Captains of the Sky

by Smexy and Boss Inc

First published

The skies of Equestria are dominated by the Airshipping industry, the are many who take advantage of this. These are their stories.

The skies of Equestria are dominated by the Airshipping industry, the are many who take advantage of this. These are their stories.

The Manual: A Guide to Story

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Captain Anastasia

The Iron Keep

_____________________________________________________

Captain Flynt

The Quick Draw

Flynt's Sidearm

the hunt

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The sky’s above Equestria were always calm, the air ships that went from city to city were uninterrupted and trade was profiting. Relations between the human governments and the Equestrian Princesses were getting along fine as well, but from the good of this time period also brewed some more sinister individuals. Some were in it for the bits, others in it for the adventure but all of these individuals were known as the ‘Predatori Cielo’.

“HAHAHAHAA!” A man laughed crazily as he twirled his cutlass in the air. A leather patch covered his left eye, as his long, coal black hair was waving in the winds as his ship flew through the sky. He was a tall man, covered in a long leather coat with it’s right shoulder being plated in metal, along with a vest on the underside of the coat which covered a white shirt. His legs were covered in a set of beige trousers that held a belt and holster along his hip. “Tis a wonderful day to be raiding the sky for the ship of Captain Flynt!”

Not far behind him was another airship, its captain smiled as she looked down at the ground below. Her blonde hair was pulled back into a braid, her blue eyes filled with excitement. She wore a long leather jacket and an ushanka atop her head. Beneath her jacket was a green tank top and her pants were black denim. On her feet was a pair of leather boots and at her left hip was a Torkarev TT-33 handgun, and on her right was a cavalry sabre. “Helmsman... Raise the Quick Draw on the radio.” She said in a thick russian accent.

“Aye Aye captain.” Another accented man said before speaking into the radio. “Here captain.” He said handing the radio to the woman.

“Hello~ Anna!” The crazed man laughed into the radio.

“Flynt! So good to be hearing your voice....tell me. Have our scouts reported anything?” Anna replied.

“Nothing of interest.” The man said in a bored tone. “Only tourists and more tourists. Those ponies don’t send out many cargo ships out nowadays.”

“Ah! Tourists are an excellent source of income my friend, you should try raiding a nice juicy cruise ship once in awhile.” Anna replied

“I have once, they crew tasted awful.” Flynt said smacking his lips in disgust, Anna pinched the bridge of her nose and sighed.

“Well this time we won’t eat them, lets see if we can get one of those Canterlot Cruise ships. They always have good loot.”

“Fine! We will-... What do you want?” Flynt’s voice became muffled as he began to converse with a crewmember. “Really?... Luxury you say? HAHA! Anna we have struck a vein of luck! There is one of those ‘Big fat cat’ cruise liners!”

“Wonderful! Well then lets get to it! What's our new course?” Anna asked, a smile creeping onto her face.

“Due North-east! Just follow the Quick Draw!” Flynt said before he hung up.

“Very well! X.O.! Follow the Quick Draw, the Iron Keep is getting ready for a bit of a hunting expedition. I want our guns at full ready, but do not fire anything more than a warning shot unless you get the order directly from me.” Anna said with a devilish grin, the XO related the orders to the crew who cheered. “Now raise the Equestrian flag, let them think we are their allies.”

~^~

Twilight and her friends were enjoying the afternoon, soaking in sun on the deck of the airship cruiseliner. It was a beautiful ship, elaborately decorated, everypony was enjoying themselves . Rarity and Fluttershy were happily getting their hooves done in the spa near the front of the ship. Applejack was relaxing on the stern of the ship, rainbow dash was in a deck chair reading Daring Do while Twilight sat next to the pool reading a short book titled ‘Alicorns and You’. Pinkie was nowhere to be seen which wasn’t unusual. Princess Celestia had ordered the girls to take a vacation, after all they had done they deserved it. Fluttershy was now on the deck next to Rarity staring out into the sky with her wing over her partner. Her attention was drawn to a Sky Arrow class ship coming out of the clouds followed by what looked like a human Brimstone class Destroyer. Both were flying the proud Equestrian flag.

“Look darling, all of those brave mares and colts serving in the Navy. I truly wonder what they seek.” Rarity commented.

“Y-Yeah.” Fluttershy

“Attention! Crew of the E.C.S Equestrian Dream! We require to board your vessel in search of a criminal!” The Sky Arrow shouted over an intercom.

“DA! WE ARE WISHING TO ASSIST IN HELPING SEARCH!” A Russian Accented voice called out from the Brimstone ship.

“This is strange, usually they notify us over the radios.” The Captain said as he gazed out at the ships. “But if a criminal is possibly aboard, we probably shouldn’t take chances. Let them board.” The ship lazily come up the side of the ship before the doors opened and several humans covered in leather and bearing arms laughed as they swarmed the ship. “Oh come on! Pirates? On the second day out? I am so fired...”

“Hello Fillies and Gentlecolts...” A tall female said in a russian accent.

“This! Is a robbery! No pony moves, no pony gets shot.” A man said with an eye patch covering his left eye and a six barreled pistol in his left hand while a sword was cradled in the other.

“Oh this is too easy, Flynt, you take starboard and I will take port, Split down center yes?” The Woman asked

“As long as we get loot, who am I to question, Anna?” Flynt said

“Wait! You and you! You can’t do this! DO YOU KNOW WHO I AM!” A blonde unicorn said indignantly.,

“.... A pony missing his left leg.” Flynt said as he raised the pistol and aimed it at the pony.

“Such a shame.” Anna said sadistically as she aimed her Tokarev at his hind leg.

“On Three, Anna?” Flynt said smiling.

“Three.” With that Anna squeezed the trigger and a round lodged itself into the unicorn’s leg nearly tearing it off while Flynt shot into his right fore leg, letting the pony drop to the ground in shock and pain.

“Never question a cielo.” Flynt said as he walked and stepped over the pony.

“Now! items of value, gold, silver, jewlery...all things like that in the bags.” Anna said as her crew began to fill their bags with loot. Fluttershy and Rarity stayed absolutely still not wanting to draw attention to each other, the human by the name of ‘Anna’ “Comrade Utchanko!”

“Yes Captain!” A pirate sailor asked.

“Go to the galley with some men and gather the food so Flynt doesn’t eat any ponies.” Anna said in a whisper.

“Aye aye captain.” Utchanko left without a word.

“Hey Anna! You will never believe what I found!” Flynt said as he walked back with a gun pointed at Twilight’s head. “A Alicorn!”

“Ah! The rare princess Twilight, where are her guards?” Anna said with a bow.

“Uuuuh.” Flynt said looking around the ship.

“Flynt, did you eat them?” Anna asked, Fluttershy and Rarity shot nervous glances at Twilight. Flynt had his hand clamped firmly around her horn preventing her from casting magic.

“No no... Dead yes. But no I did not eat them.” Flynt said shrugging. “Some attack, I killed. Others? I tied up! I am a cielo! Not a monster!”

“Okay whatever, what are we doing with her?” Anna asked, Twilight was shaking like a leaf and with tears in her eyes.

“Hmmmm....” Flynt said as he looked down at Twilight. “I say, knock her out, take the loot, and leave. No reason to make too much bloodshed.”

“Agreed....” Anna said, Utchanko returned with a sack of vegetables and fruits over his shoulder as well as a white rabbit in his hands. “You found a rabbit?”

“Da Captain, he was in one of the cabins we raided. Can we keep him?” Utchanko asked, Fluttershy recognised the rabbit as her own friend Angel. She stepped forwards which led to Rarity attempting to stop her but rather than do that she pushed her farther forward.

“Ah looks like we have found its owner.” Anna said with a smile. “Take him to my cabin, give him some carrots and lettuce.” Anna said before turning to her crew. “Now! BACK TO THE SHIP COMRADES!” The sailors replied with a loud ‘URA’ before climbing back to their airship

“Forgive me, Princess.” Flynt said before lifting the pistol before striking the back of her head and letting her fall to the ground unconscious. He walked over to the boarding plank of his ship as everyone of his crew jumped on. He turned and waved goodbye with a smile. “Thank you for your cooperation!”

“DOS FADANIA! HAVE PLEASANT TRIP!” Anna shouted, Fluttershy was livid. Her wings opened wide and she took off after the Brimstone Class destroyer. She landed on the stern and looked back at Rarity who was crying loudly, all of her friends were watching as she was carried away but she had to save angel.

~^~

“Captain Anastasia! We are going to be landing in the plains outside the border! Do you copy?” A voice crackled over the radio. “We apparently have unwanted stowaways and it is taking all of our crew to keep Flynt from tossing the poor mare off the side of the ship!”

“Ah yes, we too have an unwanted guest.” Anna said as she dodged a carrot hurled at her head. “Fucking rabbit! I would have you turned to stew if I weren’t against meat.” Anna shouted as she hurled a carrot back at the offending rabbit. “Alright, send your coordinates to the Helmsman.” said Anna from her private quarters.

“Yes, Captain Anastasia!” The crew man said before going off the air.

“Now will you stop! I’m trying to feed you god damn it!” Anna shouted at the rabbit before grabbing a carrot and holding it offensively. Fluttershy watched in fear as she saw the human start to charge at Angel who desperately tried to dodged but ended up getting grabbed. “Now you eat the fuckin’ carrot you little rodent!”

“Stop it!” Fluttershy shouted louder than she wanted, the woman turned and looked at the window where she saw the yellow mare. “I mean...if thats alright...” Anna dropped the rabbit and walked towards the mare who was now cowering behind her mane. She squeaked as the barrel of a Torkarev was soon in her face. “Oh...my...”

~^~

“JUST LET ME THROW HER OFF! LET THE SKY SHARKS HAVE HER!” Flynt yelled in rage as his entire crew was holding him back from getting to the pink stowaway, whom was pressed into a corner of the ship.

“There are no sky sharks Cap’n!” A sailor shouted

“I will make them! I’ll get shark semen and eagle egg and breed them!” Flynt growled out as he thrashed around in his crew’s grip. “And I’ll keep one as a pet for just such an occasion as this!”

“Jesus Cap’n...” A crew man said looking at Flynt with a disgust and terrified expression. This continued on until a crew man walked over to the pink pony and lead her away from the crazed captain, who was still being held back by the crew.

“You shouldn’t have gotten on this ship, lassy.” The man said as he lead the pink pony down into the ship.

“I was just trying to go save my friend!” The pink pony huffed before she was taken and pushed into a cell. As the iron bars closed she turned and looked at the man whom had a sympathetic face.

“This is for your protection lassy. The Cap’n isn’t too please right now.” The man said as he locked the gate into place.

“Aye, he normally eats the blokes who get on ‘is ship without ‘im knowin.” Another man said, he was sitting at the table with a bottle of applejack daniels in his hand.

“Plus, he wasn’t kidding about the shark thing. He will do that.” The man said as he began to walk away.

“See a later shamus.” The man with the bottle said before taking a large gulp of the liquid and slamming the bottle down on the table. “Ah that be the stuff.”

~^~

Celestia was livid, Luna even more so. Twilight had never seen so much rage on the face of her mentor, not even the time she turned Philomena into a cactus.

“WE HATH NEVER SEEN SUCH INSOLENCE FROM HUMAN PIRATING SCUM IN ALL OF OUR YEARS!” Celestia roared, she was so angry she was using the ‘royal we’ as well as the ‘royal canterlot voice’. “THAT THEY HATH TAKEN TWO OF OUR MOST VALUED PONIES! IT SICKENS US TO THINK WHAT HORRORS THEY ARE FACING!”

“This is most certainly a new low for the pirates. Raiding civilian ships is one thing, but to actually foalnap somepony!” Luna seethed angrily.

“RRRRAAAAAH! I just want to strangle those pirates sometimes!” Celestia said slightly less loud but no less angry.

“Princess, didn’t you hear me tell you? Fluttershy flew after the ship when it took angel...” Twilight tried to interject, her words fell on deaf ears.

“We will have shining armor find these pirating scum at once!” Celestia shouted.

“Princess, Um... We... Can’t.” Shining said nervously as he looked at Celestia.

“WHY NOT!” Celestia, Luna and Twilight shouted at once, Shining shrunk a bit.

“Well... They are out of Equestrian borders and we are not allowed to pursue them without the permission of their governments.” He said shifting in his armor.

“Then get it!” Celestia said with a humph. “Ugh, get me the phone to the Russian and American leaders, maybe they can help us.” A phone was bought out by one of the servants and celestia picked up the receiver. She dialed the number for the American foreign affairs office and after an hour of yelling and hollering she came up empty hoofed. No way the Americans or the Russians would help her.

“Maybe... the yelling wasn’t the best approach, Princess.” Shining armor said wincing slightly at the loud groan that escaped the Princesses’ lips. “What if we just set up like a... Lure or something?”

“And risk more ponies lives?” Celestia inquired.

“Well generally, they don’t kill the passengers unless they attack them first. Aside from the one case of a pony getting eaten, but that was long ago.” Shining said.

“Set it up, give them a piece of bait they could never pass up.” Celestia sighed.

“Princess, I tried to tell you before, they didn’t take Fluttershy or Pinkie Pie by force.” Twilight said very nervously.

“That doesn’t change the fact that they are pirates. And they shot Blueblood in cold!... Blood! He won’t be able to walk properly ever again!” Luna said.

“Well to be honest...he kinda brought it on himself.” Twilight mentioned, it went unheard.

~^~

“Do you know where I can find a eagle egg?” Flynt asked the pony behind the counter. “And some Shark semen?”

“Out.” The mare said before pointing a hoof at the door.

“No no, I am being serious!” Flynt said waving his hands in front of him. “I need to find that stuff.”

“OUT!” The mare shouted.

“Do you at least know where I could find the egg?” Flynt asked.

“NO! OUT!” The Mare shouted even louder.

“Okay! Jeez!” Flynt said walking out of the store and walking over to Anna. “She didn’t have it.”

“No? Really thats such a shock...” Anna deadpanned.

“I know! I thought the ponies had everything!” He said oblivious to her sarcasm. “Guess I’ll just have to go find a shark...”

“Maybe later, we have more pressing matters to attend to.” Anna said plainly before gesturing towards her ship where both the stowaways had been taken.

“More pressing than a flying shark as a pet!?” Flynt shouted throwing his arms in the air.

“Much.” Anna said plainly, just like the mare in the store. “We have a very large problem, from what I can tell we have two of the six element bearers on our ships.”

“Oh those ponies? I thought they looked familiar. I still want my bird shark.” Flynt said as he followed Anna to the ship. The woman pinched the bridge of her nose and sighed as they walked up the gangway.

“Now what do we do with them? We can’t just take them back and say ‘Here ya go! Sorry for plundering your airships!’.” Anna moaned. “Maybe we should drop them off at the border and just leave ‘em there. I’m sure they’ll find a way home.”

“Well... There is always option ‘B’.” He said pulling out his pistol.

“No.” Anna moaned again.

“Fine... I am still ticked at the pink one though, so keep her away from my ship. I don’t care what happens to them otherwise.” Flynt said holstering his pistol.

“Maybe we can arrange a formal parlay with the Equestrian’s just to get rid of them and improve our standing with them.”

“.... You want us, Pirates. To go to Equestrian government? Yea, even I can see the flaws of this plan.” Flynt said giving her a deadpanned stare.

“Well we can’t keep them forever! I say we take off, find another ship and dump them there.” Anna said angrilly.

“Why don’t we jus-”

“NO! SKY SHARKS!”

“.... Fine. We will do your plan.” Flynt said pouting.

“Alright, lets take a few days to rest up. This could be a very long trip.”