a woman now.

But after dinner, we decide my new persona needs more exposure to the cruel gaze of the outside world, so we decide to visit a bar on Carlton. But even there, near Maple Leaf Gardens, everybody seems more or less oblivious. Now had hockey been in season and the Leafs still playing there on a Saturday night, things might have been different. But as it was, while people seem to look twice, this being Toronto, everyone drops their gaze and nobody says a thing within earshot.

But the odd thing is how little I think it would bother me if they did. I had expected, when dressed as a woman, to feel more physically insecure. As a 6’1″, 200-pound man, I’m used to physically claiming my space without even trying, and I’m used to feeling physically confident in my body. Dressed as a woman, I feel the same way. I walk with my shoulders back and tits out, I look people in the face and I defer to nobody on our walk. Again, I was aware of how I was dressed and how I looked, but my essential personality remained the same.

In Zipperz, the gay bar we visit, of course nobody cares. The line dancing in the back means everyone is distracted by a soundtrack of country songs anyway, although no Tammy Wynette comes on while we’re there. I’m told that the bartender was checking me out, although it may well have been out of sheer disbelief.

While the staff and clientele of Zipperz aren’t really my type anyway, the truth is that at no point in the course of the whole day do I feel the slightest sexual charge. Even if my cock and balls weren’t retracted and tucked away, they wouldn’t be needed.

I talk about the questions of sex and relationships with two other clients, Tammy and Jamie. Tammy has been coming for a couple of years and now leads karaoke night with the biological girlfriend she met at Wildside.

“I met a girl who wanted someone like me,” says Tammy. “She had joined the Wildside club. Now she drags Tammy out shopping and to arts galleries. But Paddy says she’s the only girl she’s seen in her 20 or 30 years that feels that way.”

But Jamie, 63, is in a different situation with his wife. On this night, Jamie wasn’t crossdressing because for the first time he had persuaded his wife to come along. Jamie says he had experimented with dressing up in his teens, but had stopped until he dressed up as a woman for a Halloween party in the ’80s. But when he showed his wife his dressed-up self, she did not respond well.

“She didn’t like it. She told me to stop it. Then when I found out about Wildside two or three years ago, I thought it was an outlet. I tried to convince her I look pretty now. I think we took an important step tonight.”

But for Jamie, crossdressing seems to be less a compulsion than something he enjoys. “She’s more important than the crossdressing. I can divorce myself from the crossdressing. It’s not that burning an issue for me.”

But, he adds, “I’m early retired. She works. So I can crossdress at home when she’s not home.”

I can relate to Jamie more than anyone else I’ve met at Wildside. But I can’t see myself ever crossdressing at home. Indeed, to Paddy’s disappointment, I decline the opportunity to go home and write this article dressed as a woman.

I also decline the opportunity to participate in the karaoke night going on. You gotta draw the line somewhere.