Contains dialogue from the episodes 'I know What You Did Last Summer' and 'Heaven and Hell', it belongs to Eric Kripke, Sera Gamble, and Trevor Sands.
Part of my Deleted Scenes series. Full list of fics in reading order available on my profile page. They will make more sense if read in order. :)
Ruby finds the Wonder Twins in a bar. Sam's pretending to be drunk, which means they're hustling some poor sap out of his hard-earned cash. He used to do that all the time with her back when Dean was down under. Ruby was his wing-man. Or wing-woman, or wing-demon, or whatever. They played a couple, usually, with her nailing the part of the bitchy girlfriend who wanted him to call it a night and go home with her. It worked even better than Dean's my little brother's too drunk act, because most blue-collar stiffs have a ridiculously chauvinistic view of women, and the second she showed up and got her clichéd nagging-girlfriend on, the marks were more than happy to help Sam defy her wishes.
They seem to be getting on okay, though, with Sam slurring and stumbling and Dean asking the guy to take pity on his poor, tipsy brother. The guy refuses, and that's the whole point. But then Sam sees Ruby, and he instantly ditches the scam and makes a beeline to her. Ruby smiles smugly. That's more like it. She had him wrapped around her finger before, there's no reason she can't do it again.
"Hey," Sam says as he approaches her, and she gives him a much kinder and more sympathetic smile and returns the soft greeting.
"You got a lotta nerve showing up anywhere near me." Dean walks up behind his brother and glares at Ruby. Dick.
"I just have some info and then I'm gone," she tells him.
"What is it?" Sam asks, halfway between interested and concerned in that cute, pathetic way of his.
"I'm hearing a few whispers."
"Ooh great, demon whispers!" Dean cries sarcastically. "That's reliable."
Ruby ignores him. "A girl named Anna Milton escaped from a locked ward yesterday. The demons seem pretty keen on finding her. Apparently some real heavy-hitters turned out for the Easter egg hunt."
"Why, who is she?" Sam asks.
"No idea," Ruby lies. "But I'm thinking that she's important, 'cause the order's to capture her alive. I just figured that whatever the deal is, you might wanna find this girl before the demons."
"Look, maybe we should check it out," Sam says to Dean.
"Actually, we're working a case," Dean says, with a wink and an insincere smile. "But thanks."
"What case?" Ruby asks, knowing instantly that he's lying.
"Uh, we've got leads. Big leads."
"Sounds dangerous."
"Yeah, well, it sure ain't goose-chasin' after some chick who for all we know doesn't even exist, just because you say she's important."
"I'm just delivering the news, you can do whatever you want with it," Ruby returns hotly. "As far as I'm concerned, I told you, I'm done."
She gets off the bar stool and goes to storm off, when Sam grabs her arm to stop her.
"Wait, wait, this hospital Anna escaped from. Got a name?"
Ruby gives him the place and the city, and then she tugs her arm out of his grasp and walks brusquely out of the bar, grinning to herself as she does. If she knows the two of them like she's pretty sure she does, that little scene won't go over well at all. Dean will be pissed at Sam for believing anything that comes out of Ruby's mouth, and Sam will be pissed at Dean for being so quick to dismiss her when all she was trying to do is help. Seeds of discontent sewn.
The thing is, Dean wasn't supposed to come back. He was supposed to break the first seal in Hell but he was supposed to stay there after he did it. And it's going to completely ruin Ruby's plan if she can't get a handle on the situation.
She'd planned it all out so perfectly. Step one, save Sam's life. If there's one easy way to get to a Winchester, it's to get them owning you something. They don't take debts lightly. Ruby's heard tales of them driving halfway across the country to help out some guy who gave their Dad a good deal on a sawed-off shotgun twenty years ago. They're loyal like that. Which is so gross she could puke. Step two, tell him she could save his brother from being dragged to Hell. The way those two need each other, the level of sheer co-dependence, is staggering. Sam would obviously be beyond desperate to break Dean's Hell-deal – so much that he'd be willing to try anything, even listen to a demon. Step three, prove herself to them by pretending to be willing to sacrifice herself to save them from an army of demons. That one worked even better than Ruby thought it would. They both really believed she was ready to perform a spell that would neutralize every demon in the area including herself. Which really just proves how stupid they both are.
Step four, closer to the end of the race, give Sam a way to save Dean that required tapping into his psychic abilities, which Dean would never let him do; then at the last minute, when Sam would inevitably change his mind and demand Ruby help his brother, tell him it's too late. This was one of the more important parts of the plan, because it implanted the idea in Sam's mind that he could have saved Dean, if he'd only listened to Ruby. It made trusting Ruby seem like the right thing to do in the future. And it went off completely by the book, even more perfect than Ruby could have orchestrated. Complete with a nauseating, tearful goodbye and everything.
Step five, be there for him after Dean dies. All the research Ruby's done on Sam told her he would spin completely out of control without Dean, and the easiest way to break him is to urge the process along under the guise of being helpful. A hurt puppy devastated at the loss of someone he loves is as easy to manipulate as wet clay, and manipulate him Ruby did. Step six, sleep with him. The best way to a guy's heart is through his dick, and Ruby knew she could make him forget the disgusting, incestuous mess he and Dean were tangled up in. Sam may not have actually wanted to sleep with her – he pushed her away pretty roughly at first and he was almost angrier than Ruby had ever seen him at the mere suggestion – but he was weak and upset that night, and she taunted him into it. It was one of the more violent fucks Ruby's had in her life, but being a demon, she's sort of into that anyway.
It was child's play, but then everything went tits-up. Step seven was convincing Sam the only way to avenge his brother was by killing Lilith, when the time is right for the final seal to be broken and Lucifer to be gloriously freed. Ruby had this step well in motion, with Sam drinking her blood and honing his psychic abilities. But then Dean came back and cocked everything up. Sam stopped being so hurt and so lost; the clay hardened and Ruby couldn't get her fingers in to mold it anymore. At first, Ruby thought maybe everything would work out alright because Sam didn't tell Dean about what they were doing together. But then Dean found out what Sam and Ruby were up to, and he convinced Sam it was a bad idea. It isn't surprising – Sam's always been relatively brainless, just doing whatever anyone told him to, whether that person was Dean or Ruby. But Dean is always the Royal Flush on Sam's poker table, and he listened to him and cut ties immediately with Ruby. She's been trying to get a hold of him ever since but he's been ignoring her.
This, obviously, has to change. Sam has to be the one to break the seal. He's the only one who can – the only one of Azazel's kids left alive. Ruby forcing her blood down anyone else's throat wouldn't work; it has to be someone who's had it in them for as long as Sam has. It has to be someone with psychic powers created by demon blood when they were a baby. He's the only person on the planet who fits the criteria, so Ruby has to get him back somehow.
Luckily, it might end up being easier than she originally thought. She's been doing some spying and digging on her own since Sam kicked her to the curb, and things are not as peachy in Sam-and-Dean-Land as the two of them would have the world believe. Dean was pissed when he found out about her. And he's lying too. As far as Ruby can figure, he must remember Hell. She doesn't know anything that can wipe 40 years of memories and not affect the memories he has of his previous 28 years on earth. Not even an angel can do that, she doesn't think. When Sam finds out Dean's been lying to him about something so important, he isn't going to be happy. And Ruby's been to Hell. She spent a lot more time there than Dean did before they finally managed to turn her into a demon. She knows what it's like, and she knows it isn't something you come back from without major internal battle-scarring. Dean is not the person he was before the pit. Sam would have to be stupid not to have already noticed, even if Dean's pretending everything's fine.
There are rifts between them right now; little cracks that will only take some gentle prodding to turn into craters. And that's exactly what Ruby's going to do.
She follows them everywhere they go after she leaves them at the bar. They check out the hospital and Anna's parents' house, and eventually they find her in a church. Alastair is following them too, though, and that's not good. If he gets to Anna first, this whole thing will be ruined. Sam has to know who she is first. He has to learn not to trust the angels. That step is just as important as the rest of them. Sam has to be inclined to be wary of them and their motives. It'll make it easier for him to side with Ruby.
Ruby takes Anna to a cabin where she'll be safe, and she briefly possesses a disgustingly fat and sweaty maid to give Sam her whereabouts. They take their sweet time showing up, and two of the finest on Heaven's dick-squad show up not too long after. They fling her into a wall and they beat the hell out of Dean, but Anna banishes them with some kind of crazy spell, which Ruby totally didn't know she could do but is totally freaking awesome. Ruby's gonna have to learn how to do that.
Later, in the iron-lined bunker of some friend of theirs where they go to hide Anna from the angels, Ruby tosses Dean the hex bags she made to temporarily keep them safe.
"Hex bags?" Dean asks as he catches them, on the other side of the door Ruby can't cross over.
"Extra crunchy. Hide us from angels, demons, all comers."
"Thanks, Ruby," Dean says with a small but genuine smile, and Ruby frowns a little and narrows her eyes in surprise. If she's not mistaken, it looks like Dean's starting to trust her too. He even asks Ruby to keep an eye on Anna when he goes upstairs to talk to Sam. That isn't part of the plan, but it definitely doesn't hurt.
A blind psychic named Pamela helps Anna remember she's a fallen angel. Ruby apologizes to Sam when they're alone, for bringing the whole mess down on them, and tries to convince him to take another hit of her blood so he can exorcise Alastair, but he refuses. Every day that goes by that he doesn't drink, his powers diminish, and Ruby can't have that. He doesn't need to listen to her right this second, but he'll need to eventually if Ruby's plan is going to get back on track.
She waits until Sam falls asleep and then she leaves and summons Alastair. Now that Sam knows the angels were willing to kill Anna, Ruby has no use for her anymore. The demons can have her, for all Ruby cares. It turns to shit on her like maybe she should have known it would – Alastair and his lackeys pick her up and strap her down and carve into her like a Thanksgiving turkey, but then in the end it all works out okay. The angels find Anna and the boys, using Sam as leverage to break Dean, and she gets her grace back and saves them from Alastair. And Ruby gets to look like a hero again, a martyr who bled for the cause. She's not super jazzed about having to actually bleed for the cause, that knife hurts like a bitch when it's poked into the right spots, but whatever. Ruby's had worse. And really, this is all about the endgame. Sam knows the angels are just as dickish as demons now. On top of that, he's gonna figure out pretty soon that Dean remembers Hell, if he doesn't know already, and that will bring back all of that guilt and self-hatred he'd been wallowing in when Ruby first found him. And all of it will send him straight back into her arms, easy as taking vital organs from a baby.
Check and mate.