The Tale of the Shameless Sloop

by Uh-hmmm

Rating: mature
Tags: Anon, My Little Pony: Friendship is Magic, Second Person, Comedy, Profanity, Adventure, Human
Length: 4828

The sea will lay claim to the soul of every sailor it can, through any number of methods. The Pirate Captain Bad Apple can't complain about the one that got her. (RGRE) {Has first and second person versions}

The sea will lay claim to the soul of every sailor it can, through any number of methods. The Pirate Captain Bad Apple can't complain about the one that got her.
(RGRE)
{This story has two versions, the last chapter is the first person version.}

Published 2020-10-31 17:50:00 UTC
Last updated 2020-10-31 17:50:00 UTC

Second Person POV

You are Captain Bad Apple, airing out your cot AGAIN. You still don’t understand why your morning dew is so much heavier on the Sloop than on the shore. You better not have an unawakened fetish for ships or the waves. That’s how the sea claims mares, you are pretty sure. You open your cabin and trot out onto the deck. Three Sheets is already up in the rigging, the tauress’ teats gently undulating in the wind.

“Morning, Captain! It’s going to be a lucky day, I can feel it in my nips!”

You roll your eyes.

“You said the same thing the day we got chased out of Port Outsbutt.”

Three Sheets grins.

“And I was right, I got to buck the governess’ son before we had to leave.”

“Which is why we had to leave. Get chummy and you’ll be chum, got it?”

She salutes.

“Aye Aye cap’n!”

You sigh and head to the mess. Hard Tack ladles you a bowl of oatmeal and dried berries. You nod your thanks to the unicorn mare. As you dig in, you ask,

“How are we doing on rations?”

Tack sits back on her thick flanks, rubbing her chin in thought.

“We’re good for about two months, longer if you let me bake biscuits.”

You nod, that’s about what you figured.

“We should be making port before then. And do I really need to tell you not to bake again?”

She frowns.

“I think I figured out where I went wrong, if Keg would just let me use her flour stock…”

You shake your head.

“Experiment with your own bits. We don’t need culinary armor plates right now.”

Hard Tack sighs and goes back to stirring the pot of oatmeal. You finish your bowl and leave it in the bucket to soak. Powder Keg wanders in, and you still can’t get over her appearance. Built like a Canterlot noble, tall and slim, but her tail cut indecently short and yet still singed at the ends. You tune out their bickering as you head to the back of the Shameless Sloop. You haul the anchor up, grinning as you bring all of your earth pony strength to bear on the winch wheel. It’s always a relief to really exert yourself in something and not risk bucking a hole in your ship. You slow down as the water bulges under the chain and the anchor begins to break the surface. When it is fully out, you pull the brake on the winch and trot up to mare the helm. Sheets gives you a nod, and you call out mostly for the sake of the other two of your crew.

“Unfurl the main and head!”

Sheets undoes a few knots in her web of ropes and pulleys, and the two sails billow out and boom as they catch the wind. The Shameless Sloop jerks forward, plowing through the sea.
Let’s see what the new dawn holds.

A fussy merchant vessel, it would seem.

“Keg! Fire a warning shot across his bow!”

The unicorn grins, her horn lighting with a baleful red. The cannon thunders as it launches the iron ball, just barely clipping the rails of the merchant ship. A moment later, they answer with a shot aimed at your deck. You gallop to where it would hit and pivot, leaning forward. Your hind legs bunch up, hooves close together and waiting for… With a metallic clang, the cannonball hits your hooves just as you buck, sending it back into side of the merchant vessel.

“Keg, clear their deck!”

A dozen clay pots arc across the water and shatter across the barque’s deck, covering it in a haze of flour dust. Then Keg’s fuses run down and fire blooms. Not much later, the merchant runs a white flag, and you bring the Sloop alongside and swing across. You land on a sooty wasteland, still warm and embers glowing along the edges. The stench of burned fur fills the air, but you ignore it and the groans of the injured as you approach the grim-faced captain. You come to a stop before her, your hardtack vest clattering dully.

“I’m glad you have come to see reason. Now, let’s see your cargo.”

The captain nods and trots down below decks. You follow her down, keeping an eye out for any-

The wall by the stairs splinters as a bullet bursts through it and shatters a hardtack plate on your side before clattering to the floor. You grunt at the impact, then buck the wall down. Among the splinters and shards of wood, you find a dazed mare, barely grown from a filly into a mare. You kick the pistol away from her and glance at the captain, who has grown quite pale.

“Mercy, good pirate. Please...spare my daughter, this is her first encounter on the high seas.”

You take another look at the fallen mare, and you can see the resemblance. You frown.

“She broke your flag of truce, I should make an example of her to keep such underhanded dealings at bay.”

The captain begins to sweat. You look her in the eye.

“You are a mare of honor, are you not?”

She swallows.

“I am.”

You nod.

“Give the filly a good birching, once I leave. And we’ll be taking your entire stock of flour, among other things.”

That should make Tack happy. The captain untenses.

“I’ll see it done myself.”

You nod and start sniffing around the cargo hold.

The haul is decent, a few cases of rum, plenty of spices, a gilded jewelry box, and some useful maps. Most of their hold is full of iron ore, which you leave alone. Still, nothing that would qualify for Sheet’s forecast of Discord’s Luck. Leagues later, the smell of flour being tortured into ceramic fills the air, and you are beginning to get nervous. The next trade route you want to hit is still a day’s travel away, with nothing but the open ocean between you and it. You glance up at Three Sheets. She’s wrapping her teats down, a grim expression on her face.

“Cap’n, I swear I didn’t buck anypony’s son this time. Clouds starboard, and I bet my last bit that they aren’t natural.”

You turn to stare at the horizon, and the dark cloudbank looming, small black specks flitting around it. Your heart drops. You had thought you were keeping things low-key, hitting small targets and keeping on the move. But it seems the Crown has decided to nip you in the bud.

“Trim the sails! Batten down the hatches!”

You grip the wheel grimly. A normal storm, you could heave to and ride out. A Pegasus-driven one…

This may be the end for you and the Shameless Sloop. The winds rise, whipping the brine into the air. A great hiss fills the air as rain sheets into the rolling sea. You steer as best you can, angling into the wind. The rain splatters against you, instantly soaking you to the bone. Thunder begins to roll as the Royal Airforce builds up charge. A pale blue light glows from the top of the mast. Then everything goes white as the sky’s wrath comes down.

You close your eyes and hold the wheel as strike after strike comes crashing down. The mast groans and topples over, then more and more of your precious ship is blasted apart by lightning. Then one bolt touches off the gunpowder, and the last thing you hear is a deep bellow of rage and loss.

You are Squadron Leader Cross Winds, and today is a good day. The intel on the movements of the Firestorm Pirates was spot on, and the storm is making quick work of their ship. You start to give the orders to breaking up the clouds, but then you hear a deep, distinctly male voice roar. Your heart drops. There was a stallion on that ship? Was he a hostage, crew, stowaway? You dive through the clouds and pull up at what you see. What parts lightning blasted away are now restored in pale green fire. The Shameless Sloop’s cannons turn of their own accord, rising-
“Evasive maneuvers!”

Your squadron scatters as the skies erupt with ghostly fireballs. You punch through the cloud and streak back to the rendezvous point. You aren’t looking forward to explaining this to your superiors.

You are somehow the very alive Captain Bad Apple. You come to as the last of the storm dissipates to the aft of the ship. Speaking of, it’s a bit different than you remember. You poke your hoof near the green wheel of flame that used to be the helm. It’s warm, but not hot.

“Oh, you’re up.”

You turn to see a translucent figure, some sort of minotaur bull?

“Ah, welcome aboard my ship?”

He grins.
“The other way around, actually. It’s so nice that you can finally see me.”
You blink.

“Are you the spirit of the Shameless Sloop?”

He shrugs.

“Insofar as I’ve been haunting it these past several decades, yes. So! Your crew's alive, the ship’s… working, what do you want to do next?”

You rub your face

“I need a drink.”

Anon laughs.

“Good choice.”

You head into the mess to find the rest of your crew had the same idea. Three Sheets grins at you.

“I see you met our good luck charm! I told you today was a lucky day, I don’t even have to do the rigging, he can do it all with a thought.”

You raise your eyebrows.

“I guess that means we don’t need you at all. That is some good luck.”

Sheets sticks her tongue out at you.

“Please, you’d be lost without my tits.”

Anon nods seriously.

“She makes a good point, her tits are pretty necessary.”

You facehoof.

"The spirit of the Shameless Sloop is a shameless slut."

"Can you blame me? I have had nothing to do for decades except ogle my crew and soothe their dreams."

Hard Tack blinks.

"So the reason why I always have face-sitting dreams while I'm on the ship…"

Anon grins.

"You're welcome."

The crew blushes, and you aren't immune either. You've had more than your fair share of dreams of trapping a stallion's head between your thighs and forcing him to eat you out. You walk to the opened case of rum and grab yourself a bottle. As you sit down, Keg sidles up to you.

"Cap'n, something's bothering me…"

You look at her questioningly. She runs her hoof through her short-cropped mane.

"I was right next to the barrels when they blew, Cap'n. By all rights, I should be a sticky coat of paint, not talkin' to you whole and hearty."

You swallow a mouthful of rum, but that does little to ease your mind.

"Might be best to avoid anything strenuous, then. At least until we see how this all shakes out."

Keg nods and knocks back the rest of her drink. She ambles over to the case and- Wait, shouldn't it be half empty by now? Keg grabs a bottle, and you stare as another one takes its place with a shimmer of faint green light. You take a sip of your rum, rolling it around on your tongue. It’s a good apple rum, not unlike what your estranged family would brew. No strange aftertastes, no trace that it might not be all that it seems. You turn your attention to Anon and Sheets as they flirt openly. Sheets has her arm around the ghost, pressing his face into the side of her teat. You can’t see where Anon’s hands are, but the blush Sheets is sporting gives you some idea. You clear your throat. Sheets snaps to attention, and Anon pouts.

“Anon, how much longer can you keep the ship whole like this?”

He scratches his chin.

“A while? I can feel a bit of strain keeping it together, but it’s pretty light even after a half a day.”

You nod.

“Even so, our top priority is stopping to make repairs. The nearest port is…”

You try to remember the map. Anon’s eyes unfocus.

“Trampa Bay, should take us about a day and a half to get there. Course set.”

The Shameless Sloop groans as it adjusts its heading. You blink. Sheets might not be the only one out of a job.

“Right. Good. Um. Is there anything else we can do to keep your energy up?”

Even if you fix the ship, at least Keg would be in trouble if Anon wore himself out. Sheets pats you on the withers.
“We discussed it and decided that you should get first dibs, being the captain and all.”
You raise an eyebrow at her, then look at Anon. He’s blushing prettily.

“You have no idea how long I’ve wanted this.”

You lick your lips. Time to boldly go where no mare has gone before.

“Let’s take this to my cabin.”

By the time the Sloop docks at the Trampa Bay harbor, you are glad you have such a hearty, vigorous crew. Anon doesn’t need to sleep, eat, or drink. More ominously, neither do the rest of you, though you still do so out of habit and for the joy of it. You walk down the gangplank and set hoof onto the dock.

And promptly stop, as your leg withers to the bone. You pull your leg back and are relieved to see it restored to pristine condition. It seems the sea has claimed you after all. You call out to one of the loitering wharf rats, paying her a piece of six to run a message to the lumber mill. You’re determined to make the best of it, and thinking back to the night before…

The best of it is pretty damn good.

You are Princess Luna, reading yet another report about the activities of the Shameless Sloop. Waylaying vessels for delicacies and booze, yet only stealing a trivial amount of the ship’s stock. Disappearing below the waves whenever a patrol comes by. Floating above cannon and spellfire range, making obnoxiously loud sex noises throughout the night. You sigh and set the report aside. With any luck, Celestia and her galleon full of desserts will persuade them to turn privateer. If you are going to have an immortal band of eccentric pirates roaming the seas, they may as well be on your side.

First Person POV

I am Captain Bad Apple, airing out my cot AGAIN. I still don’t understand why my morning dew is so much heavier on the Sloop than on the shore. I better not have an unawakened fetish for ships or the waves. That’s how the sea claims mares, I am pretty sure. I open my cabin and trot out onto the deck. Three Sheets is already up in the rigging, the tauress’ teats gently undulating in the wind.

“Morning, Captain! It’s going to be a lucky day, I can feel it in my nips!”

I roll my eyes.

“You said the same thing the day we got chased out of Port Outsbutt.”

Three Sheets grins.

“And I was right, I got to buck the governess’ son before we had to leave.”

“Which is why we had to leave. Get chummy and you’ll be chum, got it?”

She salutes.

“Aye Aye cap’n!”

I sigh and head to the mess. Hard Tack ladles me a bowl of oatmeal and dried berries. I nod my thanks to the unicorn mare. As I dig in, I ask,

“How are we doing on rations?”

Tack sits back on her thick flanks, rubbing her chin in thought.

“We’re good for about two months, longer if you let me bake biscuits.”

I nod, that’s about what I figured.

“We should be making port before then. And do I really need to tell you not to bake again?”

She frowns.

“I think I figured out where I went wrong, if Keg would just let me use her flour stock…”

I shake my head.

“Experiment with your own bits. We don’t need culinary armor plates right now.”

Hard Tack sighs and goes back to stirring the pot of oatmeal. I finish my bowl and leave it in the bucket to soak. Powder Keg wanders in, and I still can’t get over her appearance. Built like a Canterlot noble, tall and slim, but her tail cut indecently short and yet still singed at the ends. I tune out their bickering as I head to the back of the Shameless Sloop. I haul the anchor up, grinning as I bring all of my earth pony strength to bear on the winch wheel. It’s always a relief to really exert myself in something and not risk bucking a hole in my ship. I slow down as the water bulges under the chain and the anchor begins to break the surface. When it is fully out, I pull the brake on the winch and trot up to mare the helm. Sheets gives me a nod, and I call out mostly for the sake of the other two of my crew.

“Unfurl the main and head!”

Sheets undoes a few knots in her web of ropes and pulleys, and the two sails billow out and boom as they catch the wind. The Shameless Sloop jerks forward, plowing through the sea.
Let’s see what the new dawn holds.

A fussy merchant vessel, it would seem.

“Keg! Fire a warning shot across his bow!”

The unicorn grins, her horn lighting with a baleful red. The cannon thunders as it launches the iron ball, just barely clipping the rails of the merchant ship. A moment later, they answer with a shot aimed at my deck. I gallop to where it would hit and pivot, leaning forward. My hind legs bunch up, hooves close together and waiting for… With a metallic clang, the cannonball hits my hooves just as I buck, sending it back into side of the merchant vessel.

“Keg, clear their deck!”

A dozen clay pots arc across the water and shatter across the barque’s deck, covering it in a haze of flour dust. Then Keg’s fuses run down and fire blooms. Not much later, the merchant runs a white flag, and I bring the Sloop alongside and swing across. I land on a sooty wasteland, still warm and embers glowing along the edges. The stench of burned fur fills the air, but I ignore it and the groans of the injured as I approach the grim-faced captain. I come to a stop before her, my hardtack vest clattering dully.

“I’m glad you have come to see reason. Now, let’s see your cargo.”

The captain nods and trots down below decks. I follow her down, keeping an eye out for any-

The wall by the stairs splinters as a bullet bursts through it and shatters a hardtack plate on my side before clattering to the floor. I grunt at the impact, then buck the wall down. Among the splinters and shards of wood, I find a dazed mare, barely grown from a filly into a mare. I kick the pistol away from her and glance at the captain, who has grown quite pale.

“Mercy, good pirate. Please...spare my daughter, this is her first encounter on the high seas.”

I take another look at the fallen mare, and I can see the resemblance. I frown.

“She broke your flag of truce, I should make an example of her to keep such underhanded dealings at bay.”

The captain begins to sweat. I look her in the eye.

“You are a mare of honor, are you not?”

She swallows.

“I am.”

I nod.

“Give the filly a good birching, once I leave. And we’ll be taking your entire stock of flour, among other things.”

That should make Tack happy. The captain untenses.

“I’ll see it done myself.”

I nod and start sniffing around the cargo hold.

The haul is decent, a few cases of rum, plenty of spices, a gilded jewelry box, and some useful maps. Most of their hold is full of iron ore, which I leave alone. Still, nothing that would qualify for Sheet’s forecast of Discord’s Luck. Leagues later, the smell of flour being tortured into ceramic fills the air, and I am beginning to get nervous. The next trade route I want to hit is still a day’s travel away, with nothing but the open ocean between me and it. I glance up at Three Sheets. She’s wrapping her teats down, a grim expression on her face.

“Cap’n, I swear I didn’t buck anypony’s son this time. Clouds starboard, and I bet my last bit that they aren’t natural.”

I turn to stare at the horizon, and the dark cloudbank looming, small black specks flitting around it. My heart drops. I had thought I was keeping things low-key, hitting small targets and keeping on the move. But it seems the Crown has decided to nip me in the bud.

“Trim the sails! Batten down the hatches!”

I grip the wheel grimly. A normal storm, I could heave to and ride out. A Pegasus-driven one…

This may be the end for me and the Shameless Sloop. The winds rise, whipping the brine into the air. A great hiss fills the air as rain sheets into the rolling sea. I steer as best I can, angling into the wind. The rain splatters against me, instantly soaking me to the bone. Thunder begins to roll as the Royal Airforce builds up charge. A pale blue light glows from the top of the mast. Then everything goes white as the sky’s wrath comes down.

I close my eyes and hold the wheel as strike after strike comes crashing down. The mast groans and topples over, then more and more of my precious ship is blasted apart by lightning. Then one bolt touches off the gunpowder, and the last thing I hear is a deep bellow of rage and loss.

I am Squadron Leader Cross Winds, and today is a good day. The intel on the movements of the Firestorm Pirates was spot on, and the storm is making quick work of their ship. I start to give the orders to breaking up the clouds, but then I hear a deep, distinctly male voice roar. My heart drops. There was a stallion on that ship? Was he a hostage, crew, stowaway? I dive through the clouds and pull up at what I see. What parts lightning blasted away are now restored in pale green fire. The Shameless Sloop’s cannons turn of their own accord, rising-
“Evasive maneuvers!”

My squadron scatters as the skies erupt with ghostly fireballs. I punch through the cloud and streak back to the rendezvous point. I’m not looking forward to explaining this to my superiors.

I am somehow the very alive Captain Bad Apple. I come to as the last of the storm dissipates to the aft of the ship. Speaking of, it’s a bit different than I remember. I poke my hoof near the green wheel of flame that used to be the helm. It’s warm, but not hot.

“Oh, you’re up.”

I turn to see a translucent figure, some sort of minotaur bull?

“Ah, welcome aboard my ship?”

He grins.
“The other way around, actually. It’s so nice that you can finally see me.”
I blink.

“Are you the spirit of the Shameless Sloop?”

He shrugs.

“Insofar as I’ve been haunting it these past several decades, yes. So! Your crew’s alive, the ship’s… working, what do you want to do next?”

I rub my face

“I need a drink.”

Anon laughs.

“Good choice.”

I head into the mess to find the rest of my crew had the same idea. Three Sheets grins at me.

“I see you met our good luck charm! I told you today was a lucky day, I don’t even have to do the rigging, he can do it all with a thought.”

I raise my eyebrows.

“I guess that means we don’t need you at all. That is some good luck.”

Sheets sticks her tongue out at me.

“Please, you’d be lost without my tits.”

Anon nods seriously.

“She makes a good point, her tits are pretty necessary.”

I facehoof.

"The spirit of the Shameless Sloop is a shameless slut."

"Can you blame me? I have had nothing to do for decades except ogle my crew and soothe their dreams."

Hard Tack blinks.

"So the reason why I always have face-sitting dreams while I'm on the ship…"

Anon grins.

"You're welcome."

The crew blushes, and I’m not immune either. I've had more than my fair share of dreams of trapping a stallion's head between my thighs and forcing him to eat me out. I walk to the opened case of rum and grab myself a bottle. As I sit down, Keg sidles up to me.

"Cap'n, something's bothering me…"

I look at her questioningly. She runs her hoof through her short-cropped mane.

"I was right next to the barrels when they blew, Cap'n. By all rights, I should be a sticky coat of paint, not talkin' to you whole and hearty."

I swallow a mouthful of rum, but that does little to ease my mind.

"Might be best to avoid anything strenuous, then. At least until we see how this all shakes out."

Keg nods and knocks back the rest of her drink. She ambles over to the case and- Wait, shouldn't it be half empty by now? Keg grabs a bottle, and I stare as another one takes its place with a shimmer of faint green light. I take a sip of my rum, rolling it around on my tongue. It’s a good apple rum, not unlike what my estranged family would brew. No strange aftertastes, no trace that it might not be all that it seems. I turn my attention to Anon and Sheets as they flirt openly. Sheets has her arm around the ghost, pressing his face into the side of her teat. I can’t see where Anon’s hands are, but the blush Sheets is sporting gives me some idea. I clear my throat. Sheets snaps to attention, and Anon pouts.

“Anon, how much longer can you keep the ship whole like this?”

He scratches his chin.

“A while? I can feel a bit of strain keeping it together, but it’s pretty light even after a half a day.”

I nod.

“Even so, our top priority is stopping to make repairs. The nearest port is…”

I try to remember the map. Anon’s eyes unfocus.

“Trampa Bay, should take us about a day and a half to get there. Course set.”

The Shameless Sloop groans as it adjusts its heading. I blink. Sheets might not be the only one out of a job.

“Right. Good. Um. Is there anything else we can do to keep your energy up?”

Even if we fix the ship, at least Keg would be in trouble if Anon wore himself out. Sheets pats me on the withers.
“We discussed it and decided that you should get first dibs, being the captain and all.”
I raise an eyebrow at her, then look at Anon. He’s blushing prettily.

“You have no idea how long I’ve wanted this.”

I lick my lips. Time to boldly go where no mare has gone before.

“Let’s take this to my cabin.”

By the time the Sloop docks at the Trampa Bay harbor, I am glad I have such a hearty, vigorous crew. Anon doesn’t need to sleep, eat, or drink. More ominously, neither do the rest of us, though I still do so out of habit and for the joy of it. I walk down the gangplank and set hoof onto the dock.

And promptly stop, as my leg withers to the bone. I pull my leg back and are relieved to see it restored to pristine condition. It seems the sea has claimed me after all. I call out to one of the loitering wharf rats, paying her a piece of six to run a message to the lumber mill. I’m determined to make the best of it, and thinking back to the night before…

The best of it is pretty damn good.

I am Princess Luna, reading yet another report about the activities of the Shameless Sloop. Waylaying vessels for delicacies and booze, yet only stealing a trivial amount of the ship’s stock. Disappearing below the waves whenever a patrol comes by. Floating above cannon and spellfire range, making obnoxiously loud sex noises throughout the night. I sigh and set the report aside. With any luck, Celestia and her galleon full of desserts will persuade them to turn privateer. If I am going to have an immortal band of eccentric pirates roaming the seas, they may as well be on my side.