Carry on my Wayward Pone

by ShadowBrony928

Rating: teen
Tags: Gore, My Little Pony: Friendship is Magic, Dark, Other, Comedy, Adventure, Crossover, Human, Main 6
Length: 1903

The Winchesters find a case in a small town in Michigan, where they run into an old friend. Little do they know where this little meet up will take them. Join them in the search for Abadon in the world known as Equestria.

When the Winchesters meet Crowley in a warehouse in Michigan where he gives them some troubling news. Even more troubling is that he, the Winchesters, and Castiel must go to a world filled with technicolor talking magical ponies, and warm touchy-feely friendship bullcrap. Will they succeed in their quest? Will Dean manage to stomach living in his worst nightmare? Stay tuned to find out!

Published 2015-07-01 23:00:02 UTC
Last updated 2018-10-30 03:52:24 UTC

Prologue

It was a night like any other. While most of the world was sleeping peacefully in their beds, Sam and Dean Winchester were tracking down a creature responsible for several deaths in the town of Garden City, Michigan. They tracked it down to the nearby woods and were investigating a cabin they believed it might be in.They looked around. In one hand, a knife with some sort of fancy engraving. In the other, a shotgun. Eventually,they reached a room where they saw a familiar face “Well, well, well. If it isn’t the Winchesters?”

“Crowley!” the long-haired Sam said “Should’ve known you were behind this.”

“As much as I love random slaughter fests, this is not my doing, Moose. I simply hoped you could help me track down the one who did. Abadon.”

“And why should we believe you?” Dean asked, not convinced

“Well, you hold the dagger. I don’t exactly have much choice, do I? I recieved word from the small few of my followers I have left that she has fled to another world. One where she could get away from you easily”

“And how the hell’d she manage to do that?”

“Witchcraft. Fortunately, I know the same ritual. I can get us there, let you and your Wingman take her down, and I can get us right back.”

“And what’s in it for you?” Sam asked, knowing Crowley would never help them out without him getting something out of the deal

“With Abadon out of the picture, I shall regain my place as King of Hell.”

“And you’re positive,she went to this other world?”

“As positive as 2+2”

“What do you think, Dean? Should we trust him?”

“Not like we got any other leads, Sammy. We don’t got much choice.”

“Well, we might need Cas’ help on this one.”

And, as if on cue, Castiel in his trenchcoat appeared “I’ve been listening in the entire time. Dean’s right. We don’t have much choice.”

“Ah, if it ain’t Halo Boy himself. Well, now we’re ready to begin.”
Crowley began the ritual as the four were soon transported away in a flash.

Chapter 1: What the Hell?

The four arrived in a strange new world. Everything looked all cartoony. Sam was the first to wake up. He held his head as he looked around “Where the hell are we?” They were on a hill outside of some little town. He tried to stand up, but realized something was wrong. He couldn’t stand up right. He looked down and immediately realized why. His arms, legs, hands, and feet were replaced with hooves as his whole body was covered in light-colored fur as there was a picture of a burger on his flank as he stood on all fours a pony. His long brown hair making him fit in perfectly as his tail matched its style. He looked over to the others, seeing them the same with different marks and hair of course. On Dean was a picture of the impala, on Castiel, was a picture of angel wings, and on Crowley was stereotypical demon horns. Dean and Cas were the next to wake up and examine their new bodies, followed by Crowley. Dean of course was freaking out.

“Sammy...please tell me I’m not...a freaking...pony.”

“Sorry, Dean. Wish I could. I guess this is how the natives look, so we have to blend in so as to not cause any suspicion.”

“Exactly, Moose. Now I’ve come to this world a few times before. Dean and Sam? Not very common names. And neither are those classic rock personas you seem to love so much.”

“So you’re saying we have to come up with some cutesy little fru-fru names?”

“Precisely”
Dean sighs as he puts his front hooves to his face in agony

“Wingboy over here could be Halo.”

“Isn’t that a video game?”

“Not as far as they know.”

they all nod in understanding. Castiel examines himself further as he notices a horn poking out on his forehead as Sam sees this and gets a confused look on his face “Why does Cas have a horn?”

“He’s a unicorn.” Dean exhales another groan at Crowley’s answer. “Have either of you come up with names yet?”

“How about Sabbath and Warrant?”

“Those will do for now. Not like we’re planning on moving here or something”

“Yeah, so anyways, how are we going to track her down here? She could be using any of these natives as her new meat suit to fake us out.”

“Believe me, I doubt she’ll even know we’re here. And if I know you three, you’ll find her.”

“Right. Well, I guess it’s to that town over there to ask around for information then. You ready Dean?”

“Just give me a few more minutes…”

“In a few more minutes, Abadon could quickly gain an advantage.”

“Fine…” Dean walks over “But I am NOT happy about this.” they begin walking towards the town.

“I say we split up. Cas, you and Crowley search that half of town. Dean and I will search this one.” the others nod in agreement.

Dean lets out one more groan “Let’s get this over with…”

And with that, Dean, Sam, Castiel, and Crowle-I mean Sabbath, Warrant, Halo, and Crowley began making their way towards the town known as “Ponyville.” Will the four find Abadon before it’s too late? Will Castiel figure out how to convert his heavenly powers to magic to use in this form? And WILL Dean suck it up and take one for the team?

“I heard that!”

Find out in the next exciting chapter of Carry on my Wayward Son!

Chapter 2: Friendship is Magic, my Ass!

They soon arrived at the town. Sam/Warrant and Dean/Sabbath on on half and on the other was Castiel/Halo and Crowley. As Sam and Dean looked around, they noticed the other ponies were much more colorful than they were. Obviously this only added to Dean’s frustration. Eventually, he worked up the courage to go with Sam up to this pink pony with dark pink hair and blue eyes with balloons on her flank. Sam takes a breath and speaks “Hello. I’m Warrant, this is my brother Sabbath. Would you mind if we asked you a few questions?”

“Okie dokie lokie. I don’t think I’ve seen you around here before.” she gasps as she goes on one of her usual hyperactive rants “Are you new to Ponyville? You must be new to Ponyville because I know everypony in Ponyville and I’ve never seen you around here before. What did you say your names were?”

Dean gets slightly annoyed by the sugar-obcessed pony’s hyperness “easy there, Pinky!”

She gasps again “Oh my gosh, you know my name! How do you know my name?” Dean groaned once more

“He didn’t. It was just a figure of speech, but your name is actually Pinkie?”

“Yep yep yep! Pinkamena Diane Pie, but everypony just calls me Pinkie Pie.”

“Okay. So, Pinkie have you noticed anything strange around...Ponyville?”

“Strange? I can’t say so. Other than you two showing up, everything’s been quite normal around here” said the talking bright pink pony in a world where horses are technicolor and can fly and do magic.

“Are you sure? Nothing odd whatsoever? Like maybe a smell of sulfur or somepony with fully black eyes?”

“Nnnnope.”

“I see. Well thank you for your time.” he goes to Dean

“Wait a minute. You didn’t think I’d let you leave without letting me throw you one of my special welcome parties. After all, anypony in town will tell you nopony throws a party quite like me...except maybe Cheese Sandwich...Oh well. He’s not in Ponyville right now, so it’s just little old me.”

“We’d love to but we’re only stopping by for a little while. I doubt we’ll have time.”

“Okay, well be sure to let me know.”

“We’ll keep you posted.” the two walked away, now both annoyed by the bright colors and ponies everywhere. Then Dean realized something. He hadn’t eaten before the transportation and he was hungry as a bitch. He checked his jacket pocket to see if there was their fake credit cards in there. Instead, he found about 50 little coins “What the hell?” he took one out “Guess this must be the currency here. At least there’s no little fru-fru design on it. Hey Sammy, think we can see if they have pie in this godforsaken town?”

“Welllll” they heard a familiar voice as they turned around and saw Pinkie behind them “There’s plenty of pie in Sugarcube Corner.”

“Warrant?...Did she just say what I think she said?” Sam nodded “Would you mind showing us the way?”

“Absolutely. Anything for my new friends.” She led them to a large building at a corner. They entered as Dean saw the display case of the little bakery as his mouth watered

“There’s hope...they have pie…”

Chapter 3: (Insert clever chapter title here)

Crowley knocked on the door of a boutique in the town "Now, let me do the talking, halo."

"Fine. You better not be up to any funny business." Castiel was clearly not at all liking the idea of Crowley taking the diplomatic approach, but he did seem more familiar with this world then he was, so he had no choice but to go along.

"Don't worry. It'll be fine" Crowley had a smug little grin on his face at having the angel wrapped around his hoof

A white unicorn mare came and answered the door, her curled purple hair elegant and her blue eyes blinking "Oh. Why hello again, darling." she said, seeming to recognize Crowley

"Yes, hello again, Miss Rarity. Would you mind if my friend Halo and I ask you a few questions?"

"Not at all. Please come in." she opened her door and allowed them to come inside as they each sat on a chair and she laid on her luxurious sofa "So, what ever could I do for you?" she then noticed Castiel in his tan trenchcoat "Except maybe a new style for your friend here, that is."

Cas looked over his outfit and realized it wasn't exactly fitting in this new world.

"Maybe some other time. We're on a bit of a tight schedule here."

"Fair enough, darling. So what did you want to ask me?"

"Have you noticed any unusual happenings around um...Ponyville?"

"Well, I can't say I have, Halo. Though I'll be sure to let you know if I do. Anything else?"

"Have you seen any out-of-the-ordinary mares walking through Ponyville?"

"Well...honestly, Hellion, I can't say I have...but again, I'll be sure to let you two know if i do."

"I see. Well thank you for your time, Miss Rarity. Always a pleasure." Crowley and Rarity shook hooves as they smiled.

Rarity finally took the time to look over Halo's trenchcoat and tie with dread "Oh dear...perhaps um...while you're here, I could fix you two up some new clothes"

"We should really get going"

"Oh, but I insist, darling."

Halo rolled his eyes and gave in, clearly seeing there would be no way to worm out of this without revealing the true reason they were here. And so the two sat as their measurements were taken forcibly "I should have something ready sometime tomorrow. See you then"

The two nodded and left "I hope were not still here tomorrow. For Dean's sake at least..."