All Dressed Up And No Place to Go?

When I was a teenage boy my friends and I used to say that to each other quite a bit. If one of us would show up with a new outfit or even just a clean shirt we would chide him, “Look at him. All dressed up and no place to go!”

That phrase stuck in my mind. Not too many years later when I expanded my interest in women’s clothing from a simple vehicle for arousal and masturbation to trying to look and act like the complete woman I would only go so far as getting a hotel room, going through the steps of transformation, shaving, applying make-up, dressing in bra, panties and hose, putting on a wig, applying more make-up, putting on one outfit after another, checking my make-up, taking some photos or shooting a little video all the while without leaving the hotel room. At some point I would sit down, probably so I could see myself in the mirror and sigh to myself, “look at her: all dressed up and no place to go.”

Can you relate to that?

I recall feeling like a prisoner in my own hotel room. The prison guard was my own fear that if I ventured out someone would see me and an embarrassing scene would ensue. Luckily, after several of these self imposed imprisonments my desire to venture out overcame my fear of embarrassment.  I started to leave the confines of my hotel room while dressed as Linda.

At first the trips were small, not more than a few yards down the hall to get ice or soda from the hotel vending machines. How my heart would beat! Sometimes I would venture to the room balcony to survey the scene and perhaps photograph myself standing in the daylight. Should even so much as one car come in to the parking lot below I would scurry back inside. I guess I thought I was the center of the universe or at least the center of everyone’s attention.

The next trips were short car trips to a nearby parking lot or just driving around. There was the one time I went for a walk in a Montreal park. I was enjoying the feeling of the cool air coming up my skirt when suddenly a branch reached out and pulled the wig off my head. That caused a setback in my outbound journey but only temporarily. With each trip out that did not bring instant shame or embarrassment I looked for further journeys.

Great advances came when I was able to attend support group meetings to learn the first-hand and very similar stories of others and special weekend events like the old Texas T-party and Paradise in the Poconos.  For some those type of events were and are their one and only chance to get out en femme. For me they just whetted my appetite for trips in to the ‘straight world’.

Soon I started searching the literature for references to the best clubs to visit where a girl like me could get dressed up and have some place special to go. Bars with names like Jacques’, Disco Cleopatra, Club Edelweiss, Ziegfeld’s, Baton Show Bar, Cartwheel, Backstreet and of course the Queen Mary beckoned. I visited them all.

As you will know those clubs are spread across North America. To visit them required a lot of travel. It also involved a lot of ‘down time’ during the day. Being a few hundred and sometimes several thousand miles from home I got the nerve to get dressed en femme to go shopping at nearby malls. Thanks to advice I had heard from others I dressed, not as if I were going to the club but instead dressing to fit in with the other lady shoppers. That often meant wearing (ugh) jeans and baggy shirts. These were not the sexiest clothes but at least they allowed me to be less conspicuous. I may not have completely passed but it seems I wasn’t offending anybody. While I had to dress down at the mall I was able to try on dozens of lovely dresses, gowns, suits, skirts, blouses and lingerie in stores like Macy’s, Dillard’s, Bloomingdale’s and Lord&Taylor. (As lovely as their clothes were my purchases would inevitably be from Marshall’s or Ross Dress for Less.)

Shopping is still a large part of my ventures out. However here is what I’m now excited about: the whole world is available to us even when we dress en femme. We are only prisoners of our own fears. When we dress and make ourselves up to fit in for the occasion we are not likely to draw negative attention or comment.

Now I am often out as Linda going to restaurants. I find art galleries and museums particularly enjoyable. Golf is fun and kind of ‘sexy’ to play en femme however I must admit to a hesitation that a lot of women have about showing up at a course as a ‘single.’

It was really cool attending an LA Kings hockey game and a taping of the Jay Leno Show with a ‘fellow traveler.’

I have a couple of theories why this six foot tall cross-dressing ex-footballer is so comfortable venturing out in the straight world.

1) Ground breaking talk shows going back to the Phil Donohue days have made people more aware that cross dressers are not the treat we were once thought to be.

2) For the sales clerk and restaurant staff we are customers and potentially good tippers.

3) Stores spend a fair bit of resources giving sensitivity training to staff at least in part to avoid costly lawsuits from potentially embarrassed customers. I suspect I benefit when store staff might ‘read’ me but think I could be a transsexual entitled by law to the services available to any other woman. When dressed I have never been turned away from a women’s ‘Fitting Room’ or even a washroom.

4) We North Americans have become increasingly wary of others and do not want to ‘get in another persons way’. Someone seeing Linda in a mall may be very offended but still not say anything. To him or her I may be ‘the next crazy with a gun.’ As a society we tend to keep our distance and keep our feelings to ourselves.

5) As I mentioned earlier it is very important to dress and do our make-up for the occasion. The tall high-heel wearing mini-skirted bubba is going to attract negative attention in the mall, on the street or anywhere but in the confines of the city’s drag bar. Well, even in the bar the queens will make catty comments under their breath. The same person wearing flat shoes, looser fitting clothes, a good make-up foundation but with minimal make up with color may still be noticed but will not likely be considered offensive to others and therefore not attract negative comments.

So girls; have you any advice to add? When you head out where are your favorite places to go and why?

Category: Transgender Opinion