The Arrogance of Youth

The youth was excited. Today was to be the day that he had been longing for. It had been a few years since he first wanted to cross-dress. He had bought a few things while he was at his last college but had had been at this one only a few months.

Here, he had not socialised a lot, still working out the layout of the social strata. His main associates, so far, had been other guys from commercial backgrounds. His own family was in property development, and the others who spoke to him were all well-built and usually bullies, like his father. He didn’t bother them, so they had left him alone, but had, at least, been friendly.

That was the problem. He craved for attention, for admiration, for respect, but didn’t have the aura of command. The fraternities here wanted nothing to do with him, so it had been a surprise when he had been invited to a party, organised by the Zeta house on Locust Walk. Perhaps they had realised what a worthy person they had missed, so far.

The invitation covered two of his desires, One was to be accepted by society, and the other was to do it in a dress. The event was to be a fundraiser and a ‘turnabout’ party after a meal at a restaurant, on Walnut Street.

In the week before the event, he had walked across the river along Chestnut, from University City to Fitler and the stores between Chestnut and Sansome, buying things that caught his eye, ‘for a girlfriend’.

On the evening of the event, he spent a lot of time getting ready. Of course, not trying things on meant that some things were loose, while others were tight, but he managed to have the proper underwear and the dress may have gaped a bit at the false breasts, but the shoes weren’t too bad. Before he put the wig on, he looked in the mirror to do his make-up. As this was his first time in public, he wanted it to be dramatic, a real night-time look. Finally, he was ready, and left his room to walk to the restaurant and his new acceptance among the upper crust of society.

He attracted a lot of glances as he approached the restaurant. At last, people were noticing him, or should we say, her. She felt alive, wanted and someone that she knew her parents would hate. She had an on and off relationship with her father, and wondered if the desire to be a woman could be her form of opposition to his bullying.

When she was close to the restaurant, she was stopped by a group of Zeta members, all dressed to kill. There was the college basketball star, a tall Afro-American with his girlfriend. Both looked like Amazonian Queens, as dark as the ace of spades in exquisite outfits and make-up.

Beside them were others. One was a Korean student, dressed in an Asian-looking outfit with a stranger that stood behind him with his arms around his waist. There were others, from many sections of society, a society made up of immigrants who had done well for themselves. There were a couple of stunning blondes who he knew were studying law. The basketballer smiled.

“Well, I never, who are you?”

“I’m Donna. Charles invited me to join you.”

The group snickered as one.

“Oh! If you’re talking about Charles Four, he’s our resident prankster. Did he tell you that we’re looking for new members?”

“Yes.”

“We are, but not someone who looks like they’re a streetwalker from the South Bronx. You look like a hobo who woke up next to a dumpster and raided it for clothes. I know, we’ll call you Donna Tramp!”

They all laughed, and the Korean spoke.

“Go away, ho. We pride ourselves on doing things properly, taking care to look right. You’d never fit in with us. Tonight is a simple test to see if applicants have the attention to detail that we insist on, but you’d never pass as a woman on a moonless night in a fog. You have no idea of what it takes to be a woman, it’s not something that you just throw money at. You need to have commitment, something that obviously eludes you.”

Donna turned away, tears in her eyes. She shuffled back to her room, humiliated. She vowed to dump all of her stash and never wear a dress again, even after the hundreds of dollars she had spent trying to look her best.

That night, in bed, the youth decided that he would get his revenge on the blacks, the Asians, the immigrants, the queers, the lawyers and the society that shunned him, even if it took another fifty years or more. And it did.

Marianne Gregory © 2026