• 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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Chapter 39 Over a Barrel (Last Edited: 1/17/2023)

October 1, 2020

Friendship Express on route to Appleloosa

The Crusaders had kept their promise. Not a soul had been told about Jack's secret. Spitfire had been frantic about the whole thing but calmed down after Jack expressed his trust in the fillies' ability to keep secrets. His therapy sessions in the Everfree had worked wonders, and his magic aura had returned to its usual emerald. Although Emerald Jack was still very much MIA and he dared not enter Chaos Mode.

Now, Jack was helping Applejack deliver a tree to her cousin in Appleloosa. Applejack had gone nutters over this tree. She had rented out the entire caboose to hold it. Rather disturbing in of itself, considering that's where the workers are meant to sleep. She'd also ordered a bed for it to lay in, started reading stories to it, and even named the damn thing. Bloomberg, as it was called, had already gotten on everyone else's nerves, and none more so than Rarity.

"Honestly, I don't understand what the big deal about this tree is," Rarity whined. "She has thousands of them back at Sweet Apple Acres."

"Well, the Apples do rely on their trees," Twilight said. "It's not that surprising they'd treat them with extra care, considering the financial situation they're in."

"First of all, caring for her trees is one thing, but that…" Jack pointed to a baby bottle filled with sugar water, "that's just creepy. Second, what financial situation?"

"You remember what I told you about Equestria's tax system, right?" Twilight asked.

"The upper three classes aren't taxed, right?" Jack asked. "The peasants have to pay for everything."

"Exactly," Twilight answered. "But the Apples have even more going against them than that."

"Like what?" Jack asked.

"When they revoked their business class status, most business-class families cut ties with them," Twilight explained. "Only the Rich family maintains a business relationship with the Apples, and they only purchase zap apple jam. All other Apple Clan products must be sold directly by the family or through contracts with small peasant-owned shops."

"I see," Jack muttered, flashing back to when Apple Bloom told him about her parents.

"Diamond Tiara's mean tuh everypony, but she treats me the worst."

"Why's that?"

"Ah think it's because of mah family. Most business-class ponies don't really like us."

"So, that's what she meant," Jack thought to himself. "Poor Bloom. I didn't realize how bad you had it. Well, at least things should be looking up soon. With the class system abolished, they should be able to recover quickly.""

As the train rattled towards Appleloosa through the parched desert, day turned slowly to night, and Jack settled down for bed. Unfortunately, most of his friends were still wide awake. He was about to ask them to pipe down when…

"Do you guys mind?" Spike growled from his bunk. "I was up early fire-roasting those snacks you're all eating, and I'm pooped!"

"Uh, speaking of, some of these popcorn kernels didn't get popped," Rainbow Dash said, nudging her popcorn.

"Okay, fine..." Spike sighed as Rainbow Dash smiled smugly.

Dash's smug demeanor was quickly abandoned as she ducked a fiery blast. As she looked up, she found her popcorn had been reduced to ash, save for a single kernel that popped in her face.

"Good night!" Spike shouted, retreating under his sheets.

"Uhh... maybe it's time we all got a little shut-eye," Twilight decided. "We've got a big day ahead of us tomorrow," she said, shutting off the lamp.

As the light faded, Jack stuck in his earbuds and drifted to sleep.

Or at least he tried. Unfortunately, he could still hear the girls talking.

"Oh, for Pete's sake!" Spike eventually yelled.

A few seconds later, the door slammed, and Jack assumed Spike must've left. Without removing his earbuds, he slipped out of his covers and followed.

As he slid the door to Bloomberg's coach open, he heard a clearly irate Rarity screaming, "Would you all be quiet... NOW?!"

The thought of brushing against branches and leaves in his sleep would typically have been enough to make Jack reconsider, but seeing Spike resting soundly on one side of the tree was enough for Jack to decide it was worth it. Squeezing his way to the other side of the trunk, he crawled under the covers and slowly fell asleep.

October 2, 2020

Friendship Express: Two miles north of Appleloosa

Jack's slumber was cut short by a heavy clunk. Before he could even open an eye, he found himself being smashed against the wall and crushed by Bloomberg. With another thud, Bloomberg rolled off of him, and with a pained groan, he pealed himself from the wall. Opening his eyes, he slowly shifted out of bed and limped to the other side of the caboose.

His face felt as if it had been hit with a fastball. Touching his nose, Jack found it was bleeding profusely. Whipping out his phone, he used the camera to take a look at himself. Not only was his nose bleeding, but it was also noticeably crooked. Broken for sure. His right eye was swelling like frightened pufferfish. Most likely, he'd be dealing with a black eye for the next week or so.

Miraculously Spike was still asleep, so Jack was free to focus on other things. Namely the sound of hoof steps on the roof. Grabbing his knife, he climbed out the nearest window and clambered to the roof, where he found Rainbow Dash chasing what appeared to be a small bison with a Native American headband.

"Hey, Dash, what's going on!" Jack shouted.

"I'm not sure!" Dash answered. "Help me catch her!"

Still not entirely sure what was happening, Jack stood up and held his arms out to block the bison's escape. Unfortunately, he didn't account for the crack between the caboose and the other rail cars and had to drop to the floor to avoid Rainbow Dash as the bison escaped between them.

Jack soon recovered from the shock, but Rainbow Dash had crashed into a crossing sign and wasn't so fortunate. As he stood up, he nearly lost his balance as the caboose lurched free of its coupling and fell behind the rest of the train.

Seeing the bison leaping onto the roof in front of him, Jack flipped open his knife. "Ah don't know who ya are, but you made a big mistake pissing me off!"

"This doesn't concern you," the bison said with a glare.

"It does now," Jack spat.

With a lunge, Jack swiped down on her with his knife, narrowly missing as she rolled to the side. Turning for another swipe, Jack felt the wind leaving his lungs as the bison rammed her head into his gut. Before he could even catch his breath, he felt another hit to his side and dropped the knife as he fell face-first to the floor.

Thinking she'd won the bison turned her back on Jack. Unbeknownst to her, the human still had some fight left in him. Hands glowing emerald, Jack pushed himself to his feet, spitting out one of his baby teeth as he rose. "Ah s'pose Ah should thank ya," Jack growled. "That tooth had been loose for weeks. Ah've tried everything to get it out."

"I'll admit you're tougher than you look," the bison said resentfully. "But you don't understand what's going on!"

"Enlighten me," Jack spat, aiming his palm at the bison. "'cause it sure looks like yer robbin' this train to me."

"We're just trying to save our tribal stampeding trail from the ponies!" the bison said.

"We?" Jack asked.

"Little Strongheart, you still up there?" called a gruff voice from below. "We found somepony inside the caboose!"

Looking down, Jack could see ten full-grown bison surrounding the caboose.

"Help!" Spike screamed. "Twilight! Rainbow Dash! Applejack! Anypony!"

"I'll calm him down," Jack sighed. "But you've got a lot of explaining to do!"

Climbing back into the caboose, Jack had no trouble getting Spike's attention. Unfortunately, one look at the humans beaten in face, and Spike was even more terrified than before.

"God damnit, Spike, it's me," Jack groaned.

"Jack?" Spike asked.

"Know any other humans?" Jack asked sarcastically.

"No," Spike answered, slowly calming down. "What happened to your face?"

"Smashed into a wall, then the floor," Jack answered, not even lying.

"What happened?" Spike asked.

"Not sure," Jack answered, cracking open the door. "But I think it might help to ask them."

"Ask who… Ahhh!" Spike shrieked as the door opened to reveal the small bison herd.

"We're coming out!" Jack called, dragging Spike by the tail as he stepped out.

"Wait, seriously, are you crazy?!" Spike cried, clawing the floorboards as Jack dragged him out.

"We'll be fine," Jack said as Little Strongheart hopped down from the roof. "Now, I think someone owes us an explanation."

"My father will explain everything when we get back to the camp," Strongheart said. "Help me grab the tree."

"Alright, but he better have a good explanation for this," Jack agreed, turning to help her retrieve Bloomberg.

"You can't be serious!" Spike exclaimed, grabbing Jack's arms. "This could be a trap!"

"I think if they wanted to trap us, they would have already done so," Jack responded, nodding toward the towering bison.

Buffalo Camp

The bison's camp was about two miles to the west of the tracks. By the time they arrived, both Jack and Spike were parched.

"I'm fuckin' dyin' over here!" Jack groaned as they walked into the circle of teepees.

A bison, slightly larger than the others and wearing a Native American headdress, approached from the largest tent. "Bring our guests something to drink," he ordered before giving Jack and Spike a good look. "Bring salt for the ape and turquoise for the dragon as well."

"Salt?" Jack asked. "What fo… OWWW, THE FUCK'S WRONG WITH YOU PEOPLE?!" Jack asked as Little Strongheart poured a bowl of salt over his still-bloody nose.

"You'll probably need a pony doctor to put your nose back in place, but this will keep it from getting infected," Strongheart explained.

"You could have warned me first!" Jack shouted.

"I'm so sorry!" Strongheart franticly apologized.

"You should be," Jack sighed. "I believe we're still owed an explanation. Isn't that right, Spike?"

"Mhm," Spike agreed, crunching into one of the gems he'd been given.

"You'll get your explanation soon," the giant bison said. "But first, introductions are in order. My name is Chief Thunderhooves of the buffalo tribe. Who and what are you?”

"My name is Jack Delano Jager," Jack introduced. "I'm a human, and my dragon friend over there is named Spike."

"Human?" Thunderhooves mused. "Legends speak of your kind's warrior spirit and great wisdom. We took you and the dragon by mistake, but perhaps you will be able to help us."

"Help you?" Jack asked. "With what?"

"We have a long and winding stampeding trail that we have run upon for many generations," Thuderhooves explained with a snort. "My father stampeded upon these grounds, and his father before him, and his father before him, and his father before him, and his father before him, and…"

"I think they get the idea, Chief," Strongheart interjected.

"Hmph," Thunderhooves grunted. "It is a sacred tradition to run the path every year. But this year, these... settler ponies, these..." with a loud snort, he spat," Appleloosans!"

"They planted apple trees all over it without asking our permission," Strongheart explained.

"So that's what this is about," Jack thought to himself. "That's why they were after Bloomberg."

It was undoubtedly a more PG version of events, but there was no mistaking things. Equus had many parallels with Earth. This was no doubt the equestrian version of the European colonization of the Americas.

"The ponies refused to move their trees, so we are stuck here, and it is not fair!" Strongheart lamented.

"You're right," Jack agreed. "It isn't fair. Nothing about this is fair!"

"Then you'll help us?" Thunderhooves asked.

"Yes," Jack nodded. "But first, there's someone we need to rescue."

Two Miles North of Appleloosa

Jack and Spike road towards the site of the hijacking on the backs of bison warriors.

"You sure she'll be out here?" asked one of the warriors.

"If I know Dash, she won't have given up so easily," Jack said. "Her rainbow mane should stick out like a…" Jack stopped spotting what appeared to be a tuft of cotton candy sticking out from a rock. "Pinkie Pie?" Pointing to the rock, he shouted, "over there!"

As the bison surrounded the rocks, Jack could hear Rainbow Dash and Pinkie arguing.

"And the more of us there are out here, the more chances of us getting..." Rainbow Dash finally noticed the buffalo warriors, "caught. Run, Pinkie, I'll hold 'em off. Save yourself!"

As the bison charged, Jack shouted, "STOP!" The bison parted to allow him and Spike through. "Attacking them is no way to ask for help," he sighed.

"Don't worry, they're cool," Spike said.

"If you say so," one of the bison replied. "See you guys back at the camp!" he called as the herd dispersed, leaving Rainbow Dash and Pinkie Pie staring in confusion.

Later that night

Buffalo Camp

"Seems they took us by mistake," Spike explained as they sat around a campfire. "And they feel awful about it too, poor guys. Fortunately, they totally respect dragons, so they treat me like an honored guest."

"Don't seem to have a problem with humans either," Jack added as the bison brought out two bowls of gruel for Dash and Pinkie.

Sniffing her bowl, Dash reared back in disgust.

"Still don't like ponies much, though..." Spike said. "But you're with us, so it's cool."

"Huh. Well, I still don't trust them," rainbow Dash as she got up to scout for an escape route. "I say we turn tail and bail while we still…"

Pinkie Pie lifted her face from her bowl, face still covered in gruel. "Before we finish eating?" she asked. "Are you loco in the coco?!"

Before Rainbow Dash could answer, Little Strongheart approached with a bowl of turquoise and leafy greens.

"Can I please have more of that mushy stuff, whatever it was?" Pinkie asked as Strongheart set the bowls down.

"Certainly," Strongheart smiled. "I'm not sure what humans eat, so I brought these. And, Mr. Spike, you like gemstones, yes?"

"That'll be fine," Jack said.

"Turquoise. Mmm!" Spike said, crunching down a handful. "Heh hah! This here is Little Strongheart, and these are our friends Pinkie Pie and Rainbow Dash."

Rainbow Dash turned with a skeptical look before glaring. "You!"

"You!" Little Strongheart gasped.

"That's it!" Rainbow Dash huffed, grabbing Pinkie by the tail. "We are outta here!"

"Wait!" Little Strongheart shouted, getting in front of Dash. "Please accept my apologies for what happened on the train. We didn't mean for anyone to be hurt."

"Yeah, right," Rainbow Dash scoffed, turning the other way.

"Hear her out, Dash," Jack said. “Didn’t you learn anything from when we met?”

"But she… look what they did to your face!" Dash protested.

Jack gave her a stern look.

"Fine," Rainbow Dash sighed.

"We only wanted the tree," Strongheart explained. "The settler ponies have overtaken the land and have planted an orchard all over it! Because of their thoughtlessness, we can no longer run over our traditional stampeding grounds."

"Huh?" Rainbow Dash and Pinkie Pie asked in confusion.

"I think it's time they met Chief Thunderhooves," Spike offered.

When the chief arrived, he told Dash and Pinkie the same story he'd told Jack and Spike. All the while, Rainbow Dash pouted with her back turned to him.

"See, Rainbow Dash?" Spike asked. "They had a good reason to…"

Dash shot up, eliciting a gasp from the bison. "Huh... Ah!" Stomping her hoof, she said, "I'll say they had a good reason! C'mon. We have some apple-pickin' Appleloosans to talk to!"

October 3, 2020

Outskirts of Appleloosa

Although Rainbow Dash had been eager to begin negotiations, Jack quickly vetoed the idea in favor of a good night's sleep. The following morning, they set out with Little Strongheart to Appleloosa, choosing to leave the other bison behind to avoid hostility.

As Jack, Spike, Rainbow Dash, and Pinkie Pie approached the town's outskirts, they made out the telltale sign of dust being kicked up by speeding ponies galloping across the desert. Sure enough, they were met with the rest of the Mane Six along with another pony they were unfamiliar with.

"Hi, guys!" Pinkie greeted cheerfully.

"Jack!" Fluttershy shouted, tackling her adoptive son to the ground in her embrace. "We're so glad you're safe," she said as the others greeted each other.

"Jeez, mother!" Jack exclaimed. "I'm fine!"

"How did you escape from the buffalo?" Twilight asked.

"We didn't!" Pinkie answered as Little Strongheart leaped out from the rock she'd been hiding behind.

The other ponies gasped as Strongheart shifted awkwardly.

"We promised the buffalo a chance to talk," Rainbow Dash explained.

"Oh, yeah?" Applejack asked skeptically. "'Bout what?"

"We brought our new pal Little Strongheart here to explain to the Appleloosans why they should move the apple trees off buffalo land," Rainbow Dash explained, pushing Strongheart over to the unfamiliar pony.

"That information would be quite help…" the pony began.

"That's weird," Applejack said, forcefully shoving the pony. "'Cause mah cousin Braeburn here wants tuh explain tuh the buffalo why they should let the apple trees stay."

"That would be a useful thing to…" Braeburn started.

"The land is theirs!" Rainbow Dash shouted. "You planted the trees not knowing that. Honest mistake. Now, you just gotta move 'em, that's all."

"Well... heh..." Braeburn stuttered.

"They busted their rumps here!" Applejack interrupted. "An' now they're supposed tuh bust their rumps again, just 'cause some buffalo won't stampede someplace else?"

And like clockwork, the negotiations turned into nothing more than a heated debate between Rainbow Dash and Applejack.

"They argue like an old married couple," Jack thought to himself.

"Look!" Twilight interrupted. "Both the settlers and the buffalo have good reasons to use this land. There must be something we can do."

"Hey!" Pinkie exclaimed, jumping in the air. "I've got an idea!"

"Nothing good can come of this!" Jack thought with a gulp.

Appleloosa Outdoor Theatre

Pinkie Pie had instructed Little Strongheart to gather the bison and Applejack to gather the Appleloosans, and they all met up around the town's outdoor theatre. The crowd of ponies and bison murmured confusedly as Spike played a few notes on the piano.

As the curtains parted to reveal Pinkie emerging from a clamshell in a ridiculous outfit, Jack knew he'd have to act fast. "God damnit, Pinkie! Abort, abort!" he mentally screamed as he used his magic to shatter the floorboards beneath her.

Once Pinkie Pie was out of the way, Jack stepped onto the stage. "I'm terribly sorry about that," he said once he reached the mike. "I'd like to tell you all a true story about my people. I think it might bring things into perspective."

Knowing he'd have to modify the events to maintain his cover Jack began his story. "Before the virus wiped most of us out, humans occupied an archipelago of 7 islands, America, Europe, Asia, Africa, Australia, Antarctica, and the Lowcountry. The first humans came from Africa, but over the years, we spread out to the other islands, adapting to them in various ways resulting in minute differences between different societies. The most noticeable being skin color. Those who inhabited Europe had white skin like mine. The majority of human societies had some level of contact with each other. In fact, there was heavy trade between Europeans, Asians, and Africans. However, for much of history, we had no idea America and the Low Country even existed."

Several ponies and bison raised their hooves.

"Yes?" Jack asked.

"Where are you going with this?" Rarity asked.

"You'll see," Jack answered. "Over a thousand years ago, a group of Europeans known as the Vikings (my ancestors) discovered the Lowcountry, but they kept that discovery to themselves for hundreds of years before another group of Europeans led by Cristopher Columbus discovered the island. Columbus captured some of the red-skinned inhabitants of the Lowcountry and brought them back to Europe. Soon Europeans came in waves bringing with them diseases that wiped out large swaths of the native populations of both the Lowcountry and America. Many of the survivors were enslaved, although this didn't last long as they knew the land so well, they easily escaped. Nevertheless, land cleared out by the diseases was turned into European-run farmland, and violent conflicts between European settlers and the remaining Natives resulted in them being pushed into smaller and smaller territory. The Europeans would sign treaties with the Natives only to break them years and sometimes only months later. They'd even go so far as to send disease-ridden blankets to further wipe the natives out. Over time the Europeans and the Natives made peace allowing the small tracts of land the natives occupied to be turned into reservations. Still, injustices such as Native children being stolen from their families and raised by Europeans continued until about half a century ago. That being said, the Europeans…"

"Enough," Chief Thunderhooves bellowed. "I think I understand what you are saying."

"You do?" Jack asked.

"If we do not put our hooves down now, these Appleloosans will walk right over us. The time for action..." Thunderhooves snorted, "... is upon us! Our stampede will start at high noon tomorrow." Turning to the town's sheriff, he said, "And if the orchard is still there, we'll flatten it... and the whole town!"

The Mane Six and townsponies gasped.

"That's not what I was…" Jack said. "If you'd just let me finish…"

Unfortunately, no one was interested in what else Jack had to say.

"An' we Appleloosans say you'd better bring yer best, 'cause we'll be ready and waitin'," the sheriff retorted.

"But, Sheriff..." Braeburn protested.

"That's not what I was trying to say at all," Jack muttered to himself.

October 4, 2020

Appleloosan Medical Clinic

Jack's plan had failed miserably. Had he only finished his point, then maybe things could have gone differently, but now the townsponies were preparing their defenses.

He wanted to help, but what could he do? He'd already made things ten times worse. Now the best thing he could do was get his broken nose tended to.

"You'll need to wear this splint for at least a week," The doctor told him.

"Yes, sir," Jack nodded as it was applied to his face.

No sooner had the doctor finished did a bell ring across the town.

"Ah reckon, the fight'll be startin' now," the doctor said.

This is my fault,” Jack thought glumly.

"Yes, it is, isn't it," Jade Jack jeered from within his head.

"Shut up!" Jack hissed mentally. " I'll find a way to fix this! Even if only to spite you!

Jack rushed out of the clinic toward the battlefield as fast as he could. There wasn't much damage to the town beyond the clock tower having collapsed. Other than that, there was just a ton of apple pies smashed on the ground, having been used as ammo by the Appleloosans.

"If I can find Cheif Thuderhooves and the Sheriff I should be able to clear things up," he thought.

"You're with them now aren't you!?"

"Huh?" Jack turned to see a thousand-pound bison charging him.

"Sorry about this!" Jack cried launching a volley of emerald blasts.

"You will be!" the Bison snorted, launching Jack into the sky with a full forced headbutt.

Jack wasn't sure how far he'd gone but he could see the fighting was intensifying. Fortunately his eyes locked onto Chief Thunderhooves charging the sheriff, he used his magic to pluck the thorns from nearby cacti. "I'm only gonna get one shot at this," he thought.

"Now!" he shouted to himself, launching two volleys of cactus thorns at both the chief and sheriff.

The sheriff screamed in pain, and Thunderhooves veered off course, crashing into a wall. Having witnessed this, the ponies and bison ceased combat to check on their commanders.

"I assume I have your attention?" Jack asked as a pie fell from a window onto Chief Thunderhooves. He'd gotten no response, but he knew they were listening. "Good, I realize that the half of my story you heard yesterday gave you the wrong idea, so I think it's time for the other half. While the Natives were certainly oppressed by the Europeans, most of the settlers were themselves the victims of oppression. Europe was a feudal society, and many peasants saw the Lowcountry as an escape from such oppression. Some even agreed to seven years of voluntary servitude for a chance to go. Much like European peasants, the Apples are oppressed by Equestria's business class. Surely you can find some sense of camaraderie in your oppression. Perhaps you could find a compromise?"

Chief Thunderhooves looked to be considering Jack's words, after a piece of apple pie that had been plastered on his face from the battle dripped into his mouth he spoke, "I think that can be arranged."

And so, it was agreed that a path would be cut through the orchard for the bison to stampede, but the rest of the orchard would remain intact. In return, the Appleloosans would share a portion of their pies with the bison. Bloomberg was returned to the Apples and planted in the orchard, much to Applejack's relief.

Author's Note:

I think that went well for the most part. A bit rushed at the end, thanks to my self-imposed deadline, but that can be fixed later with editing.
Next Time: As elections draw near, three political parties are formed, and they are willing to do whatever it takes to draw in new members. Even play dirty.

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