Dean thought he would be able to walk back into his hotel room, give Sam a vague non answer about his “date”, before claiming exhaustion and falling into bed with a half-hearted promise to talk in the morning. Instead he walked in to find Bobby there with Sam doing something that seemed to be somewhere between research and a bitch fit of a fight. Bobby would read half a paragraph before looking up with the sole purpose of glaring at Sam, before muttering to himself about dumbass idjits and looking back down again.

Great just what he needed right now, more drama.

“Sam, why don’t you go on a supply run while your brother and I have us a little talk.” He half expected his brother to argue, to demand to be part of the conversation everyone knew was coming. Instead sasquatch just got up and lumbered out, looking sullen and mutinous with every step. He better not take his mood out on baby, if he so much as squealed the tires there would be words.

“So I hear you made another deal, want to tell me about it.” They both knew that Sam had already spilled the beans, hell chatty Sammy was the whole reason the old cuss was here in the first place, but this was how things always went with Bobby. Someone would tell him something, he would nod along, then he would go looking for every other version of the same story. Trust but verify, that was his motto or one of them anyway. So rather than bitch or argue he just opened his mouth and let it all pour out, just like he always did with him.

“I just don’t get it Bobby, there’s something here I’m missing. Something I think we’re all missing, and I know it’s all right here in front of my face but I can’t fucking see it. It’s just been one crisis after another, I can’t seem to think, and when I do have a minute to breath the only thing I keep thinking about is… well.” He looked down unable to hold the other mans gaze while admitting to something so damn bush league.

“Your deal. The first one.” He nodded, every time he had a minute to think about Castiel and whatever it was that was being hidden from him all he seemed to zero in on was what was coming for him in a year. He was afraid, and he just couldn’t shake it, and that fear was making him slow and he knew it. Hell they all knew it.

“Yeah.”

“That’s understandable. Now why don’t you tell me about this second deal you’ve managed to fall into, gotta be honest boy I ain’t never heard of anyone making multiple deals before. You definitely got my attention. Maybe if you talk it out, you’ll see whatever it is that you’re missing.”

“Castiel showed up asking to tag along and observe a hunt up close. Saying no didn’t seem like an option especially after Sam already told us how quick he can go from cold to hot, his anger wasn’t really something I wanted to see up close and personal in a public place, ya know. So I said sure, not that there was much agreement needed, it seemed like he was mostly asking just to get a rise out of me. Like the entire thing was just to show me how much of a choice I didn’t really have. After that Sam kept trying to bait him, throwing out snide comments and stupid fucking looks for hours, so after a while I stepped out to get some air and when I came back all hell had broken loose. They were both standing, up in each others faces like Sam always does when he wants to make a point and make sure you listen, then I saw Sam pull out Ruby’s knife and plunge it into Castiel’s chest, the guy acted like it was nothing he didn’t even flinch, he just pulled the knife out and gave Same a look just daring him to try again. So I stepped between them and sent Sam out of the room, the guy had been pretty much eye fucking me all night and I hoped that he would choose to stay with me rather than go after Sammy right away. You should have seen his eyes Bobby, I got no doubts if this guy had managed to get his hands on Sam in that moment he would have ripped him apart, literally. He wouldn’t have even done it because Sam tried to kill him either, he would have done it because he was annoyed by his attitude, he was not taking the bitch face well at all. After we were alone I asked him what he wanted in exchange for not taking a run at Sammy. I know, I know, it was stupid, but what else was I supposed to do just let them tear into each other Sam wouldn’t have stood a chance and we both know it. He didn’t even hesitate, didn’t have to take a minute to think about it, he just offered up the dates in exchange, and here we are.”

Bobby sat still throughout the whole litany of information. Jesus, but the boy really was stuck somewhere between a rock and a hard place on this one. The fact that the offer was made so fast was more than a little concerning, but beyond that Sam’s impulsiveness was just as troubling. Sam had seen this thing before, he’d been the one to back up Deans assessment that it was more powerful than your average crossroads trash, so what the hell had been going through the boys head. Questions could wait though, he wasn’t all together caught up yet.

“So, what happened on this first one?” He hoped it wasn’t anything too god awful, he wasn’t sure what he’d be able to do for the boy if it was.

“I thought it was going to be something totally off the wall insane you know. Instead the dude took me on my perfect date, that also happened to reside down memory lane. He took me to the rock and roll museum I’ve been dying to go to since it opened and kept asking me questions about all the bands I like and all the meet cute get to know you bullshit. I was honestly surprised he never tried to hold my hand. Then he takes me to the diner where I had my last birthday meal with dad, I was twelve at the time, and orders me the same thing I ate back then. After the food, where he refused to answer any of my questions with anything less than Confucius levels of run around, here I am. One down nine to go.”

Well the boy was definitely right about there being something missing with this. There were too many open questions and not enough answers to go around. They would just have to come up with something then, to get those answers out of the one person who had them. First things first though, he had to tell Dean about Ruby, and the little information bomb she’d dropped on then. He hated to add more question on top of the ones he already had but he had a feeling that that was the only way they were going to get anywhere, so for now it was time to share and share alike.

 

Sam stood outside his hotel room, leaning against the trunk of the impala, while he waited for a little longer to give Dean and Bobby enough time to finish their heart to heart. Which is what this was even if neither of them would ever admit it. He was just about to go towards the door again to check for voices when he felt someone standing near him, turning quickly on hand going to the small of his back and the gun he kept hidden there when his mind finally registered who it was.

Castiel.

“What are you doing here? Date night is over.” He could barely hold back his shudder of revulsion that tried to rock his body every time he thought about his brother on a date with this thing.

“I came to see Dean of course but I find myself curious about what you are doing out here for so long.” Yeah, like he was going to answer any questions, but two could play this game.

“Oh yeah, well I’m curious about where my brothers contract is. Seems it’s not in hell where it belongs. Got any thoughts on where we should start looking?” He watched closely for any flicker of unease that his deceit had been discovered. He had to be worried now that his bosses knew that he’d tried to pull a fast one, but there was nothing. Just his usual condescending amusement. It was enough to drive a man to violence.

“Don’t worry Sam, his contract is right where it’s supposed to be. Those that need to know about it already do, unfortunately for you darling Ruby didn’t make the list.”

Sam stepped forward crowding around the smaller man hissing in his anger.

“We are going to find a way to free Dean from this deal, you won’t get him, I promise you that.” Finally, there was a flash of emotion in the other man’s eyes. Only it wasn’t what he thought he would see. He thought that the idea of losing a contract would annoy him, maybe even irritate him at the implication that they could outmaneuver him. Instead what he saw was an almost manic rage at the very thought of Dean slipping through his fingers. He knew that the demon had a strange fixation on his brother, if the monumental amounts of starring hadn’t cemented that fact then the details of the second deal would have definitely hammered it home. Now though, he was starting to worry about what the fixation could mean for their long term plans of saving Dean. If this demon was so dead set on having him, would breaking the deal even change anything?

“Which deal?” As the words left his mouth he licked his lips suggestively, that son of a bitch! How dare he imply that he would… that he could make Dean… No he wouldn’t let that happen, not any of it. This whole mess was his fault, if he’d been paying more attention, if he had actually kept up with his training after he fled from his family, if he’d done any one of a million things none of this would have happened.

“Both of them.”

“I look forward to watching you try.” The amusement was back, so quickly he wondered for a moment if he had imagined the rest. Rage like that didn’t just dissipate so quickly did it? Maybe not, but it could be buried that fast, which brought up the uncomfortable question of just how much rage was hiding under the laughter.

 

Ruby watched Sam stand toe to toe with a man who was obviously batting for the home team. This must be the demon who took good old Dean-O’s contract, now all that was left was to get a name. Sam obviously knew it, they were too combative for them to have not passed the introduction stage. In her experience if a demon, any demon, was going to the trouble of winding you up that far then they’d already given you a name to curse in your weaker moments.

And what was this about a second deal, there was no paperwork on that either, in fact there was nothing of substance about Dean at all downstairs. She had never heard of anyone making two deals, then again she’d never heard of a second deal ever being offered either. She needed more information, they not only needed this demon’s name, but the details of what exactly he was setting into motion. She knew the makings of a long term plan when she saw one, this guy was up to something and whatever it was if it was pissing off the youngest Winchester to this degree, it had all the makings of a hell of a good time.

Turning away from the motel she headed back towards HQ, if she was going to pull this off she was going to need some help. While she was sure she could get the details she needed out of little brother she was equally sure she would need a distraction for Dean if she was going to have a chance at trying for it. This was shaping up to be far more fun than she’d ever thought.

 

Sam laid on his bed and tried to sleep, he really did, but his mind would not stop turning. The first deal was bad enough, but the second could be equally as damaging and he had no idea how to get his brother out of either of them. After their little talk outside Castiel had come in and informed Dean that their next date would be three days from now, and the look of nausea on his brothers face was enough to twist his own guts into knots.

He knew that the demon hadn’t touched his brother, yet, but his suggestive move outside had brought that yet into sharp focus in his mind. This thing could do anything to his brother and there wouldn’t be a damn thing he could do to stop it, hell there wouldn’t be a damn thing Dean could do to stop it. He could not let that happen. He knew their best bet at finding a way out was in the books that Bobby had brought with him, but he also knew that Bobby would be able to get through them faster alone without him and Dean pestering him with a thousand and one questions.

No while Bobby was searching though all his books for an answer, Sam would need to go another way with it. After all there was no guarantee that the answers they needed was even in those books at all.

While they had been outside the demon had mentioned Ruby, now at first he’d thought he’d only done it to show Sam that he knew where his information had come from, but the more he thought about it the less sense that made. Ruby was the one who had told them that the contract wasn’t where it was supposed to be, and no one seemed to know what that meant for Dean’s deal, all that anyone seemed to agree on was that improper filing did not in fact void the contract. So maybe he mentioned Ruby to make him think that the source was tapped out when it was far from it. If you don’t want someone to find something sometimes the best thing to do is to convince them that even asking the questions at all would be a waste of time. Maybe Ruby knew more, and Castiel didn’t want him to find out what that more could be.

Mind made up he decided he would seek Ruby out on his own, he had questions and he was done waiting around for someone else to find his answers for him.

 

Castiel stood invisible next to the bed staring down at Sam watching his mind twist and turn itself around and around in a futile effort to find an answer when he hadn’t even found the right question yet. His plans to find Ruby were a little unsettling, because he knew that Dean would suspect his brother of his duplicity and follow him into danger. Not that he would ever allow that whore to lay a hand on his man, but that was beside the point. Sam was making trouble again.

He couldn’t understand it. History had shown Sam to be self-centered and less than attached to his family. He’d walked away once already without ever looking back, why was he making such a fuss now? It could not simply be the death of their father driving the two of them closer together, Dean had practically been a parent to the boy before and that relationship had not given him any pause once he’d decided to leave. Perhaps that was it, he had decided to leave before and now Dean was being taken from him without his consent. Humans were so messy, complicated, and overly emotional. He could not wait for this year to end so that he could take his Dean home with him, he would love hell… or at least he would love being with him in hell. He would make sure of it.

Leaning down he ran one finger along the contours of his beloveds face, his touch kept light so as not to wake him. He would need his rest for what was coming. Not only did he have to contend with Castiel’s own plans for him, but with the machinations of all those around him, it would be exhausting without proper sleep.

“Sleep my love, and dream of me. We will be together again soon. Until then I leave you with your loved ones.”

He would do nothing to stem the flow of poor decisions coming from the others, maybe if Dean could finally see his brother for the creature he truly was he would no longer fear Castiel. After all not all evil was demonic and even if they could not see it there was a darkness in the younger mans heart that was straining to burst free.  On the plus side, when Sam did invariable act on his ignorance and greed, it would open up a new opportunity for yet another deal. After all his beloved Dean had already readily made two with him, why not more.

 

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