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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

#timezone reblog #dean x female!reader #dean winchester fanfiction #au dean winchester #heist au #thief!reader #hitter!dean x thief!reader #hitter!dean

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talesmaniac89 · 1 year

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Forever Tags: @deanwanddamons @winchest09 @hobby27 @awesome-badass-cafeteria-sauce @sea040561 @donnaintx @thatmotleygirl @chocolateheart @superfanficnatural @flamencodiva @starryeyeseunbyul @waywardbeanie @supernaturalenchanted @ellewritesfix05 @emoryhemsworth @alwayskeepfightingsweetheart @the-lost-wanderer-of-the-night @strangersstranger @tatted-trina6 @jensengirl83 @whatareyousearchingfordean @atc74 @jackandthesoulmates @gh0stgurl @samsgirl93 @i-opened-the-chamber-of-secrets @dainrumnaheim @440mxs-wife @roseblue373

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

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 | Y/E/C = Your Eye Colour

Start Here - Last - Next (Coming soon)

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

Suck it Catwoman.

Skylights, apparently, included.

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

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.

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

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.

“Stay safe (Y/N)...”

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.

A straight forward leap of faith would do just fine.

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

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.

---

It just wasn’t worth it.

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.

At least they beat him.

Though, you should have known better.

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

You were a goddamn professional.

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

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

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

Your only choice was the rear entrance.

“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.

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.

Fucking typical.

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.

Fuck.

The cavalry was here.

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.

“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.

“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,”

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.

“Get inside, now,”

---

You were home free.

Damn him and his… Everything.

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.

Which, actually…

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.

“... Why?”

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

#reblogging for tags #dean winchester heist au #hitter!dean x thief!reader #hitter!dean #spn heist au #supernatural heist au

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talesmaniac89 · 1 year

Text

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

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 | Y/E/C = Your Eye Colour

Start Here - Last - Next (Coming soon)

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

Suck it Catwoman.

Skylights, apparently, included.

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

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.

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

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.

“Stay safe (Y/N)...”

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.

A straight forward leap of faith would do just fine.

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

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.

---

It just wasn’t worth it.

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.

At least they beat him.

Though, you should have known better.

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

You were a goddamn professional.

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

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

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

Your only choice was the rear entrance.

“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.

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.

Fucking typical.

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.

Fuck.

The cavalry was here.

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.

“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.

“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,”

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.

“Get inside, now,”

---

You were home free.

Damn him and his… Everything.

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.

Which, actually…

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.

“... Why?”

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 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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talesmaniac89 · 1 year

Text

Limelight 17 - 15 Minutes of Fame

Limelight Masterlist

A Dean x Reader Social Media AU

Pairing: CEO!Dean x Journalist!Reader

Summary: The workaholic and media shy CEO of Winchester Inc, Dean Winchester, is forced to try online dating by his friends. What will happen when he swipes right on (Y/N), who is working on a series on online dating for her magazine?

Warnings: Red dating flags, Exes, frustration and misunderstandings

Y/N = Your Name

Start Here - Last - Next (Coming soon)

Limelight Tags: @twinkleinadiamondsky @jamerlynn @samsgirl93 @linki-locks11 @ultimatecin73 @joeyfilth @mimaria420 @lacilou @itzabbyxx

Forever tags will be added as reblog

#timezone reblog #ceo dean winchester #spn social media au #supernatural social media au

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talesmaniac89 · 1 year

Text

Limelight 17 - 15 Minutes of Fame

Limelight Masterlist

A Dean x Reader Social Media AU

Pairing: CEO!Dean x Journalist!Reader

Warnings: Red dating flags, Exes, frustration and misunderstandings

Y/N = Your Name

Start Here - Last - Next (Coming soon)

Limelight Tags: @twinkleinadiamondsky @jamerlynn @samsgirl93 @linki-locks11 @ultimatecin73 @joeyfilth @mimaria420 @lacilou @itzabbyxx

Forever tags will be added as reblog

#reblog for tags #ceo!dean winchester #dean winchester social media au #ceo!dean x journalist!reader #spn social media au #ceo dean winchester #dean social media au #supernatural social media au #ceo!dean #dean x yn #dean x reader

77 notes · View notes

talesmaniac89 · 1 year

Text

Limelight 17 - 15 Minutes of Fame

Limelight Masterlist

A Dean x Reader Social Media AU

Pairing: CEO!Dean x Journalist!Reader

Warnings: Red dating flags, Exes, frustration and misunderstandings

Y/N = Your Name

Start Here - Last - Next

Limelight Tags: @twinkleinadiamondsky @jamerlynn @samsgirl93 @linki-locks11 @ultimatecin73 @joeyfilth @mimaria420 @lacilou @itzabbyxx

Forever tags will be added as reblog

77 notes · View notes

talesmaniac89 · 1 year

Note

Hey darling, love your blog! Thanks for making such amazing stories 😊

What apps do you use for the social media posts? They are so good

Hi! Awh thank you! I'm happy you're enjoying my stories 💕

I don't use an app for my Social AUs, I make all the images from scratch in canva. Basically I've created a series of social media, email, messenger, and other templates based on how the different social media pages look on my phone and then just copy them and insert what I want like the below. Because the apps I looked at couldn't do what I wanted them to. It's definitely the harder way to do it, but I want to make it just right (and use gifs hahah). So it just made more sense to make each image from scratch in a design tool instead. Canva.com is free to use as well! Though I'm using the paid version to have the rights to use their stock imagery, which is what I am using in my stories.

#answering asks

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talesmaniac89 · 1 year

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Charity Heist 11 - aka. The Reluctant Rescue Team

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 (Coming soon)

A/N: Sorry for the delay here! Had a bit of a weekend 🤣

For a few seconds, the room was completely quiet except the soft sound of traffic coming through the speaker in the middle of the table showing that Bobby was out and about. None of you dared speak as you took in the news.

Crowley, the damned idiot, got caught because he had to visit if his fucking tailor? He couldn’t even go one job without ordering another stupid black suit?

Fucking perfect.

Yet, just as soon as the silence had settled over the War Table, all hell broke loose, with every member of your rag tag group of master criminals speaking over each other. Sounding less than the well-oiled con machine you were and more like a room full of school children.

“He’s an idiot, that’s why I always say we shouldn’t work with him…” Dean growled from next to you, just as Charlie made some very apt comparisons between the mobster and a chimpanzee. Though you barely even caught either’s words over your own tired groan.

“Holy… God, how the hell did he get caught?” You shot towards Sam, though you knew the youngest Winchester wouldn’t have held back on the details if he knew anything else.

“You know Crowley. If nothing else, the man believes he’s untouchable. The king of the underground. So of course he had none of his own men with him,” Sam just sighed with a tired shrug of his shoulders. Leaning forward, your intelligence guy seemed just as lost as you as his big hands splayed against the wood of the table to steady himself as all his perfectly laid plans were shaken off kilter by Crowley’s antics.

“So… What now?” Castiel spoke up, keeping much more calm than the rest of your group. As always, your grifter was the most composed one among you as he leaned back in his seat. The last remnants of his latest role still shining through in the cocky hold of his shoulders and the slightly bored look in his eyes. Damn it, you hated it when he stayed in character. But the job was still on, and nothing could shake him from his role.

“Now… We have to change our plans,” Sam gritted the words out through clenched teeth. If there was one thing your intelligence guy hated, it was anyone messing with his carefully laid plans. After all, he didn’t have a folder for ‘what to do if your idiot collaborator decided he feels like being kidnapped’.

“We have to save him… Don’t we?” Charlie said with a sigh as she let her head drop to the desk with a dull thud.

Pouting at your best friend you let out another annoyed groan.

You knew she was right. But that didn’t mean you had to like it. After all, the problem with being an actual super thief with a heart of gold was that you actually had a heart. So you felt bad when you did bad, even if it was still kind of part of the job description. Maybe less so now than before, but you were still technically breaking the law. The devil and angel on your respective shoulders were mortal enemies, yet somehow also friends with benefits. Which wasn’t really great for your moral compass. As Charlie had said earlier that day; your rag tag group all had questionable morals.

And though Crowley was an absolute ass, you knew you’d feel bad if he ended up with a brand new shiny pair of cement shoes at the bottom of a bay somewhere just because he was helping you out with a job. Even if he’d made sure to squeeze as much money as he possibly could out of you. You all would, unfortunately.

“Do we have to?” Dean’s groaned, tired voice echoed your thoughts perfectly as he finally spoke up again. Though you knew your hitter wouldn’t leave anyone he was working with hanging out to dry. Even if the person in question kind of deserved it.

“I guess we have to…?” You sighed, the statement coming out more like a question as you looked up at Sam. After all, him and Bobby made all your plans. At the end of the day, it was all up to them. You wouldn’t move without his green light. Even if you would drag your feet moving when he finally gave the signal.

“Yeah, we need a revised plan, one including getting Crowley out of his own mess,” Sam confirmed, though he didn’t look all that happy with his own words either, sinking back into his seat from where he’d stood up to deliver the bad news.

“He annoys me though…” Charlie shot in as you all went silent, looking at the speaker as you waited for Bobby to talk some sense into you.

“He annoys all of us kid, but we have to save him. If nothing else because he’s a liability,” Bobby’s voice finally spoke up through the speaker with a humorless laugh.

“Ok. So what’s the new plan then?” You shot in, before another chorus of groans could shave even more time off of your planning. Hell, even though you were annoyed, maybe this was for the best? You had energy to burn through, and as the team’s retrieval expert, it would most likely be up to you to… Retrieve, the mobster.

Plus, a job would mean you wouldn’t have time to think about the gun range. Or Dean. Or what the hell all of that was. Which the little escape artist you called a heart really appreciated.

“We need to hit them from multiple angles,” Bobby said through the speaker after taking a beat to think things through. Your mastermind was coming through for you once more. You could almost hear the gears grinding as he threw together a new rescue plan on the spot. Or, hell… That was probably still just background traffic, or Bobby changing the gears of his beat up truck, but it sure as hell sounded like gears grinding.

“Crowley might be a bastard, but he’ll be true to his word. At least as long as the bad guys don’t offer him more money than we already have. Which, knowing their type, I doubt they will. They’re a miserly bunch of bastards,” Bobby continued as you all just nodded at the speaker. Still acting like the little piece of plastic and wiring could see you.

“But, we can’t let them catch us. And we can’t let rescuing our damsel interfere with our plans,” He mused, as he worked out the kinks in his new plan out loud. Leaving you all to hold your breath, muscles tense as you waited for him to pull the trigger; firing you all into action.

“Castiel, you need to hit them on their home turf. I want you to use your new persona to pay them a little visit at their white washed headquarters. Keep the bigger guys busy while we save our man,” Bobby finally said, earning a little nod from Castiel, who was quickly falling fully back into character.

“They won’t be expecting me though… Might pose a problem,” Castiel’s voice was flat and void of emotion as he drawled the words. Making you shiver as you realized it wasn’t Cas speaking anymore. He was once more fully in character.

“True.. Charlie, you go with him. Sneak into the IT department and set up some meetings in their calendars with Castiel’s cover. While you’re there, take this opportunity to plant some surprises in their system. A nice little bonus for messin’ with our plans,” Bobby easily corrected his own plans without breaking a sweat as you all sat waiting for your own orders.

Watching your red headed hacker across the table, you cocked an eyebrow as Charlie’s cheshire cat grin replaced her former annoyance. Your best friend was nearly bouncing in her seat as Bobby gave her her role in the new plan. A wicked look in her eyes that… Honestly? Kind of scared you. She clearly had something up her sleeve, since she was normally not that happy to do field work.

“Finally! I made this little virus a looong time ago. I can hide it in their servers and set it off with a click of a button whenever we want. It’ll cripple them, send their client’s data to a competitor of our choice and wipe their whole server clean. Their expensive computers and servers will just be overpriced paperweights when I’m through with them,” The red head was close to laughing maniacally as she let you all in on whatever it was she found so funny.

“Good, sounds like just the thing we need kid,” Bobby didn’t even try to hide the pride in his voice as he responded to Charlie’s delight. A small chuckle escaping your normally tough-as-nails boss, before he cleared throat and fell silent, trying to formulate the actual rescue mission.

“Alright… So while Cas and Charlie keep the higher-ups busy, we’ll need to get Crowley out as soon as possible. Dean, (Y/N) and Sam, I want the three of you to hit the spot where they’re keeping ‘im,” He finally continued after a brief pause, where you swore you could actually see him entering his own little mind palace through the small speaker.

“Sammy… They might have some mid-level guys there. Crowley’s a pretty big mark for them after all. So they might have brought in someone a bit higher up than just your common muscle to keep an eye on him. Though if we’re lucky they haven’t gotten there yet. I want you to play the role of mid-level boss yourself or distract them if the bosses are already there. I trust you to figure out how,”

“Quietly?” Sam shot in as he rolled his shoulders, his jaw set and clearly ready for a fight. Nothing pissed off the younger Winchester more than having someone mess up your jobs. Though you didn’t miss the way his hazel eyes softened from the trust his adoptive father placed in him.

“Quietly, if possible. But feel free to get rough if the situation calls for it,” Bobby said after only a moment of deliberation. You weren’t worried that your mastermind was sending the youngest Winchester after the area bosses, hell, you’d seen Sam fight. And though Dean normally took on the role as the loud and violent distraction in any of your jobs, you knew his younger brother could more than hold his own in a fight.

“So you want me to go get our damsel?” Dean sounded nearly nauseous as he asked the question. Seeming no more willing to go save the Scotsman than you were.

“No. Your job’s a lot more important than that Dean,” Bobby shot back, causing Dean to frown as he leaned closer towards the speaker, waiting for his orders.

“You need to keep our retrieval expert safe. (Y/N) will be the one infiltrating. If everything goes as planned, she should get in and out quietly with Crowley in tow while Sam poses as one of the bosses, or at least a mouthpiece for one to draw their attention. And you stand at the ready to help our girl out if something goes wrong,” Bobby shot back, leaving no room for arguing in his words. Though you could see Dean’s jaw tick in annoyance at the thought of you going in alone to save the greased up mobster.

“Alright, I’ll go play knight in shiny harnesses and save our damsel. Dean will have my back, outside. Right?” You shot in, wanting to cut Dean off before he still tried to argue with your mastermind’s orders. Which, by the look of his eyes burning into the speaker, he was moments away from doing.

Moving those same burning green orbs off of the speaker, Dean’s eyes settled on you as he tried to make you back down. But there was no way you would. You were the retrieval expert. Bobby’s plan made sense, even if Dean for some reason refused to see it.

This was a job. Whatever had happened in the gun range took the backseat when there was a job to do. So even though your body was still heated from the feel of your hitter devouring you only 30 minutes earlier, you were not backing down. You were a big girl, and retrieval was your thing.

“Right,” After a beat or two of silence, Dean sighed in defeat as he spat out the single word between gritted teeth. His eyes resting on you for just a second more before quickly standing up to get ready.

It was time to go save yourself a damsel.

---

The ride to the job in Sam’s beat up truck was awkward, for the lack of a better word.

Not only had Dean not-so-subtly been sending you burning looks through the rear-view mirror that made it very hard for you to focus on your rescue mission. But Sam and Dean kept arguing the finer details of the case. Mainly surrounding you and your role.

And by that you meant Dean kept arguing the details.

Your hitter kept suggesting changes to the plan, which coincidentally all involved him going in first to clear a path for you, which you swiftly ignored. You didn’t need a damn babysitter. Dean had seen you in action before. Hell, you’d nearly knocked him out the first time he came to recruit you. But, you had no choice but to keep your mouth shut, or risk getting dragged into a shouting match with the two most stubborn men you knew. After all, no matter what Dean said, Bobby had made your roles crystal clear.

You were the retrieval expert. You would be going in to save the idiotic Scotman with a suit fetish and a hard-on for his personal tailor. No matter how much your green eyes hitter batted his long lashes at you or pouted like a giant man baby in the shotgun seat.

“I wish we could just turn this damn car around and leave the bastard to rot,” Dean groaned from the front seat after another round of arguing about who should do what during the job.

“Well, we’re basically here, so a bit too late for that Dean,” Sam sighed, sounding like he wished for nothing more than to turn the beat up truck he refused to part with around too.

“We’re here? Good, let me go do my thing,” Cutting off the new round of arguing over the plan that you knew Dean was gearing up for, you spoke up for the first time since the car ride started. Both to at least get one shot in against Dean, but also because you were beyond ready to get your thieving on. Finally perking up at the idea of being out of the tense atmosphere in the car and Dean’s burning eyes, you nearly bounced in your seat from the thought of some much needed action to burn off all the dirty energy in your body.

“You seem weirdly eager to rescue Crowley (Y/N),” Sam said as he pulled up and parked just half a block from where the mobsters had locked up your ‘damsel’. The hazel eyes meeting yours in the rear-view mirror looked at you in concern, as if you were possessed or losing your mind just because you were happy to work.

Though, hell, if you had been possessed you would have ‘jesus take the wheel’-ed the shit out of that. With the way your life was going, you were just about ready to issue an open invitation to any demon who wanted to come take control of your life. Whichever demon was brave enough to come sort out your mess would have earned their permanent residence in the husk you called your body. You could be roomies.

Maybe Netflix would give you a movie deal; a whimsical sitcom about you and your demon roommate. You’d name it ‘Doom Mates’ and Charlie would hate it.

But, unfortunately, there was no demon willing to possess you and sort out your messy relationships. So, you were forced to do it yourself (or at least avoid the hell out of it) as you once more ignored Dean’s eyes in the rear-view mirror and wrenched open the truck door to jump out as soon as Sam had brought the car to a full stop.

“I’m not thrilled about the… Subject of the retrieval. But it’s been a minute and a half since I last got to stretch my infiltration muscles. Plus, Charlie made me a new harness, and I need to play with it,” You shot back at Sam as he followed you out of the truck. Swallowing the many other reasons as to why you nearly needed the gig. Like the forest fire burning in Dean’s eyes, or how you could still taste the ghost of spiced peppermint on the tip of your tongue.

Taking a shaky breath, you plastered your best imitation of a smile on your face and turned to squint down the street as Sam pointed out the building where Crowley was kept to the rest of you. The sight of the unlit neon sign outside of the business in question had your smile fall as you grimaced at the damned cliché.

They had Crowley locked up in an empty, closed down nightclub.

Because of course they did.

Would it kill the bad guys to be fucking original for once? Why was it always warehouses, empty buildings or abandoned lots? Why couldn’t you go save someone from a fun place for once in your life? Like DisneyLand, or an active water park… Or at least somewhere with an open bar. Because, fuck, you could use a drink.

Frowning at the building from half a block away, you busied yourself checking your equipment as the Winchester brothers continued their circular argument about the plan. Meanwhile, you were busy making plans of your own. From what you could see, the baddies had all congregated around the front of the building based on the few cars you could just about glimpse peeking out around the corner. Clearly not seeing Crowley as a big a threat as he thought he was. Which didn’t really damage your infiltration options much, as you’d usually never choose the front of the building as an entrance point anyway.

Hell, from your vantage point, you could clearly see multiple ways into the nightclub. Including an unguarded rear entrance just begging you to walk in and sneak Crowley out from right under their noses. Still, as Sam had pointed out more than one time in his argument with Dean on the car ride over, you should be prepared for the worst.

The unguarded rear entrance could be a trap. You had no way of knowing. So an infiltration plan was still needed.

“Do you think you can get in from the roof (Y/N)? Charlie got us the blueprints, and there seems to be a skylight up there. Might mean you’ll get eyes on Crowley as well before you make your way inside,” Sam seemed to finally get sick of shooting down all of Dean’s ideas as he directed his next question at you instead.

After all, Bobby wanted this to be done quietly. And Dean going in first to loudly, and most likely violently, clear a path for you wasn’t exactly quiet.

“You want me to throw myself in through a skylight and rappel into mobster territory? That’s a crazy idea… Insane! I mean, there’s a perfectly good door right there,” You stage whispered, acting it up for the non-existent cameras as you pointed towards the unguarded rear entrance to the abandoned club.

Ok… So maybe you were playing it up just that little bit extra to annoy your hitter. Who suddenly seemed to think you were incapable of performing even a simple retrieval mission. As if you’d lost all your hard earned skills after one makeout session.

Who the hell did he think he was? Some sort of fucking dementor? Sucking out your ability to scale a wall with just one kiss?

The man was a damned good kisser, sure, but just because you could be someone’s good girl and be willingly shaped up against their body one second that did not diminish your skills as the fucking awesome super thief you were. You were fully capable of being a goddamn professional, and drown in peppermint spiced kisses thank-you-very-much.

“So… You’ll do it?” Sam asked, the small tight smile of his lips tinged with mirth as he rolled his eyes at your drama queen act and the subsequent low growl that left his older brother in response. Though you knew he was just asking for the sake of a verbal confirmation, as you could see him gearing up to go distract the guys out front and buy you some time.

“Of course I fucking will. This is gonna be awesome,” You grinned as you dipped back into the back of Sam’s truck to stuff a few additional toys and gadgets, courtesy of your awesome best friend, into your backpack. Including the new harness you had to take for a test spin.

“(Y/N)...” Dean tried, though you could tell the fight had gone out of him as his tense shoulders fell and his hands busied themself with double checking his own little arsenal. Still, for a second you froze. Taking a few deep breaths before stepping out of where you’d been halfway inside Sam’s car to fully see the Winchester brothers again.

Saying nothing, you simply raised an eyebrow at your hitter as you hoisted your go-bag up on your shoulder. Lips drawn in a thin line as you waited for whatever argument he had planned to stop you from doing your favorite thing in the whole damn world; throwing yourself off of a roof and into a building, however absolutely batshit insane that sounded.

“You got this, just stay safe,” He finally sighed in defeat, giving you a soft smile which you returned with an enthusiastic grin.

“You know I will,” You shot back, throwing a quick wink at both boys before quickly and quietly making your way towards the back of the building. Only throwing a glance back to see Sam get back in the car, ready to drive up front, and Dean setting out after you, just slightly to the left. Moving towards the building from another angle to set up camp near the rear entrance.

It was go time.

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

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#reblog for tags #dean x reader #hitter!dean x thief!reader #thief!reader #hitter!dean #dean winchester heist au #spn heist au #supernatural heist au

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talesmaniac89 · 1 year

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Charity Heist 11 - aka. The Reluctant Rescue Team

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

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A/N: Sorry for the delay here! Had a bit of a weekend 🤣

Crowley, the damned idiot, got caught because he had to visit his fucking tailor? He couldn’t even go one job without ordering another stupid black suit?