The cross-dressing spy who never stops talking

It started with his mother’s favorite gown.

He was thirteen years old, planning his outfit for the upcoming gala. All the relatives would be there, and some government officials that the family funded. Sidney liked being around the relatives. They were happier that he’d been born than his own parents were. He walked from room to room pretending to have conversations with the most important aunts and uncles, imagining how they would perceive him. He practiced nonchalant waves and perceptive glances. They were all amazed at his social intelligence–and at just thirteen! Fat old generals and squinting second-cousins would whisper behind gloved hands while he chatted with the Commander-General of Salaise.

He made his way, thinking of this, into his mother’s closet. There was her sapphire blue evening gown. It was his favorite color; he couldn’t take his eyes off it when she wore it. No one could resist staring at the one who wore that evening gown. Sidney shed his knit pullover and slipped the dress over his head, buttoning the high collar up to his neck.

I want to introduce you to a character in my next novel-in-progress, a science-fiction collaboration that my writing partner and I have been outlining for the past few years.

The character’s name is Sidney. He’s a spy with notions of one day being voted king of the world. He loves crumpets and watercress sandwiches. He cross-dresses.

His flamboyance annoyed me quite a bit in the beginning. He never shuts up about himself. His journal is huge. If we were roommates I’d want to choke him and stuff him in a closet. As I’ve come to know him better, however, he’s deepened. I’ve realized that everyone has habits and personality quirks, and those quirks come from somewhere. Sadly, I can see a bit of myself in Sidney. When you first meet him he’s flamboyant and shallow. I don’t like thinking I have anything in common with someone like that. But he’s weird, and I’m weird. We both have reasons for what we do, and once I start to really listen to his story I understand him. I even sympathize.

In a small way, he’s like Gollum from Lord of the Rings. Gollum is a sad, selfish, violent character that I can’t help but find fascinating. There’s an internal struggle through his whole story, with the bad usually winning, but in those moments when the good emerges you see what he could be, and you love him for that. And you want him to make it, but he probably won’t. But you want him to.
That’s Sidney.

He grinned at himself in the mirror. The blue set off his blond hair and brought out the sapphire hues in his eyes. The skirt folded around his feet, hiding his trousers completely. All in all, he concluded, not a bad start. He congratulated himself for trying something no one else in his sphere had. Everyone that he imagined watched him congratulated him also, admiring his physique.

His parents were not so appreciative when they found him in the gown. His mother told him to buy his own dresses if he must wear them. She didn’t believe he actually would.

He did. And he wore them in public.

Short, button-up dresses worn over dress pants became his trademark. Of course, his friends and some of the younger relatives teased him at first. One day at school some boys marked him as an easy target, in his fuchsia overskirt and black high heels. Since Sidney was studying pressure points and joint manipulation, he easily threw his attackers to the ground with a grin and precise thrust-twists. He preferred this way of combat to boorish boxing, where men simply clubbed each other to a pulp.

In his last year of school, he was elected homecoming king and queen. It was nice, but he was profoundly disturbed, standing on the pedestal alone. Not because he was alone, but because for once he couldn’t say he was one or the other. He had everyone’s attention but not their adoration. And he had no one at his side to adore him and his achievement. Call it ludicrous, but Sidney didn’t want to be king and queen at the same time. It felt redundant.