• Published 21st Nov 2016
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Bleak Sails - RedRandom



The Mane Six must team-up with a crew of deadly pirates to stop a mad skeleton from flooding Equestria with an ancient artifact from long ago.

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Chapter Three: A Sparring Match

The water flew underneath the Bronze Millennium softly as the crew went about their duties. It had been a week since Twilight and her friends had even seen, felt, or had breathed in anything other than salty sea air.

It hadn’t been all bad though, during that week they had been trained how to properly handle and maintain the ship thanks to Moll and Booksalot. Luna’s night was young and calm, the lamp lights still needing to be lit. As Twilight was trotting past one of the many freshly lit lamps she took a moment to look up into the night sky and admire the work of the Princess.

Though, as she looked upon the stars in the sky, the look in her eyes seemed to show that she was troubled with something. She didn’t know why but she was nervous about this trip, something just tugging at the back of her mind about the danger of the journey, especially since she had little to no knowledge on who they were facing.

She knew about Nightmare Moon, she knew her story and past and had an explanation for her. She knew about the legends and facts of the Discordian Era of rule, she could call off the exact number of years that it had been when Discord was in charge. She had studied changeling biology in school, hell, one of her teachers was a changeling, so she understood why Chrysalis would be inclined to attack and attempt a military takeover.

The only ones that had put her in a position like she was now were Sombra and Tirek. She hadn’t known of the Crystal Empire or it’s dark history with the umbrum unicorn. She didn’t know of the magic stealing centaur, nor of his desire to take over the land. But, the differnce was that she was given information before she went on those missions.

This one, however, was different. She barely had a clue on who these two pirates were. The only thing about Jolly Roger that she could find was the old urban legend about how if a young foal goes to deeper waters alone, the skeleton would drag them to tartarus. But, other than that, nothing of importance came to her.

Franz was a little bit easier to get information on, or, at least information that she wasn’t entirely sure the accuracy of. She looked down towards the shifting tides of the sea for a few minutes before sitting down, returning her gaze to the sky above.

“Bit for your thoughts?” Booksalot asked calmly, walking up towards her before he sat down on the deck next to her and joined her, joining in watching the night sky.

She looked beside her, raising an eyebrow in confusion. “What do you mean Booksalot?” she asked, tilting her head.

“I can tell that you have something on your mind.” Booksalot replied kindly as a smile came to his face, “It has something to do with not knowing much about Jolly Roger, isn’t it?”

Twilight stared back in surprise by the correct answer that Booksalot gave her.” How did you know?”.

The older stallion gave a shrug and says “I know more than that. For example I know you grew up in Canterlot within the Sparkle household. You had a doll named Smartie Pants, that has recently gone missing to you but I’ll tell you right now the farmer’s brother still has him. You had a magical surge at a young age giving you a cutie mark and hatching the young drake aboard the ship. And you broke three ribs and your snout during your fight with Tirek a year ago yet never realized it until after you returned the excess Alicorn magic within your system.” Booksalot stated without skipping a beat, “I can tell most of that from just various scars that only the trained eye would notice as well as the fact that I’ve worn the face you are wearing right now and just moments before I sat down many times myself.”

Twilight’s surprised face became that of confusion at the stallion who had just summed up her life in a few quick sentences.

Booksalot looked over at Twilight smiling with amusement at her confusion before asking “So where would you like me to start? I may not be as old as Granny Smith but I do know a thing or three.”

Twilight thought long and hard about what he meant by that before finally coming up with an answer. ”Who was Jolly Roger?” she asked as the stallion turned his gaze back to the starry canvas in the sky.

“Jolly Roger was in simple terms a stallion with a heart of black.” Booksalot began, “Jolly was a Pirate, Murderer, Betrayer, Father, and Husband. His life started out simply as most ponies lives do. He was born the day after Princess Luna became Nightmare Moon and was banished to the moon.” Booksalot then looked over and focused his gaze upon the moon.

“Because Celestia originally didn’t know how to have the moon listen to her as Luna did it was sent slightly off course. This forced the oceans to rise and flood the land. Using the Elements Celestia was able to keep her little ponies safe during this time of turmoil. At the age of twenty Jolly became a Captain within the Royal Navy for Equestria. He also had recently married and she gave birth to a wonderful daughter. “The most beautiful mare I have ever known has given me something for us to cherish with our lives and that nothing could ever replace.” I believe were the exact words of Jolly’s about that time of his life.” Booksat added with a chuckle near the end.

“I am of course translating that into modern Equish for you to understand dear Twilight.” Booksalot then looked out toward the horizon, “Now where was I… Ah that’s right, Jolly’s daughter had just been born and was nearing a year old when she fell fatally ill, Being desperate for money, Jolly soon performed the very first act of piracy in order to get the money for his daughter. But, like most things, he became addicted to it. He was only supposed to only take one ship and go straight back, but he continued on into the night. This greed took the life of his daughter, who died in her sleep.”

“That’s awful…” Twilight noted, looking down to the ground as she attempted to imagine what pain both Jolly and the wife would have had to feel.

“Jolly, having fallen too far into his greed, was dishonorably discharged by Celestia herself for his actions, causing him to perform his acts of piracy more openly. This resulted in his wife leaving him, driving him deeper into insanity. But, his growing popularity gained way to him being crowned King among his ever growing fleets of down on the luck sailors due to his powerful Aquamancy and also for him inventing the act.”

Twilight stared at the stallion with a bit more understanding in her eyes. But there was still something that confused her. ”How do you know that much about him if most of the copies were destroyed?” she asked with the stallion chuckling again being part of her answer.

“Old journals of not only his and Celestia, but also the one of his wife, ” Booksalot said with a shrug. “My Library has old enchantments upon it to have at least one copy of every book ever written. Anyways, Jolly soon found a way to become immortal and was going to share it with his crew. An artifact called the Trident, said to be created by the Spirit of the sea, Davy Jones...I am rambling again, aren’t I? When he first got his hooves on it, the Equestrian Navy had followed him with his wife, who had since married the captain of the vessel. But, she was killed in the ensuing fight. Jolly took the Trident and lead a direct assault upon Canterlot which ended at the end of a long combat with Celestia locking him within his flag using the Elements.”

As this new information reached Twilight’s ears and embedded itself deep into her brain, the sudden voice of Rainbow Dash dragged the two ponies’ attention towards the crowsnest. Rainbow had been sitting there for at least five hours, being ordered to command that section of the ship and to keep an eye for the little scalawag they were hunting.

“Ship! There’s another ship to the west!” she screamed from her position on the tall main mast. Her Pirate lingo not being that great as she signaled for the rest of the crew to meet on the deck.

As the rest of the crew made it to the deck, Moll stepped forward and took out a telescope, putting it gently near her left eye to see what Rainbow shouted for.

Floating in the salty waters of the sea just 500 metres away, sat the silhouette of a large ship. Four masts could be seen on the ship and by the looks of it, the ship appeared to be a heavily modified slave vessel. Moll gave out a smug grin as she put her telescope away as she turned to the rest of crew. She knew exactly whose ship it was, she knew exactly who captained that particular vessel and she also remembered exactly why her distaste for the Captain had arisen before Pinkie Pie spoke up.

“Who is it?” She asked with her normal cheerful tone of voice, bouncing up and down in place as Moll put the brass telescope into a pocket.

“That my friend, be the ship captained by the very griffon we are looking for,” she answered, silence falling upon the group before Sellick gave out a hearty laugh.

“Well, what are we waiting for!” Rainbow shouted as she descended from the crowsnest. ”Let’s kick their butts and get the Elements back!”

“Do you really think that it is wise to charge directly at a ship of professional Pirates when you all haven’t even finished learning the basics?” Booksalot asks Rainbow Dash sternly

“Booksy is right Lasses, for now we shall sail onward toward Clustered Isle so that ye lot pox mussled, grog snarfing, mild maids.” Moll says as she continues to laugh, “And please don’t take any of my insults toward you lot seriously I just need to practice.”

“Why?” Rarity asked with a smirk raising on Moll’s lips being part of her answer.

“That’s a part of fighting as a Pirate. You have to be able to throw around as many pirate curses as you can.” Moll Stellick says as she heads to the helm and starts to steer the ship away from the Maremaid.

Booksalot then let out a chuckle as he watched Moll before saying “I know you’re actually turning us away because you don’t want me to get hurt protecting all of you.”

“Oh har har, like some old guy like you could even hurt a feeble stallion!” Akula commented with a cheeky smile. Before he could continue the joke, his mouth was closed by Moll’s hoof, a stern look on her face.

“Shush boyo, we gotta be quiet or else they’ll hear us and believe me that some of them have good hearing,” she warned, getting shocked faces from the others as she quietly steered the Millennium to the right, away from the silhouette of the Maremaid.


As the Bronze Millennium drifted through the waves, Akula training Twilight and the rest almost brutally on how to fight with a sword. The way he had before been jokingly insulting the unicorn yesterday to becoming the most strict of training officers they had ever seen.

Fluttershy seemed to be having difficulty with the sword that she was given, almost as if she weren’t even trying to strike at Akula, who had assigned himself to be her sparring partner.

“Are you having difficulties, Miss?” he asked with a concerned tone of voice as he lowered his cutlass. “Would you prefer a lighter sword?”

The shy pegasus simply stared towards the battle hardened soldier that stood before her with worried eyes. ”I would prefer if I didn’t have a weapon, Mr. Akula,” she calmly stated, the stallion’s eyes widening a bit before his expression became detached, his voice almost emotionless.

“And, why would that be Miss Fluttershy?” he questioned, sheathing his cutlass in his scabbard as he stepped to her, his build dwarfing her and slightly intimidating her as she opened her mouth to respond.

“Because she’s the Element of Kindness. Fluttershy has always helped other no matter what and hates bringing them harm.” Booksalot started, speaking up from near the bow. As he slowly turned around “Your teaching methods are best suited for some but definitely not Miss Fluttershy.” Booksalot then trotted over to Akula and poked him in the chest with a hoof. “If I remember correctly you asked me last night how I could protect you all. How about I give you a demonstration of how, personally.”

Moll looked on from near the helm slightly interested in the outcome of the argument. She noticed how Akula almost looked insulted, his eyes becoming narrow and cold, nodding as he chewed on nothing from her position at the helm of her vessel.

“If you wish Mr Booksalot, it might do these mares some good,” he agreed, holding his cutlass and releasing it from the confines of his scabbard. ”If you will sir, please stand at least five feet away. That should be enough space for a fair match of sparring.”

Booksalot stood where Akula requested and nodded simply to himself, “I’m assuming that the rules will be of the classic Naval Dueling System?” he asked as his horn lit ruby red and a flaming cutlass appearing next to him. “Light touches and winner is declared when the other yields or is dead?”

The gray stallion simply nodded again in response, admiring the sword that was in the unicorn’s magical grasp. ”Of course Mr. Booksalot, we are at sea aren’t we?” he joked, trying to think of a way to get past the older stallion’s advantage of his magic. “Are you ready, sir?”

“No better time like the present.” Booksalot called, giving a wide swing of his cutlass toward Akula to test his defences. Moll then came down from the helm and said “You Lasses will want to be with me back at the helm. And then my Bits are on Booksalot mopping the deck with Akula.”

No sooner had the flaming sword been caught in Akula’s vision he had swiftly blocked the swipe with his own weapon, his brutal red army training coming back to him as he smiled. “I was going to suggest playing rock, paper, scissors to get the first blow but if you insist,” he hollered as he thrusted his sword towards the unicorn’s left shoulder.

Booksalot easily parried the blow twisting both of their blades in a full circle before his forced Akula’s to the side his went toward Akula’s right hoof. “That game is for the newer rulings in competitive settings. I meant the original rules from when Jolly Rodger was originally alive.”

Akula jumped back a bit to avoid having his hoof struck, still smiling at the thought of this unicorn being a challenge. “My apologies, but if you will. I doubt that our captain would enjoy us talking each other to death,” he stated before trying his hoof at a combo of swings and strikes, the motion catching the audience off guard.

Booksalot was able to quickly and delicately parry or block every bit of it as a smile grew upon his mussel. “So you’re using the Swashbuckler style, originally founded approximately one thousand nine-hundred fifty-seven years ago by a Naval Commander named Swash Le Mann.” Booksalot then sent a flurry of blows toward Akula, the flame from his blade adding an extra sense of elegance to the swings and the movements of the attack. “But, I know something you don’t know.”

Akula barely managed to dodge or block the strikes, being extra careful to avoid the possible burn the sword would leave. “And what might that be?” he asked, the two circling each other as the rest looked on with shocked expressions, Moll smiling at the spectacle and saying “Once again anypony wanna place bets?”

“Eh, buck it, I’ll put one on Akula,” Rainbow shrugged, causing Moll to smile.

“Just know that I’m throwing two-hundred bits on Booksalot winning,” Moll reminded.

Booksalot’s cutlass then changes into a scimitar as he speaks, “I know the Saddle Arabian Buckler Breaker style which was founded a year after the Swashbuckler by Swash Le Mann’s mortal nemesis Teiner the Wise,” he stated before ducking quickly and swiping at the gray stallion’s hooves. As Akula tried to gain his footing, his armor was grabbed by the magic of the unicorn and with a great thud, the stallion was on his hindquarters, his cutlass too far away to reach for and with the flaming scimitar pointed at the guard’s neck. “Do you yield?”

Akula stared up into the older stallion’s eyes, seeing the lack of anger, hate and other emotions that he would use to be better in battle. With a sigh, he yielded. “You’re better than you look I’ll give you that,” he stated before turning towards Fluttershy, who had come back to the deck after the duel was over.

“But what I was going to say before Miss, you might be the Element of kindness and may not want to hurt these individuals. But they are bloodthirsty murderers and I don’t want to see any of us hurt. I hope you can understand this.”

“I do understand Mr Akula but if you wouldn’t mind, I think it might be better if I just learn some disarming techniques. If you don’t mind of course,” the shy little pegasus responded, the little repeat sounding quite cute to the others.

“Oh and you owe me two hundred bits.” Moll almost laughed, turning to Rainbow Dash with a smug grin at making money. “Booksy won, Akula lost.”

Booksalot then had his constructed blade disperse as he started to limp toward the door that lead below deck.

“So Moll,” Rainbow groaned as she handed over the two hundred bits. ”Are we stopping at someplace near here or what?”

“We be laying anchor in the Clustered Isles. It’s another few days trip and we will be stopping at some of the uninhabited parts first to gather some supplies for free.” Moll Stellick started as she took the bits, counting them as she put them in her hat. “Then we will get to Trotuga and rest in some proper beds before chasing after Franz Le Mann.”

The group went back to their stations as usual, no one noticing that Akula was grumbling to himself. The Bronze Millennium continued it’s way through the salty waters as it drifted into the direction of the Clustered Isles.