Sister Lauren Cross was the perpetual head sister of St. John’s Catholic school since she was in her late twenties. She had once been a beautiful woman who was admired by men unfortunately those same men did their best to harass her for her affections until she ran away to a convent and become a nun. Since then, she’s known for being cranky, bitchy, and a general cunt to those not with XX chromosomes.

Her favorite punishment for young men is the petticoat punishment. The sister took a specific sadistic joy in humiliating the young men by getting the girls of the school to doll them up as pretty as they can be and having them look like that for however long Sister Lauren prescribes. However, there is one student that infuriated her no matter how many times he comes back for her punishment.

His name is Timothy Pierce, a small, feminine boy who makes constant big trouble. Nothing ever violent just petty. He steals someone’s thing here, he pulls the fire alarm there, graffitied the girl’s locker room there, and one time he put laxatives in the food on soup day then put an “out of order” sign on all the bathrooms. But every time, Timmy always admits his crime and takes his punishment almost enthusiastically.

This pissed off the Head Sister of Saint John’s Catholic School immensely. Nothing ever worked, no matter how many dresses or how feminine the dresses were, nor how much training he would do to become a proper young lady, he always looked so pleased with how he looked every time. It got to the point where he was ordered to dress up in a female uniform for the rest of the school year. That actually worked and for a while Timothy became Tasha and Tasha was a very happy, cheerful young lady.

Then the summer came and went, and Timothy came back rather different looking than before. His long hair was luxurious and vibrant, his face was a lot cuter without a single blemish or pimple, and his figure was a whole lot more feminine than Lauren remembered it. But, for certain, Timothy was back and he was back with a vengeance.

The first day... Hell, not even the first day, he immediately graffitied on a bland wall of the school an image of a man unzipping himself and a woman coming out of it. It was provocative, to say the least, though the art itself was beautiful, the fact it was put on the wall of the main hall was not. And just like always, Timothy turned himself in without even a fuss

So now he’s here, in Lauren’s office as Lauren continued doing her work while he waited. It was like this; the sister likes to compose herself and give the students time to think about what they did wrong. The silence was oppressive. Or it would’ve been oppressing if Timothy wasn’t vibrating in his chair with excitement as though he was waiting for this moment.

Lauren didn’t know what to do about the small, delicate boy vibrating excitedly in the chair in front of her. She couldn’t understand why a boy would want to be dolled up into a girl and forced to humiliate himself in front of his peers. But she knew she couldn’t keep doing this. The parents have been protesting here for exacting the petticoat punishment upon other students. Claiming it was too "old fashion” and “Not very punishing” considering that Timothy shrugged off the punishment like oil to water and the boy had become a legend not just in school but out of school too as children go home to their parents for holiday and summer vacation and tell his tale of confidence and bravado.

Sister Lauren sighed as she sat back in her comfy office chair and tapped idly on her thigh with her finger. She observed the boy who was beginning to calm down from whatever excitement he was experiencing.

“There will be no petticoat punishment.” Her words cut through the boy like a scalding hot blade through butter. One second, he was all cheerful smiles, and the next second he looked like his favorite puppy just got crushed by a delinquent wielding a cement block in front of him.

Timmy’s crushed, beautiful, cornflower eyes met Lauren’s hazel and for the first time in the head sister’s life, she felt guilty not giving a boy the petticoat punishment. And for another first in the head sister’s life, Lauren got up went around the table, and pulled the now crying boy into an embrace. It was rare for her to touch anyone but herself spare the rare emergencies or when giving punishment.
“Ssshhhh, it’s okay. It’s okay.” She whispered to the sobbing boy as he let it out on her shoulder.

It was a time before the boy regained enough composure to speak, “Why?”

Lauren was a little confused, “Why what?”

“Why can’t you give the punishment?”

Lauren nearly laughed at such a question but she held it in, “Some of the parents don’t like it too much and the school board agreed. So, I can’t give it anymore, or else I’ll be in trouble.”

“Well, I like it.”

Now Lauren couldn’t help but titter at such a sentence, “Why is that?”

“Because... ‘cause.” Timothy’s voice became soft and he looked away. Then he mumbled something that Lauren couldn’t quite hear.

“What? I couldn’t hear that.”

“I want to be a girl.” The answer was quiet and tiny but all the pieces fell into place. Suddenly, Lauren realized that Timothy wasn’t getting into trouble because he was a trouble maker. He was getting into trouble because he was a she and...

“Oh.”

The realization hit her harder. She never gave Timothy the name Tasha. Tasha picked it out herself. All the lady training Tasha’s been doing, all the dresses Tasha would enjoy, all of it suddenly made a lot of sense. Now, Lauren have heard of transgender people before but always thought they were unnatural sodomites destined for hell. But the word became more defined in her head as the epiphany came to her. It wasn’t unnatural sodomites destined for hell. It was young men and women like the crying girl in front of her. Normal people who live usual situation that’s hard to understand.

“Tasha?” The sister called softly to the girl in front of her.

The girl’s eyes regain that cheerfulness it had before Lauren delivered the devastating news. “What?” The sister knew right then what to do.
“Would you like to be Tasha all the time?”
“Can it be forever?”

Lauren smiled, “It can be forever if you want it to be.”

The girl squealed and the head sister knew she made the correct choice. Though Tasha had to be punished as per school rules, the young woman became the cheerful girl she was the year before and only committing some rule violation sometimes. Tasha was an inspiration to many of the closeted kids within the boarding school and set up a Gender and Sexualities Alliance within St. John’s Catholic School, being one of the first religious schools to allow such a thing.

Lauren educated herself about the LGBTQ+ community after that and became an activist and religious figure within the community. When the school dismissed her years later, she went on to marry a woman named Jane Harlow. She settled down in a cottage by a lake with Jane, still keeping contact with Tasha to this day.

The End

I hope you all enjoyed that! It's been a while since I posted anything here and I thought you all would enjoy a subversion of the force feminization cliche that I see often

As always, have a happy happy day! Or night in my case hehe