#captain!Dean winchester

[deepdisireslonging]

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 

Don't be a stranger! Feel free to comment, reblog, send me keyboard smashes about this work or anything I've written. Only please don't feed this into AI. I worked really hard on it and I don't want to feed the robots or the money grabbing ghost faces who operate them.

My commissions are open too! Read my Guidelines and let me know if I can write something for you.

[ant0niepax]

Honestly I love how I upgraded from Wattpad to tumblr, less cringe but still cringe to keep it entering

[raevenswritingdesk]

And wait what’s this hERE COMES JACKLES WITH A STEEL CHAIR

[faramirsonofgondor]

Sometimes babygirl is a severely repressed man with big cow eyes that get so shiny, a found family, and way too much trauma.

[blckbrrybasket]

can you do odd!reader responding to her partner w/ a breeding kink?

absolutely! im so so sorry for taking the longest amount of time to respond to this anon </3

odd!reader not picking up stuff is so real to me

Fem, Masc, and Gn reader featured

[fem/afab]

God you were so pretty, was all he could think. Even from the back you were utterly beautiful. His cock continued thrusting into your slick walls. He’d slide his dick out till it was just his tip notched inside your entrance before pounding back in. It was a hypnotizing rhythm that had you drooling into the pillow beneath you.

The other pillow held your hips up, keeping you presented nicely for him. His hand crept around your hip to draw shapes on your clit. Seeing the way your folds stretched around him made his dick twitch inside your cunt. “Fuuuck. Gonna fill you with up yeah? Have you carry my babies? D’be such a good mom.” He choked out without a second thought.

He, of course, was the only one not giving it a second thought. You always gave it a second thought though. Craning your neck, you shot an almost worried look over your shoulder. “I’m on birth control…and we’re not ready to be parents.”

If he hadn’t been balls deep in you he might have laughed. His hips snapped before slowing down in shock. “No it’s- it’s just dirty talk, babe. A saying?” You blinked as the cogs in your brain turned, a smile brightening your features once you realized. “Oh! Okay.”

Seeing you move on so swiftly had him shaking his head and beginning to thrust into you again. His teeth sunk into his lower lip as he focused on how you clenched around his dick, fucking through his confusion. It wouldn’t be the first nor last time it happened.

[masc/amab]

God you were so handsome, was all he could think. Even from the back you truly were attractive. His cock continued thrusting into your walls. He’d slide his dick out till it was just his tip notched inside your entrance before pounding back in. It was a hypnotizing rhythm that had you drooling into the pillow beneath you.

The other pillow held your hips up, keeping you presented nicely for him. His hand thumb rested at the top of your ass, watching the lube drooling out over his cock. Seeing the way you stretched around him made his dick twitch inside your ass. “Fuuuck. Gonna fill you with up yeah? Have you carry my babies? D’be such a good dad.” He choked out without a second thought.

He, of course, was the only one not giving it a second thought. You always gave it a second thought though. Craning your neck, you shot an almost worried look over your shoulder. “That’s not possible….and we’re not ready to be parents.”

If he hadn’t been balls deep in you he might have laughed. His hips snapped before slowing down in shock. “No it’s- it’s just dirty talk, babe. A saying?” You blinked as the cogs in your brain turned, a smile brightening your features once you realized. “Oh! Okay.”

Seeing you move on so swiftly had him shaking his head and beginning to thrust into you again. His teeth sunk into his lower lip as he focused on how you clenched around his dick, fucking through his confusion. It wouldn’t be the first nor last time it happened.

[gender neutral]

God you were so hot, was all he could think. Even from the back you were captivating. His cock continued thrusting into your slick walls. He’d slide his dick out till it was just his tip notched inside your entrance before pounding back in. It was a hypnotizing rhythm that had you drooling into the pillow beneath you.

The other pillow held your hips up, keeping you presented nicely for him. Seeing the way you stretched around him made his dick twitch inside you. “Fuuuck. Gonna fill you with up yeah? Have you carry my babies? D’be such a good parent.” He choked out without a second thought.

He, of course, was the only one not giving it a second thought. You always gave it a second thought though. Craning your neck, you shot an almost worried look over your shoulder. “We’re not ready to be parents.”

If he hadn’t been balls deep in you he might have laughed. His hips snapped before slowing down in shock. “No it’s- it’s just dirty talk, babe. A saying?” You blinked as the cogs in your brain turned, a smile brightening your features once you realized. “Oh! Okay.”

Seeing you move on so swiftly had him shaking his head and beginning to thrust into you again. His teeth sunk into his lower lip as he focused on how you clenched around his dick, fucking through his confusion. It wouldn’t be the first nor last time it happened.

[manpaindyke]

"yeah i have a girlfriend... she goes to st. michael's so you wouldn't know her."

new lesbian high school destiel au just dropped

[thelineofisstillhere]

I love how RTD suggested that those upset by how Janto ended should ‘content themselves watching shows such as Supernatural’

As if that had a positive gay relationship they could console themselves with????

WHAT DO YOU MEAN?! THE MOMENT WE GOT A CONFESSION OF LOVE CAS DIED AND NEVER CAME BACK?!

[hxad-ovxr-hxart]

HEY GUYS WHERES MY SASSY BRUNETTE/BLONDE WITH PARENTAL ISSUES, A PAST, AND A CUTE SMIRK?!?! THERE IS NO ONE UNDER THE TREE. IM WAITING

[imyourbratzdoll]

𝐀 𝐖𝐡𝐨𝐫𝐞'𝐬 𝐅𝐚𝐢𝐫𝐲𝐭𝐚𝐥𝐞

welcome to the land of fairytales, where desires you never knew you had will come true. thank you @georgiapeach30513 & @royalsweetteaa for helping me with this.

18+ only please, do not copy, repost or translate my work. You are responsible for your own media consumption.

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𝐦𝐚𝐢𝐧 𝐦𝐚𝐬𝐭𝐞𝐫𝐥𝐢𝐬𝐭

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!warning! these fics will include inter-species relations, size differences, innocent kink, age gaps and dark content.

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𝐅𝐢𝐜𝐬:

𝒊𝒕'𝒔 𝒂 𝒃𝒂𝒅 𝒕𝒊𝒎𝒆 𝒕𝒐 𝒃𝒆 𝒔𝒍𝒆𝒆𝒑𝒊𝒏𝒈 𝒃𝒆𝒂𝒖𝒕𝒚 - pairing: prince ransom drysdale x princess reader

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𝒎𝒂𝒚𝒃𝒆 𝒕𝒉𝒆 𝒍𝒊𝒕𝒕𝒍𝒆 𝒎𝒆𝒓𝒎𝒂𝒊𝒅 𝒘𝒂𝒔𝒏'𝒕 𝒂𝒔 𝒔𝒘𝒆𝒆𝒕 - pairing: prince frank adler x mermaid reader

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𝒐𝒑𝒆𝒏 𝒚𝒐𝒖𝒓 𝒍𝒆𝒈𝒔 𝒂𝒏𝒅 𝒉𝒆'𝒍𝒍 𝒔𝒉𝒐𝒘 𝒚𝒐𝒖 𝒕𝒉𝒆 𝒘𝒐𝒓𝒍𝒅 - pairing: street rat lloyd hansen x princess reader

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𝒔𝒉𝒆 𝒍𝒐𝒔𝒕 𝒎𝒐𝒓𝒆 𝒕𝒉𝒂𝒏 𝒉𝒆𝒓 𝒈𝒍𝒂𝒔𝒔 𝒔𝒍𝒊𝒑𝒑𝒆𝒓 - pairing: prince lance tucker x maid reader

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𝒕𝒉𝒆𝒓𝒆 𝒘𝒂𝒔 𝒂 𝒃𝒆𝒂𝒖𝒕𝒚 𝒘𝒉𝒐 𝒘𝒂𝒔 𝒊𝒏𝒕𝒐 𝒕𝒉𝒓𝒆𝒆 𝒃𝒆𝒂𝒔𝒕𝒔 - pairing: beast ari levinson, beast logan howlett, beast geralt of rivia x princess reader

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𝒘𝒉𝒂𝒕 𝒘𝒂𝒔 𝒘𝒓𝒐𝒏𝒈 𝒘𝒊𝒕𝒉 𝒑𝒐𝒊𝒔𝒐𝒏𝒊𝒏𝒈 𝒉𝒆𝒓 𝒔𝒆𝒗𝒆𝒏 𝒎𝒆𝒏 - pairing: bossy clark kent, sleazy johnny storm, dirty curtis everett, brawny steve rogers, cranky bucky barnes, tipsy dean winchester, horny sam wilson x witch/princess reader

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𝒃𝒂𝒎𝒃𝒊 𝒘𝒂𝒔 𝒋𝒖𝒔𝒕 𝒂 𝒔𝒕𝒖𝒑𝒊𝒅 𝒅𝒐𝒆 - pairing: hunter lee bodecker x shifter reader

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𝒘𝒉𝒐 𝒌𝒏𝒆𝒘 𝒂𝒍𝒊𝒄𝒆 𝒘𝒂𝒔 𝒂 𝒘𝒉𝒐𝒓𝒆 𝒊𝒏 𝒘𝒐𝒏𝒅𝒆𝒓𝒍𝒂𝒏𝒅 - pairing: mad hatter jefferson x dreamer reader 

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𝒔𝒉𝒆 𝒇𝒐𝒍𝒍𝒐𝒘𝒆𝒅 𝒕𝒉𝒆 𝒚𝒆𝒍𝒍𝒐𝒘 𝒃𝒓𝒊𝒄𝒌 𝒓𝒐𝒂𝒅 𝒐𝒏𝒍𝒚 𝒕𝒐 𝒇𝒊𝒏𝒅 𝒐𝒖𝒕 𝒔𝒉𝒆 𝒘𝒂𝒔 𝒂 𝒉𝒐𝒆 - pairing: scarecrow jake wyler, tin-man rick grimes, cowardly lion jake jensen, oz andy barber x lost reader

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𝒕𝒉𝒆𝒚 𝒘𝒆𝒓𝒆𝒏’𝒕 𝒂𝒔 𝒔𝒕𝒖𝒑𝒊𝒅 𝒂𝒔 𝒔𝒉𝒆 𝒕𝒉𝒐𝒖𝒈𝒉𝒕 - pairing: hansel steve kemp, male gretel nick fowler x witch reader

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𝒏𝒐𝒕𝒉𝒊𝒏𝒈 𝒄𝒐𝒖𝒍𝒅 𝒑𝒓𝒐𝒕𝒆𝒄𝒕 𝒉𝒆𝒓, 𝒏𝒐𝒕 𝒆𝒗𝒆𝒏 𝒉𝒆𝒓 𝒍𝒊𝒕𝒕𝒍𝒆 𝒓𝒆𝒅 𝒉𝒐𝒐𝒅 - pairing: big bad wolf luke danes x little red riding hood reader

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𝒔𝒉𝒆 𝒘𝒂𝒔 𝒂𝒘𝒂𝒓𝒆 𝒐𝒇 𝒕𝒉𝒆 𝒇𝒆𝒓𝒂𝒍 𝒎𝒂𝒏 𝒕𝒉𝒂𝒕 𝒍𝒖𝒓𝒌𝒔 𝒊𝒏 𝒕𝒉𝒆 𝒔𝒉𝒂𝒅𝒐𝒘𝒔 - pairing: tarzan tangerine x jane reader

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𝒔𝒉𝒆 𝒘𝒂𝒔 𝒂𝒃𝒐𝒖𝒕 𝒕𝒐 𝒃𝒆 𝒌𝒏𝒐𝒘𝒏 𝒂𝒔 𝒕𝒉𝒆 𝒈𝒊𝒂𝒏𝒕𝒔 𝒘𝒉𝒐𝒓𝒆 - pairing: giant august walker x female jack reader

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𝒕𝒊𝒏𝒌𝒆𝒓𝒃𝒆𝒍𝒍 𝒘𝒂𝒔𝒏’𝒕 𝒑𝒓𝒆𝒑𝒂𝒓𝒆𝒅 𝒇𝒐𝒓 𝒕𝒉𝒆 𝒏𝒊𝒈𝒉𝒕𝒎𝒂𝒓𝒆 𝒂𝒉𝒆𝒂𝒅 - pairing: captain hook negan, captain hook jack sparrow x tinkerbell reader

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𝒕𝒐𝒐 𝒉𝒐𝒕, 𝒕𝒐𝒐 𝒄𝒐𝒍𝒅, 𝒋𝒖𝒔𝒕 𝒓𝒊𝒈𝒉𝒕 - pairing: alpha bear ari levinson, alpha bear henry cavill, alpha bear lee bodecker x goldilocks reader

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𝒔𝒉𝒆 𝒘𝒂𝒔 𝒉𝒊𝒔 𝒑𝒓𝒆𝒄𝒊𝒐𝒖𝒔 𝒍𝒊𝒕𝒕𝒍𝒆 𝒔𝒘𝒂𝒏 - pairing: prince steve rogers x princess/swan hybrid reader

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𝒐𝒉, 𝒉𝒐𝒘 𝒅𝒖𝒎𝒃 𝒔𝒉𝒆 𝒘𝒂𝒔… 𝒅𝒐𝒏’𝒕 𝒚𝒐𝒖 𝒌𝒏𝒐𝒘, 𝒏𝒆𝒗𝒆𝒓 𝒕𝒓𝒖𝒔𝒕 𝒕𝒉𝒆 𝒕𝒉𝒓𝒆𝒆 𝒎𝒆𝒓𝒎𝒂𝒊𝒅𝒔 - pairing: mermaid jennifer check, mermaid rosalie hale, mermaid jane smith x clueless reader

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𝒋𝒆𝒂𝒍𝒐𝒖𝒔𝒚 𝒘𝒂𝒔𝒏’𝒕 𝒂𝒏 𝒆𝒎𝒐𝒕𝒊𝒐𝒏 𝒕𝒉𝒆 𝒍𝒊𝒐𝒏 𝒌𝒊𝒏𝒈 𝒌𝒏𝒆𝒘 - pairing: mufasa ari levinson x scar sergei kravinoff (kraven the hunter) x lioness reader

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[phantomstatistician]

Sample Size: 77,180 stories

Source: AO3

[deepdisireslonging]

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

[thestarsmakemedream-art]

SUPTOBER - DAY 31 - HALLOWEEN / COSTUMES So the thing is that I had this idea for last year's suptober prompt "Trick or Treat" already. Time and work was not nice with me that October, so the little Star Trek fans (I imagine Cas as Bones aka Dr McCoy) and baby Jason (don't worry he only has a butter knife) had to wait this year to go trick or treating. Anyway, this is a wrap, once in my life I finished a whole month with drawings for each day. WOOHOO! Tomorrow I will make a masterpost about everything. Last but not least I want to thank @wigglebox , because without her this year we wouldn't even had Suptober. Without a question the true hero of this community.

[thekingofspin]

after reading these I think i can finally label what my type is

[batbitten86]

fuck questions like “what you favorite color?” tell me what fictional character you’re so obsessed with you can’t even think or hear about them 

[blckbrrybasket]

RAHHH i loved the odd!reader piece you posted!! i would love to see more, only if you want to write more, no pressure!! <33

ahh im so happy that you like it!! i love odd!reader so much <3 so so sorry this took a bit to come out

if you or anybody has any ideas for odd!reader plssss send them my way i would love to write more for them!!

have some headcanons and a lil something 💫

- When in public there are times where they’ll never touch their boyfriend or stand so close next to him that their face is in his side.

- It’s become a bit of a one-sided competition for their boyfriend to try and fuck them dumb (quickly mentioned in the blurb but he does take it as a challenge)

- They’re very clumsy. It’s not very noticeable to them anymore. Elbows knocked on door frames, tripping, miscalculating how far away something is, is all common to them.

- Surprisingly not queasy to most things, sees it as a part of life.

- That being said, the most horrendous thing could happen to them and they’d shrug like “:/ what can you do?” While their boyfriend is staring at them in horror.

- Knows way too many random facts. Makes it interesting to watch shows or movies when they randomly drop facts about the filming process or the lore.

- Bounces their leg like nobody’s business. Has spilled things by hitting their knee on the table.

- Egregious sleeper. Why can they fall asleep to the sound of gunshots outside, but if something interrupts their rain sounds they can’t sleep.

- Knows whats best but doesn’t know how to express it so they’ll just say “yes” or “no” and expect everyone to understand why.

The girl on screen pressed herself against the side of the house, panting as she tried to find a good moment to run. You and your boyfriend were watching a horror movie as you squirmed in your seat. Your legs were laid out over his lap, draping over the armrest of the couch.

“She actually called 911.” You muttered, popping a piece of popcorn into your mouth. “Well yeah-“ He started. “No like the phone was still connected. When filming she accidentally called 911 multiple times.” You finished the thought.

He raised his eyebrows at you, not questioning, only turning his head back to the screen when a blood curdling screen was ripped from the actor. “Yeah?” You smiled contently. “Mhm!” A few moments passed by quietly, aside from the gore on the TV.

Your eyes trained on the screen as the girl ran around the house only to be met with the slasher. The knife stabbed into her, a small grimace finding itself onto his face at the forced angle of the cut. “Do you think it would be cool if the cloak was white instead of black?” The question pulled him out of watching the movie and he glanced at you. “Huh?”

“Well originally the cloak was going to be white and if it stayed that way it would be covered in all the blood stains. It’d look cool.” He slowly nodded, “But the black looks cooler in the night.” You paused before a smile spread across your lips. “Yeah. You’re right.” His hand wrapped around your ankle and his thumb slid back and forth over your skin, both of your attentions falling back to the film.