In short, your little group was in the business of cons, heists and all things criminal. Though you were far removed from common criminals. No, your marks weren’t the average Joe down the road with too much money lining his pockets. You had your eyes set on bigger fish, or… 

Sharks. 

As a group made up of mainly former criminals and up-to-no-gooders, you all put your skills to good use. Taking on cases from normal folk and the more righteous side of rich who’d been scammed out of their hard-earned cash. Scamming the wannabe Don Corleone’s and other evil bastards who did it right back. Usually with the added benefit of emptying their bank accounts of all their ill-gotten gains. And, as Bobby kept speaking, this seemed to be just the kind of case that would end up adding zeros to your bank account.

You might be fighting the good fight, but that didn’t mean you had to do so for free. After all, what was the point of the swanky bunker life if you couldn’t live it in relative style and comfort?

“This is a good one, real money up for grabs. So, listen close...” He added once the room quieted down. 

As always, the retired military officer was the man with the plan and the guy who decided on your cases. And, as usual, he was locked away somewhere doing God knows what, communicating with you solely via phone. By now your image of Bobby Singer was more speaker than human, or possibly Charlie from Charlie’s Angels; though you weren’t exactly spies. Well…

Not all of you anyway.

Hell, you didn’t even know where he lived. There had  been mentions of your very own kingpin owning some impressive real estate tied to the US military's automotive research and development sector once. Though, if that was true, you wished he’d put some of those resources to good use making you a batmobile. 

You really wanted a batmobile. 

Still, batmobile or no, either way, Bobby was your mastermind. He handled your debriefs, found the connections, got you in the door and more often than not left the legwork to your less-than-family-friendly Scooby gang.

Not that you minded. You loved the action that came with being one of Singer’s little foot soldiers. You got to snatch up some shiny goodies, break into places others saw as impenetrable and, overall, just kick ass. All in the name of doing good. 

Though you’d probably never admit to it in fear of sounding sappy, deciding to work for the Singer & Winchester Retrieval Agency was the best career jump you’d ever made.

Grinning into your coffee at the thought of a big payday, you kept your eyes glued on the speaker in the middle of the fully kitted out breakfast littering the table. With a new case on the horizon, you didn’t even really need the extra shot of espresso in your usual morning double. 

Pent up adrenaline was already coursing through your veins prematurely and leaving you bouncing your leg under the large briefing table. If only to have some outlet for your energy until you could get past the necessary, but boring, planning part of the con and get a piece of the actual action. 

It’d been a quiet month, and damn it… You’d been going stir crazy waiting for another case.

You needed a chance to flex your muscles and ensure your skills were still sharp. There was only so much time you could spend training in the bunker’s gym before you needed real field training again. Your sticky little thieving fingers were itching for something to snatch. 

But first, you had to do the groundwork. No matter how much the little daredevil on your shoulder was ready to shoot first and ask questions later. 

Which meant you had to begrudgingly accept the manilla folder from Sam. Throwing him a small smile that grew wider as the tall man rolled his hazel eyes at you from the way you were nearly bouncing in your seat. The big guy was the youngest of the notorious Winchester brothers, who both topped more than one international most wanted list, and your intelligence guy. 

Information and data gathering were Sam's areas of expertise. Which was why he always helped Bobby with the planning and was the task leader on the ground when the big boss wasn’t there. Which was, honestly, most of the time. 

More than anything else though… Sammy loved his folders.

Every new con had at least one for each of you. Filled to the brim with everything you needed to know to make your next heist go off without a hitch. Yours even came with highlighted sections; color coded by importance and marking the sections you had to read. Since Sam knew you had the attention span of a toddler filled to the brim with sugar and high on a particularly strong strain of mischief. 

Though, truthfully, you did read the info in his precious folders. Every single word. After the briefings. But you’d never tell him. Even under the threat of torture.

Because, even though you loved it when you actually got to stretch your muscles and test your skills, there was no question you’d be dead and buried if it wasn’t for Sam Winchester. His thorough plans and backup scenarios kept your group alive and made you one of the most dangerous con agencies in the world. Hell, before you’d met Sam, your shoot first ask questions later attitude to your own thefts had nearly gotten you killed time and time again. 

Better yet, you were also less likely to be locked behind bars with him on your side.

Having graduated top of his class from Stanford Law, he was more than qualified to keep your not-exactly-legal little group out of trouble. Putting his skills and knowledge to good use; he kept  your plans airtight and made you impenetrable to any possible retribution. Legal or otherwise. 

Judges hated him, lawyers wanted to be him and criminals wanted to hire him. But he was all yours, and by that you meant your group’s. You yourself just saw the big lug of a man as a little brother. One with a massive collection of hair products, flannels and most importantly; one you just absolutely adored annoying. 

Which was why you’d take the fact that you appreciated his folder obsession to your grave.

---

“These guys are real monsters,” 

Bobby’s voice booming over the speaker system shook you out of thoughts as you quickly skimmed the pages detailing the target of your next heist. Grimacing down at the pictures of angry looking men that filled each and every page. All looking as if they’d been typecast for some typical mobster movie; fully equipped with glaring eyes, designer suits and not-so-pleasant dispositions. 

This group seemed to be European, and industrious in their crimes based on what you’d skimmed through so far and what Bobby was saying over the phone. Focusing on white collar cons, scams, money laundering, blackmail and whatever else could net them the biggest profit. 

Which in turn equaled big money for you. Score.

You liked big money. 

It was why you’d decided to become a thief in the first place. Or at least it was why you’d stayed in the business once you ‘broke out on your own’ as you chose to think of it. 

In reality, you’d never really had a choice in the matter, having been forced into a life of crime since childhood. Kidnapped before you were even old enough to remember your parents by a group of men and women in suits who looked suspiciously similar to the ones in the manila folder. Coerced into stealing to stay alive ever since you were old enough to swipe your first piece of candy. And by candy you meant the wallets and documents your adoptive ‘family’ asked you to swipe.

Once you managed to shake them off however, you’d stayed in it for the money. Since your lack of any formal education, or hell, an actual social security number or otherwise registered identity, made it hard for you to walk the straight and narrow. Then, since partnering up with the Winchesters, there was of course also the added benefit of getting most of that cash back to the folks they’d taken it from.

Just like the real-life vigilantes you were. Minus the capes, masks, and superhero names.

Dealing out your own special type of justice to the scumbags that operated just outside the grasp of what the judicial system was capable of tackling by handling the cases that somehow bypassed punishment. Either due to the bad guys having more lawyers, taller stacks of money or the right politicians in their pockets. 

On quieter days, you’d occasionally also steal from bad guys just to, well... Steal from bad guys. Take down a ring of pervs, cause a bit of financial ruin for a mobster or maybe just make life a little bit harder for a dirty politician. ‘Cause the days, and sometimes weeks, between jobs could get boring. 

Not to mention the fact that you were one of those weirdos that loved your job, and annoying baddies just made you all… 

Tingly.

You got to go scaling buildings, play around with high tech toys, trick the best security systems in the world and totally outshine Catwoman. Which wasn’t all that hard really. You were a hell of a lot better at your job than the feline comic book character. Even without the catsuit.

For the first time in your literal life of crime, you were happy. You were doing good. 

Though, as with every vigilante, the authorities most likely wouldn’t agree with you. However, what they thought didn’t really matter in your book... Your little agency of the best fighters, specialists and con men in the world were just too fucking awesome to ever get caught. 

As Bobby would say (sometimes repeatedly while you rolled your eyes at the speaker phone); in your business, confidence was everything. It was literally in the job title. You were confidence men (and women thank-you-very-much), or con men for short. 

You could walk into FBI headquarters, knock on the head honcho's door and easily gain control of the task force out to catch you if you wanted to. It was simply a matter of pushing the right buttons, putting pressure on the right paycheck and threatening the biggest, baddest guy there. 

Actually, rumors in the bunker suggested that Bobby already had the InterPol taskforce out to catch you in his back pocket. And you knew, with 100% certainty, that you’d helped out the Brits by acing your latest case up in New York. So, the MI5 kinda owed you… Big time.

This case, however, was definitely you doing good. And you doubted any government agency out there would stand in your way of taking down this particular group.

These greaseballs were digging their filthy paws into pockets they had no business being in. They’d set up a pretty basic charity scam; tricking money out of the pockets of good samaritans only to line their own and fund their criminal activities. All while actually being the monsters behind the problem they were raising money for. 

After creating the new highly addictive drug plaguing the streets of small-town America, they started the charity “combatting” the very addiction they caused. Raking in the cash from both sides.

It probably also doubled as a money laundering scam if you knew their type. And you did… Intimately. Their type had beaten everything you knew about infiltration and retrieval into you for years. 

Frowning at the words printed on the white paper, you pushed away thoughts of a ruined childhood that you’d rather not linger on just as your hacker and the beautiful brain behind most of your high-tech toys gasped across the table. Dragging you out of your own skim reading and rambling mess of a pre-caffeinated brain with her indignant grumble. 

“Kids? Really? Those soulless bastards are actually targeting teens and kids with that drug?”

Your best friend, Charlie, was the first to speak up past Bobby’s briefing. The words laced with disgust and seasoned with a frown as she devoured the information. Your brainiac best friend was, as always, one step ahead of Bobby’s own slower briefing across the speaker and nearly a full page in front of everyone else due to her speed reading.

The girl was a genius. A kinda scared and slightly neurotic genius, but a genius all the same. And you adored her.  

“They’re mafia… I don’t think they’re too worried about the morality of their scam,” Dean, the older of the two Winchester brothers, shot in. 

Though he was considered your ‘muscle’ and the group’s hitter, Dean Winchester was so much more. The trained mercenary, weapons specialist, mechanical engineer, and possibly also the sexiest man alive, was your group’s proverbial jack of all trades. Though he didn’t know you added that final item to his long list of qualifications in your mind. 

You were an expert at infiltration and retrieval, not an idiot. 

But damn it, that man should be illegal. And not only due to the little fact that he topped more than one most wanted list for his days as a mercenary, his qualifications, and his deadly skills. He was also hot as hell, and you might just maybe have the tiniest of crushes on him. 

Alright… So, the 50% of your brain that wasn’t occupied with thinking of your next con, was fully dedicated to thoughts of the sinfully sexy man. Both the innocent daydreams and the very, very dirty thoughts you indulged in behind closed doors. 

Whenever he was around, you were pretty much mentally tongue-tied like some pre-teen in a coming-of-age B-movie. Minus the bad prom plot, awkward jokes and high school stereotype ensemble cast. 

It wasn’t like you hadn’t been in relationships before, even if they’d mainly been covers for some persona you were playing… But, damn it, none of those men came even close to Dean Winchester.

And as luck would have it, he always sat in the seat right next to yours around the war room table. Which often made it damned near impossible for you to focus on the briefings and debriefings which were kinda integral to your safety and pocketing some not-so-hard-earned cash. 

Hence the need for highlighters, in different colors to boot, and a second read through in the safety of your own room. Far from the reach of his absolutely sinfully delicious arms. 

But heck, how were you supposed to focus on entry strategies when your eyes were constantly drawn to his perfectly proportioned and expertly trained body? 

It was impossible and also very, very mean to ask you to even try.

Especially when it came to those strong arms that you’d spent more than one night in your room dreaming about having wrapped around you. Caging you in his embrace and crushing your heated body against his; hard and soft in all the right places. God, what you wouldn’t give to have those big, calloused hands that were busy leafing through the case details work their magic across your body. Shaping you against him with a hand sliding up your spine or making you his good little girl with a hand wrapped around strands of (Y/H/C) hair… Or...

“Also means this is gonna be dangerous Bobby, these guys don’t mess around,” Dean’s follow up snapped you back out of your own dirty mind as you caught the briefest flash of forest green eyes looking your way. 

Your eyes barely caught his before you forced yourself to look back down at the papers in your own hands. Refocusing on a section that Sam had highlighted in yellow, underlined and circled. Yellow was good, it was bright and definitely not penetrating forest green.

Down girl….

“Neither do you son,” Bobby shot back over the speaker system. 

The heartfelt nickname still felt strange to your ears even though you should’ve already gotten used to it. Bobby raised the Winchester brothers; they were practically family. The rest of you had joined the group later, all scouted by either Bobby or the boys during particularly hard cases or through friends of friends. 

You’d joined two years ago. When they’d needed your particular skill set for a case. And, after nearly having ruined another case of theirs and them saving your life during one of yours, you’d kinda owed them one. The repayment had been a favor for one of Bobby’s friends; stealing back a family heirloom belonging to an older woman from a stereotypical dirty businessman. 

It was almost too easy. A simple pressure-based security system, that you’d completely bypassed by scaling the side of the building and descending in from the ceiling. The nice old lady had even baked you cookies when you went to drop the shiny rock off on behalf of the group. 

They were damn good cookies too. Chocolate chip, none of that raisin bullshit.

Sure, you knew Sam had somehow been behind it all. Talking the nice old lady into baking, in some sugary attempt to bribe you into joining the crew. Since your intelligence expert had put his skills to good use and somehow found out about your one weakness: baked goods. But still, it was the nicest theft you’d ever been part of, so you’d decided to stick around. Not because of cookies or owed favors, but simply because you wanted to use your powers for good instead of evil for once. 

“Mobsters usually also have some pretty good security, but nothing my toys shouldn’t be able to crack. So, if you crack their skulls, you can leave their passwords to me,” Charlie mused, smiling over at where Dean was looking ready to prove himself worthy of his foster father’s words of praise. 

She wasn’t lying either. Even without knowing their full layout, you knew her toys could crack any security system. 

You’d brought Charlie in after about a year with the team. Tagging her in when Sammy had been unable to hack a particularly secure government database over in Iceland. With a promise of getting her a specific limited-edition action figure she’d been eyeing if she helped you out. 

The girl was like an artist with a keyboard and a good WiFi connection. She’d been white-hatting it for most of her life. Though you knew she’d hacked a good few government databases, just to prove she could, even before she took the dive and became your literal partner in crime. Past her skills with a keyboard, she was also your first real friend, and you loved her like a sister. 

She wasn’t really cut out for a life of crime though, considering her skittish personality. So, for most of your decade-long friendship, you’d always kept her out of your more illicit schemes. But what Singer & Winchester Agency was doing... That was right up her alley. What with her massive love for anything vigilante. Especially if it came with capes, superhero costumes and secret identities. All the things you’d rather do without. 

In many ways she was your opposite; the angel on your shoulder where you were the daredevil on hers.

She’d readily decided to help you. Always willing to help a friend in need, especially if it came with the added bonus of mint condition collector items. Even if said promise included speaking to people she didn’t know. 

Which was possibly her least favorite thing in the world to do, other than public speaking to crowds larger than three. Especially when said strangers were, like you, some of the most wanted criminals this side (and likely on the other side too to be honest) of the Atlantic.

Once she’d seen the tech the boys had set up in the bunker however, she’d been sold. Enough to tell you to keep your bonus bribe. Especially since Dean was always there, ready to help her build whatever crazy gadget she dreamed up. As always, your nefarious group of con men always knew which goodies to use to lure someone into joining the agency. With you it had been home baked goodies, and with Charlie it was a literal tech lair. 

That… And the figurine had still made its way to her as an early birthday gift just a month later anyway.

And so, your group had gotten a little bigger. All of you being glorified criminals with hearts of gold had of course made for a weird group dynamic. Yet, you somehow made it work. Even when the newest member of your group joined not all that long ago.

“They’re quite the mixed group. Swedish, French and… Russian huh… My Russian might be a bit rusty, but if I brush up on it I should be able to pull it off,” Your latest recruit, Castiel, shot in as he looked at the papers with his usual tell-tale frown of concentration. 

The guy was more or less still a mystery, wrapped in an enigma, wrapped in a trench coat to you. Though you were pretty sure his name was fake. 

Castiel, or Cas for short, was your grifter. The man with the face of an angel, who could trick basically anyone into trusting him unconditionally. 

So of course, though you liked the fella, you didn’t really trust him. Especially not since he’d dropped in from out of nowhere only a few months earlier. Pulling your collective asses out of a hellish case at the last minute and helping you put a crime lord behind bars.

He’d apparently worked for the big guy before… As in, working for the president in some manner. Secret Service, CIA, FBI, or one of those, if not all of ‘em. But since he quit and now worked in the law’s gray area, he was considered a threat.  At least that’s what he’d told you and what Charlie had managed to confirm through some very secret databases. Even if 80% of the documents were redacted.

He was nice however. And you’d grown close to him over the last few months since he was normally your partner on heists. Or, mainly, you’d taken a shine to watching Charlie get more and more frustrated as he shrugged off her pop culture references, not understanding any of them. 

Apparently, working for the president left little time to Netflix and Chill, since half of your best friend’s references went straight over the grifter’s head. If you didn’t know better, you would’ve thought he’s spent the better part of his life somewhere off-world on a spaceship. 

Actually…. You didn’t know better. Considering his language skills, the man was nearly otherworldly. Easily emulating any character perfectly once he had his role to play.

---

That was your team.

Bobby, the big boss. Sam for intel & planning. Dean for combat and security. Charlie for anything tech and hacking. Castiel if you needed someone’s pants charmed off. And you; the reformed thief turned infiltration specialist, with sticky fingers that could easily retrieve whatever the baddies of the week had stolen.

Even if you might not know everything about each other. They were your friends and your only family in this messed up world that was filled to the brim with mobsters and other monsters. Each one worse than the one before, and every single one of them so much worse than what hid under people’s beds at night. Because your monsters were very much real. And very much out to kill you. 

All in all, you were a ragtag group of master criminals turned modern day Robin Hoods. Stealing from the criminal underbelly of the great US of A, and giving to the… Well, most of your clients were wealthy enough to hire you. And some might even have their own skeletons hiding among the designer shoes and dresses in their closets. But they were all law-abiding citizens who didn’t deserve the hand life dealt them. The rest was just semantics.

Plus, the boys always insisted that a cut of your earnings went to some charity or other. Normally some organization that stood in juxtaposition to the bad guys you’d just taken down. Just to pour an extra ounce of salt into the wounds of the bastards.

“So, if you’re all done adding your little color commentary and reading the briefs, let’s move on,” Bobby’s gruff voice sounded slightly exasperated across the speaker. 

Which honestly wasn’t anything new. 

It was hard enough to get one of you to listen; all of you at the same time was a freaking miracle. Unless you were out on a job that was, then you were a well-oiled con-machine.  

None of you spoke up, simply nodding at the phone, though you knew your boss couldn’t see you. At least you were around 75% certain he couldn’t. Though you wouldn’t have put it past him to equip your hideout with some hidden cameras. Either way, he was sure to interpret the silence for compliance. 

“Good. The plan is to steal back the money, get the drive where they keep all their sales records and personnel files and preferably also financially cripple their organization just enough to stop them from trying anything like this scam again. Cherry on top would be to put the Al Capone wannabe running the whole show behind bars,” He summed up over the slight crackle of the speakerphone. 

All in all it was pretty simple, as far as plans went. You wouldn’t have to break into any top-secret government facilities this time around at least.

“So, what’s the next step, boss?” You asked, grinning at the rest of the group in anticipation of the next heist. Letting the folder drop unceremoniously down onto the big mahogany table, you kept your eyes on the speaker. Though you knew it would annoy Sam to see you treat his little manila baby so poorly.

“First… We bring in the bad guns,” Bobby said, causing Dean to groan. The rest of your party joining in like an exasperated chorus only a split second later. 

That nickname could only mean one man… Sure, you all had your own backgrounds in the not-so-law-abiding, but that guy easily made each and every one of you look like perfect little angels. 

“Crowley… Really?” Sam asked with a tired sigh as he pinched the bridge of his nose. Confirming what you’d rather have him deny just as the groans died down.  

Big bad was coming to play. 

Fan-fucking-tastic… 

---

Next

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

Dean Winchester Tags: @ria132love @woodworthti666 @defenderrosetyler @akshi8278 @justanotherwinchester @lyarr24 @torn-and-frayed @all-will-be-well-love @wearesuchstuff1 @thefridgeismybestie @adoptdontshoppets @starsandmidnightblue @screechingartisancashbailiff @septixtrash @punof-agun  @deandreamernp @justagirlinafandomworld @sexyvixen7 @justrealizedimmascifygurl @globetrotter28 @siospins2 @iprobablyshipit91 @mrsjenniferwinchester @leigh70

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

Your Cinderella comparison kinda fell apart when you involved Crowley however. Was he supposed to be the evil stepmother? The cat? Lucifer was a fitting moniker for the self-proclaimed king of the underground. Or maybe the pumpkin turned carriage that brought you to the party? Either way, the greased up Scotsman had been in top form as far as sass went the whole pre-party briefing. 

Making comments about your less-than-fairytale-princess choice of dress and eyeing you up in a way that once more brought back Dean’s protective big brother rage. And left you feeling less than ready to party from the reminder that he saw you as family, nothing more. Even when you’d dressed to absolutely freaking slay.

After all, your fashion choices were nothing like Cinderella’s; nowhere near as shiny and poofy.

You had opted for sleek, short and black. The dress was easy to move in, which was paramount to any outfit you wore on missions. Hugging your curves tight in a way that seemed more painted on than actual cloth as it flowed down your body before stopping right above the knee. The deep open back, paired with your (Y/H/C) hair in an elegant updo that highlighted your neck and framed your face, left little space to hide your tools. But luckily you had a walking, talking handbag called Dean Winchester with you. So, past a few small toys and a set of throwing knives strapped to your thigh, he’d helped bring in the rest. 

Ahead of you, Charlie was wearing a stunning red dress that you’d helped her pick out from the large treasure trove of recon outfits hiding in the bunker. Contrasting beautifully against her pale skin and easily long enough to hide her little gadgets. With a convenient slit down the side so she could get to the card stripper strapped to her thigh without anyone catching on.

The boys… Well, the boys were sadly not in dresses, but in their usual high end tuxedos used for cons of this type. Lucky bastards even had flat shoes on. Damn how you hated the dressy undercover missions. You were much more comfortable in sneakers, infiltration clothes, and harnesses - rather than stilettos, push up bras, and cocktail dresses.

“You ready?” Dean’s voice echoed as it reached you both directly and in your earpiece. His green eyes rested on you and you could feel the heat of the large hand that was softly sliding down your lower back, but you knew he wasn’t really speaking to you. 

No, the question, that you still pretended to answer with a nod and a smile in case someone overheard, was meant for Sam. Situated across the street in the apartment you’d acquired yesterday (not all that ‘legally’ mind you) to use as your base of operation for the night. Dean’s eyes only betrayed that fact with a small, nearly missable glance to the side. In the direction away from the glitz and the glamor that was drawing the eyes of the crowd around you.

“Yeah, I have eyes on you. As soon as you reach the door sensors they’ll stop workin’. You’ll be able to get in with all your weapons and tech without setting off anything,” Sam’s voice came through loud and clear in your ear as you kept a fake smile plastered on your lips. Your back straight and eyes focused on the damned mansion ahead as you pretended that your heart wasn’t about to beat out of your chest from the proximity of a certain criminally handsome (no pun intended) Dean Winchester. 

Not only was he standing close enough to steal your breath away with the slight spice and leather scent of his aftershave. But his hand would reach out at seemingly random times to brush against your arm or rest against your bare lower back, leading you forward through the crowds of partygoers that had all seemingly decided to show up at the exact same time. 

Alicia was the type of woman that was used to being escorted around, unlike your own fierce independence. And since your cover for the night was as Dean’s date, that meant he was always within reach, ready to slide calloused fingers against your electrically sensitive skin. 

Hell, even your cover; not a side piece, or a girlfriend. Just… A date. It was as painfully vague as the rest of Alicia Cooper’s background story. Which meant Dean had full freedom to interpret that as he saw fit while he escorted you towards the line in front of the door, right behind Charlie and Cas.

“And are we sure we can trust the green giant with this? I thought he knew his greens and veggies, not… Technology,” Crowley’s voice was low as it reached you through the small piece of silicone in your ear. The damned man always had to season every social situation with sass. That British humor really wasn’t your cup of tea (pun totally intended). 

“Yes Crowley, we can… Charlie and Sam created the damned software we’re using to hack into the system and I trust ‘em more than you,” Dean shot back before his younger brother could defend himself. As always playing the protective big brother, no matter the enemy. The smile on his lips contrasting with the whispered words as you pretended to straighten his tie to give him a reason to keep his head down.

“And even so, my tech is great. I made it to be undetectable, even the chips I added to your weapons and the alloy (Y/N)’s knives are made out of. The sensors wouldn’t pick them up even if they were military grade,” Charlie pouted from ahead of you. You didn’t need to look over at her to know she was moping. Though you knew Castiel would do a good job playing it off as her being a slightly demanding date; bored of waiting in line.

She’d considered the extra precaution of momentarily shutting down the sensors as unnecessary from the start. Her little gadgets were like her babies. To her the extra measure was a direct blow to her ego and, worse yet, her toys.

“We trust you and your awesome gear Char, it’s just a precaution,” You shot in with a smile that was aimed at Charlie, but shared with Dean as you brushed some non-existent dust off of his shoulders. Before allowing him to straighten back up and put a large, strong hand low on your back again, where the dress met with bare skin. The direct touch of calloused fingers against slightly chilled skin sending little shots of electricity through you that threatened to blow a fuse in your brain. 

Which was… Less than ideal. After all, you needed all your fuses functioning if you were gonna pull the job off in the middle of the damn snake pit masquerading as a party.

“Enough of the squabbling kids,” Sam said through your earpiece, which honestly made you want to squabble more, since he was younger than you. Still you kept your mouth shut as the kid kept speaking. Silently plotting a revenge that involved exchanging his protein shaker collection with Disney themed sippy cups and maybe sneaking a few bibs into his closet for good measure. 

Kids… 

You’d show him who the actual baby of the team was.

“This is the entry plan we decided on. Cas, Charlie; you guys are next in line, together with Crowley. Behave. Sensors shut down in three, two, one…”

---

To quote the poets of days long past; the party was nice, the party was bumpin’. 

Ok, so that was the Baha Men… But quoting pop music from the 2000s always annoyed Dean, who insisted the only real music was classic rock. So, you’d developed a habit of doing it. Since your style of flirting was a little less Casanova and a hell of a lot more kindergarten hair pulling. 

Though, truthfully, the party was more fancy than nice, and more classical music and people talking about their yachts than bumpin’. Which in turn, made it so totally not your scene. You liked your parties to be bumpin’, just like you liked your bad decisions to be fuelled by alcohol and adrenaline. 

You were a simple woman, with simple needs. Fancy, wasn’t one of ‘em.

Groups of wealthy men and women stood in small circles scattered across the polished tiles and spoke in polite low tones about how much money they had in offshore bank accounts and how amazing it was of them to bypass their evil deeds and greed to give what to them was considered pocket change to the poor and needy in return for tax breaks and untraceable laundered cash. Or maybe they were talking about their villain lairs; complete with white cats, swivel chairs and shark pools, or something… 

Hell, it was all the same to you. You could barely focus on taking a step forward with Dean’s hand so securely around your waist. Which was real bad… You had to focus. 

Across the large open space, you could already see Castiel working the room and talking to the sleaziest of sleazebags with Crowley. His hands easily dipping into pockets to get wallets and ID cards as his words and smiles made them share little tidbits of information about themselves that allowed Sam to work his magic across the street. 

Cas could probably charm the pants of a nun. Though you’d rather he didn’t aim to prove you right. Considering he was a very vocal atheist, claiming there were just ‘too many caveats in faith’, it just seemed extra blasphemic to even consider letting him near a nun. Since he’d probably take it as a challenge. Though he did have to pose as a priest on a con once; which you took great pleasure in reminding him of whenever the opportunity arose. 

Father Simmons had been the least pieous priest that small backwater town had ever seen, but at least you’d managed to infiltrate the cult. Shutting it down and proving to the town, and the world, that the religious fanatisism had just been a cover for human trafficking. Like a Scooby Doo episode; only instead of pulling off the monster’s mask to reveal a ‘Mr. Creeps’ you’d revealed an even bigger monster.

All thanks to Castiel’s brilliant work charming his way into the cult. And of course, Charlie’s techy backup sleuthing that had helped you find, and rescue, the victims.

This time however, Charlie’s work was a little less background and a lot more field work. As she had left Castiel’s side, as planned, to plant a few cameras that would allow Sam to have eyes in the house as well. Since you’d need other angles than the in-house security system that your two wunderkids had already hacked. 

Only doubling back from time to time to take the cards off of Cas’ hands and skim the information through the card reader she’d attached to her thigh or by scanning it with the button cam hidden in the brooch on her dress. Before a small giggly touch of her date’s shoulder had the card right back in Castiel’s hand to deposit it back into pockets before the mark even noticed anything was wrong. 

Even Dean was hard at work; whispering guard numbers and visible weapon types through the earpiece. 

Hell, you were the only one not fully focused. Which was bad. Considering the heist kinda, sorta relied on you finding the damned safe. You had to stop acting like a fucking teenager, high on daydreams and drunk on wine coolers and instead be (Y/N); super thief extraordinaire. 

That’s why you were there after all. Your job was to find the fucking safe, as well as scope out possible entrances and exits for the actual heist. Your job was definitely not to stand around like a complete greenhorn and think about all the things you wished Dean’s hands would do to you. Oh, no sirree, that job was for late nights under the covers (Y/N), not master finangler of all things shiny (Y/N). 

Priorities... First you’d trick the mafia and take all their not-so-hard-earned money, then you’d have some hot and heavy me-time. Never the other way around. It just wasn’t proper work-place etiquette. 

“Let’s start casing the other rooms. We’re too out in the open, no hiding spots. For us or for a safe,” You spoke the words under your breath. 

Slipping away from Dean’s hand, you took his hand in yours instead. Pulling him along further into the room with a louder giggle that seemed like it’d suit Alicia perfectly. Past the wandering eyes of bored upper-class wives that were not even trying to hide how they were devouring the man by your side.And out of earshot of their partners’ ‘economically pornographic’-conversations. Their husbands looked like they were about to straight up orgasm whenever someone said inflation or money laundering and it was… Disturbing.

“Castiel, see that big guy with the obvious toupee and suit jacket that’s two sizes too small? Yeah, he’s one of the big sharks in the criminal cesspool. Might wanna go introduce yourself,” Sam’s voice came through your earpiece just as you rounded the corner into the next room, which was just as flooded with human monsters flaunting their riches as every other room. 

Throwing a quick glance over your shoulder you saw Castiel start to move, Crowley right beside him. Your inside man’s muttered complaint about being able to tell Cas that without Sam’s interference easily reached you, even from halfway across the room, through the vibration based earpieces. 

Seriously, those things could pick up people’s wandering musings and dirty daydreams if you’d wanted them to. Which you really didn’t. Your mind was already a rambled mess without outside interference thank-you-very-much. 

Still, except for the unnecessary running commentary, big bad had come through for you. The guy hadn’t only gotten you tickets to the underground party masquerading as a Charity Fundraiser, but he’d also ensured to namedrop Castiel’s cover name as a “top investor”. So Cas had every way in to shake hands and stroke egos. Leaving the rest of you free to do your jobs and scope the place out. 

“Charlie, great job on the cameras and mics, that’s the last one. Make your way back to the main room to back up Cas and Crowley,” Sam’s voice continued to give orders over the earpieces, though none of you ever complained. 

No matter how much your stubborn crew could butt heads before a heist, during the actual job you’d always listen to Sam. The guy was like a chess master and you were his little criminal chess pieces. If you did as he told you to, you’d make it out of any sticky situation just fine. 

“People keep trying to talk to me. I’m not good with this undercover stuff,” Charlie groaned in response. Yet, as you finished walking through the other room and moved out to the dining room area, you still caught sight of her red dress disappearing through the door back to the main hall. Soldiering up and doing her duty even through her massive fear of social interactions. 

“You do your LARPs and conventions, just do what you do there,” Dean chuckled next to you. The deep vibrations of that low laugh delivered right to your ear nearly made you stumble over your own feet with a sudden case of vertigo. 

“I’m someone else when I LARP, I’m a queen. Same with cosplaying; Wonder Woman can talk to people… Me? Not so much,” Charlie’s voice sounded panicked over the little earpiece and you wished you could go help her, but you had to stay in your role and do your job. 

You had a safe to find, and unfortunately it was nowhere to be found. The dining room was clear too, and you were running out of places to look for the damned thing. Though you’d basically already mentally mapped out their whole downstairs security system and at least 7 exit strategies. So there was that.

“You’ll be fine Char, after we get through this we’ll go to your favorite comic book shop, I promise,”  You said with a small smile, catching Dean smiling at your words as well.

“Ok, alright… I can do this. For comic books and funko pops,” Charlie’s words were punctuated by a few deep breaths and one or two muttered creative swear words. But you knew she’d do her part and she’d do a hell of a good job of it too.

“That’s our girl, Charlie,” Sam’s voice was less master commander and more big brother as his warm chuckle came in over the comms system, before it returned to its serious tone and your strange little family was once again all business. 

“Dean, check the guys by the door, I’m seeing what looks like a holster on one of Charlie’s cameras,”

--- 

You’d scoped out the whole bottom floor, which was massive, but disappointing. Not when it came to things worth stealing mind you. With the exception of the one forgery you’d clocked the day before, everything else was actual originals. You could buy an island from the value of the art displayed on the walls alone. But there were no safes, anywhere. 

Damn it. 

Sure, you’d done the other parts of your job, but you needed that safe. Bobby was working hard on the backup plan and Castiel had gathered up enough info for you to be able to pull a turnabout if it came to it and pit the criminals up against each other. But that was still plan B, and plan B wasn’t perfect. 

Plan A had been... Perfect that was. Until the whole issue with there not being a damned safe on the first floor like your insider information had promised you there would be. 

Petty crooks; you didn’t trust ‘em any further than you could throw ‘em... No, scratch that, you could throw people pretty damned far. As far as Crowley could throw ‘em. Yeah… The guy was an ultimate movie baddie, but he didn’t look like he could throw other bad guys all that far. Not only would that end up wrinkling his suit, but the man’s favorite super power seemed to be more sass, less Superman. 

However, just as you’d been about to inform the team of your failure to locate the safe, Sam’s voice interrupted you across the comms. Cutting off his own words to Cas about the hidden dealings of the corrupt politician in front of him that the grifter could use to twist the man around his little finger to instead speak to the whole group.

“Shit, ok… So five guys, including the main honcho, just came down from the second floor. I think our intel’s bad. The safe is probably up there. This isn’t the first time tonight I’ve seen people go up and down those stairs,” Sam’s words were met with strained silence as you all waited for the big guy to rework the plan for your entry and exit and work the new information into it all. 

It wouldn’t be easy, and even over the comms channel you could nearly feel the strained worry and tense backs of your team members. You had no cameras upstairs, so no matter the plan it was going to be a risk. 

Still, you needed eyes on that safe.

“(Y/N), I need you up there. It might be dangerous, so stay low and be careful,” Sam’s words were hesitant over the comms channel. The big guy never liked sending anyone from your group of merry men into a possible dangerous situation without a backup plan. But you had no choice. 

You wouldn’t get this chance a second time around. You had to get eyes on that safe before the party was over, if not plan A was shot and you’d have to move on to the rest of the fucking alphabet, which was not nearly as bulletproof as a good solid ‘A’.

Sam’s words perked you right back up out of your funk, even with the added element of danger… Hell, you couldn’t lie to yourself, you loved the danger. But better yet; you had another chance to find the damned safe. You really didn’t like letting the team down, not when they’d done so much for you. And… As an added bonus; your poor heart could get a break. 

Spending a full evening with Dean’s arm around your waist had taken its toll on your nerves. Add to that the eyes of the many women eyeing him up as if he was the tastiest piece of sweetness in the sugar bowl, and you weren’t a happy camper. You were his arm candy, he wasn’t some tasty treat they could sneak a bite off while their husbands’ heads were turned. 

Upstairs was good. Upstairs would keep you from punching people. 

Alicia probably wouldn’t punch people...

“Alright, leave it to me. Downstairs’ fully scouted, I’ll check upstairs and give a full report after the party,” You tried, and mainly failed, to keep the excitement out of your voice as you started towards the stairs. Stepping away from Dean’s side for the first time that evening, you almost immediately felt cold. 

Your poor heart could only take so much however, so the cool down was a welcome break from the fire burning low in your core. Yet, you hadn’t gotten more than two steps away before Dean’s hand was lightly circling your wrist and his voice was in your ear. Both directly and through the earpiece, as he pretended to murmur sweet nothings in your ear to hide his words from the rest of the party.

“I’ll go with her,” His words were not a request for Sam to include him in the plan. No, it was a statement; one his tone made it clear there was no use arguing against. He wasn’t letting you escape to the second floor to calm down. 

Clearly the damned criminally handsome man had it out for your heart. You didn’t know what the stupid muscle had done to make a nemesis out of the Dean Winchester. But considering his presence was causing your chest to take a beating of its own design, it must have been real bad. 

“We don’t know what or who’s up there. An extra pair of hands could be good,” He added when Sam stayed silent, not letting go of your wrist or moving until he heard a mumbled sound of agreement from his younger brother. Damn it. Why did Sam choose that moment, of all times, to actually agree with his big brother on a plan? 

Lawyer up Sammy boy. Argue and protect your thief’s poor heart! 

Unfortunately, your damned techy earpieces couldn’t transfer silent cries for help, yet. And so, you were left biting the inside of your cheek as you tried to keep your body from reacting to how Dean’s fingers were stroking against the pulse point on your wrist. 

“I can take care of myself you know,” Your words were more a weak huff than an actual statement as you started walking. 

Forcing your voice to keep from trembling as you once more stayed side by side with the man who made your heart practice extreme sports in your ribcage. Your eyes stayed locked on the doorway leading to the stairs as you forced yourself to walk slowly. Your shoulders relaxed, pace unhurried and movements languid, as if you were just enjoying the party and milling about. 

“I know that sweetheart, I’m not going up there for you,” Dean said with a chuckle. Adding a dramatic pause to give you that boyish grin that always made your stomach fill with damned giant eagles, since you’d used up your supply of butterflies in the first 6 months of working with the man. 

“I’m here for the poor fool who tries to mess with you,” 

Smiling in spite of yourself, you let out a breathless laugh at words meant as a nod to your first proper meeting with the weapons specialist and former special forces soldier. Not really a Hollywood movie meet cute, but a favorite memory of yours nonetheless.

He’d been the one they’d sent to recruit you to the modern day Robin Hood crew, and you’d been… Kinda jumpy back then. Constantly being on the run from the mafia, Interpol, FBI and God knows who else, did that to a girl. So, instead of exchanging business cards you’d kinda, sorta… Flipped him flat on his back and threatened to flatten his pretty face with an ancient bronze statue. That gaudy piece of ancient art had been heavy as fuck. Though it was nothing of extreme value of course. 

You’d been paranoid, not stupid. 

Things had luckily calmed down fast enough once you recognized him from previous run-ins. And, instead of actually breaking his nose, which should be considered a crime in and of itself, ‘cause damn… You’d talked things through and you’d finally let him up from where you’d pinned him to the ground. Still, Dean never let you forget that you actually got the drop on him. Though he was never upset about it, more impressed, considering his own impressive track record. 

“You’d know wouldn’t ya?” You shot back with a small smirk. Leaning against the wall; you pretended to be enjoying a more private conversation by the stairwell while you waited for an older couple to pass by. Just barely stopping yourself from shooting the older woman an annoyed glare as she clearly admired Dean’s ass in the tailored designer slacks.

“Oh, yes… I definitely would,” Dean’s words were punctuated by a wink and oh God… That sexy motherfucker was trying to kill you, you were sure of it. 

The whole night was just an elaborate assassination attempt. Warning bells were ringing in your ears as the poor crew manning your brain ran for their lives before the imminent implosion that was sure to follow as your heart beat loudly enough to show up as soundwaves in your eyes. Which you, not so sneakily, tried to hide by checking if the coast was clear.

Focus. 

Forcing out a small laugh you set your plan into motion and moved up the stairs at a pace that made it seem like you belonged up there. 

Not too slow, and not too quick. Just like they taught in thief school. If there was such a thing as a thief school... Hell, even if there was, you'd probably be expelled the first damned day. Considering how often your brain jumped to Dean instead of shiny sparkly treasures lately. And considering that you’d never really been good at sitting still, listening to authority figures, listening at all really, or paying attention to anything for more than two minutes at a time. 

Or, hell, math… You hated maths. 

As Dean followed you up, keeping close and at the same time ensuring no one saw you, you steeled your heart for your alone time with the perfect freaking specimen of a man. Taking a deep breath, you tried your hardest to turn off the part of your brain that was inexplicably tied to your heart in what was possibly God’s idea of a stupid prank on the human race. 

Find the safe, that was all you had to focus on. Find the goddamned safe and then act out the entire library of love struck teenage movie scenes and the more R-rated extras in your mind when you were safe and sound back in your room at the bunker.

It shouldn’t be that hard. You were a professional after all. You’d been in the business for a very long time. 

Yeah, you got this... 

If only you could stop thinking about the fact that the bedrooms were probably up there too. Egyptian cotton bed sheets that were just begging for someone to mess them up. 

Fuck, you didn’t have this; you were screwed. Thoughts like those were exactly why you’d worked alone before joining the team.

Safes, not bedrooms. Safes.

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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 @siospins2 @iprobablyshipit91 @mrsjenniferwinchester @leigh70 @djs8891

Dean Winchester Tags: @ria132love @woodworthti666 @defenderrosetyler  @akshi8278 @justanotherwinchester @lyarr24 @torn-and-frayed @all-will-be-well-love @wearesuchstuff1 @thefridgeismybestie @adoptdontshoppets @starsandmidnightblue @screechingartisancashbailiff @septixtrash @punof-agun  @deandreamernp @justagirlinafandomworld @sexyvixen7 @justrealizedimmascifygurl @globetrotter28 @siospins2

Well… ‘Ready’ was relative. But just like a doctor’s appointment you dreaded or phone call you really didn’t want to make, you’d talked yourself into getting it over with. After all, Charlie had promised she'd buy you ice cream and veg out on your bed to a full season of whatever caught your fancy on Netflix after your heart was pulverized.

Sure, her exact words had been if. If Dean broke your heart. But you knew better. Your best friend was just a little more of an optimist than you. Charlie had always been a little more ‘glass half full’, whereas you tended to be on the side of ‘that glass has definitely been poisoned and I’m going to die’. 

Ok, so Charlie was a hell of a lot more of an optimist than you.

Luckily, her optimism seemed to be a good influence on the cards fate dealt you that morning. Since your walk to the kitchen, and subsequent inhalation of a dangerous amount of caffeine, went by uneventfully. Undisturbed by any Greek Gods of the Winchester variety. And before your brain had even fully accepted the onslaught of coffee poured over it, you were walking towards the gym. Charlie trailing behind you with her head in her little tablet. Prepping for a day of breaking down firewalls and cyber terrorizing some bad guys. 

“Are you sure you don’t want to come with me to the gym? You can try to have your lasers catch me again? Or maybe test out that taser based system you’re developing? I don’t mind being shocked. I promise,” You asked, hell, pleaded, and you weren’t too proud to admit it. 

At least having your best friend there acting as your human shield might help lessen the blow to your heart if Dean decided to come to the gym early. Even though he normally started his day at the gun range, checking his massive collection of all things… Shooty. 

“No can do. I gotta get to work getting us the info we need for the case we’re on. Remember that? Big bad drug dealing scammers and all of that nastiness?” She said, raising an eyebrow as you pouted at her, hoping to emotionally blackmail her into being your… What would the opposite of a wingman be? Thigh man? Breast man? Fuck, whatever part of the chicken was the least cowardly one..  Being your that. 

“Pleeeease Care Bear? You love me right? You’ll protect me right?” You groaned, dragging your feet as Braniac HQ came into view. Though you knew there was nothing that could tempt Charlie away from her precious tech when there was some good ol’ fashioned hacking to do. She always had to be the responsible one. 

“You’ll be fine (Y/N). I’d like to come and offer you some moral support, but as you might have guessed… I have questionable morals, considering I joined this crew and all. And on the topic of morals, you know I have to go and do some morally gray hacking right now,” The red head sighed with another patented roll of her eyes as she stopped in front of the door to her office and reached for the door handle to cut off your puppy dog eyes and further (failed) attempts at talking her into coming to the gym with you.

“If I’m not fine I’m holding you responsible. Remember! You promised me ice cream,” You groaned in defeat as you walked backwards towards the gym to keep your best friend in view. If nothing else you wanted verbal confirmation that she would pay for the cartoonish amount of ice cream you’d need to suture up your broken heart. 

“I’ll get you all the ice cream you could possibly ever eat... If things go wrong. Now go, burn off the rest of that alcohol and get your reps in before the next phase of the job. You’re our ace on this one (Y/N), so get your head in the game,” Charlie called out after you. Keeping her words as cryptic as possible in case someone from your team of sleuths were within hearing range. 

“Love you too…” You sing songed with a sarcastic groan as you turned on your heel and hurried towards the gym. Hoping against hope that you wouldn’t run into Dean on your way to your workout. 

---

Apparently, whatever bribe Charlie had slipped the fates had rubbed off on you. As you were left alone to work through your tense muscles and the remaining nerves that were still stubbornly strained from whatever the hell that was in the closet with Dean. Even Sam, who normally lived in the gym if he wasn’t in the HQ was nowhere to be seen. And though it meant you had no one to spot you, you were happy to have the gym all to yourself that morning. 

As always, a workout was just what the doctor ordered. Though the doctor was clearly one sadistic bastard, considering how hard you were pushing yourself. 

The repetitive motion of the reps and the protest of your muscles being pushed to their limits left little thought for how one of said muscles would soon be pushed well past its limits and into heartbreak territory. But after pummeling your muscles into submission and reaching for your water bottle, you felt strong. Ready. Like you could take on the world. 

Or at least you had thought you felt strong… Until Dean stepped into the damn gym just as you took a sip of water, making you choke on it. Yeah… You were totally not ready. You needed a shower first. Yeah! A shower, and then you’d be ready. You weren’t running away. You were showering. Cleanliness was next to godliness after all. You couldn’t have The Talk all hot and sweaty. It would send the wrong message. 

“Gym’s all yours…” You croaked out as the coughing fit from your near drowning death on dry land died down. Grabbing your towel just as Dean took the first steps towards you, you used that roadrunner speed you were so damned proud of and slipped past him out into the hallway. 

But Dean was clearly in no mood to let you run from him again as you heard him follow you out of the gym and down the hall towards your room. Not that you blamed him… You did need to talk, but still…

Could you knock him out to get away? 

No. You couldn’t knock out your partners in crime. It would be bad workplace etiquette. Human Resources would fire your ass. Well, they would have, if you had an HR department. Something to bring up to your non-existent union. After you successfully escaped your hitter and formed said union. So many things to do, so little time to have your heart broken. 

You nearly made it to your door before Dean caught up to you. 

Wrapping a big, warm hand around your bare upper arm, he turned you to face him with a small tug. Just as you were reaching for your door handle. Damn it… No more running away. Time to be a big girl. 

Sighing, you kept your eyes on Dean’s chest. Unable, and unwilling, to look into those hypnotic green eyes in fear of what you would see there. He was probably pissed. Hell, if the shoe was on the other foot, you definitely would be. But then again, the Dean Winchester would never run away from his problems. He’d just beat them to a pulp and saunter away victorious. 

“We need to talk,” 

Such dirty words, from such a damned pretty mouth. His deep voice sent shivers down your spine as you finally lifted your eyes up enough to see the steely look of determination, marred by frustration, in his eyes. His jaw was set, and brow furrowed as he looked down at you. 

“Ok, but not here,” Though the feel of his calloused fingers against your sensitive skin was making it hard to even form a coherent thought, you finally managed to push the words out. Casting a wary glance around the empty hallway, the words left you in a breathless huff. You really didn’t feel like having an audience around for this. Hell, even Charlie, though you’d nearly begged her to stay with you only an hour earlier. 

Looking up at him again after making sure the hallway was indeed deserted, you caught him glancing towards your bedroom door, and for a second you considered it. But that seemed like a very bad idea. Your dirty mind was automatically going to the soft bed hiding behind the wooden door. 

The very bed that had featured in so many of your fantasies. 

Then again, most of the rooms in the bunker had featured in one of your many fantasies about the dangerously attractive hitter. Alternative uses for the gym equipment, that sinfully soft couch in the rec room, or the many available surfaces in the industrial sized kitchen… Hell, even Dean’s favorite car, his baby, was a recurring supporting character in your daydreams. 

You had a very active imagination, at least when it came to one Mr. Dean Winchester. 

But, even so, your bedroom… Nope, no way. Not only was it the stage for most of your dirty day dreams, it was also the writers’ room for them. Not to mention that the damned walls were cardboard thin. 

You needed somewhere else. Somewhere private and preferably soundproof. 

With a sigh, you nodded down the hall and took a step away from Dean’s dangerous proximity. Before being pulled right back as green eyes blazed into you and his strong jaw, peppered with the shadow of a stubble he had yet to shave, ticked. Clearly thinking you were trying to run away again. 

You would have argued that you wouldn’t run away. But, hell, your track record spoke for itself. So instead you just sighed and repeated your earlier nod down the empty hallway, adding a verbal clarification as you shrugged off Dean’s grip on you. Clearing your throat to get rid of the breathlessness his proximity always left you with.

“Follow me,” 

“Where are you going?” Dean still sounded wary as he fell into step next to you. His toned body was still tense… Ready to act if you so much tried to run. 

“To hell, most likely,” You quipped back. You might not be able to physically outrun the hitter, but that didn’t mean you had to willingly walk like a lamb to slaughter. At least not without putting up a bit of a fight.

“This isn’t really the time for one of your bad jokes (Y/N),” Dean groaned through gritted teeth as he lifted his hand to reach for your arm again. Seemingly ready to talk it out right there in the hallway if you didn’t give him a straight answer. 

“Somewhere we can talk,” You shot back quickly before he could break your heart in full view of whoever decided to take a casual stroll down the bunker hallway. And just in time, it turned out. As you felt just the slightest brush of calloused fingertips against your bare arm before Dean dropped his hand and fell back into step next to you. 

Taking point, you led him to the least sexy place you could think of. Or… Hell, that was a lie. You found the gun range plenty sexy. All action, gunpowder and lead. The vibrations of a good shot aching through your bones and lighting your veins on fire… It was goddamn porn. 

But fuck it, anywhere could be steamy if a certain Dean Winchester was there anyway, even a mobster’s closet. And at least the gun range was soundproof, had a red light you could turn on to show it was currently occupied, and the door locked. You had to take it. 

Especially since you were stuck in a bunker with some of the nosiest people to grace this planet. Kinda came with the territory, when it was literally part of the job description to get all up in people’s business. 

---

Your walk to the gun range was unfortuately stupidly short. And before you could even fully put up your defenses to protect your heart, you were inside the large concrete chamber. Eyes locked on the closest booth, you refused to look back at Dean behind you. Flinching slightly as the metallic sound of the lock clicking into place behind you signified that Dean effectively had you trapped. 

“So… Where do you want me for the firing squad? Actually, I haven’t even had breakfast. I deserve a last meal, maybe skittles and pancakes? Oh and…” Your voice was slightly higher pitched than you wanted it to be as you took a few steps towards the closest booth, before just as quickly being pulled back by Dean and gently turned to face his forest fire eyes. 

“Can you be serious for five minutes (Y/N)?” Dean’s frustrated sigh was softer than you expected. After all, you were a master at pissing people off. Lifting his other hand, he held onto both your upper arms, locking you in place as you let your eyes focus on the locked door behind him. 

“My record is two, and three quarters. But hey, I can try?” Your quip came out shaky and weak as you tried to form a breathless laugh and thoroughly failed. With Dean this close, holding onto your bare arms with a soft grip as his thumbs painted small circles on the sensitive skin, you barely had enough breath left to even form the words themselves. 

“Why are you running away from me and hiding in your room like some kinda criminal?” Dean pushed, ignoring your attempt at humor with a tired groan as he slightly nudged you. Forcing you to look up into his eyes and seeing the tired tint to them. There was something there… Something nearly… Fragile. But you couldn’t let yourself linger on it. 

After all, he was probably just saddened that he had to do this at all. Dean’s heart was too big. Though he usually pretended he didn’t have one. You knew he did. Dean Winchester loved, more fiercely and passionately than anyone else you knew. Though it was all familial love. 

He was just worried. 

Yeah… That was all. He was worried about a member of his team. His family. 

“I mean, technically we’re all criminals…” Your words trailed out into nothing, echoing against the concrete walls around you as you let your eyes drop to not see the tired tinge in green eyes. Focusing instead on your own fidgeting hands as you waited for him to finally get to the point. 

“Stop being a goddamn coward. And. Look. At. Me. (Y/N),” Dean growled. The earlier exhaustion gone, and replaced with anger and frustration as one hand dropped from your arm to lift your chin with surprising softness that didn’t match the barely restrained anger in his tone. 

Anger was better… You could deal with anger. You could respond to anger. 

Squaring your jaw, you let your own (Y/E/C) eyes burn into Dean’s as your shoulders tensed and hands curled into fists. 

“Look, I'm not gonna stand here and listen to you accuse me of things I clearly did,” You spat back, trying to shake off his hold on you to head for the door. But Dean wasn’t having it, as his hands stayed firmly in place. Stopping you from storming off. 

“(Y/N)!” Dean’s booming voice echoed around the room like a gunshot as you slightly flinched from the sudden increase in volume. Not out of fear… No, you knew Dean. No matter how much he was about to hurt you with his words, he would never hurt you willingly. Hell, if he knew how much it would hurt you to hear him shrug off the almost kiss, it would haunt him. No, your microscopic flinch was born solely out of surprise. Yet, Dean’s voice still lowered automatically as he continued speaking through gritted teeth. 

“Will you stop running away from just one goddamn second?” Pushing the words out at a much lower volume, Dean walked you, backwards, further into the gun range, until your back was nearly against the wall. As if he feared the proximity to the door would leave you an opening to actually run away. 

“I’m not running, I’m right here,” You squeaked out. Though breathless and weak from his hands on you, you refused to fully back down. 

“I mean with your constant jokes and weak attempts at changing the topic,” Dean clarified, though he knew, as well as you, that the clarification wasn’t needed. It was kind of your whole brand. 

Wetting your lips, you glanced towards his full ones, feeling liquid shots of heat rushing through your body from the way they were slightly parted as short, angry breaths left the hitter. 

Fuck. 

Forcing yourself to look away from the same lips that were the main culprit in this whole mess, you swallowed hard. Lips parted as you tried to make your brain work again. Though words failed you as your eyes instead landed on Dean’s body when you attempted to avoid his green eyes.

There was no way you could find any arguments to shoot back… Not when you were momentarily hypnotized by the way his chest was falling and rising from the sharp breaths he was taking. Or the way his muscles moved fluidly under the slightly tight cotton t-shirt. Damn whoever made that t-shirt. You simultaneously wanted to kick their ass and send them a thank you letter and fucking fruit basket. 

Taking a shaky breath you let your teeth graze your bottom lip, pulling on it as you tried to form the words. Hell, maybe you should tell him it was nothing? Break your own heart before he could? That would show him. But no… When he was so damn close, leaving barely any space between the two of you, there was no way you could fool him. He had to see what he did to you.

“I just…” You started, not sure what argument you were preparing to throw back at him, as your mind was still a jumbled mess from his proximity. But you never got to figure out whatever defenses your brain had concocted. 

Since, before you could finish up your argument, you were interrupted by Dean’s frustrated groan as he pushed you against the concrete wall he’d walked you towards. His body pressed up against yours. Holding you in place as one knee moved between your weak legs and calloused hands finally dropped yours only for toned arms to cage you in against the wall. 

The words died in your throat, whatever they were, as you looked wide eyed up into burning eyes. For a second, the world stood still as your brain reeled from the feel of his body, molding against yours. But Dean didn’t move, he kept you locked in place as he looked down at you, green eyes focused on your lips as he wet his own. His sharp breaths fanning over your face as you subconsciously mirrored his gesture, a flash of pink wetting your own lips. 

Stopping yourself, you parted your lips to say… Fuck, you didn’t know… Something. Anything. But before you could, Dean beat you to it. 

“Just shut up (Y/L/N),” He growled, effectively cutting off your words before leaning in for a bruising kiss. 

It took no more than a split second for your brain to realize what was happening, as you made your lips pliable. Kissing him back as your hands lifted, snaking around his neck and digging into his soft hair. Pulling slightly on the strands, you hummed victoriously as you teased a small groan out of the mercenary, making him part his lips just enough for you to deepen the kiss. 

Dean ground his body against yours as he took your breath away, filling your mind and senses with nothing but him, nothing but his kiss. Pearly white teeth nipped at your bottom lip, teasing a little whimper out of you as he smiled against your lips, unwilling to break the kiss. Damn it… 

Dean wasn’t just kissing you. He was devouring you. 

The hands that had caged you against the wall were once more on your body, traveling the length of your torso. Stopping to massage your hips before once more moving up your body and pulling you, if possible, even closer as he groaned against your lips. 

Your hips rolled against his as you kissed him back with a desperation that surprised even you. Your heart was doing it’s damndest to beat out of your chest as you savored the taste of him. All spiced peppermint and liquid fire. 

You didn’t know how long you’d been trapped in his arms, lost in his kiss, but once he finally leaned back, sucking in a sharp breath, you wanted nothing more than to feel his lips on yours again. Nothing else mattered as you tried to chase his lips as if you were chasing a high. 

“Damn it woman, you’re infuriating,” Dean groaned as he struggled to catch his breath. His body still against you, all hard and demanding as he pushed his thigh against your core, teasing more whimpers out of you as your body rolled against it on its own volition. 

“You’re no better Winchester,” Your quip back was swallowed by his mouth on yours again as your fingers tugged on the short strands of his hair. With a pleased little sigh, you conceded, letting him easily take control while you drowned in the feel and taste of him. 

“Fuck (Y/N), having you pushed against me in that damn closet. You don’t know…” Dean growled against your lips. Cutting off his own words as his tongue traced your bottom lip before deepening the kiss again. 

You could do nothing but hold on for dear life. Your heart was in your throat, drowning out the rest of the world. There was nothing else. Just Dean Winchester. The feel of his hard body, shaping against yours as he turned you into this willing, needy little thing. His to control and do with as he pleased 

Feeling Dean remove his thigh from where it was pushed up against your core, you whimpered at the loss. Not caring at how wanton the noise made you sound as you rolled your hips against nothing, trying to find friction again. Yet, his strong hands kept you in place, trailing down your body before landing in a bruising hold on your hips.

You could feel him smirk against your lips. Enjoying the reactions he was teasing out of you and the sound of your little indignant whimpers leaving you from not letting you roll against him. 

“Patience,” He hummed as his thumb carved their mark into your still rolling hips before trailing around you. For a second, his big palms just rested on your ass as he tugged your lip between his teeth before soothing it with the tip of his tongue. 

“Dean,” You didn’t care that you sounded needy and breathless as you nearly pouted at the hitter. Your body was all fire and desperation, and only Dean Winchester could quench it. But he was holding back, punishing you for your earlier escape attempts now that you were his to play with. 

With another soft hum, Dean placed a much more chaste kiss on your lips, before squeezing your ass and swallowing the soft whimper that left you with his mouth on yours. 

Needing no more prompting, you lifted yourself up and wrapped your legs around his hips. Moaning into the kiss as you felt his obvious arousal through his gym shorts, pushing against you. With Dean and the wall holding you up, you could only roll your hips and let your nails trail against his neck as you drowned in the taste of him. You were weightless, breathless, and… 

Damn it. 

Your dirty daydreams were nowhere fucking close to the actual out of body experience that was Dean Winchester. The actual man was all that, and so much more. You might have been proud of your imagination, but not even your wildest dreams could live up to the way he set every damn nerve on your body on fire. You were unraveling, falling apart, trapped between concrete and Dean’s hard body. 

And all the man had done was fucking kiss you.

Breaking the kiss, Dean’s head dipped as you leaned your head back against the wall. Giving him easy access as his tongue trailed town your throat. Feeling the vibrations of the breathless whimpers trapped there as he hummed in approval. And you felt proud, proud that he was happy with you, that you were pleasing him, at least from the feel of him as he pushed against you. The thin gym shorts leaving little to the imagination. 

Placing small kisses against your pulse point, he let his teeth graze against your collarbone before just as quickly chasing the high of your lips again as he captured your lips in another dizzying kiss. And damn it, you needed that high. You needed to taste him. 

Yet, before you could fully fall back into the kiss, you were left wanting… As you were interrupted by Sam… Again. 

Damn him and his hair products to the deepest levels of hell. 

“Guys, there’s trouble. Come to the War Room. Now…” The urgency in Sam’s voice across the Bunker’s intercom system lessened your anger towards the youngest Winchester. But only a little bit. The teensiest tiniest bit. As you looked wide eyed at Dean. Your fingers untangling from his hair as you raised an eyebrow, wondering what the fuck could have gone wrong now. When you were nearly at the homestretch of the job. 

But Dean’s eyes didn’t meet yours. Still focused on your lips, he let his tongue roll against his bottom lip, as if engraving the taste of you there, before his head fell against your shoulder with a defeated sigh. 

His body had stilled, no longer rolling against you, but he still held you up, trapped between his body and the wall as he tried to control his ragged breaths. Silent curses fanned against your heated skin as his arms tightened around you for a second. 

Finally in control, Dean lifted his head just a fraction, to let his teeth graze against your pulse, before reluctantly stepping back from the wall and letting you back down. Though his arms were still securely around you as his hands massaged your ass, pushing you up against his body. His hot breath fanned over the sensitive skin of your neck as he cursed Sam once more. 

“Damn it Sammy,” His voice was cracked and breathless as he finally pulled himself away from you. Adjusting his shorts and throwing you a little smirk as you let a trembling hand lift to cool heated your cheeks before trying to fix your own clothes and hide any hints of the explosive makeout session you’d just gotten yourself into. 

Though you doubted you could hide it. Shit, if Dean’s own slightly mussed hair and kiss swollen lips were anything to go by, you probably looked freshly fucked. 

Oh joy… This would be a great conversation starter around the War Room table. 

You could picture it; “Sorry I’m late Sammy, your brother was just busy taking me apart piece by piece with his tongue in the gun range”. 

Yeah… No thanks. 

Yet, from Sam’s urgent tone over the intercom. You knew you didn’t have time to get that cold shower your body was nearly begging you to have. Something was wrong, and the ice cold dread that thought sent through your body once the proximity of Dean was no longer muddling your brain, would have to stand in for the shower you needed. 

And as Dean’s teasing smile fell away, letting the professional hitter once more take over, you knew he’d reached the same conclusion. Your crew needed you. That was all that mattered.

---

Ok… So maybe you weren’t the best at rushing. 

But even though you looked like you’d just been… Well, making out with a damned greek god in the gun range, you didn’t really feel the need to advertise it to the whole damn crew. So, while Dean headed straight to the War Room, you stopped by the kitchen for some much needed water. 

If nothing else, just to make sure you didn’t arrive at the War Table at the exact same time as the dangerously addictive hitter. Though, truth be told, you needed the water. You were parched. Taking a sip of the ice cold bottle and lifting it to your cheek to cool down, you took a few deep breaths as you tried your best to smooth down your messy hair.

Hell, maybe they’d just think you’d been working out? After all, you kinda had been. Just a much more fun form of working out. If you could somehow bottle up the pure lighting to your nerves that was Dean Winchester and sell it, you’d be a fucking millionaire. 

Actually, you already kinda were a millionaire. If you counted your hidden stash of goodies from before you started stealing for the good guys. But hey… That didn’t count. 

As you walked into the War Room, you threw a grin towards Charlie, pretending you couldn’t feel Dean’s green eyes burning into you as you instead focused on Sam’s serious, set face. Sending an apologetic smile his way before you quickly stepped over to your seat and sank into your chair. 

“Now that everyone is here…” Sam said, clearing his throat as he threw you a look. The raised eyebrow showing that your current slightly unraveled appearance hadn’t escaped his trained eye. And by the way Charlie’s eyes were focused on you with an amused smirk, you knew she hadn’t either. Damn it.

“Sorry guys… Gym, needed some water before I came,” You still squeaked out, fooling absolutely no one. Though you doubted the way Dean’s eyes wouldn’t leave you, with him looking just as deliciously disheveled as you in the seat to your right, helped in any way either. 

“Sure… As I was saying before you decided to finally join us (Y/N). There’s trouble,” Sam continued, clearly deciding to drop the subject in favor of more pressing matters. Though you knew you’d have to deal with the Kid Wonder tag team of Sam and Charlie after the mess was cleared up either way. 

“What happened? Did they notice you trying to access their files?” Dean shot in, taking some of the heat off of you as he finally moved his eyes to focus on his brother. That steely, all-business look that made you weak in the knees back in green eyes as he leaned in.

From across the table, Charlie scoffed, sounding straight up offended as she leaned back in her seat, crossing her arms over her torso as she shot Dean a dirty look. 

“No way!” Her indignant voice shot in. After all, Charlie was the best. And she took pride in her work. There was no way anyone would notice it if she decided to take a gander at their files. If it was connected to the internet, Charlie could access it. Which was also why you kept all your secrets safely in hard copies, and barely even dared to watch the wrong thing on Netflix. Just in case Charlie would read something into it. 

“What’s up? It sounded serious,” You shot in, not wanting Charlie to derail the briefing by telling all of you, in excruciating detail, exactly how perfect her hacking skills were. You’d listened to those rants before. And though you didn’t even understand a fraction of what she’d talked about. You knew you could trust her skills. If she said it wasn’t the hacking, then something else had gone wrong. And you’d be willing to bet your fortune on it not being anything any of your brilliant crew had done wrong. 

You were the best. And though you were dealing with some very bad guys. It was a pretty standard job. So there was no way your criminal Scooby Gang had messed anything up. 

“They got Crowley,” Sam said with a tired sigh. 

Bingo. 

Of course it was the weak link in your operation that messed things up again. Damn it, that’s why none of you liked working with outsiders. They always messed everything up. 

“What do you mean they got him?” Dean pushed, the tired strain to his voice telling you he knew exactly what his brother meant as he pinched the bridge of his nose. Though he still asked. Just in case your own resident mobster decided to surprise you for once

“You know how I keep everyone we work with under surveillance?” Sam asked no one in particular, not even really waiting for the small nods from the group as he carded a big hand through his brown hair in a mix of anger and frustration before he kept speaking. 

“Earlier today, a bunch of goons got a hold of Crowley when he was leaving his tailor. They’re keeping him in one of the empty buildings they own,” He continued, before pausing to look around the room at all of you, letting his words sink in as you tensed in your seat. 

If Crowley was caught, it put your whole damn operation in danger. Even if the bastard didn’t squeal, the big bads would be on guard now… Plus, there was that little extra item added to your to do list of having to go save the Scotsman. Even if you really, really, didn’t feel like it.

Fuck.

Or… As your dearest boss so eloquently put it once the speaker in the middle of the table crackled to life. 

“Balls,” 

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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

Rushing into your room, you locked the door and pushed a chair up against it for extra measure. Sure, you were a coward. But you were a thorough coward. And you wouldn’t put it past the stubborn older Winchester to kick your door down to stop you from running away from the conversation he seemed hell bent on having. 

Shit, you running away was probably just making him more set on having ‘The Talk’. 

After all, Dean Winchester was a hitter with an impressive resume; a trained soldier, tracker, and mercenary… He was the epitome of a hunter - a true predator. And your ‘scared little prey’-act was probably just activating some long-lost hunting instinct in the man. Like an enticing game of cat and mouse.

Actually, you were sure of it. 

The way those emerald eyes had been burning into you; like he was ready to devour you on the spot… Yeah, that was the look of an Apex Predator. Even now, in the safety of your own room, the feel of Dean’s eyes on you still ignited a fire in your veins. 

Hell, you swore you could still feel the whispers of his touch where he’d brushed against you. And the smell of his body wash still lingered around you, making your mind a foggy, hazy mess as you struggled to catch your breath even though the short sprint to your room shouldn’t have made you that breathless. Not with the hellish training regimen the Winchester brothers had you on.

Damn it... There was only one thing that could help you now: a cold shower. Absolutely arctic. The coldest shower to ever fucking shower. Yeah… That would teach your libido to act up without consulting the more reasonable part of your brain first. 

Peeling off your clothes, you hurried to your attached bathroom, feeling uncomfortably hot even in the chilly air of the bunker room. Throwing one last wary glance towards the chair you’d propped up as a last line of defense, you closed the bathroom door with a groan. Letting your head hit against the wood with a sigh. 

Forcing your eyes to focus on the shower, you ignored the clown in the mirror, aka. your own bitch ass self. Knowing you’d probably end up having a damn Taxi-esque “Are you talking to me” monologue with your reflection if you allowed yourself to spare the woman in the mirror even the smallest glance. And, though you did deserve a talking to, you just didn’t have the energy to admonish yourself any further. 

Plus, you were as naked as the day you were born. Meaning that any dressing down you gave yourself would be kind of useless. 

So, instead you stepped into the dry shower and gritted your teeth as you turned the water on. Turning the knob ALL the way to cold. No fucking way you were having a hot shower. First, your already overheated body wouldn’t be able to handle the heat. And second, you didn’t deserve one. Hell, you didn’t even deserve the much more tolerable shock of stepping gingerly under the running water and preparing yourself for the shock of icy cold against flushed skin.

Gritting your teeth against the need to squeal as the first chilly drops hit your overheated skin, you closed your eyes and let the water cascade over you. Letting it wash your cowardice and dirty thoughts down the drain. The feel of Dean’s body heat where he’d brushed against your arm and his much larger hand on yours was slowly being replaced by the numbing feeling of cold water on hot skin as your nerves went into temporary shock. Though the frozen state of your nerves did nothing to stop your mind from racing.

You’d known from the start that you shouldn’t allow yourself to indulge in thoughts of the oldest Winchester brother. 

Sure, it had been clear from day one that you found the man devastatingly handsome; even when you still thought he could be a threat to your safety. But, once you moved into the bunker with the Winchesters, you’d also known you weren’t good enough for him. 

Hell, you were a lot of things. But one thing was certain. You, (Y/N) (Y/L/N), were not even remotely good, full stop. 

Having been raised to steal, spy, destroy, and do everything else your bosses told you to do had beaten any sense of morality out of you a long, long time ago. From a young age, your moral compass had been thoroughly ground to dust under the heavy heel of the “organization”. And, until you met Dean, you’d been sure it had beaten any shred of that annoying human emotion known as love out of you too. After all, in the underground organization you’d called home for a better part of your life, any form of feelings was considered a weakness.

Love, fear, even hate… None of that was relevant or even necessary there. 

All that mattered was to complete your tasks, please the client and get paid. It was the code you’d been raised to live by. It was what your area’s boss, a witch of a woman nicknamed “Dr. Hess”, wanted. 

Her and the other area mobster bosses, including the man at the very top, had stolen you from your parents when you were still just a baby and sharpened you into a weapon. You and countless other children. An army of kids and teens who did their bidding, no matter how vicious and evil it was. 

And you’d done it all. After all, you knew nothing else.

The organization had been worldwide, but your world had still been so very, very small. On the leash of your handler, Mr. Ketch, you’d only ever been let out of one of their underground compounds to complete whatever job they had for you. Whenever they needed a pair of extra sticky hands, you’d get let out, only to be pulled right back in when you’d done what they wanted you to. 

You’d only managed to escape when you took out two of the guard dogs they’d placed to watch you on a job in Lisbon. And even then, it was only because they’d been resting on their laurels. 

Mr. Ketch had been out on another job. And since you’d spent the better part of your early teens fooling them into thinking you’d finally become a good little puppy who could go without a leash for 24 hours, they’d placed the role of guardians in… Less capable hands.  

Wounding, possibly mortally, those two men… You hadn’t felt a thing.

If anything, you’d felt a hint of elation. Joy at finally being free. 

That’s how you knew you weren’t human. You weren’t fit for love. All you had, the only thing you were fit for, was your life as a thief. Hell, your freedom was less about escaping the life of crime you’d been forced into and more about escaping the authority figures that took all your hard-earned spoils for themselves while keeping you locked in your cage. After all, you’d worked for that money. They hadn’t.

Sighing you gritted your teeth and opened your eyes to stare reproachingly at the jet of icy water still cascading down over you. The cold water had cooled your head, sure. But it had also brought back memories of days you’d do anything to forget. Even though they were tattooed onto your very being, clinging to the back of your mind. with vicious talons made up of scar tissue and regret

Days of hiding scraps so you could eat them if they decided to cut off your food supply. Of tearing bedsheets into bandages after an especially grueling “training session”. Days that were carved into your bones through a childhood that was more torture, training and prison bars than nostalgic picket fences and apple pie. 

Turning off the water, you shook your wet (Y/H/C) hair out behind your back before reaching for the towel. Your body was shivering, but you didn’t mind the cold. The cold was… Comforting. It was a physical manifestation of what you constantly had to remind yourself to be.

The cold was your code to live by. Not the organization’s.

Hide behind jokes, use your smile as a shield and your boisterous volume as ammunition. Drown out your darker thoughts with endless internal color commentary going a mile a minute… Don’t ever get close enough for anyone to see it’s all just painted on. A fake facade; a prop mask in a low budget movie. Laugh loud, be loud, hide any stray hurt, or old memories, behind surface level hollow strength and sass. 

Don’t let them see you cry. Never let them see you hurt. 

Even though you did have friends now; a family... You had Charlie, who you adored, a father figure in Bobby, and Sam, who you saw as your giant little brother. You still kept your walls up. Though your smiles were more honest, and your feelings had a place to safely rest in Charlie who never let you joke about your pain, you couldn’t fool yourself into thinking you could have anything more than that. 

You couldn’t fool yourself into thinking you deserved a place by Dean’s side.

You’d already been handed more than you ever deserved when Bobby Singer and the Winchester brothers accepted you into their family. You’d gained trust you didn’t even have in yourself, and there was no way you’d repay them by breaking apart the dynamic that worked like a well-oiled machine. 

Which was why you knew you’d have to just grin and bear it when Dean broke your heart. You couldn’t leave them just to run from the heartbreak. You had nowhere else to go. This was your home. The only one you’d ever truly had. 

Still, you just needed a little more time. Just a few more hours. 

The universe could at least give you that much as payment for being the butt of every karmic joke it threw your way.

Right?

---

Your prayer to the universe for a few more hours of silent, contemplative cowardice was left on read. As mother nature once more seemed ready to get her rocks off by watching you squirm. 

The sadistic bitch. 

You were barely given time to get dressed, not to mention warm up, before you heard the quick, sharp tap of knuckles against wood. The sound of someone knocking on your door was enough to make you freeze where you stood in the middle of your room. But as the deep voice of a certain Mr. Winchester seeped through the wood and straight into your veins, you slowly morphed into an actual statue; holding your breath as you worried that the man on the other side of the door would somehow hear you if you as much as blinked.  

“Hey (Y/N)... You still up?” 

You kept holding your breath, your eyes jumping to the chair you’d propped against the door as you slowly sank to the floor. Sitting down as softly and carefully as you could. Mainly as a preemptive measure, in case your legs would give out under you if he decided to break your heart through the door instead.

“Of course you are… You’re just… Look, kid. I know you’re in there,” The soft thud against the wood that punctuated his words painted a picture of Dean leaning up against your door. And though you had no way of seeing him, you could almost picture him bringing one of those large hands up to pinch at the bridge of his nose or draw it over his face. Like he always did whenever you frustrated him.

Which was often. 

You were nothing if not frustrating to be around. 

“Son of a... Can you stop running away for just one second? We need to talk. Open up the door sweetheart… Please,” Dean’s words were soft and inviting, but you couldn’t… There was no way you could make yourself open the door and face him; face having your heart broken. Not when you were dressed in superman shorts and a ratty t-shirt while still shivering from the cold shower.  

So, you kept still; only allowing yourself a small intake of air before you held your breath again. Shifting slightly, you hugged your knees to your chest where you sat. In some foolish attempt to protect your fragile heart from the man who unwittingly already held it in his hands by folding in on yourself and using your body to protect the weak, cowardly muscle in your chest. 

On the other side of the door, Dean waited for a beat, then another. Still somehow holding out hope that you’d grow a pair and face him. Though he should have known you better by now. 

“You can’t run away from me forever (Y/N),” The typical movie villain phrase sounded both seductive and dangerous when leaving the seasoned soldier. Though, in fairness, with your style of flirting; danger and seduction were pretty much synonymous. 

And though the little daredevil on your shoulder wanted to respond to the challenge in Dean’s words, you bit your tongue. Even though you had a pre-written list of comebacks prepared for people questioning your ability to run away from your problems (number one on the list being simply that you were very fast) you couldn’t put it to good use. Not without ending up having ‘The Talk’ you’d been dreading through your closed and locked door. 

In fucking Superman shorts.

So, instead of bragging about your straight up cartoonish roadrunner speed, you kept silent. Listening, but not fully catching Dean’s tired, groaned mutterings from the other side of your door as your team’s hitter seemed to realize you weren’t going to respond no matter what he said. Choosing instead to tap his knuckles against the wood again with a tired sigh. 

“Damn it sweetheart, you’re infuriating,” Dean’s tired voice was followed by another quick tap against your door. Before you heard the unmistakable sound of his bare feet walking away, down the hall towards his own room. 

It was only once you heard the muted sound of a door closing somewhere further down the hall that you let yourself breathe easy again. Your body was aching from the frozen hold of your muscles as you finally clambered to your feet again and shakily made your way over to your bed. You doubted you’d be able to sleep. But, hell, you needed to be horizontal to deal with the tidal wave of fears and emotions that were threatening to drown you. 

You were the biggest coward to ever coward. And you hated yourself for it. You were a big girl, yet you couldn’t woman up enough to just… Talk to Dean. You knew you had to. Hell, you were ruining the first good thing you’d ever managed to build for yourself. 

If you kept running like this, you’d soon literally be on the run again. And Dean wouldn’t just… Not like you. He’d most likely end up despising you. You’d seen those forest green eyes turn steely with hate and anger before. Towards people outside of your little band of thieves. But the idea of having them focused on you that way? Burning in that ice cold way frostbite does, as he stared you down with nothing but hate and fury in his eyes?

Fuck. 

If only there was a way to turn off your feelings for the former mercenary. Like how you’d managed to trick yourself into thinking you weren’t still haunted by nightmares of your not-so-pleasant childhood. But no… 

You’d already tried that when you first realized that how you felt about him went beyond just physical attraction. It was no use. Dean Winchester was all-encompassing. All you could do was smile, pretend it didn’t hurt to be “just a part of the family” and drown yourself in daydreams, both dirty and innocent ones. 

Maybe if you played the part of class clown and younger sister well enough, you’d be able to stay at the bunker. But… Would you even want to? Would you be able to bear it? Then again, you doubted you’d be able to bear the loss of the first family you’d ever found for yourself either… Your family. Sighing, you squeezed your eyes shut and ground your teeth together to not scream in frustration. 

You were just running in circles. There was no way out. No plan B. 

For once there was no easy escape route for you to rappel your way down and away from danger. There was no neatly stacked and expertly highlighted “What to do if (Y/N) fucks up majorly”-manila folder that you could refer to. You had to make a choice, either way you were losing something. If you ran, you had to run away from everything that you’d found. From the family that made you happy for the first time in your life. But if you stayed… Damn it. 

You couldn’t have your cake and eat it too.

Actually, no. Fuck that.

You refused to use that saying. You wanted to punch the first person to mention cake in such a dirty context. ‘Cause cake was way too tasty to ever be spoken about in a situation like the one you found yourself in. 

Damn it all to hell.. Now you were frustrated, angry, sad and you wanted cake. Yeah, you’d punch whichever twisted bastard that created the phrase in a heartbeat. You’d punch him good.

Then you’d get two cakes to celebrate, one to eat and one to just… Have. Because fuck that saying. 

Not that it helped the situation you were in, but hell... Nothing would. Not even cake. You were doomed to spend your night lying awake and counting down the minutes until Dean found you and broke your heart. The only thing you could do was prepare yourself for the blow. Get ready to roll with the punches, smile through the pain, and cover up any bruises to your heart with bad jokes and even worse decisions. 

That, and allow yourself just this one night to think about the kiss you almost shared with the oldest Winchester brother. After that one night, you’d have to erase it from your memory. It would just hurt too much to remember what you’d been so close to tasting, yet could never have.

Taking a shaky breath, you let your tongue wet your lips as you slipped easily back into the memory of the closet. You knew you shouldn’t, that it would just end up hurting you. Yet, it was almost too easy. The feel of Dean’s body against yours was still so clear in your memory. It almost felt like you were truly back there. If only Sam hadn’t spoken up when he did…

Letting your imagination take over, you rewrote the memory in your mind. You were back in the closet, but with no interruptions to save you from Dean’s hungry look and teasing grin. 

His body was hard against yours. The arms that had pulled you so dangerously close were roaming the curves of your body, massaging your hips as you rolled against him. Feeling that same mouth watering bulge that had almost made you whimper back in the closet push against you again in your memory. Swallowing a similar whimper, you let your hand travel the length of your body back in your bunker bed. Letting your inpatient, trembling fingers emulate the many overwhelming feelings from just hours earlier. 

The look in his eyes, that domineering, in-control look, had you biting your lip to keep from gasping as you relived every second. How he’d let his teeth graze against his plump bottom lip, before letting his tongue soothe their path as he slowly, painfully so, lowered his head until his lips nearly touched yours. And this time, in your daydreams, his lips landed on yours, stealing your breath away. All fire and spice and everything naughty as he swallowed your gasps of air and nibbled on your bottom lip when you made even the slightest sound. 

At that moment, all your dirtiest daydreams came true. His rough breath as he nearly growled against your lips. And the feel of his body against yours, calloused fingers shaping the curve of you against him as he greedily swallowed every little sound you dared to make to keep you quiet, to stop the mobsters outside from finding you... 

At least for a second. 

Before, just as it had in real life, your damned imaginary closet kiss was also interrupted. This time, not by Sam’s voice in your ear, but rather yet another knock on the door that made you stiffen on your bed. Your fingers quickly pulled back as if burned by the hem of your shorts where you’d been playing with the thought of taking your daydreams to the next base.

Once again you were left unable to move a muscle. And, with your body, now heating up but still aching from your earlier involuntary game of freeze tag, every muscle nearly screamed in protest from the sudden tense hold. 

Was it Dean again?

Holding your breath, you waited to hear that same intoxicatingly deep voice on the other side of the door that had frozen you in place not all that long ago. Had he changed his mind and decided to break your heart through the door after all? But, whomever was knocking on your door kept silent this time. Choosing to knock again instead of announcing themselves. 

Maybe Dean was trying to trick you to come outside and see who it was? Or maybe it was someone else? 

Damn it… You needed to know who it was. Even if it was safer to just stay in bed and drown in your daydreams. You and your curious mind demanded answers, even if you were likely to regret going in search of them. As the saying went: Curiosity killed the cat…burglar. Curiosity killed the cat burglar. And, in this specific situation, you were the sneaky feline thief in question. 

Moving slowly, to ensure the bed didn’t creak and give you away, you slid off of the sheets, before tiptoeing over to the closed door like a typical cartoon bandit. Leaning in, careful to not knock into the chair still blocking the door, you pushed the shell of your ear against the wood. Listening for any hints that could tell you who was outside. 

An overall futile and foolish act altogether. Since, only seconds after you started your cowardly sleuthing, your new guests finally spoke up behind door numero uno. 

“It’s me (Y/N) and you’re not as sneaky as you think. I could hear you tiptoeing over and leaning against your door… These rooms aren’t exactly soundproof. Remember? Open up,” Charlie’s voice was a welcome sound as you sighed in relief. 

Shaking away the rest of the stiff hold in your limbs, you quickly moved the chair out of the way. Stopping with your hand on the lock to listen for the sound of anyone else in the hallway before unlocking the door. Casting a wary glance down the hallway, you just as hurriedly ushered your best friend into your room and closed your one line of defense against Dean again.

“Could you really hear me?” You stage whispered as soon as the lock was securely latched.  Opting to not prop the chair back in its place to save yourself from even more questioning looks from your best friend as you turned to face her. Fearing that Dean would have also heard your attempts at being silent through the door earlier.

“No… But I know you,” Charlie sighed, crossing her arms in front of her chest as she rolled her eyes at you. A look she’d always been a champ at, but had fully perfected after learning the tricks of the trade from the master of the bitch face; one Mr. Sam Winchester. 

“What’s up with you anyway? Why are you sneaking around like a… Well, like a thief on the run, which… Sure, you are. But not here. Not at home,“ She added, her green eyes narrowing as she tried to get a read on you.  

“A girl can never be too careful you know,” You cringed internally at the slightly elevated pitch to your voice as Charlie eyed you suspiciously, not falling for your weak reasoning and poor acting skills. Thank God your team had an actual grifter on board, because with your lacking skills it was a wonder you’d ever been able to go undercover at all before Cas joined your crew. 

Yet, your best friend mercifully didn’t just decide to decimate your weak acting and force the truth out of you. At least not right away. Choosing instead to go with the slow torture method. Which was usually much less her style than it was yours.

“We live in an underground bunker… With a team of the best mercenaries, hackers and con artists on the planet. Who’d be stupid enough to try and break in here?” Charlie challenged with another roll of green eyes as she strode across your room before plopping down on your bed. 

“I can think of a few of our enemies who’d like to try. Especially a few of mine,” You squeaked back. Knowing full well they were all currently locked up behind bars. At least the ones that had any notion about where in the big wide world you were. Your personal enemies were still, unfortunately, roaming free. But they also thought you were somewhere in Italy, last you heard. 

“I’d like to see them try. Well… Actually, I wouldn’t, but you know Dean or Sam would kick their asses before they even got near this part of the bunker,” Charlie shot back as she lounged on your bed and picked up one of the hardcover Batman comic books you’d borrowed from her stash with a raised eyebrow, before just as easily letting it go against your weak shoulder shrug considering she’d given you a free pass to her collection. 

Though, she was clearly not as ready to let go of your latest bout of weird behavior. Since her dropping one issue, of the comic book variety, only meant she was instead choosing to go in for the kill on the big one. The reason she’d come knocking at your door in the first place. 

“But seriously… What’s wrong? I mean, I know I’m not always the best at noticing social cues. But you keep running away from Dean like you stole the last slice of pie,” She sighed instead, leafing through the issue of The Long Halloween, though her eyes were still locked on you where you were standing awkwardly in the middle of the room. 

“That was you…” Your weak comeback lacked your usual creative sass as you trudged back to your bed and sank down next to Charlie.

“Don’t change the subject,” Your best friend admonished as she scooted over to make more room for you. Keeping the comic book out of your reach when you tried to grab it from her to hide your shifty eyes and messy feelings behind the safe, broad back of Batman. 

“Then don’t steal a man’s pie next time,” You shot back with a huff as you gave up on the comic book and instead chose to grab for your pillow. Holding the soft memory foam pillow close, you shifted on the bed until your back hit the wall and half curled in on yourself. Like the petulant child you were currently acting like. 

“… Do I have to go ask Dean instead? ‘Cause I will. Don’t try me,” Charlie challenged, putting the book down and twisting her body to fully face you. 

“You don’t have the balls to. I’ll tell him you’re the one that took the last slice of pie,” Not being one to let any challenge pass you by, you shot back with your own. 

Though you knew you really shouldn’t be challenging your stubborn best friend. Not about that. Not when the wellbeing of your heart was on the line and the pie issue was a whole week old. Many pies had come and gone since the theft of that one, but your own little ‘issue’ was still fresh out of the oven.

“As I said… Try me,” Was all Charlie deemed necessary to say as she cocked an eyebrow at you before trying to wrestle the pillow you were now half hiding behind out of your iron grip. Which thoroughly failed. There was no way you were giving up your lifeline/pillow when it was all you had left to hide behind. 

“Try you? Try me,” Your words came out muffled from behind the pillow, and your eyes were looking everywhere but towards your best friend. Not your best challenge. But hell, if you looked her dead in the eye you had a feeling Charlie would just know everything. Sometimes you were sure she was actually Professor X in disguise with her uncanny ability to read your mind. 

Unfortunately, just as you feared. You really shouldn’t have challenged your stubborn best friend. 

Especially not when she was already painfully aware that something had gone down and that you were actively running away from Dean. She knew how you felt about him, and she also knew you were a self-sabotaging dumbass. So of course she’d rise to any challenge you put forward. 

Which meant... With an over dramatic deep breath for added effect, Charlie said to hell with ‘indoor voices’ as she raised her own voice just a fraction. Though even a fraction could be too much in the bunker, where sound traveled faster and farther than what should be physically possible.

“Hey! De…!”

“Shhhh-ut your trap!” You whisper-yelled at the red head as you dropped the pillow to try and reach out for her in a weak attempt to silence the hacker. An attempt that failed, as she decided to become ninja fast at that exact moment and jump out of your way. 

“Make me,” Charlie shot back, her voice back at normal indoor voice levels, as she stood next to your bed. Her arms once more crossed and an eyebrow raised in a silent challenge. You both knew she’d be able to call for Dean before you even had a chance of reaching her. It was futile. 

“Damn it… Ok. Sleepover?“ You sighed, finally conceding to your best friend. The only person you almost constantly lost any fight against. She knew too many of your weaknesses. And trying to win against her in a battle of wits was near impossible. She’d make for one hell of a final boss if she decided to turn bad on you one day.

“Only if you let me give you Princess Leia buns,” Charlie quipped back, wanting more now that you’d already made one concession and she knew she’d won the war. The spoils of the war were always decided by the victor afterall. 

“…Alright, geek,”You rolled your eyes with a fond smile as you slowly got up from your bed, with your arms held up in surrender. Shaking out your weak legs, you took the few steps across the small room to walk Charlie to the door, knowing she’d still need to get her stuff before any slumber party or hair braiding could happen. 

“Go get your stuff, and pick up some beers… Scratch that, grab the whiskey. The good one. Don’t let anyone see you. And when you come back… You know the deal?” You let your voice drop to a conspiratorial whisper again as your hand rested on the lock. Not willing to unlock it for more than the few seconds it took Charlie to sneak back out 

“Yeah yeah. ‘Knock to the tune of the DuckTales theme song…’ It’s not my first rodeo,” Your best friend shot back with a grin. Hurrying out of the room and down the hallway to get ready. 

Before the night was over she’d have dragged the whole damn sordid tale out of you.

Damn it… 

So much for one more night to brood over the kiss that almost was but never would be. But at least you got to be with your best friend. Which should lessen the sting of your upcoming rejection, at least a teensy bit. 

After all, what were best friends for if not for confiding in as they messed with your hair and turned you into a sci-fi Disney princess?

Start Here - Last - Next

After less than an hour locked in your own room, you needed to get out. You needed something, anything, to take your mind off of Dean. Plus, you were 99.9% sure that boredom could actually kill you. You just hadn’t let yourself be bored for long enough to test your theory out. And you weren’t planning to start now.

Sure, you might be a thief, and a wanted criminal. But your only real crime was that you were down to clown. And, though you knew it was safest to hide in your room. You couldn’t help but feel a tiny bit bored. What with no one other than yourself to make fun of, or clown around with, in the windowless room. 

So, against your better judgment, you’d decided to sneak back out to watch Sam and Charlie do their thing, play your designated role of class clown, and maybe suggest some fitting titles for the break-in job. Though you knew any naming ideas, no matter how brilliant, would be nixed in a heartbeat, since your team chose to go the boring case file route. Every. Single. Time. 

Though you still had names for all the team’s jobs. Even if the rest of your team members didn’t appreciate them. 

You were still bitter that they’d all vetoed your name for the Met Gala con. “Paint by numbers” had been a perfect fit as far as a con job name went. It covered all the bases; the big money, the crooked accountant AND all the paint.

Still bored, but now also a little miffed at your underappreciated talent for naming heists, you’d tip toed out of your room like the super thief you were. Looking left and right for arms-to-die-for Dean, before quickly hurrying to Brainiac HQ. Not even daring to pop into the kitchen to grab some snacks and a beer before you joined your two resident nerds in their office. Even though you knew you’d come to regret not stocking up...

Hacking wasn’t like in the movies after all. 

Usually it was slow and tedious. Like an endless waiting game for the rest of you, as Sam and Charlie attacked their keyboards looking for weak points and breaking down firewalls. Or whatever it was they did in their office. You’d never really been what one would call ‘technologically savvy’. 

It was a big day for you when you figured out how to use the grill function on the microwave on your own. 

So, pairing your lack of tech savviness with your inability to sit still. You knew the smart thing would’ve been to stop by the kitchen to make yourself a boredom survival kit. For some good ol’ fashioned boredom munchies. But hey… 

No one had ever accused you of doing the smart thing. 

“Hey IT, I think there’s something wrong with my WiFi…” You chirped as you fully entered the tech twins’ lair. Hiding your messy thoughts behind well practiced jabs that you knew would push your best friends’ collective buttons.

“Careful (Y/N), or I’ll actually lock you out from the bunker network completely,” Sam shot back without even looking in your direction. Completely missing the shit-eating grin you threw him as you lifted yourself up on Charlie’s desk picking up one of the many printouts littering her desk to read about…

One of the party participants, who would soon find himself in a jail cell thanks to your little group of do-gooders. This one was apparently the mobster’s chosen tech wiz. A hacker who went by the handle ‘Metatron’. Huh... 

Whomever this Metatron guy was, he sounded like a douche canoe. And one that clearly wasn’t in the same league as your girl. Since Charlie had already dug up all his dirty deeds, including some fanfiction he’d been writing about a guy called Chuck. 

Good riddance. 

Letting the paper fall back down into the pile, you turned your attention to your redheaded best friend. Who was busy eyeing you with both wary anticipation and exasperation in equal measures.

“How can I help Char?” You spoke up before she could go all She Hulk on you and kick you out of her lair if you didn’t have a good reason to be there. Because honestly, you needed something, anything, to do. 

“Oh! Alright, could you help me map out the office? Made a rough sketch on our software when you briefed Bobby, but we’ll need details for the actual job,” 

Charlie’s surprise wasn’t misplaced. Though you would do anything for your main girl. You normally, wisely, stayed out of her way when it came to what she was best at. Or at least came prepared with things you could do for her. 

Years alone on the run didn’t exactly make you a team player. Though you were working on it. You no longer hip tossed anyone who as much as tapped you on the shoulder without warning. Now you checked to see if they were friend or foe first before hip tossing them. Which was definitely progress.

Hopping back down from the front of the desk, you slid around to Charlie’s side instead. Leaning in to watch the layout she had built on the screen, you frowned at the little rectangle in the corner signifying the closet you were actively trying to forget. Before mentally shaking your head and refocusing on the pool table. 

“Pool table was a little more to the left, and Dean’s listening device was placed more towards the center pocket,” You corrected as you pointed your finger towards the screen. Careful not to touch the monitor in fear of facing the full wrath of the 5-foot-4-inch techie in the chair next to you. 

“Alright, anything else?” Charlie’s fingers flew across the keyboard, easily correcting everything at lightning speed as you pointed it out.

“The bar cart, it was closer to the desk, just enough space between ‘em for a full grown man to walk comfortably to the desk. Add bolts to the desk legs. It’s stuck to the floor. Safe location looks spot on. Other than that…” You contemplated the digital mockup of the room carefully, cringing when you were once again forced to look at the closet. 

“The closet, it wasn’t that deep. Cut it down by a few inches,” You added after just a second of hesitation, before continuing to make little, minute changes to the layout on the screen. Ensuring your team had the full visual to build any plans and backup plans, while doing your absolute darndest to ignore the closet as Charlie did her magic on the screen.

“Thanks (Y/N). Damn, how did you even manage to hide from the bad guys in here? For someone so set on showing off his wealth, his office is pretty… Minimalistic. If you don’t count the stuff he’s got hanging on the walls,” Charlie sighed and rolled her shoulders after you finally okayed the layout and offered up the best possible entry and exit strategies. 

“Oh… You know,” You started, really wishing you had a damn beer as you had to stop to clear your throat when your voice cracked over the words.

“We just hid from the heavily armed mafia goons in the closet…. As you do,” 

“Nobody does that (Y/N). How did you even fit?” Charlie’s surprised laugh was followed by her zooming in on the very closet you’d been avoiding looking at. Clearly already doing the mental mathematics in her head to work out how two grown adults could fit into the laughably small space. 

“We… Managed,” You said, pushing yourself away from the desk and walking back around it to cut off the view of the closet and hopefully put an end to Charlie’s questions. 

“Plus, it was probably why they didn’t even bother checking. We were… Lucky, I guess?”

--- 

Though you’d done all you could to help, which wasn’t much, you didn’t feel like returning to your room and brooding over a certain someone again. So, instead you stayed and annoyed your friends watched the two geniuses work. 

They were making quick work of a lot of the preparations. Which was easier with all the extra info your team had acquired during the party. A full chart of the big honcho’s organization was already up on the main screen, including bullet pointed entries for each and every member’s dark history. Your geniuses probably knew more about these guys than their own families. 

While the smaller screens surrounding the main display were filled to the brim with code as they found, and marked, the network backdoors needed for infiltration and extraction of information and money on the day. Each smaller screen another backdoor, firewall or network that they were currently in the process of hacking.

All while at the same time slowly but surely sourcing the account details of the many shell corporations and personal bank accounts of the whole organization. 

With your two geniuses on the case, your team was nearly ready to completely empty the wallets of everyone involved and throw them in jail as soon as you got into the safe. Once you had the paperwork for the charity, the list of donators and the pen drive hiding the nefarious use of the money, you’d destroy them at the click of a button. 

Well… Sam and Charlie would be doing the button clicking. You’d be too busy breaking into whatever safe set up the mobster had. And getting the hell out of dodge if shit hit the fan. Which, considering your track record, it often did. 

Meanwhile… So far your only contribution to the ongoing techie work had been to suggest the name ‘The Donation Drive” for the job. Much to the exasperation of everyone in the room. Which, at that moment, had only been Charlie, Sam and you. A small audience for your brilliant name, sure, but one that could still appreciate your talent. If by ‘appreciate’ you meant groan and reward you with easily won eyerolls of absolute disgust and exasperation.

Which of course was what you meant. 

Though, just as soon as you’d decided those annoyed groans were better than applause… Your victorious laughter had died in your throat once the door opened and Dean walked into the office. Choking you on your sweet victory like some form of unfair karmic justice.

He was still wearing those damned gray sweatpants, which… Of course he was. It had only been… What? Two hours since he changed out of his suit? There was no way in hell he’d make a quick costume change just to save you from imagining the oh so many dirty things wreaking havoc on your heart and your libido. It wasn’t like he could read your mind. 

And thank fuck for that. 

Shouldering the door the rest of the way open, Dean hadn’t noticed you right away. Too focused on balancing the armful of beers he’d brought with him. Choosing to do the smart thing, unlike you, and bring in an offering to the tech Gods whose office you were currently failing to hide out in. 

Yet, as green eyes lifted to greet the room, the smile on his lips had fallen a little as he spotted you. Which, though fully warranted, stung like a bitch for a split second. Before the older Winchester once again soothed that same sting as he replaced the former smile with another, softer, yet somewhat awkward crooked grin in your direction. 

“I thought you guys might be getting thirsty,” Dean said, after taking a second to clear his throat. Before gently putting down the beer haul on one of the free desks not filled to the brim with paperwork, and grabbing four bottles from the stash… 

Four. 

Damn it. Your escape route was closing fast, and your brain was still too hung up on the sight of him in those low hanging sweatpants to haul ass back to the safety, and boredom, of your bedroom.

Plus, seeing him standing there; boyish grin in place and two beer bottles left in his hand after quickly depositing one in both Charlie and Sam’s waiting grasps – offering up a thirst quenching bribe to stop you from running. It was… Familiar. In a way that made you simultaneously happy to see him and terrified at how easily he could put your paranoid self at ease. Happy because of the beers, of course... Not the sweatpants. 

Oh.. Who were you kidding? It was totally the sweatpants. 

Walking over to where you were still seated, half frozen, on the edge of Charlie’s desk, Dean slid in next to you. Leaning against the sturdy wood and scooting closer; close enough for you to smell the slightly spiced scent of his body wash. 

Quickly uncapping both beers, he gave you another small, careful smile before handing you one of the two chilled bottles. Which, effectively cut off any quick retreat you could make without it coming off as equal parts bitchy and weird. 

Sure, you were used to being seen as weird. It was kinda on-brand for you. But ‘bitchy’ was something you reserved for the bad guys. Not the people you worked and lived with. And definitely not for your infuriatingly handsome crush. 

So, instead, you busied yourself with some much needed dosages of liquid courage while throwing sneaky glances at the mercenary next to you over the edge of your bottle. Following his beer bottle to his lips, and nearly choking on your own beer from the sight of those tempting droplets wetting lips you’d been so damned close to tasting only hours earlier. 

Damn it all to the seventh circle of hell, that man looked good doing anything. And was also clearly solely responsible for your own recent oral fixation. And arm fixation… Not to mention thighs, hands, freckles, eyes… 

Fuck it, you were just fixated on the whole damned man. He was too stupidly perfect for his own good. And it always turned you into a bumbling idiot. Not that that was particularly hard. What with your mind always going a mile a minute while your mouth struggled to keep up… 

Aaaaand, you were staring again. 

You caught yourself just as Dean’s eyes locked with yours over his beer bottle. That tempting mouth curling up in a small smile against the lip of his bottle as you hurriedly refocused on the beer in your own hands. Once more, resigning yourself to stripping yet another poor bottle of its precious label as you tore on a corner of the paper to avoid meeting his eye.

Yet, keeping your eyes down didn’t mean you were free from the actual human drug that was Dean Winchester leaving you feeling dizzy and intoxicated. Even with your current vantage point being 70% bottle; you could still see him out of the corner of your eye. There was no way you could kick him - he was just too damned addictive.

His toned and muscular body, leaning nonchalantly against the desk, had caused his t-shirt to ride back up again. By now you were damned sure he was doing it on purpose. To show off that sinful v shape where his sweatpants were resting low on his hips and a flash of the well trained upper body that you could remember perfectly from your close encounter in the closet. 

Which… Of-fucking-course, sent you reeling back into that very same closet as you relived every heated second. Now with the added bonus of feeling Dean’s body heat where his arm brushed up against yours, and having the spiced scent of him fill your senses, sending you reeling back in time to that adrenaline fuelled moment. Leaving you nearly unable to tell reality from memory or dirty daydreams. 

Your own overactive mind, and the many, many dirty versions of that moment that your brain could think up on the spot, had you so lost in thought that you almost missed it when Dean finally spoke up, past some simple pleasantries with his brother and Charlie. 

If it wasn’t for the electrifying feeling of his eyes on you, and the way his deep voice always had pleasurable little shivers run up your spine, you would have missed the close call altogether. As Dean had clearly given up on getting you alone, and instead seemed ready to broach the subject you had been actively avoiding right in front of Sam and Charlie. Whom you knew where totally ready to listen in. No matter how busy they looked. 

As your best friend and adoptive younger brother, both had been the butt of many a joke told by you. And you knew they wouldn’t miss any salacious details that could be turned into ammunition in future back and forths. Both already knew that the quickest way to shut up your endless parade of snarky comments was to mention Dean. So if they had more detailed information to use against you… 

You mentally shuddered just thinking about it. 

“(Y/N), I think we…” Dean started, his voice low, though still very audible in the quiet room. Yet before he could complete his sentence you awkwardly cut him off. Saying the first non-sexy thing that came to mind to stop him from talking you into a corner where you were forced to face your own heartbreak in the middle of Brainiac HQ. 

“Sam was talking about the entry strategy!” Your voice was about two pitches higher than usual, and broke over the final syllable. So, totally not as smooth as you wanted it to be, but hell you were too panicked to care. 

“Especially since I’ll need my full toolkit with me… For the safe,” You continued, reeling your panic back in with a quick sip of beer and playing off the ending as if you were the literal definition of chill. If the meaning of chill had changed since the last time you picked up a dictionary. Which it might have, since the last time you picked up a dictionary was… Well... Never.

Smooth, (Y/N). Now you just needed to ignore Sam’s raised eyebrow, plus the most likely just as elevated eyebrow of Charlie, and hope it was enough. 

Luckily, your not-so-smooth diversion, no matter how awkward and obvious, still worked. As Dean dropped the subject of needing to talk with a tired sigh. His dark chocolate and whiskey voice once more became all business as he turned his attention back to the case.

“Yeah, we might need to rethink using a covert entry strategy…” 

Though you’d successfully changed the subject, you couldn’t focus on a single word Sam or Dean said. Not when the weapon specialist’s eyes still blazed like a forest fire; sending searing waves of heat through your body and into your core. 

Which only burned hotter as he covertly placed his free hand over yours. As if he was afraid you’d run away again. Which, in fairness, he had every reason to be. You were a fucking roadrunner…

Meep meep motherfucker. 

No way you were staying to have that conversation with him. Or going anywhere else to have it with him for that matter. 

Thief rule #1: Always run away from danger. No matter what.  

Those eyes, paired with the way the wet droplets of delicious beer rested on his pillowy bottom lip in a way that forced you to bite your tongue to keep from leaning in for a taste. And the feel of his calloused fingers on the back of your hand, unconsciously tracing circles against your skin…

Yeah, there was no way you could pay attention to a word of what the Winchester brothers were discussing. Past dully nodding along and adding in small sounds of agreement, in fear that your voice would break again if you tried to string actual words together. 

At least you could comfort yourself with the fact that you’d bought your heart a little more time before a certain Mr. Dean Winchester broke it into a million tiny pieces.

You knew there was no way you could keep running from the conversation that the stubborn weapon’s specialist seemed dead set on having. You just wished he’d give you a little time first. Just one night to have a cold shower, and revel like a school girl in the almost-kiss before he broke your heart. 

You just needed time to steel yourself for it. Maybe prepare a few semi-dirty jokes to hide your hurt. Or just literal clown paint… That could work too. Maybe Amazon could overnight you a few months’ worth of grease paint if you managed to keep running from Dean’s rejection for a few more hours?

Because you couldn’t fool yourself into believing he wanted to talk to do anything other than breaking your heart. He needed to talk things through with you to keep the peace in the bunker, that was all. For Dean Winchester, family and the job always came first. And that was all you were. A part of the family; a part of the business.

There was no way THE Dean Winchester liked you… He wasn’t stupid. 

In fact you’d reckon he was one of the smartest men you’d ever met. You didn’t survive long in his line of business without a good head on your shoulders. 

“... I think it’s our best bet for entry plan A. What do you think (Y/N)?”

The mention of your name falling from Dean’s lips was enough to pull you back into the real world again and out of the strange cocktail of sinful thoughts about his proximity mixed with self-loathing and early heartbreak preparations. Though, you’d clearly been checked out for far too long. Since you had no fucking clue what ‘Entry plan A’ was all about. 

“Yeah… Uhm. It sounds good,” You croaked, fooling absolutely no one. Especially not the eagle eyed former mercenary next to you that raised a cocked eyebrow and hid a smirk behind his beer bottle. Letting you know that he had noticed your not-so-secret glances in his direction when you’d used the shop talk to allow yourself to once more zone out and let the 50% of your brain reserved for thinking of the oldest Winchester take over.

“Just… Could you get me a copy of the details tomorrow so I can read through and digest it Sam? Might be some kinks that need working out,” You added, cringing as you swore you could feel Charlie roll her eyes at you from behind her many screens. 

The biggest kink being your damned brain.

“Alright, sounds like the plan’s coming together,” Dean said with a clearly fake yawn, pushing away from the desk and grabbing your empty beer bottle from your hand. Before taking a quick step over to one of the empty desks to place them next to the rest of the beer haul, much to Charlie’s chagrin. Though short, the distance still gave your mind, and heart, some much needed breathing room after having every single nerve in your body hyper focused on the mercenary for… Hell you didn’t even know how long it had been since he first walked into the room.

Yet, the reprieve was short lived, as the fast-as-lightning soldier was right back at your side before your brain could even signal for your feet to bolt for the door. His hand, that had just moments ago stopped resting against yours, reaching for you and easily grasping yours again. As if it was the most natural thing in the world. 

“We’ll leave you guys to it then…” He started, letting his thumb once again paint circles against the back of your hand as he got ready to drag you out of the room and into a heartbreak you still weren’t prepared enough to face. 

Yet, with the direct contact of Dean’s skin against yours, your brain had short circuited to the point of not being able to even think up a single weak excuse as you looked down at where his hand was swallowing up your much smaller one. The dirty little devil on your shoulder once more whispering sweet little nothings about how those hands would feel on your body into your ear and turning you into a tongue tied mess.

“Wait, Dean… Since you’re here…” Sam’s voice had never sounded as sweet as it did at that moment. Like a literal angel. If angels wore a fuck-ton of flannel and had more hair products than you. Which, hey… Who knew? They might? You’d never met an angel, and you were pretty sure you never would. 

What with your line of work and all. You doubted you’d be met with pearly gates when your reckless personality and bad ideas finally caught up to you and bit you in the ass. 

“What’s up?” Dean sounded slightly annoyed at his younger brother’s interruption as his hand squeezed yours. As if to make sure you hadn’t somehow managed to Houdini your way out of his grasp in the split second when Sam spoke up. 

Sure, you were an expert escape artist. Kinda came with the job. But even you couldn’t think of a way out of your current conundrum. 

“I was working the security details you’d mentioned during the debrief earlier into our plans… And I’d been meaning to double check the model of guns you saw the guards packing. Mind just coming over here and double checking the list for me?” 

Sam’s eyes were focused on the screen in front of him as he spoke. Which meant he completely missed the exasperated look Dean shot him. As well as the look of total reverence you threw his way at the same time. 

Sam’s need to have every detail ironed out before bed had just temporarily saved you from having your heart ripped out of your chest… Metaphorically of course. At least you hoped it was metaphoric. Since Dean didn’t look all too happy at the interruption. You however... 

God, you could’ve kissed the giant folder loving fool! If that hadn’t just felt… Icky. You saw him as your little brother. Yeah, no, that was just… Weird. You could’ve high-fived him. You could’ve high fived the hell out of him. If you hadn’t been too busy eyeing the door, ready to bolt the moment Dean dropped your hand. 

With an annoyed sigh, Dean let go of you to walk over to his brother’s desk as you stood perfectly still where he left you. Waiting for him to walk around the desk and give you some much needed space to make your escape. As Dean walked around the desk and leaned in to look at Sam’s screen, he threw a quick look up at you through thick eyelashes. As if he could hypnotize you to stay right there until he was done. 

But, unfortunately for the expert marksman… Unlike his perfect 20/20 vision, you couldn’t see all that well, all of a sudden. It was the weirdest thing… 

So, you chose to completely miss the silent warning in his eyes as you took a careful step backwards. Before clearing your throat and keeping your eyes focused on the door as you made your escape with a quick little wave of your hands and a jumbled and messy goodbye. 

“Well, you won’t need me for gun talk. I’m more of a stabby stabby girl, instead of… Y’know pew pew,” The words came out at a mile a minute as you hurried out of the room after throwing up some awkward finger guns. All the while pretending you couldn’t hear Dean calling out to you, asking you to wait up. 

Smoothest exit ever, you should change professions. You’d make an excellent clown. 

Actually, a career change might not be the worst idea. 

You could run away, join a circus. Get a stage name and put those under appreciated naming skills to good use. Since you doubted you’d survive much longer as a member of the Scooby Crew anyway. Not when Dean didn’t seem likely to drop the subject of your upcoming heartbreak.

Time to go buy some fucking clown makeup.

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