A filly named Pipsqueak

by Shred_Hexstring

Rating: mature
Tags: Slice of Life
Length: 7866

Princess Luna accepts Pipsqueak into her own school in Canterlot, but first, Pipsqueak must abide by certain rules.

Princess Luna accepts Pipsqueak into her own school in Canterlot. Unfortunately, the school is for fillies only, so in order to attend, Pipsqueak must pretend to be like the other fillies, and hopefully not get caught by the staff or students! Will this be heaven or hell for him, and will he come to like being who he must become?

Rated mature for sexual themes later in the story.

Published 1970-01-01 00:00:00 UTC
Last updated 2013-12-19 20:58:10 UTC

Acceptance

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."

First Day

"And this will be your fourth period classroom." Luna said as she walked by a door with a musical note on it.

Pipsqueak followed along, making mental notes of all the classrooms.

"And over here is the foreign culture classroom, which appears to be open, I'll introduce you to the teacher." Luna said as she led Pipsqueak to the open door.

"Miss Turner, I'd like to introduce a new stu-oh my! What happened to you?"

A young white pegasus filly with a short pink mane was sat at the teacher's desk, and appeared to be grading papers. "Ah! Gomenasai! Miss Luna, I forgot to tell you! There was a bit of an accident in the aruchemical studies lab when a student tripped and knocked a potion out the window. It wasn't compureted yet and it broke on my head, making me appear as a filly."

Pipsqeuak looked to Luna at the strange accent this pony had.

"She's from Neighpon, she teaches this class."

Pipsqueak gave an "ah" of understanding as the filly jumped down from her desk and waked over to him.

"Watashi namae wa Sakka-no-Kouma. My name is Sakka no Kouma, but you may call me Paige Turner. Sorry, still getting used to greeting in Equestrian."

Pipsqueak chuckled and introduced himself. "M-my name is..." Pipsqueak blushed and turned his head away slightly.

"Eeh?" Paige inquired.

"Pipsqueak. My name is Pipsqueak."

"Pureasure to meet you Pipsqueako. Forgive my accent, I sometimes let it slip and it makes some words hard to understand."

"It's okay, miss Turner." Pipsqueak assured her.

"Well, now that we are all acquainted with one another, I believe we should be moving on. Have a nice day, miss Turner, and I hope you get better soon." Luna said

"Sayounara and thank you, miss Luna and Pipsqueak!" Paige responded

Luna and Pipsqueak left the room and continued down the massive hallway towards a set of two large open doors. The hallway was mostly golden with marble floor tiles and massive marble pillars reaching up to the ceiling. The ceiling was decorated with all sorts of gems arranged to make a long picture of the zodiacal constellations.

Pipsqueak's attention was pulled from the beauty of the halls by Luna's tour of the school.

"And here's the cafeteria..." Luna continued.

Musical

"AAAAAAALLLRRRIGHT CLASS! So who can tell me the difference between to two songs you were supposed to listen to last night?" The music teacher said. She was none other than Vinyl Scratch, a popular DJ in Equestria. From what Pipsqueak heard, Vinyl Scratch and some other pony named Shred had some thing going on where they would never tour at the same time, just so that they could teach this class.

"One was in minor and the other in major?" a green coated filly answered from the back of the room.

"Correcto! And in what keys were they?" Vinyl asked the filly.

"G major and C Minor."

"Once again, that's is correct! Drizzle, you are on FIRE today! Okay, now everypony grab your instruments, new kid, grab a mallet, you're on the timpani today, I'll talk to you after class about finding you an instrument if you want a different one. Oh! That's right! Class, we have a new student, and her name is Pipsqueak. Can we all give her a warm welcome?"

"Hello, Pipsqueak" The class said in unison.

Pipsqueak blushed a little, not being used to the attention while wearing filly clothes.

"Kid you know how to keep a rhythm?" Vinyl asked Pipsqueak, who nodded in response. "Well okay then, lets get started. And Pipsqueak, all you have to do is match the beat, you can join in when you're ready. Just follow the lead of the filly on your left, your notes are one quarter note after hers, got it?" Pipsqueak nodded again. "Good! then let's begin!"

Accident

WARNING! This chapter contains light watersports. If mentions of urine offend you, do not read any further and then complain. I mean, I gave you fair warning, so if you read on, I'm not sure what you'll expect. If it wasn't a young desperate colt who can't hold it in and lets his pee out you were expecting, you may need to get your head checked.

YOU HAVE BEEN WARNED!

You have the option to skip this chapter as it isn't too important to the rest of the story. same goes for the next two chapters.

The band was in the middle of rehearsing their third song when Pipsqueak noticed he had to pee.

Pipsqueak shuffled his hind legs a little to try and alleviate the pressure in his bladder.

"Okay, violins, cellos, and basically all the string section, lets do that part again. Some of you weren't getting the feel of this part. You have to think of a calm, slow moving, gentle river, then a grand majestic waterfall, followed by the rapids, rough and fast, crashing into rocks, wild and dramatic, and then peace again as the river settles back down, ya hear me? Soft and easy on the first 4 measures, then hold that high note for the next couple of measures before letting the power flow through those low notes while slowly getting softer and softer." Vinyl explained.

Pipsqueak felt a shiver run down his spine as his bladder gave him another warning.

The string section started to repeat the section of the song while Vinyl commentated on their performance.

"Remember ponies, flowing river"

Pipsqueak gulped. This wasn't helping.

"flowing..."

Son of a-

"...river..."

Nonononono-Pipsqueak's thoughts were interrupted by the sound of liquid spilling onto the floor. He knew what it was. He had just peed himself. His face went red and he put his front hooves into his face and cried.

"Uhh- Hold on, students. I'll take care of this." Vinyl said as she levitated a towel over the where Pipsqueak was and dried the floor up. "Come on, kid, let's get you to the nurse's office."

Pipsqueak was so upset by the fact he just had an accident that he didn't respond. He simply curled up into a ball and cried.

The rest of the students all had faces full of concern, as Vinyl carried Pipsqueak on her back and left the room, leaving the students with a "Don't blow anything up while I'm gone, kiddos."

Pipsqueak cried all the way to the nurse's office.

"Hello, miss Scratch, what seems to be the problem?" the nurse asked.

"Nothing too bad, nurse Cat. This filly just had an accident in class and I came here to clean her up." Vinyl answered.

"Oh, okay, well, take the room in the back, there should be everything you need there."

"Thanks, Kitty." Vinyl responded with a wink.

Pipsqueak didn't even notice, as he had tuned out the rest of the world for a bit while he cried.

Vinyl closed the door and put Pipsqueak on the exam table before slowly brushing his mane. "Hey, kiddo, it's alright. don't worry."

After five minutes, Pipsqueak started to calm down and stopped crying. "Wh-where am I?"

Vinyl smiled. "You're in the nurse's office, I'm gonna get you cleaned up, I just wanted to let you finish letting your emotions out first."

Pipsqueak wiped the tears from his eyes. "What do you mean by 'get me cleaned up?'"

"Well first we gotta get you out of those clothes and into some clean ones, since you had that accident."

Pipsqueak's eyes went wide. If he had to take off his clothes, he'd be discovered for sure. He had just screwed himself. He froze up in fear. It was over. His first day and he was about to be discovered. Pipsqueak laid down on the table and started to cry again.

Acceptance II

"Look, kid, I couldn't care less about what business you have going on down there, if Luna let you into this school in the first place, you must be something special to her. Besides, if you want to identify as a filly, who am I to argue? You are who you want to be."

Pipsqueak looked at Vinyl with wonder in his eyes. "You- you aren't going to..."

"Of course not! What harm is you being a colt doing to me? None, that's what! And hey, at least with that diaper on, even if you do get 'excited' nopony would be able to look and think you're a colt."

Pipsqueak's face turned beet red. "Y-yeah. I really hope I don't have to use this."

"Nah, don't worry about it. I'll get the nurse to write you a note so you can go to your dorm early. You don't need to deal with much more embarrassment today. You'll only be required to wear the diapers in the halls of the school until the end of the week. School policy for having accidents. It's also policy that I have to give you this 24-pack of Silly Filly diapers. Sorry, but you aren't allowed to wear panties in the halls again until you've used all these diapers up. Again, I know it's embarrassing, but it's for safety reasons." Vinyl explained.

"Thanks, miss Scratch."

"It's okay, kiddo. And don't worry, your secret is safe with me." Vinyl reassured Pipsqueak.

Pipsqueak gave Vinyl a hug. "Thank you so much!"

"Really, it's no problem. I may be a party animal, but I'm still a teacher. It's my job to look out for my students and keep their problems between me and them. Given, of course, their problems aren't endangering anypony. Now then, let's get going, I need to make sure the other fillies haven't demolished the classroom while there's no teacher."

They both laughed at this as they left the room.

"Was everything alright?" Nurse Cat Scan asked.

"Sure thing, Nurse Cat." Vinyl responded.

Nurse Cat Scan looked at Pipsqueak, who's face was still red. "Oh sweetie, it's okay. It's happened before, you don't need to be embarrassed. Many fillies your age have accidents. Still, I'm so sorry you had to go through all that embarrassment."

Pipsqueak's face grew one more shade of red. "It's okay, I'm over that now. It's just..." Pipsqueak turned his head to the side a little.

"Oh, the diapers! I'm sorry, but it's school policy that you have to wear those. Don't worry though, nopony will see them, unless you want them to, though you will have to check in with me after every period to see if you're not wet or..." This time it was the nurse's turn to blush. "...Or messy."

Pipsqueak's face could not be any more red. Pipsqueak was embarrassed simply at the thought of pooping in a diaper like a foal. "I'll make sure I'm dry and clean every time I do come in."

The nurse chuckled before letting Vinyl and Pipsqueak go.

As they walked down the hall towards the dorms, Pipsqueak noticed his gut rumbling. "Um, Miss Scratch?"

"Yeah, kiddo?"

"I have to poop."

"Oh, well the bathrooms are all right he-" Vinyl stopped as she saw where the bathrooms were. "Out of order?!"

Pipsqueak's eyes started to water. "No. I don't want to poop myself like a foal." Pipsqueak started to cry.

"Kid, we're almost to your dorms, just try to hold it until we get there, okay? You can do it!"

Pipsqueak wiped the tears from his eyes. "O-okay."

The two managed to get to his dorm. "See ya tomorrow, kid. Hope you're feeling better by then. You take care, alright?"

Pipsqueak opened his door before responding "I will, miss Scratch."

optional chapter: Feelings

WARNING! This chapter involves diapers and the use of them, as well as clopping in said diapers. If this is not your thing, skip past it, this is the only chapter with that content. I apologize for the content.

The fetish/clop scene is only in here to appease those who followed me for stories involving that particular fetish.

Again, I apologize if that is not your thing.

Pipsqueak closed the door before rushing to the bathroom. He opened the door and walked in, but could only take a few steps before he felt the pressure become too much. His gut began to hurt. He doubled over in pain right in front of the toilet. He started crying as he felt the mess slowly pushing through out of his anus. "No. Please, no. Not when I'm so close." Pipsqueak realized it was pointless to fight it, as it was much too late now. He let go and felt the mess fill his diaper. What little was left in his bladder released itself as he lay there, sobbing in shame.

That was when he felt something. He felt a tightness against the front of his diaper. Was he turned on by this? Suddenly  his body was overcome with a heat. He got up and felt a little woozy. He made his way over to his bed where he lay down on his side. He rolled over and felt the warm mush spread along his backside. His excitement grew, his heart started racing, he had never felt this before. He knew what it was, and what to do, he had heard about masturbation. His hoof slowly reached towards  the front of his skirt. He pulled it back and saw the faded teddy bears on his pink diaper. He put his hoof on the front, where his penis was.

His mind was lost. In that moment pure desire kicked in. He started slowly rubbing in circles, eliciting moans of pleasure. He started to rock his hips back and forth in a humping motion, making the mess smear along his backside even more. He wanted to feel this to it's full effect, so he forced himself not to shoot his load, he sat up, put his hooves behind his back, and imagined being hoofcuffed and gagged, rocking his hips back and forth, moving the mess back and forth, feeling the warmth slowly move in and begin to coat his member. He muttered to himself under his heavy panting, "Ohh, dirty filly, still messing your diapers like a foal. So messy..." His muttering eventually stopped as his pants got heavier and heavier, and his hips started rocking faster and faster. He was lost in a world of pure pleasure, and what little left of his bodily control went to trying not to cum, though it was proving to be difficult.

An entire Half hour passed like this, his balls swelling every second with more of his seed, waiting to be released, while he continued rubbing his diaper against the side of the bed. Eventually it became too much and he had to release. Hooves still behind his back to simulate being bound, he leaned back and let loud a scream of ecstasy as he experienced his first orgasm. The moment seemed to last forever as his seed kept coming forth, stream after stream. He kept cumming for 2 minutes, making his diaper soaked once again, this time with his semen.

As his senses came back to him he collapsed onto his bed and instinctively grabbed his Luna plushie before it hit him what he had just done.

"I-I just..." He felt himself start to cry again. "I just peed and messed a diaper... and I liked it... a lot... and I..." He broke down. He couldn't believe he had just rubbed himself off in a dirty diaper. He pulled the blanket over him and cried until he eventually fell asleep, still in his pee, poo, and cum filled diaper. While he slept, he had a wet dream and filled his diaper with cum once again, some of it leaking out of his diaper and onto the inside of his skirt.

Secrets

This chapter will not focus on the fetishes from the previous three chapters, but the main events of those chapters will be referenced in a manner so that you will understand what happened, to a small extent.

Pipsqueak woke up later to Trixie throwing some trash away. That's when he remembered what he was wearing. With a blush he look under his skirt to find that he was wearing... a clean diaper?

"It seems you are awake, and you had a Great and Powerful accident yesterday, roommate. Don't worry, I cleaned you up, and your secret's safe with me." The narcissistic unicorn said. "You aren't the only one who's pretended to be something they were not. Then again, telling the truth would have actually helped in my case."

Pipsqueak's eyes watered a little.

"Oh please, don't start crying. There's nothing to cry about. I know you're scared but somepony from Ponyville once taught me that fear isn't something to cry at, it's something to laugh at."

Pipsqueak looked up at Trixie.

"Then again, that mare was a bit off her hinges, but she was off her wheel, and that's good, because that means that she and the wheel are no longer a thing and Trixie doesn't trust wheels, so Trixie trusts others who don't trust wheels."

At this, Pipsqueak began to look a bit confused.

"The point is Trixie understands. Trixie doesn't understand what it's like, but she understands, and she will help you through the next couple of weeks with this issue."

Pipsqueak smiled and hugged the mare. "Thanks, Trixie."

"The Great and Understanding Trixie will do her best to be there for you, roommate."

Pipsqueak then realized he hadn't actually told Trixie his name. "Um, my name's Pipsqueak."

"The Blunt and Observant Trixie finds that an appropriate name given your penis size."

"HEY!" Pipsqueak yelled, only the laugh at the comment. "Okay, yeah, it is a little small, but I don't really care."

Trixie smiled. "Good! The last thing Trixie needs right now is to help somepony else with their self-esteem issues. The Great and Powerful Trixie has enough self-esteem issues of her own."

"Trixie, how can I be sure you'll keep my secret safe?"

"Because Trixie has many secrets of her own, and she's kept them safe for many years." Trixie said with a wink. "How about Trixie treats you to some pizza tonight? Trixie wishes to make up for the fact that we've been roommates and we don't even know each other yet."

Pipsqueak smiled. "I'd like that."

Two months later

Pipsqueak had gotten used to the school routine, and thankfully never had another accident in class. He had just finished his fourth period class with Vinyl Scratch and was on his way to the cafeteria when one of the teachers for the advanced classes stopped him.

"Hello, young miss. May I speak with you for a minute?" The unicorn stallion said.

"Y-yes, Mr. Spark?" Pipsqueak responded.

"Follow me." he commanded as he led Pipsqueak into his classroom.

Once both ponies were inside, Pipsqueak noticed the blinds were pulled down, darkening the room. Before he could why they were down, Pipsqueak heard the door lock. He turned around and saw the teacher coat the lock with a magic barrier. Pipsqueaks face turned to one of horror as he realized something was very very wrong.

"Listen, Pipsqueak. I know your secret, and let me tell you something." Spark's face twisted into a disturbing smile that seemed to stretch across his entire head. "I have plenty secrets of my own, and I'm about to share one with you, little colt."

Assault

Pipsqueak opened his mouth as he was about to scream when a ring-shaped gag was forced into his mouth.

"Now, now, little 'filly,' we don't want to have to split the fun with everypony in the school now, do we? Besides, if somepony came running in, they might see your tool and realize you don't belong here."

Pipsqueak's pupils shrunk. The stallion was right. "Wha ah roo goon noo da me?" Pipsqueak struggled to ask.

The ring-gag was removed from Pipsqueak's mouth as Spark asked him. "I'm sorry, what was that?"

Pipsqueak asked again. "What are you going to do to me?"

The stallion laughed as he put the gag back into Pipsqueaks mouth. "I'm not going to do anything to you just yet. First, I'm going to have you do some things to me."

Pipsqueak felt himself being levitated in the air to the back of the room before he heard some jingling. He then felt something cold and metal close around his hind legs, forcing them apart. Then a wire was wrapped around the base of his tail and tied to the back of the strap holding his gag in place. Finally, he felt his front hooves being tied together as he was set down. Unable to keep his balance right away, he fell forward and, unable to pick himself up, he stayed there on the floor with his rear end sticking up into the air.

"Pick your head up, young filly!" Spark commanded, and Pipsqueak obeyed. He had no choice, and he knew it. "Now then, I have a surprise for you, but because it's a surprise, I can't show you, so we're going to need this." Spark pulled out a blindfold and forced it onto Pipsqueak's face.

Pipsqueak was scared. He knew what was going to happen, but he didn't want to accept that it was happening.

"That gag is to keep you from biting. Now start sucking!" The stallion demanded as he thrust his penis into Pipsqueak's mouth. Spark started moving his penis back and forth, slowly increasing his pace as he chuckled to himself. "I can see why Luna let you into this school. You suck dick just like a good filly."

Pipsqueak was mortified. He couldn't believe it. He was being raped, and he knew nopony could help him. Tears started to pour out from his eyes, rushing down his face as the stallion continued to force his penis down pipsqueak's throat.

Discovery II

Luna couldn't believe what she was hearing. Pipsqueak was absent from his 5th period class? He had never missed a class before, aside from that one time he had the accident. This concerned her. She left her office immediately after receiving the call from his 5th period teacher and started going to every teacher who was teaching this period.

Classroom after classroom, Luna was disappointed to find that none of the teachers had seen Pipsqueak during or after lunch. This continued for 11 classrooms until she ran into Paige Turner and Vinyl Scratch in the Teacher's Lounge.

"Miss Scratch, Miss Turner, I must ask something of the both of you."

Paige was the first to respond. "Yes, Miss Luna, what is it?" Paige asked, immediately followed by Scratch's response of "Sup, boss ma'am, whatcha need?"

"Have either of you seen Pipsqueak during or after lunch today?" Luna inquired.

"Can't say I have, Moon-booty. sorry." Vinyl said.

"I believe I saw Mr. Spark Nova talking to her in the hall."

Luna and Scratch's faces went pale.

Spark Nova was released from prison 5 years ago, after serving time for repeated raping of young colts.

Luna, without hesitation, asked "Where did you last see them, and when?"

Paige started to look worried. "I was on my way to the cafeteria when I saw her enter his classroom."

Luna bolted out the door.

"Miss Luna, where are you going? What's going on?"

Vinyl put a hoof on Paige's shoulder. "Spark Nova was convicted and found guilty of molesting several young colts."

Paige's face became one of shock. "But if he only molested colts, then he should be fine at an all filly school, right?"

Vinyl sighed. "Paige, I'm going to tell you something. I know you. You'd be okay with it, but I'm going to need you to not tell anypony, do you understand?"

Paige Turner nodded before asking "What is it about?"

"It's about Pipsqueak."

Penetration

"Alright, sweetheart, I'm going to need you to swallow this." Spark said as he put a pill inside Pipsqueak's mouth.

Pipsqueak struggled to swallow it, but knew he had. Otherwise, his attacker would get mad. Once he did finally managed to swallow it, the stallion pet his mane. "That's a good filly."

Pipsqueak noticed the effects of the pill immediately as a familiar heat flushed through his entire body. He felt his member grow tight in his panties.

"Let me get that for you" Spark Nova said as he used his magic to pull the panties down a little so that Pipsqueak's penis didn't strain too hard against them.

"You know, now that I think about it, maybe you won't need those after all."

Pipsqueak felt the panties being slowly pulled down his legs.

"I bet you liked wearing that soft cotton on your skin, but now I'm going to make you feel even better."

Pipsqueak knew what this meant. He clenched his butthole tight, trying to keep his rapist out, but lost his focus as he felt his flank get smacked by Spark's hoof. He gave a small yelp before he felt the stallion's large dick enter his body. It was painful, but the aphrodisiacs from the pill were working fast, and in full force. The only reason he kept his mind from being overtaken with pleasure was because of the shock of being raped.

Even so, Pipsqueak couldn't hold back his moans in between his sobbing. His anus was being torn apart by this stallion, and he was helpless.

"Quit whining, kid. I'm not even halfway in. Yet." Pipsqueak closed his eyes shut tight. He knew this was going to hurt.

Rescue

Pipsqueak had closed his eyes and braced himself for the pain to come, but it never did.

He held his eyes closed for what seemed like an eternity before he opened them, staring at the sight before him in disbelief. The knife was being held in the middle of air, stationary, and surrounded by a dark blue aura. The door was open, and Luna stood in the light.

"Nova!"

Spark turned his head towards the booming voice of the princess, fear filling his face.

"Release Pipsqueak this instant." Luna demanded.

"No. I'm not going back to prison. I'm finally free to do what I want! Nothing will stop me, not even a princess like you!" Spark shouted as he used his magic to levitate a set of knives into Luna. This trick did not go unnoticed, however, and Luna was able to grab the knifes and throw them back to Spark Nova, who teleported out of the way and charged the princess who effortlessly grabbed him with her magic and thrust him into the wall.

Spark Nova lost his focus and his magic cancelled, dropping all the knives and Pipsqueak onto the floor.

Spark started to speak. "You're a worthless princess, you know. Why would you attack somepony when they're simply handing out a well deserved punishment."

"Well deserved punishment?!" Luna yelled. "What is so well deserved about this?"

"Colts are not allowed in this school. I was just punishing him for lying to all of us before I fixed the problem." Spark responded.

"Was the rape part of the punishment as well?" Luna asked. Spark's eyes went wide. "And who are you to decide who is and is not a filly at heart? Who are you to judge and punish? Do not forget, you were only pardoned for good behavior because you were only convicted on a single offence. You do realize what repeat offences of your crime warrants, don't you?"

Spark started to plead with Luna. "D-don't send me back there!"

Luna smirked. "Pleading for mercy?" She leaned in closer. "Why should I show you any, when mercy you've countless times withheld?"

Vinyl scratch and Paige Turner burst into the room and ran to Pipsqueak. "Yo, Pips, are you allright?" Vinyl asked.

Pipsqueak could only cry and shake his head no.

Vinyl lifted the kid and placed him on her back while Paige grabbed the colt's bookbag.

"Thank you, both of you. Take him to his room, I will personally deal with this trash. Make sure you lock the door when you leave." Luna said, while keeping her gaze on Spark's face.

"Will do! Come on Paige, let's get him to his room." Vinyl said as the three ponies left the room, closing the door behind them.

Punishment

"Spark Nova, for the repeat offence of underage rape, you are sentenced to life in prison with no chance of release."

All light faded from Spark's face.

"Now, as for the crime of attempted castration, we have not had to deal with such crimes in over one thousand years, so we never saw a need to change this law."

Spark started to cry. "Don't do this! Please! NO!"

Luna's smirk fell into a blank stare. "Spark Nova, you hath wrought this punishment upon yourself." The princess used her magic and grabbed Spark's horn before breaking it, causing the unicorn excruciating pain. "I will not have any funny business while we do this, am I clear?"

Spark sobbed and nodded his head. His heart was pounding. He knew what was coming.

Luna levitated a knife and slowly brought it closer to Spark's testicles. She went as slowly as possible when slicing them, much to the unicorn's torment. Eventually, she cut the sack off, leaving the testes hanging.

"It is not often that we use this magic, as it is grotesque and incredibly dangerous, but this punishment truly warrants such measures." Luna said as she gripped the testes with her magic. Spark started to scream in agony as Luna slowly used her magic to implode his testes. Spark's cries did not affect Luna, however, as she continued to slowly crush the stallion's junk. After what seemed like ages, the balls finally burst in on themselves, and Luna finished her castration.

Spark dropped to the floor, curled up and continued sobbing and screaming in pain.

"I will leave you here until the guards come and escort you to the dungeons. I'm sure somepony who likes sex as much as you will make plenty of friends there." Luna said as she teleported herself to the other side of the door.

Guards came to pick up the sobbing mess of a stallion ten minutes later. Spark was sent to the Canterlot dungeons, put into stocks and was repeatedly molested by the inmates and force-fed/hydrated by the guards for the rest of his natural life. 58 years later, the stallion died of a heart attack.

Settling

Pipsqueak entered the dorm room where he would be staying and looked around.

"Huh, I expected a lot more pink." he said to himself as he noticed the light blue walls. He passed the bathroom and tiny kitchen to find a bunk bed. The top bunk had a purplish-blue bedspread with stars all over it's design.

" I guess I get the bottom bunk."

Pipsqueak started to unpack the suitcase that Luna gave him first. He found a pink bedspread with flowers all over it. He blushed. The pillows weren't any more masculine. He made his bed and then looked at the two dressers in the room. One was pink, the other was, surprise surprise, purplish blue with stars painted all over it. "Who in Equestria is my roommate?"

Pipsqueak opened the pink dresser and started putting his new uniform into it's drawers. Pipsqueak also noticed the school uniform also called for panties. He took one out and looked at it. It was yellow and had some orange and red flowers decorating it. He slowly started to put the panties on, blushing as he felt the soft cotton undergarments brush up against his butt.

After putting those on, and the rest of the panties away, Pipsqueak took out his uniform and put that on as well.

Once they were on, he took a look into the mirror. He blushed slightly as he realized he actually pulled off the look quite well, and he had to admit, he looked pretty cute too.

Pipsqueak made his bed and set his Luna plushie on the pillow.

He was finished unpacking his stuff now and ready for a nap. He got up early to meet with Luna, and the school was quite a long way from the orphanage in Trottingham. As he threw himself onto his bunk, he noticed something on the ceiling. Peeking  his head over the side of the bed, he saw it a giant poster of The Great and Powerful Trixie!!!(TM).

"Whoever I'm sharing this room with must be the biggest Trixie fan in all existence."

As he laid his head back on the pillow and hugged his Luna plushie, the door burst open to a mare in a robe and wizard's hat.

"The Great and Powerful Trixie has returned to her room for a great and powerful nap before she greatly and powerfully studies!"

Discovery

ATTENTION!

This chapter is not essential to the story and merely follows up on events in the previous chapter. Some content may not be appreciated by all readers. Reader discretion is highly advised.

You have the option to skip this chapter, and the next one, as they deal with fetishes that are not usually well received.

You have been thoroughly warned.

"Kid, stop crying, it's gonna be alright. Nopony's going to think less of you, and if they do pick on you for this, let me know and I'll give them the longest lecture they'll ever know." Vinyl tried to reassure Pipsqueak, not knowing the real reason he was crying.

"Now, I know this is going to be embarrassing, but there are no spare panties in the nurse's office, just spare uniforms and these diapers. Still, we had one accident today, and if something's wrong with your bladder, we don't want to risk another accident until we get you checked by a doctor."

Pipsqueak blushed furiously. If he was going to be put in a diaper, there was no possible way he wouldn't be discovered.

"Now lets get this skirt off." Vinyl said as she levitated the skirt off Pipsqueak. "Panties next." She continued as she levitated the panties off, all while looking through the cabinets in the room. "Aaand here they are! Sorry about the cutesey-wootsey designs on them, they're the only ones in your size, Pipsquea-" Vinyl froze mid sentence as she turned around. The sight that lay before her was not one she was expecting.

Pipsqueak started to cry again.

Vinyl just stared, unsure of what to do.

"Miss Scratch I'm sorry, please don't tell miss Luna I don't want to leave this school, it's only my first day!"

Vinyl shook her head and snapped out of her stupor. "I'm sorry, what?"

Pipsqueak wiped tears from his eyes again. "Miss Luna said that if anyone found out and complained to her that she'd be forced to remove me from the school." Pipsqueak looked at Vinyl, his eyes pleading her not to tell Luna about him being, well, a him.

Vinyl stared at him for a moment and then sighed. She levitated Pipsqueak's legs up and wiped down his nether regions with a wet wipe before placing the diaper under him. She let his legs down and then proceeded to finish diapering him. She then levitated the clean skirt over to him before saying something.

"Look, kid..."

Sweet Release

Pipsqueak was trapped in a world of pain as the stallion pushed his cock further and further in. His anus was torn asunder, and the blood only provided further lubrication for the stallion who was raping him. He could hardly breathe in between the sobs of pain.

Pipsqueak struggled in his binds, but to no avail. It would take a miracle to get out of this.

The anal torture was soon over, though, as the stallion released his seed into Pipsqueak.

The binds on pipsqueak's front hooves were undone, only to be redone behind his back. He felt himself being set down on his bleeding anus.

"Okay, Pipsqueak." Spark said as he removed the gag from Pipsqueak's mouth. "Be a good little filly and start sucking!"

Pipsqueak felt his back being bent by Spark's magic, and his face met with his penis. Pipsqueak had no choice, and he started to suck. He knew he didn't want this, but he sort of liked the feeling. He sucked slowly until Spark started yelling at him.

"If you don't cum in the next two minutes, I'm going to castrate you here and now. And make sure you swallow it all. one drop out of your mouth will get you punished as well."

Pipsqueak, in fear of this painful prospect, started sucking harder and faster, rocking back and forth to push himself closer so that he didn't disappoint Spark Nova.

After a minute of sucking himself, Pipsqueak came, releasing a large amount of semen into his mouth as he struggled to swallow it all before it overfilled his mouth.

Once it was over, he licked up any remaining semen off his cock before popping it out of his mouth, gasping for breath.

The gag was placed into his mouth once again, forcing it into an "o" shape.

"Alright, this should keep your pathetic little cock busy until I'm ready." Spark said as he positioned pipsqueak so his belly was on the floor once again. Spark then inserted a large vibrator into Pipsqueak's bloody anus before pulling his panties back up over the sex toy.

Pipsqueak's body has started rushing adrenaline by this point, losing it's ability to feel pain temporarily. His cock was hanging over the front of his panties and the tip was brushing against his skirt. Pipsqueak was left like this for 15 minutes before he heard the stallion get up and walk over to him.

The stallion shoved his cock through the ring gag once more before shouting "Round two, bitch!"

Round Two

The stallion forced his entire member into Pipsqueak's mouth, nearly chocking the poor colt, and started rocking his hips back and forth. Pipsqueak loathed every second of the stallion's cock sliding in and out of his mouth. He could feel the veins on the shaft with his tongue.

The stallion grabbed the back of Pipsqueak's head and increased the tempo of his thrusts, while also levitating a whip to smack Pipsqueak's ass.

SMACK!

Pipsqueak's nose started to run, leaking snot down his face alongside his tears. He struggled to free his hooves, twisting left and right, but it only increased the pleasure that this stallion was receiving.

"Ooohhh, what a good little filly you are, pleasuring your master like that."

Pipsqueak felt Spark's cock pulse and knew he was close to cumming. He started to lick the tip of the stallion's penis to get it over with as fast as possible. It didn't take long before Spark let loose a massive load down Pipsqueak's throat, almost chocking the poor colt.

He pulled his dick out, leaving a trail of semen stuck to his dick. "You messy filly, you left some yummy cum on my dick. Some of it even fell to the floor. I hope you left room for dessert, because I'm going to have you clean it up." Spark Nova stated as he undid the binds on Pip's front hooves.

Pipsqueak understood what Spark wanted and obeyed, sticking his tongue out and licking the floor, looking for the cum. Once he found a small puddle of it, he licked it up as quickly as possible.

"You missed a spot, little miss leaky pants~" The Stallion hummed.

Pipsqueak back up a few paces and stuck his head down, plunging his nose into a large pile of cum.

"You feel that? That's your cum, dripping from your precious little skirt. You should really be more careful when you cum, sweetie" Nova commented before giving Pipsqueak's ass another whip.

Pipsqueak's sobbing became louder as he licked up his own cum puddle off the floor.

"I said be quiet!" Nova burst out, giving Pipsqueak's balls a strong whip.

Pipsqueak yelped in pain and lost control of himself and just fell to the floor, crying.

"Look at you, you're crying like a filly. You might as well be one!" The stallion said as he removed the blindfold from Pipsqueak.

Pipsqueak, now with his sight returned, saw the stallion levitating a knife. Suddenly he felt himself being levitated into the air. His heart raced as he saw the levitating knife pointed towards his testicles.

Spark Nova grew a devilish grin. "And fillies don't have THESE!"

Pipsqueak saw the knife fly towards his balls, and then everything went white.