• Published 23rd Feb 2020
  • 5,012 Views, 382 Comments

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 11: Look Before You Sleep (Last Edited: 6/30/2022)

July 3, 2020

Fluttershy’s Cottage

It was 9:00 AM, and Jack was just waking up from the best sleep he had had since coming to Equestria. No dreams, no Angel waking him up early, and with his problems with Fluttershy having been resolved two days prior, no staying up fuming about how she had ruined his day.

He grabbed his pill bottles from the dresser and found he had only five days' worth of pills left. “This could end up being a problem,” he thought with a groan.

Popping the pills into his mouth and washing them down with a glass of water, he thought to himself, “I better talk to Twilight about this.

Putting on his clothes, he walked down the stairs. Upon entering the living room, he found Fluttershy on the couch, face buried in a book.

"Good morning, Jack," she said, placing her book on the ottoman.

"Morning, Flutters," Jack greeted.

“Flutters?”

“Yeah, it’s a nickname,” Jack explained.

“A nickname?”

"Yeah, like how Apple Bloom is Bloom, Scootaloo is Scoots, Rainbow Dash is Dash, and Pinkie Pie is Hyperactive Abomination," explained Jack.

"I know what a nickname is, Jack. I just didn't expect you to give me one," Fluttershy said. "Also, your nickname for Pinkie Pie isn’t very nice.”

It's not entirely inaccurate though," thought Jack. "That one was just a joke, and besides, you ponies have such long names. It's so much easier to use nicknames instead. That's why you call me Jack instead of Jackson Delano Jager Jr.”

“You were named after your father?” asked Fluttershy.

"Yep, that's why I go by Jack instead of Jackson. It keeps people from getting confused," Jack answered.

Noticing a suitcase packed by the door, Jack asked, “so, where are you going?”

"Oh, I was just about to tell you," said Fluttershy. "I'm going to be visiting parents in Cloudsdale for a couple of days. My brother's moving back in with them... again," she scowled. "I'd take you with me, but I'm pretty sure you can’t walk on clouds.”

"That would be a problem," agreed Jack. "I guess I can stay with Twilight while you're gone."

"You can stay here by yourself if you want. I won't try to stop you, you know," Fluttershy offered grabbing her suitcase.

“I know, but if ponies in town notice that you’ve suddenly gone from overprotective mother to super cool mother who lets her 7-year-old son stay home alone, they might get suspicious," Jack explained.

"That makes sense," said Fluttershy. "Um, I guess I'll see you when I get back."

“See you when you get back!” Jack called as she walked out the door.

Walking back to the couch, Jack noticed Angel gnawing on a carrot. "You think she'll notice if I take a few fish from the fridge before I go to the library?"

The bunny just stared at him with a look that said, you know damn well what I think.

"Oh, don't give me that look," Jack said as he opened the fridge. "Be glad I'm not eating you," he said, only half-joking.

After eating the fish, Jack said farewell to Angel and headed off to the library.

Golden Oak Library

"Spike, could you bring me the phone?" asked Twilight. "I think I figured out how to fix the battery problem."

"Ok, Twilight, I'll be right there," Spike said, grabbing the iPhone 6 from the table.

As Spike handed the phone to Twilight, there was a knock on the door.

“Spike, could you get that?” asked Twilight.

“Sure thing, Twilight!”

He opened the door to find Jack on the other side with a suitcase and a sleeping bag.

"Hey, I know this is short notice and all, but Fluttershy went to Cloudsdale, and I was wondering if I could stay here until she gets back," Jack explained.

"You'll have to ask Twilight," Spike said. "Come on in." He brought Jack to Twilight’s study. “Hey, Twilight, Jack wants to know if he ca…” he started. “Burrrp!”

A scroll appeared in a flash of green fire from Spike’s belch.

“Is that a letter from Princess Celestia?” Twilight asked as she exited her study.

"Yes," Spike answered. “Do you want me to read it now or wait until later?”

“It's probably important, so I think it'd be best to go ahead and read it now," Twilight responded.

Dear Spike, your presence is requested at the Royal Court tomorrow at 6:00 AM. You are instructed to come alone. Enclosed is a two-way ticket for your journey to Canterlot and your return home. Please leave at your earliest convenience.” Spike read. "Why would the Royal Court summon me?"

"I don't know, but it must be important," Twilight answered.

“I better get going then," said Spike as he rushed to his room to pack.

“So, what brings you here, Jack?” asked Twilight.

"Fluttershy went out of town to visit her parents, and I was wondering if I could stay here until she gets back," Jack explained, pointing to his suitcase and sleeping bag.

“Can’t you just stay home alone?” asked Twilight.

"I could, but then the rest of the town might get suspicious," Jack answered.

"That makes sense," Twilight said, considering Jack's request. "You can stay here until Fluttershy gets back. In the meantime, I have a few things to show you. Oh, and later we can try practicing your magic!" Twilight said in excitement.

Spike walked down the stairs with a packed bag. “Bye, Twilight! Bye, Jack! See you when I get back!”

“Good luck, Spike!” Twilight called as the baby dragon walked out the door. As the door closed behind Spike, Twilight turned her attention back to Jack. “Come with me.”

Jack was led into Twilight's study, where he found the contents of his car carefully laid out on several tables and sorted neatly into groups. One table held his phone, TV, X-Box One, X-Box 360, Nintendo Switch, Wii U, 3DS, Game Boy Advanced, controllers, games, DVDs, CDs, and other electronics. There were other objects such as his recorder, Zippo lighter, spare pocketknives, lighter fluid, used flare gun, wallet, passport, confirmation cross, and car keys, while several more tables held various other items.

“What’s all my stuff doing out here?” Jack asked.

"I finished studying them and decided to give them back to you," Twilight responded, levitating the phone over to her. "I've even figured out how to fix the problem with your phone's battery… I think," she added as she levitated a glowing phone battery and gently placed it into the back of the phone. "By enchanting the battery, I've converted your phone from running on electricity to magic absorbed from the air. I still need to work on your other electronics, though.”

After Twilight levitated the phone over to him, Jack tapped in the passcode and looked through his photos. “It works great, Twilight.”

"I'm so glad to hear that," Twilight said gleefully before taking on a more professional tone. "On a more serious note, could you show me that gun you used the other day?”

“Um, sure," Jack said as he pulled the Glock out of his pocket.

"Mind if I take a look at it?"

Jack wasn't entirely comfortable with handing Twilight a loaded gun. As far as he could tell, the Glock didn't have any kind of safety switch, and the last thing he needed was for Twilight to shoot herself by accident. "Just let me unload it first," he reluctantly agreed.

Jack carefully unloaded the gun and handed it to Twilight, who spent the next few minutes examining it.

"I've read about guns in a few of the books I found in the Lowcountry," Twilight explained as she handed the gun back to Jack. "You wouldn't mind giving me a demonstration, would you?"

"I wouldn't mind at all, but we'll need to go somewhere else to do it," Jack said.

Edge of the Everfree Forest

Jack brought Twilight to the outskirts of town, an isolated area near the edge of the forest. Their only company being the crickets and tree frogs and their respective chirps and croaks.

“Why do we need to come all the way out here?” asked Twilight curiously.

“So I don't accidentally shoot someone," Jack explained as he loaded the Glock.

“That makes sense," noted Twilight.

Jack cocked the pistol and then turned to Twilight. "Stand back a bit."

Twilight stepped back a few yards and took out a notepad. “Carry on!”

“I’m going to aim for that tree over there!” shouted Jack as he pointed to a large pine about 6 yards away. "You might want to cover your ears."

Carefully aiming at the trunk, Jack pulled the trigger. With a thunderous bang, the bullet was unleashed upon the tree.

"Sweet Celestia, that was so loud!" Twilight exclaimed, ears ringing as she scribbled on her notepad. “Did you hit it?”

“Of course I hit it!" Jack exclaimed with a cocky grin. "Want to check it out?”

Twilight was already halfway to the tree when he asked.

"I'll take that as a yes," Jack chuckled as he ran after his fellow academic.

When she reached the tree, Twilight began meticulously jotting down her findings in her notebook. “The hole is quite small compared to an arrow. Can I see one of the bullets?”

"Sure," Jack answered as he unloaded the Glock and handed Twilight a bullet.

As she examined the 9x19 mm round, the purple unicorn continued scribbling in her notebook, "Did you really think this would do any damage to a dragon?"

“Huh?” Jack asked.

“The bullet, did you think it would do anything against the dragon?” Twilight asked again.

"Well, to be honest, I wasn't really thinking," Jack said. "I panicked and grabbed the only weapon I had on me."

“I see…” Twilight said. “Speaking of panic, I’m pretty sure I’ve figured out how your magic works.”

“Really? How?” Jack asked, eyes wide in excitement.

“Think about it. The first time you felt your magic was during your confrontation with Gilda. What happened immediately before you felt the sensation?” Twilight asked.

“Well…” Jack started thinking back. “She knocked my knife out of my hand and roared really loudly.”

"And then, during the Timberwolf incident, your magic came out when the Timberwolf tried to bite you, correct?" Twilight questioned.

"That's right," Jack answered.

"The magic also came out when you and Scootaloo were cornered by the Ursa and when the dragon shot its breath attack at you," Twilight continued. "Each incident has one thing in common.”

“And what would that be?” Jack asked.

"Your life was in danger," Twilight answered. "Do you remember what the dragon said while you were fighting him? The magic controls you, not the other way around. I believe it's a defense mechanism triggered when you are in life-threatening situations."

“That makes a ton of sense, but how would we test that theory?” Jack asked.

"We don't," Twilight answered.

“What?!” Jack asked. "I must have misheard you. It sounded like you said we shouldn't test it."

"The only way to test that theory properly would be to put you in a life-threatening situation. I'm not going to do that to a friend," Twilight explained.

Jack had to admit Twilight made a good point. That being said, he wouldn't be satisfied simply giving up. “Still, couldn’t you try to teach me how to use my magic without putting me in danger?”

"Absolutely! I was just about to recommend that," Twilight said.

After hours of trial and error, they were no closer to figuring things out than when they started. Out of ideas for the moment, they decided to return to the library.

Ponyville Park

By the time they reached the park, Ponyville had been engulfed in a thunderstorm. As they ran through the downpour, Twilight noticed Applejack and Rarity sheltering under a bench, hooves plastered in mud.

“Applejack! Rarity!” she shouted.

The two ponies looked up from their muddy cramped shelter.

"Twilight? Jack?" asked Applejack.

“What are you two doing out in this dreadful weather?” asked Rarity.

"I could ask you the same thing," Jack replied.

“We were out here takin' down loose branches tuh prepare for the storm, but since somepony decided tuh prettify everythin', we got caught in the storm before we could finish," Applejack said giving Rarity a sour look.

Rarity huffed in indignation.

"Well, you can't just stay out here," Twilight said. "Come back to the library with us, hurry.”

The library making for a much better shelter than their bench, Rarity and Applejack followed Jack and Twilight.

Golden Oak Library

Twilight, Jack, and Rarity ran inside as soon as they reached the library, but Applejack was a little more hesitant, “Whoa nelly. Is inside a tree really the best place to be in a lightnin' storm?”

"You know, Applejack actually has a good point," said Jack.

“It’s fine. The library has a magical lightning rod installed," Twilight explained. "Come on in!”

“We are most grateful for your invitation," Rarity said, bowing her head.

“Thank ya kindly fer yer hospitality," Applejack said, tracking mud into the doorway.

Rarity put up a hoof to block Applejack from going any further. "Uh, do be a polite house guest and go wash up, please, won't you?”

“If Ah gotta spend one more second with that fussbudget Rarity today, Ah can't be held responsible fer what Ah'm gonna do," Applejack grumbled as she walked outside to hose off.

She doesn’t seem too happy," thought Jack as he shivered. "Hey, Twilight, where do you keep the towels?"

"Upstairs in my bedroom closet," Twilight replied. "Bottom shelf."

"Thanks," Jack said as he walked up the stairs.

Twilight turned to Rarity. “Some storm, huh? The Pegasus ponies sure have outdone themselves this time. I hope you and Applejack don't have any trouble getting home.”

“It may indeed be a problem," replied Rarity. "So, what's Jack doing here?"

"Fluttershy left to visit her family in Cloudsdale for a few days. Jack's staying with me to keep ponies from getting suspicious," Twilight explained.

"I suppose it would be a bit suspicious if Fluttershy left Jack home alone after all the time she spent being so overprotective," Rarity noted.

“Hey, if you and Applejack need a place to stay for the night, Spike's in Canterlot on Royal business, and Jack's set up his sleeping bag in my study." Twilight offered before gasping. “You and Applejack should totally sleepover! We'll have a slumber party! I've always wanted one of those.”

“Oh! Uh, goodness. Uh, I do believe I have another engagement scheduled for this evening that completely slipped my mind until just now," Rarity said with a nervous laugh. “Ah, silly me, I can't possibly stay here all night… with Applejack.”

Twilight ran to a bookshelf and used her magic to grab a book from the top shelf.

Slumber 101: All You've Ever Wanted to Know About Slumber Parties But Were Afraid to Ask,” Rarity read.

“My own personal copy. It's a fantastic reference guide. You should see the table of contents. I've been waiting for a chance to use it, and today is the day! This is gonna be so great!” Twilight said, her face beaming with excitement.

“Yes, uh, great," Rarity said, nervously glancing out the window where Applejack was washing herself off with the hose.

2 minutes later

Jack walked down the stairs to find Rarity and Twilight, applying green mud masks to their faces. "What are you two doing?"

"They're mud masks, darling," replied Rarity. "Why don't you come join us?"

Jack glanced at the green mud and then at his phone, and then to Twilight’s study. “Nope!”

He walked into the study and grabbed his earbuds. With all outside sound completely drowned out, he made his way to the kitchen to raid Twilight's fridge.

"Well, that was rude," said Rarity.

Applejack then walked into the room and gasped. “What in tarnation... Now, wait just a goll-darn minute. Ya make me wash the mud off mah hooves, but it's ok for y'all tuh have mud all over yer faces?”

Kitchen

Jack rummaged through Twilight's refrigerator, trying to find something edible for him. Unfortunately, he wasn't having much luck.

Daisies? No. Hay fries? No. Isn’t there anything worth eating in here?" Jack wondered before noticing something on the counter. "Chocolate chip cookies, jackpot!

He entered the library room to find Rarity and Applejack arguing while Twilight looked gleefully stared into an open book. "This might be interesting, he thought, taking out his earbuds to see what they were saying.

“You know, there's fussy, 'n there's just plain gettin' on mah nerves," said Applejack.

“Fortunately, I can get along with anypony, no matter how difficult she may be," said Rarity.

“Oh yeah? Well, Ah'm the get-alongin-est pony yer ever gonna meet," said Applejack.

“That's not even a word," said Rarity.

“This is going to be the bestest slumber party ever! Yay!” Twilight exclaimed, hugging her friends.

"Yay," Rarity and Applejack said unenthusiastically.

Did Twilight just say bestest?” wondered Jack as he bit into a cookie. "Blegh!" he spat out the cookie. "Raisins!"

"That's completely undignified," Rarity scowled.

"I know, I know. I'm cleaning it up," Jack muttered.

"If you don't like raisin cookies, I've got chocolate chip as well," said Twilight, leaving to retrieve the cookies.

Twilight returned with the chocolate chips and asked, "who's ready for makeovers?"

"Nope!" Jack promptly refused.

When the ponies finished with their makeovers, Twilight checked it off her list and moved on to ghost stories.

“I'd like to tell y'all the terrifyin' tale of the prissy ghost who drove everypony crazy with her unnecessary neatness. Oo-oo!” Applejack said before looking at Rarity. “I'm sure y'all are familiar with that one?”

I wonder what's going on between those two," thought Jack as he munched on a cookie.

“Never heard of it, but I have a much better one. It's the horrifying story of the messy, inconsiderate ghost who irritated everypony within a hundred miles! Oo-oo!” said Rarity.

“All right, if nopony here can tell a good story, I will," said Jack. "Goddammit, I said nopony," he cringed as the lights went out. "It was a day like any day, and a boy was sent down to clean the basement. As he was cleaning, he heard a voice, "I am the ghost with the one black eye!" and he ran away screaming. Then his sister was sent down to clean the basement, and she heard the voice, "I am the ghost with the one black eye!" and she ran away screaming. Then the mother went down to clean the basement, and she heard the voice, "I am the ghost with the one black eye!" and she ran away screaming. Then the father went down to clean the basement, and he heard the voice, "I am the ghost with the one black eye!" and he ran away screaming. Finally, the baby went down to clean the basement, and the baby heard the voice, "I am the ghost with the one black eye!" and the baby said, "YOU BETTER SHUT UP, OR YOU'LL BE THE GHOST WITH THE TWO BLACK EYES!"

The ponies chuckled a bit at Jack’s story.

"Ok, it wasn't scary, but Ah'll admit it was pretty funny," said Applejack.

"I have one too," said Twilight. “This story is called The Legend of The Headless Horse. It was a dark and stormy night, just like this one. And three ponies were having a slumber party, just like this one...”

5 minutes later

“...and just when the last pony thought she was safe, there, standing right behind her, just inches away was--The Headless Horse!" Twilight finished as the lights went out again, and she put a sheet over her head, causing Rarity and Applejack to scream.

“Babies,” Jack said. “Jesus Christ, that was scary!

“Ghost story, check. Now, who wants s'mores?" asked Twilight.

“I do!” exclaimed Jack.

“Jack, you’ve just finished an entire box of cookies. How could you possibly want more food?” asked Rarity.

“Probably 'cause he’s just a growin' boy!” said Applejack.

"How rude! He only looks that way," Rarity scolded. "You know he's older than we are, and you know that he gets offended when we forget."

“Um, Rarity, it’s true that I don’t like it when you guys treat me like a child, but she’s right. While I'm an adult mentally, I still have the body of a child," Jack said, scratching his head.

4 minutes later

Jack nervously watched as Applejack roasted her marshmallows in the fireplace. "Who the Hell puts a fireplace inside a tree?

Rarity and Twilight stood around a table using their magic to make their s'mores. “Then you place one marshmallow on the top of the chocolate and be sure it's centered--that's critical--and then carefully put another perfectly square graham cracker on the top. And done. Ta-da!” Rarity said as Applejack walked to the table with her roasted marshmallow.

“Ooo!” Twilight said in awe.

“Nah, ya just eat 'em," Applejack said before scarfing the s'more down and belching.

“You could at least say excuse me," sighed Rarity. "I mean, look at Jack. He's a colt, and he eats more politely than you do."

“Huh?” said Jack as he looked up with a face plastered in chocolate.

"If ya had just given me a few seconds, Ah was about tuh say pardon," Applejack retorted.

After they finished with the s'mores, Twilight decided Truth or dare would be the next activity. Rarity and Applejack quickly hijacked the game for their personal squabble, and Jack started to get fed up. The pillow fight apocalypse that came next was the last straw, and he went to bed. Twilight came to the same decision, and the three ponies headed up to her room soon after.

Just as Jack was about to close his eyes, he heard Applejack and Rarity begin to argue again from upstairs. “Seriously?

The arguing went on for about three minutes before there was a loud crash.

What the hell are they doing up there?” Jack wondered as he got out of his sleeping bag.

He ran up the stairs to find a large tree branch had crashed through the window into Twilight’s bedroom. “What happened here?”

"Applejack had the brilliant idea to lasso a tree branch through the window," huffed Rarity.

“Ah wouldn’t have needed tuh if somepony had stopped trying' to spiffy things up and helped me take 'em down tuh begin with!” Applejack retorted.

“Enough!” shouted Jack as he pointed to the branch. “Don’t you have more important things to worry about?”

“He’s right. The book doesn’t say anything about branches!” said Twilight as she flipped the pages of her slumber party book. “Although it does mention camping, is that what this is?”

Well, Twilight’s broken," thought Jack. "Applejack, help me move this branch."

"Sure thing, you pull, and Ah'll push!" said Applejack, as she began to shove.

Jack grabbed the branch, but even with both him and Applejack working together, they still couldn't remove it.

"This isn't working," said Jack.

Applejack looked to where Rarity was trying to put books back on their shelf. “Rarity, stop fussin' about the small stuff and help us out!”

"Are you insane? I'll get all icky," Rarity responded in disgust.

“Are ya serious…” Applejack started as she realized what a jerk she’d been. "Look, Ah'm sorry. If Ah had listened to ya and not been so stubborn, this never would have happened. Ah know ya don't want tuh get dirty, but ah can't do this on mah own."

"Very well," Rarity said as she charged her horn.

In a snap, the massive branch was converted into several small topiaries.

Impressive," thought Jack.

Applejack moved to buck a remaining chunk of branch out the window but was stopped by a glare from Rarity. Seeing that she was about to act without thinking, Applejack carefully picked the piece up and dropped it out the window, which she quickly closed.

“U-ugh. Oh, I look awful," said Rarity, upon noticing that she was covered in grime.

In an attempt to make up with her friend, Applejack put two cucumbers over Rarity's eyes, "Better?"

Where did she even get those?” Jack wondered as he watched the two ponies hug.

“Oh, pretty! Where did these come from?” Twilight asked upon noticing the topiaries. “They're not in the book either.”

“Twilight, Ah’d like to give this slumber party another try," said Applejack.

“As would I,” agreed Rarity.

"Excellent, the next thing on the list is 20 questions," said Twilight.

Seeing that the commotion had died down, Jack decided to go back to bed, "Night Twi, night Rare, night AJ, I'm going to bed."

“Good night Jack!” they all said as he left.

Author's Note:

Not bad, considering the scare I went through at the ER. Could still use some editing, but I'm pretty satisfied with how this turned out.
Next time: Jack wakes up from one of his nightmares to find Twilight Applejack and Rarity standing over him with looks of concern. When he explains about his nightmares, they decide to get Pinkie Pie involved, and in a weird therapy session, Jack reveals the full story behind his nightmares. Meanwhile, Spike is interviewed by the Equestrian Royal Court.

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