Pipsqueak: The most gentlecoltly anarchist pirate ever

(A/N: Picture does not match description of Pipsqueak, I couldn't find a gentlecolt version of it. So I chose a pirate ;_;. Whatevs, enjoy.)

Celestia sighed as the head of her personal security smacked his hoof against the table. "Princess! You have to take him seriously! He's vandalized over 30 shops and businesses and he's been cited on numerous occasions to be seen indecently in public! He's an absolute loon!"

Celestia only smiled. "He may be a complete loon, but he's funny if you ask me." She was still laughing internally at the stunt he pulled in Lower Manehattan.

Aquillus only snorted. "I'd say putting a massive eye patch on the Statue of Harmony was a serious crime but". He made a shrugging motion.

Celestia merely sighed and rolled her eyes. "Oh calm down Aquillus! I don't think we should be taking him too seriously! I mean all he's been doing is playing pranks and such! He reminds me of a certain pink filly." She sighed as nostalgia overtook her.

Aquillus grunted. "Celestia i'm only doing this for your protection! He's an unruly vagabond! We don't know when or where he'll strike! You've seen how unpredictable he is! Hooflin, Prance, Trottingham, San Burneighdeno! And even in Canterlot! All in a matter of weeks! I don't know how he does it but he does!"

Celestia meanwhile had been trying her hardest not to laugh at the memories of each incident.

Failing to do so, she guffawed long and hard. "Come now Aquillus! Even he's smart enough not to crash the Galla! It's the single biggest event in Equestria! There'll be guards from even Gerpony attending! And everypony knows  that no one messes with them."

He gave her a dead-stare. "That's what you said about the Annual Guard's March! and he had his stallions pelt us with pies and paint bombs!"

The Annual Guard's March was a celebration and commemoration of all the ponies serving in Her Majesty's Service. They would gather in accordance to their rank and army, Naval to Marine to Air Force, and they would parade through the streets of Canterlot. This particular year however, a certain self-titled 'pirate' and his merry men had come from the crowd in a quite organized flash mob and pelted the partitioners in a massive barrage.

Celestia still remembered how he swooped down from a building and landed on her Float as he shouted "FOOOD FIGHT!" Prompting the crowd as well as the soldiers to partake in a massive fight lasting the whole day. It had finally been shut down when reinforcements from Gerpony and Prance had arrived late in the evening, but by this time the initiators had fled the scene.

Celestia still chuckled when she remembered how easily he had made buffoons out of even the most decorated of Detectives.

And with that last ditty, she got out of her chair and walked away. "Like I said, even he doesn't have the audacity to crash the Galla! You're worrying too much!"

What Celestia didn't see when she turned around was Aquillus's mischievous grin.

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He had been playing Tarot with a couple of his men when he got the call.

All clear boss. She didn't even have a clue!

He smiled as he got out of his chair, all around him his men lazed around due to lack of activity. The small tavern was filled with smoke and drunken laughter as the boys celebrated yet another pranking success. Suddenly he hopped up on the stage and shouted.

"ALRIGHT BOYOS! I'VE JUST GOT WORD FROM OUR INSIDE MAN THAT THE BIG BIRD DOESN'T SUSPECT A THING!" He smiled as cheers echoed through the cobblestone walls.

"Who's ready to crash us a party?!?" he asked, and was satisfyingly greeted by a rowdy cheer.

"This time we'll be dealing with the upper crust of society! Those who are so stuck in their ways they might as well be stone! This time we're pulling all the stops! LET'S TURN THAT PARTY INTO A CARNIVAL OF FUN!"

Another, louder roar of laughter accompanied him as he hopped off stage and grabbed his trusty top hat.

"C'mon girls and boys! Come one, come all! To Pipsqueak's Circus of Fun !"

HOORAH! Hoorah! To fun we are called! Throw cakes and pies and spray and burn down!

"Come on you lot! I can't hear you! Why do we do this?"

To spread the smiles! To spread the cheer! To let the foals play!

"Oh come now! That rhythm doesn't make any sense!"

Why does it have to?!?

"THAT'S THE SPIRIT!"

~~~~

"Hello! Thank you for coming to the Grand Galloping Galla!" Celestia stood at the top of the double spiral staircase greeting all the attendees of the Gala with a soft smile. Inside she was groaning though. The greetings were purely ceremonial. Actually, the whole Galla was ceremonial. All anypony did was sip their drinks and mingle for the night. Everypony attending was from the Upper Echelons of society, from nieces to nephews, from bankers to barons and back again. Everypony was so stiff, so formal.

It was times like this that Celestia would revert back into herself, she would let the world slide as she thought and imagined 'the glory days'.

After about 2 straight hours of greeting ponies, a guard notified her that all the attendees were present and that he main play of the night was about to being.

Sighing with relief, she made her way to the Solaris Hall where the play 'a midwinter night's dream' was being held.

"Here's your seat Princess." Notified a guard as he pulled back her seat in the skybox.

Celestia sighed contently, two hours on her hooves killed her. It was nice to finally sit back and enjoy a show, especially since it heralded the end of a night she so thoroughly dreaded.

"Show time." She mused silently as she waited for the chatter and noise of the partitioners to quiet down.

~~~~

"Whew!" He said as his men finally rounded up and gagged the remainder of the actors.

"Boss! We're all set!" Called one of men from the rafters.

"Alright boys n girls! It's show time!" he replied his merry men as the stage was lifted.

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Celestia had been waiting eagerly for the play to begin. As she curtains lifted however, she was met with a surprise. A large gaunt stallion stood at the front of the stage, all around him, mares and stallions with bandannas and eye patches, fake peg legs and vests not seen since the Pirate Era were holding instruments, large grins on their faces.

The stallion in question, was wearing nothing but a single large Top hat, it was adorned with multiple ribbons of different fabrics. Even though she wasn't a tailor, she could see that amongst the multiple colors of the spectrum adorned on his hat, there was silk, velvet, nylon, you name it, it was there.

He was holding his hat down with a single hoof, just far enough to cover his eyes, but not far enough to cover his grin.

And he spoke, his voice filled with joy as it resounded off the marble halls.

"GOOD EVENING MARES AND GENTLECOLTS! WELCOME TO PIPSQUEAK'S CARNIVAL!" At once the characters on stage began going wild, doing cartwheels and back flips, jumping and free-running off walls.

Some put putting flaming sticks in their mouths and spewed flames. It was a carnival alright. A group of them began chasing one who had white face paint a huge clown afro.

The whole auditorium was struck speechless by this turn of events. Celestia herself was smiling uncontrollably. Suddenly, the ringmaster of the madness cleared his throat.

"Attention! Come on boys n' girls! Let's do what we came her to do!" And just like that, the ponies on stage holding instruments suddenly tensed and drew their instruments to their lips. Celestia counted an Accordion, two trumpets, a sax, a drum kit, a violin, and a Prench Horn.

And suddenly, the whole lot of them became silent as they readied themselves.

Celestia's insatiably wide grin grew even more as she watched them. "He actually did it!" She excitedly whispered, her soul laughing on the inside.