Wigtown Wanderers

Chaser 1

Prompt: Cross Dressing Write about someone dressing as another gender.

DISCLAIMER: The transgender character is not the cross dresser in this story. If you think that, you can leave right now. Yes, even if you're the judge.

Additional prompts: 1. Uncomfortable; 13. Word count: 1616; 14. Theodore Nott

Word Count: 1616 (According to Microsoft Word)

Challenges: Slytherin MC (x3); Short Jog; Advice From the Mug; Ethnic & Present; Old Shoes; Interesting Times; Flags and Ribbons; Pride; Themes and Things A (Friendship); Themes and Things B (Risk)

Space Address: Liberty/Freedom

Warnings: Misgendering

DISCLAIMER 2: I am not transgender but I have dealt with misgendering for years. If you are a transgender person and the way I represent this character offends you, please let me know and I will do my best to fix it.

~o0o~

All things considered, Theo Nott considered himself lucky. Before he was even born his father had always wanted a son and had taken three wives to ensure that was what he got. The first two bore him no children and were divorced once they were no longer of childbearing age, with handsome allowances to keep the family mysteries a secret. Mr. Nott was old when he married Lucienne Conwyn, but she was the only one of his wives who carried their child to term. When she gave birth to a daughter, Mr. Nott was displeased, but figured he could at least set up an advantageous marriage. Perhaps hope the next child was a son.

That is… until the child demanded to dress in boy clothes and be called Theodore.

This got Mr. Nott thinking. He wanted a son and this child wanted to be a son. So he would indulge and raise her—him as the next in the Nott line. Continuing the line could be figured out later. It was rare for a Death Eater to have this line of thinking, but the amount of people trying to put Theo in dresses was down to zero, so it was absolutely fine by him.

From age three, he had been presented to the other pureblood families as Theodore Nott.

At age seven, his mother died in childbirth. Neither she nor the baby survived. She gave birth too soon.

After that, it was just Theo, his father, and their house-elf. Mr. Nott took to ignoring him and often sent him away to the Zabini house where Mrs. Zabini would tutor pureblood children. If she knew Theo's birth name, she didn't say it. As he grew older, Theo was less certain of what it was himself. Not that it mattered. Why would he want to remember the name that wasn't right for him?

When his Hogwarts letter arrived, he was half-surprised to find that his chosen name was on the letter rather than his birth name.

Mrs. Zabini brought him and Blaise to Diagon Alley to get their school things as well as get them fitted for their robes. Madam Malkin seemed to know everything clothing related. She could guess your robe size the minute you walked through the door of her shop. Most students were fitted on a pedestal in plain sight, but she took one look at Theodore and motioned for him to follow her into the back room.

"Alright, my dear," she said as she measured him. "As you get older you will be going through some changes."

Theo flushed and shifted his feet from side to side.

"I have no clue what you mean," he said. "I'm a boy. Always have been."

"Of course," she said. "But your mother left special instructions to me before she died. We were friends, you know."

"I didn't."

"Oh, well, now you do." She disappeared a moment and brought back several shirts. "I've been speaking to people who are like you, mostly out in the Muggle world. It has led me to design these shirts. As you… develop… these will give the appearance of a more masculine physique. You're too young right now, but when you're ready for them you can come in or even write me. Okay?"

Theodore looked in the mirror and chewed on his cheek.

"You won't tell anyone will you?"

"On my honor as a seamstress," she said.

And when the time came, the shirts worked. No one ever suspected a thing. All the teachers knew him as Theodore and by the time he reached his fifth year only two people knew the circumstances of his birth: Blaise Zabini and Slytherin prefect, now Head Girl, Tabatha St. Vincent.

Theo's plans to quietly move through school unnoticed and then finally hide away as an Unspeakable were shaken when Umbridge came around.

Contrary to popular belief, most of the Slytherins hated her just as much as the other four Houses. Theodore had no idea why Draco and his gang sought to be on her good side. Umbridge was an imbecile.

But she was an imbecile with connections.

An imbecile with connections that directly affected Theo. He thought she would just be after Harry Potter, but it seemed anybody who went against the status quo was on her shit list.

Besides… Harry was right, You-Know-Who was back. Theo's father told him so himself and warned him to keep his head low. And even if You-Know-Who hadn't returned then there would be other things they needed to defend themselves from. Tabatha St. Vincent firmly believed that Harry had only seen a You-Know-Who copycat.

Of course, Tabatha took it hard because Cedric Diggory was her best friend. So people saying that he died because of an unfortunate accident drove her mad. Theo wasn't sure if it would be kinder to tell her the truth or to just keep letting her believe it was a copycat.

Apparently, the entire Seventh Year nearly got detention with Umbridge because they refused to be treated like five-year-olds when they had N.E.W.T.s to prepare for.

But back to Theo's problem.

Umbridge was an imbecile with connections. Her connections granted her the ability to make new school rules and be the High Inquisitor of Hogwarts. If she saw something unsatisfactory, then she had every right to change it and in her eyes, Theo was one of the unsatisfactory things.

"Nott," she said after class one day. "Please, see me at my desk."

"I'll wait for you," said Blaise.

"Thanks, mate."

Theodore approached the pink-clad woman and stood a safe distance away.

"Come closer."

Theo gripped the straps of his book bag and did so. Umbridge gave him a sweet smile.

"I make it a point to do research on all my students," she said. "Separate the troublemakers from the ones with potential to make trouble. And I found out something very interesting about you Miss Nott."

Theodore felt shock as if he had jumped into the Black Lake in December.

"Wouldn't it be so much nicer not to pretend to be a boy anymore?" Umbridge continued and placed a hand on his shoulder. "A lovely young lady shouldn't need to hide."

"I don't know what you're talking about," said Theo, stepping away uncomfortably. "I am a boy. I always have been."

"I see," said Umbridge. "Miss Nott, you will dress in attire appropriate to your gender."

"The way I see it I already am," Theodore shot back and hurried away before she could say anything else.

Blaise was waiting for him across the door. Theodore grabbed his arm and hurried away with him.

"She knows," he said. "Umbridge knows a—about me. I don't know how, but she does."

"How?" Blaise furrowed his brow. "I thought only you, me, Tabatha, and Madam Malkin knew. Why would the toad woman have that sort of information."

"I don't know, but I'm scared Blaise. Do you know what some people here will do to me if they think that I'm a girl pretending to be a boy?"

Blaise nodded. "I'll write to my mum and see if she can hold Umbridge to secrecy. There has to be some law against outing students."

Theo thanked him and tried to push the thoughts from his mind. If he worried about it then he might end up getting sick.

The next day, he nearly did. When he went to breakfast, Filch was hammering up another educational decree.

All students will be required to dress in the school uniform as per the student handbook.

Those found not abiding by this rule will receive detention.

"She's going to make me dress in the girl's uniform," Theodore whispered to Tabatha. "I know it."

Tabatha grinned. "Maybe not…"

"Tabatha, the rule is right there," said Theo anxiously. "What am I going to do?"

She pushed her glasses up her nose and grinned at him.

"Well, lucky for you I studied the Hogwarts handbook forward and back."

"There's a handbook?" Blaise asked.

"Oh, yes. Now, Theo, I'm not going to tell anyone the real reason why we're doing this, but if you're okay with it I'm going to pull the ranks."

Theo looked at her skeptically.

"What are we going to do?"

"Malicious compliance."

Umbridge called Theo into her office once more to claim she was giving him until Monday to start dressing like a proper lady. This was in front of Harry Potter. Being outed chilled Theo's blood, but Harry Potter seemed all too entirely wrapped up in his own thoughts to even double-take. Theo promised he would be in proper uniform and Umbridge grinned at him as if she believed she won.

Come Monday, everyone who was in on Tabatha's plan met in the Hufflepuff Common Room. It was the biggest space, and also home to most of the students joining the protest. Tabatha had a lot of friends in Hufflepuff.

"Theo, tell me," said Blaise, turning around in the skirt. "Is my seam straight?"

"Yes, it is straight."

"You know," Blaise continued. "I wasn't sure I'd like wearing a skirt, but actually putting it on is rather freeing."

"Well, I'm glad you think so."

"Come on everyone," said Tabatha. "Umbridge should be at breakfast by now. Let's all go show her exactly how we follow the rules."

They cheered and paraded up to the hall, the girls in trousers and the boys in skirts. There were about a hundred of them which Umbridge definitely wouldn't be able to ignore. When she saw the spectacle, she screeched her head off and demanded to know what they thought they were doing.

Tabatha stepped forward with a book in her hands.

"Well… according to the handbook…"