She wonders if his brother ever sees him like this.

Sam Winchester never looking as calm and confidant as he does pointing the colt with arm outstretched at the crossroads demon. She's far enough away not to be noticed, always being talented enough to duck the bitch's radar, but keep an observant on him.

Watching the exchange she finally sees what Azazel must have all along. Such potential in those puppy dog eyes, such wrath radiating from him. She hears her name, takes small pride in the fact that she can still rustle so many feathers, and readily ignores the threat about getting what's coming to her. They'd have to find her first, and that's still something they haven't been able to do.

Sizing up the demon's form, she didn't think it was his type. Her fingers playing with the ends of her own hair, she had always heard Sam had a thing for blondes. The conversation must not be going the way Sam wants it to because he's looking increasingly annoyed, and even at this distance his itchy trigger finger is completely obvious. Nothing is iron clad, she thinks. If that were true she'd still be in hell with everyone else.

The gun goes off and she curses under her breath for letting herself get distracted.

The demon flickers, burns, and fades away.

Right between the eyes, knew you had it in you Sammy boy, she thinks.

He looks around searching for wherever he guesses she might be.

"It's done," he calls out.

"Bravo," she replies, stepping into view and clapping her hands as her lips stretch into a smile.


"What is it this time?" He asks.

Never says hello, she thinks. And here she thought he was supposed to be some kind of gentleman.

No, he just gives her a scowl and some half-assed retort when she starts to pick off his plate. No fries this time, tater-tots, and damn if they aren't little nuggets of joy. It's a wonder, she thinks, taking her time to eye what she can see of Sam's body stretching above the table. That he and his brother aren't a couple hundred pounds overweight with all the truck stops, diners, and deep fried crack houses she always finds him in.

He's concentrating on his laptop, making a big show of ignoring her even though his eyes lift to hers every few seconds.

"Your brother knows."

He looks up quickly, before he can catch himself, then sighs and leans back into the booth as if he's only now realizing that it was inevitable.

She eats more tots, points at him, and grins while still chewing.

"Hope you honestly didn't think that it wasn't going to get around," she teases. "Offing a demon like her is going to ring a few bells Sammy."

His brow furrows at her, and she realizes that he still has it on him, is suddenly aware of its place underneath his jacket. He folds him arms over his chest. Yes, he knew, but still hoped against hope anyway.

"You wanted her dead, she's dead." He replies.

"That's right," she offers up. "But color me surprised that you don't seem all that remorseful. Not even for that pretty little body left behind."

Something twitches in his eye.

"I did what I was told."

"Hmm and what if Azazel got such willing participation? Didn't really think you'd be such the willing soldier so quickly Sam."

"You talk like you know me."

"I know all about you Sam." She takes his soda and sips. "Think he'll say thank you?"

He doesn't answer.

"What do you want?" He asks instead.

She shrugs, eats more tots, and smiles.

"I was hungry."


He's restless and barely sleeps. She can practically see the imaginary stopwatch in his mind, counting down every second his brother has left. Yet another cheap motel in the middle of fucking nowhere and she can lock onto his presence as deftly as a sniper.

Kicking up dust as he scuffles around in the moonlight, she watches as he plots, prays, and begs some higher power she's never seen for an idea on how to save Dean.

It would warm her heart if she actually felt the thing, if she actually cared. She makes her presence known stepping out from behind the tree she'd been leaning against.

"Do you do anything else than just follow me around?" He asks when he notices her.

The surprise is gone from his voice. Guess he's finally getting used to her impromptu appearances here, there, and everywhere.

"Can't sleep Sam?" She asks her own question, ignoring his.

He doesn't answer her, she doesn't answer him, and it's a stalemate they've been coming to more times than she can count.

She gets down to business.

"You got the gun?"

Oh hello, she thinks, catching the glint in his eyes, the fear and anticipation of what she'll ask of him. Time for the real Sam to come out and play.


She circles around him feeling very much the tigress eyeing her prey, chuckling softly to herself.

"Well I'm looking for something to get shot," she says brushing a teasing linger of a touch across the back of his neck, taking pride in how it makes him shiver.

"I'm not your own private hitman," he replies in a low voice.

"No," she concedes coming around to face him. "But I bet you're Dean's."


They're fighting about something. She doesn't know what because it's hard to hear the exact words they're throwing at each other over the pounding rain, but she leans against the wall next to the door trying her best to catch them anyway.

Dean is a stubborn one that much is easy enough to pick up. It seems like he's reveling in his death sentence and absolutely refuses to let Sam meddle with the deal.

She knows the catch, of course, and even Sam wasn't naïve enough to think that killing the crossroads demon could actually do something to fix it all at once, but did it still.

"I did it for you!" She hears clearly, though unsure just who said it.

Dean storms out of the door suddenly, and it takes a last second dive into the shadows for him not to notice her. She's lucky he's so mad because she knows a skilled hunter like him would spot her the second he set foot on the ground had his head been clear.

Explanations for why she's continually stalking them wouldn't be so forthcoming in the moment.

Sam is in the doorway watching the Impala race off against the rain, tires spinning and kicking up mud everywhere.

"I know you're there," he says softly.

When she comes into view, he isn't surprised to see her at all.

Admittedly it's a thrill she'll miss.


The first time, it isn't exactly what she expects.

She can feel every ounce of his self-loathing with each thrust of his hips and it only makes her want him more. Feeding off his guilt, relishing the way it drive into her.

He's so warm, she's so cold, and somewhere in the middle it works.

Oh Sammy, Sammy, Sammy, she breathes into his skin.

Cheap motel sheets, a storm raging outside, a man who doesn't care that's she's underneath telling him everything he never wanted to hear.

She thinks:

Oh cliché's, cliché's, cliché's.


She recognizes the look after he beheads Gordon Walker. Not her idea this time, rather, something born out of necessity. There is remorse surrounding him, but only after the deed is done, she knows it's never ever present during.

After Dean patches up his hands, after Sam tells him he needs some time to himself, she finds him.

And oh, is he not in the mood for her.

He shrugs away at her touch, walks a few feet ahead, but doesn't quite leave her behind. She keeps in stride, forever the little fallen angel on his shoulder, waiting for an opening. Ten, maybe fifteen minutes later, he stops at some bench alongside a country road.

When he sits so does she, never expecting the invitation to do so.

He refuses to look at her, and she smiles knowing he can still see it out of the corner of her eye.

"I thought Dean was the broody one," she says. "But you're just trying your best to measure up, aren't you Sammy?"

"Please stop calling me that," he mutters.

She puts her hand on his leg. "What should I call you then?"

A beat.


Shooting up from the bench he starts to walk away then stops. Turns back and stares her down. She knows the threat of the colt when she sees it, but the trick in Sam's deception is that it doesn't quite fill those puppy dog eyes of his the same way as when she's actually seen him use it.

He pulls it out anyway.

"Think you filled your quota for tonight," she says all smiles.

It's not as if she isn't used to this by now, can't quite recall how many times he's pulled it on her. She knows he won't do it.

He clicks back the hammer.

Hopes he won't do it.

"Kill me and you'll be no closer to saving him."

"I'm not any closer now."

Getting up from the bench she moves close, stopping directly in front of the barrel, daring him all the same because they've done this dance before. He clicks the hammer back down, puts it back in his jacket.

"Got a soft spot for me don't you Sam?"

He scowls at her.

"You act like I care," he says.

She moves in whisper close, lets her lips hit the pulse on his neck, and he doesn't shy away.

She says:

"You act like you don't."


Six months into their agreement his demeanor is changed step by patient step. He's no longer dismayed or dismissive when she appears, merely regards her as if they're old friends who get together to do bad things.

They meet in some smelly old alley behind a bar and the conversation goes:

"I need a favor." Her.

"Of course you do." Him.

"Aw, don't be like that. I promise it will be worth both our whiles." Her.

"Fine, let's get it done." Him.

Grabbing his hand and pulling him along, she leads him to the car she'd stolen a couple days ago, someone's beat up old Camaro that she thought had a certain mystique.

Tonight is a big one, an old colleague that took her months to track after they crawled their way out of hell. Her skin is crawling with anticipation and she spins and stands on her tip-toes, sliding her arms around his neck and makes him taste the promise of things to come on her lips.

She opens the door and starts the engine.

He doesn't ask any questions.

Two hours later they're covered in demon blood kissing feverishly in the back of her stolen car, pushing against each other, nipping, gnawing, and pressing down hard into torn leather seats.

Feeling frisky tonight, she thinks. Going to get there aren't we Sam? Going to get the job done?

"It shouldn't feel like this," he suddenly says against her.

"What?" She gasps, her eyes focusing on the blood smear evident across his forehead.

"What I do for you, what I do for Dean shouldn't…"

If it wasn't for his occasional crisis of conscious he wouldn't be one-hundred percent Sam. That's what she tells herself anytime he questions their arrangement. But this small regression into little boy lost, after a big successful kill at this inopportune moment is such a fucking turn off. So she shuts him up with her mouth, trying to derail his train of thought and refocus his attentions to her.

He pulls at her shirt, those big hands of his sizzling against bare skin. The colt falls out of his jacket and clatters to the floor causing him to still. She smirks up at him, tilts her head and slowly reaches down for it. Maybe she'll indulge his doubts a little.

"If feels wrong," she starts. "Because you deny yourself every second this isn't in your possession."

There's no predictable scowl this time just some kind of haunted curiosity.

"I've seen the real you," she goes on. "Every time you hunt, every time you use this." She puts the colt between them. "A piece of you is freed."

"What do you m-"

She cuts him off again but he starts to pull away and she catches the front of his jacket.

"We're not done here," she says low and sweet. "Don't you dare think about stopping."

His head dips back down, mouth teasing her through the fabric of her shirt.

She tilts her head back, lets out a content sigh, lets her eyes go black.

He slowly slides her pants off her hips and she looks back to him, smiles at his acceptance of her gaze and sucks in a breath when his eyes almost go as dark as hers.

I see you, she thinks. I see you.


She's met Dean three times.

The first a mere month into showing up with jobs for Sam, when he was still suspicious of her every move and intention, when she still ate or drank half of whatever he was having, when she'd linger around just to piss him off even more.

The older Winchester showed up at the booth she shared with Sam, and she was glad the younger one had the colt, because the look Dean gave her when he realized who she was, she knew flat out he would have shot her dead on the spot.

The second she swooped in to save the day again, not being able to bail the both of them out without getting noticed by Dean this time around. She stood calm and collected as they fell to their knees and gasped for breath, thanking their lucky stars she was there.

They never said as much of course though she could see something like it in Sam's expression. Dean merely gave her his version of the look of death, and she took off before he could find words to go along with it. The most he got out was 'hey!' to her retreating back.

The third he came looking and she let him find her, thinking that it was just one of those inevitable things she'd have to deal with.

He came roaring up all big and flashy in that shiny black car of his, skidding to a halt on the gravel road. Smirking at him as he crawled out of the door, came storming up to let go with the yelling, she merely folded her arms and waited.

He wanted to know who the hell she thought she was, and yeah, he knew that in the obvious way.

"What do you think you're doing with Sam?" He asks.

"I'm helping him."

"By supposedly helping me right?" He replies. "Last I checked that noose is still waiting for me and whatever dirty deed you cook up for Sammy doesn't seem to be pulling it any further away."

"Not big on faith are you Dean?" She asks.

He scoffs.

"Didn't think so," she goes on. "But think of it this way, Sam helping me, helps you. And in the end we're all going to be lottery winners smiling with that big fake check."

"I not as dumb as you or the brainiac might think," Dean shoots back. "He's not telling me squat but I know what you've been up to."

"Such the consummate big brother," she mocks. "Can sell your own soul to save him, but the second he tries to return the favor you're against it."

"Is that what you call it?"

"Maybe I do, and for someone who's doing what she can to save your ungrateful ass, I'd drop the attitude."

He smirks.

"Maybe I ought to just drop you."

She smirks back.

"Look at you with the big boy pants on," she laughs. "You don't have it, so you aren't dropping anyone today."

He clearly doesn't like being called on his bluff.

"He would never let you talk to me if he thought you were going to kill me."

She can't quite describe his face for knowing that much about his brother.

"What do you want with Sam?" He asks instead.

"Exactly what I told him, that I want to help from time to time. To figure out what was done to him."

"How that working out for you?"

"Just fine," she smiles. "We've discovered some tasty little tidbits."

Now that perks his interest.

"He hasn't said anything."

"And why would he?" She fires back. "When you were always so accepting of his place in this little mess? Oh wait, you never were." She starts to walk around him with confidence in her step. Pushing all the right buttons with a Winchester turned out to be such a fun little game.

"You're afraid aren't you? So afraid that he didn't come back the way you thought he would. That he was changed, darker, colder. That what you did for him might have been for nothing. That your big and noble sacrifice did nothing to detour him from the destiny Azazel laid out for him."

"You don't know what you're talking about," he shoots back.

"Ooh, got me there Dean. Except that you know I'm right. And you don't want me and Sam out there saving your life because you don't want to live to see what he'll become."

"Yeah? What's that?"

She grins.



Almost a year until Sam's patience finally runs dry. When she shows up at the bar he'd been attempting to drown his sorrows in because Dean was off somewhere taking full advantage of the time he had left.

She convinces him to follow her outside and once they're there he grabs her by both arms and slams her up against the cold brick wall of the building.

"He doesn't have much time left," he seethes. "I think I've waited long enough for your miracle cure. I've done everything you've ever wanted, and I've done it well. So what's it going to be? Are you finally going to make me use that bullet with your name on it?"

She laughs, can't help it, actually enjoys him being so rough.

"What are you going to do?!" He shouts. "He has weeks Ruby! Weeks!"

She smiles up at him, gives him that little pouty look that had worked whenever he'd gotten angry before. Hesitantly he lightens his grip, runs his hands up to her shoulders and lets his forehead sink against hers.

"I'll kill you," he says softly. "If you don't-"

She snaps her fingers.


He lifts his head, the confusion clear.


"He's not going to hell."

He stares blankly.

"Are you serious?"

She smiles. "I've never lied to you Sam."

His anger is swift, the strength of his hands back to squeezing her as hard and he can and for a moment, she actually thinks he might hit her.

Instead he says:

"All that crap you put me through, all those hoops, all those things you made me do! All those people! This whole time all you had to do was snap your fucking fingers?!"

She wiggles herself out of his grasp, puts her hands on either side of his face, kisses his stiff mouth.

"I never made you do anything," she says. "I only asked."

Darkness fills his eyes, the real Sam coming back into play.

"My boy," she coos. "It's always been about you remember? And you're right, you held your end up, did me more favors that anyone should have asked for, so now I'm holding up mine."

She wraps her arms around his neck, rests her head against his chest, thinks about why she wanted Sam Winchester back into the fold.

"Why?" He asks softly.

Because, she doesn't say, I had a great love once. Looked just like you, talked just like you, was strong and honest and noble just like you. And when he found out what I was he sent me back to hell. Broke my heart Sammy, and before you laugh yes, demons have hearts. What did I tell you? Not all of us are the same.

They all laughed at me, Azazel the most, for falling for one you. For believing that there were happy endings, for believing in love at all. You helped me more than you think Sam. All those demons we killed? All those bastards who mocked me? One of them held Dean's contract. But when we killed him it wasn't done yet. There were more and I knew you'd never help me if you'd known.

"Tell me."

He looked just like you, she thinks. But it couldn't be the same. You had to be darker, be colder; you had to be more like me. Don't you get it Sam? This is what you were born for.

She doesn't tell him any of these things, because if he discovered just how vulnerable she was to him, he'd turn and leave her here for manipulating him so thoroughly. For enjoying it as much as she did. She turns her head slightly, presses her lips into the side of his neck, and laughs so cold and hollow.

"Why'd you do it Ruby?"

Because I'm a cold bitch, she thinks, because I wanted you, because I wanted you to stay when it was over.

What she says is:

"Because I could."