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My Best & Worst Outing

By Elizabeth Parker



Would you like to share Your Story with us? It's easy! Submit your copy by e-mailing it to Cindy Martin here at TGF. Hope to hear from YOU!

I have never had the experiences that some of you have had. I'm not very adventurous, I have a non-aware family, and as you might suspect from my monthly column, I prefer my excitement in the form of fiction. But I do get out, and I thought you might enjoy reading about one experience I had where I had both the best validation of myself as a woman possible given my circumstances, and the worst goof I ever pulled, all in the same day.

Since I have limited opportunities to dress, I do like many of you, use business travel as an opportunity. Several years ago on a two week trip, I had a weekend to myself. It was the perfect chance to go out during the day. I've been aware for a long time that going out at night is risky. I'm usually in places which are fairly conservative, and any night activity stands out. Even though I prefer the cover of darkness, I realize that to properly blend in, I have to suck it up and go during the daytime if possible. So that's what I did.

In order to not stand out, I used a dark brown pageboy wig, conservative, day-time makeup, and black pantyhose with flats. It was a coolish fall Saturday, so I should have worn jeans and a top. But I just had to wear my latest acquisition, a red and black tailored sheath dress with long sleeves. It was cut above the knee however, so it looked somewhat informal. I checked my makeup in the mirror again. It was as perfect as I could make it. Admittedly not as awesome as some, but pretty good for me.

I checked my purse. Real driver's license, car keys, credit cards, and hotel key. I have always been paranoid about forgetting one set of keys or the other and having to deal with getting a new set in-femme. And... a replacement tampon. Yes, it was that time of the month!

I peeked through the keyhole. Nobody coming. I cautiously opened the door and stepped out, my flats made a clicking sound on the outdoor concrete balcony. I checked both ways; still nobody. I clicked toward the elevators, trying to remember the right walk. I don't go out often enough for all of the behavior to be automatic. Hell, I'm not even sure I'm getting it right while thinking about it.

I still think it was pretty brave of me to go out while staying in a hotel with elevators. Get trapped in an elevator with someone who has minutes to scrutinize you, and who knows what embarrassing things could happen. Worse yet, this was a resort community, which means lots of teenaged girls! By that time I had gotten to where I could go out relatively undetected, but all my reads had been by our envied foes — the girls.

This hotel had stairs paralleling the elevators, but it was the middle of the day, no one in sight, so I thought I'd take a chance on the elevator. Might as well go for broke. I pushed the button and waited an eternity for its arrival. I just knew a family of eight would decide to go swimming right then. My heart was pounding, yet I was still enjoying the sound of my shoes on the tiles, and the light breeze blowing up my skirt as I waited. I also faced an untypical problem. I had worked on the walk, but what about the wait? How do I stand still and look feminine?

The elevator arrived with no one aboard. My heart quieting slightly, I stepped on. These elevators were glassed on the outside so I could view my surroundings as I descended. As the doors shut and the elevator started to move, I observed several cars entering the parking lot. Now instead of my heart pounding, it stopped altogether. Sure enough, as the elevator neared the ground. I saw the first car park, and a young businessman get out. Of course he had to be fast. Fortunately I had read many of your accounts by that time and knew what I had to do; act confident. So that's what I did. As I exited the elevator I encountered the man. I gave him my best smile and kept right on walking, hoping I'd gotten the mannerisms right. Then the high point of my day ocurred; he smiled back! Ok, he was in a hurry, he was a guy, but he smiled at me, a woman! In that part of the country, I don't think he would have done that had he suspected anything.

With that experience under my belt, I strode confidently to the car. I am woman, see me shop! I climbed into the car, careful to sit first and demurely swing my legs in after. I had this down!

I started the car and drove to the nearest mall. For some reason I actually worry more in the car. Even though it provides a natural barrier, and people can't see inside it very well, I worry about getting stopped. But with my new experience I drove confidently, though still not speeding! Highly untypical behavior for a Type-A personality.

I arrived at the mall, and parked. Being a fall Saturday, the lot was full with holiday shoppers and I had to park at the back of the lot. Then as I emerged, I hit my head on the roof of the car. Being my head, no damage was done, but it dislodged my wig. Not much, but my confidence was shaken. Yes, I should have fastened it, but I hadn't.

There were many passersby so I tried to surreptiously adjust the wig back in place. After getting it the way I wanted I closed the car door and started toward the mall, tucking my car keys into my purse. Again I enjoyed the feel of the breeze blowing against my nylon-covered legs and the dress brushing my thighs as I moved. It would have been hard not to walk like a woman!

Then as I neared the mall, the wind picked up. Of course, since my wig's grip on my head was already loosened, it threatened to come off. I panicked. I reached up and tried to tug it into place. That kept it from coming off but it didn't feel right so I turned around and headed back toward the car praying it would stay on. Suddenly the sensations which were so exciting before were frightening; the dress, the hose and the loose wig gave me a naked, open feeling. I finally made it to the car, confidence completely vanished, and fumbled with the keys, noting in my peripheral vision a family getting in their van in front of me.

I finally got the car door open and sat in the car, half in and half out, and tried to subtly adjust my wig in the rear-view mirror. I continued to feel uncomfortable and then realized that the family in the van across from me were staring at me open-mouthed! I'd never been read that openly before! Then I realized why. I was sitting in the car leaning toward the middle to look in the mirror. My right leg was curled under the front seat to support my weight. My left foot was propped up on the door sill thus placing my left knee high in the air! It wasn't high enough to give the family a beaver shot, but it was close to it! In my hurry and confusion I had just entered the car in a very masculine way, totally ignoring my dress, and totally puzzling that family, I'm sure. They didn't have outrage on their face or anger. Just literally open mouths and the most puzzled looks on their faces I've ever seen.

To this day I'm still not sure if they saw a man dressed as a woman, or a woman behaving very untypically. But at the time I was in panic mode, so I quickly got my legs in the car, shut and locked the door and started the car. The family started up their van and backed out. Now I was worried they would try to drive around and confront me, so I backed out in such a way as to exit the lot at the opposite end from the van.

My shopping plans totally out of mind, I slunk (if you can do that in a car), back to the hotel, snuck up the stairs, and into my room. That was the end of my outings for that trip. Since then I've been out many times, but it took me quite awhile to shake that experience. Now however, I have to laugh whenever I think about it; the looks on those people's faces and my unthinking reaction. And I still treasure the smile I received from that businessman!

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