Retro Rerun: Crossdressed and Stranded

By Roberta Angela Dee

There was a period in my life when one could describe me as a crossdresser. My aspiration had always been to live and to work as a woman. However, before I summoned enough courage to make such a commitment, I would still go out dressed in the most feminine attire with the hope that I would be accepted as a woman and return home without the embarrassment of a police record.

I had been cross-dressing all of my life. I began at the age of 4-years old, continued through my teens, and even managed to secretly dress while living in a college dormitory. However, my feelings towards cross-dressing changed after I had graduated. As an adult, living on my own, I more than understood that the consequences of being discovered would be far more severe than had I been exposed during high school or even while at college. I was violating a sacred social taboo. I was a man wearing a dress — not just any dress, but a short, frilly and very sexy dress.

In fact, I can still recall the fear of stepping out from my apartment. My heart beat in my chest like an African drum summoning warriors to battle. I could almost hear its repetitive rapid thumps. Each step towards my vehicle seemed like an eternity: Would anyone see me? Would Mrs. Taylor be looking out her window? Would Sam Marshall recognize me wearing a dress, makeup and a wig?

People say life is more difficult for a woman. Perhaps they’ve never compared being a woman to being a crossdresser. A woman can walk the street and not fear her identity and reputation being destroyed. This is certainly not true for the crossdressed male.

Women can dress as masculine as they like, and one might suspect they are gay. However, they’re basically left alone. The worse they can fear is an ugly rumor. This is not so for a man. Caught in a dress, he suddenly becomes a pervert, a sexual deviant out to molest anything with legs. It’s unfair and certainly not logical, but it’s the society in which we live.

I start the engine. My heading is already fixed in my mind. Will I risk stopping for a soda at the local convenience store? Why not? I’ll only be a minute. “But it’s not yet dark,” I say to myself. “What if I’m recognized?”

“Don’t be silly,” I reply to myself, “What could possibly go wrong?”

I pull over to the convenience store, park, and exit from my vehicle. I display my best impression of a busy lady stopping for a drink before hurrying off to pick up her children or meet with her husband. There’s a man in the store, and a second man behind the counter. There are also two women.

I enter the store, select a Coke, and sashay up to the counter. I’m careful to avoid eye contact with the male customer, just as any woman would in a similar situation. But I smile at and I courteously acknowledge the female patrons. So far so good. One woman is in her early thirties, but the other is only about nineteen. The younger woman is likely to be more accepting should I be read.

“Would you like a bag, ma’am?” the clerk asks.

“Please,” I respond with a feminine voice and a smile. Women always smile when they ask for anything.

I accept my change, throw it into my purse, and exit the store. It had been a perfect event.

Now, I get back into my car and try to start the engine. It doesn’t turn over. I mean, it doesn’t make a sound. I’m instantly petrified. I don’t want to attract the man’s attention. I can’t leave my vehicle and try to walk home. I’m crossdressed and miles from my apartment. And now my heart is beating even more rapidly than before. I wanted to crawl under a rock and die!

I pretended to know what I was doing, as the male patron entered his pickup truck, backed out, and drove away. Then, I released the hood of the car and went to see if there was anything obvious that I could correct.

“What’s the matter?” a young female voice asked. “Can’t start your car? They’re such a pain. Aren’t they?”

“I know nothing about cars,” I answered helplessly, as I looked at the younger female patron who had been in the convenience store.

My helplessness wasn’t an act either. I knew nothing about cars, except where to put the key and the gas. Everything else about an automobile was a total mystery to me.

“Would you mind, if I take a look?” she asked.

“Oh, please! Would you be so kind? I’m too far from my apartment to walk back.”

She leaned over to look at the engine. She touched a few wires and left me with the comforting impression that she knew what she was doing. But then she said, “I don’t see anything wrong here.”

My heart fell into a bottomless stomach. I knew that this was the day I would die.

“Do you have it in gear?” she asked.

“In gear? What do you mean?”

“Let’s check.”

She opened the driver’s side door, looked in, and said, “Oh, you’ve got it in drive.”

She switched gears, then said, “Try it now.”

I got back into the car, turned the key, and it started up immediately.

“You just left it in drive,” she told me. “I do the same thing all the time.”

“Oh, thank you so much,” I nearly cried.

She lowered the hood and then said, “You just be careful out there, lady. A pretty girl like you wouldn’t want to get stranded in this part of town.”

I smiled, backed out and headed straight for my apartment. Perhaps, I’d go out the following night. But at that time, I was too nervous to do anything but return to the safety of my humble abode.

Reflecting on the event later that evening, I suspected that the young woman knew I was crossdressed. But by then it no longer mattered. The main thing was that she treated me like a lady, and I reacted like a lady.

For more than 30 years, I’ve been writing about the society and how we need to take a more open approach to gender. A man wearing a dress is not instantly depraved, nor is he likely to be a pervert. He’s just a male fortunate enough to be able to express a feminine nature more than most men would even dare. Is that so terrible?

The End

Tags: crossdressing, featured, passing

Category: crossdressing