• 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 31: Unwanted Affection (Last Edited: 9/30/2022)

August 25, 2020

Sweet Apple Acres

Cheerilee had gone to visit her family, so class had been canceled for the day. That was most likely the reason the Crusaders had been allowed to have a sleepover on what usually would have been a school night, but Jack didn't really care about that. What he did care about was the fact this gave him plenty of free time once he finished cleaning up after all the animals. Seeing that Fluttershy was still sore about his irresponsible behavior, he decided it'd be better to hang out somewhere else for the time being, which is why he chose now to see if the Apples needed any help around the farm.

Before he even had a chance to knock on the Apples' front door, it swung open, and out came Apple Bloom. "Hey, Jack! What are ya doin' here tuhday?" she asked with an eager grin.

"I was gonna ask Applejack if she needed any help around the farm," Jack answered.

"Oh…" Apple Bloom said, slumping her shoulders in disappointment. "How long do ya reckon that'll take?"

"Dunno," Jack shrugged. "Why do you ask?"

"Well… I was jus' thinkin'," Apple Bloom started, blushing profusely. "Maybe ya might want tuh…"

"Want to what?" Jack asked after a few seconds.

Her face turning as red as her mane, Apple Bloom closed her eyes and shouted, "Would ya like tuh go see the Little Seapony with me?!!"

"That new movie playing at the theatre?" Jack asked. "Sure thing," he agreed, patting Apple Bloom's head. "How about we go tomorrow morning?"

"Really?!" Apple Bloom asked, her face bright with excitement.

"Yeah, sounds fun," Jack confirmed with a smile.

"Yes!" Apple Bloom cheered under her breath.

As Jack ventured inside, he was greeted by Granny Smith, who'd been knitting what looked to be a small hat, "Well now, if it ain't Apple Bloom's funny lookin' special somepony. Ya, here fer a little rendezvous?"

"Granny!" Apple Bloom objected.

"Now, back in my day, the colt would come to the head of the family and ask permission before taken' a filly out on a date, but I guess the youngins are doin' things differently nowadays," Granny Smith rambled.

"It's nothing like that, Mrs. Smith," Jack said. "Me and Bloom are just friends. I'm actually here to help Applejack on the farm. Where might I find her?"

"Applejack is out makin' a delivery," Granny Smith answered. "If'n yer wantin' to help out Ah think Big Macintosh is patchin' up the barn's roof."

"Thank you, ma'am," Jack said, bowing his head respectfully.

Sweet Apple Acres: Barn

Big Macintosh was in the middle of stripping off a patch of damaged shingles with a pry bar. Being an earth pony, he couldn't use magic to handle tools and was forced to use his teeth instead. He'd done this many times, of course, but that didn't change the fact that his equine form wasn't well suited for this kind of work.

He'd have liked to hire a unicorn or a griffon for that, but between how much they had to pay in taxes as peasants and how much it would cost to buy new shingles, to begin with, that wasn't an option. Not that he'd ever hire someone outside the family if he could. As convenient as that would be, hiring outside the family wasn't the Apple Clan way.

Then there was Jack. For reasons beyond Big Mac's understanding, Applejack had been paying a strange colt from Apple Bloom's class to help out around the farm. He could tell Apple Bloom had a crush on the human child, but that hardly made him family. As far as he could tell, Apple Bloom's feelings for him were in no way mutual. Still, Jack's hands made him an immense help with repairs, and Big Mac certainly wouldn't say no to his help right now.

"So, Jack, Ah was jus' wonderin' what ya think of Scootaloo and Sweetie Belle?"

Big Mac's ears perked up. "Speak of Discord, and he'll appear," he thought to himself, looking down to see Jack and Apple Bloom walking over to the barn.

"Sweetie Belle's smart and incredibly kind, and Scootaloo is one of the bravest, most determined ponies I know," Jack answered honestly.

"What about Sakura?" Apple Bloom asked.

"Honestly, I'm not sure," Jack said. "When I first talked to her, she came off as incredibly rude, but now that I've gotten to know her a little better, I feel like we have something in common. I'm not really sure what that something is, though."

Apple Bloom seemed disappointed by that answer. "And what about me?" she asked.

"You?" Jack asked, stroking his chin in thought. "You were the first pony in our class to be my friend, and our friendship helped me get used to life here in Ponyville. To be honest, I think our relationship is something special, and I treasure it more than just about anything else," Jack answered, pounding a fist over his heart."

Apple Bloom's heart raced as fast as lightning. She wanted to say she thought their relationship was special too, but instead, she just squealed and ran back to the house.

"Where are you going?!" Jack called after her.

Apple Bloom gave no response and simply ran inside, leaving Jack as confused as a cat trying to catch a laser pointer.

"You up there, Big Mac?!!" Jack called once he'd determined Apple Bloom wasn't coming back out.

"Eyup!" Big Macintosh answered.

"Need any help?!"

"Eyup!"

Jack climbed up the ladder and stepped out onto the roof. Once he'd seen the problem, he got to work helping Big Mac with the repairs. After a few minutes of removing damaged shingles, he tried to strike up a conversation with the reticent stallion. "Have you noticed Apple Bloom acting a little weird lately?"

"Nope," Big Macintosh answered bluntly.

"You sure?"

"Eyup."

"It's just; she's been asking a lot of weird questions lately," Jack elaborated. "I mean, I kinda understand asking me to go to that girly seapony movie with her since we're friends and all. But why would she be so interested in what I think about our other friends?"

Big Mac gave Jack a blank stare.

"What?"

"You seriously don' know?" Big Mac asked, breaking his habit of one-word responses.

"Know what?"

"Mah sister likes you."

“I never would have guessed that my best friend likes me!” Jack responded, rolling his eyes.

"No, Ah mean she has a crush on you," Big Mac corrected.

Jack's mind froze as if it were attempting to search for a response with Internet Explorer. A few seconds later, he burst out laughing. "Good one, Big Mac! I never took you as the funny type."

Big Mac simply stared as Jack continued cackling.

As he noticed Big Mac's silence, Jack's heart sank. "You… you're serious?"

"Eyup."

"But that would mean…" Jack started, thinking back to Apple Bloom's invitation to the movies. "She invited me on a d-da-dat… oh, God!"

Fluttershy’s Cottage

Upon learning the nature of Apple Bloom's feelings for him, Jack found himself unable to focus on the repair work and asked if he could go home. Now he was lying down on his bed, staring at the ceiling. "I can't go out on a date with Bloom! We're not even the same species, and she's like a third my age!" Biting his nails, he thought about when he'd walked into class with Sweetie Bell the day after the ursa minor attack. The way Apple Bloom had behaved, it should have been obvious she was jealous of Scootaloo and Sweetie Belle. How had he not made the connection at the time? “DAMN YOU ASPERGER’S!!!!" he shouted at the top of his lungs. "What if I tell her no? I could just say I'm not into her that way." He facepalmed at the thought. "That would hurt her feelings, though. I can't do that!"

August 26, 2020

Sweet Apple Acres

Jack hadn't gotten a wink of sleep last night. Every time he came close to nodding off, his mind was bombarded by thoughts of the Equestrian equivalent of the FBI swarming the cottage and hauling him off for agreeing to go on a date with Apple Bloom.

"I just have to tell her I don't feel the same way as she does," Jack thought, rubbing the shadows beneath his eyes as he waited outside the Apples' house.

The door swung open with a click, and Apple Bloom walked out. She'd clearly done a lot to prepare. Her coat glistened in the sunlight, her usual bow was nowhere to be found, and her red mane had been braided into a ponytail. Her actual tail had been done similarly. "Hey, Jack!" she greeted. "Ya ready for the movie?"

"About that," Jack said. "Bloom?"

"Yeah?"

"There's something I need to tell you…"

"What?"

"I think there's been a mis…" Jack paused, looking into his friend's eyes. "Why does she have to be so adorable?" He had no romantic interest in her, or any pony for that matter, but he couldn't deny there was something about his new friends. As disgusting as it felt to think this about another sapient being, looking into Apple Bloom's eyes gave him the same feeling as looking into the eyes of a puppy dog. He couldn't bring himself to say something that would make her sad. "Never mind, Bloom. We should go. If we don't hurry, we'll be late."

Ponyville Theatre

"What were you thinking, Jack?!" Emerald Jack screamed at Jack as he and Apple Bloom waited in line for the tickets. "You had one job! All you had to do was turn her down!

"Easy for you tuh say!" Jack retorted. " Yer not the one who would have tuh deal with her crying!

"You're going to be the one crying if Applejack finds out you took her underage sister on a date!

Sweat poured down Jack's face.

"You didn't think of that, did you, moron?

Shit!

"Welcome to the Ponyville Theatre," greeted a mare in the ticket stand. "How can I help you today?"

"Two foal tickets for the Little Seapony, please," Jack requested.

"An excellent choice, sir!" the mare said. "Your date is a lucky filly!"

"This isn't a date!" Jack denied loudly, drawing the attention of the ponies in line behind them. "I mean, me and Bloom are just friends."

"My apologies, sir. I hope you and your friend enjoy yourselves," the mare said with a wink.

"Just give me the tickets," Jack grumbled, dropping 12 bits on the counter.

Inside the theatre

The film had gone out for about an hour now. In order to avoid thinking about his date with Apple Bloom, Jack had decided to look for similarities between this movie and the Little Mermaid. Unfortunately, this hadn't provided much stimulation for his mind, as the two movies were pretty much exactly the same, as if someone had taken the film from his world and said, "what if this, but with ponies!"

The movie had now reached its equivalent of the song Kiss the Girl, which had underwhelmingly been renamed Kiss the Filly. As he tried to watch the film, he felt something warm in his hand. Slowly turning his head, he found Apple Bloom had placed a hoof in his open palm. "Bad touch! Bad Touch! I need an adult!" Jack mentally screamed.

You are an adult,” Emerald Jack reminded him. "And she's just touching your hand, you big baby."

Outside the theatre

When the film was over, Jack walked out of the theatre, clenching his chest and sweating profusely. He had a sharp pain in his chest and felt like the world was spinning around him. All he could think about was that Applejack was probably going to kill him now.

"Ya wanna get sum ice cream?" Apple Bloom asked.

"I think I'll just go home now," Jack stated blankly.

"Ya sure?" Apple Bloom asked.

"I don't feel so well!" Jack shouted as he rushed toward Fluttershy's cottage.

Fluttershy’s Cottage

Fluttershy was in the middle of throwing out expired animal feed when Jack burst through the door.

"Oh, hey, Jack. How was your…" She began,

"Don't want to talk about it!" Jack shouted as he rushed up the stairs.

As soon as he was in his room, Jack retreated beneath his covers and tried to go to sleep. Thirty minutes later, and he hadn't had any luck.

There was a knock on the door. "Ya in there, Jack?!"

Jack's heart sank. It was Applejack.

"Ah'm comin' in!" Applejack declared, opening the door with a click. "You alright, sugarcube? Apple Bloom seemed mighty worried 'bout you when she came home."

"I'm sorry, please don't kill me!" Jack pleaded.

"Kill ya?" Applejack asked. "Why in Equestria would Ah ever do that?"

"Because…" Jack explained exactly what had happened starting from the moment Apple Bloom asked him out.

"Well, that is a problem," Applejack acknowledged when Jack finished. "Let me ask you somethin'."

"What?"

"Has Apple Bloom actually told ya her feelin's?" Applejack asked.

"Well, no, actually," Jack answered.

Applejack smiled. "If yer problem is that ya don' want tuh make her sad, then dontcha think you should at least wait 'till she has the courage tuh tell ya how she feels before ya turn her down?"

"But isn't it inappropriate for me to let her go on thinking about me like that?" Jack asked. "Since I'm not really a child."

"Ah won' lie tuh ya, Jack," Applejack responded. "This situation is more complicated than Ah'm equipped to handle. It's never appropriate for a foal to be with an adult, and usually, it would be necessary to nip this in the bud as soon as possible. But she can't know that yer not her age. Nopony in town, apart from the six of us who found ya, can know that. It's not like you can just tell her the truth." Apple Jack placed a hoof on Jack's shoulder. "Knowin' mah sister, Ah reckon it'll be a while longer before she gets it in her mind tuh confess. If ya turn her down before that without any explanation, it'll break her heart. Then Ah really would have tuh kill ya," she joked.

Sugarcube Corner

Sweetie Belle walked into the bakery, intent on talking to Sakura. She didn't care what the others thought. She still didn't trust her.

"Welcome to Sugarcube Corner," Carrot Cake greeted. "Oh, hello there, Sweetie Belle. You're not here for another try at a baking cutie mark, are you? I just fixed the ovens from the last time you Crusaders were here. Speaking of which, where are the other Crusaders? It's unusual to see you here by yourself."

"Just me today, Mr. Cake," Sweetie Belle said. "Is Sakura here?"

"She's in her room with her friends from class," Carrot Cake answered. "She's quite popular with those colts."

"Is it alright if I go see her?"

"Of course," Carrot Cake nodded. "Second room on the right."

"Thank you," Sweetie Belle said.

Sakura’s Room

Oni-Hime had made use of the enthralled colts from her class by having them act as spies around the town. She'd been having them meet up with her in her room every few days to give their reports. "What have you found out about Captain Shining Armor, Rumble-san?" she asked.

"Captain Shining Armor plans to return to Canterlot next week since Twilight Sparkle's almost made a full recovery," Rumble answered.

“Arigatō, Rumble-san,” Sakura said. "What about you, Pip-san?"

"The Mayor…" Pip began before being interrupted by a knock on the door.

"Could you get that, Pip-san?" Sakura asked.

"Of course," Pip agreed, opening the door.

"What are you up to?!!" Sweetie Belle asked accusingly once the door was open.

"That's an interesting way to say, kon'nichiwa," Sakura said with a smile. "Leave us, colts."

Once the colts had left, Sakura's smile was replaced with a glare. "It's rude to barge in uninvited, Sweetie Belle-san."

"I know you're up to something, Sakura," Sweetie Belle accused. "What were you really doing in the forest?"

"I told you I was getting my coin," Sakura said innocently. "It's very important to me."

"I don't believe you," Sweetie Belle glared.

"But the others do," Sakura said with a smirk. "What makes you think I'm lying?"

"I heard you talking to Snips and Snails about the ursa minor attack in Sugarcube Corner," Sweetie Belle explained. "That same day, the three of you led a hydra into town!"

"I already told you I was trying to get this," Sakura said, holding up her coin. "Unless… you have some evidence that says otherwise?"

Sweetie Belle didn't respond.

"That's what I thought," Sakura said with a smirk. "It's not nice to make accusations, Sweetie Belle-san. Somepony might take it personally."

Author's Note:

That took longer than expected. As those of you who read my blogs know, I have graduated from college now and am working full-time as a pizza driver until I can land a job with my degree. I had an interview with a local state park a little while back, but unfortunately, I haven't heard back from them yet. Luckily the pizza job gets me really good tips, and I'm more than able to keep up with my rent, utilities, and groceries.
Next Time: Jack and the Crusaders enter the school talent show.

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