PirateAnon and his first mate, Pinkie Pie

"ATTACK AND HOLD NO QUARTER, less ye be wanted to dance the hempen when the guards get here," you bellow atop your lungs as you and your pink comrade storm the doors of Sugarcube Corner.
>Pinkie darts over the counter and loads as many treats as the bag can hold as you swing your sword about to keep the common rabble hidden under the table in fear.
>"All loaded cap'n," Pinkie yells with a salute.
"Then we best be off."
>The two of you dart out and head up for your secret base of operations by the lake.
>There you two share the spoils.
>"So, how'd I do?"
>She asks while she chews with her mouth open. A few bits of her food fly into your face, but you pay it no mind. Perhaps if you were a man of higher cloth, or even a man who cared for cleanliness, you might find her lack of manners annoying.
>To you, it has it's own charm. It reminds you of your old crew, back home where most wouldn't even know what the word bath meant.
"You're swift, I'll give ya that. But you're lacking the attitude and action. Ye didn't even try to swing at the lass behind the counter, even though I said hold no quarter."
>"But I did hold no quarter, see," she replies as she opens the bag of confectionery spoils, "No quarter pieces of pies or cakes."
"That's... That's not what that means."
>"Oh, what does it mean?"
"It means no holding back. Gut a man if you have to."
>"That doesn't sound very nice. Stealing is one thing, but every pony does as we ask, why do we have to hit them?"
>"Fear is the greatest tool a pirate can have, why when I sailed under Blackbeard's banner, he could strike fear--"
>As you tell your tale of your old pirate comrade, Pinkie's eyes light up in wonder and fascination.
>If you were some kind of lady, you'd dare call her cute. But instead you just laugh at yourself.
"What am I saying? There's nothing fearful about a fuzzy little pink pony who'd squee at the promise of a cuddle."
>"WHAT?! I AM TOO FEARFUL!"
>Her face now pushes against yours and her eyes are lit up in determination.
"I like the passion in your belly Pink. Tell you what, maybe if we dress you up for the part ye'll start striking fear like a match."
>"Oh boy, I know just where to get some."

-----Pinkie's PoV-----
>You've lead Captain Anonymous to Carousel Boutique.
>Rarity will be able to make some clothes quickly for you.
"Alright, first thing is we'll pretend to be legitimate customers. But when the mare be done with your gear, we'll case the joint. Got it?"
>You pause just outside the door after Anon's words and a pang of guilt tears through you.
>"Uh, say, Captain."
"What is it Pink?"
>"Mind if I do this one alone? I can't well prove myself as fearful if I've got you helping me out every step of the way."
"Taking the initiative are we? On your way then, get it done."
>You nod and salute before darting inside.
>"Rarity?"
>"Pinkie darling? How's things?" Rarity asks from behind some changing panels.
>"Uh, good. Good."
>"Wonderful, tell me, what do you think of these?"
>Rarity steps out in some bizarre upper class outfit that's probably inspired by the latest Manehattan fashion.
>"Great. Can I get some clothes?"
>"Let me guess, you want something to look like that human who smells like Dash's sport's gear."
>She's posing in front of the mirror as she talks, scanning over the clothes she's wearing with judging and disapproving eyes.
>"Yeah. Is that okay?"
>"Of course dear," she replies with a sigh, "I must admit, the style is rather unique so I've been working on something similar to my own design. In your measurements I might add. I figured you'd want to match sooner or later."
>"Thank you so much Rarity," you reply with a gleeful skip over to her.
>You're about to reach out for a hug when she holds out a hoof to keep you at arms reach.
>"But first, you need to explain a why you're even hanging around such a character? And I heard about Sugarcube Corner, what has come over you?
>"I'm just trying to be friends with him. He's a lot of fun, and... caring in funny a way once you get to know him."
>"But the man is so... Disreputable. I worry about you hanging around him, he's an awful influence on you."
>"Then who'll be his friend?"
>"Why does that matter?"
>You sink low, especially when Rarity raises her voice at her latest remark. You know your friends are worried about you plus Anon's way of things haven't really earned him any favourable opinions.
>"He's got nopony else Rarity. He's all alone."
>You look out the window to see Anon sitting against a tree. His hat is tilted just enough so he can still see the ponies going about their business in the town.
>"That doesn't mean you should help him steal, what if somepony gets hurt?"
>"I paid for all the sweets we took. I left a little pouch while I was grabbing things."
>Rarity continues to look at your with disappointed eyes.
>"I'm trying to help him change," you finally give in, "He can't just stop being the way he is. It'll take time to reform him, like Discord but he'll never get there if he doesn't have someone."
>Rarara just sighs and holds out some folded clothes with her magic just in front of you.
>"Take them before I change my mind."
>You sweep the mare up into a hug before disappearing into a changing room with the clothes.
>Once the clothes are on, you head outside to show of your new duds proudly to your captain.
>"What do you think cap'n? Snazzy or what!"
>He laughs for a moment. You're pretty sure it's not in a mocking way, he seems to laugh over a lot of things like any time he's likes something. This sounds like one of those laughs.
"I like it. Just one last detail I think," answers Anon.
>He takes of the red cloth around his waist and places it around your neck before using one of his cufflinks to keep it in place.
"S'called a stock tie. Figured it'd suit ya."
>He takes a step back to take your getup in one last time before nodding in approval.
>"Thanks captain!"
"Now, normally I wouldn't be letting ye wear a hat like that because yer not a cap'n but I'll let it slide cause yer me first mate."
>"Does that mean I'm your top, most important friend?"
"Actually, that's not what," he pauses for a moment to let out a breath, "Yes, Pinkie, that's what it means. Come on, I'm the mood for rum."
>"Can we tell campfire stories again?"
"Aye matey. We'll drink, sing and tell tales until we can't pry our eyes open anymore."