Image imported from derpibooru 
Original Description:
 
The evening fog swaddled the sloop Mandatory Friendship as it silently glided into the harbor. Captain Rarity stood on the aftercastle of the sloop and smiled. They’d sailed from Cabo San Luna 5 days ago and had been planning this raid for more than a month. Gathered in clusters were the dark silhouettes of anchored, visiting ships.
 
Amongst them was the focus of tonight’s raid. The modest sized brig The Reefing Princess. The ship itself wasn’t their primary target; instead they were after the contents of a small strongbox that was suppose to be in the Captain’s private hold. Inside it was a powerful wind summoning and control charm that would give Rarity and her crew a great advantage.
 
The sloops cannons were armed, but tonight they would be used only if this operation went terribly wrong. In fact strict orders had been given concerning all personal firearms. Either leather covers had to be on the frizzens of the locks, or the pans of said locks were free of powder. There could be no accidental discharges from a dropped or mishandled firearm. Stealth, surprise, and cunning would be their greatest weapons tonight.
 
The unicorn watched as her crew quietly reefed the sloops sails. Momentum, careful use of the helm, and the currents flowing into the harbor would gradually carry them almost to their prey. From there they’d quietly lower the ship’s boats and travel the final distance to the target. Earlier in the day the pulleys and tackle for the ship’s boats had been heavily greased to reduce the sound they’d make when they were used. Thick, long, padded coils of cotton duck stuffed with tow had been attached to the gunwales of the boats. It was hoped that these would reduce the sound of the boat hulls scrapping as they were lowered into the water and bumped up against the brig’s hull.
 
Out of the fog a figure swooped down and landed next to Rarity. Second Mate Rainbow Dash leaned over and whispered in her captain’s ear. “Okay Captain. Me and my team have made sure they’ll be fog as thick as ships porridge fer the next couple of hours. After that no guarantees. We ready to go?”
 
The white mare’s eyes seemed to twinkle even in these dim conditions. Softly she replied. “Almost darling. It’s time for the star of tonight’s performance to make their appearance.”
 
Quietly she made her way down the stair from the aftercastle and across the main deck to shadowy figure who was sitting crossed legged on the deck. Kneeling down alongside she addressed Fluttershy.
 
“Flutter dear. It’s almost show time. Is our lead actor ready?”
 
Rarity could feel more than see the chiffon yellow mare smile in dark and fog. “Oh yes Captain.” She nodded her head. “Krakky is already to head out. You just give the word!”
 
“Well darling, I think that time is now. By the time your friend can swim over. Climb onboard, and make sure one rope ladder is dangling down the side of the Reefing Princess. We should be pulling up alongside it.”
 
Fluttershy reached into a large bucket of water that was sitting on the deck in front of her. From it she withdrew an octopus; cradling it gently in her hands she spoke to it in a soft cooing voice.
 
“Okay Krakky! It’s time for you to head out. Just do it the way I’ve taught you and everything will be fine!” As she spoke the octopus looked her in the eyes as it tentacles randomly touched and caressed the mare.
 
Carefully Futtershy carried the Krakky over to the side of the sloop and then placed the octopus in a bucket tied to a rope. Then she reached into her cleavage and withdrew a very small sheath knife. She handed the knife to the octopus.
 
“Now Krakky. If they’ve tied the ladder tight and you can’t undo the knot use this to cut it loose. Once you’re done, please swim back to this ship. Now. On your way.” Then she slowly lowered the bucket into water and the octopus headed off on its mission.
 
This is one of the request drawings from last night’s All Pirates themed Picarto stream. And since today is International Talk Like a Pirate Day it seemed appropriate to post this. As I was finishing this drawing today this was the story that popped into my head. I find it amusing that I got a request for Pirate Fluttershy last year as well. >>2449542s