Actions

Work Header

The Gentleman Pirate's secret weapon

Summary:

This is a story about Izzy grudgingly watching Stede get dressed. Which he enjoys just as much as you expect him to. But he's doing it!!! Mostly because Edward told him to. But turns out, it's not all bad.
...it's the ass. Izzy is an ass-man, he's finding. What a gorgeous little journey of personal discovery. And growth. Personal growth. Probably.

Notes:

(See the end of the work for notes.)

Work Text:

"How do you like this color on me?" Stede asked, eyeing himself critically in the floor length mirror. 

 

Izzy forced his eyes open. They'd fallen shut around the 13 shirt mark and he'd allowed himself a little rest. There was no telling how many more had passed since, but by the growing pile of clothes on the floor...probably a lot. 

 

"Izzy?" Stede insisted, already sounding annoyed at having to ask twice. 

 

Izzy pretended to give him a good looking over. The frilly sleeves were ridiculous, but Izzy was practically blind to them at this point. They didn't offend his eyes the way they used to. Which was probably a bad sign. A growing madness inside of him.

 

He couldn't say for sure that this was indeed a new outfit. It certainly looked like something he'd seen Stede in before. Fancy embroidery on some fabric that cost the price of a small horse. The golden color looking somewhere between sunshine and egg yolk. Impractical. Too lavish to garner respect from any self-respecting pirate. Utterly ridiculous.

 

He weighed his words carefully. He knew how Stede felt about honesty. Finally he settled on: "It's very you, Captain".

 

It seemed to placate Stede, who went back to doing his heroic poses in front of the mirror. 

 

"Yes, I think you're right." Stede said. 

 

He continued turning, admiring, chattering to himself about cuts and inseams and shirt-tail length. Izzy tuned him out. He was lying on Stede's settee, dirty boots hanging just far enough over the side that nobody was going to yell at him.

 

Izzy had his eyes half closed and let his gaze rest on Stede's ample bottom. 

 

It looked good in those tight trousers he liked to wear and was currently getting something of a workout. Stede posing, pushing it out, pulling it in, turning this way and that. It was a stark contrast to his usual demeanour. He was at ease on the ship, surrounded by his trusted crew. But there was always a sense of primness and properness. Like there was a little voice in his head telling him to behave a certain way at all times. Something eternally restless and ill-at ease.
But now? Now, there was a casual quality to his movement that set Izzy's imagination working overtime. Fluid. Loose. Pliable. 

 

It was mesmerizing. 

 

Stede may be a ridiculous human being and a sad excuse for a pirate. Fullstop. 


But the lower half of his body somewhat made up for the atrocities of the rest of him. Truly his best asset.

 

"Yes, this will do nicely" Stede finally decided and Izzy breathed an internal sigh of relief. He was comfortable and the view was ...decent, but he'd been there for hours. He ached to get back out on deck, get some air. Yell at the crew. Maybe sneak into his bunk and have a wank over Stede's arse. Good, solid pirate stuff.

 

Stede turned around and started fussing with yet another pile of clothes.  "Now for the trousers". he said, pulling out the first pair.

 

Izzy choked on air. He felt like he was having a mini heart-attack. Nobody had mentioned anything about trousers to him. Edward had dumped him in the Captain's Quarters, declaring it Izzy's duty as first mate to assist Stede in selecting a new outfit for some occasion or whatever the fuck.


Izzy had been despondent on principle, about being lent out like a toy to do the other captain's bidding. Indignant, when he realized what was going to be expected of him, which was watching Stede play dress-up. Of course he'd resigned himself to it in the end. As Edward had damn well known he would. 


Edward had meanwhile fucked off to wherever he felt he needed to be.


Around shirt five Izzy had concluded that "where he needed to be" was probably just "as far away from this spectacle as he could get". 
It seemed there was an end to Edwards burning passion for the fop after all, and it seemed to be trying on clothes. So he delegated that to his trusted first mate and gallivanted off, hanging with the crew, to return later when Stede was all finished.

 

Stede looked up, at Izzy gasping for air, and raised a questioning eyebrow. 

 

"I'm fine", wheezed Izzy. He wasn't.

 

Stede shrugged, unconcerned. He turned back to the clothes and selected the first pair of trousers. He held them up, admiring the embroidered details on the waistband. He ran a finger over the soft black material and nodded approvingly. 

 

Izzy watched wide eyed, as Stede put the clothes back down and started unlacing the trousers he was wearing. 


Time seemed to slow down, as Stede set about undressing.

 

He took off his shirt first. Carefully folding it and putting it down on a chair next to him. Izzy watched the muscles moving in his back, entranced despite himself. 


Now he turned to his trousers. 


He was facing away from Izzy and started pulling down the sky blue fabric to free the pale flesh underneath.


The reveal of Stede's buttocks set Izzy's heart racing again. He'd thought himself familiar with them. Had spent the better part of the afternoon watching the fabric pull over them, felt like he'd commited their very shape to memory. But now. Having seen the peach fuzz that covered the top, the way it fell away to leave perfectly smooth round globes, with just a hint of darker hair down the bottom.


Izzy wanted to run his hand over them. Wondered idly how firm they'd be under his calloused fingers. Wondered if Stede liked to be handled softly, or if he preferred a firmer hand. 


Stede bent over to pull the trousers all the way down and Izzy only just managed to bite back a groan. The way Stede lifted his arse, like he was presenting himself immediately sent blood rushing to Izzy's cock. 

 

God, he wanted to fuck that ass. 

 

The thought took him by surprise, but he couldn't deny it. Stede fucking Bonnet's fucking ass. God. Izzy's mouth felt as dry as a desert. His tongue flicked out in an attempt to moisten his bone-dry lips, but his mouth was parched. He was thirsting for the man in front of him. He was a dying man looking at a well sprung up in the sand before him. Stede was a bountiful green oasis in a sea of dunes. 

 

Stede paused where he was bent over and chuckled, realizing he'd neglected to take off his shoes. He fumbled with them now, giving Izzy a chance to look his fill.

 

The hardness in his trousers became increasingly pressing. And obvious as well. If Stede turned around, there was no way he wouldn't notice. 
Izzy grabbed one of the hideous couch cushions and strategically placed it over his lap. He briefly grabbed himself through his trousers, giving his dick a much needed bit of relief. But his eyes returned to Stede as if drawn by a magnet. He wanted to be able to replay this memory later, when he was alone. 

 

Stede had managed to wriggle his way out of his trousers and let out a breathless little sigh of relief that went straight to Izzy's dick. 

 


Stede picked up the black breeches and stepped into them. He was still facing away from Izzy, so Izzy didn't have to hide his disappointment at this wonder of the world disappearing from view again. It should be considered a crime to cover up something so beautiful, he privately felt. 


The trousers went up smoothly, hugging onto Stede's curves in a way that was even more indecent than his usual attire. 


Stede laced himself up, then started twirling and posing in front of the mirror again. 

 

Izzy hoped to god that nobody wanted an opinion from him, because his mouth still felt dry as the desert, he didn't think he could utter a single word. And anyway, none of the filth that was racing through his mind was an acceptable way to adress his captain. 

 

Stede thankfully seemed very taken with the trousers and didn't look to Izzy for input. His hand traced over the embroidery again, where it now sat snugly against his waist. "Very fine handiwork, indeed"

 

The next pair of trousers Stede picked up were a violent shade of light purple. 

 

He quickly divested himself of the black trousers, again gracing Izzy with the delight of his bare bottom. He stepped into the purple ones and started pulling them up.
It was slow going this time. Where the others had fit him like a glove, these ones proved to be more of a struggle. He eventually managed to pull them up his legs, with a lot of humming and hawwwing, but halfway up his arse, he had to admit defeat. 

 

Izzy started transfixed at the way the waistline of the trousers cinched the meat of Stede's buttocks, like a bar-wenches too-tight corset cinching her breasts. 

 

"Oh bother!" exclaimed Stede. Ever the gentleman, avoiding foul language even in the most dire circumstances. 


Izzy was fighting for his life behind his cushion, feeling like his cock was going to drill a hole through it at any second. 

 

"That's not going to do at all, is it?" Stede sighed. He hesitated. He was still turned away from Izzy. He heard, rather than saw, the embarassment wavering in Stede's voice. 


In the end, vanity lost out to despair.

 

"Do you think you could give me a hand? I seem to have got myself stuck" he said quietly. 

 

Izzy briefly considered just running away, jumping into the sea, swimming towards a better life, free of all this.

 

He didn't. Of course he didn't.  

 

"Aye, Captain" he said. Because what else could he say. 

 

Abandoning his cushion, he walked over to Stede, who was blessedly still looking away from him. 


In fact he seemed very determined to avoid meeting Izzy's eyes. 

 

Izzy meanwhile, had managed to tear his eyes away from Stede's bottom and was now faced with a new dilemma. 


It wasn't just Stede's buttocks that hadn't fit in the trousers. 


Stede's front now held the biggest dick Izzy had ever seen, standing from a nest of golden curls that was just visible below the waistline. He wasn't fully erect yet, but well on his way. 

 

Izzy froze. Speechless. No wonder the trousers had had to capitulate. That ass and that dick. And wasn't that just unfair, that nature had blessed this man with both.

 


Stede's hands were restless, they kept jerking towards his crotch like he wanted to cover himself up. But he must realize it was hopeless. 

 

Izzy watched with fascination, as the half-chub grew harder by the second. It made his mouth water.

 


Stede cleared his throat. "I seem to have gotten myself in a bit of a ...situation..." he said, trailing off uncertainly. 

 

"You certainly have, Captain" Izzy replied, smoothly. Wondering privately if he'd be able to look himself in the eye again, if he begged Stede to let him suck his cock. 


"That looks...painful?" he offered. 

 

Stede bit his lip and nodded. God. He looked positively virginal like this. Izzy wanted to ruin him. 

 

"I think the best course of action would be, if you let me help you...relax?" Izzy said. He had a very good idea of how that could be achieved. He wondered if Stede was thinking along the same lines. 

 

Stede was still biting his lip, god, it was all spit-slick and red now. Izzy was all too aware his own erection hadn't flagged. But there would be time for that later. 

 

Stede nodded at him and that was all the motivation Izzy needed to swiftly kneel in front of him. He looked up at Stede, his hand hovering over Stede's erection, wordlessly asking for permission. Stede gulped visibly and nodded again. 

 

Izzy couldn't help a little smirk. It took a stronger man than Bonnet to turn down having his dick sucked.


He braced himself on Stede's thighs for stability. Stede's dick bobbed in front of his face, mouth wateringly huge and full. He breathed on it and Stede let out a full body shudder, watching him through half-lidded eyes. 

 

Stede put a hand on Izzy's cheek, almost a caress. It took Izzy by surprise with the tenderness of it. It made his chest ache and to distract himself he put Stede's cock in his mouth and swirled his tongue over the tip. 


Stede mewled like a kitten, his hand on Izzy's cheek tightening into a pinch.


Izzy wasn't deterred. He took more of Stede's cock into his mouth and started gliding his mouth over as much of the length as he could reach. He tasted good. Clean. The nicest thing he'd had in his mouth in ages. He was careful to cover his teeth with his lips, wanted to make it good. He hollowed his cheeks and started sucking in earnest. When he started laving at the sensitive spot under the crown, Stede started babbling, begging Izzy to keep going, don't stop, oh god, don't stop! Both of his hands were on Izzy's head now, a twin iron grip twisting his hair. Pullling him closer. 

 

Izzy was gagging, spit dribbling from his mouth, mixing with Stede's precome. He pulled off to catch his breath, looking up at Stede like he'd never seen him before. 


He was surprised Stede was so hands on. Not that he'd thought much about how Stede would be in bed, but he would have expected something softer, more virginal. 


Stede was far from a blushing bride. He was breathing hard, his curls an unruly mess framing his face, his cheeks flushed, his mouth red from where he'd bitten his lips trying to remain quiet. 


Stede thumbed the wetness from Izzy's chin, trailed a wet finger down Izzy's neck, over the swallow tattoo. His hand camer to rest just below Izzy's jaw, tipping his head further up. Izzy strained his neck upwards, feeling like he was about to receive a benediction. 


Stede watched him with dark, hooded eyes. 


"Open up" he said and Izzy scrambled to obey. 


Stede fed Izzy his dick again. 


Izzy fell on it like a starved man, hollowing his cheeks immediately. 


Stede's hands returned to Izzy's hair, making sure he couldn't go far, then he started shallowly thrusting into Izzy's mouth again. It left Izzy ineffective, unable to get a rhythm going. But by the sounds Stede was making, this was working fine for him. His moans went right through Izzy, shaking him to his core. He didn't think he'd be so affected by this, but hearing how desperate he made Stede, the little noises he couldn't hold back, it made him feel powerful. 


He felt Stede's fingers move restlessly through his hair, trying so hard not to tear at it, not to hurt him, but losing the fight, tightening his fingers painfully in the throes of his passion, soothing the sting with gentler pats, when he could manage. 
His thrusts became more erratic and kept hitting the back of Izzy's throat.


Izzy scrabbled at the smooth fabric of Stede's trousers, struggling to find purchase. 


His hands snaked around Stede and wandered up. He pulled Stede in by the waistband that was still digging into his buttocks. He pulled it down and allowed himself to finally grab Stede's arse, digging his fingers into the supple skin. 


Stede yelped indignantly and subsequently lost his rhythm, allowing Izzy to catch his breath. He drew in sharp breaths through his nose and renewed his efforts on Stede's cock. He sucked on the sensitive cockhead and was rewarded with desperate mewls from Stede, who'd lost all pretense at coherence. He was mindless with it, desperately chasing his pleasure.


He could feel Stede's buttocks tensing under his fingers, every time he thrust forward. 


Stede's orgasm surprised them both. One minute he was thrusting into Izzy's mouth, the next he was filling it up with his come. 


Izzy did his best to swallow, but he could feel some dribbling down his chin.


He let Stede's softening dick slip out of his mouth and grabbed one of the cast off garments from the floor to wipe his face on.

 

He was sure Stede would have had Things To Say about that, but he seemed completely occupied with trying to get his breath back and to remain standing on his legs that didn't seem to want to hold him up anymore. 

 

Useless. 

 

Izzy rolled his eyes. He got up off the floor and steadied Stede with a hand on his waist. 

 

"Do you want to sit down, Captain?" he asked, ever the attentive first mate.


He couldn't help it if his tone was a bit crotchety, he was still hard as a rock with no signs that anything would be done about it. 

 

Stede nodded and let himself be led to the settee. 

 

The too-tight trousers were somewhat hindering his movement. Izzy took pity on him and pulled them fully down before pushing Stede to sit.
Stede made a noise of protest about having his bare ass on the couch, but he didn't fight it very hard either, so Izzy just shrugged and pulled them over his feet. 

 

Stede let himself sink into the rich fabric and watched Izzy. Izzy tried to walk with as much dignity as he could muster with his still raging hard-on, picking up the already soiled shirt, to give to Stede, so he could wipe himself down.

 

Izzy didn't like the glint in Stede's eyes.

 

But Stede didn't say any of his usual Stede-isms.


He just thanked Izzy for the cloth. 


After he'd wiped himself as close to clean as he could manage, he turned to Izzy.

 

"Thank you" he said, with a smile that still spoke of his fucked-out brain, because there was no sarcasm to it, just genuine delight at an orgasm received. 

 

Somehow the genuineness made Izzy more flustered than anything else Stede could have said. He could have called Izzy a filthy whore and it would have felt more natural than this...gentleness. He felt his face growing warm, like a damn teenager. 

 

Stede was quick to recover though and in no time at all, fixed him with a calculating look. 

 

"So, what's it going to be?" he asked and Izzy was completely lost. Until he noticed that Stede was very pointedly looking towards Izzy's crotch. 

 

He gulped. 

 

"Captain?!" he asked, alarmed. Not daring to let himself hope for anything.

 

Stede pursed his lips. He gave Izzy his best disappointed glare. 

 

"Don't play coy now, Izzy. Not after you've had my cock in your mouth", he said and yeah, god, he had, hadn't he. 

 

"What would you like?" Stede asked. 
And wasn't that a loaded question and a half. 

 

***

 

10 minutes later found them, still in the Captains' Quarters. 
They had moved back in front of the mirror. 
Stede was leaning his chest heavily on a plush footstool.
He had his legs under him and his arse was pushed out towards Izzy, who was kneeling behind him.

 

Izzy had spent the last minutes preparing him and was currently easily sliding three digits in and out of a babbling Stede's arse. 

 

His cock was pulsing in his trousers, at the thought of fucking this coveted ass. 

 

Stede's hole seemed to suck his fingers in, seemingly craving to be full, loathe to let him leave. He was so tight and hot for him.

 

Izzy added more oil and slid a fourth finger in.

 

It went easily.

 

Stede let his head hang and moaned into the fabric of the footstool.

 

He was deliciously vocal. Izzy thrilled at every little moan and whimper.

 

Couldn't wait to hear the kind of sounds he could get out of him, with his cock.

 

"Are you ready, Captain?" he asked, unable to stop himself from using the proper adress. 

 

Stede moaned louder. 

 

Izzy chuckled.

 

He removed his fingers from Stede's ass to a pitiful whine. 
He spread the rest of the oil on his own cock, giving himself a little squeeze. God, he'd been hard for so long. He needed to fuck something like *now*. 

 

Izzy lined himself up, the head of his cock resting just at Stede's entrance.
He felt drunk with how powerful he felt. 

 

"Tell me you want this" he said. 

 

Stede moaned again, pushing himself back against Izzy.

 

But Izzy wanted to hear him say it.


"Say it." he demanded. 

 

Stede was drawing in harsh breaths, he sounded just as wild as Izzy felt. He shuddered, pushing harder backwards, almost enough for Izzy to slip in. 

 

"Yes, god yes, do it. Fuck me!" he cried.

 

And Izzy was powerless to resist.

 

He snapped his hips forward, driving into Stede in one long slide, that had them both groaning. When he bottomed out, they both stopped breathing. The intensity of Stede's heat was almost unbearable.

 

He had no idea how he was going to last. 

 

Stede tried to breathe around the sudden fullness and felt like his lungs had shrunk, taking tiny breath after tiny breath until he'd managed to relax again somewhat.

 

Izzy held out as long as he could, but the pressure was too perfect. He slowly pulled out and slammed back in again. He grabbed Stede's hips and pulled him to meet his thrusts. 

 

Stede was screaming underneath him, babbling nonsensical phrases, repeating his name like a prayer, harder, god, yeah, right there, Izzy!!!

 

Izzy let one hand wander and found Stede's dick hard and leaking again already, slick with precome. When Izzy's hand closed around it, Stede threw his head back and jerked his hips forward, dislocating Izzy. 


Izzy chuckled and nudged Stede's legs further apart. He still had a firm grip on Stede and used it to guide Stede back down on him.


Izzy sank into Stede to the hilt. Stede moaned at being filled again, at Izzy's hand moving up and down his length again. His walls were fluttering with the effort of holding back his orgasm. 

 

Izzy himself felt like he was about to explode.

 

"Come for me" he commanded, needing Stede to let go.

 

Stede jerked in his hand, coating his own stomach and the footstool with his release. 


His orgasm milked Izzy's own release from him,  burying himself as deeply as he could until his softened cock slipped out of Stede's dripping hole.

 

Stede's arms gave out underneath him and he collapsed onto the footstool.


Izzy flopped down on top of him. 


They lay there panting, trying desperately to catch their breaths. 

 

"You're heavy!" Stede's voice was muffled from where his face was mashed against the footstool.


"Shut up." Izzy told him.


There was a brief moment of silence.


"..., Captain." Izzy added, unable to help himself.

 

Stede dissolved into helpless giggles. 

 

Notes:

-listen. I know this is all very "oh no, I got stuck in the washing machine, guess someone better fuck me so I can get unstuck" but sometimes!!!! sometimes the heart just wants what it wants, okay!!!!

also let's just pretend Stede can get it up twice in the span of half an hour, while we're at it.

The only regret I have about this, is that I don't think I used Stede's huge cock to it's full potential. But it's okay king, we see you and we're all big fans, I promise v.v