Cutlass Trifecta

“What,” The captain says flatly.
>“Th-The sail got torn up by the winds last night. And the Accompass is sick, so we really can’t sail too far anyways.”
Cutlass sighs heavily. She has just woken up and already she’s greeted with bad news. Ever since she finished aiding the Gates of Justice in establishing a new base, it’s been one disaster after another. Weeks passed as she tried to track down a new lead to chase, days for them to get supplied, and then even more when their Accompass got uppity and needed to be reminded of their place. And if that wasn’t bad enough, every day the ship seems to have another piece break or fall off.
“Get back to your station.”
Cutlass commands exhaustfully. The unicorn nods, leaving the captain’s quarters.
“Is there no competent crew out there?”
She complains to her empty cabin before she pulls herself up from her chair and exits to check the damage. Cutlass steps on deck, looking up to the sail in tatters. A pegasus hovers by it, assessing the damage.
“*Why* haven’t you replaced this yet?”
Cutlass scolds the pegasus, eliciting a cringe as he’s called out.
>“We’re, uh. We’re having some difficulties with the spare.”
“What kind of difficulties?”
The pegasus points down to the bow of the ship, keeping his distance in the air. Following his gesture, a burly earth pony is standing over a large mess of cloth, seemingly at work.
[Just one crew that can do things by themselves. Is that too much to ask?]
She thinks to herself, regretting these so called “pirates” she hoof-picked. Her dress stirs lightly, not that she notices. Cutlass marches over to the earth pony, sternly tapping her hoof on the deck while waiting for him to explain herself. The pony takes a second, lost in his work before he looks back at her.
>“Oh! Captain! No worries, this will all be done in two shakes.”
“And why does a simple task as setting up a sail need to take ‘two shakes’?”
>“Well you see, the cloth we bought isn’t quite… assembled.”
Cutlass holds a hoof to her temple.
“And by that you mean?”
>“What we thought was a sail sized piece of cloth, turned out to be a sail’s worth of cloth. In pieces.”
Cutlass says nothing, a saint’s level of patience keeping it so she’s only glaring daggers on the unfortunate crewpony before her. Her dress stirs again, unnoticed as it shifts slightly. It rises ever so slightly as an end frill curves inward.
>”And we’ve only just found out this morn’ when we went to replace the old one.”
Sensing Cutlass’ heightened stress, the dress takes prerogative to relieve her of it as the frill rolls up into a rod.
>”So I just need to stitch all these together, and we’ll be right as rain.”
Cutlass stomps her hoof, an infuriated huff of air exits her nostrils like a bull ready to charge.
“Of ALL the simple tasks, nopony here made sure we had a SPARE SAIL! How do you even screw up and buy scraps of cloth to begin with?! I WANT TO KNOW EXACTLY WHO WA—AAHHH!”
Cutlass’ muzzle snaps shut to stop the nearly embarrassing moan in her tirade.
[Wh-What was th—]
Her thoughts are cut short as again something pumps into her nethers, her mouth keeping any further sounds from escaping.
>”It’s quite a mystery, I know. But I got it covered.”
The pony’s words fall on deaf ears, Cutlass’ rage completely subsided by this invasion.
The dress, hidden from sight and unknown to its wearer, gently strokes the makeshift appendage into Cutlass. Sexual release being the quickest way to relieve a near unending amount of stress, and no mess to worry about from its enchantment.
[Would any of them dare to sneak in and… and. No, even in my deepest sleep I would’ve felt *that*.]
Her thoughts run rapidly, almost as quick as her breaths as she tries to keep herself composed.
>”Uh, Captain, ma’am?”
“Wha. Ahem, What?” Cutlass responds, correcting herself with a proper stern tone.
>”You’re looking a tad flushed. Are you feeling alright?”
“I’m perfectly fi-AII-ne. Fine. I’m just tired of having to deal with incompetent ponies like you.”
She scolds, nearly losing her image from a rather deep thrust.
“Finish this up quickly, since we’ll need to to stop at the next island to fix two mistakes.”
>”Er, two?”
“The sail, and whoever bought this mess.”
Cutlass says with venom, causing the pony to gulp in fear. She turns away, pride and ego heightened she still was able to intimidate with her unfortunate assault, and quickly cut away as a soft “Ah” leaks from her lips as her guard lowers.
[I have to get to my quarters and check on this.]
She slides a dagger down her sleeve, looking at her reflection and blush-filled face.
[A captain shouldn’t be leaving themselves exposed like this.]
Cutlass walks back across the deck, slowly to keep her steps from exacerbating the unrelenting sensations pulsing through her. She holds her head up, keeping a determined and regal stance to appear she’s giving a look over as she returns so soon to her room. The dress, sensing her resistance and a new rising of confusing stress, aids her relief as the frill decides to loosen up. It quickly unrolls and hardens stiff, spreading out while inside her to form a larger shaft to please her better.
“Mmmmf~”
Cutlass quickly bites her lip, keeping her moans to herself as best she can as she freezes. She quickly denies how good that felt, legs growing wobbly as this thicker foreign object takes her. She notices eyes starting to fall on her, looks of concern and confusion. Panicking, she looks up at the sail, pointing to it and then to 3 pegasi and a gryphon.
“You, you, you, and you. Since somepony on this ship failed with the sail, you four will be our new movement. Step over to the mast.”
She turns, spotting the unicorn that delivered the unfortunate news earlier. She points him out as well.
“And you, get over there and join them.”
Looks of dread, and mild annoyance, befall the five as they assemble.
“You will hold these remain taught with your magic, and hold any hole together as well as you can,” She directs to the unicorn, “While the rest of you use your wings to blow the sails so we can make up lost time.”
>”Aye aye, Captain.”
They say as they start to head to their positions.
The quick panic, while smart thinking, only alerted the dress more. So much stress, so much worry. It must be dealt with immediately! The dress extends the coil, giving it a deep reach as it rapidly pounds Cutlass.
Cutlass, relieved at her quick thinking, quickly tenses up, back almos arching as she feels a deep railing from behind.
>”Aaaahhh—nnnnd! I will be keeping watch on all of you, t-to Mmmmm—ake sure you won’t be slacking!”
She decrees out in a rather unflattering stammer, her tone at least keeping any questions from arising.
Cutlass sighs, from pleasure and from annoyance at being stuck there on deck now. Her face is a deep red from the embarrassment, but she can’t help but shifting her stance to spread her hind legs further apart for her mysterious invader, thankfully such a movement is hidden by her dress. Her breaths grow rapid, mouth practically sealed shut with all her mental fortitude to keep her sounds of arousal at bay. The dress feels her body tense and squeeze down on it, nearing that final release. It complies, giving a quick success of pumps before retracting and fully thrusting into Cutlass as deep as it formed.
Cutlass’ eyes open wide, her horn lighting up as she forms a magic seal over her mouth to keep that last, body-shuddering moan from being heard by a single soul. It quickly dissipates, nopony having noticed. She exhales deeply, feeling much more relieved than she has been in a while. A new issue, however, sits in her mind. The juices of her experience soak her thigh, and she dares not to think of what it may look like on the boards hidden by her dress. She stands tall and firm, daring not to move until she is sure that all evidence of this evaporates.
[Whoever did this. I’m going to kill them.]

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A new day dawns, and Cutlass stands at the ship’s wheel, taking charge of the sailing. Telling the crew she’s leading this sorry bunch to quickly acquire a new sail, but her motive is truly to keep watch over her ship. Convinced that her incident on the previous day was caused by somepony’s Aura, she keeps watch over her entire crew. Now if something happens, she’ll see whose face gives themselves away.
The day passes along as normal, the sail slightly more patched up but still required the crew to assist with wind and guiding. Cutlass huffs as nothing new has occurred, annoyed that she has no information and her plan has not worked.

Her dress stirs. The stress relief was only momentary, her body reverting back to high tension only an hour later. The dress by itself is not nearly enough. This cannot do. The back of the dress spreads out, looking like its just being caught in the wind as it scans the area around Cutlass. It hovers just so off the ground until on stallion walk by, passing across the deck as a pony normally would but unfortunately too close to this predator. The dress snaps out and wraps around his back leg tightly. The stallion freezes, remembering the scene of the dress biting through a fishman months prior. Terror silences any gasp from his throat, prayers already being recited in his head as the dress pulls him back a few steps. Another fold of the dress grabs a foreleg, moving him behind Cutlass.as if he was a statue.

The stallion is stopped just behind Cutlass, standing by her hind legs parallel to her. He trembles, worried about what is going to happen. A third fold of the dress reaches up, moving under the stallion as he closes his eyes, expecting to be gutting. But the dress does not touch his stomach, it moves lower. His eyes open and he looks down as the cloth wraps around his shaft. He stands frozen in bewilderment, eyes glancing up to the unaware Cutlass who scans the lower deck. The dress strokes him, coaxing his member as it slowly grows under the fabric. The dress lifts up entirely, leaving Cutlass’ rear exposed. The stallion cannot see her bare body, but the other crewponies on the upper deck can, and look over in confusion. The confusion becomes entrancement as the dress begins to jerk off the stallion’s now risen erection. His worries are washed away easily, the dress’ attempts at stress relieving working on one pony at least. As drips of precum form on his tip, the dress tugs him forward, milking him intensely.

The dress points the stallion’s length at Cutlass’ nethers, with clear intent for a more personal interaction. However, the stallion has no where near the level of endurance to make such a trip. His member thobs against the cloth, coming to climax quickly to the sight of the upper deck crew. His seed dribbles down onto the deck, whatever remnants that spill onto the dress vanishing from its enchantment. One small strand has enough force behind it to land of Cutlass’ flank, causing her to look up to the sky. With the stallion drained and useless, the dress let’s go of the pony and drops back down as if nothing happened just before she turns back and sees her close company.
“You. If you’re going to invade my personal space, grab an umbrella. I felt some drops and I’m not getting soaked before we reach land.”
>”Y-Yes ma’am.”
The stallion stammers in a blissful daze, walking off to fetch cover. The rest of the crew quickly returns to their jobs before Cutlass notices their prying eyes too. Cutlass looks back forward on her ship, eyes burning with determination as she grips the wheel tightly.
[I can feel it. This perverted ony is close.]

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Luck has turned around. After two days of sailing, Cutlass’ ship came across a barrel-like submarine bobbing along on the waves with a crew of diamond dogs. Not only did they loot the sub’s spare sail for the times they need to surface and restock on air, but she also took a prisoner after hearing them yelp about their treasure being found out. Having a new focus for her displeasure has put her own personal hunt off as an afterthought, and such focus fills her mind as she descends the stairs to the brig.

Cutlass steps with measured movements, making sure each clop of her hooves an echo to fill the capture dog with dread. Even if it may no look it, she *knows* he’ll be begging and spilling information in minutes. She stops at the entrance to the single cell they have on the ship. The dog sits against the wall, his paws bound together and tied to the wall to keep him from moving. The dog look up as she approaches, giving her a defiant look. Cutlass looks silently at the prisoner, glaring down like an executioner to build and savor this moment. Her horn lights as she levitates the key up so she can enter the cell, relocking it behind her. Her horn lights again, a knife levitating out of her dress as she brandishes it slowly.
“What were you little dogs hunting. Treasure? Or just some bones to chew on?”
>”If yer lookin’ for a bone, I’ve got one for ye.”
The dog counters with a gravelly voice. A dagger quickly embeds in the wall by his side, shaving a tuft of fur off his stomach. His bravado quickly fades, something she enjoys greatly. Another dagger floats out from her dress.
“What was that? You were going to tell me about the treasure?”

The dress starts to stir. It can sense Cutlass relishing in her interrogation. Her mood is uplifted, her body relaxed, this dog is fixing so many things for her. This dog is key.
“Now if you tell us where you dogs were going, I might be lenient on your punishment. Otherwise, we’ll have to do it this the hard way.”
>”Then ye better get your blades ready, cause I ain’t speakin’”
“I was hoping you’d say that.”
Cutlass goes to approach the dog, but she can’t move.
“Huh?”
She tries again, but her dress has gone rigid. As much as she struggles, her limbs are fighting against steel. The dog gives a snicker are her show of futile movement, eliciting a growl from Cutlass. Just as she does, she rises up in the air.
“Wha—?”
The back of her dress forms into a perfect cone, holding Cutlass in a stand up in the air, her hind hooves dangling in the air under it, kicking away to try and steal her movement back.
“What’s going on?”
The cone warps as the edges of the dress curl, lifting up in arcs as it forms a tripod series of legs. The dress has shifted away heavily from the front of Cutlass, leaving her lower body exposed and open for the dog to view. The dog sits up, mood perked as his tongue lolls out at the show he has. Cutlass quickly tries to reach down with her hooves to hide her shame, but the dress keeps her from doing so.
“A-Avert your eyes this instant! Or else!”
She tries to pull daggers from her dress, but the cloth folds around them to keep them stored away.
>”If this be the ‘ard way, I’ll gladly take it.”
The dress walks forward, Cutlass swaying as she hangs in her dress like a doll as it carries her to the dog. Her magic flashes intensely as she tries to hold her dress still, but it has no effect or hold on the fabric. She is stopped just before the dog, a ribbon of fabric quickly swiping out at the dog. He gasps, looking down to expect blood, but the cut only causes his trousers to fall to shreds. His red rocket springs up, exposed to the air and causing Cutlass to gasp in disgust. One leg of her dress grabs the dog and tugs him to lay down, leaving him in a better position as it moves Cutlass to hover over it.

“NO! Nononononono, I will not let this filthy mutt touch me this way, not even by this dress!”
Cutlass shrieks defiantly, tugging on her dress with both her hooves and magic to no avail. A ribbon holds the dog’s member up and still, Cutlass’ body slowly lowering down towards it. She panics, bringing down the dagger she was floating onto her dress to try and cut it away, but the enchantment causes the blade to snap on impact. Her breath is rapid and heavy as she frantically tries to figure a way out as her hooves touch the ground. She tries to brace them to hold herself up with her own strength. It works, but the dress starts to actively push against her.
“I am not going to let this filth defile me!”
She declares with all her soul, surging all of her strength as she slowly pushes herself up away from the dog. She smirks as she wins against her dress, not even a genie’s magic will stop her. But then the back leg of the dress kicks out her legs. All that force slams her down, impaling her on the dog dick.
”GAAA-AHH!”
A shout of pain rumbles the cell from Cutlass, the dog matching it with a pleased howl as her body tenses around him.
>”This be the best prison I’ve ever had!”
He pants as the dress starts to lift Cutlass off him. Cutlass’ head hangs back, eyes looking down as the dress slams her back down again. A wave of pleasure flows through her body. A disgusting, vile, repulsive… good wave of pleasure. Her body is like a toy inside the dress, being pumped up and down like a fleshlight against her will. A moan escaped her lips, unable to fight against this desecration on her body. As much as she hates this mutt being forced inside her, but this sensation slowly grows and fights against her sensibilities. The ribbon loosens from the dog, swirling around Cutlass’ legs to spread them out. The thrusts slow as the dress’ supports hold and wrap around her legs to hold them out wide.

The dress returns to its normal pace. The ribbon rises up along her legs, caressing her thigh as it wraps around her waist. It circles her lightly, rubbing along her lower lips as it leans her body back.
“Oooh~”
She reluctantly coos. The dog repulses her, but the dress is treating her like a lady... almost. The rhythmic pounds, shifting almost to fit her body’s senses perfectly. Even adjusting to the rocking of the ship, it’s better than anything she could have imagined.
>”Ahhh, I be nearing me limit.”
She snaps from her fantasy at the horrific implication.
“Wait, no, you can’t!”
She shouts, unsure if she’s talking to her dress or the dog. Feeling the throbbing of the dog, the dress start to rock her body faster. It slowly slides her deeper and deeper.
“Aah, aah, n-n-ooo-aahh~!”
She protests between each thrust, feeling a building sense of dread that tenses her body. Feeling them both near their edge, the dress shifts Cutlass back up straight, rising her up almost of the dog’s tip before pulling her body down hard. The knot slams against her tunnel, squeezing against her entrance as the dress struggles to fit them together. A primal feeling floods Cutlass, something she never felt before as the bulb refuses to enter her. And finally, their bodies meet as it pops in.
“Aaaaahhhh!~”
>”Aaaawoooo!”
They howl in unison, their bodies brought to climax. The dog’s seed flows into Cutlass, the warmth filling her insides bringing her body to such a release of pleasure that only intensifies with each spurt. The only sounds on the cabin are their panting, the creaking of the ship, and the waves.
>”I think we might be ‘aving a deal for that treas—”
The dogs words, breaking their silence of afterglow, are silenced quickly as well. Cutlass looks down, the dress having reformed back to a cone and bisecting the dog across his stomach. Hoofsteps start to echo from the stairwell. Her magic grabs the dagger in the wall, flinging it towards the stairs in one solid motion as a thud and a yelp replace the sound of walking.
>”A-Alright Captain, I’ll make sure nopony interrupts your interrogation.”
A frightened voice responds, quickly scampering back up.

The dress finally loosens, its job done. Not expecting the support to vanish, Cutlass falls over onto her back. With the lack of blood flow, the knot and the lower half of the dog’s body flops onto the cell floor from under her, leaving her alone and freed again. She stares up at the ceiling, left to mentally process what happened to her.