• Published 23rd Feb 2020
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Regression: Isekai of Equestria - JackofEquestria



Jack was once a rising senior at CCU, but now he and a large chunk of South Carolina have been sent to Equestria and to top it off he's been turned into a 7-year-old.

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Prologue Chapter 6 (Last Edited: 4/27/2022)

June 8, 2020

Fluttershy’s Cottage

Nothingness, pitch-black nothingness. Jack was vaguely aware he was asleep, but this knowledge meant little to him. For most people, the concept of floating around in an empty abyss would be terrifying, but not to him. He rather enjoyed the dark and found it to be peaceful. However, while he couldn't see anything, he could hear plenty.

“It’s all your fault!” shouted a girl.

“Why weren’t you there for me?” asked a boy.

"I hate you, Jack! I wish Shawn was my brother instead of you!" shouted another boy.

"I lost everything because of you!" another boy yelled.

“The world is better off without you!” they all said in unison.

The voices were endless, they drowned out everything, and they pierced deep into Jacks's subconscious. They went on for what seemed like hours before stopping abruptly.

"Thine mind is quite troubled, young human," said a voice from behind him.

He turned around to find a dark blue alicorn staring at him. She was smaller than Celestia, with a flowing mane that seemed like a clear night sky.

“Who are you?” Jack asked.

"We are Princess Luna, co-ruler of Equestria,” stated the alicorn.

“Why are you here?” asked Jack. “And what’s with the royal we?”

“We are the Princess of the Night! The Dream Realm is our domain!" Luna shouted.

"So, you go around visiting people's dreams then?" asked Jack.

"That is a rather simplified way of putting it, but that is correct, young one," stated Luna.

“Oh, come on, I may look like a child, but I’m 21 years old,” Jack said, crossing his arms indignantly.

“We have been alive for almost 2,000 years. To us, 21 is still quite young," said Luna.

"Fair enough," Jack shrugged.

“Doth thou have these nightmares often?” asked Luna as she walked closer to Jack.

"More often than I'd like," he admitted, staring into the empty void.

"Thou can look into our eyes, young human," Luna instructed. "Thou shall find that thine afflictions from the waking world do not affect thou here."

"How did you know about that?" Jack questioned. As his eyes locked with hers, sure enough, there was no discomfort.

"Our sister informed us," Luna answered, placing a wing over his shoulder. “We understand having regrets, young human. If thou ever wish to discuss them with us, we shall be happy to listen." The void began to fill with bright light. "We shall take our leave now. It is time thou woke up."

"Wait, don't leave me…" Jack started as his eyes shot open.

The Sun was shining through his window, the birds were singing, and a most wonderful scent emanated from downstairs. Jack knew he had been having a nightmare, but he couldn’t remember exactly what it was about. What he did know was that today would be his first day of school in Ponyville. The past two days had been relatively uneventful. He hadn't gone out much, and Fluttershy had been doting on him nonstop (almost like an overly affectionate mother.) He slowly slipped out of bed and got dressed. Walking down the stairs, he found Fluttershy making an omelet.

"Good morning, Fluttershy," Jack said with a yawn.

Fluttershy jumped at the unexpected greeting and timidly turned her head towards the source. "Oh, Jack, good morning. Did you sleep well?"

"I slept fine, Fluttershy," Jack answered, popping his neck.

"I'm so glad to hear that," Fluttershy said while putting Jack's plate on the table. "Eat up. You'll need a full belly to do your best!"

Jack scarfed his meal down with gusto before noticing Angel, giving him the stink eye again. He flipped the bunny off, and it stormed out of the kitchen. "I guess I'll be leaving then."

“Do you know the way?” Fluttershy asked as Jack was about to walk out the door.

Jack let out a short cough. “Well, now that you mention it. No, I don’t know the way."

"Let me take you," said Fluttershy.

"Ok," Jack sighed, disappointed at his inability to have time for himself.

Jack and Fluttershy made their way to the schoolhouse, and the yellow pegasus constantly expressed her worries along the way. “What if the other foals are mean to you? What if Cheerilee asks you a question you can’t answer? You packed your lunch, right?”

"I'll ignore them, I'll admit I don't know the answer, and yes, I packed my lunch," Jack said as they arrived at the school building.

"You're sure you'll be ok? I can go in with you if it would help," Fluttershy offered.

"I'll be fine, Fluttershy. See you after class," Jack said, heading into the building.

“Ok, I’ll be here in two hours to pick you up! Don’t forget to tell me all about your first day!” Fluttershy called as Jack closed the door behind him.

As Jack entered the schoolhouse, he noticed every pony inside turn their attention to him. No one said a word for what felt like hours, despite it only being a few seconds. Finally, a pink earth pony filly wearing a tiara broke the silence, “Who let that thing in?”

“And why is it wearing that ugly outfit?” asked a silver earth pony filly.

Jack wasn’t the least bit amused, "This thing has a name! It's Jack, by the way. I'm your new classmate, and what should I call you two?"

The pink pony turned to the silver pony and complained loudly, "They're letting animals into Equestrian schools now?"

“My daddy said it was only a matter of time before this happened. First zebras and donkeys, now apes. What’s next?” the silver one continued.

"This is why my daddy has been trying to get a private school built here. That way, we won't have to study with the peasants and animals," said the pink one. "I mean, this thing clearly doesn't know anything of Equestrian manners. It didn't even look me in the eye when it talked to me."

Ignoring the two brats, Jack sighed and took his seat next to a yellow earth pony filly with a red mane.

“Don’ mind Diamond Tiara and Silver Spoon. They’re mean tuh everypony." The filly smiled and introduced herself, "Ah'm Apple Bloom, by the way!"

"Nice to meet you, Apple Bloom. I'm Jack," he introduced.

Soon after Jack introduced himself, the school bell rang, and Cheerilee walked into the classroom, "Good morning, class! As most of you have probably noticed, we have a new student today. Jack, would you please stand up and introduce yourself."

“Hello, everyone. My name is Jack Delano Jager," Jack introduced, "Fluttershy adopted me after I was trans…” Realizing he was about to reveal his secret, he blurted out the first lie that popped into his head, “after my country was ravaged by a plague that wiped out everyone except for me!”

Scanning the room, Jack could see that all the foals (Except for Diamond Tiara and Silver Spoon) now had looks of sympathy on their faces.

Cheerilee was the first to speak, "I'm so sorry to hear that, Jack. Fluttershy never told me the circumstances of your adoption," she said soothingly before addressing the class. "I'd like each of you to introduce yourself and ask Jack a question. Please be mindful not to say anything that may make him uncomfortable.”

The first pony to ask a question was an orange pegasus filly. “My name is Scootaloo. What exactly are you?”

"I'm a human," answered Jack.

The next pony was Rarity's little sister, whose name Jack had already forgotten. “I’m Sweetie Belle, in case you’ve forgotten. Why do you wear all those clothes?”

"Humans don't have much hair apart from what's on our heads; we get cold very easily," Jack replied, rubbing his face for emphasis. "It's also considered rude to be naked in most human cultures."

A white earth pony with a frizzy red mane and blue glasses raised her hoof. "I'm Twist," she said with a nasally lisp. "You're a colt, right? It'th kind of hard to tell, ethpecially with your mane being all curly like that."

Normally ha would have been offended by such a question, but his 7-year-old body was admittedly quite a bit more androgynous than the foals in the classroom, and it didn't seem particularly common for colts to have hair quite as curly as his. "Yes, I'm a colt, well, a boy if you want to be more accurate. My hair just kinda naturally curls like this."

The next pony to raise their hoof was a fat grey unicorn colt, “I’m Snips. What exactly do Humans eat?”

“Vegetables, fruit, meat, pretty much anything, to be honest,” Jack replied

In a heartbeat, the fascinated looks on the foal's faces switched to that of an antelope that had spotted a lion in the grass.

“You don’t eat ponies, do you?” asked an amber unicorn colt. "Oh, I'm Snails, by the way."

"What? Ew, gross! I would never!" Jack answered, twisting his face in disgust.

There was a collective sigh of relief at that revelation.

A gray pegasus colt raised his hoof next. "I'm Rumble. What kind of games do humans play?"

"All kinds of games," Jack answered. "Hide and seek, tag, cops and robbers, video games..."

"What's a video game?" asked a skinny white pegasus colt. "I'm Featherweight."

Explaining the concept of video games took several minutes as the ponies didn't know what a TV was either. However, once he explained what a TV was, most of them figured it out.

"So it's like an arcade game that you keep in your house?" Rumble asked.

"That's right," Jack nodded.

Jack cringed when the next pony raised her hoof. "This is gonna suck.

"I'm Silver Spoon. How much money did your family make?" The filly asked before adding. "Not that it matters since you live in that hut with Fluttershy now."

"SILVER SPOON, THAT IS NOT APPROPRIATE!" shouted Cheerilee.

"It's fine, Miss Cheerilee. I'm more than happy to answer," Jack said calmly, but with a noticeable twitch in his eyes. “My parents made more than enough for us to live comfortably.”

As the next hoof rose, a sense of dread began to take over Jack's mind. "Not her.

“I’m Diamond Tiara. Have you been fixed and housetrained yet?" she asked with a shit-eating grin.

No one said a word for about thirty seconds. Jack glanced at Cheerilee. If looks could kill, Diamond Tiara would be dead. The teacher clearly wanted to say something but was holding herself back for some reason.

"Hey, ape!" Diamond Tiara sneered. "Look me in the eye and answer."

"Maybe if I just ignore her, she'll leave me alone. Jack hoped.

"What's wrong?" Diamond Tiara asked. "No answer? I guess you know your place at least."

The introductions and questions continued until only one pony remained. Apple Bloom slowly raised her hoof. “Ah’m Apple Bloom. Would you like to come over to Sweet Apple Acres and play sometime?”

Before Jack could answer, he was rudely interrupted by Diamond Tiara. “Oh my Gosh! Apple Bloom has a crush on the ape!” she shouted before adding. “I guess we shouldn’t be too surprised. I bet her whole family is into that kind of stuff!”

Apple Bloom's face flushed furiously as tears welled in her eyes. Everyone else just sat there in silence, but Something inside Jack snapped. Discomfort be damned, his eyes locked onto the rich brats, and he started to chew her out. "LISTEN HERE, YOU LITTLE BITCH! I DON'T KNOW WHY NOBODY ELSE IS SAYING ANYTHING, BUT YOU NEED TO SHUT THE FUCK UP! YOU THINK YOU’RE BETTER THAN EVERYONE ELSE BECAUSE YOU’RE RICH? FUCK YOU! NOW APOLOGISE BEFORE I COME OVER THERE AND MAKE YOU!”

Everypony was frozen in shock. Did this human honestly just stand up to Diamond Tiara. Jack, too was shocked by his actions. Meltdowns were a common occurrence in his childhood, but they had all but disappeared right alongside his eye contact problems when he started on his current prescription.

Oh, shit! Did I really just do that? I need to get my medication before I say something worse!” Jack frantically thought.

After a moment of silence, Cheerilee began to speak."Everypony except for Jack is dismissed."

As the foals cleared out, Diamond Tiara stuck her tongue out and sneered at the human before rushing out the door with the rest.

Cheerilee sighed. "What you said was unacceptable. I don't know if those words are just tossed around casually in your culture, but in pony culture, they are taboo."

"Well, I didn't see you telling Diamond Tiara to stop," Jack scowled.

"I understand wanting to put Diamond Tiara in her place," Cheerilee said. "I find myself having to hold back on scolding her almost every class. Unfortunately, she's the daughter of Filthy Rich, a member of the Royal Court. If I punish her, he could have the school shut down in retaliation."

Jack had never come across anything more disgusting in his life. A wealthy family shutting down a town's only public school because their daughter was a spoiled brat. He had always thought of rich people as douchebags, but this was flat-out evil.

At this point, Fluttershy came bursting in the door, asking why Jack wasn't waiting for her outside. Cheerilee explained what had happened to Fluttershy, who began to scold the human meekly. “Wh-why would you d-do that, Jack? Is something b-bothering you?"

Jack answered her calmly and clearly. "I have a condition known as Asperger's. It causes me to have terrible social skills, makes me prone to meltdowns like what happened in class, and also is the cause of my eye contact issues. Normally I take medication for it, but I left the meds in my car a few miles from where you found me."

Cheerilee interjected, “Would it be possible to get this medication?”

“Someone would have to go and get it from I-95... er my homeland," answered Jack.

After discussing the issue with Cheerilee for about 15 minutes, Jack and Fluttershy left for Golden Oak Library to ask Twilight if they could borrow her balloon.

When they explained the situation to Twilight, she agreed, and the two set off for the mysterious landmass.

June 9, 2020

Sky above Lake Marion

It had taken them over half a day of travel, but finally, Fluttershy and Jack had arrived at the bridge where he had abandoned his CR-V.

"So, where is this car thing?" asked Fluttershy.

“It should be down there," Jack said, pointing at the I-95 Bridge.

When Jack had initially ended up in Equestria, he was too distressed to notice just what a mess the bridge was in. Some cars were little more than twisted heaps of metal, having crashed at 60+ miles per hour. The guard rail was smashed clean through in some areas. Only a few cars were intact, which made it relatively easy to spot the untouched CR-V.

"There it is," said Jack before he bolted off in the direction of the green SUV.

Reaching his car, Jack opened the door and was almost knocked out cold by the stench. It was almost as if something had died. He looked toward the back seat and noticed his turtle tank. The water was putrid, no surprise, considering it hadn't been cleaned for days. He took the tank out of the car and dumped it on the asphalt. The turtles were still alive and quickly retreated into their shells once the water had drained.

“So, is this the car thing you were telling me about?” Fluttershy asked before noticing the turtles. “Oh, my goodness! Who put those poor turtles into such a small container?”

"I did," answered Jack.

“Why would you do such a terrible thing?!” Fluttershy asked, noticeably unhappy.

"I normally keep them in a bigger tank, but there's only so much room inside the car," Jack explained defensively.

"Why didn't you take them with you when we went to Canterlot?" Fluttershy asked, still slightly irritated.

"We teleported to the balloon so quickly that I didn't have time to tell you," Jack answered.

Satisfied with his explanation, Fluttershy returned to her usual cheerful self. "I understand, just try not to let this happen again," she smiled. "Did you get the medication?"

"I'll go get it now," Jack said as he opened the door and grabbed a green backpack that was sitting right next to the tank.

He opened up the backpack and found a lighter, two notebooks, his laptop, and three pill bottles.

"They're in here," Jack said as he zipped the backpack up and slung it around his shoulders.

Grabbing the turtles, they headed back to the balloon.

It had been an eventful few days in Equestria. If only Jack knew what fate had in store for him.

Author's Note:

With this chapter, the Prologue has come to an end. The next chapter covers the events of an episode and, as such, will have some copy and pasted dialogue from the transcripts. Every chapter based on an episode will have at least some copy-pasted dialogue, but some will have more than others.
Next time: Twilight receives two tickets to the Grand Galloping Gala and struggles to decide who to take with her.

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