“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.”