A filly named Pipsqueak

8 years prior to the events of this story, Pipsqueak lived with his family in Trottingham. They moved to Ponyville during the summer of that year, and Pipsqueak celebrated his first Nightmare Night. During Nightmare Night, Pipsqueak met Luna for the first time. Luna knew that he was a fan, and she felt happy knowing that ponies like him could appreciate the night. She felt happy that ponies like him could appreciate her.

However, Luna never thought she would interact with him more than just that one night. Soon after the celebration, Pipsqueak started to write letters to the princess. A year passed and the two ponies had become close friends, sending letters back and forth to each other constantly.

Then, a disaster happened. A creature from the Everfree Forest had made its way into Pipsqueak's home. Upon being discovered by Pipsqueak's mother, the strange creature attacked the mare viciously. Hearing the screaming, Pipsqueak and his father both entered the room where his mother was attacked. His father grabbed a knife from the kitchen and charged the creature, cursing it for killing his wife and endangering his child. The creature managed to claw open Pipsqueak's father's chest, but the stallion managed to stab the creature with the knife before collapsing onto the ground.

Pipsqueak looked on in horror. The creature was wounded, but still capable of killing him. It slowly inched closer, but before it could get close to Pipsqueak, a flash of light appeared as some magic burst through the door and blasted the creature away. It hit the wall with a wet thud before sliding down. Twilight Sparkle and Rainbow Dash stood there in the doorway, the beast blown against the wall.

"That's the last one, time for a head-count." Rainbow Dash said.

Twilight looked around the room and gasped when she saw Pipsqueak's parents. His mother's head was crushed and parts of it were sliced off, her neck almost non-existent in the front, and her heart appeared to have been torn out. His father lay on the floor, all his internal organs spilling out of his chest.

Pipsqueak was still frozen in shock.

"Rainbow Dash, grab Pipsqueak and let's get out of here. We need to let the others know that we had two fatalities tonight."

The pegasus grabbed the colt and took him with the to the Town Hall, where the rest of the elements of harmony were gathered.

Pipsqueak was sent to the Ponyville orphanage, where he continued sending letters to Princess Luna.

Many years passed and Pipsqueak heard about a school started by Luna in Canterlot that helped fillies who had lost their homes still get decent education. It accepted all races and all ages. Pipsqueak had lost his home. After Rainbow Dash and Twilight Sparkle left the house, it combusted into flames. The cause of the fire was never known. Pipsqueak figured he'd be able to convince Luna to let him stay at her school.

Even though the chances were nearly non-existent, Pipsqueak went to the school and took an entrance exam.

Thankfully nopony noticed him being a him while he was there, but that was mostly due to his wearing a cloak over his body. He had let his hair grow long in the passing years, so at first glance he looked like a she anyways. All entrants were taken to separate dark rooms, each with only a table, the test, and a light over the desk. This was to prevent cheating by isolating the applicants from one another during the testing.

Pipsqueak was prepared, however and his studying had truly come useful.He finished the test, signed it with his name, and then put the pencil down.

The lights went out for a few seconds, and when they came back on, the desk was bare. Many dim lights had also turned on, revealing a bookshelf. Pipsqueak had been told that once he finished the test he would have to wait a bit before the results came back, so he grabbed a book off the shelf and began reading. Once he finished several chapters of the book, there was a loud beep, and Pipsqueak was told that Luna would be in to see him shortly. Pipsqueak closed the book and put it back onto the shelf before waiting patiently.

This is where the story begins.

A mare's voice spoke in the darkened room.

"Well, Pipsqueak."

"Pip, ma'am."

The mare smiled. "Alright, Pip. Why did you apply to this school?"

The young colt gulped before answering. "Well, I really really like you and I would love nothing more than to be taught by you and your standards." A slight pause. "Uh-ma'am!"

Luna gave a chuckle. "Young one, there's no need for the formality. At this moment I am just the head of this educational establishment, of which you are not currently a part of. You and I are on equal ground here. If you were a student, such formalities would be necessary, but alas, you are not."

Pipsqueak nodded in reply.

"Young Pip, do you realize that this school is for fillies exclusively?"

"Yes."

"Then why did you still apply?"

"Because I figured I might as well try, even if the chances are slim."

Luna opened a folder on the desk.

"These scores are most impressive, in fact, I've only known five ponies to score this well."

Pipsqueak grew a slight smile at that. "I studied very hard for this test. I want to prove that I'm more interested in studies than fillies."

"And so you have." Luna closed the folder and placed it into a filing cabinet. "If you wish to attend this school, you must understand that because it's an exclusive school, you must be a filly to attend. I'll let you attend, but on one condition."

Pipsqueak beamed with excitement. "What is it? I'll do it, I promise with everything I am!"

Luna looked Pipsqueak in the eyes. "You must dress as a filly while here. You can not be discovered as a colt. If even one staff member or student complains about you, a colt, being allowed in the school, I will be forced to remove you from school grounds. If you still wish to attend after that, you must undergo a gender reassignment, understand?"

Pipsqueak couldn't care what he had to wear, he was happy. He jumped up and hugged Luna. "Thank you so much! You're the best princess ever!"

Luna blushed a little. "You begin school tomorrow. I suggest you begin moving in and getting dressed up before classes end. Wouldn't want your new roommate to find out your little secret on the first day."