Pipsqueak: The most gentlecoltly anarchist pirate ever

(A/N: A combination of writer's block and depression hit me hard. Sorry 'bout the massive chapter lag.)

Pipsqueak stood at the helm of his ship, long since ridding himself of his disguises, he sailed now with is decorated, albeit odd hat.

"Oy! Cap'n! It's the dead of night! Why're up here?" Scootaloo peaked her head from a hatch leading below into the ship's underbelly.

A cloud passed by and the night wind gently whispered in his ear. It had been a warm summer day, and it was a warm night.

Instead of talking, or turning around for that matter, Pipsqueak motioned for her to join him at the head. Behind his back, Scootaloo shrugged, sometimes the Captain had his moods, this must have been one of them.

"What'cha need?" She asked casually with an air of questioning. Pipsqueak didn't answer her, he was staring straight up, his Adam's Apple visible as it stretched over his voice box.

"Scootaloo, tell me. Have you ever looked up to the sky and thought you were little?" He asked. Scootaloo cocked her eyebrows in clear confusion.

"....No?" She answered, truthfully Scootaloo never thought of anything before-hoof or after. She was, as affectionately dubbed by the crew: A monstrous 500 pound rape train in disguise of a mare.

And while Scootaloo herself was quite nice and docile in nature, there was no rock big enough to hide under when she got pissed. Pipsqueak had seen first hoof the herculean strength the mare carried in her sleek physique.

"That's quite alright ol' girl. You can go back now." He said with a sigh. Scootaloo merely shrugged and headed back below decks.

Pipsqueak however, stayed out on the prow of the ship smiling as the wind swept his hair, the only sound coming from the various propellers used to steer the ship.

For you see, the Foalhood dream was no ordinary ship. None like it was ever built or ever conceived. It was inconceivable.

He reached out a hoof as a passing cloud passed through the ship. Pipsqueak sighed in contentment as he watched the cold bubble of moisture, and he leaned back, closing his eyes and entering dreamland amidst a sea of clouds.

==========================

"Have you seen this colt?"

"No, can't say I have ma'am."

Luna inhaled deeply, a growing sense of frustration knotting in her belly and threatening to send her mind into a whirlwind. She had set off in the middle of the night to find him, and despite various reports of a certain Colt wearing a certain Hat floating in through the Canterlotian Police force, there had yet to be a proper sighting. All that she had to go on were a group of very pissed ponies all claiming to have seen a capped caper tearing through their middle of the night romps/errands/routines.

Currently she was sitting in the middle of the prestigious Canterlotian Police Headquarters.

"I swear to the high n' mighty Billy the Colt is the all time best western!

"And I swear on my dead grandma's grave, bless her soul, that Two Buck Timmy was the best!" She felt parts of her brain die as the two cops-IMBECILES assigned to her debated who was the best criminal just outside of the detention center.

Her mane was a mess, there were bags under her eyes, and like a freight train from outer space, she realized that she still had 3 press conferences with around several different prime ministers and heads of VERY important 1st world allies all in the morning.

So, she did what any mare under this type of pressure would do.

She went to the bathroom and shrieked like a banshee.

"HOY! CAPTAIN!" The rather crass voice of his first mate awoke Pipsqueak, grumbling from his deliciously mad dream about Luna saucily eating a banana.

"WHAT?" He shouted, grabbing his hat and making his way to the helm.

The crew was gathered around the brow of the shit, surrounding them was a monstrous Highland Air Drah. Or a cloud serpent for short.

It was currently staring curiously at the crew, unsure what to make of the motley band of misfits staring back.

Pipsqueak stood stock still at the door to the Captain's quarters.

For an eternity, nobody said a thing.

"WHAT FUCK. IS THIS?!?"

Shouted the captain.

And all hell broke loose.

===========

Sir Arioland the 5th of House Ravensfriend stared at the skies, unease wrought on his face as he grimaced and squinted.

"Any sign of them sir?" One of his serfs asked, the young lad was barely older than a chick when he'd signed on. Sir Ario had found quickly however, that he was more useful than the twenty something of his counter-parts who usually ran around like headless chickens any time their superior did a ROUTINE inspection.

And keep in mind, this was routine, Ario had to shudder and repress the memories of the recruits in their...alone times.

"Not yet young one. Oh for the high king's sake where are they?" He called. The griffon held a pair of binoculars to his eyes as he scanned the sky for the telltale pirates he'd been informed about. News had spread quickly throughout the kingdom of the crashing of the Grand Galloping Galla. And of the subsequent chaos.

The King's Faberge Jubilee was commencing in not 5 days time and he was in charge of security. And as a griffon of his word, he would not let the king, nor his kinsman down.

The elder knight wore heavy chainmail with high arching shoulder plates made of the finest forged steel from the High Hammer's Forge. The best Blacksmith in the Griffonic kingdom. covering his back and underside was plated heavy iron. Each platelet overlapping it's kin to make a nigh impenetrable wall of unstoppable metal.

Slung on his back was the Bane Bringer, a sword crafted from the very essence of Windigo's souls. Tamped with ectoplasm from the souls of the great and blessed by the holy water from the church of His High majesty.

He was a force to be reckoned with, and as a veteran of many, many wars. He was a nearly unstoppable killing machine when rubbed the wrong way.

Currently however, he was staring in unconcealed awe.

"AND I'LL RIP YER VERY EYES FROM THEIR SOCKETS AND FEAST ON YER HELL DAMNED BALLS YA BIG BLOODY SORRY EXCUSE FOR A MONSTER! YOU'LL BE FEARIN' THE DAY YA MEET ME YOU BIG UGLY GROTESQUERY! I'VE SEEN HALF-DRUNK CHICKENS WITH MORE CAJONES THAN YOU!"

There was the aforementioned fugitive and ruffian, scourge of the law.

Bareback riding a monstrous Sky Serpent who's roar shook the very sky and scattered the clouds. End to end, it could stretch from High Claw, the gryphon's capital to Feather'sDale some 50 odd miles away.

In all his years, Sir Ario had only ever heard of knight who took on a Sky serpent and lived to tell the tale.

His name had been Sir Havensclaw of House Immolation. He had been a walking tank in life, or so the legends had said, and Sir Ario had seen a portrait depicting the knight covered in all black bravely slashing at a monstrous Ursa Majora.

He had been the best knight in the kingdom, with armor forged from the wrought souls of fallen beasts of evil, his armor: Mavack was on display in the Museum of the Round Table. It was midnight black and glistened with runes so powerful that one had to watch how long he or she stared or else their very soul would be sucked in.

Yet here was a fugitive of the law with shoddy clothing. No armor and very little protection against the freezing wind of a thousand miles straight up in the air.

From what Sir Ario could see, he only wore a hat that seemed to be frayed with age and an aviator's jacket with many holes and tears and a vest underneath it.

And the only thing he was using, was a claymore sword.

The massive Sky Beast swooped down low over the garrison and Sir Ario ducked, forcing the fear stricken serf down along with him.

"AND I'LL CUT UP YER DAMN FACE INTO GUACAMOLE DO YA HERE ME?!?" The belligerent pony shouted, hanging on for dear life as the massive dragon/snake hybrid squirmed and twisted, it's tail smashing into the earth and up-ending villages. Truly the sky beast was a behemoth on all accounts.

Once it had safely passed, Ario stood and flared his wings, ready for flight.

"Squire! You will go to the barracks and call forth reinforcements! Once done, race to the king's castle and alert the rest of the Round Table Knights!" He shouted. The young one shook his head.

"But what about you sir?" He asked shakily.

Sir Ario drew the Bane Bringer, faintly did he hear a war bellow as he held it straight up with his front claws. Already shooting into the air.

"I shall stall the fowl beast!" He shouted.

==============

Pipsqueak clung to dear life as the massive beast swung too and fro, trying to shake him off. One hoof was entangled within the mane of the chimera and one held the Claymore.

Through gritted teeth, Pipsqueak shoved the sword not unlike a stake into the serpent's neck, using it as a base. As he untangled his trapped hoof.

"HALT YE ABOMINATION!" Pipsqueak lunged forward, barely holding onto the massive serpent via. his sword.

Climbing up to the thing's head, he stared at the single gryphon who blocked the monster's path.

"Turn back from whence you came and I will spare your life!" He shouted. His sword drawn horizontally to his left. From what he could see, Pipsqueak observed that it was a rather large broadsword. He also noted it glistened light ozone as the surface seemed to shiver.

The beast was silent a moment.

"ARE YOU OUT OF YOUR BLOODY MIND?! DO YOU NOT SEE THE BLOODY SIZE OF THIS?" PIpsqueak yelled.

"You there! Disband from the monster! You are under arrest for the disorderly actions you have wrought upon the ponies of-"

Knight Arioland the 5th of House Ravensfriend never got to finish that sentence as the serpent took a very deep breath, a small jetstream pulling at he knight's body as the wind rushed by him.

And with a roar that would deafen a god or a giant, it blasted a massive wall of sound at the knight, instantly blasting him with Gale force winds.

As he fell, Pipsqueak felt something snap inside of himself.

"I'd say this has gone on long enough." He stated quietly as he pulled the Claymore above his head. The serpent stopped and cooed as it watched the knight fall.

It did not however, see the dark aura and wind rushing by Pipsqueak and into the sword.

"Oh you'll curse tha' day ye met Pipsqueak. Captain of The Foalhood Dream."

The sword began changing. It got longer, and the metal changed from glistening gray steel to sanguine red. It seemed to ripple with power.

It was at this point that the Foalhood Dream popped through the cloud layer, First Mate Scootaloo at the helm.

Her expression of extreme concentration evaporated, soon replaced by one of sheer horror as she saw the massive black funnel cloud above the serpent.

"What in the name of the good meadowmaster is that?" Asked one of the crewmembers,a curly afro'd black unicorn who wore a revrend's collar.

Instead of responding conventionally, she shouted: "ALL OF YOU! UNLESS YA WANNA SEE WHAT THE TRUE MEANING OF FEAR IS, GET DOWN!"

And as everybody hit the deck, Pipsqueak let loose.

Gently, almost lovingly did he bring the sword down from it's elevated position until the hilt was level with his face. The sword had changed, no longer was it a claymore. It had become a claidheamh mòr. And no normal one at that.

The hilt had completely changed, it had expanded and was shaped like a curved shuriken, the metal had changed, it glistened blood red and seemed to call, its voice resounding in Pipsqueak's head.

But what stood out most of all, was the small stone sitting in the hilt.

Sighing with resignation, he placed it back in his hat.

And with that, the hat began to glow menacingly red.

His mind was slipping as he reached back inside, the voices told him it was ready.

"Oh, you'll rue the day you met me." He whispered, pulling out the new weapon.

It was the same claidheamh mòr. Only this time it resonated, and seemed to be moving on it's own.

"Your bones will shake and your will tremble as I cast the black blade from whence it rests. Look upon your last day and cry, for none shall escape the Dreadmora." He chanted.

And with that last sentiment, he plunged the blade into the neck of the beast.

It screamed in untold agony, almost drawing pity from Pipsqueak.

It's whole body seemed to spasm violently for a second before freezing. It's veins started glowing purple. Soon, the purple light spread through its whole body, and eventually to its eyes as the captain closed his.

"Rest in pieces."

Without another word he pulled the sword out.

And the snake's carcass exploded.

=======

"Sir Ario! Sir Ario!" Screaming and shoving awoke him from his dreamless slumber as the great knight came too.

"Ugh, what happened?" Rubbing his head and squinting due to the bleariness, he barely saw the outline of a gryphon sigh with relief.

"Oh! Thank the lords you're okay!"

"Oh, the serf." He vaguely registered, accepting the young's one help in lifting himself off the ground.

"Ooooh. How hard did I land?" He asked.

The serf remained quiet.

Blinking the crust and sand from his eyes, he opened them once more.

Surrounding him was a large crater, most probably caused by his crash landing.

But at the moment, that was the least impressive thing facing him.

Sitting in front of him, was the head of the utterly massive Sky Serpent, alone, the head was a small mountain.

But sitting at the top of that mountain, was a single colt, his hooves wrapped around a red blade that seemed to shine and send out a little electrical spark every once in a while.

He sat motionless, caramel and chestnut mane drooping and covering his face and eyes.

Atop his head, tilted at an angle was a hat that seemed innocent, yet the more he stared, the more Arioland couldn't help but feel disturbed.

"What happened?" He asked, standing in awe.

"...You."

Arioland turned to the serf, Pipsqueak raised his head.

The serf was pale, quaking in his over-sized armor. His eyes were as wide as saucers. Arioland was surprised, the boy hadn't been this scared, not even during the siege by the monstrosity.

"I...I-I remember you!" The colt began shivering.

Pipsqueak merely smiled.

"No kiddo, you remember the sword."

"Y..Y-y-you were a monster on the battlefield! You killed so many!"

Ario raised an eyebrow.

"Who is he young one?"

The serf broke down in tears.

"THE MAD ONE! HE'S THE MAD ONE! THAT SWORD IS THE DREADMORA!"

A cold knot formed in Ario's gut as he turned back to Pipsqueak.

"I never thought I'd have to use it again. The Dreadmora."

Ario felt himself slipping as he went back to the 'dark days'.

The farmland and city scape was replaced by a blood soaked battlefield under a moonlit night.

And sitting on a pile of dead bodies was the same stallion.

With the same sword.

With the same grin.

(A/N: It's back! And better than ever!)