• 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 50: The Best Night Ever (Or is it?) (Last Edited 6/16/2022)

November 4, 2020

Manehatten Station

Shining Armor wasn’t sure what Hoity Toity’s goal was in asking him to take his vacation the week of the Gala, but he was grateful for the time he was now spending with Princess Cadence. He’d had his private train prepared to take both of them on a trip around Equestria. On Monday they’d departed Canterlot for Baltimare, on Tuesday they’d moved onto Fillydelphia, and now they’d arrived in Manehatten. Even still something was troubling him.

“Something wrong?” Cadence asked.

“I guess I’m just worried Flash Sentry might not have been the best replacement for gala security,” Shining Armor lied. “This is a strange favor. What could Hoity possibly hope to gain from me taking a vacation?

“You worry too much,” Cadence giggled. “It’s not often we get time alone together. Let’s enjoy it.”

Shining Armor smiled. “Can’t argue with that logic.”

Outside Carousel Boutique

Jack and Fluttershy had been preparing for the Gala all morning. They were to meet with the others at Carousel Boutique, but they happened across Applejack and Rainbow Dash on their way there.

“Where are the others?” they could hear Rarity say as they approached. “It's getting late.”

Twilight, Spike, and Pinkie Pie had already arrived, and Rarity of course lived in the boutique.

“Hold yer horses, girl,” Applejack called. “We're here.”

“Perfect,” said Twilight, slamming shut the book she’d been reading. “I'm ready!”

“For what?” asked Rainbow Dash.

“All right, Spike,” Twilight said as the dragon placed an apple down in front of her.

“An apple!” Pinkie exclaimed. “Are we having pie?”

“Shh!” Spike replied. “Watch!”

Twilight's horn glowed with a pale lavender aura as the apple transformed into a carriage.

“Cool!” Jack exclaimed as the others gave their own praise.

“Thanks, but that's just the start,” Twilight said. “Fluttershy, did you bring your friends?”

“Yes,” Fluttershy affirmed as a few mice popped out of her mane. “Will they be safe, Twilight?”

“You have my word,” Twilight answered. And with a flash of her horn, the mice became white stallions, albeit with whiskers. “Ta-da!”

“I wondered why you brought the mice,” Jack said as the others gave skeptical looks.

“Neat, huh?” Twilight asked. “And don't worry, they'll be mice again at midnight.”

Unfortunately, whiskers weren’t the only features the mice retained and the scent of rodents was irresistible to Rarity’s cat.

“Opalescence, no!” Fluttershy cried as the cat pounced with predatory intent.

The mice horses were too large for Opal to handle, and she was promptly thrown aside. But the attack was sufficient to startle the mice horses who fled.

“Wait!” Twilight called “Come back! Those horses were supposed to pull our carriage. How will we get to the Gala?”

“Whatever shall we do?” Rarity asked with a dramatic sarcasm. She then waltzed over to where some stallions were talking. “Uh... ahem. Excuse me. Uh, would you boys mind pulling our carriage to the Gala?” she asked, blinking seductively.

“Simps,” Jack muttered as the stallions harnessed themselves to the carriage with dopy grins.

Inside Carousel Boutique

Jack and Spike waited in the front room as the girls got ready. Jack had already put his suit on and was playing his 3DS in the corner. Spike on the other hand was impatient to discuss his plans with the girls.

“Come on, you guys,” Spike said knocking on the door. “Let me in!”

“Sure thing, Spike,” Rainbow Dash said before Rarity intervened.

Jack could hear them argue about letting Spike in since he was a boy. Rainbow Dash must’ve won because the door soon opened, and Spike went inside. Jack was about to go back to his game, but there was another interruption.

“You look nice.”

Putting the handheld aside, he saw Sweetie Belle was the one who spoke.

“Thanks, Sweets,” he chuckled. “But I think Rarity is owed most of the credit.”

“It’s more than the suit,” Sweetie Belle said. “I like what you’ve done with your mane too.”

Jack’s usual curls had been painfully straightened out with a comb at Fluttershy’s insistence. How long that would last, Jack couldn’t say, but for now, his unruly locks were tamed.

“Don’t get used to it,” Jack chuckled. “Do the Crusaders have any plans for tonight?”

“We…” Sweetie Belle hesitated as if she were thinking of how to answer. “We’re going to go stargazing.”

“Is something bothering you?” Jack asked.

“N-no!” Sweetie Belle yelled. “Nothing’s bothering me.”

That was the moment when the others finally left the dressing room.

“Time to go, Jack,” Twilight said.

“Alright,” Jack said, hopping up. “Have a nice night, Sweets. Can’t wait to go crusading with you and the girls when I get back!” he called as he followed the others outside.

“I hope you will,” Sweetie Belle said too quiet for anyone else to hear.

Hill near Ponyville Train Station

“It was sure nice of Twilight tuh lend us her telescope fer the night,” said Apple Bloom as she and Scootaloo worked to set the instrument up.

“And it was a great idea to set up on this hill,” Scootaloo said. “Look how clear the sky is! Nice call, Sweetie Belle!”

Sweetie Belle didn’t respond; she was too busy focusing on the station. “The only way she could get to Canterlot in time for the Gala at this point is by train.”

“Sweetie Belle?” Scootaloo asked.

I have to be right,” Sweetie Belle thought desperately scanning the station. Finally, she spotted something, “LOOK!” she shouted.

Apple Bloom and Scootaloo followed her gaze to see Sakura along with Rumple, Pip, Featherweight, Snips, and Snails slipping into the station.

“What are they doin’ gettin’ at the station this late?” Apple Bloom wondered.

“Let’s find out,” Sweetie Belle said, rushing down the hill.

“But we were gonna…” Apple Bloom was overruled before she could even object.

“Cutie Mark Crusaders instigators, yay!” Scootaloo declared following Sweetie Belle.

Ponyville Train Station

“Wait up, girls!” Apple Bloom called, finally catching up to the other Crusaders as they hid behind a column. “What….”

“Shhh!” Sweetie Belle said. “Look.”

Apple Bloom did as she was told and peered over to the ticket booth.

“Did you bring the bits?” Sakura asked.

“Yes, ma’am!” the foals exclaimed.

Snips, Snails, Rumble, and Pip all passed between ten and 20 bits each to Sakura.

“That’s not enough!” Sakura exclaimed.

“That’s my entire allowance for this month,” Rumble said.

“They hike up the prices during the Gala, baka!” Sakura shouted. “I need to get there!”

“I uh…” Featherweight started. “Here!” he said forking over 50 bits. “I sold my camera for…”

Sakura bought her ticket and was gone before Featherweight could even finish speaking.

“Why’s she acting so mean?” Apple Bloom asked.

“And why is she trying to get to Canterlot?” Scootaloo asked.

“Over here!” shouted Sweetie Belle. She’d opened up a massive suitcase on the Ponyville to Canterlot platform and climbed inside.

“What are you doin’ Sweetie Belle?” Apple Bloom asked as she rushed over with Scootaloo. “That’s somepony’s stuff!”

“I’ll explain everything later just get in!” Sweetie Belle pleaded.

“Ah’m not sure that’s a goo…” Apple Bloom froze at the look in Sweetie’s eyes. It was a mix of fiery determination and chilling fear.

“Trust me,” Sweetie Belle mouthed.

With an affirmative nod, Apple Bloom and Scootaloo followed their friend into the suitcase.

Canterlot Outskirts

“'Cause I planned out my insider's tour of Canterlot,” Spike explained as he and Jack sat in the driver’s seat together while the girls rode comfortably within the carriage. “I've gotta show Rarity the crown jewels, and Applejack the Princess's golden apple tree. And Pinkie, we gotta go to my favorite donut shop.”

“Sounds great, my guy,” Jack said, staring at the clear night sky.

“Then let's get moving!” Spike exclaimed, cracking the reigns with a “Hyah!”

“Excuse me?!” One of the stallions pulling them asked indignantly.

“Um... I...” Spike stutters.

“If you weren't friends with our neighbor Rarity...” the other stallion began shaking his hoof.

“You’d do what?” Jack asked darkly a brief shimmer of jade popping into his eyes.

“N-nothing,” the stallion stammered, focusing his attention back on the cart he was pulling.

You’ll have to let me out eventually,” Jade Jack hissed.

It will take a lot more than that.” Jack hissed back. “Even if something that small was enough, Spike deserved every bit of that.

On Route Ponyville to Canterlot

“What’s all this about, Sweetie Belle?” asked Apple Bloom as she and the other Crusaders climbed out of the suitcase, they’d hidden in.

“Yeah, you act like Sakura’s about to commit a crime or something,” Scootaloo agreed.

“She is,” Sweetie Belle said.

“What?!” Apple Bloom and Scootaloo exclaimed.

“Shh!” Sweetie Belle hushed. “Keep it down. I’ve been suspicious of her since the hydra attack. I overheard her talking about the ursa minor attack with Snips and Snails right before the three of them led the hydra to town.”

“Why didn’t you tell us?” Scootaloo asked.

“Would you have believed me?” Sweetie Belle countered.

Scootaloo had no retort.

“Even if that’s true how do ya know she’s gonna do somethin’ now?” Apple Bloom asked.

“I overheard her talking with some foreign pony,” Sweetie Belle said. “They want to kidnap Jack at the Gala.”

“What would they want Jack for?” Scootaloo asked.

“Same reason the EUP wants him, I guess,” Sweetie Belle answered.

Canterlot Outskirts

“I’m not singing,” Jack stated blankly as the song drew to a close. Truth be told he found the ponys’ tendency to spontaneously break out in song annoying.

Twilight dashed into the castle. “Princess Celestia!” she exclaimed rushing to where her mentor was standing at the top of the grand staircase.

“Twilight!” Celestia beamed. “It is so lovely to see my star student.”

“Oh, I'm so excited to be here!” Twilight exclaimed. “We have so much to catch up on.”

“Well, I want you right by my side the entire evening, so we'll have plenty of time together,” Celestia said.

“That's just what I was hoping you'd say,” Twilight said.

“Hey, Princess!” Jack greeted as he caught up. “What’s up?”

“Oh, not too much,” Celestia said. “I’ll be spending the Gala right here, greeting every single pony as they come in. Honestly, I can’t wait to announce the election results tonight.”

“It would be frustrating to stand in place for so long,” Jack chuckled.

“Speaking of frustration, how are things going with Jade Jack?” Celestia asked.

“Still trying to take every chance he can to take over my mind,” Jack admitted somberly. “Still keeping me from speaking to Emerald Jack.”

“You’ll find a way to beat him soon enough,” Celestia said.

“Heh, I just wish I had her level of confidence,” Jack chuckled nodding to where Rarity was pursuing Blue Blood with lustful intent.

“I just wish she had better taste,” Celestia responded. “You should go mingle. Though your EUP status is secret, you’ll find word of your heroics against the hydra has been difficult to suppress.”

“Oh, goody,” Jack sighed.

As Jack entered the crowd ponies did indeed acknowledge his feats during the hydra attack. Many even asked for autographs. In the end, it was Lyra Heartstrings who saved him from the crowd for better or worse.

“Something wrong,” Jack asked as Lyra led him through the hall. Jack was shit at reading body language, but the fact Lyra wasn’t bombarding him with questions was a hint enough something was up.

“I invited Bon Bon to the Gala as my plus one,” Lyra said with a bitter grimace. “She acted so eager, but she bailed last minute. Didn’t even give me an explanation.”

“You sure it wasn’t an emergency?” Jack asked.

“She would have told me if something came up,” Lyra answered glumly.

“Oh,” Jack said scanning the room for some distraction. “Look it's Fancy Pants and the others.”

“If it isn’t Mr. Jager,” Fancy Pants greeted upon seeing them. “Jolly good to see you chap! And Miss Heartstrings is here with you, I’d like both of you to meet my wife, Fleur de Lis.”

Fleur was a slender white unicorn who appropriately had a cutie mark depicting three fleur-de-lis symbols.

“A pleasure to meet you,” Fleur greeted with a graceful bow.

“It’s good to meet you too, ma’am,” Jack said awkwardly returning her bow.

“I do look forward to the election results tonight,” Fleur said. “Fancy has been working towards this for years. I was skeptical of his peasant’s rights stance when we first met but talking to these fine ponies,” she pointed to where Time Turner, Cherry Berry, and Apple Fritter were joking amongst themselves next to where Three Arrows sat with a scowl, “I think I finally understand my husband’s position.”

“That’s good to hear,” Jack said with a toothy grin.

“Oh my,” Fleur gasped. “Those teeth!”

“Now now, honey!” Fancy Pants responded. “Mr. Jager may have a less than herbivorous jawline, but that’s no reason to be frightened by him. He’s done nothing but protect Equestria since he got here!”

“And he’s done a piss pore job of it,” Three Arrows interjected. “I’ve been skeptical of your EUP membership since basic, Private, but after that disaster at San Franciscolt I’m surprised Celestia let you continue serving.”

“I know Longbow…” Jack started.

“I’m not talking about that!” Three Arrows interrupted. “Soldiers die all the time, it’s their job. You let that Damned character escape. Sloppiness at its finest!”

“You can’t be serious!” Time Turner interrupted. “An entire joint EUP taskforce with all four captains combined barely held together against that monster! Jack here was able to drive him off almost on his own.”

“Yeah, lay off him!” Cherry Berry agreed.

Jack was hit hard by Arrow's verbal abuse. Longbow’s death was only the most recent in a long line of tragedies he blamed himself for. The insinuation that the death of a comrade was insignificant compared to his inability to capture Damned was too much.

Fortunately, Apple Fritter picked up on this, “Ah heard mah cousin Applejack is here tonight. Ah’ll bet she’s set up a stand of sum sort knowin’ her. Why don’ we go see how she’s doin’?”

Canterlot Castle Courtyard

When they found Applejack, she was selling a pie to one of the Wonderbolts.

“Howdy cuz!” Apple Fritter greeted. “How’s sales tonight?”

“Oh hi, Apple Fritter,” Applejack said. “Long time no see. Ah jus’ set up a few minutes ago an’ Ah already made mah first sale!”

“Soarin right?” Jack asked the Wonderbolt who bought the pie.

“That’s right little dude,” Soarin said. “And you’re Jack, right? I heard about your heroics in San Franciscolt. None of us were even able to phase that guy, but you sent him packing.”

They talked for a while before Soarin left to meet up with the other Wonderbolts.

Elsewhere in the Courtyard

Blue Blood would be lying if he told himself he wasn’t worried. Which is exactly why he had told himself that over and over again. The first phase of the plan wouldn’t be hard for him all he had to do was signal the others while the crowd was distracted by the election results. The second phase however was another thing entirely.

“Is this amulet really enough to let me take on Auntie Celestia?” he asked himself, staring at the artifact with skepticism. He needed a distraction. Something to pass the time. His eyes locked on a young mare admiring a rose bush. She had a slender enough body, her fur and mane were well kept, and most importantly of all a flank with just the right shape to get his blood flowing. “I’ll bet if I play my cards right, I can persuade her into my chambers for a minute or two before it all goes down.” Most mares in Canterlot were wise to his game at this point, so it had been a while since he got any action. Suavely as he could he waltzed over to the mare and introduced himself. “Well, hello. I am Prince Blueblood.”

“I am... Rarity,” the mare introduced. “Oh my, what a lovely rose.”

Blue Blood plucked the rose with his mouth and held it out to Rarity as she grinned wildly. “You mean... this rose?” To Rarity’s shock, he shoved it into his vest. “Thank you. It goes with my eyes.”

Rarity let out a disappointed groan.

As the night went on Twilight attempted to hold a conversation with Celestia but found herself competing with the constant flow of arriving guests. Rainbow Dash tried to impress the Wonderbolts but was having similar luck to Twilight. Apart from her initial sale to Soarin Applejack didn’t make a single sale for the next half hour. Rarity was finding out more and more what an appalling stallion Blue Blood truly was. Fluttershy found her usual gift for animals had no power over the creatures in Celestia’s gardens. Finally, Pinkie Pie was finding that the party guests didn’t have the spirit she associated with party guests, but that didn’t stop her from trying to get them to get down.

“Young lady, this is not that kind of party!” A middle-aged mare said indignantly.

“Ohhhhhh... they don't want a party,” Pinkie Pie surmised. “These ponies want a paaartay!”

And from there all Hell broke loose.

First Rarity got Blue Blood a fritter from Applejack’s stand. Blue Blood freaked out upon realizing peasant food had violated his lips. Applejack was thus prompted to change her selection to a more refined pallet. Next, Fluttershy resorted to traps in order to gain the affection of the garden fauna. Then Pinkie Pie began assaulting partygoers to get them to get down, just as Applejack arrived with an elegant cake. Pinkie stage dived onto the cart sending the cake toward Blue Blood who in turn used Rarity to shield himself. This did not sit well with Rarity in the slightest and she began chewing Blue Blood out as he backed away to avoid getting any cake on him. Rarity was persistent however and shook a good bit of the mess on him as he fell back into a statue which came crashing down. Rainbow Dash caught the statue on her back but lost balance and fell back into a column which fell on another column creating a domino effect. Twilight arrived with Celestia and seeing the mess she jinxed everyone by stating it couldn’t get any worse. It did get worse as the door burst open with Fluttershy chasing a bunch of animals inside yelling about how they were going to love her. The animals began attacking the crowd as Jack looked on in horror. Celestia motioned for the six to make a break for it and Jack soon followed.

Pony Joe’s Doughnut Shop

Spike had been sulking ever since the party started. He’d wanted to show everypony his favorite spots in Canterlot, but they all abandoned him to do their own things.

“Hey, Pony Joe,” he grunted. “Another donut.”

“Don't you think you've had enough?” Pony Joe asked.

“Another donut!” Spike snapped. “Extra sprinkles!”

Before Pony Joe could fill the order, the bell rang, and in walked Jack and the Mane Six, battered and bruised.

“Twilight Sparkle, ha ha!” Pony Joe greeted. “Long time no see.”

“Hey, how was the Gala?” Spike asked. “How was your best night ever?”

As they gathered around the table, they explained everything to Spike.

“That sounds like the worst night ever!” Spike said.

“It was!” the Mane Six agreed in unison bursting into laughter.

“Eh, I’ve had worse,” Jack sighed.

“I just hope Princess Celestia isn't upset with us for ruining the Gala,” Twilight said somberly.

“That was the best Grand Galloping Gala ever!” Celestia exclaimed as she entered the building.

“Princess Celestia!” everyone exclaimed.

“Pardon me, Princess, but tonight was just awful,” Twilight said.

Celestia explained that the Gala was always awful, and she had invited them to liven it up. In the end, everyone agreed it was the best night ever.

“We should get back to the Gala now,” Celestia said. “It’s time to announce the election results.”

Canterlot Train Station

The CMCs watched from the window of the luggage car as Sakura got out on the platform.

“We need to get out of here,” Sweetie Belle whispered.

“We could get out through there,” Scootaloo said, pointing to a ventilation shaft.

The three of them scrambled up the shaft and onto the roof.

“She’s gettin’ away girls!” Apple Bloom exclaimed pointing to where Sakura was bolting through the ticket booths.

They shimmied down and began their pursuit but unbeknownst to them they were being watched.

“Mission Start,” Sweetie drops said flipping on her shades.

Canterlot Castle Ball Room

Celestia stood tall on the stage surrounded on either side by a line of Royal Guards. “Fillies and gentlecolts. I know many of you have been waiting with anticipation for these results. Today begins the peaceful transition of power from the elites to the citizens. A tradition I hope will last for many years to come.” Using her horn as a projector Celestia displayed a map of Equestria divided into 435 districts. “The House election results are as follows. Labor has won 57 seats, the Nationalists 159, and the Liberals 219.” The map changed to show Equestria’s 51 provinces. “Of the 102 Senate seats, Labor has 5, Nationalists 38, and liberals 59.” The image changed again. “I am humbled and somewhat disappointed to announce that with the most votes overall, I will be taking office as president and Princess Luna will act as Vice President.”

The room erupted into cheers and hoof stamps.

Canterlot Castle: North Tower

I’ll get back at that horse, Rarity,” Blue Blood thought bitterly as he stared at the landscape through the moonlight. “When this is over, I’ll have her working a street corner, but not before I’ve had my way with her. This humiliation shall not stand!

Charging his horn, he released a crimson flare into the night sky.

Western Canterlot Outpost

Flash Sentry overlooked the 40 ponies from various branches of the EUP who’d volunteered for the attack. He’d outfitted them with human firearms he’d been smuggling from the low country. He was just about to admire his 44. Magnum Colt Anaconda when he saw the flare.

“Show time,” he grinned.

Author's Note:

I've been real busy with my job as a park ranger. I think I've found my calling. Only a few chapters to go before this first story is over.
Next Time: The Battle of Canterlot begins

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