The Many Tales of Pipsqueak and the Pirates

by Muleicous


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...”