The Many Tales of Pipsqueak and the Pirates

by Muleicous

Rating: teen
Tags: Comedy, Pipsqueak, Adventure, Diamond Tiara, Diamond Dogs, My Little Pony: Friendship is Magic
Length: 7123

Pipsqueak becomes a cabin boy for Diamond Dog pirates

Only the most cut throat of creatures land on the Shadow Mare, the ship that Captain Guld of the Diamond Dog pirates runs. However, there is one exception... The cabin boy. A lone boy from a town called Ponyville some how made his way onto the ship one night, and after being found the captain names this colt his personal cabin boy.

Or, at least that's what Pipsqueak imagined. Ever since his first Nightmare Night, he's been fascinated by pirates. But what happens when his imagination gets the better of him?

Published 2012-11-16 12:50:01 UTC
Last updated 2012-11-25 21:05:09 UTC

Ch 1: In which Pip says 'shiver my timbers!'

“Yar! Avast crew, there be the the fleet of Queen Tiara’s navy!” the brave Captain Pipsqueak said as he looked over the bow of his grand galleon, The Golden Gryphon. The colt smiled as he felt the salty wind in his mane and the hot sea splashing upon the planks of his vessel. “First mate Bloom, do ya see any booty on those barges?”

Apple Bloom sighed and pulled out a copy of The Foal Free Press and curled it into a makeshift telescope. She and the other Cutie Mark Crusaders had been playing pirates with Pipsqueak every day this week, and she felt it was getting old really fast. “Aye Captain Pip, there be tons of dublins on them...”

“Doubloons First mate Bloom, not Dublins! What’s a Dublin anyway?” Pip asked, adjusting the bandana on his head.

“Ah don’t know Pip, can we play something else now?” Apple Bloom asked as she slide down the slide, or ‘the plank’ as Pipsqueak called it, “We’ve been takin’ up all the jungle jim for the past three days.”

“I’m with Apple Bloom on this one,” Scootaloo added, Pip had made her the cabin girl on the ship and she never got to see any action. All she did all recess was try and find a juice box for Pip, since that was her ‘duties’ aboard the ‘ship’.

“Recess is almost over anyway,” Sweetie Belle, who was the navigator in Pip’s game, said, “maybe tomorrow we can pick what to play... Is that ok Pip?”

Pipsqueak sighed, then nodded. “Yeah, maybe you girls are right. I mean, playing pirates every day is a little boring...” His Trottingham accent did little to hide his slight sadness over having to stop the game, but the CMC’s were more focused on running back to class. Today was a very interesting subject to the three fillies, Miss Cheerilee was going to tell the school foals about how she got her cutie mark. Soon, the bell rang and all the little fillies and colts were back at their desks, and all eyes were on Cheerilee... Except, of course, Pipsqueak’s.

Pip had his math textbook open and seemed to be working diligently studying the various problems inside, or at least he would if the book on pirates that he borrowed from the Ponyville library wasn’t opened right on top of it. The spotted foal’s eyes lit up as they skimmed the paragraphs on Whitehorn the pirate and his seemingly immortal rivalry with the Equestrian pirate hunter, Capt. Typhoon. Pip could almost taste the salt water that erupted from the holes of Whitehorn’s ship, The Black Beauty, as Typhoon filled it full of cannon fire. He closed his eyes and tried to picture the scene, the two man o wars dueling each other. Pegasi flying from both ships to do battle in the air, while the unicorns on each vessel blasted each other with magic; meanwhile, the two captains would be fighting in the noblest of ways, a horn duel. Both captain locking their magic and horns in a battle to the death, Capt. Typhoon fighting for the pride of Equestria, while Whitehorn battled for the one thing that made him feel like a real stallion... Freedom.

“That’s what I want...” Pipsqueak said out loud, his eyes slightly glossed over.

“Is that so Mr. Pipsqueak?” Cheerilee asked, the laughter of the other students seemed to file behind her voice like the students themselves would do when lining up, “One day you want to be a teacher too? To make young minds bloom?” The mauve mare nodded to her cutie mark, three blossoming flowers, “That is what the class was just talking about.”

“Um...uh...” Pip stammered, his mind going completely blank as he looked around the class. Diamond Tiara and Silver Spoon where laughing the loudest which didn’t surprise him, but what did was that the Cutie Mark Crusaders, his own friends, began to chuckle at him. The poor colt just looked down and frowned, wishing he could hide himself in his book. Soon, Cheerilee gave him the usual speech on paying attention in class and not getting his heads too far up in the clouds, but Pipsqueak couldn’t help but wish he was on the seven seas... Instead of getting his seventh lecture.

X*X*X*X*X

“Hey Captain Pip!” Diamond Tiara yelled as she walked behind the Trottingham foal, “What’s wrong? No ‘aye mateys’? No ‘avast land lubbers’?” the snooty earth pony trotted ahead and stood in Pip’s way, her eyes were even laughing at him now, “Come on, at least say shiver my timbers, you are a pirate after all, right?” The pink filly then burst out laughing in the brown and white earth pony’s face.

“Just leave me alone, Tiara...” Pipsqueak said as he walked around her, “At least I don’t want to be a princess.”

“At least princess’ still exist!” the rich filly said as her laughing subsided, “Pirates went out looooong ago.” Pipsqueak just ignored her, walking along like he had never bumped into her at all. Soon, Silver Spoon caught up to the spoiled earth pony and the two fillies began their walk to Rich Manor, the home of Filthy Rich and his wife Stinking.

“You know, that was a little mean Diamond, even for us.” Silver Spoon told her friend, “Those stories mean a lot to him.”

“Why should I care? It’s not like the little ragamuffin won’t grow out of them, right?” Tiara kept trotting, her eyes catching a glimpse of Apple Bloom and her friends running to Sweet Apple Acres. The farm filly waved at the two richer fillies, but only Silver Spoon waved back. “Really Spoony? You’re still going to be nice to those blank flanks?”

“Apple Bloom’s not that bad Diamond, and I can tolerate Scootaloo and Sweetie Belle. I think you’re just mad at them because they play with Pipsqueak all the time.”

“What?!” Diamond Tiara’s eyes went wide at the thought, “Wh...what do you mean by that?”

“Come on Diamond, it’s obvious. Every time you look over at Pip you blush a little, every time he looks at you there’s something ‘amazingly important’ to look at on the other side of the playground, and lately you’ve been teasing him almost exclusively.”

“You... You think I like that little... Thing?!” the pink filly shook her head, but she couldn’t hide the bits of red that appeared on her cheeks.

“As Apple Bloom’s brother would say ‘eeeeyup’.”

“Yeah... well... You’re right.” Diamond Tiara sighed and looked at her friend, “I guess I can’t keep a secret from you Spoon. But it’s nothing big!”

Silver Spoon cocked her eyebrow at her friend, “We’re in grade school Dia, I know it’s nothing serious.”

“Oh shut up...” the tiara wearing earth pony said, then she and her friend began to giggle.

“Maybe you should do something nice for him.” the grey earth pony said.

“Like what?”

Silver Spoon sighed, “Like apologize.”

X*X*X*X*X

That night, a fog rolled into Ponyville just as its residence began to doze off. However, one little foal remained awake. Little Pipsqueak laid on his bed, reading the book on pirate history by candlelight. Small tears dotted some of the book’s pages, and the sniffles of a small pony could be heard throughout the room.

“I... I just wish,” Pipsqueak said to himself, “I wish that I could be a pirate, that way I could show that jerk Diamond Tiara how... how pirates are real!” Suddenly, the earth began to shake so hard that it knocked Pip out of his bed. The scared foal hid under the covers as the window to his room slammed open, and a ghostly wind killed the candle’s flame.

Soon, heavy footsteps could be heard on the hardwood floor right beside Pipsqueaks bed. The little foal slowly, cautiously, poked his head out from under the covers... Only to find the grey coat of a strange, two-legged creature rummaging through his small wardrobe.

“Hey!” Pip cried as he jumped out of the covers, “Leave my stuff alone! I’ll call the guards!”

The strange creature, its back stilled turned to the little pony, gave a deep, gravelly laugh before speaking. “Well,well... What a brave lad. Your mummy and daddy must be so proud of ya.” The creature turned and showed its face to the little Pip, and what a sight it was. The thing had grey fur from head to toe and stood on two legs while its arms stayed by it’s side, its eye was a deep green (at least the visible one was, for the other was covered by a large, black eye patch), and it wore only two things: a long blue coat with some frilly things on the ends, and a collar with a skull and crossbones for the tag.

As Pipsqueak looked at the tall Diamond Dog in front of him, the small colt had only one thing to say. “Shiver me timbers...”

Ch 2: In which Capt. Guld gets annoyed.

“This town, it be too peaceful for my taste.” a gruff voice echoed in the darkness of Ponyville at midnight. It was a haggard voice, full of regret and sorrow; yet, the voice was also billowing with experience. The voice, in question, belonged to a certain Captain Paw T. Guld, a Diamond Dog with a dark blue coat of fur. Guld scratched the top of his head, his left leg kicking at the relief of his itch. The captain looked out over the bow of his vessel, a bottle of apple rum in his right paw to keep him company on the chilly night. It was like this every night for the old sea dog: search for a town, hunt for treasure, send out the crew, and nurse a nice, stiff drink to fight the cold.

Not that the captain needed the drink to keep warm, he had his blood red jacket for that. Not to mention the thick cotton shirt he wore underneath kept him plenty warm at night, but it was his right as the captain of the Shadow Mare to drink when he felt it was right, and oh was it right. Capt. Guld had sent out his first mate, Spot, to take a look around the strange house they had hit. Last Guld knew, his look out said they were getting close to a small island off the coast of Prance, then BOOM! they wound up marooned on a house in a small town. “I knew this was a bad night to set sail,” the old captain said out loud, “I could feel it in my muzzle.”

Suddenly, the familiar sound of paws hitting the deck caressed Capt. Guld’s ears, and the old dog looked up to see Spot holding a good sized back. “‘Ello Captain.” Spot smiled slyly, “You’ll never guess what I’ve got.”

Guld sighed, he hated when his first mate made him play these stupid guessing games. Every night it was the same thing, ‘You’ll never guess what I’ve got. You’ll never guess what I’ve got.’ It was enough to drive even the most patient of Diamond Dogs insane. “I don’t bloody know Spot... A foal?”

Spot began to laugh his usual dim-witted, low toned laugh... But he stopped quickly. “Gee Captain, how did you know?”

“You see, this is why I’m sick of- Wait what?” The captain asked, his eyebrow cocked in confusion.

Spot opened the bag and turned it upside down, then he began to shake it till a small, brown and white pony fell out of the burlap. The little thing was wearing a bandana on its head, and eye patch with a Jolly Roger over its right eye, and a vest. “Honestly Captain, he got in the way, so I just scooped him up and putt’em in the sack with the bits.”

The foal’s eyes lit up as he looked around, his smile was as big as the ship itself. Pip could tell by the masts alone that this was a Galleon, and that fact alone made his cheer in excitement. At least, until Capt. Guld stood and pushed Pipsqueak to the side, forcing the young colt to fall flat on his face.

“Miserable welp.” Guld snarled, “When I was your age we was afraid of pirates!”

Pip’s eyes lit up once more, and he was back on his feet faster than it usually takes for an Earth Pony. “Excuse me sir... But did you say pirates?”

Guld sighed and turned to Spot, “You had to bring a bloody daft one on board, didn’t ya?” The old sea dog turned back to Pip, “Aye lad, I said pirates. I am Captain Guld, of the Shadow Mare!”

Pipsqueak gasped and put his hooves to his cheeks, “You’re the captain that brought down Typhoon in horn-to-sword combat!”

“Aye, that be true laddy... Can you do me a favor?” Capt. Guld asked, his front right paw patting the little pony.

“Yes sir!” Pip said with a salute.

The pirate captain inhaled softly, smiling joyfully before saying, “GET YOUR FLANK OFF MY BOAT!” Quickly, Spot covered his boss’ mouth, whimpering as he thought of the thrashing he was going to get later on. Soon, Guld pulled his first mate off of him and threw him to the deck, “What the bloody tartarus has gotten into you? Ya brainless, spineless, godless dunderhead!”

“Sir,” Spot stood quickly and saluted, much like Pip was doing, “Pipsqueak told me that there are guards in the surroundings sir.”

“Guards? What kinda small town has guards?” Guld looked at Pip, calling his bluff, “And who names their little foal Pipsqueak? That’s just askin’ for trouble.”

The little pony walked up to the captain (who, for reference, was at least 9 times his size) and replied by saying this, “Right smart ones Captain! I’m Pipsqueak the Pirate, overlooker of all of Ponyville! And I bet I could take you on any day!”

Soon after that, the air around the two dogs and the little pony erupted with laughter, as more Diamond Dogs slowly made their way on deck. These dogs were followed by only three ponies: a male Earth Pony with a large, white, puffy hat; a pegasus with a scar across her left eye; and a unicorn wearing a very fancy vest along with a regal cloak.

“Well lad,” Guld smiled as he drew his very sharp, very pointy cutlass, “you best be makin’ good on that bet.”

X*X*X*X*X*X

Diamond Tiara looked out her window in wonder at the calmness of the night. The only light in the sky was Princess Luna’s pure white moon, while in town a large building was all lit up. It even looked like the building’s roof was lit with small lamps,while some of the inhabitants shuffled about on it. Then Tiara saw something that made her laugh: the flagpole on the building was flying a huge sheet, and it had a smaller black flag on top.

“Must be that little Pipsqueak’s house,” Diamond thought out loud, “only he would take roleplaying this far.”

“Diamond dear!” Tiara’s mother, Stinking Rich, called from downstairs, “It’s time for bed, sweetums!”

“Mother! Princess’ Don’t have bedtimes!” Diamond yelled back.

“They do in this house, now get your flank to sleep!” Stinking called back again.

Diamond sighed as she turned off her lamp and snuggled under the covers, her mind still on that odd Pipsqueak and his pirate obsession... And how it was a little cute to her.

X*X*X*X*X*X

Pipsqueak sat across from Capt. Guld, the cushion he was on was plush and felt like it was made for a king. Guld had opened the door to his private cabin as soon as the rest of the crew was on board, giving Pip the ultimatum of either coming in for a chat or becoming a rug. The foal obviously chose the first option, as it avoided a swift death at the hands of a very scary, yet cool, real life pirates crew.

“Ya see boyo,” Guld began finally, “I can’t be haven’t you blabbing about us to every landlubber pony in this town, now can I?”

Pip shook his head vigorously, sure that this would’ve been easier if he had just pretended to be asleep while Spot broke into his room.

“Good boy, now... How’s about this? I’ll cut you a deal. You keep me crew and me a secret, and I’ll be lettin’ ya be my cabin boy. How’s that?” Guld stuck out his meaty paw, ready to shake Pip’s hoof.

“Wouldn’t it be easier to kill me?” Pipsqueak asked, then covered his mouth with his hooves when he realized what he had just said.

“No,no,no,no,no...No,” the captain replied, “then we’d be dealing with the whole town lookin’ for ya, and let’s just say that a ship in the middle of a town is a bit odd.”

Pip rubbed his chin in thought,"Only if you swear, on the Code, that you won't harm anypony in Ponyville."

The captain snarled at the foal in front of him, then smiled,”Never had a landlubber bind me by the Buccaneer Code before... Deal!” He stuck out paw and shook Pip's hoof to seal the agreement. “Welcome aboard, Pipsqueak the Pirate.”

Ch 3: In which Pipsqueak explains why his parents aren't around.

Ch 3: In which Pipsqueak explains why his parents aren't around.

Pipsqueak yawned as he stumbled out of his nice cosy bed, leaning against the mattress and rubbing the sleep from his eyes with his hooves. The little foal then sat up in a jolt, his mind recalling the events of the previous night completely. Oh please don’t let it be a dream. he thought out, dashing towards the kitchen. The smell of pancakes filled the spotted foal’s nose as he ran down the stairs of his parent’s two story house; he then skidded to a halt right in front of the doorway, as he spotted a large group of Diamond Dogs sitting in the living room.

“It was real!” Pip cried, jumping for joy until a strange voice called him into the kitchen.

“Oy! You, cabin boy! Get your scrawny rump in here and get some breakfast!” the earth pony with the large chef's hat from the night before shouted. Pip then dashes around and between the legs of his new crew, making his way to the counter across from the stove. The earth pony was working as fast as he could, flipping flapjacks and frying eggs so quick it would put a normal pony’s back out;however, being the cook for a whole crew of pirates must’ve given this particular pony some very impressive stamina. “What’ll ya be havin’ boyo?”

“I’ll have a short stack please, mister.” Pipsqueak replied, to which the sound of thunderous laughter erupted from the earth pony.

“Short stack he says!” the cook pony nearly fell to his knees he was laughing so hard, “Oh boy, yer a funny one boyo, you’ll be getting some special grub from ol’ Jack.”

“Jack?” the small foal asked, “Who’s Jack?”

The earth pony couldn’t help but laugh again, then he looked at the new crew member like his head had gotten chopped off. “Boy, are you stupid? Ah’m Jack, call me Hungry Jack. I’ll be bein’ your cook from now on... least till your parents get home.”

Pip frowned a bit, then looked at the back of Jack’s head as the chef went back to work, “They won’t be coming back anytime soon, they both work in Canterlot and leave me here for weeks on end.”

This made Jack stop, now Hungry Jack had been a pirate all his life, literally. He was born to a pirate captain and his wife, he worked on the ship, he even learned to cook on his father’s vessel. So, as you can probably infer, a foal not having his parents around greatly disturbed Jack. “Now, why would they be leavin’ a small lad like yerself behind?”

“Well, they do have a mare that’s supposed to come over and watch me,” Pip explained, “but I haven’t seen her all day.”

Jack then froze in his tracks, “Medium sized mare, brown curls, sandy coat?”

“Yes, um I mean aye.” replied Pip, remembering his pirat lingo, “Why?”

“Uh... No reason boyo, now eat your cakes.”

“You didn’t give me any.” Pipsqueak said, then a huge plate of the fluffiest pancake he had ever seen were pushed in front of him.

“Now if you be excusin’ me.” Hungry Jack said, “I best be... taking the trash out.” With that, the cook quickly exited the kitchen, the sound of his voice shouting for a shovel could be heard echoing all around Pip’s abode. When Pip would leave for school that day, he would notice a pile of stones dug in it a large mound off to the side of the house, but the foal would most likely think nothing of it. After all, pirates liked the bury treasure.

***

“Really?” Diamond Tiara said, her cold gaze settling on Pipsqueak, “You honestly expect us to believe that you have a pirate crew living with you?”

“Not just any pirate crew Tiara!” The excited foal said, “The crew of The Shadow Mare, one of the most notorious crews in Equestrian history!”

Diamond Tiara sighed and shook her head, “This is why you don’t have any friends Pipsqueak... You keep playing pirate, and that’s the only thing you’ll play. Its gotten so lame, that I can’t even make fun of you for it anymore.” Tiara turned, motioning for Silver Spoon to follow her, “Come on Spoony, let’s get away from this dumb little liar.” The two fillies then laughed at the poor spotted foal before heading into the school house, leaving Pip a single ship sailing in a sea of foals.

Pipsqueak couldn’t help but tear up, he felt that everything Diamond had said was true. After Nightmare Night, all the other foals and fillies kept talking to Pip. They were excited to meet the new student who had spoken to Princess Luna, but after a while they all just seemed to pretend he wasn’t there. Only Diamond Tiara and the Cutie Mark Crusaders ever seemed to say anything to him, and after what had happened yesterday Pip doubted that even Apple Bloom would want to talk to him. It’s just not fair! Pipsqueak thought, Why does everypony treat me this way? Like I’m just... In the background...

“It’s not gonna happen today.” the Trottingham foal told himself as he ran away from the school house, and back down the lane to the town itself. Meanwhile, from the window, Diamond Tiara sat at her desk and watched it all. She knew Pip was going to get in trouble for this, even if he had never been absent before. Soon Miss Cheerilee entered the large room, greeting her students as happily as she always did before taking attendance.

“Apple Bloom?” the dark pink mare called.

“Here!” the farm filly replied.

“Scootallo?”

“I’m here.” Scootallo answered, a pencil in her mouth as she drew her latest picture of her hero, Rainbow Dash.

“Sweetie Belle?”

“Present!” Sweetie said, her voice cracking a bit.

“Pipsqueak?” Cheerilee continued, but there was no answer. “Pipsqueak? … Mr. Pipsqueak, you had better not be reading that pirate book again.” Quickly, Diamond Tiara raised her hoof, something she rarely did. In fact, it happened so little that Cheerilee paused for a moment just to register what had happened. “Y-yes Diamond, what do you need?”

“Um...” Tiara chewed her lip as she thought up any excuse that would make sense for Pip leaving class, “Oh, Pipsqueak said he was sick, so he went home. He wanted me and Silver Spoon to tell you before class, but we couldn’t find you. Right Spoony?”

The grey filly yawned, still half asleep since it was quite early. “Huh? Oh, yeah, sick... He had a cold right?”

“Yeah, yeah, that’s it Silver. A cold.” Diamond gave her most convincing ‘I-swear-I’m-not-lying’ smile, hoping it would be enough for the teacher. Thankfully it was, and Cheerilee said she hopped Pip would get better soon. Tiara sighed, rubbing her forehead with the back of her hoof as her gaze fell to the window once more. Maybe I shouldn’t have been so hard on Pipsqueak, the pink filly thought, Maybe I should... No Tiara, Daddy would ground you for a month if he found out you played hookie. Especially after last time, how was I supposed to know that you couldn’t actually pin a tail on a live donkey?! Oh well, I’ll get Silver to come with me and see him. Maybe I do need to apologize.

***

The rest of the day went off as it usually did: math seemed to bore everypony, history was dull, and the CMC’s did something that made Cheerilee pin a note to each of their saddle bags asking for a conference with their parents. None of it mattered to Diamond Tiara as she trotted along the lane, Silver Spoon following quickly behind.

“So,” Silver began to say, panting between every other word, “you’re actually going to apologize to Pipsqueak, right?”

“For the hundredth time Spoon, yes!” Diamond yelled back at her best friend, “How is that so hard to believe? … Don’t answer that!” The tiara clad filly added, just as Silver spoon opened her mouth to explain why it was hard for her to picture Diamond Tiara, queen of the drama queens, apologizing... Let alone knowing how to say ‘sorry’.

“Do you even know which house is Pipsqueaks?” the glasses wearing pony asked, “For all we know we just passed it.” Suddenly, Diamond and Silver Spoon stopped as they turned the corner, their mouths dropping to the ground like two ripe apples. Across the block from where the two little ponies stood was a tall, wooden ship with a skull and crossbones on the flag.

“Silver...” Diamond Tiara said.

“Y...Yes Diamond?” Her friend answered.

“I think we found Pip’s house.”

Ch 4: In which Pip saves Diamond

Diamond Tiara and Silver Spoon stood in awe of the huge ship in front of them. Never in a million years did the two fillies think they’d ever see a ship so big, even Tiara’s family yacht was a dingy compared to this mammoth of a vessel. The pink filly was the first to say something, he head held high as she turned to her friend.

“Well... I’m goin’ home.”

“Wait!” Silver Spoon said, her face looking as steady as stone, “We came here so you could apologize to Pip, so I’m not letting you leave till you say you’re sorry Dia.”

“Oh come on Spoony, look at that thing!” Diamond pointed her hoof at the large ship, “It’s bigger than my house, and you’ve seen how big my house is.”

“Yeah, your house is pretty big... But that’s not the point. The point is that you need to patch things up with your coltfriend.”

“He’s not my coltfriend! He’s not even my friend, you’re my friend and even I wouldn’t go into that place to find you.” Tiara covered her mouth with her hoof as soon as she realized what she said. The grey filly stared at her friend, dumbstruck, until tears began to roll out of her eyes. Silver Spoon ran from her friend faster than the poor filly had ever ran before, a stream of tears falling from her face as her hooves thundered away.

“Spoony! Silver!” Diamond called to her friend, “Come on, you know I didn’t mean it! I just... I don’t want to go in there...” The rich pony looked down at the dirt under her, kicking it as she stared at a small puddle made by her friend’s tears. “What the buck is wrong with me?”

“Such language comin’ from a lil filly.” A large Diamond Dog said, towering behind the sulking pony. His long blue coat billowing in the sudden wind, his Jolly Rodger tag jingling on his collar. “Dinn’t your parents ever teach you any manners?”

Diamond opened her mouth to scream, but nothing came out. She froze in front of the big, grey beast out of shock and fear. Spot cocked his head to the side and picked the filly up by her tail, which somehow had become so frozen in fear that it was stiff and held her body up as well. The first mate just chalked that up to some odd special talent that this little filly had. “Honestly lil’ girl, I’da let ya go off ta yer friend,” Spot lied, “but, ya be wearin’ some pretty expensive headgear there.” The Diamond Dog pirate pointed at the pink filly’s crystal, diamond studded tiara. “And, as ya probably be knowin’, I be a Diamond Dog. And we Diamond Dogs just love our diamonds.” With that, the lumbering first mate of Captain Guld’s crew made his way back to his ship, unaware that a set of bespeckled eyes were watching him just through the brush.

***

Pipsqueak finished his second bowl of ice cream with gusto, feeling much better after an afternoon of singing and bothering Guld’s crew to go on a treasure hunt. The spotted foal sat on his cushion and watched Hungry Jack start preparing dinner for the entire crew. He could see the disgust in the chef pony’s eyes as he placed a huge chicken into the oven.

“Why do you make them things that you don’t want to make?” Pip asked, licking his ice cream spoon clean.

“Well boyo, it’s because of one simple fact.” Hungry Jack looked right into the foal’s eyes, not blinking as he stated, “Never say no to the cap’in.”

“But what if he told you to jump off the cliff?” the pirate loving pony asked, remembering Diamond Tiara saying something similar to Apple Bloom when she had to help her big sister with something.

“You best be believing I’d be at the bottom of that cliff faster then you can say ‘Oi! Look a’im jump!’”

“Ah, he isn’t that scary.” Pipsqueak replied, “I bet old Captain Whitehorn could take him down!”

“Whitehorn aye?” the cold calm voice of Capt. Guld said from behind Pipsqueak. Hungry Jack fumbled to salute, while Pip turn turned around in fear. “Boy, do you know exactly how old Whitehorn died?”

“Um... uh... N-no.” the spotted foal answered truthfully.

Guld smiled and pulled a long, black bladed cutlass from a guard at his side. “This blade, my blade, took his life with one quick slice.” The captain poked Pip’s cushion with the tip of the sword, “And if’n I dinn’t like yer spirit so much, i’d have cut you open like a guppy the moment I saw ya.” Capt. Culd paused, his eyes looking from Hungry to Pip and back, “Now get yer hides to the deck. We’ve got a prisoner to be dealin’ with.”

***

The crew was silent as the grave when Capt. Guld emerged from below deck. The old sea Diamond Dog took his place behind the wheel of the ship, while Pipsqueak and Hungry Jack tried to find a place in the circle of their fellow crew mates. In the center of the ring was a small burlap sack, much like the one Spot had carried Pip to the ship in only a day before. As soon as that thought crossed the Trottingham foal’s mind, the distinct sound of metal hitting wood echoed throughout the air of the Shadow Mare.

“Oy, the lot of ya!” Spot called out from beside his captain. “We have a little trespasser that we need to take care of, if you catch my drift.” As quick as a whip, one of the crew men sliced open the sack, and Diamond Tiara came tumbling out.

“Diamond!” Pipsqueak cried as he rushed towards his classmate, “Are you ok?”

“Cabin Boy Pip,” Guld began, his paw rubbing his chin as he watched the spectical, “who, exactly, be this wench?”

“Wench?!” the pink earth filly yelled as she stood, “I am Diamond Tiara! My father’s Filthy Rich, owner of Rich’s Barnyard Bargains, and he’s the richest pony in this part of Equestria! He could buy and sell each and everyone of you dirty street performers!” As Tiara panted, she ran out of breath telling the pirate crew off in such a short amount of time, Guld and all thirty of his Dogs and ponies just stared at the small, angry filly in shock... And then they laughed their tails off.

“St-Street performers she says!” Spot hollered as he slapped his knees, trying to keep from falling.

“Be careful Spot,” Guld said, slowly cracking a smile, “‘er daddy could buy and sell each of us!” The crew couldn’t hold back anymore, and as if they had planned it out in advance, each of them fall to the deck like a row of dominoes.

“Wh... What’s so funny?” Diamond Tiara asked Pipsqueak (who was rolling around on the deck, nearly turning blue from laughing.)

“Th-They aren’t performers Tiara!” the small foal said in between laughs, “They-They’re real pirates! Like I told you!”

“R...Real pirates?” Diamond asked out loud.

“Yeah! And they’ll probably hold you for ransom, so you’re dad will pay out the nose to get you back!” Pipsqueak was slowly getting his hoofing back, the laughter had been like his first voyage at sea. Of course, Captain Guld was the first to break out of the spell of pure, unadulterated laughter.

“Hmm... Pip me boy, I think you may have an idea there.” the aged captain said, “I was just going to keelhaul the lass, but if her papa really is as rich as she says she is...”

“I think she’s tellin’ the truth Cap’in,” Spot said, holding up Tiara’s tiara, “how else would a lil ragamuffin like ‘er have such a pretty pretty on her noggin?” Guld snatched the jewel encrusted head piece from his first mate, and examined it closely.

“I dunno Spotty, looks a bit fabricated to me.” the captain then turned to the regal, and only, unicorn in his crew, “Eyefer, get yer flank over here and do yer job!”

“Oui oui captain.” the vest and cape wearing unicorn, Eyefer Zetail, said as he rushed to the wheel of the ship. Gently, the odd pony levitated the small crown in front of his face, and studied every tiny curve and cross of Diamond’s most prized possession. “Sir, I believe that la jolie pouliche es telling the truth. This tiara, under my estimate of course, is worth about three-thousand bits.”

“Th...Thr thr thr... Three-thousand for this little thing?” Guld stammered as he scratched one of the shining diamonds on the tiara with his claw, which didn’t leave a scratch.

“Mais oui.” Eyefer said, grinning from ear to ear.

“Well then..” the captain looked down at Diamond, his latest haul, “We seem to have a new guest on board. Least till her papa gives us a haul one-hundred times her worth.”

Ch 5: In which hi-jinks ensue

Ch 5: In which hi-jinks ensue

“You can’t just keep me here!” Diamond Tiara yelled from the brig of the Shadow Mare, “I’m a kid!”

“Yer a loud mouth’s what you are.” Spot replied. The first mate had the ‘honor’ of guarding the prisoners tonight, and seeing as there was only one it seemed like it would be an easy job. However, from minute one of her imprisonment, the pink earth filly never seemed to shut her trap. She complained on and on about anything she could get her hooves on. First it was that the bench was too dusty, then it was that she was allergic to the bars (which was a complete lie), and now it was that she was too young to be thrown in the ship’s prison. “I’ve ‘ad it up to ‘ere with you girly.” the pirate dog pointed to the top of his head, “Now, for the sake of your bloody princess, shut up!”

Spot turned to look at the small pony, but regretted it instantly. Tiara’s eyes were big and filled with tears as she met the hulking Diamond Dog’s gaze. She began to whimper, and her lip trembled like a house in a bad storm. “Oh, come on now... No need fer tears.” Spot said, holding up his paws as if he were blocking an attack from the rich filly.

“Y...you... YOU’RE MEAN!” the pink school filly shouted as tears erupted from her eyes. The first mate stumbled back from the shock of Diamond’s cry, and watched as she began to shed more tears than a lobster at a seafood buffet. At this point, the blue coated Diamond Dog was at a loss, he had no clue how to handle this situation. Spot had dealt with crazy bounty hunters, giant sea monsters, and even the occasional rival crew at times, but this filly! This little girl was supposed to be nothing more than another ransome to him, yet Spot couldn’t help but feel sorry for the tiny, apparently tear filled, thing.

“Now now girly, it’s ok. No need to cry, it’s not like we’re gonna hurt ya.” Spot kneeled down near the cell, but kept his paws up incase the filly wanted to try and hit him. “Well we be wanting is yer daddy’s money, after that we might be shovin’ off.”

“Sh...Shoving off? W... With Pipsqueak?” the tiara-less filly asked.

“Well... Aye.” Spot answered, a little confused by the question, “Ye be his wrench?”

“W...Wrench? WRENCH!?” Diamond screamed, glaring daggers at the large beast. “How dare you call me a wrench! I am Diamond Platinum Tiara the Third! One of the richest fillies in Equestria! I am a lady, thank you very much! And I will not have some sniveling, slobbering, sickening, oversized, overweight, idiotic, lazy-eyed brute like you undermining that! Do I make myself clear!?”

“Yes ma’am!” Spot said quickly, saluting much like he did when the Captain rung him out. Unfortunately for the first mate, Capt. Guld had decided to check the brig at just that minute. The angry look on Guld’s face could’ve sent even the bravest of Princess’ Celestia’s personal guards into a state of pure fear.

“SPOT!” Paw T. Guld yelled, causing his underling to drop his paw and turn slowly, trembling as he faced his captain.

“A...Aye sir?” the first mate asked, his voice quiet as a mouse.

Guld walked right up to the larger dog, his eyes burning like embers as he growled at Spot. “You call yerself a pirate.” the Captain began, “All ye had ta do was watch one little filly while me and the rest of the crew thought up a way to get the ransom note to her father... A job so simple, so easy, that even a great dunderhead like you couldn’t be founderin’ it.” Guld too a deep breath, and continued, “However, it seems that I be wrong about one thing. Yer not just a dunderhead Spot, do you know what y’are?” Capt. Guld paused and gave his first mate enough time to shake his head, “YE BE THE KING OF THE DUNDERHEADS!”

The Captain quickly took off his hat and slapped his first mate with it, causing the larger dog to flinch. “Now unlock that cell, ye mangy mutt. Ye be sittin’ in there with her, I’ll send Pip down to watch ya. At least he’s made more of a contribution to our cause then ye have... Dunderhead.”

Spot followed his captain’s orders to the letter, unlocking the cell and quickly getting in before relocking it. The Diamond Dog then tossed the keys on to the jailer’s table with ease, before sitting on the dust covered bench next to Diamond Tiara.

“That guy’s kind of a jerk.” Tiara said to her new cell mate.

“Aye,” the first mate nodded in agreement, “but he be the best sailor in the Equine Mane, and he be the captain.”

“I guess that makes sense,” Diamond said, curling up on the hard wooden seat, “daddy does silly things too, but ponies listen to him ‘cause he made a little store into a chain of supermarkets.”

“Lass?”

“Yeah Spot?”

“What be a supermarket?”

***

Pipsqueak had been half asleep when a loud cheer came from his living room. “The crew must’ve thought of a way to get the note to Rich without being seen.” the Trottingham foal yawned as he got out of bed and headed down to what the pirates were now calling their meeting room. As soon as the small colt entered the room, his ears were assaulted by the sounds of an accordion wailing. In Pip’s eyes it was too early to celebrate, but with all the Diamond Dog’s dancing the foal couldn’t help but join in. The smell of grog and ale filled Pipsqueak’s nose as he spun around, the crew cheering him on as he danced to the odd shanty playing. The words echoed in his ears like an old lullaby:

Whether ye be a banshee, or just a bloody ghost
Anit none of ye be frightin’ as the Cappin’ that we boast
His eye be black as jet, and his teeth be sharp as blades
His name be Paw Guld, and he’s killin’ them in spades!

Suddenly, a door slammed open and the music stopped, leaving Pip dancing and spinning to the sound of silence as Capt. Guld walked up to him.

“Lad... Lad. LAD!” the captain yelled, causing Pipsqueak to stop and fall on his plot, “Lad, Spot be a worse dunderhead then even I could imagine, can ye go down to the brig and make sure he and the loud lassie stay locked up?”

The small colt stood and saluted to his captain, “Aye,aye!”

“That be a good boy, oy!” Guld said as he turned to the rest of his crew, “Roguefeather, get yer flank over here and go with Pip, that’s an order.” As Pipsqueak made his way to the door, the red maned pegasus with a battle scar across his eye followed him out.

“So, how’s it feel bein’ Guld’s new favorite?” the slaty pegasus asked. Pip looked at the older pony’s flank and spied a pair of sabers, crossed in battle as his cutie mark. Marcus Roguefeather was the Shadow Mare’s weapon specialist, and even Pipsqueak remembered the stories of how the battle hardened pony had went head to head with Guld multiple times before joining the crew.

“It’s not too bad.” the cabin boy replied, adjusting the bandana on his head.

“Aye... As long as ya stay on the old bastard’s good side, right?” Roguefeather laughed as he and the foal headed down to the brig, unaware that behind them in the shadows was a small spy, getting ready to free her friend.