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Nautical November Masterlist - Complete
The Reader is on her way to Tortuga when her passenger ship is attacked. The fearsome Captain Dean Winchester steals her, and convinces his brother/first mate Sam that they should help take her to her destination… for a lusty price.
Part 1: Cannons in the Night
Part 2: Opening Introductions
Part 3: The Captain’s First Payment
Part 4: Hold Your Tongue
Part 5: When the Captain’s Away
Part 6: Halfway There
Part 7: Against the Mast
Part 8: Retaliation
Part 9: Like a Diamond
Part 10: Farewell
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No Cum November 2023
Supernatural Masterlist
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#pirate!au#supernatural#winchester x reader#pirate!winchester#captain!dean winchester#first mate!sam winchester#dean winchester smut#sam winchester smut#reader insert#nautical november 2024#series masterlist
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To Be Shipshape
The night was still young and in its youth came hope. For many, these hopes were for a good night, dinners, dates, excited outings and illicit dealings. For Dean Winchester, hope came as a new lead. As his Impala drifted into the nearby parking lot of the harbour, his tense jaw and tight grip refused to loosen. This could be the night, the night where his hopes were met too, the night where he found out what happened to the missing men of this country. It had been nearly two months now and eight disappearances, all men, all at night, all at seaside towns.
Someone joked that maybe it was some siren song that drew these men to the ocean; to let their bodies soak in the sea and taste its salt before they disappeared into the depths. In Dean’s line of work, something like that wasn’t a joke, it was a possibility. The engine of the Impala died at once as Dean stared at his target, the old ship that may have been the witness to it all, or the cause. Some said they saw an odd looking ship around the harbour, usually sailing away to disappear into the mist of the sea.
There was only one conclusion Dean could come to, ghost ship. The ship looked like it was out of time, a wooden behemoth that creaked as it slowly danced upon the waves. Its sails were rolled up, an anchor of a rusted chain planted into the ocean and ropes that tied the ship to the docks. It was ancient, it was imposing and as Dean stepped closer, getting the hint of sea salt and something else, warm and spicy, he had to admit, it was beautiful.
He glanced around, only the tides and the creaks of the ship were his companions at the docks. He had everything he needed and years of dealing with the supernatural to help, so he didn’t understand why he was taking so long to walk up the wooden steps, to let them groan underfoot and for him to board the ship. But it did, he stood there just taking it in. He had seen so many odd things on his journey but this ship, this odd slice of time that had thrown itself into the present, was definitely up there.
Dean ventured forward. He didn’t know if it was perhaps the night, the growing height or the Fates themselves, but the wind soon picked up. Suddenly, the howl of the winds and jangle of chain were newfound companions as Dean climbed up the steps and went aboard deck. To say it was like entering a new world was an understatement, this felt to be a new realm, with its own laws, the first of which came through its sway. Dean had been on ships before, hell unlike Sam he never used to even get sea sick. But he stumbled as he took the first step and realised just how much the ship was swaying.
For a second it felt as if the world was warping, as if to turn upside down and let the seas fall nowhere. But then the next second the sway came in the other direction and Dean stumbled again, struggling for footing until he clenched onto the bannister of the ship. It took a moment for him to be able to stand and then, it felt as if he would fall any minute, before he heard a voice.
“Ahoy mate. Can I help ya?” Dean wasn’t sure what surprised him most, the fact he heard a voice or the voice itself. It sounded sultry, deep, a strong accent that carried itself on the winds. Dean looked to see a man step out of the doorway that led below deck and couldn’t believe what he saw, for all intents and purposes, it was a pirate. He was a short lean man dressed to the nines in dark leather. A short head of hair swayed in the wind and the bearded man was rugged, an undershirt exposing a slither of a muscular chest and a pendant. Fingers were adorned in rings that glinted in moonlight. And as he stepped closer, there was a new smell, a different smell, that emanated from the man and almost caused Dean’s eyes to water. “Mate, are ya alright? Ya look like ya don’t even got yer sea legs.”
It was hard at first for Dean to understand what he meant until he realised he was still holding onto the side of the ship.
“Uh right uhh...Who are you?” What the hell are you was more like it. Was this some sort of renaissance fair thing? Why was Dean on a swaying ship talking to a pirate?
The pirate himself chuckled as if he could hear Dean’s thoughts.
“Captain Killian Jones,” Killian introduced as he gestured out to the ship. It creaked in response. “And this is me ship, now I’ll ask again, who are ya? And what are ya doin’ here?” Dean didn’t think he’d get caught this easily. When he saw nobody was around, he thought maybe this was some enchanted ghost ship, somehow taking people and he’d be in and out. But the Fates laughed through the whistle of the wind. Nothing was ever so simple.
“Dean.” He didn’t offer his hand to shake but instead stood up straighter as he glanced around at the deck. It wasn’t as if anybody else was coming up. “So...Who are you? What is this? Are you like part of some...I don’t know, some show or something?”
Killian chuckled.
Dean furrowed his brows.
“Show? Aye mate, the best show on earth,” started Killian with a cocky grin that showed off his pearly whites. “A show of the seven seas itself, pirates, treasure, gallivanting and shanties. It’s a sight to see mate.” He gave Dean a wink, causing him to be taken aback. “Why don’t I show ya?” Dean thought about it. Every sense in him told him to get off the ship, that he’d come back with Sam, Cas and figure this out. But he was sure this was the ship and the ship always got away. This was his chance. But he shook his head. It was too risky a chance.
“Thanks but I…” Dean started but his sentence died in a weakening drawl as Killian stepped forward and suddenly the scent was back, stronger than ever. Dean couldn’t quite place it, this foreign concoction that had him blink away watering eyes and stifle a cough with how strong it was. All he could get was a hint of leather and a taste of that same spicy scent that greeted him as he stepped closer to the ship. “I...Yeah sure, I have some questions.” Killian’s smile widened as his eyebrow raised in interest.
“Great mate, come with me! We’ll get this all sorted and get ya shipshape,” And the two of them were off. The winds whistled louder. The Fates laughed harder. All the while as Dean started his descent below deck, a gust of wind shut the door behind him.
As Dean Winchester delved into the depths of the ship, he felt himself being entombed by wood, shadow and those otherworldly scents. The different squeaks of the steps and the general feeling of descent told him that he was going down.
But every other sense was wholly distracted. All he could see was darkness and all he could smell were those mingling scents that loomed closer with every step down. It wasn’t until Dean’s eyes adjusted that he could see a soft glow emanating from a doorway deeper inside.
It danced and it was only a moment later Dean realised it appeared to be some sort of torchlight as he smelled the faint scent of flame. One last step and Dean found himself on the same footing as Killian and soon into the hallway of the ship where the air felt twice as heavy. It was almost like he had to push himself to move as Dean stifled a cough and waved his hand in front of his face.
Ugh that smell...Dean scrunched his nose as he tried to focus on breathing through his mouth, but that only made him cough more as he got smoke into his lungs. Killian chuckled as Dean coughed a couple more times.
“Ye aint used to the smell are ya? Don’t worry lad, you’ll get used to it,” commented Killian as he sauntered on forward. Dean could still barely see as he cleared his eyes but other people were down here too, all men and all dressed like pirates. He glanced over towards them, to see if any of them matched the missing people’s description, but it was hard to focus as the ship’s swaying felt far worse below deck.
At any rate, Dean was far too shocked at how none of these guys seemed to break character. All of them greeted him with thick piratelike accents and lingo, as if they weren’t just playing pirates, as if they were pirates.
“I don’t plan on staying long,” replied Dean as he narrowed his eyes towards Killian. He couldn’t see what the pirate’s reaction was, but he could somehow tell that the captain was still smiling. After the fifth or sixth pirate greeted him, Dean was thankful when he saw Killian open a door at the end of the hall.
“This is me quarters here,” Killian announced as he swung the door open and a blast of heat and scents jetted out the room. Dean didn’t get seasick, but this was all making him nauseous and he quickly stepped in and let himself fall back into a chair at the end of the desk, a hand kneading his temple as he tried to focus. “So mate...What can I do ya for?”
The door was closed and suddenly Killian was sitting at the other end of a long desk, adorned with maps and parchment, a dagger in the wood and loose gold coins strewn around. The office itself was slightly cramped, a collection of knick knacks that formed an odd fusion of living and working space. On one side of the quarters was bedding, an end table, and the next was an office, for a meeting of the minds, bookcases, plans on parchment, the scent of gold that had been won and gold to be found.
But that wasn’t the only scent that lingered in the quarters of Captain Killian Jones. It only took a few moments for Dean to feel sweat start to form on his brow. He pulled at his shirt and tried to hope that he could ignore the stifling heat. That he could handle, but what was more difficult was that smell, as persistent as a predator, it didn’t seem to worm its way towards Dean. He had been following it the entire time, as he looked towards Killian Jones, taking a deep sniff and realising that the smell was twice as intense in here, in the captain’s living quarters. He reminded himself to try and only breathe through his mouth.
“Okay so uh...Killian is it?” Dean blinked. For a man who had met archangels, the name still sounded ridiculous. Killian cocked an eyebrow.
“It can be whatever you want it to be mate,” the captain winked. Dean blinked again. “But for now, how about we stick with Captain, or if ya must, Captain Jones, seven seas I’ll even let ya have Captain Killian.” Dean rolled his eyes. Seriously? At this point, if it was just a guy playing a pirate then it’d be ten times worse, the idea of someone staying in-character for so long. The smell reminded Dean that there was no way he’d be able to sit in here for too long.
“Sure...Captain Killian,” said Dean, addressing the name with the same seriousness as a child’s nickname. “Didn’t mean to just wander onto your...ship.” The ship croaked in response. “But I need help with this...investigation I’m doing.”
For the first time Killian’s cocky demeanour vanished. His smile fell and the focus of his eyes seemed to be more threatening than amusing.
“An investigation, ya say? What kind of investigation lad?” He reached over for one of the coins on the table, starting to fiddle with it as his other hand drummed against the table. Killian took a cursory glance to the porthole where he saw nothing but the endless dark oceans of sky and sea.
“Just about a...crime I guess, someone said they saw a ship like yours nearby,” Dean paused to take a breath. Even breathing here felt slower with all the heat and (he took another sniff and frowned), musk. He frowned in disgust. “I’m not a lad by the way.” Killian’s amusement threatened to return.
“Aye? That so mate? Well ye see anyone who don’t even have their sea legs here is a lad, lad,” replied Killian. He began to spin the coin on the table and slamming it down after a few spins. Spin, slam, spin, slam, spin...and slam. Dean’s eyes were drawn to it in annoyance. “But mate I dunno if I can help ya, I’d have to see what night it was, who was the lookout-” Dean reached into his jacket and fished out a folded piece of paper. He threw it towards Killian’s side of the desk. The ship swayed again and Dean gripped his chair much to Killian’s amusement. He didn’t even try to hide his smirk as he took the paper.
“That’s the night the...crimes took place,” explained Dean. His jaw tensed as he studied Killian, still playing with that coin (spin, slam, spin, slam…), still clearly not caring about what the ship did or didn’t see. Or rather, what the crew did or didn’t do. “The crimes…” Dean blinked as the ship swayed again, he still wasn’t used to it and it made it even harder to focus as his stomach churned. He felt like his head was churning along with it, his next words lost to nausea.
“Crimes, crimes, ya keep goin’ on about crimes...Can I ask what exactly happened mate?” questioned Killian. “Help me…” Spin… “Help you lad.” Still spinning... Dean was growing more and more frustrated with that coin. It was like the longer Killian played with it, the more his eyes wandered over, just to glare at it, just to have to blink every time- SLAM. That happened. Dean inhaled and almost instantly regretted it as he resisted the urge to cough from all the musk around. Even hints of the scent, the salt and leather of it all was too much for him.
“Men-” started Dean. Spin…
“I tend to bed em,” interrupted Killian. SLAM. “What about em?” Spin…
“A lot of them have gone missing,” exclaimed Dean. “I just thought you might-” SLAM. God he hated that sound. “Might know anything-” Killian shrugged.
“I might mate, but I doubt it,” replied Killian. “Besides…” Spin… “Why’d I know anything about that sort of thing?”
“You’d know because your ship was nearby and could you stop playing with that damn coin?!” Dean snapped. The heat was unbearable. The smell was worse. The coin was the last straw. Killian stared back at Dean. “Look, either you know something or you don’t, but you should quit wasting my time.”
“Aye mate? Is something…” Spin… Killian smiled darkly. “Bothering ya?” SLAM. Dean just glared back.
“Yeah actually it is, can you just stop for a second and take this seriously?” said Dean. Spin...Dean swore to God that the coin was growing louder. It was going to drive him crazy.
“Tell me about em,” Killian purred. His voice had grown lower as he continued to play with the coin. He let it spin just a moment longer before- SLAM. It was Dean’s turn to raise an eyebrow. Killian chuckled lowly. “Tell me about ya complaints lad.” Spin…
“What?” Dean wanted to ask more, namely what kind of joke was this? But he saw Killian’s expression darken and knew that in some odd way the pirate was being serious. “Fine, I’ll tell you. The smell, the musk, the chair is sticky, your coin is annoying and you-” SLAM…
“Are one of the hottest men you’ve seen,” interrupted Killian. “Is that right?” Dean scoffed.
“Yeah, you wish,” said Dean. Killian smirked. Spin…
“Then why are you hard mate?” Dean looked down and suddenly gasped. His eyes widened as he suddenly felt a presence in his pants, a presence he should’ve felt before. His dick was hard! But not just hard, but almost throbbing, that was until… “Or should I say...Throbbing lad.” SLAM!
Dean’s cock bounced for attention, suddenly throbbing as he panted and looked down at his member. He had never gotten so horny in his life, so hard, so desperate as his cock almost felt like a whole new limb, so solid as it bounced in his jeans. Sooner or later, he was going to get so hard it was going to start a tent against the worn denim.
Spin…
“F-Fuck! What? N-No…” Dean panted as he swallowed, his throat having suddenly felt dry. “This can’t be happening! What are you doing?!”
SLAM!
Dean grunted as his cock hardened even more and started to tent in his jeans. “No! No...Stop it!” Killian chuckled as he...
Spin…
“Oh too late to stop it mate, too late to stop…” SLAM! Dean bit back a groan. “Anything. It just…” Spin… “Feels so good to be…” SLAM! Dean couldn’t stop groaning then. “Controlled.” Spin… “To be…” SLAM! Dean moaned. “Mine lad...Cause that’s what you are...As you start to…” Spin… “Leak out all your thoughts.” Dean’s eyes widened as he felt himself fall back into the chair the more he tried to get up.
“No please dooooh-” SLAM! His cock throbbed again and began to sputter pre-cum, as Dean looked down, half-lidded and flushed.
“You were saying mate?” Killian teased. Spin… “Or were you too busy…” SLAM! Dean groaned out loud. “Leaking out your will out ya cock…” Spin… “And getting to obey Killian...Hook...Ya captain...As you…” SLAM! Dean moaned again. “Leak out for Captain Killian…” Spin…
“N-No-” Dean grabbed his cock hard with both hands, so hard he knew he wouldn’t even find it in himself to stroke. It wasn’t painful but he put enough pressure on his cock to squeeze out some more pre-cum and slow down any more from flowing. Uncomfortable enough that there was no way he could throb more.
“Oh, a fighter are ya? Well what if I…” SLAM! Dean grunted but kept his grip tighter. But he suddenly began to smell something as he heard leather shift and then plop. “Help with that…''
Killian suddenly put both his sweaty feet on the table, having taken his leather boots off behind the desk.
The musk hit Dean like a heatwave and his eyes stung from the sweaty salty musk.
But worst of all his grip loosened.
“No I-” Spin… “I can’t-” SLAM! “Give in…” Spin… “Can’t…”
“Resist?” Killian finished as Slam! The stain in Dean’s pants grew. His mind felt far away. All he could hear was Killian. “Can’t…” Spin… “Resist obeying ya captain?” SLAM! Dean groaned and to his shock it sounded like a groan of pleasure and approval. “Can’t resist…” Spin… “Staring at me feet?”
SLAM! Dean groaned and this time it was a groan of approval as his body instinctively humped the air and his half lidded eyes focused on Killian’s feet. Everything and anything from the sweaty soles to the musky scent to the wriggling toes, wriggling back...
SLAM! And forth…
Spin… Back…
SLAM! And forth…
Dean couldn’t even hear himself moan at this point because he just did it so easily, it was like breathing, he wouldn’t know until someone pointed it out. And Killian never pointed it out beyond a hand at his leather clad crotch and his signature smirk.
“Please…” Dean let out a weak moan, a whimper that sounded of pleading rather than resistance. He could barely think, barely understand what was happening. But he was still as strong as ever, and he knew he had to resist. He had to. He wanted to. He didn’t want to. He...Spin...Fuck….Not again anything but...
SLAM!
“Oghhh god-” He moaned and realise now his breaths were becoming pants, taking in more and more musk. The toes were still wriggling, still captivating, still so hot.
“Now mate…” Spin… “When my foot touches your face, you’re gonna just…” SLAM! Moan. “Sink! Understand mate?” Killian sat on his desk, the foot now beginning to raise and reach closer and closer as Dean moaned and whimpered and tried his bet to back away. But the seat didn’t budge and neither did he.
All he could do was crane his neck back as the foot got closer and closer.
“N-No...Stop…” The foot was half a foot away. “Please...Fuck…” Getting closer now, still wriggling, still spiralling. “Can’t…” The musky foot was inches now. “Can’t…” So close. “Can’t…” So big. “No…” So good. “I-”
The foot pressed against Dean’s face and with it he was under, sinking deeper and deeper in both his mind and the chair as he was forced to breathe in Killian’s musky foot. He even licked his lips, his tongue tasting some of the sole as Killian let the foot slowly descend down, toes brushing against his lips. It just went down and down and down like Dean’s mind, as the foot caressed his chest, his abs and then reached down until it rested right up against Dean’s denim clad throbbing cock. Dean whimpered and shifted slightly, grinding his cock against the sweaty foot as Killian just chuckled at him.
“Well mate, seems ya found me secret. But now it’s time to get ya...Shipshape,” Killian smiled down at Dean as he let his foot nudge gently against Dean’s member. “Everytime I click me fingers, you are going to slowly turn into more and more of a pirate lad.”
Dean’s brows furrowed, some part within him still fighting, still resisting.
“You are going to forget this whole thing happened and think we had a normal meeting in me office. But everytime I click me fingers, you are going to obey, going to become more and more of a pirate as part of me crew. You are going to forget your old life, ya old friends, that don’t matter now. What matters is ya crew and most importantly��”
Killian let his foot play with the wet slick head of Dean’s cock through his jeans.
“Ya captain.” Dean moaned lightly in agreement and let out a small nod. “Now how about I let ya…” He moved the foot up to Dean’s lips. “Have some fun…” He slipped the toes between Dean’s lips, smiling wider when Dean let out a muffled groan and took the toes in deeper.
“Before long it’ll be time to…”
Wake.
Dean shot up with a start, unfortunately taking long breaths as he tasted something salty on his tongue. He looked down at himself, seeing he was fine and then around at the room. The ship was still swaying and Captain Killian Jones was sat on the other end of his desk, feet up as he inspected one of his rings. He looked up, piercing blue eyes meeting Dean’s as he gave a weak smile.
“Good mornin’ mate,” Killian said jokingly as he saw Dean look around confused as the ship swayed again.
“The hell? What happened?” questioned Dean as his eyes locked onto Killian. For some reason that sickening sensation, that churning of the stomach, seemed slightly duller now. Killian gave no answers, only a smirk. Dean broke his gaze with Killian as he looked around.
Everything about this place seemed the same, the same disgusting odd scent, the same rickety aged interior, and the obnoxious charming captain at the helm of it all. Even behind a desk, it seemed as if he was in charge of the room, the conversation, perhaps even of Dean. From the way Killian Jones glanced at him, with a raised eyebrow and stupid stunning smile, Dean wagered the man knew it too.
“Nothin’ mate, we were just talking and you fell asleep is all, musta been real tired.” There was almost a mocking tone to Killian’s words, as his words wavered slightly like the surface of the sea. It was an odd way of talking, hell, the accent alone was an odd way of talking. But it did make Dean feel the need to listen. “So what were ya sayin’?”
What was Dean saying? He sighed and sat up in his seat, hearing his back click as he stretched out. He glanced down to his notebook, looking over some usual notes and some he barely remembered making, before a last stroke of the pen that slips off the page.
“Well mate?”
“Yeah I’m getting there,” exclaimed Dean as he looked up annoyedly at Killian. It frustrated him more how all the man could do was smile and take glee at the situation, as if he was incapable of taking anything seriously. Anything that wasn’t playing pirate anyway.
“Alright, alright mate just chop chop,” Snap. Snap. Killian snapped his fingers twice and with each snap, the sound echoed in Dean’s mind and for a moment he looked through Killian. He blinked as he felt something shift in him too. His feet suddenly felt colder as the socks around them were gone. The arches clicked and the toes sprawled forward as Dean’s already sizable feet grew a size larger. His once roomy brown leather boots now suddenly felt tight and cramped on his feet, causing him to groan lightly in pain as he peered down at his feet. But that was something he’d come to soon regret, as he smelled something musky emanating from beneath him. He wasn’t sure if it was somehow his feet, but as they continued to fill the shoes, they began to feel warm and sweaty. “Something the matter, mate?”
Dean looked back up.
“Uh no so uh…” He began to flick again through the notepad. “You’ve told me...Most everything but, like I was saying, has there been anything...Weird to you? Anything you’ve seen that’s just...Unnatural?” Dean narrows his eyes, watching Killian as they look away, seeming like they were suddenly deep in thought. There was nothing about this man that Dean could take seriously, the sooner he could get out of here, the better.
“Hmm, well there was something lad,” spoke Killian as he turned to look back at Dean. “Something...Bloody hell, I can’t remember uh…” Dean leaned forward with anticipation.
“What was it?” Dean questioned. “Look, anything, even the slightest thing can help.” Killian drummed his fingers on the desk, looking upward as he was trying to remember.
“Seven seas mate, it was on the tip of me tongue, it was…” Snap. Snap. Killian clicked his fingers twice as he tried to remember. Dean shifted in the seat as he suddenly felt his feet become less cramped. The shoes themselves changed, the leather beginning to ride up his ankles as it darkened all over. The shoes themselves turning into dark tall leather boots that were more than sizable enough to contain Dean’s larger musky feet. But the boots themselves stunk of it, making the scent even worse. Dean was about to look down before- “Oh! I remember mate!” Dean quickly looked up at Killian.
“Yeah? What?” Dean quickly asked, almost forgetting about checking out what was going on with his footwear and his feet. He tried his best to ignore that pungent musk filling the air but it was starting to get too much and he could already start to feel slightly light headed. But only slightly, as if he was getting used to the scent.
“One of me crewmates uh…” Snap. Dean grunted as his ass cheeks began to protrude. They grew rounder and softer, making him feel cushioned in the chair. He shifted in the seat, feeling like it had suddenly grown tighter on him as he swore he was an inch or two taller in the chair now. He glanced back to check why he felt so odd. “Derek I think it was, he saw something real strange mate and he...Mate? Hello?” Snap. Dean instantly looked back to Killian and let out a gasp as they felt their cock grow hard, suddenly throbbing as it made itself known as a bulge formed at Dean’s crotch.
“Huh? Wha-” Dean bit back a groan, biting his lip as he glanced down concernedly at his cock. Why was he getting so hard now? What the hell was going on with him? He could feel sweat beginning to form at his brow and only realised now that he hadn’t even been taking notes since he started asking Killian questions again. “Sorry, what?”
“You alright mate? You seem a little, I don’t know…” Snap. Dean gasped as his cock throbbed and he swore it seemed to grow an inch. At the very least this was the biggest boner he’d ever had. “Distracted mate.”
“Yeah, yeah look I think I gotta go I really-” Dean said as he was about to stand up.
“Oh no stay mate,” Killian purred. Dean shook his head, still halfway in his seat.
“No, I’ve really-” Snap. “Oh!” Dean fell back in the seat, moaning as he looked down to see his cock throb again, only this time he could see that it was starting to leak. His navy blue jeans were beginning to appear stained only...Wait, that wasn’t pre-cum, or at least it wasn’t just pre-cum.
It was something else, something darker...something shinier…
“Wha...What...What the fuck?!” Dean glanced down in shock and horror as he went to tug at his jeans, but they wouldn’t budge. His belt was nowhere to be seen and the button had all but disappeared. Killian sat back and watched the show unfold as he saw Dean desperately try to wriggle his way out of the jeans. But they wouldn’t budge, mainly because they weren’t jeans anymore. They were quickly darkening into tight black shiny leather pants, matching his boots and growing tighter. “No, no what the fuck is this?! What’s happening?!”
Dean’s breaths became pants, as his hand continued to try and pull at the tight leather, to drag it off of himself. But everything around him seemed so distracting. From the musk that permeated from his boots, to the ship that he swore swayed just when he almost got a good grip on the pants, to Captain Killian, sitting there and staring eagerly. But the worst came with his dick, his thick and sensitive length of arousal that he could feel was smeared by pre-cum that had no choice but to flow over and down his cock.
His breaths became gasps that became pants that became light groans of arousal, much of them snuffed out by this constant resistance that tried to stop his voice. Dean managed to hook a finger into the pants when...Snap.
“What’s wrong mate?” Killian smirked as he saw Dean look up with a shock and then look down at his pants. As if his legs were made of jelly, he could see them wobbling slightly, and feel them grow warm with the heat of change as he started to feel them stretch.
“No, no, no! What the…” Dean gasped and then groaned as he felt the first changes, his thighs growing just slightly wider, causing the leather to groan as it stretched out. “What the bloody hell have you-”
Dean covered his mouth, partly to stop the groaning but partly because...something sounded different. And he saw that Killian heard it too. The man raised an eyebrow and gave a smile that was of a welcome surprise before Dean moved his hand, trying to grab one of his legs, to see if his strong hands could stop the growth.
But his thighs widened with muscle, as if he was on his legs all day, every day. Dean knew his brother told him about the benefits of cardio, but he thought hunting was all the exercise he needed. Now his legs looked like he went running every other day.
“What’s wrong mate?” Killian chuckled. “Go ahead lad, speak.”
Snap.
Dean groaned and writhed in his chair as he looked down to see his own leather jacket was now starting to disappear. He knew the only one with a leather long coat was Killian...Captain Killian.
No, fuck! Not a damn captain! Dean thought to himself as he looked down, more preoccupied with what was happening to his shirt. His own shirt began to transform into some thin undershirt of cheap fabric, slowly lightening to a pale, almost ivory colour.
The sleeves grew slightly wider and were peppered with strings that crossed over. It looked to be one of those shirts some knight would wear on a medieval historical show. But a moment later Dean realised it was one of those undershirts from older times, only this one wasn’t a prop.
This one was real.
The neck hole was slightly larger and the opening of the shirt exposed some of his chest. Dean continued to grunt and groan, refusing to let these moans of pleasure escape easily. But most of all he didn’t dare speak, in fear he’d-
Snap.
“I said speak!”
“Fuck, I don’t…” Dean grunted as his lips moved all on their own. He tried to urge his hand to cover his mouth but he suddenly didn’t want to disobey Captain Killian. He couldn’t. Snap. “Fuck please man don’t-” Snap “Fuck m-m- mate!” Dean gasped as he could feel more and more of his southern American accent was fading, as more and more of his clothes did. The pen in hand turned into a quill. The notepad became sheets of parchment that fell to the floor. Everything about and around Dean was changing, growing perfect to be on a ship like this, to be…
Oh god, not that, Dean thought.
“Sounding a bit...Different lad?” Snap.
Dean watched as his chest began to itch. He groaned out loud as his pecs grew even larger, becoming two sizable pouches of muscle that jiggled as he writhed and gyrated his hips in the chair. His own cock was practically leaking out a fountain of pre-cum, so much so that some arrived in spurts with each-
Snap.
“F-Fuck mate, my- me voice...What the hell did you do to me...my fuckin’ voice!” Dean yelled as he looked down. He wanted to get up, but it was like his body was incapable, as if he was trapped in this very room, right where the captain was.
Fuck, he wish he could stop calling Captain Killian, captain.
But he couldn’t.
“Sounds like yer wantin’ to join our crew mate.” Snap. Killian chuckled darkly as he watched Dean struggle, looking down to see chest hair beginning to sprout out across his enlarged pecs. Dark blonde hairs that spread across his upper chest and down beneath his undershirt, tickling him as they grew and radiating more musk. “Come on mate…”
Snap.
“No please I’m not...Not some bloody- Oh fuck gotta...Gotta make this stop mate,” cried Dean as his arms began to balloon out with muscle. They widened, growing a couple inches thicker as all his tattoos along his chest disappeared, as if the chest hair itself rubbed it away. Dean could feel the changes racing up to his neck now, as his previously shaved jawline was beginning to grow hairy again. “I- I just fuckin’ shaved, ya can’t...Fuck me fuckin’ voice, please make it...Make it stop!” Dean’s voice wrestled between his grizzled deep southern voice and a more smooth and seductive British accent.
Words and knowledge of piracy, life on the sea, the different parts of a ship slowly started to make themselves apparent. They first appeared in Dean’s dialect, and then like ink on parchment, sank further into the material, drying there and making its place more permanent in his mind. Soon, the word starboard wasn’t just something he kept thinking about in his mind, but it was something he knew the meaning of, something his voice itched to use.
“Oh come on lad, just give in…” said Killian.
Snap.
“No please don’t fuckin’ do anythin’ you bloody-” Snap. Dean throbbed and writhed in the chair, cock throbbing as not much changed about his angelic face besides the beard that made him seem more grizzled. His body was done. It was his mind that was now the plaything.
“Just let go…” continued Killian.
“I’m not lettin’ go of anything you fuckin’-” Snap. Dean moaned and fell back in the chair, he was losing the battle of resistance. His cock felt so good, everything felt so good.
“Join me crew…” purred Captain Killian.
“No stop before...Me voice, no me fuckin’ voice what the bleedin’ hell have ya-” Snap.
“Ohhhhhh-” Dean moaned.
“And obey ya Captain…” declared Captain Killian.
“No...Please...Fuck I ain’t a bloody pirate, you can’t-” Dean saw Killian raise his fingers slowly. “Fuck mate! No! Don’t do it! Don’t make me some fuckin’ pirate! No! Don’t-” Snap.
“Come for ya captain,” commanded Captain Killian. And how could Dean disobey? The last of his mind slipped off that cliff of resistance and basked in a freefall towards lust, debauchery, chaos, a crew, a Captain.
His cock throbbed and then, the dam fell, with one last pump, he felt his cock shoot out jets of hot seed into his leather pants. He grabbed his cock, trying to stop it, but all it did was make it worse as he felt his leather clad member practically vibrate with how hard and fast it throbbed, almost fucking his hand as he came again, and again, and again. Dean’s eyes rolled into the back of his mind and fittingly saw nothing but darkness back there, as if he was staring directly at his brain to see it just cloaked by the shadows of musk and lust and obedience for Captain Killian.
Dean Winchester was no longer the Kansas born supernatural hunter. He was now Deacon of Winchester, one of the most handsomest pirates of the seven seas, a traveller and like much of the other crew, occasional lover to the one and only Captain Killian Jones.
After he came out of his senses, he came back to them as he woke up with a start in the captain’s quarters, his captain’s quarters.
“Bloody hell mate, what happened?” Dean Winchester, or as he was now known, Deacon of Winchester looked around. Captain Killian just smiled down at him.
“Looks like ya hit yer head mate, ya feelin’ shipshape?” Killian looked down at him with a smile and a look of expectancy. Dean Deacon didn’t know what he was doing in the captain’s quarters but he just smirked towards the captain.
“Right as rain mate,” shot back Deacon much to Captain Killian’s satisfaction.
“Well then, get back to it mate. That’s an order,” Captain Killian winked at Deacon, causing their smirk to widen. They stood up and gave a nod.
“As ya wish, Captain Killian,” replied Deacon and with that, he left the quarters feeling like a new man. He took in the deep scent of the sweat, musk and rum, the manly scent of a hardworking crew. All before he got back onto the deck of the ship, the sea around them and the salt in the air. Nothing felt better than being here, to be sailing on the open seas with his crew, his rum and his captain. It sure felt good to be a pirate.
This story was originally posted on my Patreon, but I've decided to release it for FREE. Click here to check out more stories like this on my Patreon and feel free to message me if you want to find out more or if you just enjoyed this story!
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the rest don't matter
a.k.a. an overly earnest entry for spncarfuckersweek
#supernatural#dean winchester#impala#a#thank u chevrolet car manual website that tried to make me pay $5 for a pdf but i didn't. i pirated the car. downloaded the car (photo)#SO!! i did NOT draw the car photo (obviously) or the car part diagram. they are stolen from the manual.#first of all i do not own a car i have never driven a car i do not have a drivers license#however. and this is vital. i am a carfucker purist.#also a boatfucker purist but that's beside the point#none of that human version of the car by curse stuff or whatever. that's weak. you have to want to fuck the actual car.#also enjoy this amount of art while it lasts i.e. while i'm still on holiday haha
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- what is wrong with you??
- uh.. idk, but whatever it is, it's their fault. pretty much.
#logan howlett#wolverine#x men#tony stark#iron man#tomoe#kamisama hajimemashita#dean winchester#supernatural#crowley#gregory house#house md#dr cox#scrubs#doctor who#ninth doctor#twelve doctor#jack sparrow#capitan jack sparrow#pirates of the caribbean
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pirate!au headcanons — sam winchester
cw : gn!reader, mild angst, fluff, enemies to lovers ish, kidnapping, weapons, violence, injury(?), fire, 1.1K words. requested !
prompt : royalty!sam x pirate-captain!reader
MOVED BLOGS TO @sammyluvr !! no longer active on this blog! all fics can be found there!
bonus!!! @mxltifxnd0m the requester, my sweet sweet wifey also made a gorgeous moodboard for this set of headcanons! feast your eyes <3
⟢ you’re not the type to take hostages; they’re a hassle for a multitude of reasons, plus you’re not too into making money by selling other people
⟢ but this one was just too easy, and promised too much money to turn down
⟢ not only that, but he looks quite good tied up to a beam in the spare storage room
⟢ “well, well. to what do i owe this pleasure, mr. samuel winchester? oh. i do apologize. duke samuel winchester.”
⟢ there’s a withering look in his eyes as he looks up at you, standing over him with your hands on your hips
⟢ “you tell me,” he retorts, indelicate and unphased by your sharp-edged sarcasm
⟢ you raise your eyebrows at him. “strong willed, are we? i thought you’d be all whiny and pathetic like your annoying royal counterparts. i suppose you might be entertaining to have around after all.”
⟢ quickly, he proves to be more than just that. within four hours of setting sail, he escapes his bondage and almost makes it away on an emergency boat
⟢ of course, you’ll have none of that; he knocks out half of your crew, but is no match against you
⟢ he fights well with a stolen sword, but you disarm him in seconds, then skillfully tackle and pin him to the ground
⟢ “where do you think you’re going, pretty boy?” you snarl into his ear, triumphant as you press a knee into his back to keep him down and tie his hands back
⟢ you brush off the help of your crew as you unceremoniously yank him to his feet and push him back into the storage room, muttering about the incompetence of the people around you
⟢ you retie him to the beam, sure that he’ll be unable to escape again after having done it yourself
⟢ even then, you keep a close eye on him; half to make up for the few blubbering fools on your crew you’re forced to keep for numbers, and half because he intrigues you
⟢ of course, you spend the most of your time keeping the ship orderly, robbing royal barges, and planning details of anything and everything in your private quarters
⟢ but you’ve started taking lunch in his dank storage room, finding pleasure in the way that he glares at you and makes scathing comments about how “you won’t get away with this”
⟢ you, of course, already have gotten away with it, but it’s still entertaining to hear him threaten you
⟢ certainly, you don’t express your entertainment; in fact, you hide it with a glower and near-silence
⟢ soon, sam changes tactics, and he asks questions about you, even flatters you a bit, trying to gain trust
⟢ you easily recognize the game he plays, but you play along. better to let him think that it’s working
⟢ you answer in short sentences, keeping at your mysterious and closed-off persona, but letting enough truth slip through that he can sense your honesty
⟢ it’s easy for you to tell how smart he is; the fact that he escaped so quickly that first day, the way he tries to play you, the exact questions that he asks and the calculated responses that he gives
⟢ that, and the way that he can tell his tactics aren’t actually working. better to let you think that he thinks they are
⟢ really, you both see right through each other with an odd sort of ease
⟢ you despise each other, you suppose, for the reason that you should
⟢ and you so strangely understand each other, the way that the both of you talk with such calculation and caution and intelligence
⟢ the words that you choose to use and the little truths that you let slip through tell you that you’re alike, that you’ve suffered and found refuge in some of the same sorts of things
⟢ what’s stranger is that sam feels this way even when you barely speak. you just sit there in silence most days, and yet, he reads you so easily
⟢ he wonders if you can read him just the same; thinks you can based on your gaze and the pointed, short questions that you ask
⟢ strangest is the way he wishes that you’d speak more often, maybe just to prove that not everything out of your mouth has to be scathing and cold
⟢ when the ship catches fire during a battle, sam discovers that while your words may be rough and mean, your actions are not always
⟢ he’s already coughing from the smoke seeping in from the crack under the door when you burst in, determined and silent
⟢ the flames spread and the crew rushes about, doing their best to douse the flames, but you’re untying his bonds and grabbing the collar of his shirt to push him out
⟢ you hand him a bucket, grab your own, and don’t say a word unless to shout orders as you work tirelessly with your crew to save the ship
⟢ sam does not make a run for it when he so easily could. sam helps
⟢ the damage was contained, and the ship can make it to the next port for repairs without problem, but sam’s room is unusable
⟢ the only empty space able to fit him is either your bedroom or your office, and either sound like torture to you
⟢ you tie him up in your small office, now forced to be extra careful to hide and store your documents and keep them out of sight when you use them
⟢ but you don’t tie him up quite as tight as before, and you take him on walks around the deck
⟢ you give him a cot and tie up his leg. he could get out of it if he wanted, with his skill, but he doesn't
⟢ then you untie his leg and let him eat at your desk across from you, and then you discuss plans and books and politics with him, and then you have him wrapped around your finger
⟢ you still pretend to hate each other, but he’s smart and resourceful and helps you with your plans
⟢ and you’re secretly more compassionate than most royalty he’s ever met, and you treat him fairly and respectfully once you realize he deserves it
⟢ he likes it on your ship and you like having him there, and one day when you threaten to tie him back up, he gives you a withering look like the first time he laid eyes on you
⟢ it takes less than a few moments for your lips to be on his and your hands tangled in his hair
⟢ his rough hands grip your waist and without question, he’s your second in command, your right hand man
#sam winchester x reader#sam winchester pirate au#sam winchester headcanon#sam winchester blurb#sam winchester drabble#sam winchester fanfiction#spn headcanon#sam winchester x gn!reader#supernatural headcanon#supernatural sam winchester#sam winchester fluff#sam winchester#spn sam winchester#supernatural#sam winchester x you#supernatural requests#supernatural fluff#supernatural fanfiction#sam winchester supernatural#supernatural x reader#spn fanfic
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One of my ideal destiel weddings happens mid-battle. Dean is dodging this week's monster, Cas at his back fighting something else equally as sinister. There is, yet again, another apocalypse looming over them. Team Free Will (2.0) is once again backed into a corner. They don't think they're making it out of this alive.
Between slashes of his weapon, Dean asks over the noise. "Cas, will you marry me?"
Cas almost gets himself stabbed, but he says. "Really? Here and now? Out of every opportunity we had?"
"Yes! There's no need to bitch about it. I love you, yada yada, some end of the world crap about not having any regrets before we die."
"I love you too." Cas' angel blade finally pierces the enemy's skin. "And yes, I would love to be your husband!"
"SAMMY!"
From across the room, or field, or road, Sam yelps over the sound of his own fight. "What?!"
"You went to law school, can you officiate for me and Cas?"
"That's not how it works, Dean!"
"Then fucking do it anyway!"
Y'know, like that one scene between Elizabeth and Will from Pirates of the Caribbean...
#supernatural#destiel#spn#castiel#dean winchester#sam winchester#destiel wedding#deancas#casdean#pirates of the caribbean
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Pirate!Dean has my god damn heart so I had to draw him 🥺
Based on the amazing fic Raise the Black by @valleydean 10/10 recommend 🫡
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feeling that ache deep inside remembering that the characters, books, movies, tv shows and stories i love so much are not real. that i love these characters as real people, with all my heart, but i will never get to know what it feels like to be loved by them, to be with them, because they do not know me.
i am a universe away from them yet somehow, i so deeply feel the absence in my life of people and stories who are not real
#stranger things#harry potter#percy jackson#star wars#lord of the rings#disney#friends#new girl#modern family#supernatural#the wizard of oz#marvel#mcu fandom#dc universe#the addams family#pirates of the caribbean#the office#that 70s show#once upon a time#max mayfield#ronald weasley#annabeth chase#general leia#frodo baggins#peter pan#chandler bing#nick miller#phil dunphy#dean winchester#wonder woman
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Me: What do you mean ? I don't have a type!
My favourite characters:
Energetic, charismatic, show-stealer, quirky sassy little shit but oh so lovely
Acts all confident and cocky, but deep down has severe self-worth issues
Daddy/mommy issues + childhood/past trauma
Rough around the edges but is actually a cinnamon roll
Badass, sexy and very, VERY QUEER
Messes up sometimes, but owns up their shit and actually manages to make things right
Seems like doesn't care but deep down is a big ol' softie
Loyal af, would take a bullet for their loved ones
Got a bit of darkness lurking around in there but always manage to come clean and do the right thing, got an AA graded moral compass there
Honourable mention: childhood crush
Me:.......oh, oh sHIT! :0
----
Edit: another childhood crush that I didn't even know was my crush but by God! Was I obsessed?
#yup i have major issues#doctor who#tenth doctor#supernatural#dean winchester#good omens#anthony j crowley#six of crows#jesper fahey#lucifer on netflix#lucifer morningstar#the bastard son & the devil himself#gabriel boutin#stranger things#steve harrington#chilling adventures of sabrina#nicholas scratch#disney tangled#eugene fitzherbert#pirates of the caribbean#captain jack sparrow
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Thinking about the line “Do it doggy style so we can both watch x files” from the sex song The Bad Touch and DeanCas cause ofc
Dean proposing that they have sex while they’re on the couch watching X Files and Cas agrees but goes to turn the tv off and Dean’s like, nah just fuck me from behind and we can keep watching. Cas giving Dean the ‘humans baffle me’ look. Dean retorting with “Look, I know it doesn’t make sense to you cause you have literally all the time in the world but I’ve only got another 40 years in me at best. Not enough time to get all the serial tv shows and carnal pleasure in that I have on my agenda. Besides, I might get dementia and not be able to understand X files if I wait and I know for a fact that my joints are not getting any younger. Now line up lover boy, Scully’s about to see something science can’t explain.”
#the brain worms#literally can’t help myself#go listen to The Bad Touch tho#it’s aged like fine wine#and is in fact THE sex song of all time#cw sex mention#x files#this is a little spicier than normal#but it’s all about the comedy#and also Cas not understanding mortality#Cas would pirate x files into heaven for dean#this is canon#but also they will fuck in heaven too#Dean knows this and is just ribbing him and has a thing for Mulder#spn#supernatural#dean winchester#destiel#castiel#deancas#casdean#destiel drabble#destiel ficlet
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A little fantasy of mine.
PirateAu! Trans Hunter Pirate!Dean meets is wildest dream catch:Mermaid!Cas, after a shipwreck.
#nonbinary artist#destiel#castiel is loved#destiehellers#destiel deserved better#deancas#destiel art#destiel fanart#castiel#dean winchester#Au pirate#mermaid cas#trans dean
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Redesign of Benny Lafitte, a vampire who once run with the Old Man and his crew before breaking off from them to have a normal life with the women of his dreams, now centuries later Benny walks around the earth to kill the Old Man Cabel and eventually the Old Man himself, and with the Help of his new human best friend Dean Winchester he just might get what he wants.
He is based on "Benny Lafitte" from Supernatural.
First Appearing in Supernatural, Season 8, "We Need To Talk About Kevin".
Tell me what you think of Him.
#supernatural#supernatural fanart#supernatural characters#spn#spn fanart#spn characters#benny lafitte#vampire#pirate#vampirates#the old man#dean winchester#redesign#art#earth-28
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benny lafitte (supernatural) the vampirate stimboard with blood, clothes & related stims!
ᯓ🧛🏻 x x x , x x x , x x x
#aka dean winchester’s vampire ex bf#vampire#pirate#clothes#black#red#slime#necklace#machete#cw blood#blood#bat#stimboard#stim#stim blog#stim account#stimblr#stims#gif#stim gif#supernatural#benny lafitte
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Nautical November Part 9: Like a Diamond
Captain Dean Winchester has never really agreed with his brother’s treatment of the Reader. With Tortuga just days away, he takes it upon himself to show her how a pirate’s paramour should be treated.
Pairing: Captain!Dean Winchester x Reader
Warnings/Promises: possessive!Dean, mention of last chapter’s blood, Fluffy Smut, body worship, oral (female receiving), overstimulation, p-in-v, creampie, Angst
Word Count: 4140
Note: This chapter operates under my assumption that if the Winchesters had been men of means, there is no way that Dean wouldn’t have absolutely spoiled whatever partner he was with. And if you catch the James Bond reference in this, kudos to you! Also, I may have hurt my own feelings with this chapter’s close. Happy reading!
Part 8: Retaliation
It was a few days before Dean noticed your new abrasions. When he did, he threatened to keel-haul his first mate.
“Blades are for battles and for defending ourselves. Not for carving up our passenger.”
Sam shrugged. “She’s alright, De. The cuts are healing nicely, and they won’t scar. I checked in with her often. It’s what she needed.” He frowned as his brother gripped the front of his shirt, dragging him down to eye level. “I would never hurt her. You know that. And you can’t tell me that you haven’t done worse before.”
Consternation pinched Dean’s brow. His fist tightened, further crinkling Sam’s shirt before he let go with a grunt. “I wasn’t myself back then.” Taking shallow breaths, he wiped his hands on his pants. When you stepped into his space, wrapping your arm around his torso, he looked away.
“I asked him to.”
But the look he shot at you solidified his disbelief.
You reached up to cup his cheek. He placed his hand over yours, still unable to meet your eye as he glared at Sam. “Dean. I’m okay. The cuts will be gone before we reach Tortuga.”
Mentioning your destination drained all the anger out of his shoulders, replacing it with something else. You couldn’t read him fast enough. He blinked the second emotion away and rolled back his shoulders.
“Alright. Fine,” he glanced up at Sam. “I won’t keel-haul you. But you’re up in the Crow tonight.”
“Yes, Captain.”
When Dean walked back into the cabin later that night, you were already sitting on the edge of his cot. He swept you up into a deep kiss, holding you close enough to feel his heartbeat against your palm on his chest. Your vision was hazy before he let you break away for breath.
“Are,” you panted, “are you alright?”
He nodded.
You reached up to drag your thumb across his bottom lip. “Then what is it?”
Taking your hands in his, he pressed his lips to your forehead. He let them rest there for a second before kissing you lightly. “May I have a chance to show you how I think you should be treated?”
“Of course.”
“No.” He shook his head. Clearing his throat, he tried to collect his thoughts. “That is – I know I kind of pressed you into this… deal. You don’t have to say yes unless you really want me to-“
To silence his racing thoughts, you bobbed up onto your toes and quickly kissed him hard on the lips.
Dean was stunned. Only for a second. “Yeah, alright.” He curled his finger under the neckline of your chemise. “Can you take this off for me? You don’t have to make a show of it… it’ll just be in the way of what I have planned.”
You stepped to the side and began to work the fabric over your head. Meanwhile, Dean tugged on the platform under his mattress. The cavity opened, revealing more blankets and few articles of clothing. He winked at you. Reaching towards the corner, he pressed on something hidden in the darkness. A door sprang open in the space between his and Sam’s bed. The fabric of your chemise finally fell to the floor.
“You’re a man of many secrets, Captain.”
Dean grinned as he dragged out a chest. “Sometimes. Only when I feel I need to be.” He nodded at the bed and told you to lay down. With a key tied to a string around his neck, he opened the chest. The lamplight made the contents sparkle. You gasped to see the chest filled to the brim with loose jewels, coins from several nations, and jewelry fit for a queen. Dean dragged it closer to the bed. It wouldn’t take a genius to figure out what he had in mind. You eagerly laid back into the blankets, arching your chest up for his large, warm hands. He lightly tweaked your nipples, smiling as you sighed.
The first piece of finery he brought out was a small diamond. It glittered between his fingers. He traced it across your chest and between your breasts before guiding it down your stomach. It was slightly cold as he nestled it into your belly button. Your body shivered. He pressed his palm flat over your stomach.
“If this is going to work, I need you to do something for me.”
“Yes?”
“You won’t be able to move much. Otherwise all of this is going to go rolling around the floor. I don’t want to spend my alone time with you hunting down my fortune. Think you can lay still for me?”
You thought about what Dean could have planned past draping you in gold, silver and gems. If he placed his mouth on you… there wasn’t much you could promise. With a shrug, you crooned at him, “I’ll do my best. If you play fair.”
Dean grinned in his lopsided way. “No promises.”
The necklace he pulled out of the chest next was the largest and most elaborate you’d ever seen. The bands of gold were woven together over emeralds and pearls. He laid it across your chest, licking his lips as you gasped at the chill of the metal. It was heavy. And covered you shoulder to shoulder. If even half of the chest contents were like the necklace, you wouldn’t struggle to stay still as much as you would struggle to not be crushed.
Taking hold of your wrists, he guided them to lay on top of one another above your head. He took out a strand of pearls.
You brought your hands down to your chest. “Oh, no.”
“Oh, yes.”
“But… the rope could break. They’d go everywhere.”
“No, they won’t. Because you promised to hold still for me.”
The challenge he laid for you loomed over your mind. While a good string of pearls had knots between the orbs, with all the sea air it wouldn’t take much for the string to be degraded and to give way. He took your wrists again as you fully realized his intention. He knew you wouldn’t struggle. You wouldn’t make the string break. Because he was trusting you with something precious. He was trusting you with his treasure.
With the pearls around your wrists and high over your head, you had nothing left to prevent him from draping you with just about everything in the chest. Bracelets and bands of gold wrapped around your arms and ankles. He draped necklaces and more bracelets in line with your ribs. Just above your tummy, he took his time in laying a pattern of doubloons, chuckling as you breathed with the initial chill of the shadow-kept wealth against your flushed skin. He left your legs clear. Taking out a few more coins, he laid them over your breasts before placing the last two over your nipples.
Dean stepped back to appreciate the sight.
You held as still as you could. Each shuddered breath made the coins on your nipples tremble. And you were sure your shivering body made everything shimmer in the light.
But the pirate wasn’t looking at the gold or the jewels. He was looking at you. How your hands curled against the back wood, framed by the pearls. How your torso canted and arched under the weight of it all. He seemed most enraptured with how your lips parted around your careful breaths. His tongue darted out to lick his bottom lip. Then he caught you watching him as he looked over you.
“I wish you could see yourself right now.”
You glanced down, trying to visualize the artful way he draped the jewelry across your skin. Most of it was warmed by your skin by now. But he flipped the doubloons over your breasts to their opposite sides, arching your back with the renewed chill. A bracelet completely made up of rubies slid off your ribs. Dean didn’t replace it.
Instead, he brushed away the coins from your breasts. Leaning down, he mouthed at one and the other. Your nails clawed against the wood overhead. He grinned against your skin, hearing the scratching and knowing how much you wanted to touch him. His teeth nipped at your skin. And his lips wrapped around your nipples brought to peaks. Reaching down, he batted your thighs open where you had shivered them closed. His fingers dragged between your folds, collecting the slick they found there.
“I take it you like being my treasure chest.” He sucked his fingers into his mouth and hummed around the taste. “You like it a lot.”
You nodded.
“How are you doing? What does it feel like?”
The words you wanted to say took their time showing up on your tongue. Dean’s fingers between your thighs kept distracting you. “I feel… precious. I feel like yours.”
The captain’s eyes glowed as you said what his chest wanted to hear. “That’s… that’s good. Do you think you can handle more?” He fixed a few pieces of jewelry where your squirming had shifted them. He trailed his thumb along the top band of gold and gems on the heavy collar necklace. The ruby bracelet that had slipped off your body was laid back in place. “You’re doing so good for me, Sweetheart. Can you hold still for me?” His hand flattened and cupped under your breast just short of squeezing.
Whimpering, you nodded.
But he had one more piece of jewelry to add before he began. He pulled out a bracelet with charms made of coins. It jingled as he swung it between his fingers. After kissing its destination, he laid it across your forehead. With the coins and the thick links of gold, he could have placed a merchant’s weight on your forehead and achieved the same effect. With the bracelet in place, you wouldn’t be able to look anywhere but up at the ceiling. You wouldn’t be able to look down and watch him take you apart; you’d only be able to feel it. Dean chuckled as you whined in complaint.
He situated himself so he was comfortably eye level with the juncture of your thighs. At least he started off gently. You weren’t sure you’d have been able to stay in place if he’d dove into your sex. That being said, the curl of his finger was enough. He stroked and slowly dragged it in and out of your slick until you were dripping. To make you jolt, he reached further for the spot that made you gasp. He pushed at it, pressed his fingertip against it. You could hear his hips thrusting against the sheet as he imagined hitting that same spot with his cock.
Your first release washed over you like a breeze. Breathing with it, a bracelet or two slid off your stomach. They landed with soft plops onto the blankets.
He kept going.
Dean only paused for a moment to watch you fall apart. But the second he heard your breathing even out, he curled a second finger into your heat and used it to scissor you open. He flattened a hand over the doubloons on your tummy to hold you in place. “Easy.” But he didn’t stop. With two fingertips stroking your walls, your vision blurred. You tried to hold off. You wanted to feel the zing of soaring pleasure for as long as possible before you came, making him pause his ministrations. But Dean finally took a chance to lick up your slick. And you were gone.
Again he paused, grinning as more of your glittering regalia fell off onto the blankets. But the collar necklace was firmly in place. It shimmered as your chest heaved. And the coin bracelet on your forehead kept your face upwards, even as your eyes fluttered.
He waited until your eyes closed. Then he wrapped his arms around your thighs and flattened his tongue against your sex. You cried out, calling for him. Whether to stop or to speed up, you couldn’t decide. Not that you could have diverted him from his course. He lapped his tongue as deep as it could through your folds. The obscene slurping noises coming from between your legs were punctuated with his hums and groans of delight. You were his favorite meal. And, pinned in place as you were between his hoard and his strong grip on your thighs, there was no way for you to escape. Even if you’d wanted to. He sucked hard on your clit. Your vision danced with stars in the darkness behind your eyelids. Soon, your cries softened to whimpers and shuddered gasps. Dean lightly suckled on your slit, easing you down, but never fully stopping.
“Dean-“
“Yes, Sweetheart?”
“What… what about you?”
“Oh, I’m going to get mine. Gotta take care of you first.” He nosed a few coins off your tummy so he could kiss the flesh there. “You doin’ alright?”
“Mhmm.” Your eyes rolled as you tried to focus. “So good. Dean, please… need more. Need you.”
He smiled, resting his cheek on your inner thigh. “You sure? I could do this all night and never want for anything else.” Reaching up, he flicked his thumb over the diamond in your belly button. It gave him no small pleasure that the simple motion made your whole body quake. He did it again just to watch you squirm. “Don’t you like me using my tongue on you?”
Shivering with need, you nodded. “But… I need more. I want you to fill me.”
He pseudo-gasped. “You do?”
If you could have glared at him without losing your forehead decoration, you would have. “Captain, please! Don’t tease.”
He crawled up and over your body till he could run the tip of his nose across the tops of your cheeks. “Are you trying to give me orders on my own ship?”
“N- no”
“Hmm. Good.” Dean tilted his head to kiss under your jaw. He reached down and began to untie the front of his pants. “I’d hate to pack all of this away before I was finished with you.”
You bit your bottom lip. “What else did you have in mind?”
His answer was to reposition his hips between your legs. The sight of your healing cuts gave him pause. The scratches were barely visible anymore. But there was enough of a texture difference between your thighs and the rough remnants that Dean could feel it under his thumb print. He pressed harder, testing the wounds for any lingering effects. When you didn’t flinch, he shifted his touch to smoothing up and down your hips. He slid his cock gently through your slick. You gave him a tiny whine as the press of him reminded you how sensitive you were. As it was, you weren’t sure you’d be able to sit down tomorrow without feeling how open you were. How open he’d made you.
When he did begin to fill you, you gave up trying not to lose his fortune. Most of it fell away from your body after the first few thrusts. Dean’s head dropped forward as he fully sheathed inside you. Panting, his arms shook from holding himself up on either side of your ribs. Hazy, you risked tensing your walls. He groaned, his eyes rolling shut.
“So it’s gonna be like that?”
“Yeah,” you smirked, “it’s gonna be like that.”
Dean fought to catch his breath. Then he reached up and pulled the large necklace off your chest. It landed with a thump on the floor, but he didn’t seem to care as he rested his face in the valley of your breasts. His torso, hot and sweaty with need, pressed to yours. You still had the string of pearls capturing your wrists. It kept your hands together when you brought them behind Dean’s head. You did your best to scratch your nails into his hairline without putting too much strain on the string. Without much length for you to tug on, you added more pressure to digging your fingers through his hair. Dean groaned, angling his hips and thrusting harder.
You couldn’t take much more of this. Maybe if he hadn’t brought you to completion so many times before this. Maybe if he hadn’t made you feel like the most dazzling treasure in his possession. Maybe… then you could have held back. Instead, you screamed his name as you came again, your body going limp. You hung off his neck as Dean continued to thrust, chasing his own release. He tried to hold back. He tried to thrust softer so he wouldn’t hurt you in your sensitivity. But his desire was stronger. Each thrust made whimpers and whines fall from your lips until his kiss smothered them. As he finally came, he growled into your mouth. You shuddered as his cum filled you, warming you from the inside out.
He collapsed on top of you, pressing the metal and gems into your skin. His body heat was higher than the treasure, making it feel chilled between your bodies.
He kissed at the side of your neck. “How you doin’ there, Sweetheart?” His nose nuzzled behind your ear. When you couldn’t answer with more than a sigh and lazy nod, he smiled against your shoulder. “Good. As you should be.”
You laid together for a while longer. Dean’s cock twitched inside you as he caught sight of the coin bracelet still in place. He peppered your face with kisses as he finally removed it and freed your wrists from the pearls.
After a while, when you were at risk of drifting off to sleep, he finally began to put everything away. You kind of missed the weight of being smothering in such finery. He slid up behind you for one last rutting of his cock between your thighs. His hand slid across your hip towards your stomach.
“Leave it in, Dean. Just for a little longer.”
“I would, Sweetheart, but I’m afraid that if I take my eye off it, you’ll never let it go.” He nipped under your jaw before removing the gem from your belly button. As he put the chest away and closed its hiding spot, you rolled to one side to look out the back window.
You waited for him to join you in his bunk again, but you could feel his eyes on your back. “Dean?” You glanced over your shoulder at him kneeling on the floor, watching you. “What is it?”
“I’m really going to miss you.”
A lump swelled up in your throat. You turned back towards the window before he could see. “I’m going to miss you too.”
He gently entered the bunk, inching his body close to yours. “You don’t have to go, you know. I know you’ve got that commission… but you don’t have to use it.”
“Yes, I do.” Your voice stammered as his knuckles stoked up and down your spine. “Where else is a woman like me supposed to go?”
Dean’s voice came out soft. And a little bit hurt. “You wouldn’t have to go anywhere.”
You bit on your thumb knuckle. It helped you fight back the tears that threatened to ruin your so-far wonderful evening. “We both know I can’t do that. Your crew has been very sweet to me. But I can’t impose on their hospitality for too much longer. I know you and Sam have been attacking fewer ships with me on board. I appreciate that. But I can’t ask them to sacrifice their… livelihood. And you and Sam can’t give up your portions forever.”
“Sure we could. You just saw my fortune. Just one case of it. Sam’s got just as much.”
“Please, Dean.” You blinked rapidly against the pained determination in his voice. “I- can’t. I have to offboard in Tortuga. I… I can’t be a pirate with you two. I can’t take- I can’t handle the cannons and the gunpowder and the…”
Dean shushed you. He wrapped his arm around your waist and pulled you close. “It’s okay. I know. You- you don’t have to. It’s not a life everyone can choose.” His hot breath panted against the back of your neck. “You wouldn’t to stay out to sea with us. We could set you up a house anywhere. You wouldn’t have to put up with anybody else besides the two of us.”
It was a concept. You could be a kept woman. Then again, why did it feel like the Winchesters would set you up in some quiet coastal fishing town so they’d have you all to themselves? Something about the promise of Tortuga… it wasn’t just the Ambrosia that you were looking forward to. It was being planted in the center of the bustle of the world. People and pirates and soldiers all coming and going with news from around the world. You wanted to live, not in the center of action and danger, but in the center of civilization where everyone would talk about it. A house away from it all didn’t sound as wonderful, even if it was secure. “But I would be trapped in that house. At the Ambrosia, I’ll be paid. Handsomely. After I make enough, I could leave whenever I wanted.”
Dean trailed his fingers up and down the curves of your body. “We could pay you an allowance. Enough to upkeep the house and enough for you to store up savings. You could leave whenever,” he cleared his throat to cover up how his voice cracked, “whenever you wanted to.”
“And what if something happened to you two on the seas?”
His fingers stopped their trailing.
“How would I ever find out what happened to you?”
Dean pressed his lips to the back of your shoulder. The lump in your throat swelled when he didn’t have an answer.
That was your true fear: not the missing out on the world and its wild ways. But never knowing if sending the Winchesters out to sea would be the last time you saw them. Would Dean’s friend Castiel sail up, his hat in his hand as he knocked on your door? Or would you find out when the money stopped coming in for the house and the bill collectors came? True, you could find out the same way at the Ambrosia. And the thought chilled you.
If Dean could follow your silent worries, he didn’t comment on them. Instead, he promised to deliver you to your commission as discussed. He joked that the pirates and merchant ships around Cuba would have to watch their wakes and the horizon for the Gazelle. But he and Sam would keep close. And they would ask again in six months.
The tears flowed freely down your cheeks. Dean tugged on your shoulder until you could lay on your back.
“I may be damaged goods by then.” You leaned into the hand he used to brush away your tears. “Who knows how many men I’ll have serviced by the time you drop by. It’s not like now… where the only men who’ve really had me have been the two of you.” You caught his hand against your cheek. “You and Sam won’t… won’t think that I’m-“
“We will want you and desire you just as much then as we do on the daily now. We could never think less of you for doing what you have to, what you want to, in order to survive.” His green eyes shown with the question he could never ask out loud.
Did you resent him and his brother for pillaging their way across the Caribbean?
Your thumb stroked over his cheek. “And I could never think less of you or Sam for choosing the life you live. I’m just sorry we can’t survive this world in the same places all the time.”
That bright green was lost to you for a second as his eyes closed. He turned his head so he could kiss your palm. “Thank you. I’m… I’m glad you understand this side of us. And I’m, ah,” he cleared his throat. He took in how your vision kept unfocusing and how your body kept sinking further into his bunk. “Rest up. I’ve worn you out. Or, at least,” he bobbed his head, “I like to think I have.”
You arched with a sigh. “Yes. I have been thoroughly fucked out. Sore in all the right places.” You hummed. “And I’ll be waiting for you and Sam when you two get back.” You both knew you weren’t only talking about the next several hours.
Dean took his time to kiss your forehead. His lips lingered as if he was memorizing the way your skin felt under his touch. Then he was gone. You laid alone with your thoughts for a long time, just watching the sea roll by.
***
Part 10: Farewell (Finale)
Masterlist
No Cum November 2023
#nautical november 2024#pirate au#captain!dean winchester#reader insert#dean winchester x reader#dean winchester smut#spn smut#winchester x reader#winchester smut
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I’m a simple pal. you give me a character who loves their siblings fiercely and unconditionally and I will IMMEDIATELY stan them until my dying breath
#about me#asl brothers#whitebeard pirates#yagami siblings#takaishida brothers#yunmeng siblings#wen siblings#nie brothers#obey me! lucifer#winchesters#morty smith#leonard snart#love#📌#from the drafts
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Okay but does Kate bushes song hounds of love feel like such a wincest song?? Another thing as well is that sam was 100% a kate bush fan as teen like I can just imagine him daydreaming about dean whilst listening to her music on a shitty cd player that barley works
#wincest#supernatural#sam winchester#also I’m imagining that dean bought him the cd player#and the cds!#post inspired by my extremely bit crunched pirated Kate bush cd
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