Chapter Text
You had been with them for what felt like a lifetime. After losing your parents at a young age and being taken in by the gruff and solitary Bobby Singer, Sam and Dean Winchester were like the brothers you had never had, and the family you desperately craved. You wanted to be like them, even as a child with only a rough understanding of the things that went bump in the night. From years of idolizing them, to being old enough to trail behind them like a lost puppy when they ventured out in search of their father with nothing but a list of monsters to go off of, you had been by their side every step of the way, learning and growing to be a formidable hunter. But deep down you knew the degrees of separation between you and them, that their paths would always be inline together, while yours would be just a bit off, parallel to theirs. You would never be blood, never have a better reason beyond a lonely child’s misplaced love leading you on to this path. Even now, years later with more scars and more nightmarish memories to keep you awake at night, you still felt like you had something to prove. You wanted to show them, or the world, or your pride, or God if he was even watching, that you weren’t just a thorn in their sides, another potential casualty to haunt them on the road. You were still family even if it wasn’t by blood, and you would lay down your life to protect them.
No one had ever stopped you on this path, and if not for the demon named Crowley, no one ever would have.
The first time you met him was that fateful night, stuck between Sam and dean and facing him in the dark hallway of his home. Jo was waiting outside anxiously, and you had all risked your livelihoods on the chance of this demon in front of you possessing a potential weapon to kill Lucifer.
“It’s Crowley, right?” Sam spoke. Crowley had not looked like what you were expecting from the crossroads demon. Average height and build, donning an expensive suit and coat. His hair was thin and swept to the side, his aged faced showing no surprise as he met the sight of the intruding hunters standing in his opulent home. Had you walked past him on a busy sidewalk somewhere, you probably wouldn’t give him a second glance, but as his cold eyes darted between Sam and Dean, his lips curling into a devilish smirk, you felt a shiver run down your spine. The power that radiated off him would lose out to his unassuming figure and would make anyone stop to take a second look.
“So, the Hardy Boys finally found me? Took you long enough.” He spoke, his gravelly accent gracing your ears.
Not one for getting the last word in, you surprised yourself when you responded. “Your shitty security caused some delays.” His eyes landed on yours, brows raised as if he just became aware of your form standing between the two tall men on either side of you. You swallowed as he eyed you up and down, and the action was not missed by the man.
“And the Hardy Boys brought their pet with them, lovely. Much better company than that angel you’ve been keeping handy. You must be [Y/N], yes? My demons have told me all about you and your little heroics- the ones that have lived to tell, of course.” You scowled as he stepped closer, just shy of the rug you had marked with anti-demon sigils. Your heart sped up as his eyes flickered downward, knowing full well of the trap below him, and then back to you. “Come now, that little rabbit heart of yours betrays that angry look on your face. While you’re cuter than I thought you’d be for someone who spends so much time with these hulking morons, you’re certainly as bright as them.”
Dean scoffed from beside you, and you feel the heat of his anger radiating off him. “Back off, ugly. You know why we’re here, so cut the crap.”
Crowley shrugged his shoulders. “Now, now, I’m just teasing the little rabbit. I know not to mess with other people’s toys. I’m a demon, not a fool.”
That bothered you more than his stab at your intellect. “I’m nobody’s toy, asshole.” You growled.
“[Y/N].” Sam warned, cautious of the demon in front of you.
“Feisty, are you?” Crowley teased, ignoring the brothers.
“Enough of this,” Dean snarled, “where’s the damn colt?”
Crowley rolled his eyes, reluctant to end his teasing. He took a step back and your lip twitched in irritation. The three of you watched as he pulled the gun in question for his coat pocket. “Oh, you mean this? This is what you’ve mucked up my home and slaughtered my security for?” he scoffed. “Come along, then. I believe we have some business to attend to.”
The three of you followed him into his office, a dark room with expensive looking furniture that somehow makes so much sense, yet it does strike you as funny to imagine him at his desk, running through contracts as if he were in some other business other than taking people’s souls.
“Do you know how deep I could have buried this thing?” Crowley states, toying with the gun in his hand. “There’s no reason why you or anyone else should know this exists at all, yet I’ve been kind enough to throw you a bone and tell you about it.”
“You told us?” Sam asked, rightfully confused.
“Rumors, innuendo- all sent by me through the grapevine.” Crowley looked positively bored, lazily aiming the gun at Dean, who stood still under his empty threat. “I want you to take this to Lucifer and empty it into his face.”
“Uh huh.” Dean nodded. “I call bull on that. Why would you want the devil dead?”
“It’s called survival.” Crowley said. “But I forgot you two at best are functional morons, and now you’ve brainwashed that one into being a human shield for your shenanigans.”
“Human shield?” You scoffed, while Dean huffed, clearly offended as well.
“Yeah- well, you’re functioning morons- mor… crap.” Dean, thankfully, didn’t continue.
Crowley continued. “Lucifer isn’t a demon; in case you’ve forgotten. He’s an angel, one famous for his hatred of humankind. To him, you’re just filthy bags of pus.” He looked down at the gun in his hand, and back toward the three of you. “If that’s the way he feels about you, you can imagine what he thinks about us.”
“But he created you?” Sam asked.
“We’re just servants… Cannon fodder.” You didn’t like it when Crowley’s eyes flickered toward yours and brushed off the weight of his comment. “If lucifer manages to exterminate humankind, we’re next. So, help me. Let’s all go back to simpler times, back to when we could all follow our nature. I’m in sales, dammit! So, let’s call it a night. I give this to you, and you go kill the devil.”
You stared at Crowley in a moment of thought. You believed him, and it’s not as if anyone else had offered an opportunity like this to the three of you before. “The enemy of my enemy, right guys?” you said softly, glancing at the two brothers. They looked at you, then to each other, and then to Crowley.
“Uh… Yeah. Okay.” Dean said, while Sam nodded in agreement.
“Lovely.” Crowley handed the gun to Sam.
“You wouldn’t happen to know where the devil is, by chance?” He asked.
Crowley, put a finger to his lips. “Thursday…” He trailed off. “Ah, yes. Birdies tell me he has an appointment in Carthage, Missouri.”
“Great, thanks.” Sam said and proceeded to cock the gun while pointed at Crowley’s head. Your eyes widened in shock as he pulled the trigger. The click of the empty barrel followed immediately after.
You stared, open mouthed as you watched Crowley, both you and Dean frozen in shock. The silence was so loud, until Crowley clicked his tongue as if he were none the wiser to what Sam had done.
“Right, yes, you probably need some more ammunition.” he said casually, moving out of firing range and shuffling through one of the drawers in his desk.
Dean shook his head in exasperation. “Aren’t you signing your own death warrant? What happens to you if you go against the devil and lose?”
Crowley scoffed. “Number one: he’s going to wipe us all out anyway. Number two: after you leave here, I go on an extended vacation to all points nowhere. Number three: how about you don’t miss, morons!” He snapped, enraged as he tossed Dean the bullets and disappeared from the room, leaving the three of you to stand, coincidentally, like morons.
“So, uh… Which of us has the best aim?” Sam asked.
Dean shrugged. “Well, if you’re toe to toe with the devil I’d say it’s you, Sam. Just make sure there are some damn bullets in the gun when you do it.”
“It was an impulse, okay!” Sam exclaimed.
You snorted. “Because those have worked out so well for you, huh Sam?” You turned on your heel, following as Dean left the room.
“Oh, come on!” Sam said, shouting after the two of you.
You were never one for secrets between the hunters around you. It was difficult enough to have them after growing up in their presence, and being on the road with them made any semblance of a personal life impossible. You had given that up the moment you decided to hunt alongside them. So, when you found yourself hours later being roused from your slumber parked at a truck stop along the highway by the vibrating of your phone in your pants pocket, you found yourself staring down at a message from none other than the demon himself and were presented with a newfound secret of your own.
“Do expect to be sent a bill for that rug of mine you ruined. I don’t like it when people mess with what’s mine. Will be in touch. Xx”
You glanced up from your phone to Dean and Sam in the front seat. Sam’s head propped against the window, breathing evenly, and Dean sleeping lightly in the driver’s seat, arms crossed tightly against himself. Beside you, Jo was curled up in the seat, fast asleep. You looked away and back to your phone. Yes, you told yourself. One little secret couldn’t hurt, could it? He was on your side, right? And besides, you could always tell them later. The ride to Bobby’s would take a while, and from there the trek to Carthage would be a long one. With a quiet smile, you reassured yourself, and texted the demon back.
(xxx)xxx-xxxx “Sorry wrong number Xx”
(666) “Oh, so you like to play doy do you?”
(666) “coy”
(xxx)xxx-xxxx “haha, you can’t type”
(666) “It was one mistake. What are you, 5?”
(666) “are you laughing at me?”
(xxx)xxx-xxxx “Duh”
(666) “People have died for less.”
(xxx)xxx-xxxx “If that’s the case you should’ve killed me already”
(666) “No, you’re already proving to be far more entertaining to me alive, darling. Xx”
And without even realizing it, you would let the window of appropriate time to reveal it to them slip by, allowing the eventual strings of text messages and occasional calls to dig you deeper into a hole. It was harmless, you thought to yourself. A secret that was barely important to the big issue in front of Sam and Dean and would only distract from the real threat of the Apocalypse.
You had found it strangely enjoyable to speak to him, and maybe you had begun to see him in a different light than those around you had. He had, of course, gifted your group with the one weapon thought to kill Lucifer, which was more than the angels had offered in terms of assistance. Sure, it was all part of his ability to look out solely for himself, but hey, the enemy of my enemy, right? It was only text messages of aimless talk. Questions of leads and hunts between meeting Crowley and finding out Lucifer’s location. He would ask for progress, then move on to something else. His “extended vacation” was clearly one of isolation that the crossroads demon had not been fully accustomed to, and in his desperation, he picked you as the unassuming victim of his boredom.
Had only you realized that the first encounter you had with Crowley would make that path of yours, the one that you thought would always be just to the right of the one Sam and Dean were on, stray even further from theirs, intertwining your own path with that of the crossroads demon.