Regression: Isekai of Equestria

by JackofEquestria

Prologue Chapter 5 (Last Edited: (4/27/2022)

June 5, 2020

Twilight Sparkle's Balloon

The events that had occurred in the past day had given Jack a lot to think about. He had been transported to another universe and transformed into a child. The inhabitants of the universe in question were colorful talking ponies with tattoos on their butts. There didn't seem to be any way back, and worst of all (at least in Jack's mind), he had been forcibly adopted and was going to have to go back to elementary school.

“I wonder what pony school is even like," he thought to himself, glumly watching the landscape of Equestria pass below him. “I bet Mom is worried sick about me, Dad’s probably just annoyed I’m taking so long, and Mark probably doesn’t care at all (not that I’d blame him.)”

"Are you alright, Jack?" Fluttershy asked, placing a hoof on his shoulder.

"I'm fine, Fluttershy," Jack lied.

"Well, if you ever need anything, just ask."

"Hey, Fluttershy! How about helping me pull!” yelled Rainbow Dash.

“C-coming!” Fluttershy replied.

As Fluttershy went to help Rainbow Dash, Applejack took the chance to start up a conversation, “Ah know yer nervous, but trust me, the ponies in Ponyville are the friendliest in Equestria."

“Are you deaf? I said I'm fine," Jack growled.

"Ah know what ya said, but it weren't the truth, now was it," Applejack said thoughtfully.

“What gave me away?” asked Jack.

“Yer not a half-bad liar, Jack, but it takes more than that to fool me," Applejack answered with a chuckle.

"I'll keep that in mind," Jack muttered.

They arrived in Ponyville just as the Sun was beginning to set. As soon as the balloon touched the ground, Pinkie raced off to God knows where the rest of the ponies made their way home.

"Are you ready, Jack?" asked Fluttershy.

"I guess so," Jack sighed.

After a few minutes of walking, they arrived at Fluttershy’s cottage. When Jack walked inside, he was amazed by just how many animals Fluttershy owned. Bunnies and mice were scurrying around the floor, birds flying around or perched on the rails of the top floor. There was even a bear scratching its back on the wall.

"Wow, you have a lot of pets!" Jack exclaimed, staring slack-jawed at the indoor zoo.

"That isn't going to be a problem, is it?" Fluttershy asked nervously.

"Not at all. I love animals!" Jack exclaimed, smiling for the first time since he arrived in Equestria.

"That's wonderful! I know you and all my furry friends are going to be the best of friends!" Fluttershy exclaimed.

Jack chuckled a bit before noticing a small bunny giving him the stink eye. "What's your problem, little guy?" he asked, picking up the small animal.

As Jack gazed into the bunny's beady black eyes, he was turned away by a sudden pressure in his forehead. This was the same feeling he'd get when making eye contact with another human or, more recently, ponies. To Jack, it was as if the person making eye contact was reading into his soul, and he hated it. This was largely a problem exclusive to his childhood and had been mitigated since he started taking medication. Unfortunately, he'd left that medicine in his car, and the eye contact problem had come back worse than ever before.

Avoiding the dreaded eye contact, Jack spoke to the bunny the same way he would a small dog. "It's alright, little guy. I'm just going to be living here for a whi... OWWW YOU LITTLE FUCK!" he exclaimed as the bunny's teeth sank into his hand.

“What happened?” asked Fluttershy with concern.

“This fucking bunny bit me!” Jack exclaimed.

Fluttershy shot the bunny with the most intense stare Jack had ever seen. It was enough to intimidate the little shit, who quickly fucked off.

"I'm so sorry about Angel Bunny," Fluttershy apologized. "He can be a little territorial sometimes. Let me show you to your room." Fluttershy directed him up a flight of stairs to a hallway with two doors. “You can take the room on the right if that's ok with you."

"Thank you, Fluttershy," Jack said before going into the room. Once Jack entered the room, he realized that he didn’t have any clean clothes to change into. “I better ask Fluttershy where I can go to buy some new clothes." He rushed down to the living room and found her sorting through various pet food items, “Hey Fluttershy, do you know where I might be able to get some new clothes?"

Fluttershy jumped a little upon hearing Jack’s voice, "Oh, Jack, you startled me. If you need clothes, you should talk to Rarity. Um, also, Twilight wanted me to bring you down to the library if that's ok."

“Ok, what time does she want us there?” Jack asked.

“As soon as you’re ready," Fluttershy answered.

"Well, let's go then," Jack said, opening the door.

Fluttershy led Jack toward the Library. As he walked through Ponyville, Jack couldn't help but notice how beautiful the small town looked in the sunset. It somewhat reminded him of Downtown Summerville and Charleston's Rainbow Row. After a few minutes of walking, they arrived at a large tree that seemed to have been hollowed out and turned into a house.

“Is this it?” asked Jack.

"uh-huh," Fluttershy nodded.

When Jack opened the door, he found the room pitch black and seemingly empty. “Are you sure she’s home?”

“Sh-she s-said she would be here," Fluttershy answered.

"Ok," said Jack as he flipped the light switch.

“SURPRISE!!!!”

“JESUS FUCKING CHRIST!” Jack yelled, his heart pounding like a drum.

"Were you surprised, Jackey? Were you? Were you?" asked Pinkie.

“WHAT THE FUCK IS WRONG WITH YOU? ARE YOU TRYING TO GIVE ME A HEART ATTACK?” Jack yelled furiously.

Pinkie’s hair deflated at Jack's anger, “I-I was j-just trying to make you feel welcome in Ponyville."

Taking several deep breaths, Jack calmed himself down. "I'm sorry, Pinkie, I didn't mean to snap at you. Is this some kind of surprise party?"

Pinkie’s hair reinflated as she jumped up, “You bet it is! I throw one for every new arrival in Ponyville!"

“Thank you, Pinkie. Is Rarity here?” asked Jack.

“She’s right over there," Pinkie replied, pointing to the punch bowl.

“Thanks again, Pinkie,” said Jack as he walked toward Rarity.

Rarity was in the middle of a conversation with a small white unicorn who curiously lacked any kind of butt tattoo present in the older ponies.

"Excuse me, Rarity, can I talk with you?" asked Jack.

"Oh, Jack darling, I'm so glad to see you," Rarity greeted. "This is my little sister, Sweetie Belle. You'll be in the same class when you start school."

"Nice to meet you, Sweetie Belle. Mind if I talk to your sister for a bit?" Jack asked.

"N-nice to meet you too, Jack. Go right ahead," Sweetie Belle said quickly before running off.

"Well, she seems nice. I hope I didn't scare her," Jack said.

"You're fine, Jack. She's just shy," Rarity assured. "What do you need?"

“I don’t have any clothes to change into right now. Fluttershy said you could help me out with that," Jack explained.

"Of course. I'm a little busy at the moment, but when I have time, you should come by Carousel Boutique, and I'll take your measurements," Rarity agreed.

“I don’t really have any money right now. How much will this cost?” Jack asked.

"You don't need to worry about the price, darling. It's on me," Rarity said.

“That’s really generous, Rarity, but I insist you let me pay you something," Jack said.

"Being able to make such unique clothing will be payment enough," said Rarity with excitement. "You seem a lot more pleasant than before," she noted.

"Well it's not like being hostile to everyone is gonna get me home any faster," Jack sighed. “I just needed a little time to vent. Thank you, Rarity.”

His conversation with Rarity lasted a few more minutes before Jack said fair well and moved on. It wasn't long before he found his way to the snack bar and began to pig out. Just as he was about to eat his 7^th cupcake, Jack heard a voice from behind him.

"Excuse me."

He turned around and found Fluttershy and a pale-amber mare with a scroll cutie mark and glasses staring at him.

“Hey, Fluttershy. Who’s this?” asked Jack.

The mare in question held out a clipboard before speaking.

"I am Mayor Mare, the Mayor of Ponyville," she said.

“Mayor Mare? Really? These names are ridiculous," thought Jack. "Pleasure to meet you, Mrs. Mayor. What can I help you with?"

“Now that you will be moving into Ponyville as Fluttershy’s dependent, I need to have you both sign this document," she said.

"Ok," Jack said as he took the clipboard and signed his name under dependent.

Fluttershy then signed her name under guardian, and Jack left.

"Why doesn't he make eye contact?" Mayor Mare asked.

"Looking ponies in the eye makes him uncomfortable," Fluttershy answered.

Noticing Rainbow Dash and Applejack talking by the snack bar, Jack went over to talk to them, “Applejack, Rainbow Dash! How are you two doing?”

"I'm fine, no thanks to you!" Rainbow Dash snapped before storming off.

“What’s her problem?” Jack asked Applejack.

“Don’t worry nothin' about it! She's never been good with new ponies, and that fight you two got into didn't help none either. Give it a little time, and she'll warm up to ya," Applejack replied.

"If you say so," Jack said, not so sure.

“You’ll be startin' school on Monday, right?” asked Applejack.

"I'd assume so," replied Jack.

"Good, you'll probably be in the same class as mah little sister, Apple Bloom," said Applejack. "You might want tuh go talk tuh the teacher, Cheerilee. She's right over there," she said, pointing to a purple pony with flowers for a cutie mark.

"Thank you, Applejack, I'll go do that," Jack said before making his way toward Cheerilee.

“Excuse me, miss Cheerilee, is it?” Jack asked the mare.

"Yes?" she asked, turning around. "Oh, you must be Jack."

"That's me," Jack said.

"Nice to meet you, Jack. I'm Cheerilee, Ponyville’s resident teacher.” Cheerilee introduced herself.

“Resident teacher? You mean you’re the only teacher in all of Ponyville?” Jack asked.

"That's right," answered Cheerilee.

"Seriously?" asked Jack. "How does one person teach an entire towns worth of children?!"

“That’s a bit of an odd question. I alternate between 1^st to 5^th-year students on Mondays and Tuesdays and 6^th to 10^th-year students Wednesdays, Thursdays, and Fridays, just like every other teacher in Equestria," Cheerilee explained.

“That’s insane," thought Jack.

“How do you manage to teach 5 classes a day?” asked Jack.

"It can be hard sometimes. I teach for 10 hours a day except for weekends and holidays, then I spend another 3 hours doing other work," Cheerilee said.

“That would mean each student is only taught for two hours each day!” noted Jack.

“Very good! I see you know division well for your age. Maybe you can help some of the other students who are struggling when you join us next week," said Cheerilee.

“Did I just get complimented on my math skills? There's a first time for everything, but that really wasn't all that impressive," Jack thought to himself before coming to a realization. “Of course, she thinks I’m a child.”

“I’m going to go find Fluttershy so she can sign your forms. It was nice speaking to you!” Cheerilee said cheerfully.

"I guess I'll see you on Monday then," Jack said as she walked off. "And I thought teachers had it bad in my world.”

After a few hours had passed, Jack found himself talking to Twilight and Pinkie Pie.

“So, you were a history major?” asked Twilight.

"Yes, and I was minoring in religion," answered Jack.

“What’s religion?” asked Twilight.

"That's actually a tough question to answer since there isn't a set definition," said Jack.

"That's ok. It's getting late anyway. How about you come back here in a few days and give me a detailed explanation of religion along with the history of your world," Twilight said with a yawn. "Hey, Pinkie, I need some shut-eye. Could you tell everypony to go home now?" she yawned, going up the Stairs.

"Ok, Twilight. HEY EVERYPONY, IT'S TIME TO GO HOME!" Pinkie shouted into a megaphone she had pulled out of her mane.

With that, everyone at the party began to clear out. As Jack and Fluttershy were on their way back to the cottage, Jack couldn’t help but admire the night sky.

"Hey, Jack," said Fluttershy.

“Yes?” asked Jack

"I've signed you up for classes. I'm sure you'll make plenty of friends," Fluttershy said.

“I’m sure I will, Fluttershy," Jack said.

Secretly, Jack’s thoughts still dwelt with his family, but the ponies of Equestria were beginning to grow on him all the same.

Author's Note:

When I first started watching My Little Pony, I couldn't help noticing that Cheerilee seemed to be the only teacher in Ponyville. However, 16-year-old me didn't think too hard about it. Now that I've been in college for three years, I have a vague idea of how hard a job teaching is. When I started writing this chapter, I realized that Cheerilee must be working ridiculous hours to be teaching everyone and that the students probably don't spend all that much time in school. Although unplanned, the two hours, two days a week school thing works out pretty well for me as it gives me far more freedom to write non-school-related chapters on different days of the week.
Next time: Jack starts school in Equestria.

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