Chain Gang O' Five

by GodOfBBQ

First published

The Mane 6 get arrested while on a road trip

Southern Equestria is where you could find the old fashioned ways the ponies long ago believed. From religious views, to laws and racial views. Those are only the few reasons why Southern Equestria is much different than the north. When the Mane 6; minus Applejack for working reasons, take a trip down to the South, searching for the next location the map tells them to go the craziest thing happens that not even Twilight's prestigious roll as Princess of Friendship could resolve.

They get arrested, now they must do everything in their power to return back to the North.

*Inspired by the film O' Brother, Where Art Thou*

New Destination

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New Destination

It’s nearly been two weeks since Twilight and the gang’s last venture given by the crystal map. And ever since they've returned home from their equality experience, Twilight, Applejack, Rainbow, Pinkie, Rarity and Fluttershy all wondered what might happen next on their journey.

Would they stumble upon a land where the town is ruled by a dictator that wanted the rule the world by killing all minorities such as Zebra, Griffin, and Dragon? Would they meet a different dictator who would threaten Equestria with highly dangerous weaponry? Or something much more worse?

Only time would tell. But what Twilight and her friends knew was that it was inevitable that there would be another journey they would have to go on. Whether it be peaceful or not.

And on this day, their next destination was decided.

~***~

Twilight woke up groggily from her bed in her bedroom. She yawned a quiet little yawn and began to climb out of her bed. Stretching her wings and hooves, she made her way downstairs to her kitchen.

Since the new improvements her friends made on her palace, it’s become much more homely now than before. Before it was cold, and foreign to her. Everything either having a crystal texture to it, or being entirely made out of crystal altogether.

Her kitchen, like Applejack had said, had an old fashioned Country look to it. With an old stove and fridge taking up small spaces of the wall. The cabinets and cupboards being made of wood, possibly oak giving the kitchen the sense of living in a peaceful farmhouse on the edge of town.

Twilight grabbed a mug from the cabinets and put it in a coffee machine. Making coffee was probably the extent to Twilight’s culinary abilities.

After waiting a bit, she grabbed her mug and began sipping from her glass as she made her way to the meeting room where the crystal map rested.

After walking through some more rooms and hallways, she finally made it to her destination in the palace. The meeting room.
She trudged and lifted her tired hooves over to the giant table where the map was and began to look over it.

‘Normal so far...’ She thought. As she was going for another sip of coffee, she noticed a tingling feeling where her cutie marks would be. She quickly swiveled her head to look them over to notice that they were glowing like before.

She then looked at the map to see her cutie mark translate onto the map. It moved around until it landed in the Southern spot of Equestria, like last time, in the middle of nowhere.

“I have to summon the others!” She exclaimed as she nearly dropped her mug of coffee. She began to illuminate her horn, it shined and twinkled until a flash of pink light engulfed the room. When the light dissipated, all her friends were there. Only one being awake, that one being Applejack who was usually up at the break of dawn.

Rainbow, Pinkie, Fluttershy, and Rarity all slumped over, sleeping in each of their chairs.

“Twilight!? What in tarnation is goin’ on here? You caught me just in the middle o’ picken’ apples fer the day! I gotta make a livin’ somehow!” Applejack exclaimed, obviously sounding annoyed that she was taken away from her morning duties as a farmpony.

“I’m sorry Applejack but this is important! The map is giving another destination! Look!” Twilight pointed.

Applejack strode over to where the map sat and looked it over.

“Hey, ain’t that in the South? That’s where the deserts of Appleloosa is! Why’s it pointin’ there Twi?” She asked looking back to her Alicorn friend.

“I don’t know, but I do know it’s important! Who knows what needs to be solved out there. It could be anything!” Twilight said looking at the map once more. As she looked at the location longer, Applejack’s, Rainbow’s, Pinkie’s, Rarity’s, and Fluttershy’s cutie marks joined Twilight’s in marking the destination.

All feeling the same tingling sensation Twilight felt, the sleeping ponies jolted out of their slumber to be confused to where they were and how they got there.

“The clown has no penis!” Pinkie slurred as she rose from her sleep.

“Oh yeah, there’s the spot right there… Hm? Well how on earth did I get here… Oh!” Rarity yawned,

“Hello Twilight.” She said wiping her eyes with a hoof.

“Mmm, yeah, rub that there! Oh yeah I’m a naughty little filly huh?” Rainbow cooed in her sleep, still not rising like the others. Her slurred words of sensuality making the others blush and wonder what she was dreaming of.

“Rainbow! Rainbow Dash!” Twilight called out, snapping Rainbow out of her slumber.

“Ah! I’m up, I’m up! What I miss?” Rainbow asked shooting up from her sensual state of slumber.

Twilight chuckled and shook her head.

“Nothing Rainbow, but I want you all to look at the map. It has another destination for us. Maybe somepony needs our help again.” Twilight suggested.

“Or another dictator needs another beating!” Rainbow suggested.

“Whichever it may be, those ponies; if any, need our help. Right Twilight?” Rarity asked.

“That’s right Rarity. It’s our duty to keep this land peaceful, and to keep everypony friendly with one another.”

“I agree with Twilight. If everypony in Equestria treated one another in a friendly way, it would be a nice place. Or, nicer maybe…” Fluttershy said in her trademark timid voice.

“So, I hope you all weren't busy this week. Because we’re going on another road trip.” Twilight announced.

“Okay. But you don’t need to announce a road trip every time a marker pops up on the map y’know.” Rainbow said with a chuckle. Twilight sheepishly grinned at her friends remark.

“Well, I’m not busy at the boutique. Mother and Father have Sweetie Belle for the week so I can come.” Rarity said with a kind smile.

“I got nothing planned… I’ll go.” Rainbow added.

“Me two.” Fluttershy peeped.

“Me three!!” Pinkie shouted excitingly.

All the eyes looked towards Applejack who had an unsure face.

“Ah don’t know y’all, I got a ton o’ work to do. And Big Mac and Granny will be real sore if Ah didn't do all the chores around the farm for the week.”

“Oh c’mon AJ, it’s not like you had a problem going last time! Besides, I’m sure they’ll let you go if it’s important stuff like this.” Rainbow assured.

“Yeah, Ah know. But this week’s supposed to be real busy fer us. I just don’t think I can manage the time. Is that OK Twi?”

“Of course, that’s fine. We understand, right girls?” Twilight glanced at her friends who all shared the same nod.

“Thanks y’all. Sorry, Ah couldn't make this one.” Applejack apologized.

“It’s fine. besides, I got a feeling this mission won’t be that long.” Twilight said. With a nod and the tip of a hat, Applejack left the group, leaving the other five to discuss the travel plans.

~***~

“So, we leave by this afternoon?” Rarity asked, wanting to assure the planned schedule.

“Yep!” Twilight answered.

“Hey Twilight! How much cake do you think I should bring!?” Pinkie asked.

“Cake? We won’t need cake for the trip Pinkie.” Twilight said with a chuckle.

“But, what if I have to eat more terrible food!? I don’t want to relive that experience with those awful muffins!” She pouted.

“But you ate your weight’s worth of cake after we fixed the town. Shouldn't that have made you forget?” Rainbow asked.

Pinkie only stared at Rainbow with a blank stare.

“Never forget… I will never forget…” She said in a creepy tone.

With the whole room filled with a dark tone. The others just went on with packing the necessities for the trip. Not saying a word about how eerily Pinkie made it.

After some more time packing, talking, and eating a quick lunch they began their trek to Southern Equestria, to solve the problems of ponies in need of friendship!

Dirt Road Leadin' to Nowhere

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Dirt Road Leadin' to Nowhere

The sun was out, the wind was periodic, but cooling, and five friends trudged along a dirt road leading to nowhere. But to them, it was leading to another friendship mission.

Twilight, Rainbow Dash, Pinkie Pie, Fluttershy, and Rarity had just got off the train, where it met the end of the line. Taking as far as the train could go south, the group of friends settled with their current position in their journey.

With four of them on hoof, and the other continuously flying, the group of friends made their way down the road that lead away from the final train station near Appleoosa.

To keep themselves entertained, Twilight and the others would toss around conversations here and there but their trip stayed mostly mute.

After some more time walking, Rarity and Fluttershy were becoming sore in the hooves, so they stopped to take a break on the side of the road. Every so often, seeing a farmpony pass by with a cart full of miscellaneous vegetables and fruits, that were somehow grown in the middle of the desert.

After taking a few minutes to catch their breaths, they began their walking down the path. Following the coordinates the map gave them.

After some time passed, the group of ponies became worried. Not seeing anypony for miles, let alone a town began to discourage them. It was getting sundown, Twilight and the gang all settled on making a camp for the night, knowing that it’d be too dangerous to keep going during nightfall.

“Goodnight everyone!” Twilight called out from within her tent. The others responded with tired “Goodnights” and soon after, everypony was asleep. All except for Fluttershy who was as stiff as a board. She tried oh so hard to fall asleep but couldn't. It’s been awhile since she’s actually been camping. As a matter of fact, she probably hasn't ever been camping.

All she could think about was, what could be awaiting them on their journey? Monsters? Demons from another dimension? Celestia only knows.

She shivered in her tent, so scared that she was making the tent shake along with her. Gaining the attention of one rainbow maned pony.

“What the hay?” Rainbow whispered as she got up from her stranded desert cloud. She looked down to see Fluttershy’s tent vibrantly shaking.

She hopped off her cloud and began to gently float down to Fluttershy’s tent.

Once in front of it, she tapped on the tent’s zipped up flap that substituted for a door.

The tapping elected an “Eeep” from Fluttershy who frantically crawled into a corner of the tent.

“Fluttershy, it’s me! Rainbow! What’re you doing in there?” She asked.

Fluttershy, realizing that it was only her technicolor friend, rushed to the zipped up flap and opened it.

“Oh, hello Rainbow…” Fluttershy greeted.

“Fluttershy, why was your tent shaking like that?” Rainbow asked.

“Oh, no reason. Don’t worry about me Rainbow, it’s fine. Just, go back to bed please.” Fluttershy insisted but was rejected by Rainbow.

“No, no something’s wrong. C’mon Flutters tell me.” Rainbow said in a stern voice.

“Well… It’s just, I haven’t been camping in the longest time, and I’m just worried of what’s out there in the desert. I’m also worried about what’ll happen on this friendship mission. I’m worried if something like last time will happen.” Fluttershy answered, sounding as if she was choking back tears.

Feeling bad for her timid friend, Rainbow entered the tent and sat down next to Fluttershy. As she nestled into her spot, she began to get into a sleeping position.

“W-What are you doing Rainbow?” Fluttershy asked, sounding confused as to why Rainbow was looking like she was about to sleep in Fluttershy’s tent.

“You’re scared aren't ya? I have to be with you now. So that way you won’t be scared. Simple as that.” Rainbow answered, turning over to face Fluttershy.

“Oh, you don’t need to do that Rainbow. I said I’m fine.” Fluttershy said, her assertiveness returning slightly.

Rainbow raised an eyebrow, making Fluttershy falter and agree to let her stay with her in the tent. Fluttershy then began to lie down next to Rainbow. It only took five minutes tops for Fluttershy and Rainbow to fall asleep. With Rainbow around, she was able to sleep blissfully. With no care in the world.

~***~

“Everypony wake up! We have go while it’s early!” Twilight shouted, Pinkie Pie already awake with her. They had just finished up cleaning up their tents, now it was just a matter of waking Rarity, Rainbow Dash, and Fluttershy. However, the two had no idea where Rainbow was, they just assumed she was sleeping on a moving cloud that didn't stray too far away.

Twilight went to Fluttershy’s while Pinkie went to Rarity’s. Twilight tapped on the zipped up flap on Fluttershy’s tent. While waiting for a response, she heard Pinkie Pie yell to wake Rarity who was so surprised by her sudden jolt out of slumber, nearly jumped out of the top of her tent.

Rolling her eyes jokingly, she turned her attention back to the tent. She tapped the flap again.

No response.

Getting annoyed by the failed attempts to wake Fluttershy, she used her magic to unzip the flap. As she unzipped the flap, she gasped at the sight she found.

Fluttershy was holding onto Rainbow, her head nestled into the crook of Rainbow’s neck as the two slept peacefully.

Twilight chuckled to herself. She found it funny how intimate the two looked together.

“Rainbow, Fluttershy! Time to wake up! We have to keep moving!” She called out.

Rainbow and Fluttershy both shot up in surprise as they began to clean up the tent, as if nothing happened. Both ponies looking wide eyed and surprised, not wanting to say anything.

“You two love birds better hurry, we’re all cleaned up and ready to go.” Twilight called out as she walked away.

“So… We don’t talk about last night right?” Fluttershy asked, as she began to fold the blankets.

“Right!” Rainbow quickly answered as she began wrapping up the sleeping bags. It took only five minutes for the two pegasi to have the tent and sleeping bags packed away and ready to go.

As soon as everypony was ready and packed up, they began to walk down the dirt road that seemed to lead to nowhere.

~***~

Unlike yesterday, the group of friends were more talkative. Most of them being in good moods, surprising that most of them were either very rudely woken up or hardly got any sleep at all.

However, conversations between Fluttershy and Rainbow were short lived or didn't exist at all. The two were too busy thinking about the night before. Every time Rainbow looked over at Fluttershy, she would always blush and look away with a sheepish smile across her muzzle.

No matter how much prodding or dissecting the other three friends would do, neither Rainbow or Fluttershy would tell what happened the night before.

~*Night Before*~

Fluttershy stirred awake, feeling slightly more warm and comfy than before. On account that she first started out sleeping on the floor of a tent, that felt more like sleeping on the desert ground itself.

She turned her head to find Rainbow mane blocking her sight. Wondering why there was technicolor mane tickling the top of her muzzle, she tried to sit up before noticing Rainbow Dash holding on tight to Fluttershy.

Blushing, Fluttershy said,

“Rainbow… Rainbow, why are you cuddling me?”

Rainbow, who was only half awake answered,

“Hmm… Because you feel nice. You’re soft, and warm…”

Fluttershy’s face turned a deep shade of crimson

“Oh, well, I… Rainbow, I-”

“Shh” Rainbow hushed Fluttershy as she rose to sit up with Fluttershy. Rainbow laid her hoof on Fluttershy’s muzzle, making her stop talking.

“Let’s not ruin this moment Flutters… I want to be straight with ya, I… I think I like you… I, like you a lot. And, I came down here because yeah I was wanting to care for you, but I also wanted to be with you… So, yeah.”

Rainbow was too busy looking down to notice Fluttershy’s deeply blushed face. She had tears in the corners of her eyes, tears of happiness. Without warning, Rainbow felt Fluttershy hug her tight. After she received the hug from Fluttershy, Rainbow was met with Fluttershy’s face, they looked eye to eye before locking lips.

Rainbow went wide eyed, never thinking that her simple confession would bring this much affection from Fluttershy, but she took it anyway.

The two fell to the tent floor, still continuing their loving embrace with no interruptions.

~*Current Time*~

As the five made their way down the road, Rarity began to complain.

“Oh, when are we going to get there! It’s hotter than ever, and my hooves hurt from walking so much.”

“How about I fly up and see if I can’t spot any town or something. I’ll look for a Buffalo settlement if possible.”

“Good call Rainbow!” Twilight said while watching Rainbow fly higher and higher into the humid blue sky.

After some time, Rainbow began to call out,

“Hey! Hey, I see a town! I see a railroad in the town!” She sounded excited, this had to be good.

“Really? Let me see!” Twilight flew up with Rainbow to see for herself. And it was no fib, there was a small town, bigger than the town from their equality mission, but smaller than Ponyville. This town possibly had a train station, on account that a railroad system could be seen trailing out of the town.

“I see it too! We have to get there! Maybe that’s the location the map told us to go to!” Twilight exclaimed. Her and Rainbow flew back down to tell the others that they've spotted a town.

All of them getting a new sense of excitement from this news, began to rush down the dirt road. Hoping that this would be the last bit of walking they would need to do.

Wingers

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Wingers

It didn’t take long for the gang of friends to arrive in the small town. It seemed to be very well populated, on account of ponies entering and exiting shops along the main road. However, the only odd thing about this town was that there were no other species but Earth Pony and Unicorn. No Pegasi to be seen.

The girls simply took this as a coincidence but Rainbow and Fluttershy kept getting odd stares of disgust and anger from the ponies who would pass by.

As they went on, it got more apparent that there were no Pegasi in the town whatsoever. It was no longer just a coincidence, something was wrong here.

Wanting to dig a little deeper into this problem, Twilight stopped a passerby stallion who balanced firewood on his back.

“Excuse me sir, but do you know where we could find the leader of this town? A mayor maybe?” She asked kindly.

“Well sure, you’d want to keep goin’ down ‘till you find a three story white buildin’. That be the town hall.” He informed to Twilight in a thick, welcoming, southern voice.

“Thank you sir!” She said as the stallion walked down the road in the opposite direction. As the stallion passed Fluttershy and Rainbow he frowned and grumbled,

“Damn Winger…”

The name made Rainbow frown in confusion.

‘He didn’t just use the “W” word did he?’ She thought as she followed Twilight and the others to town hall.

~***~

They finally made it to town hall, it was modest, but had a luxury to it that helped it stand out from the commoner buildings of the town.

Though the outside of the building was wood but painted a nice coat of white, the inside was one of a castle’s inside. It had leather furniture, beautiful maroon wallpaper, dark mahogany wood floors, and business mares and stallions looking very trimmed and proper.

Being impressed with the proper ways of the town hall, Twilight stopped another stallion, with; like the wallpapers, had a maroon coat of fur with dark brown mane combed over.

“Yes Ma’am, how may I help you?” He asked, with the same thick country accent as the stallion before had.

“Yes, I request to see the mayor of this town. I wish to speak with her about a situation we’ve been sent here to resolve.” Twilight said formally.

“Of course ma’am, but first, do you have an appointment to meet Mayor South.”

Twilight paused, Rarity picked up where she left off in the sentence.

“Uhm, we don’t have an appointment kind sir. But, maybe you could show us to her anyway. We’re here on Princess Twilight’s order.”

“And I’m assuming this is she.” The stallion said, “Well in that case, please follow me Princess. Bring your friends too.” He began to lead the group up the stairs before stopping and turning his head.

“Uh, Princess, please be kind enough to leave your… Pack mules in the lobby here. Their kind, isn’t allowed within the office of Mayor South.”

“Pack mules!? Listen buddy, you better take that back or else!” Rainbow threatened as she flew up to the maroon stallion.

“Please ma’am, keep control or else I’ll have to summon the constable!”

“You’re gonna have to summon the whole Equestrian army pal!” Rainbow retorted.

“Rainbow, please calm down. He didn’t mean anything by it. Just let Twilight handle this.” Fluttershy begged.

Rainbow growled but backed off.

“Fine, but hurry Twi. Celestia knows how long I’ll be able to keep calm.” Rainbow said settling down next to Fluttershy.

With a nod, Twilight followed the maroon stallion’s lead, along with Pinkie Pie and Rarity. Once they were up the stairs and out of sight, almost every pony in the room looked at Fluttershy and Rainbow, with a face of disgust.

“You have some nerve comin’ here ladies!” A mare said from behind the reception desk.
“Why don’t you two just follow me outside… Where you belong.” A stallion said as he began to pull Fluttershy with him towards the door.

“Hey! Let go of her!” Rainbow exclaimed.

“Rainbow, it’s fine. Let’s just do what the stallion says. It won’t take Twilight long, I promise.” Fluttershy reassured.

Rainbow growled again, but she began to reluctantly follow Fluttershy out the door.

Once outside, the two mares were left with the angry shout from the stallion,

“Wingers!”

After slamming the doors, Fluttershy turned to Rainbow who was red with anger.

“Rainbow, what’s a ‘Winger’?”

~***~

Twilight, Pinkie, and Rarity stepped through the double doors leading to Mayor South’s office.

“Mayor South, may I introduce Princess Twilight Sparkle, and her friends Rarity and… I’m sorry miss, I didn't quite catch your name.” The maroon stallion turned to Pinkie.

“The name’s Pinkie Pie! Nice to meet you! Hey Mister, we didn't quite catch your name! Would you mind telling us!?” Pinkie asked with excitement.

“Why, aren't you an energetic one? Well, my name’s County Document. Or my friends call me Doc. But, please may I introduce you to Mayor South!” Doc announced as he gestured to the stallion behind the desk.

The stallion was a bearded, middle aged unicorn with red mane, dark blue fur and pure white eyes. Giving him the illusion of being blind.

“Well, welcome to Beaten Path! The town with soul, in a land without none.” Mayor South greeted.

“Pleasure to be here!" Twilight said with a smile. "I am Twilight Sparkle, and this is Rarity and Pinkie Pie. Two other of my friends came along. They’re Fluttershy and Rainbow Dash.”

“Well aren’t those nice names… So, tell me your hig-” Mayor South was interrupted by Twilight.

“Sorry, not to interrupt, but I prefer just Twilight.” Twilight insisted.

“Right, my bad. Uhm, Miss Twilight Sparkle, what brings you and your friends to our little town?”

“Well, we were actually sent here. We’re the elements of harmony and I’m the princess of friendship so it’s our duty to Princess Celestia to make sure friendship and kindness run through all of Equestria to make it a kinder and more peaceful place.”

“I see, well you may have made a wrong turn from down that road down yonder, ain’t nothin’ gone wrong here. Well, nothin’ since the breakout of ‘37. When three of our prisoners broke out of prison a while back. But, ever since nothin’s been happenin’ here since.” The mayor said as he rose up from his seat behind his desk. He waltzed over to a large window that looked over the main road.

“Well, there has to be something. The map wouldn’t just tell us to go somewhere that hasn’t had a problem for over seventy years!”

“Oh dear, please don’t tell me I dragged my hooves over hot sand for nothing!” Rarity pouted.

The room was silent, before Rarity piped up once more.

“I said I hope I didn’t dra-”

“County Document… What’re those Wingroes doin’ down there? Shouldn’t they be in the fields?” Mayor South asked as he spotted Fluttershy and Rainbow conversing with one another.

“Oh, well Miss Sparkle here said they were her friends, I assumed they were her pack mules at first but she made sure to correct me. She said the two traveled with them.”

The mayor didn’t make any eye contact, he stayed turned away from the group of ponies in his office.

“Miss Sparkle, I understand that being of royal authority comes with it’s benefits but that doesn’t mean you can walk into my town, and disrespect it’s laws. I don’t know why County Document didn’t tell you this before, but I’m tellin’ you now that Pegasi aren’t aloud in these here parts.”

‘This could be the reason why we’re here!’ Twilight thought to herself as an odd sense of excitement for what they might encounter came upon her.

“Care to explain why you don’t allow Pegasi in Beaten Trail Mayor South?” Rarity asked.

“Yeah! Why don’t you allow Pegasuses-Pegasus, Pegasi? Pegasi! That’s the word! Pegasi in your town? Some of the nicest ponies I know are Pegasi! And I know a lot of ponies! Like, I remember this one time-”

As Pinkie carried on with her seemingly endless story, Twilight asked the mayor,

“Mayor South, is it a speciest reason why you don’t allow Pegasi in your town?”

“You haven’t heard Miss Sparkle? Pegasi are the creatures of the devil! Givin’ them wings so that they can attack the heavens directly! Besides religious points, they’re lazy, they don’t help one bit, and when they do it’s always disastrous. Not to mention, the jailbreak of ‘37 was the doin’s of Pegasi!”

“Oh don’t be ridiculous Mayor South, we all know that whole God and Satan word is all myth and camp stories. But how are Pegasi lazy? They control the weather!”

“Not here they don’t! The weather is God’s work alone! No Pegasi power behind it! Now, you've insulted my beliefs, my town’s laws, and now you’re trying to defend the Pegasi!? What in bloody hell’s the matter with you Miss Sparkle!?” The mayor exclaimed.

“Excuse me? I don’t mean to get loud Mayor South I mean to discuss this in a professional manner, and as Mayor I believe you should act with more professionalism! Now, it’s clear why we were sent here. We have to explain to-” Twilight was interrupted.

“Oh now you’re judgin’ how I run this here town huh? Well, I’ll show you what for Miss Sparkle! County Document! Get the constable! Take Miss Sparkle and her friends to the county jail for harboring two illegal Pegasi, for being non-believers, and for defyin’ my words as mayor! They will and must appear in court tomorrow mornin’!”

“What!? That’s ridiculous! You can’t arrest me on those charges!” Twilight shouted.

“And I can’t go to jail! I don’t belong in jail! I didn't even commit a crime!” Rarity added.

“And jail food stinks!” Pinkie exclaimed angrily.

“Add defiance to the charges County!”

“Right sir!”

Mayor South took one last glance at the three friends who wore faces of fear, anger, and confusion. He then said with a smirk,

"Welcome to Beaten Trail ladies! May God have mercy on your soul!"