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talesmaniac89 · 2 years ago

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Charity Heist 12 - aka. All Chained Up With Nowhere to Go

A Supernatural Heist AU - Masterlist

Pairing: Hitter!Dean x Thief!Reader

Summary: The Singer & Winchester Retrieval Agency is the best group of con artists in the world. But even though Y/N can crack safes, scale buildings and infiltrate even the most secure locations, she still can't find a way to deal with her all consuming feelings for the group's greek god of a hitter; Dean Winchester. How will she handle their next big heist, when she's forced to get up close and personal with the man of her dreams?

Warnings: Idiots in love, smutty thoughts, a lot of swearing and a ton of bad jokes.

Watch the trailer here

A/N: This story is 50% jokes and 50% dirty thoughts. No deep angst, just fun and action! Inspired by the series Leverage.

Y/N = Your Name | Y/E/C = Your Eye Colour

Start Here - Last - Next (Coming soon)

Making your way to the back of the night club, you looked at your watch and held your breath for a second as you listened out for trouble. Sam would have made it to the guards stationed out front by now, but you didn’t hear any signs of fighting. Which should mean you were good to go.

So, with one last glance towards Dean, who was setting up close enough to react if you called for help through the comms, but not close enough to be spotted, you slipped around the corner and rolled your shoulders as you faced the wall.

Surveying your surroundings you smirked at how goddamn easy they’d made it for you. The building was from the 1950s or 60s, by your estimation. God how you loved architects from the ‘golden era’.

Their hard-on for the Brutalist style of architecture meant you were left with plenty of sharp angles and ledges to use when scaling the wall. And this building was no different. All blocky and filled with unnecessary little ledges and windows that were nearly too close to each other, all the way up. Like your own little stairway to heaven.

If heaven was the roof of an abandoned nightclub that was…

Shouldering your bag of tools, you slipped on your gloves instead. Choosing to free solo the climb. Sure, you did have climbing gear in the bag for scaling walls. But using any of them on that wall would be an affront to Charlie’s genius.

So, instead you easily scaled the simple structure in a few short minutes without getting any tools out of your Mary Poppins bag of thievery. Not even slightly winded from the easy climb as you hoisted yourself up on the ledge and looked down over it with a smirk.

Suck it Catwoman.

With no time to waste you quickly, and quietly, made your way across the roof, looking for the skylight featured in Charlie’s blueprints. Keeping low so as to not be seen by anyone passing by, as the completely flat roof left little in the form of blind spots if someone were to look up at the wrong moment from across the street.

Luckily, the skylight itself was easy enough to spot. Even though it was covered in a grimy layer of dust and dirt from years of being left unattended, some parts of it still caught the bright sunlight and reflected it back at you. And, like the sneaky little thief you were, you could spot anything even remotely shiny from miles away.

Skylights, apparently, included.

Slowing your pace, you dropped down along the edge of the glass and squinted through the layer of dirt, looking for… Well, more dirt. Just this time in the shape of the mobster who was stupid enough to get himself caught. Your earlier high from scaling the building faded at the thought of having to rescue the master of sass himself as you frowned at the dirty glass, looking for a spot that was clean enough to look through.

Once you finally found a dime sized spot, however, your smile returned. Twisting into a smirk as you looked down at Crowley in the middle of the room. It warmed your little thieving heart to see the smug bastard chained to a chair with, from what you could tell, some kind of cloth shoved into his mouth to gag him.

Apparently you weren’t the only one who didn’t appreciate the mobster’s style of ‘communication’.

Better yet, they clearly didn’t see Crowley as the big bad he made himself out to be. Either that or Sam was really wowing the crowds out in the front of the nightclub… Since the room was free of guards. Leaving your little damsel all on his lonesome.

Which made your job a hell of a lot easier. Since it meant you wouldn’t have to silently knock them out one by one before rescuing the chained up princess.

Sitting down cross-legged on the roof next to what looked like one of the easiest glass panels to remove, you pulled your bag of tricks off your back.

Though you didn’t mind just watching Crowley’s misery through the dirty skylight, time was of the essence. If not for the mobster, then for your friends on the ground. Which meant you needed to work fast, instead of making Crowley suffer some more. Which would have been fun. Especially since you’d have front row seats to the show. But alas, duty called, and you’d long since lost ghosting privileges against that cruel bitch, so you had to answer.

With one last smirk down at the chained up mobster, you quickly pulled out your pre-calculated lengths of rope and additional harness hooks. Expertly putting on your full rappelling gear and triple checking your knots as you mentally did the math, trying to calculate how high up you were.

Charlie’s blueprints had included an approximation of the height from the ceiling to floor, so you should have just enough rope to make a safe and soft landing. But sometimes those blueprints were rounded down. Which could leave you a few inches short. So you still eyed the floor warily, before deciding that… Fuck it, it was a close enough match to your pre-determined rope length. Letting you shave a few minutes off of your prep.

Pulling on your harnesses, you triple checked that everything was in working order with a few sharp tugs. Allowing yourself a pleased hum when everything stayed unmoving and taut under your expertly trained fingers.

Fuck 50 shades… Christian Grey had nothing on your rope work.

Next up in your backpack of wonders, you pulled out the throwing knives Charlie had designed for you. Using one to loosen the panels you’d be rappelling down through before tucking the other blades away safely inside your sleeve. Just in case you had to face off with a goon while rescuing the damned Scotsman.

The silicone holding everything in place was old. And so, you could luckily make quick work of it the old school way, without involving other gadgets to soften the bindings or cut through the glass. Soon enough you held the first glass panel gently between two gloved hands. Grinning victoriously at the pane before just as gently placing it on the roof beside you and working on the next one.

The last thing you needed was glass dropping down onto the concrete floor below and alerting the guards. Even if it would have been funny to see Crowley’s reaction. Or even better yet, having the panel knock the mobster out completely. At least then you wouldn’t have to actually listen to him as you saved his ass.

Luckily they were big enough, so after removing just four of the sturdy glass panels, you had just enough space to safely let yourself rappel down through the skylight.

“All set, got eyes on our damsel. I’m moving in now,” You whispered out into the empty space around you. Knowing your earpiece would catch your words and transfer them right into the ears of both Sam and Dean.

Giving it a beat, you waited for Dean’s confirmation and held your breath hoping you wouldn’t hear from Sam. Afterall, the youngest Winchester had his piece muted unless necessary so that his own grifting wouldn’t interfere with your infiltration as he talked circles around the guards out front. If he answered you, it would mean quietly and carefully was out the window and Dean would have to go in guns blazing.

“Coast is still clear, Sam’s keeping them busy…” Dean’s voice ended on a hesitant note that had your body tense as you waited, holding your breath in case your hitter had been spotted talking to himself by an eagle-eyed guard. Yet, as he continued speaking, you let your body relax with a soft smile.

“Stay safe (Y/N)...”

“Always Dean, you know me. Risk-averse as fuck,” You shot back with a small grin, knowing your words would have the mercenary rolling his eyes and Sam doing his utmost to not do the same. After all, considering part of your job description was rappelling down buildings, crawling through claustrophobic ventilation systems and dodging lasers, you were the furthest thing from ‘risk-averse’.

Crouching by the side of the now open section of the sky light, you took a breath to steady yourself without waiting for any response from either of your ground based backup. Knowing neither would want to reward your absolute comedic genius with an answer anyway.

Instead, you refocused on your task at hand; hooking your harness lines up to the sturdiest pipes and concrete outcroppings you could see.

This was it. The best part of the job.

Looking down at the ground three full floors below from the theater styled open concept of the nightclub, you smirked at Crowley’s bound form. Still completely unaware that you were about to drop down and rescue his ass. Luckily the skylight was focused directly on the middle of the dance floor. Saving you time as you wouldn’t have to slow your descent to deal with the two levels of balconies and seating areas surrounding the dancefloor where Crowley was chained to his chair.

A straight forward leap of faith would do just fine.

And they were just so much more fun than stupid slow and steady descents.

The seconds before a jump always made you feel like you were in one of those action movies Dean loved making you watch in your downtime. Even though he spent every second criticizing every single action hero for their shoddy gun work. Not that you were any better. Any break-in scene was always heavily peppered with your own expert opinions.

Taking one last breath you stood up and rolled your shoulders before turning until your back was facing the open section of the skylight. And, with no hesitation, you stepped back. Letting yourself freefall down into the building.

You were Tom Cruise in Mission Impossible. Just hotter, not out of your mind, and with actual skills. You were James Fucking Bond, and for once not a damn Bond girl. You were grace personified. You were…

Fuck.

The harness snapped taught just a few inches off the floor, cutting off your internal monologue as effectively as it cut off your oxygen.

You were winded.

---

Luckily, the slightly botched landing was done behind Crowley. And even when winded, you were a professional, which meant he wouldn’t even know you were there until you wanted him to know. So the Scotsman didn’t get to gloat at your less than graceful entrance.

Unhooking your tether, since you knew you couldn’t carry the fully grown man back up, you took a second to poke gently at your slightly sore torso with a grimace before you cleared your throat to alert Crowley to your presence. Taking a bit of pleasure in seeing the big bad tense up in fear until you strolled nonchalantly up from behind him, coming into view from behind his chair.

Yet, as soon as he saw it was you, and not the people who had given him all that fancy new silver jewelry that locked him to the chair, the mobster visibly relaxed in his seat. Leaning back with what you thought was a smirk through the oily cloth the bad guys had used to gag him as you scowled at the infuriating Scotsman.

Nodding his head, Crowley asked you, non-verbally, to remove the gag in his mouth as you just smirked down at him. For a second, you considered just leaving it there. But you knew it would only buy you a minute, at most, until you picked the locks on the cuffs and chains locking him to the chair anyway. And that minute of him staying gagged would probably just lead to more sass once he could remove the gag himself.

It just wasn’t worth it.

Sighing in defeat, you grimaced as you pinched the outside of the cloth with two gloved fingers. Not wanting to be anywhere near the mobster’s mouth as you gingerly removed the oily cloth that had clearly just been grabbed off of some of the debris lying around in a desperate attempt to shut the talkative Scotsman up.

As soon as the gag was out, however, you really wished you’d left it in. Or one better; decided to just knock the damn irritating man out so you could rescue him in peace.

“Here to help me darling?” Crowley sounded relaxed and confident as he spoke up without even as much as a thank you. Throwing you that trademark smirk as the chains clanked with a small wave of his fingers in your direction. Huffing you dropped to your knees and shrugged off your backpack again with a roll of your eyes. You wanted to be out of there fast. If nothing else, just to not have to be around the self-proclaimed king of the underground.

“Oh… Honey. You need a lot of help. But I can’t help you. Once we get out of here, go make a therapist rich somewhere. Preferably far away from me,” You snapped back as you pulled out your lock picking set. Sneering up at Crowley as he chuckled dryly at your comeback.

“Concerned for my well being are you? That’s sweet (Y/N). Once this job is done you should come work for me. Keep an eye on me from up close and… Personal,” Crowley’s words were peppered with enough innuendo to make you gag on it as you shuddered visibly at the idea of being anywhere near the mobster for an extended period of time.

Sure, you knew it was all just… Harmless, with Crowley. He wasn’t interested in you. He was only interested in your reactions. Because though you could put up a good front when you needed to, you could never hide your disgust whenever the mobster flirted with you.

Throwing him another sneer, you placed the extra picks between your teeth to keep from cursing the man out. As you glanced up at him before refocusing on the locks that needed picking, your features twisted into a small smirk as you noticed the bruises forming under his eyes for the first time.

At least they beat him.

Getting to work, you made easy work of the first chain shackling his feet to the ground. Not wanting his hands loose whilst you worked. Luckily the bad guys had made use of standard industrial padlocks to lock the chains around his feet. Even if they’d gone a little overboard by having four separate locks on the damned things.

Not that it mattered, you could have opened the laughably simple locks with nearly anything. While blind folded. Though, you didn’t let that on, as you pretended to focus on the locks. In some vain hope that the man in his damned tailored suit would shut up and let you work.

Though, you should have known better.

It was Crowley. If he stopped talking, it probably meant he was dead. Or worse… Scheming something.

“Don’t you feel sorry for me?” The mobster prodded, clearly having noticed your little pleased smirk at seeing him bruised and beaten. Which… Hell. Why would he even ask? Your smirk should have been answer enough. If Sam hadn’t profusely forbidden it, you would have already socked him one yourself, for putting your whole operation in jeopardy.

“I have no sympathy for criminals,” You spat back between clenched teeth to keep the spare lockpicks in place as you got to work on the next padlock, having already made short work of two of the four chaining his legs to the chair.

“You know, (Y/N), you’re technically a…” Crowley just drawled back, throwing the defense you’d offered up to Dean only hours earlier right back in your own dumb face, though he had no way of knowing. And, unfortunately, also bringing back memories of the explosive results to follow in the closed and private gun range. Which left you with little mental capacity to think of a good comeback as your fingers trembled around the lock picks before cutting off Crowley’s words with a growl.

“Shut. Up,” Spoken through gritted teeth, your words came out with a little less sass and a whole lot more anger, which thankfully, for once seemed to temporarily shut the mobster up. Even if it was because he was busy musing over what had made you so angry just so he could use it as ammunition against you in the future.

Taking a deep breath through your nose, you absentmindedly sucked on the two lockpicks you’d placed in your mouth. As if the taste of steel and the fresh dose of oxygen could push away any thoughts of Dean’s lips… Or his arms, or body or… Damn it. Even through the taste of steel on your tongue you could still taste that hint of spiced peppermint.

Forcing yourself to focus, you removed the two picks you’d been biting on from between your teeth and instead bit the inside of your cheek as you made quick work of lock number three and four, leaving Crowley’s feet free. Though his hands were still both handcuffed to the chair.

You were a goddamn professional.

You’d done well so far at keeping the memories of the gun range or closet from interfering with the job. Sure, things had been awkward in the truck, but you’d still done what High School Musical taught you and kept your goddamn head in the game.

There was no way in hell you’d let Crowley destroy your flow this close to the finish line.

“Take your time darling, I’ve got all the time in the world,” Crowley drawled. As if you weren’t already picking the locks in fucking record time. Though, for once, you were nearly grateful for his damned sass. Since it forced your thoughts back into the not-exactly-safety of the abandoned nightclub instead of the much more dangerous territory that was the bunker’s gun range.

“Do you enjoy it?” You just mused back as you moved up to the first pair of handcuffs chaining his left hand to the arm of the chair. Taking your damn time with positioning the lock so you could see the keyhole, just to piss the mobster off a little bit more.

You took your victories where you could find them, and Crowley had just served this one up on a silver platter. Though he put up a good front, you hadn’t missed the slight urgency to his lazy drawl. Nor the little nervous glance of his dark eyes towards what you guessed was the door behind you; keeping an eye out for any uninvited guests crashing the party.

Which, in fairness, you would have been too. If you didn’t trust Sam to have your back. Or at least warn you if he couldn’t stop the mobsters outside from coming to check on their hostage situation.

“Enjoy what pet?” Crowley seemed slightly amused as his eyes watched you expertly place your picks in the small lock on the side of his shiny new silver bracelet before rising to meet yours with that same cocky smirk back in place.

“Being an insufferable ass,” You snapped back just as the handcuff on his left wrist clicked open.

“Of course… Why do you think I do it all the time?” Crowley chuckled, following his words up with yet another example of his trademark insufferableness, as he got in your way by pulling his now free hand across his body to use his still tied up right hand to rub away the irritation left by the cuffs. Stopping you from continuing your lock picking as you rolled your eyes at the big baby.

“A hard childhood? Past trauma? Some Freudian level shit with your parents? Actually... I’ve met your mother. That does explain some shit. But still… Shush, I don’t want to know. Take it up with the therapist I told you to hire,” You shot back as you pushed his free left hand away to give you access to the last lock keeping him chained to the chair. Keeping up your rant until you heard the satisfying sound of the final lock clicking open to stop Crowley from shooting in with even more sass and delaying your work.

“Or you could come work…” Crowley started again as he gently massaged his now free right wrist, but before he could even get the words out, you held up a hand. Both in refusal, and because the voice you’d hoped you wouldn’t hear until you were safely out of range of the nightclub was coming through loud and clear in your ear; Sam.

“(Y/N), two of them are coming your way. Couldn’t stop ‘em. Dean…”

Zoning out whatever orders Sam had for your hitter, you quickly turned on your heel to face the door Crowley had been eyeing warily just moments earlier. If you’d been alone, you’d be able to evade them easily. But you weren’t, and you doubted Crowley could just poof out of the room while you ran for cover. No matter how much he dressed like a budget cruise ship magician.

Your only choice was the rear entrance.

Which was probably also the entrance Dean would be rushing in through to provide you backup based on the few words you caught between Sam and him. With any luck, you’d reach the door before the mobsters came to check up on Crowley. Or at the very least, you’d have Dean providing some cover fire for you while you got the hell out of dodge.

“Get moving Crowley, we’ll have company any minute now,” You hissed towards the mobster who quickly got to his feet and looked to you for direction. Looking wide eyed and lost as he stood frozen in place, eyes focused on the main door. Which had you once more rolling your eyes at the clueless Scotsman.

“The back door! What are you waiting for? A fucking invitation?” You stage whispered as you nodded towards the door at the other end of the dance floor behind Crowley’s chair.

Pushing him forward, you followed closely behind him across the open, empty concept of the former nightclub’s main floor. Fuck, you hoped the goons coming to check weren’t carrying guns. There was barely any cover to hide behind at all. Though, if it came down to it, you’d totally use Crowley as a meat shield. Because fuck that.

You weren’t getting shot just because that fucking idiot wanted to play Cinderella at the ball with a shiny new suit in the middle of a damn con.

“Where’s your backup?” Crowley’s question was staggered and broken between heavy breaths as he hurried towards the back entrance, at much too slow a speed for your liking.

“I’m not really the… Fighting type,“ He clarified when you chose to keep running instead of answering him. Urging him forward with a not so gentle push, you kept your ears peeled for the sound of the door behind you opening, or the booted stomps of some cartoonishly large goons chasing after you.

You just knew they’d be cartoonishly large. It was part of the damn ‘goon’ job description. You were nearly 99% sure the big bads of the world came together once a year to have goon casting calls. To find the biggest and baddest next generation of villainous himbos to do their bidding through some criminal parody of the X-Factor.

“Don’t worry, I have a few knives up my sleeve. You just keep running,” You huffed back as you eyed the rear entrance. You were nearly home free. Yet, just as soon as the thought struck you, you heard the unmistakable click of a door opening somewhere behind you. Followed closely by the surprised shout leaving the angry mobster as he spotted you across the dance floor.

“I think you mean cards,” Crowley shot back with just a hint of that same snark. Before the sight of the goons charging towards him, and by extension you, finally lit a fire under him making the mobster speed up. Sprinting towards the door at a speed that could have gotten you the hell out of dodge before the damned goons showed up. But of course he waited to become fucking Flash Gordon until the threat of more oily cloths being stuffed down his gullet became very real.

Fucking typical.

“Nope… I mean knives,” You spat between sharp breaths as you dug out one of the throwing knives you’d stashed in your sleeves while still up on the roof, spinning on your heel to get the biggest, baddest and maddest goon into view before throwing the small, lethally sharp knife at one of your two pursuers.

He was, of course, just as cartoonishly large as you’d suspected him to be. Which made him an easy target for your pretty much perfected marksmanship. Hitting him in the upper thigh, you grinned as the big guy stumbled over his own feet in shock. Clutching at his injury, he growled at you once, before his legs failed him and he crumbled to the floor with a muted scream.

With any luck, on his side, the deep cut to his femoral artery wouldn’t kill him. But he definitely wouldn’t be able to walk for the next few weeks.

Biting back the need to shout timber as the big lug fell, you dug out another knife and threw it at goon number two as you kept running backwards towards the door. Not taking as much time to line up your shot, since the second giant was quickly gaining on you. Your knife flew towards his knee, but after seeing his colleague crumble, the big guy was on the lookout for more of your little stabby projectiles, and just barely dodged it as he kept rushing towards you.

Fuck.

Just as you were about to take out another of your precious knives to waste on the damned slippery bastard rushing you, the room, and goon, in front of you was suddenly bathed in light. The sharp light blinded the goon for just long enough that you could turn to face the source of it. Sighing in relief you squinted towards the sudden brightness spilling into the slightly dim nightclub from the rear entrance.

The cavalry was here.

Leaving your knife in your sleeve, you shot Dean a grateful grin. Even though you couldn’t fully see him, just the outline of him; all bowlegs and muscle. In front of you, however, Crowley nearly came to a full stop as you crashed into him.

Seemingly not realizing that the only creature on God’s green earth with such a damned near perfect silhouette was Dean Winchester. But… Then again, Crowley was probably not constantly daydreaming about the Greek God of a mercenary like you were. Though you wouldn’t put it past him. You had seen him attempting to flirt his way into getting Dean to join his crew more than once.

“Idiot! That’s our backup!” You hissed at the mobster, pulling him forward by the arm. Before just as quickly forcing his head down with a rough hand as you watched Dean line up his shot from in front of you as the goon behind you started charging forward again. The gleam of the silencer nearly blinded you fully as you crouched low and kept running for safety. Reaching Dean just as the slight whistle of the silencer signaled that the bullet had left the barrel and buried itself in the shoulder of the mobster that was still standing.

Looking up at Dean from where you were crouched next to him, you raised an eyebrow. Dean was an excellent shot. But that one didn’t match his style. A shot to the shoulder wouldn’t take that giant of a man down fast enough for you to get away. Yet, before you could question your sharpshooter, you watched as the second goon came to a full stop. His feet unsteady under him as a hand went up to his shoulder; a look of anger, tainted by complete confusion on his big dumb face. Before he promptly, and not-so-gracefully, fell flat on that very same face.

“Tranquilizer pellets, Charlie and I’s latest invention. Forget knocking out an elephant, one of these bad boys pack enough punch to knock out the whole damn zoo,” Dean grinned in answer to your unspoken question. The smile made the seasoned mercenary look much younger, as green eyes shone with the joy of getting to play with one of his toys.

Though he might be a trained mercenary and one of the most dangerous men on the planet, at his core, he was still just a big kid. And the bigger the gun, the happier Dean Winchester was.

“Please don’t tell me Charlie thought those up to knock me out the next time I decide to just say fuck it and have 6 espresso shots in one coffee again?” You asked, ignoring Crowley’s protest as you nearly shouldered him out the door. Too focused on Dean’s carefree smile to even bother looking over at the damsel you’d just saved.

“Can’t tell you sweetheart. I’ve been sworn to secrecy,” Dean shot back with a laugh as he shut the rear entrance behind you and placed a warm hand at the small of your back, leading you forward as you tugged Crowley along by one of his stupid tailored suit sleeves.

“I knew it,” You huffed jokingly before letting your smile drop as you looked back towards the still thankfully shut rear entrance.

Time to get the hell out of dodge.

“Sam, the job’s done. Mind calling us an uber?” You called out into the headset, knowing the younger Winchester would have been listening in and was probably already on his way from your earlier comments to Dean.

“Already on my way, get back down the road, half a block away. I just saw the rest of them run into the nightclub, so hurry. They’ll start swarming soon,”

The sound of Sam’s truck door slamming shut acted as the full stop to his sentence as you started speeding up. As soon as Sam’s words reached you, Dean’s hand applied some pressure to the small of your back, rushing you forward as you both decided to ignore your much slower third wheel while hurrying away from the not-so-abandoned nightclub.

Crowley, however, seemed to have gotten the message as he quickly tried to fall back into step with you. Ignoring the hard look Dean sent him as he instead grinned at you between huffs of air.

“Going back to what I was saying before we were so… Rudely interrupted,” He said between breaths as he struggled to keep up with Dean’s much speedier steps where the hitter was nearly pushing you down the road. God, even when running he had to take the time to be obnoxious. Instead of saving his breath for, well, breathing. Which the normally desk bound mobster seemed to sorely need to focus on.

“No,” Your tone was flat and clipped as you cut him off again. Not wanting to hear more of his bullshit as you longed for the relative safety of Sam’s truck, and the far off future where you no longer had to listen to the king of sass.

“I’m just saying darling… You seemed so worried for my safety in there. Things like that… Move a man,” He continued, despite your quite clear rejection. Completely ignoring the burning looks Dean was sending him, though it was much harder for you to ignore, as Dean’s hand that had previously rested softly on your lower back snaked around your waist to pull you closer to his side and away from Crowley. Making it much harder for you to sprint forward and away from danger.

“You can take that job offer and shove it…” Before you could finish spelling out your creative new filing system idea to Crowley, you were interrupted by the squeal of tires as Sam’s big truck pulled up next to you.

“Get inside, now,”

The urgency in Sam’s tone was doubly underlined by the shouts coming from back at the nightclub, where the rest of the mobsters had seemingly found their knocked out buddies and were busy flooding out of the back entrance of the building.

Swallowing your words, you instead let your irritation fuel you as you wrenched open the door before, unceremoniously, shoving Crowley inside the backseat. Frowning as you realized you would have to sit next to him, you still slid out of Dean’s hold on you and into the backseat of the truck after the mobster.

However, as you reached for the door to wrench it back shut, Dean stopped you with a big hand holding the door open. His green eyes were still burning a hole in Crowley, who barely even seemed to notice him as he was busy trying to remember how to breathe. Before sending you a weary eyed look after shooting a final round of daggers at Crowley as he shut the car door and ran around to the passenger side.

---

As soon as Dean slid into his seat, Sam gunned it down the road. Not caring if the loud roar of the car engine caught the attention of the mobsters that had now flooded into the street half a block back.

You were home free.

Taking a deep breath, you leaned back in your seat, closing your eyes to take stock of your losses. You’d managed to grab your backpack. But the new ropes for your shiny new harness were lost. As were two of your favorite knives. Bastards. Maybe you could take it out of Crowley’s paycheck? It was his fault after all.

As you opened your eyes to suggest that the costs of the rescue mission would come out of Crowley’s commission, you were instead left tongue tied. As Dean’s brilliant green eyes cut off your words where he’d twisted in his seat to throw you one of those unfair boyish grins that always knocked the breath out of you.

Damn him and his… Everything.

“Nice work (Y/N),” He grinned. Still completely ignoring Crowley next to you, as his whole body radiated with the adrenaline of getting away more or less unscathed. By the time the two guys that had clocked you had time to share your descriptions with the rest of Evil Inc. they’d all be behind bars anyway.

“Of course! Did you ever doubt me?” You shot back, mirroring his adrenaline fuelled smile with one of your own. Now that you’d made it safely out of there, you were practically bouncing in your seat from the straight shot of energy to your veins that a good getaway always gave you.

“Yes… Yes we did. Several times… Actually, we doubt you most of the time,” Sam shot back as he focused on the road. Only looking away to send you that tried and tested shiteating grin that only little brothers had perfected through the rear-view mirror.

Yet, before you could throw some insults back his way, the proverbial elephant in the room decided he had to be the center of attention. Which honestly was nothing new. Sometimes you swore Crowley was a figment of your collective imaginations, and if he didn’t make you pay attention to him, he’d just fade from existence.

Though you knew that was all just wishful thinking on your end.

“She was… A vision. I offered her a job you know? With certain benefits,” Crowley shot in, sending you a sleazy wink.

It was his turn to ignore Dean. Pretending he didn’t see the daggers the trained mercenary was sending his way. The mobster was clearly playing with fire. If the look Dean was sending him was anything to go by, your hitter was only seconds away from ripping his spine out through his throat. And that was a very real threat when coming from the Dean Winchester.

Though, even with his death imminent so soon after you saved him, you didn’t like Crowley enough to warn him. As you instead resorted to just audibly gagging at his words in lieu of another no. Since the word didn’t seem to exist in his dictionary anyway. A visible shudder running through you at the thought of working for the mobster. You’d already been someone’s thieving little lap dog and you were done with that life thank-you-very-much.

“Ok, so the benefits can be negotiated. If nothing else, having someone who can remove a pair of handcuffs in just a few seconds could be very useful…” And though it seemed like he meant it like an actual offer, you weren’t an idiot. It didn’t really take a genius to hear the clear sexual innuendo in his words. The insufferable bastard just wouldn’t stop.

“She’s busy,” Dean shot back instead of you. As if he thought you were incapable of turning down what was clearly a bad job yourself. Hell, you’d rather work as a damn unpaid intern than get paid stacks of money to work for Crowley.

Which, actually…

Technically your current gig was unpaid. Some jobs just also happened to line your pockets when you were getting money back from the bad guys. They were bonuses, really, not a steady paycheck. So you really would rather work pro bono than for the figurative devil next to you.

“Not. Interested. I work for the good guys now, not scum,” You spat back, sending Dean a little smug smirk as if you showed him by shutting Crowley down. Which was the weirdest thing to be smug about, but hell… You’d had someone speaking for you every day of your life until you were 15, and you weren’t on the look out for a new puppet master. Not now, not ever.

“But bad is good! I don’t know why you reacted so harshly in there. You should embrace your bad side; the world loves a bad girl… I know I for one do,” Crowley hummed as you cringed internally. Damn it, you’d known he would try to use your earlier outburst of anger against you. But it still took everything you had to not let the panic show on your features as you instead rolled your eyes at him.

Ignoring Crowley’s endless ranting about how bad girls were the best thing since sliced bread, you instead turned to face Dean. Not wanting Crowley to repeat the words he’d said earlier, in case they would make Dean remember the gun range like you had, you kept your expression neutral as you spoke up over the damn mobster where he seemed moments away from composing an ode to wicked little women.

You wouldn’t let Crowley mess up any more of your day. Not just when everything seemed fine between you and Dean… Or even better than fine! They seemed back to normal.

“Dean… Can I borrow your gun?” Raising your volume to be heard over both the roar of the engine and the incessant chattering of your rescued damsel, you held your hand out and batted (Y/E/C) eyes at your hitter in mock innocence.

“Sure sweetheart,” Dean said without missing a beat, reaching across his body to unholster one of his many firearms, before stopping his hand midair right as he was about to hand you the loaded weapon. A raised eyebrow and soft smirk telling you he knew the answer to his question before he’d even asked it.

“... Why?”

“Let me shoot him,” You growled back, sending a head nod in Crowley’s direction as you tried to reach for the gun that Dean was keeping just out of your reach. The threat of violence finally shutting Crowley up as Dean shook his head with a chuckle.

“Not until after we finish this job (Y/N), and not in my car,” Sam shot in, not wanting to risk his older brother agreeing with you that violence was, as always, the answer when dealing with Crowley’s kind.

“Damn it… You’re no fun,” Pouting you crossed your arms and sank back into your seat like a petulant child. It was gonna be a long ride. And, considering you’d have to interrogate the Scotsman to find out how the hell he managed to get himself caught, it was shaping up to be an awful day.

So much for Charlie’s magical Princess Leia buns. The fates, and that sadistic bitch, mother nature, had once more decided tormenting you was their ultimate favorite pastime.

Oh joy…

Start Here - Last - Next (Coming soon)

Charity Heist: @foxyjwls007 @seppys-return-to-madness @stoneyggirl2 @ladysparkles78 @twinkleinadiamondsky @tmb510 @mimaria420

Dean Winchester Tags: @ria132love @woodworthti666 @defenderrosetyler @akshi8278 @justanotherwinchester @lyarr24 @torn-and-frayed @all-will-be-well-love @wearesuchstuff1 @thefridgeismybestie @adoptdontshoppets @screechingartisancashbailiff @septixtrash @punof-agun @deandreamernp @justagirlinafandomworld @sexyvixen7 @justrealizedimmascifygurl @globetrotter28 @deans-spinster-witch @iprobablyshipit91 @mrsjenniferwinchester @leigh70 @djs8891 @pink-sparkly-witch

#dean winchester fic #au!spn #dean au #au!dean winchester #tales89writes #hitter!dean #thief!reader #supernatural heist au #supernatural leverage au #spn heist au #dean winchester #supernatural #spn #dean x reader #dean winchester x reader #supernatural fanfiction #supernatural dean #dean winchester heist au #mercenary!dean winchester

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jawritter · 4 years ago

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His Old Ghost

Created For: @spndarkbingo

Summary: Some things from the past just never really want to let go, do they?

Square Field: Mobster AU

Rating: Explicit

Pairing: Dean Winchester x Reader x John Winchester

Word Count: 1672

Warnings: Heavy Trigger warning!! Suicidal!Dean, heavy suicidal ideals and implications as well as prompts, control, manipulation, talk of death past and present, depression, language, angst, I think that’s it. Sorry if I missed something.

Beta’d by @deanwanddamons! <3

A/N: As always please do not copy my work! Feedback is golden! This is the last fic for this Bingo! Hope you all enjoy!

**Masterlist** ~ **Become A Patreon**

The deep amber brown liquid swirled easily around the tumblr that Dean held tightly in his grip. His gaze was fixed on large rain drops falling against the window that was behind his desk, blurring the lights of the city that seemed to sit miles below his penthouse office on the 51st floor.

Below him were thousands of people, young and old, going about their daily lives, only worried about their own little bubble of problems. Most of them were unable to even see past the cell phone that seemed to captivate their attention as they moved about amongst each other.

With a disgusted snarl on his lips, Dean lifted the tumbler, and downed it in one pull. The burn of the alcohol has stopped affecting him a long time ago. Now it was the only warmth he felt..

“Those people, they’re ungrateful for what we do son,” John’s voice sounded from somewhere in the back corner of the room.

Dean had known he was standing there watching him. When you have lived many years with people trying to kill you, tend to heighten your senses in a way you couldn’t turn off.

“Get out of my head old man,” Dean’s voice drew out unamused. “I couldn’t give a fuck what they want or don’t want, see or don’t see. It doesn’t matter anymore.”

Dean could hear John moving closer to the desk, and the wood creaking attop it, as the smell of cigar that seemed to constantly linger around his father, misted with just a hint of some expensive Italian cologne and whiskey let Dean know he’d perched himself on the corner of the desk.

“If it weren’t for us, half of this city would be in ruin. Their businesses would be shut down, their schools and churches would be sitting empty, and they wouldn't even have a roof over most of their heads. Still, look at them down there, walking around without a care in the world, and you’re telling me that doesn’t bother you? Not in the least?”

In truth, it didn’t bother him. He wasn’t mad that most of them were ungrateful, and lived in blissful ignorance.In fact, he envied them. He wished he could walk around in the same happy little bubble they walked and lived in everyday, not knowing what really went on behind closed doors, or the sacrifices other people made at their expense. “It’s just good business,” or so his father always said. Dean was starting to beg to differ.

He hadn’t known when he’d take over his father’s ‘family business’ it would come with so much pain, and heartache or so much death. Now here he was, The Godfather, as it were, but it wasn’t anything like it was in the movies. No, it was darker, and colder, and lonely as the grave he’d seem to keep lowering his friends into.

He thought he could have it all when he was younger. He thought that he could have it all, ruling the city on his throne of control as the people moved about like his little pawns in a game of chess only he could master. He was wrong. So very fucking wrong, and now? Well, now he was just left with the ghost of the past.

“It doesn’t bother me,” Dean said with a slight shrug of his broad shoulders. John’s dark chuckle sounded from behind him as he got up and moved closer to the window, putting a hand on the cold glass as he watched the rain slip down the pane, determined to ignore the old demon that seemed to come and visit him after every failed job.

“Sure is a long way down isn’t?” John’s voice said from directly next to him now, as if he was looking down at the city below him just as Dean was now. “You know, it wouldn’t be hard right? The fall? In fact, it would almost be peaceful. Hell, they say by the time you hit the ground from this height your heart’s already stopped anyway, and you're dead before you even hit the ground. It’s as easy as falling asleep.”

Dean’s jaw clenched as he closed his eyes and fought against the thoughts that were clouding his judgement. “Fuck off,” he growled, but John just laughed in earnest, sending a familiar shiver down Dean’s spine.

“Come Dean, what do you really have to live for anyway?” John taunted, walking around him like a lion stalking down his prey, getting ready to land the deadly pounce that would ultimately destroy the poor, worthless beast that was weaker than he.

“She will never love you Dean, you know that right? First time shit goes sideways, she’s gonna do the same as every other bitch you have ever used to get your dick wet. She’s just there for the money you hand her, and you know it.”

John’s hot breath blew against the back of his neck as the next passing words were made in a whisper against his sweat damp skin.

“But, you had to fuck around and get feelings, didn’t you boy?”

“SHUT THE FUCK UP!” Dean roared, but it only seemed to edge on his torturer even more.

“No! Feelings make you weak, make you vulnerable!” John’s voice sounded louder than his own, and Dean flinched as if he’d raised his hand and struck him.

“I shouldn’t be surprised, you always were too weak. You and your feelings were the reason I’m dead today Dean. Sam would have made a better leader. He was smarter, stronger. You were never even able to protect him.That’s why you let him go off to Stanford, isn’t it Dean, because he’d be safer out of the life.”

Dean’s fist pounded against the glass in a hollow thud, and he gritted his teeth almost painfully, “Sammy deserved better than this. He deserved to get out.”

“Is that what Benny deserved today Dean? Was that round through the heart his way of ‘getting out of the life’.He’s in the ground right now because you sent him on that delivery Dean, he’s dead because of you.”

“I said, fuck off!” Dean growled, but to no avail.

“Do Y/N a favor. Open the drawer where you keep that 45, and end it. A simple shot to the temple and it’s done. She’ll be free of the coward that she’s tided too.”

Dean’s eyes shot to the small drawer at the bottom of his desk, and his pulse quickened.

“That’s it son, do it, end it.” John's voice growled deep in his ear, as one large tear rolled down Dean’s face.

His legs felt weak. His breath was coming in short spurts as a grip tightened around his pounding heart, like a vise in his chest. John’s voice repeated, growing in his ear to “end it, do it now.” the same tone he’d used his whole life to order him around, and Dean had never been able to disobey an order.

Maybe his dad’s ghost was right, and was weak. Maybe you would be better if he just ended it, took the cowards way out of this shit show, and let you move on. He’d make sure to leave you enough money to live comfortably for the rest of your life.You’d be better off if he were dead.

Before he could even move from his spot against the window, two hands, much smaller than the ones that felt as if they were gripping his throat, slipped around his chest, and your scent seemed to push through the fog of self hate and regret that was weighing on him from years past.

“Dean, baby breath, it’s okay,” your voice soothed over him, and he turned to lean into your embrace, thankful that you had come in just in time to once again chase the old ghost away.

“I know, it’s just one of those nights,” Dean murmured into your hair, letting the scent of his favorite shampoo that you always used calm his racing pulse.

“It wasn’t your fault baby. I can see you literally blaming yourself. Benny knew the risk of what he was going to do, he knew that it could go the way it went. You couldn’t have stopped it if you wanted to,” you try to sooth him.

Dean’s eyes flickered to the corner of the room, where a pair of glowing yellow eyes shone like cat eyes in a dark alley, and his father’s face disappeared into the darkness. He was never gone forever. He was always there, always lurking, always haunting, taunting him.

“Come on handsome, let’s get some sleep,” you tell him, grabbing his hand, and leading him from the dark, cold office to the master bedroom were you could keep an eye on him, keep him close to you, and help fight off the old ghost of his past that never seemed to want to let go.

Tonight he’d win against them again, but there would always be a battle, always a struggle with demons that had their hooks in him so deep, that one day they’d drive them to his grave. Tonight though, he’d hide in the safety of your arms, and your warm embrace to get up and do it all over again tomorrow. Until one day, by an enemy or by his own hand, he’d be lowered into the ground, and with a hero’s funeral to cover up a black soul that had more blood on his hands than the devil himself.

As long as he had you, and as long as you were here, he could find his resting place here. This was as close to heaven as he’d ever get, and when he’d died, and they covered him in gold, he’d be able to say he had you, for just a little while. For just a little while, he got to see heaven, and it was all because of you. His hiding place. His sanctuary. A place where his ghost couldn’t find him.

Forever Tags: @deanwanddamons @rvgrsbrns @bi-danvers0 @onethirstyunicorn @i-love-superhero @akshi8278 @lyss-dw79 @magssteenkamp @lemondropirwin @squirrelnotsam @hobby27 @spnbaby-67 @mrsjenniferwinchester @defenderrosetyler @screechingartisancashbailiff @thecreatiivecorner @aflamboyanceofgays @vicmc624 @busy-bee-angel-misska @justanotherwinchester @brilovesdeanwinchester @idksupernatural @lyarr24 @amandamdiehl @love-jackles-37-blog @miraclesoflove @Waywardsistershy @emoryhemsworth @dean-winchesters-gardian-angel @softsebastian @tatted-trina6 @deanmonandnegansbitch @hayleeharling @flamencodiva @coldmuffinbanditshoe @bxbyizzy @dirty-pan-goblin @itmejado @supernatural3002 @teresa-67 @thoughts-and-funnies @hearteyes-j2 @miss-nerd95

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heloisedaphnebrightmore · 4 years ago

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Not supposed to [Dean Winchester x Reader] - Challenge (18+) [Completed]

Summary: Dean is the head of mafia and you are a personal investigator following him to find information on him for a client. That is until you decide to act in a way you were no supposed to.

Status: Completed Pairing: Mobster!Dean Winchester x Reader Word count: 13.2k Rating: 18+ Warnings: Smut, kidnapping, blood, shooting, swearing, mention of murder Beta: @dreamer821 thank you :)

Challenge: [x] [x] I wrote this mini series for @deanmonandnegansbitch ‘s challenge. It was supposed to be a one shot of some kind, but there will be 4 parts to it after all, because I kind of ran away with the story line.

Supernatural Masterlist! | Masterlists!

If you enjoy my stories, please consider donating and supporting me on Ko-fi. Of course, it’s completely your choice, I will continue updating for free anyway :) Thank you <3

Chapter 1 - Not Supposed to pt. 1|4

Chapter 2 - Not Supposed to pt. 2|4 (14+)

Chapter 3 - Not Supposed to pt. 3|4 (18+)

Chapter 4 - Not Supposed to pt. 4|4 (16+) [End]

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itsthestutterforme · 4 years ago

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Forgotten 1/2 (Supernatural)

Summary: Y/N commits suicide and the Winchester tried to cope with her death. Jack refuses to believe it so he brings her back to life. He thought things were fine until he realized Y/N didn't have any memories of them.

Warnings: mentions of depression and suicide. Make sure you check in on your friends and family. You don't know what they're going through and staying quiet about it.

Characters: Jack x reader, Sam x reader, Dean x reader, Castiel x reader, Henry Cavill as Ruben

The bunker sounded quiet and lifeless without Y/N there. The past few months, she's been going through a rough patch with her. One day, the Winchesters came back from a week long hunt to find her in the bathtub with her wrists slit.

Dean pulled out her of the tub and wrapped her in a bed sheet because he knew that Sam couldn't see Y/N like that. He also know that Sam didn't have the heart to bury her, but the image of her pale, lifeless corpse was forever seared in their brains.

This happened a few weeks after Jack killed Mary and they are barely holding themselves together. Y/N was like a big sister to Jack, and when Castiel told him what happened to her he was heartbroken. He snuck into the bunker before they burned her body and transported her to a random warehouse.

He hovered his hands over her and snapped his eyes shut to concentrate all of his power to bring Y/N back to life. After a few minutes, your body jolts up and you gasp for air. "Y/N?" Jack says excitedly.

Your Y/E/C scanned the room of broken windows and brick walls starting to detierate. Your eyebroes furrow when you see a young boy staring at you happily.

"I'm sorry but.. who are you?" You asks. His smile falls and his eyes saddened. "What? You dont know who I am?" You shake your head and add, "No idea." "I need to call Castiel," he says slowly. His jaw clenched as he eyes focused on a random spot on the bed. He reaches into his pocket for his phone and dials a number.

"Please stay here," "Who's Castiel?" You ask. "Someone you care about you. Just please stay here until we figure this out," he says, clearing in distress. "Okay." He walks towards the doorway but doesn't leave the room. "Cas, something went wrong." "Jack, what did you do?" A man with a low, scratchy voice says.

"Y/N is alive. I brought her back to life before they could burn her body," Jack explains. Burn my body? Was I murdered? Is he my killer? You think to yourself. "You what?" "She's awake now but she doesn't know who I am and I don't know what to do." Jack says all in one breathe. "Okay, where are you?"

"I don't know, some warehouse a few miles from the bunker." Jack answers. "I'm on my way, just keep an eye on her." Cas says before hanging up. Jack's gaze fall on you and your heart starts to race.

He makes his way towards you and sits back down on the chair. "Don't be nervous, Y/N. I would never hurt you. You're like a sister to me."

"What happened to me?" "I think Cas is better at explaining that than I am." You cross your legs and push your hair back so it's out of your face. "Can I lay on you?" He asks. "What?"

You barely even know this kid, but honestly, he does look like a kid. A kid that's been through a lot more than he should have, you give in.

You let out a slow sigh before scooting over on the bed. The bed creaks with every movement and you were surprised it didn't collapse under you.

Jack sits down next to you and lays his head where your shoulder and chest meet. A soft sigh leaves his lips and there was a moment of silence before you hear a sniffle.

"You okay?" You say, looking at him. "I really missed you, Y/N. You're really important to me and I'm sorry I could be there for you when you needed me." He croaks. "Jac-" "Jack!" Castiel's voice echoes through the warehouse.

Jack stands up from the bed and says, "In here." Cas follows the voice to the room and stops when he sees your laying there, staring at him.

You stand up from the bed too and Cas rushes over to you. He takes you into his arms and you stand there awkwardly, letting your arms dangle by your side. "She doesn't remember who you are, remember?" Jack says. Cas pulls away, wiping away some of his tears. "Right, I forgot about that. Sorry," Cas says to you.

"That's okay," you say with a soft smile. Cas matches your expression and his eyes fixated on yours, like he was having a conversation in his mind. "Her not remembering us may be for the best, Jack."

Cas looks over his shoulder at Jack. "What? No, I need her. We need her." Jack explains. "This life had already taken enough away from her. She needs her life back."

"You love her. How can you let her go?" "Sometimes, you can love someone so much that you know letting them go is what's best for them," "We just got her back." Jack says, on the verge of tears. My heart sank into your chest.

"Name the place, and we'll take you there with a snap of our fingers." Cas says, returining his gaze back you. You glance over a Jack and say, "A road trip doesn't sound like a bad idea."

"He's just a kid, Castiel. He needs emotional support," you add and a small smile tugged at his lips. "What?" "You're sounding to act a little but like yourself," he explains. You exchange a smile and Jack asks, "What about Sam and Dean?" "I'll handle it," Cas says.

It's been two months since Castiel and Jack dropped you off in Chicago. You had enough common sense to live in a city, and there was something drawing you to Chicago. But you have no idea what it was.

One night you were walking out of the subway to walk a couple blocks from your apartment. You were grabbed and dragged into an alleyway. A hand was pressed to your mouth and you stared into the eyes of a fairly attractive man.

His navy blue eyes search yours and he moved his plump, pink lips to whisper, "Don't say scream or making any noise. You're being followed."

He pulls his hand away and looks over at the sidewalk you were just walking on. His has a well groomed goatee and get black hair that is combed to the side in a thick swoop to the right.

He looked like a classic mobster. He even has the black trench coat and all and you eye him suspiciously. You look to the sidewalk with the shadow of a large figure grows closer.

Your heart is racing but nothing is telling you to run. Everything is telling you to fight. The man was still relatively close to you and not moving. "What are you doing?" He leans in closer and crashes his lips onto yours.

He cups your cheeks and tilts his head to the side to gain more access to your mouth. Your body plattens on the brick wall and footsteps walks passed the alleyway.

The man finally pulls away and you lift your leg to kick him away by the solar plexus. He falls flat on his back and you say, "What the hell was that for?" He up from the ground and said, "You're a tough broad, aren't you?" "Damn straight. You pull anything like that again and I'll do alot more than kick you."

You hear a woman's shrill and the hairs stand up on the back of your neck. You rush into the alley way and run towards the sound of her screaming. You slide to a stop to see a man trying to drag a woman I to the alleyway.Your eyes scan around for a weapon and you find an iron poker. Thank God you have your tetanus shot.

You keep a tight grip on the rod and swung the rod at the arm. The man grunts in pain and let's go of the woman. "Run," you command. She looked at me reluctantly. "It's alright." She shakes her head and says, "Girls support girls." She pulls out her pepper spray from her purse and we both turn our attention to the attacker.

He was still cradling his arm and when you take a step towards him. He stumbles backwards and says, "I-I'm not looking for any trouble." "Oh, I thin-"

"You okay, darling?" Your boyfriend, Ruben, asks. He walks up behind me and slides a hand down my arm. "Yeah, just think about how we first met," "Oh you mean when you kicked on my ass like a rag doll?" He teased as he sat down across from me.

"To be fair, you kissed me randomly and I didn't know who you were. And the guy that attacked Y/F/N worked for you."

"Well can you blame me? You're drop dead goregous and I wanted to know what you were made of." "So you tried to attack me?" "You can learn a lot about someone by how they fight. Most girls either run away or fight to run away. You fight to protect others." "And that's when I knew I had to have you." He adds, tapping his thigh for you to sit on.

You stand up and sit down perpendicular to his body. His hand trails down to your lower back and presses his lips against yours in a soft kiss. As the kiss intensifies, his hands fell lower and lower down your leg.

He pulls you so you're straddling his lap. He grips your ass and your roll your hips a little, making him moan. Who knew that you would end up falling for a mobster?

You've grown quite used to be Ruben's right hand woman. He made me in charge of the tactics and strategy because you have strength in planning and preparation. You were in the middle of planning for a drop off and pick up back while Ruben was out conducting business.

You hear a loud struggle and grunts. You look up from your notepad to see some henchmen walking a taller man into the red room. All of them were bloody and disheveled from fighting. "What happened to you guys?" You say as you approach them. "Y/N? You're really alive?" The man asks.

"How do you know me?" You ask. "He doesn't. He's just trying to save his ass because he knows he's going to meet his maker," one of the henchmen says.

The man reaches and touches your face. You gasp in shock of his warm, calloused hands but you only felt it for a second before he is shoved to his knees. One of the henchmen pulled out his gun and cocks it.

"Hey, trigger happy, put the gun down " you command. "Boss says to kill anyone who interferes with our business. We found him tearing one of our warehouses apart."

This man's touch feels familiar and something tells me to let him live. "Let him go," you state. "What?" "Did I stutter? I said let him go." He puts his gun away and you help the man up.

"Look, I don't know you, b--" "Dean. My name is Dean." He interupts. "Dean, you need to leave Chicago and never return." His hazel green eyes scan your face and he nods. You motion to the door and he says, "I'll always love you, Y/N." You two lock eyes for a moment before he walks out of the door.

"Boss will-" "I'll tell him what happened, don't worry about it." "Worry about what?" Ruben says, making the henchmen jump. "Privacy," you tell them and they all walk away. "Worry about what, baby doll?" "One of the warehouses was trashed," you say with a sigh.

You walk into your office and lean against your desk. "Did they find who did it?" "Yes," "Did they toss them in the red room?"

"No," you say. You eyes dart away from his gaze and he asks, "Why not?" "I knew him." "Y/N, you made a vow to not let personal affairs mess with business."

"I know, okay. I'll pay whatever price. I'll pay for the damages out of my own pocket and go to the warehouse to cl-" "You're going nowhere near that warehouse," "Come on, baby, talk to me." He adds, sitting next to you.

"Remember how I said that I had a life before I went to Chicago but I didn't remember it," "Because of your head trauma, yeah." He answers.

"I think he knew me before then. He knew who I was but I had no idea who he was. All I know is that his touch was familiar an-" "Wait, he touched you?" His jaw flexed and he stands up from leaning on the desk.

"Y-yes, but only for a second." "He's a dead man," "Ruben, please," you say, standing between him and the door. He steps so close to you that your chin gently grazes his chest.

He lifts your chin so you are looking straight up at him "You're mine, you know that right?" "Yes," you say softly. "We're going home," "But what about the tactical plan f-"

"You can finish it at home after I edge you for an hour," "Damn it," "Should've thought about that before you let him touch you,"

An unknown number has been calling you the past few days. Ruben always warned you about answering calls from unknown numbers.

Since you were a part of his business now, that put a target on your back. You had to be vigilant and careful with your words. You never know how is watching or listening.

The same number called you for the fifth time today and you slam on the answer button. "Hello?" You answer. "Hey, sweetheart," Dean deep, velvety voice says. "Dean, what are you doing?"

"You're in danger, Y/N. We're coming to get you," "First of all, I'm Nuben's girlfriend. I'm always in danger. Second of all, no you're not because they have a shoot to kill order on you."

"I don't care, Y/N. Lucifer is after you and we're not sure why," "Lucifer does not exist outside of the bible. "You're wrong about that, sweetheart." "Stop calling me sweetheart," "You have to believe us, Y/N. You're life is at stake here. If Lucifer finds you, you and your little boyfriend is a good as dead."

His words echo in your head and your mind started to disassociate. Series of images flood your brain and there was a sharp pain in your head.

You hiss and drop the phone on the floor as you hold the sides of your head. Voices of different people you've never hurt before echoed in your head and images of a man with dirty blonde hair and stained t-shirt and jeans.

His eyes glowed a crimson red and with the snap of his fingers, he could make a person's neck snap of their entire bodies explode. Then some images of you and Dean came into mind.

You were laying next to each other talking about something and he kisses you. Then the images were gone and you looked around frantically. "What the hell was that?" You say to yourself.

#dean winchester x reader #dean x reader #sam winchester x reader #sam x reader #castiel x reader #jack klein #henry cavill #henry cavill x reader #mobster #mobster!henrycavill

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holylulusworld · 5 months ago

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Wrong House masterlist

Summary: You are in trouble and need fast cash. For the longest time you tried to be a good girl, now you need to break the rules all over again.

Pairing: Mobster!Dean Winchester x Thief!Reader

Warnings: angst, language, breaking and entering, criminal reader, mafia au, implied sexual harassment (not Dean), threats, scared reader, kind of hostage situation, more to be added

Wrong House (1) 💔

His House (2) 💔

A big house for a lonely man (3) 💔💕

Our house (4) 💔💕

A home, not a house (5)💕

#dean winchester #dean x reader #dean winchester fanfic #spn #dean winchester x reader #dean winchester x you #mafia au #mobster!dean winchester #Wrong House masterlist

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superfanficnatural · 4 years ago

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The Ultimate Betrayal Teaser

Pairing: AU Mobster!Dean Winchester x Reader

Summary: When a rival mob boss decides to show up in your town to claim their stake, you and your partner, Dean Winchester, band together to claim your territory over your city. When sudden and unexpected motions are set in place, who will be the one that gets betrayed?

A/N: This is the “teaser” for a new mobster AU I’m going to start writing. If anyone would like to be added to the tag list, please let me know! As always, I hope you enjoy!

Warnings: Smut, 18+ NSFW, Oral Receiving (Male), Choking, Breeding, Rough Sex, Spanking, Dirty Talk, probably some others that I can’t think of.

Word Count: 2,967

Masterpost

“I want that shipment of weapons ready for tomorrow, a new rival gang has claimed territory in my town and I want them dead!” you shouted to your workers.

Everyone was moving around the warehouse, preparing the M4A1’s for the meeting at the docks tomorrow. A new mob boss, going by the name of Dick Roman had decided that he wanted to play with the big boys in the city. That being you and Dean Winchester, the kingpin of the drug trade in Kansas. You were rivals at first, your weapons against his drug business. But eventually, the two of you came to an understanding that the two of your businesses combined would be stronger than they would be at odds.

“Ma’am, we have received word from the Winchester, he would like to set up a meeting tonight,” your right hand man came up to you.

“Sounds good, Benny,” you thanked, a small smile lighting up on your face.

Benny had always been a close friend of yours and probably one of the only people to see your soft side. You didn’t allow anyone else to see that side of you, for weakness meant death in this business.

“I’ve arranged a car for ya cher, we’ll be leaving in an hour,” his southern accent flowing into your ear.

“Benny, I told you not to call me that in front of other people,” you softly scolded.

“Sorry, ma’am,” he returned to his professional demeanor.

You clasped him on the shoulder, “Dark times are ahead, we need to make sure that we are on top of everything so we can be ready for whatever Dick Roman does.”

You walked past him and went into your office, closing the door behind you and sitting on your chair, letting out a sigh. You knew that these next few weeks wouldn’t be easy, between keeping relations with Dean and dealing with Dick Roman, you were going to be busy. Picking up the phone and dialing the number, you put it up to your ear, hearing the ringing of the line before the recipient answered.

“Is there a reason you’re calling me?” a deep timbered voice greeted in your ear.

“What’s up with this meeting you called me for?” you responded, sounding unimpressed.

“Do I need a reason to see my partner?” he drawled.

You could practically see the smirk on his face, “Need I remind you that we are doing business together and nothing more?”

“Always work and no play with you, why don’t you just relax? I know I could help with that, I did last night,” he quirked.

You cleared your throat and tossed the memories that threatened to arise at his words aside, “That was just business, as always. Now, what’s the reason for our meeting?”

He sighed, “We need to discuss matters about what we’re gonna do with Dick Roman.”

You sighed as well, “Very well, I’ll be there shortly.”

“Make sure you wear that outfit that just makes me wanna-” You hung up the phone before he could say anything else.

You found yourself pressing your legs together for desperate friction, the memories that had once subsided floating to the surface of your mind. Shaking it off, you ignored the sweet touch you were craving and got back to organizing everything for the shipment you had tomorrow. Double checking the boxes and making sure everything was in order, you cleared everyone from the assignment and turned to see Benny walk up to you.

“The car has arrived, ma’am.”

Following Benny, you got into the black Ranger Rover that was exclusively yours and told the driver to take you to Dean’s compound.

“You excited to see Dean?” Benny asked from beside you.

You turned to him with a straight face, “We are doing business, nothing more and nothing less.”

He chuckled, “I think your definition of ‘business’ is different than mine.”

You slyly smirked, “Oh? And your ‘business’ with Cas is just the same?”

His eyes widened in shock.

“What? You didn’t think I knew?” you chuckled.

He kept opening and closing his mouth, trying to figure out what to say but was failing miserably.

You clasped your hand on his shoulder as you did before, “Look, if you’re happy, I’m happy.”

That seemed to put him at ease as he sighed and slumped back into his seat. You laughed for a bit until the car eventually came to a stop, signaling your arrival. Getting out of the car, you were met with the city lights and crowded streets of people walking by, the refreshing air being sucked into your lungs. You were greeted at the front door of his establishment, The Divinity Nightclub, by some of his guards, them opening the door and allowing you to enter. Once you walked in, you took a look around to notice the flashing array of lights going throughout the building, music blaring through the DJ’s booth as what seemed like hundreds of people on the dance floor. You and Benny walked around the dance floor and towards the door in the back, walking through to see a viewing area with chairs surrounding the edge, a pole on the center stage. It was his more VIP access room, where strippers came out to men with money wafting out of their pockets. Rolling your eyes at the scene, you continued to walk by to the door at the back left side of the room, opening it to see the stairwell that led to the second floor, Dean’s operation.

Ascending the stairs, you were met with men walking around in gas masks and quarantine suits, tables with lights above them shining onto many different products. Meth, Cocaine, Marijuana, and many more drugs sitting on their own respective tables. You walked to the left and knocked on the door to Dean’s office and waited for someone to open it. Cas, Dean’s own right hand man, opening the door for you a few seconds later.

“Hey, Cas, how you been?” you brought him into a hug.

He returned your hug, “Nice to see you, Y/N. I’ve been good.”

Once you pulled away, you saw him make eye contact with Benny behind you and a slight blush arose on his face.

Chuckling, “Why don’t you two go ‘talk’ while me and Dean discuss business?”

Cas looked back at Dean sitting in his chair, silently asking for permission. With a simple nod from Dean, the two of them exited the room, you and Dean remaining. You took a minute to notice the complete contrast of the interior of the room versus what goes on in the other. While both were clean, this room was much more modern and relaxed, the smell of drugs not wafting inside, only Dean’s cologne and natural scent filling the room.

You sat down on one of the chairs across from his desk and crossed your legs together, your dress hitching up your thighs, the action drawing Dean’s dark gaze.

“So, you wanted to talk about Dick Roman?” you tried not to smirk.

He cleared his throat and brought his gaze back to your face, “I’ve gotten word that he’s been organizing something big, and he’s going to make his move soon.”

“And you’re sure this information is accurate?” you narrowed your eyes.

“Yes, I’m sure,” he gave a fake smile.

You huffed out in annoyance, “Dean, at least act professional.”

He smirked and stood up from his seat, walking around the table to lean against the front of it, his crotch a few feet from your face, “You’re always on about professional this professional that. Wanna know what I think?”

You raised an eyebrow.

He got up and lowered his face, his lips mere inches from yours, “It’s just a facade. What you really want is to get down and dirty, completely unprofessional.”

You cleared your throat, “And what makes you think that?”

He smirked, moving his mouth to your ear to whisper huskily, “Because you’ve been aroused ever since you walked in here.” He slowly licked a trail underneath your ear, sending shivers down your spine, “I also know you’re wearing the outfit, the one I wanted you to.”

“Don’t kid yourself,” you attempted to speak in a strong mannered tone but the only thing that came out was a rasped whisper.

You could feel the juices begin to build up within your sex, your body becoming lax and your brain becoming hazy from his deep voice.

He suddenly pulled away and walked around back to his desk, sitting down in his chair and intertwining his fingers, “Let’s get down to business then.”

He knew exactly what he was doing and you were having trouble staying professional, your eyes focused on nothing but him, soft pants leaving your lips. You shot up out of your chair and shimmied out of your black dress, your sexy black lacy thong and bra popping into view. Dean’s eyes dilated and his once self-satisfied smirk turned into a dark look, a predatorial hunger rising within him. Slowly stalking over to the other side of the desk, you looked down at Dean to see him looking at you with nearly pitch black irises. Smirking to yourself, you slotted yourself onto his lap, his thigh in between yours.

“Is this what you said I had wanted?” you seductively whispered in his ear as you left a kiss there, slowly riding yourself on his thigh. Your panties were already completely ruined and the juices from your pussy were beginning to leak onto his pants, a dark wet spot appearing on them.

“You’re lucky I don’t give a fuck what happens to these pants right now,” he gritted behind his teeth, grabbing your hips and harshly rubbing you onto his thigh.

Your mouth parted and a keen whine escaped from your lips, Dean roughly pressing his lips against yours. Ever since he had mentioned the night before on the phone, you were riled up and were desperately seeking your release. Now, you were going to take it.

“So good to me, Dean,” you breathed into his mouth, riding along his thigh.

“Ever since last night, that sweet cunt has been on my goddamn mind,” he grunted, sucking deep bruises into your neck.

You wanted to cum riding his thigh but you were too eager, peeling his hands off of you, you rose up and reached down to unzip his pants.

He was about to pull them down his legs but you stopped him, “Keep it on.”

You smirked and reached your hand in through the hole, pulling out his cock, “Commando, really?”

He smirked goofily, “Had a feeling this was gonna happen, wanted easier access.”

You rolled your eyes and got onto your knees in front of him, looking into his eyes as you left a kitten lick on the tip of his head. His lips parted and his face had a rose color to begin to tint his cheeks. Your eagerness got the better of you once more as you took him wholly into your mouth, wasting no time to instantly begin bobbing your head along his shaft.

“That’s a good girl,” he wrapped his hands into your hair to move it out of your face so he could see you easier.

His praise exhilarated you and you decided to try and make him feel as good as you possibly could. You took him down to the base, his pubic hair tickling your nose as his musk invaded your nostrils. Moaning at his taste and smell, you continued to deep throat him, pulling back until the tip was in your mouth and moving your head back down. His moans and grunts were like music to your ears as you continued to pleasure him.

After a few more minutes, he suddenly grabbed you by the arms to pick you up, “If you keep doing that, I’m gonna cum.”

“That’s the point,” you mocked.

He smirked, “There’s something else I wanna fill up right now.”

He loosened his tie and took it off of his neck, holding it in one hand as he used the other to turn you around and bend you over the desk, using that very same hand to bend over your back. He ripped off your panties and groaned at the slick wetness that registered in his eyes.

“Fuck I’ve missed this pussy,” he growled before shoving his cock right into your cunt.

“You had it yesterday,” you half spoke, half screamed as his intrusion left you breathless.

“Shut the fuck up,” he growled, circling his tie around your neck and using the long rope to hold onto as he pounded into you.

“I’ll use this pussy whenever the fuck I want, wherever the fuck I want.”

You were too busy trying to keep your screams as quiet as possible to even think about retorting. His thick cock was stretching you incredulously and it felt like he was reaching into the deepest parts inside of you. It was as if he was pushing against your cervix, your sweet spot being completely and utterly satiated.

“Shit, Dean!” you choked out, your breaths being forced out of your body with each thrust, the tie around your neck squeezing just enough.

You could hear his slight chuckle behind you, “You’ve missed this cock haven’t you? Missed me filling you up and having you scream out my name.” He pulled you up so your bodies were connected, “Missed having me fill that sweet cunt with my cum.”

He pushed you back down and pulled even tighter on the fabric around your neck if that was even possible, your back arching as he continued to ruthlessly force his way inside of you. The tightness around your neck was making it slightly difficult to breath, but it only heightened your senses, the veins and crevices of his cock inside of you brushing up against your walls in a manner that had you desperately trying to hold off on your release. His moans were reverberating throughout his chest and ultimately reached his thick shaft, vibrating your insides delightfully.

“Fuck it’s so hot to see you like this, all strewn out across my desk, silently begging for more,” he grunted, slowing his pace to slow, hard ruts. “I know a good cockslut when I see one, and the second I saw you I knew you were going to be begging for this cock.”

You were never one to beg, or to bow down to another person. Hell, if you weren’t in this position you would probably be ordering him around. But when it came to the bedroom, Dean was in control, and there was nothing that you could do about it. Something about him brought out your inner darkest desires and you were hopeless in ignoring them. You wanted to beg, but you weren’t going to give up so easily.

“Maybe if you could fuck me better you wouldn’t have to compensate with that mouth,” you choked around the tie.

He chuckled, “Oh, is that so?” he shoved his cock in completely, pulling a whine from your lips.

“Maybe I’ve been too generous, it seems like I’ll have to make you understand where your place is, babygirl,” he growled, slapping your ass with his free hand, hard.

A shout fell from your lips but it was short lived as he cut off your oxygen supply by squeezing tighter on the silk. Your back was arched completely as your head was nearly touching his chest, his hand repeatedly finding its way back to your ass, slapping it feverishly. After around six slaps, you were dripping all over his cock and your ass was raw.

“I knew you’d like it, hell, you like anything that I can give you, don’t you my little cockslut?” he smirked.

You were desperately attempting to hold off on your orgasm, knowing you had to have his permission to do so. The room was filled with the sounds of the slapping of his hips onto yours, your choked cries and his primal grunts, the smell of sex in the air.

His grunts and groans were getting louder and his hips were becoming sporadic, “Fuck I’m gonna breed this sweet cunt, you wan’t to cum, don’t you sweetheart?” he grinned, pulling your back up to his chest and reaching a hand down to play with your clit. “Beg me for it,” he growled into your ear, not faltering in his movements, your pulsing sex essentially begging for release.

“P-please, Dean,” you begged.

“Please what?” he pressed.

“Please let me cum, sir,” you relished him the title.

He moaned incredibly erotic in your ear after your words registered in his mind, “Cum,” he growled, pumping his hips twice more and emptying his seed deep inside of you.

The feeling of his warm cum coating your insides and his fingers on your clit drove you into your climax, screaming out his name as you gushed all over his fingers and cock. After a few moments of the two of you catching your breaths, he slowly pulled out of you and moved out of the way so you could move around the table and grab your clothes.

“Do you have a cloth?” you asked, wanting to clean up the mess inside of you and around your thighs.

He smirked, “No, I don’t. Guess you’re gonna have to walk around with my cum inside of you babygirl.”

You felt a shot of arousal course through you at the thought but didn’t make it obvious to him, instead rolling your eyes as you put on your clothes. Dean was just about done buttoning up his shirt when the two of you heard shots coming from outside of the room, Cas and Benny bursting in.

“We’re being attacked.”

Forevers Tag List: @magssteenkamp @shadowsinger11 @donnaintx @flamencodiva @impala-1979 @talesmaniac89 @winchest09 @malfoysqueen14

Dean/Jensen Forevers Tag List: @akshi8278 @jensengirl83 @lyarr24

Female Reader Tag List: @punof-agun @emoryhemsworth

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spnfic-search-blog · 4 years ago

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hey I was wondering if you can please find this dean x reader series where dean is in the mafia and the reader is a waitress. they meet eachother at the restaurant she works at and she catches his eye, and then they start going out. I don't remember much but I do know that the reader has a best friend that also works as a waitress and that in one chapter the reader gets warned by a lady at a party that dean is probably just going to use her, but that's not true. thanks!

Im sorry nonnie I was unable to find this in the allotted time. Hopefully someone can link us to the correct fic.

For any followers if this fic sounds familiar please add to the post so we can find this fic for Nonnie

#spn fic search #dean winchester x reader #mobster!dean #possibly mob boss au #waitress!reader #best friend is a co worker #multi chaptered #party scene #anonymous

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waywardsummoner46 · 3 years ago

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Five Years Can Change a Person

Summary: Five years ago, your life changed forever. Five years ago, your house burnt down and with it... your family. No matter how over-bearing your brothers were, you loved them nevertheless and their loss affected you insanely. Now content with your new family though, seemingly moved past the past, the ghosts of your brothers walk into the bar. How are they alive? How is that possible? You tried to wrap your head around it but are they the same as they were?

Word count: 2643

A/N: Hello! I am so sorry for my inactivity. I can’t say it won’t continue but I’m definitely out of my writing block. I’m currently working on the next part for Welcome Home, Sister, a Paul Atreides x Reader fanfic and a character list to help you guys get a feel on who I write for. As always, I hope you enjoy and let me know what you think :)

_______________________________________________________________

As a sixteen year old living independently in Lebanon, you sometimes struggled to make it through the day.

It’d been this way for five years but you never like to dwell on the past. After the incident, you’d been a lone wolf and even though it came with the weight of Hell to carry, you wouldn’t have it any other way.

Take today for example, you’d been to school and had a maths test. Somehow, you’d had full marks so you’d been proud of yourself but this one kid in your class was having none of it.

You’d heard of pick me girls before and she was no different. When your teacher had given you your test back, you’d sat there in shock just staring at it incredulously. She obviously noticed this, but misinterpreted this as you having a shit score.

So she sauntered over to you, fully prepared to degrade you in front of the entire class but when she noticed your actual score the emotions that filtered across her face were nearly enough to render you hysterical.

She’d blinked fervently at your paper, before turning and lifting a hand up to the teacher. “Um, sir? I think you marked her test wrong.”

The teacher paused in his stride and blinked blearily at her. “Melissa, (Y/N) had full marks fair and square, you, however, did not. So get back to your seat and be quiet.” You loved your maths teacher.

Melissa was having none of it though. She huffed like a petulant child, “Yeah, but there’s no way that she got better marks than me. Like there’s actually no way.” She kept listing the reasons why you were destined to be beneath her until she realised he’d stopped paying attention to her, along with the rest of the class.

She sat on your desk and leant down to your face. You raised a brow and quirked your head sarcastically.

“This isn’t over, bitch. Don’t think for even a second you are better than me. Beat me in another test, and I'll humiliate you so much, you’ll have to leave the school out of embarrassment.”

This was something you heard everyday but you ignored her and chose to focus back on your test. Flipping through each page you briefly glanced over how the teacher marked it.

You were about to shut the test completely, but you noticed someone had scribbled something on the side of your page. You knew it wasn’t you because it wasn’t your pen colour, either way you concluded that it was probably your teacher or Melissa that put it there. It was insignificant anyway.

After that entire fiasco, you’d left school and walked for an hour before you reached where you work: Harvelle’s Roadhouse. It was a bar run by Ellen Harvelle and her daughter Jo. You got along amazingly with both of them as they were the closest thing to a family you had and you cherished them with everything you had.

Most of the time, you refused to think about life before you were eleven but soon it would be the anniversary of the Harvelles and Ellen’s husband Bobby taking you in off of the streets so in a way, you were obligated to at least consider getting a card or getting some cake or something. Reluctantly though.

Whilst they’d never pried further about your situation since the night they found your smaller self, crying and aimlessly wandering on the streets of Lebanon, you knew that every year their curiosity became harder to contain but still they resisted.

The bar was quite out of the way actually, it was found on one of the roads near the motorway but not obvious enough that it was overpopulated. It was pleasant.

Admittedly, it was quite run down but you preferred the more homey feeling it gave off.

As you approached the bar, you took the time to study the sign. At night it glowed and made the building look ethereal.

You’d always been fond of how it resembled Ellen and Jo’s personality in a way. The font and the way it was built was unique and strong as hell, similar to the Harvelles

Blinking out of your odd thoughts, you gazed towards the open door and noticed Jo leaning against the frame drying a glass with a towel. “You alright, (Y/N)?” she nodded to you.

A fond smile made its way to your face and you increased your speed then engulfed her into a hug and squeezed.

“Yeah, I’m alright. You and Ellen okay?”

She wrapped her arms around you as she maneuvered which hand was holding what, sensing you needed comfort. “We’re both fine. You’re the one who seems off,” she said and let you go.

You brushed her off and entered the bar, Jo following behind you. “I’m good, seriously. I got full marks on the maths test!”

“Well, I’m glad. You revised damn well hard for that too,” Bobby suddenly appeared from behind the bar. Your grin widened and you ran at him and engulfed him in a tight hug. “Hiya, sweetheart.”

“Hi Bobby.”

Ellen came up from behind you then and joined the hug. “Don’t I get a hug too?”

You leaned your head back against her and sighed happily. You saw Ellen and Bobby as either your substitute parents or grandparents, honestly it depends on the situation. Jo, you undoubtedly saw as your older sister, there was no debate about that.

“Course you do.” You all broke it off and after some quick exchanged pleasantries, you got changed and went to start working on calculating the profits. Numbers just don’t seem to want to give you a break today.

___________________________________________________________

Five years ago…

In your family, there was you, John, Sam and Dean. John was your father but you’d always held disdain towards the man (always being since you were six) but Sam and Dean worshipped the man.

Sam argued with John on occasion but was overall very obedient. Dean though, was basically mindless, John’s perfect soldier and this grated you endlessly, but you said nothing for years.

Dean was twenty years older than you and Sam was sixteen years older, nevertheless they were both severely over-protective of you. They could be quite scary sometimes actually, so you learnt early on to suit their standards albeit begrudgingly.

John Winchester was a very powerful man. You didn’t realise the extent until that fateful day.

He’d brought Crowley, an equally powerful man over to your family home that your dad had rebuilt after your mother died in the house fire ten years ago. Crowley had always seemed interested in you and seemingly despised your brothers, this put both of your brothers on high alert.

When the doorbell rang signifying Crowley’s arrival, Sam and Dean’s gaze turned murderous. You were all sitting at the table, and you were enjoying your cereal when your brothers grabbed a shoulder each and hoisted you up into the air.

You squeaked out a protest. “Hey! Lemme go!” Dean took hold of your entire body and pressed you tightly to his chest. “Dean, I’m eleven. I’m not a kid anymore!”

He ignored you and carried you up to your room with Sam following closely behind. You thrashed and twisted violently in his arms but he was having none of it and tightened his grip on you.

“Dean, get off of me!”

When you reached your bedroom door, Sam went ahead and kicked it open. Dean walked in and dropped you on your bed leaving you scrambling to compose yourself. ”Come on, did you have to?”

He squatted down to your level and had a pitying look on his face. Extending his arm, he began brushing your cheek with his thumb.

“You don’t understand at the moment sweetheart, you’re still too young, but that man is dangerous and Dad needs me and Sammy to be there with him and for you to be safe,” he chided as though you were an infant. You didn’t give him a verbal response however your mood was accurately represented on your sour facial expression..

He upped and went to leave but waited for Sam who was lingering.

“We’ll only be half an hour, (Y/N). Read the book I bought you for Christmas if you want.” Then he, too, went and left you in your displeasure.

They shut the door softly but the evident sound of the over-sized lock they’d installed outside of it shook you to your core. Yeah, your brothers were definitely over protective.

Begrudgingly, you reached for the book Sam bought you that you’d chucked on your bedside table and started reading the back.

You began reading it and leant back against your bed but grew bored after the second sentence. So ultimately, you huffed loudly as if something entertaining might unravel… but your wall remained dull.

Then you started hearing voices. It was quiet at first but grew quite loud.

You heard your dad shout, “You are not having my daughter, Crowley! This is non-negotiable.” Wait a minute, were they talking about you? This can’t be good.

A faint mumbling was heard before a gun was unmistakably loaded and you gulped loudly. Glancing towards the picture on your wall, knowing what you’d have to do should things escalate.

And by the sounds of it, they were. One gun shot rang through the silence, followed by another then fifty more.

Apparently Crowley had brought his entire gang, probably predicting your father’s refusal to his ridiculous deal but his stubborn attitude was having none of it.

“Get your sister, now! Benny, Garth, you're with me!”

You heard two sets of footsteps sprinting up the stairs and your door was ripped open. Your brothers stood in the doorway and just froze. Their mouths open and eyes wide, before they dropped to the floor.

Out stepped Crowley, draped in an expensive looking suit with a broad smirk on his face. “Hello, (Y/N).”

You gulped and looked at him in fear. Calculating where the picture was behind you, you began to back away, discreetly edging towards it. Crowley seemed to relish in your terror and his eyes seemed to sparkle with something akin to malice.

He took a step forward, narrowly missing Sam’s head. Taking two steps backwards, you felt how close the wall was.

“You know, I would’ve thought you’d have been happier to see me, darling!” he exclaimed. “Moose and Squirrel certainly were not very happy, but when have you ever been similar to them?”

You squinted at him. The difference between you and your brothers was a sore subject for you. Being treated like a delicate antique compared to how rough and trusted your brothers were, grated you endlessly. Crowley, being the manipulative cow he was, had taken notice of this and understood that if he played his cards correctly then many things could work out in his favour.

You took another step back and pressed up against the wall. Edging your fingers behind you, you slipped them underneath it and grasped your gun. Fingers shaking you pulled it out.

“The only thing I’ll be happy about is when you’re dead, Crowley.”

You aimed, and shot. His eyes widened momentarily and pure fear crossed his face before he fell to the floor, grunting in agony.

There was still commotion downstairs but it didn’t seem as though any of your family had died. Prioritising your brothers, you rushed towards them and knelt down to them on the carpet.

You pushed your fingers up under their necks and checked for a pulse.

They were faint, but definitely present and you heaved a choked sob of relief.

Sam stirred then and glinted up at you before his eyes widened. He sat up abruptly, ignoring the throbbing headache he had and grasped your shirt tightly. “You need to leave! He’s rigged a bomb, the house will blow up.” Staring at him incredulously, you said, “Sam, what? Crowley’s dead! I shot him! He’s gone! He can’t have placed a bomb before entering the house, we’ve all been here!”

He shook his head and drew your foreheads together.

“(Y/N), you need to leave. Jump out of your window and climb down the ivy and run as fast as you can, anywhere away from here.” He pushed you with all his might back into your room. He stood up and towered over your quivering form on the floor. “I love you, Dean loves you. We’ll see you again, just don’t forget us.”

He faced Dean and slapped him. Dean woke up sputtering. Once he’d calmed down, hee faced Sam and seeing the look in Sam’s eyes, he understood what needed to be done. Tilting his head slightly, he saw you looking on with horror and mouthed “I love you.”

Then they were both up and reloading their guns before storming back down the stairs.

You sat there for about five seconds before you determinedly went to follow them but arms wrapped around your waist. “Come on, sugar. Let’s get out of here”

Gabriel tightened his hold on you and held a rag up to your nose. “Sh, sh. I know, sweetheart. I’m so sorry but this is the only way.”

Panicking did nothing to help you, but your frantic breaths seemed to draw more chloroform into your lungs and you inevitably found yourself becoming more drowsy before everything went black.

_______________________________________

Waking up, you noticed how your head was on Gabriel's shoulder. Then you noticed how the air smelt of smoke and you wrinkled your nose at it.

Raising your head, you glanced around briefly before your eyes landed on a massive burning building in the distance. Flames danced in the distance and smoke swirled in the sky.

You recognised it as your house and began screaming and thrashing in Gabriel’s arms.

He tried to sooth you, but even he knew how vain that was. He swallowed his tears and became determined to hunt Crowley’s remaining gang until his dying days. He knew what he had to do.

If that meant abandoning you on the streets as he did it, then so be it. In the Winchester name, Gabriel had a vengeance and pledged to protect you from afar for the remainder of his days.

He kissed your cheek and tried to ignore the tears rapidly falling down your cheek. “It’s alright, sh, sh. Let it all out, (Y/N). There we go.”

Bawling into his shoulder you continued to struggle until your exhausted limbs refused to move and then you were forced into a restless slumber.

Gabe continued to walk until he came across Harvelle’s Roadhouse, knowing exactly who ran it and what help they’d willingly give.

He knocked the door and wordlessly answered Ellen’s question by handing the last remaining Winchester into her arms.

With one last kiss to your forehead, he turned and left.

Ellen took you inside and settled you onto a bed.

What neither of them noticed however, were the two men watching vigilantly from a distance and how one held a letter with a symbol engraved into it, one that would represent so much more in the future.

________________________________

Finishing with your numbers for now, you glanced up and around the bar to see Ellen and Jo gone. Bobby nowhere to be found either. You shrugged it off and went to get yourself a drink from behind the bar.

Scanning the bar for it, you decided which one you wanted and was about to pour it but the bell chimed, signalling a new customer.

Instantly, you went to approach the new customer and ask what they wanted, but felt physically ill when you saw it wasn’t just one. There were two…

Your brothers.

Sam and Dean.

You stumbled back into the bar and gripped it tightly.

They smirked at you.

“Hello, sister.”

______________________________________________________________

Taglist ~

@kickingitwithkirk

@nerdettezebracorn333

#sam winchester x reader #sam x reader #Sam Winchester #dean winchester #dean winchester x reader #dean x reader #mobster!sam winchester #mobster!dean winchester #supernatural x reader #supernatural

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talesmaniac89 · 2 years ago

Text

Charity Heist 7 - aka. The Scaredy Cat Stratagem

A Supernatural Heist AU - Masterlist

Pairing: Hitter!Dean x Thief!Reader

Warnings: Idiots in love, smutty thoughts, a lot of swearing and a ton of bad jokes.

Watch the trailer here

A/N: This story is 50% jokes and 50% dirty thoughts. No deep angst, just fun and action! Inspired by the series Leverage.

Y/N = Your Name

Start Here - Last - Next

Where were you? Who were you? What the fuck were you?

Your brain was still so far in the fog it was a miracle that you managed to make it downstairs without a damn lighthouse leading the way. Though somehow Sam’s voice in your ear, relaying orders for your every step on the way, kept you focused. While Dean’s eyes burning into your back had spurred you forwards as your fight or flight instinct kicked in. Getting you down the stairs quickly, yet safely. As if you were fleeing from the dangerously attractive weapon’s specialist who was just two steps behind you the whole way down.

Wait… Scratch that ‘as if’. You were totally fleeing. And you were woman enough to admit it.

One second, you’d been opening the door in the office which housed the closet-that-shall-not-be named. If closets that weren’t IKEA made even had names. And the next you’d been downstairs, rubbing elbows with the rich and the wicked. Wanting to bathe in sanitizer to get the stench of their particular brand of evil off of you.

Successfully running away from your problems once more. Though you had no memory of your latest escape.

Luckily your training had been literally beaten into you since childhood. The joys of going with the mafia as your not-exactly-chosen educational institution instead of, y’know, school. But, it had come in handy for once. As Alicia, was still the star of your one-man show, at least externally. If not, your whole cover would’ve been blown. Just like your damned mind had been.

Why the fuck had you done that?

At some point, somewhere between the seam in the wall where the safe was and the flimsy safety of the closet, you’d lost your mind. First half of it – and then the other half had set out on a fucking movie trilogy journey to find the first.

Probably one involving a ring, some tiny hobbits and a wise old wizard. The big, cinematic ending seeing your sense of danger and survival instinct getting thrown into the fucking magma instead of the fucking ring.

Reckless. Brainless. Stupid…

As Bobby would say; you were an idjit.

Making your way across the crowded floor, you bit the inside of your cheek to not flinch as Dean’s warm palm once more found your bare back. The trained mercenary falling right back into his role just as quickly as you did. Slowly escorting you across the floor, as if you were leaving the party elegantly. Instead of fleeing it like the bat out of hell you were. You were, after all, professionals. Even if you didn’t exactly feel like one.

That had been dangerous.

Not to mention the fact that the mafia had been right on the other side of the damn closet door.

Ok, so maybe your priorities were slightly skewed. You were pretty sure that the amount of firearms the mobsters were carrying would’ve killed you faster than Dean’s lips on yours. But, hell, the biggest danger in your mind still seemed to be your lethally sexy cover date for the evening. Not the big honcho mobster, nor his questionable design choices and gunpowder style of accessories.

---

Taking a shaky breath, you let the cool evening air shock you back into reality as soon as you made your way safely out of the den of thieves masquerading as a charity event. Allowing the fresh air, free of perfume, cigarette smoke and alcohol fumes, to sharpen your mind.

Letting some of ‘Alicia’ fall to the wayside along with your plastered on plastic smile, you still had to keep your cover intact for a few more minutes. But, luckily, a little pout fit the arm candy character just as well when leaving a party. Alicia was, after all, a party girl hanging off of the arm of a man that daddy dearest totally wouldn’t approve of.

Shaking away the panic and reflection on the kiss that almost was. You instead refocused on the conversations that were actively playing out in your ear as you let Dean lead you out into the large driveway, over towards the waiting valet. Hell, you even managed to throw him a small, genuine smile as he shrugged off his suit jacket and placed it gently onto your shivering shoulders. Not one of Alicia’s smiles that had made your jaw ache and your cheeks hurt the whole evening.

“...That was way too close Sam! Who’s Bobby’s inside man? I’ll… I’ll ruin his damn credit score,”

Charlie’s panicked voice and not-so-scary threats were enough to fully ground you and turn your small half smile into a full blown one as you relaxed the shoulders you hadn’t realized you’d been tensing. Next to you, the small chuckle disguised as a cough leaving Dean showed that your hacker’s frantic threat had removed some of the tension from his too. The flat palm against your bare back becoming softer, with calloused fingertips playing against your skin, as he led you the rest of the way over to the valet who already had your car at the ready.

She was a sight for sore eyes. Though you did miss your bike, or even Dean’s Impala, it was always best to use less personal props for your heists. And hell, as you stepped towards the gleaming black Lexus waiting for you, you had to appreciate that she was a beaut. One already warmed up for your getaway, which made her even more beautiful in your eyes.

Stepping towards the passenger side of the two seater, you allowed Alicia to slip back in place to throw the valet a small, flirty smile. Biting your lip to keep from laughing as the flustered kid rushed to open your door for you and let you sink into the luxurious seats of the car you’d borrowed for the heist.

Well… Permanently borrowed, would most likely be more correct. But hey, at least the former owner was a crook. So you wouldn’t be losing any sleep over it.

“Considering he’s an insider in one of the biggest, baddest mafia groups around, I don’t think he worries about his credit score Char,” You quipped back a few seconds too late. Jumping back into the conversation again for the first time since you left the boss’ office as soon as you slid into the shotgun seat of the luxury car. Watching out of the corner of your eye as Dean slid into the driver seat.

Keeping your eyes focused forward, you listened to the back and forth of the rest of your team to avoid the gaze Dean threw your way. The tension from earlier had returned with a vengeance now that it was just the two of you in the car.

The older Winchester kept his eyes on you for a second, before just as quickly throwing the car into drive and getting you the hell out of dodge. Hot on the heels of the rest of your Scooby Gang who had made sure to trickle out shortly before you. With Charlie’s panic, and Sam’s calm matter-of-factness in your ear, you could almost forget you were alone with Dean in the car.

Almost.

Luckily, or unluckily, depending on how you asked. Crowley decided to speak up to further ruin your mood and tear at your frazzled nerves. The cocky voice of your temporary team mate grinding on your already frayed sanity as he decided to take the downtime afforded by the getaway to further annoy you. As was, apparently, his true calling in life.

“You’re lucky you had me there darling. If I hadn’t managed to get the boss back down to talk to Castiel, you might have lost that pretty little head of yours,” He drawled across the earpiece. Sounding like he expected some sort of participation medal for being able to rub elbows with the worst people you had the displeasure of ever meeting.

“First of all Crowley, don’t talk to me. Someone might think I actually tolerate you,” You gritted out. The last thing you needed, with your mind still halfway in the fog and your whole body on edge with nerves and adrenaline, was Crowley’s special brand of sass. His voice was 50% more grating than usual to your strained mind.

For a second you considered tearing out the earpiece and chucking it out the window of the speeding Lexus. Though the thought of Charlie’s heartbreak at losing one of her little toys stopped you from following through with the idea. Instead you settled on continuing your little attack on the devil you’d been forced to work with. To at least to get rid of some of the built up frustration from the close call and the closed closet.

“Second of all, I know you might look down on me since I don’t have a doctorate in tea and crumpets from Hogwarts like you fucking do. But if I was taught one thing it was to think before I act. So if I break your nose as soon as I see you… Know that I have thought things through, thoroughly, and am more than confident in my decision,”

“Ouch, that hurts pet. You wound me,” The infuriating Scotsman chuckled. Sounding anything but hurt as you rolled your eyes at the window in lieu of the mobster himself.

“Like you even have a heart to wound,” You spat back, just as Dean finally spoke up for the first time since his muttered curse at Sam back in the office.

“Shut up Crowley,” Dean’s voice was still rough and slightly breathless, but the hidden ‘or else’ behind the words, still managed to shut the big bad up for a little while. Which was honestly an impressive feat. Since Crowley never stopped talking.

“What’s your ETA Dean?” Sam shot in, in a weak attempt at stopping Dean from promising actual bodily harm on someone who was technically on the payroll. At least until the heist was completed. Since you needed a guarantee he’d keep his mouth shut instead of turning turncoat the moment you paid up.

“We’re one minute out. Do you think anyone noticed anything was off?” Dean’s voice was much more controlled when he answered his brother. Smoothly navigating the fast moving luxury car through the busy streets as he let his business-first mask fall fully back into place. Significantly decreasing the wordless pressure that had been resting like a heavy fucking blanket over the both of you since… Upstairs.

“No, as Crowley said. We drew their attention. And no one noticed you coming back down. Cameras were doctored. So we should be in the clear,” Sam said, sounding confident in his cleanup job. Which meant you were just as, if not more, confident in your clean escape.

The kid was a genius.

Didn’t mean you’d forgotten him calling you a kid though. You still predicted sippy cups and bibs in his near future.

“Did you find the safe (Y/N)?” Sam continued. Dragging you back out of the early planning stage of how you were going to procure enough sippy cups without him noticing.

“We’re good to go. Will brief you… Later,” You shot back. Hesitant to share anything that could be considered details when you had a possible enemy on the line with you. You trusted Crowley less than you trusted Chocolate Chip cookies to not be raisins in disguise. And you had no trust in those crumbly little bastards.

“So… Where to next?” Crowley shot back in when the line went silent as the rest caught on to the big mobster shaped elephant in the room. Choosing instead to watch as your car drove up to the designated meeting spot just as the big bad finished his question. Sounding like a clingy prom date that wanted to join an after party he clearly wasn’t invited to.

“Us? Back to the bunker. You? I honestly couldn’t care less… Hopefully hell,” You grumbled as the car came to a stop and you reached for the door handle with one hand. Your other hand going up to turn off the earpiece to not deal with the annoying echo of hearing everything twice now that you were all face to face. However, before you could reach for either one, Crowley spoke up again. His cocky grin clearly visible through the car’s window.

“Though I’ve heard it’s lovely this time of year, I think you still need me love,” Though you cut off your earpiece halfway through his sentence, you were still forced to hear every infuriating word as you slid out of the car and shot the man a glare when he let his eyes travel the length of your bare legs.

“Only thing I need is for you to stop breathing…” You huffed as you tugged on the hem of your knee-length dress that still seemed too short around the constant Union Jack Flirt. Before taking two steps forward to stop Dean’s quick move around the car towards Crowley and you. The last thing you needed on a night as fucked up as this one, was for Dean’s ‘protect the family’ instinct to rear its ugly head again when you were still reeling from the almost kiss.

Forget destroying you; it would pulverize you.

“Like, right the fuck, now,” You added, for good measure, when the mobster only seemed amused by your annoyed words. His smile not falling even as you feinted a reach down for one of the throwing knives strapped to your thigh.

Bobby would be furious if you killed a useful tool, which was what Crowley was; a tool. But… Maybe if you just wounded him? Just a little?

“Whoa, whoa… Remember. I’m one of the good guys tonight,” The villain cosplaying as a superhero in front of you said. His hands up in a gesture of mock surrender as he took a step back. Though you were 99% sure it was from whatever look Dean was giving him next to you, rather than your empty threat of making haggis shish kebab out of him.

“And when midnight comes around you’ll lose that glass slipper you call a heart and go right back to being bad again,” Dean jumped in, sounding more exasperated than angry as he reached for your hand and gently pulled it away from where you were seriously considering taking out one of your knives.

Just one little knife wouldn’t hurt Crowley all that much… No, that was a lie. You were an excellent marksman when it came to your throwing knives. It would hurt him, a lot, if you wanted it to. And you really, really did.

“Crowley… We’ll call you. The rest of you. Get the cars into the garage around the corner, we’ll drive back together in the van and get ready to debrief with Bobby,” Sam sighed, taking charge of the chaotic conversation like he always did. Which was probably why he was the one to be the lead on the field. The man not only had a stupid amount of law degrees, but he was also an expert at herding cats. At least when your rag tag group were the misbehaving felines he had to wrangle.

Giving the big guy an overexaggerated pout you dropped the handle of the throwing knife you’d been holding onto. And, at the same time, not-so-subtly, moved your hand away from Dean’s where it was searing hot against your skin. Keeping your eyes on Sam, you missed Dean’s hurt look, though you still felt his gaze on you. But you couldn’t risk looking into those forest green labyrinths that could easily make any girl get lost in them. You needed your mind to be clear.

Bobby was a man who demanded details, and you couldn’t risk a certain Mr. Winchester short circuiting your brain before you’d shared everything you’d learned during your time in Mobster Land™ - The unhappiest place on earth.

As with any father figure, Bobby’s disappointment was the scariest thing you knew. And you’d once hid out in an abandoned, supposedly haunted, amusement park for three full weeks with assassins hot on your heels.

“Yes sir, Mr. Boss Man, sir,” You groaned as you shuffled towards the van, or as close to a shuffle as you could get in six inch heels, and right into Charlie’s waiting arms. Stopping to let the redhead fuzz over every part of you and act like a worried soccer mom checking for scraped knees and bruises whilst talking a mile a minute. Leaving Dean, and the forest fire burning in his eyes behind as you wrapped yourself in your best friend’s frantic worry and focused on calming her fears.

Was it cowardly to use your best friend as a shield to hide from your crush? Hell yes. Did you care? Oh, hell no. You’d do it again in a heartbeat.

----

The drive back to the cold war bunker you called your home and headquarters was luckily not as awkward as you’d feared.

Mainly because Dean always demanded to drive when all of you were in the car. And Sam had an iron hold on the shotgun seat. Which meant Char, Cas and you were all piled into the back. Lounging in the miniature version of Charlie and Sam’s office that the back of the van had been remodeled into shortly after you… Procured it on another job.

The military grade surveilance van was your home away from home. One you had affectionately nicknamed The Mystery Machine. Though it was a little less 1960's era hippie, and a lot more sleek, black and un-noticeable than its namesake. A kitted-out, mobile HQ on wheels. For easy, on-the-go security breaches and data gathering.

Need a new identity? We deliver! Fresh and untraceable to your door in 30 minutes, or it’s FREE! Well… Not really. Iron-clad identities were expensive.

And though you preferred your Kawasaki Ninja whenever you got to use her, bikes really did make for faster getaways after all, you didn’t mind the Scooby van. At least it was big enough to house your full little family. So it was infinitely better than the two seater Lexus, where it had only been Dean and you.

After all, it was thanks to the van that you somehow made it back to your impenetrable batcave safely; without another burning look from Dean. And, as soon as the car came to a full stop in the underground garage, you nearly fell out of the van doors in a mad attempt to keep that streak going. With a poorly thought out plan to run away from one of the best trackers and killers the world knew - in six inch heels.

Still, your experience of running in heels had been put to good use, for the most part. You’d left the rest of your team standing; confused in the dust of your cowardice and shredded pride. But Dean had of course hurried after you. Probably wanting to throw out some weak excuse about adrenaline to not ruin the team’s chemistry. And you really didn’t want to hear it.

He’d nearly caught up to you just as you reached your room in the bunker. Leaving you just enough time to make a mumbled excuse about changing out of your undercover gear and into something less… ‘Torture but make it fashion’-esque. Before awkwardly shutting the door in Dean’s face just as he parted those full lips that you’d been so damned close to kissing.

You knew you couldn’t read too much into the adrenaline fuelled moment you’d shared in the closet. Fear did strange things to those of you who lived on the edge of the law. It was like a drug. One you both craved and needed to avoid.

So, you’d done the big girl thing; you’d put your whole damn weight on the door like Dean was suddenly a B-grade horror movie villain ready to burst into your room any second. But, instead of demanding to continue the conversation, Dean had just stood quietly outside your door for a few minutes. Before you heard the unmistakable sound of his Oxfords walking down the hallway, back to his own room.

And, like the totally rational adult you were… You’d been left unsure if you were happy he’d given up, or heartbroken that he hadn’t tried harder.

---

Though you wanted to let cooler heads prevail and hide out in your bedroom, like the goddamn coward you were, you couldn’t. You still hadn’t clocked out for the night and Bobby would have your head if you didn’t show up to the debriefing. So, you quickly found yourself back around the table with the rest of your ragtag Robin Hood crew. Sulking into a beer bottle you couldn’t even make yourself touch.

Past tearing the label into shreds that was...

Dressed in your favorite t-shirt and lounge shorts combo you did feel a little more at ease, but you could still feel Dean’s eyes on you. Which made you shift uncomfortably in your seat as your eyes focused on literally anything but the criminally hot weapon’s specialist.

He’d changed too. The suit was replaced with a pair of gray sweatpants hanging low on his hips and another one of his unlimited supply of slightly fitted band t-shirts that was riding up just enough to show a flash of his toned stomach every time he reached for his beer.

Which made it doubly hard to focus on the party debrief going on around the table as the group filled Bobby in over the speaker. First, because of the burning look that silently demanded for you to actually speak to him. And second, because gray sweatpants should be fucking outlawed. Because damn it.

It was a goddamn Catch 22.

You couldn’t look up without meeting those burning green eyes, and you couldn’t look down without being caught in a ‘my eyes are up here ma’am’-situation. And after feeling Dean’s obvious arousal as you rolled your hips against him in the closet, you knew the man would make those sweatpants work for him. The feeling of him against you had been… Mouthwatering, for the lack of a better word.

Aaaaand, there you went again. Back into the fucking closet. Damn it.

Keeping your eyes squarely on the speaker playing the part of Bobby, you tried to follow along as Cas shared the juicy pieces of information he’d managed to fool one of the higher ups in the whole charity scam to share with him. As always, Castiel had created miracles with that silver tongue of his. Easily cracking even the hardest nut.

“So he basically told you everything huh? Including the whole account scam? How did you even manage to do that?” Charlie seemed starstruck as she looked at the grifter wide-eyed. Listening, enraptured, as the usually quiet, stoic man basically gave you everything you needed to move on with your plans, except for the account numbers. That was Charlie and Sam’s job.

“It’s easy,” Castiel shrugged. Though, of course it was, for the still quite mysterious man, who could get anyone to confess to sins as easily as you could scale a wall. Which was also damned easy. For you. So you couldn’t help but lift a doubting eyebrow as you waited for Castiel’s explanation of how easy it really was.

“Just a sympathetic nod in the right places, words that hint to me knowing more than I should… And of course reading the signs. He had a slight scruff and the designer suit he wore was a little crumpled. Clearly he’d been working double time. And, by the way his eyes followed the main boss around the room, he seemed displeased that he wasn’t receiving the praise he should be getting,” Castiel added when his initial statement was only met with raised eyebrows and wry chuckles from the rest of your group of master con-men.

“Yeah… Easy, right,” Charlie nodded. Her voice had a slightly higher pitch as she returned her attention to the papers in front of her. Suddenly seeming very interested in the blueprints as she mumbled something inaudible under her breath. Though it didn’t take a rocket scientist to guess what she was grumbling about; considering her own problems with the art of small talk.

“Next, you said we have the safe location locked down (Y/N)?” The smile on your lips quickly fell away as Sam turned to you. Kicking off your breakdown of your role in the job with the top item on your list, and the most important task you’d had during the party. The safe.

That fucking safe was the reason for all your problems.

“Yes, it’s where I thought it would be. The back wall of the big boss’ upstairs office. Easy to miss too, a seam at the bottom of the wall is the only indication it’s even there,” The professional thief in you easily took over as you jumped into an in-depth explanation of the office’s layout. Since you had missed your chance to put up any hidden cameras once Sam warned you about the mobsters moving up the stairs.

“But… Unfortunately, since we had to make a quick escape, I couldn’t get actual eyes on make and model,” You sighed, feeling like a failure after Castiel had gone above and beyond. Technically, you’d completed your job for the night, but you still felt like you’d worked on a group project with the smartest kids in class and the only thing you had to show for it was a shitty cover page - drawn in crayon and totally coloured outside the lines.

“Not your fault kid, it’s all on me. Our insider’s on his way to a shiny new prison cell as we speak. You don’t backstab me or my family…” Bobby’s slightly rough around the edges form of comfort still made you feel a little less shitty on the gap in your own information. Even if it didn’t make up for the fact that you should at least have gotten actual eyes on the safe.

“Will not knowing the make and model be a problem for you on go-day?” He continued as you smiled at the speaker, knowing full well the big boss couldn’t see you… Probably.

“No way. I’ve yet to meet a safe I can’t crack. Just means my time estimate for the actual job will be wider. Could be a minute, could be thirty,” You said with a small shrug. And it was true. You’d gotten into harder places than a mobster boss’ safe.

Plus, considering his decor choices, you were sure his safe would be childsplay. His prohibition era design decisions meant that there was at least a little bit less of a chance that it was a bio-locked safe. Though you’d prepare for the worst either way. Just because he decorated like a stereotypical goon didn’t mean he wouldn’t have the smarts to protect his assets. After all, he was at the top of a very large organization. Which wasn’t something you got with just beauty, and no brains.

“That’s our girl,” Bobby shot back, making your sunken shoulders straighten a little again as you grinned shyly at the speaker. Praise from Bobby was hard to come by, so it only took a few words from the big guy to make you feel on top of the world again.

Reinvigorated, you pulled the tablet on the table to you and continued your debriefing as you marked the escape and entrance routes you’d found in the house on the digital map shared with Bobby in whatever strange location he was holed up in. While the others filled in any additional details for you to add onto the map.

Your plan was coming together.

You knew their weaknesses. You had their identities and information. And you knew, with 100% certainty, that you would be able to break into that damned safe. Now you only needed Sam and Charlie, your super hacking team, to get those account codes, build the plan and layout and find the backdoors into their servers.

And, as Bobby jumped in with the info he had gathered for the turnabout angle on his own little solo mission, you knew you’d be ready to take them on from both sides at one time.

These bastards were going down. But first…

Dean’s eyes were once more laser focused on you, now that the next steps were nailed down. You could nearly feel the shift as the mercenary was once more replaced with the man who still seemed hell bent on breaking your fragile little thieving heart with a conversation you really didn’t want to have. So, first you needed to do what you did best...

You needed to run the fuck away. And hide in your room like the coward you were.

Start Here - Last - Next

Charity Heist: @foxyjwls007 @seppys-return-to-madness @stoneyggirl2 @ladysparkles78 @twinkleinadiamondsky @tmb510 @mimaria420

Dean Winchester Tags: @ria132love @woodworthti666 @defenderrosetyler @akshi8278 @justanotherwinchester @lyarr24 @torn-and-frayed @all-will-be-well-love @wearesuchstuff1 @thefridgeismybestie @adoptdontshoppets @screechingartisancashbailiff @septixtrash @punof-agun @deandreamernp @justagirlinafandomworld @sexyvixen7 @justrealizedimmascifygurl @globetrotter28 @iprobablyshipit91 @mrsjenniferwinchester @leigh70 @djs8891 @pink-sparkly-witch @deans-spinster-witch

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