A/N: And finally, this chapter we get to see how Skye is doing...which is not well. This was a hard chapter, due to me being worried about getting the "voices" right for everyone in it. Hopefully I was successful. Big shout out to LovinJackson as always for her help!! And to everyone who is reading and leaving me reviews. Thanks guys! You keep me writing! HUGS

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Medicine Bow, South Wyoming.

If there was one thing Ava Wilson didn't handle well? It was boredom. Maybe it came from being a secretary and spending too many days with nothing to do but sit behind a desk and file her nails or answer the phone? Maybe it simply came from the fact Ava knew something big was just on the horizon and she didn't like the idea of waiting for it?

Rocking on her chair, Ava flipped over another card. Playing Solitaire was so not how she expected to be passing the time when the end of the freaking world was like, a hair's breadth away.

Looking up from her game, she could see Jake Talley reading some crappy crime novel he'd had in his duffel bag all the way from Iraq. He seemed to be happy enough to read it, but then, Ava figured it was more a case of enjoying the peace and quiet of not being in a war zone.

Lily Morrison was another story altogether. The girl was staring out a window, idly flicking ash from her cigarette on autopilot between drags. Ava knew the girl was still grieving the death of her girlfriend, but with any luck, she'd get over that soon enough. There were more important things to be worrying about than a dead girlfriend…or fiancée in Ava's case. Brady had been a sweet guy, but Azazel had offered Ava such a sweet offer. How could she say no to a guy that was offering her the world? Literally?

Glancing to her left, Ava saw Andy curled up in an armchair, asleep. The guy was a major pain in the ass as far as she was concerned. Whiny, a complete coward. If it wasn't for his nifty little ability, Ava would have told Azazel that they didn't need the guy.

"You know? I don't see why we have to sit around waiting? We have the Colt, we know where the gate is….why don't we just go and open it now?" Ava huffed out loud, slapping another card down on the table impatiently.

"Because there's a little thing called an alignment that we need to be in place first, Ava. It's one of those cosmic laws of the Universe….but hey, if you think you're good enough to rewrite age old laws that bind events such as this? By all means, go ahead…." Azazel walked into the room, the wink he threw at Ava belying the annoyance he was feeling. "Oh…wait…I have the Colt. Not you. And since I'm the one who gave you your cute little ability? I think its best if you just shut up here and now before I lose my patience any further."

"Okay, okay…I'm sorry." Ava backed down with a frown, her shoulders slumping. "So why do we even need the girl, anyway? Dean didn't kill Sam. We might as well just get rid of her."

Azazel cocked one eyebrow at the girl as he fixed her with a bemused look. "Did I die? Did someone put you in charge all of a sudden? Cause you know, Ava…I'm beginning to think that forwardness I liked so much in you, is suddenly not so appealing…"

He smiled as the girl backed down, paling at his words. She'd gone from being such a shy, nervous little thing, to a full blown killer in such a short time. It was bound to go to the girl's head, all that power.

And if the attitude continued? He'd open her up to see how her insides looked as decoration for the room.

Azazel looked over the rag tag bunch of children he had gathered, finding himself bitterly disappointed with what he'd be given. Oh they were loyal. They were certainly ready to follow his every order…well, with the exception of Andy Gallagher…but he'd get over that pesky conscience soon enough.

But for all the good points…… the group of people before him weren't Sam Winchester. They just didn't add up to that one boy that Azazel had been hoping to have at his right side now. He'd been ready to fully endorse the kid as a leader, backing him all the way in the war….but no; Sam had thrown the offer back in his face. And for what? His family? It was an insult. Those Winchesters weren't Sam's family. Oh sure…he was their's by birth, by genetics. But Azazel's blood had been flowing through Sam's veins since he was a baby. Marking him, making him special…opening him up to the destiny that had been awaiting him.

And Sam had thrown it all back in Azazel's face.

In hindsight, maybe he should have gone at it from another angle? Maybe he should have tried to corrupt the oldest boy, Dean, rather than kill him? Perhaps Sam would have followed his big brother?

It was all moot now, of course. Sam had made his choice, picked his side in the war that was in motion now. A war that was going to swing forever in favour of the demon world after tonight.

"Make sure you're ready to move when it's time. " Azazel told the group. "I'm going to talk to our guest and make sure she's ready for her task."

The moment Azazel had left the room; Jake looked up from his book, looking straight at Ava with a smirk. "You keep pissing the man off like that…and I'm gonna be running this operation soon enough."

Ava answered him with her middle finger and a sour look.

Jake shrugged and chuckled quietly. "You might have more deaths to your name. But when push comes to shove and Yellow Eyes wants a new leader? Who you think he's gonna pick? A secretary? Or someone with a military background?"

The sullen look on Ava's face was all the answer Jake needed as he went back to his book, still chuckling.

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Pacing the basement had gotten old about the same time as Skye's left knee began to ache. It was an old injury. At the tender age of eight, Skye had been walking her dog with her older sister when the German Shepard had suddenly bolted after another dog. The lead had been slipped over Skye's wrist and before she'd had time to react, the dog had pulled her over on the road, splitting her knee open to the bone.

Sixteen stitches later and Skye had been left with an ugly scar and a knee that in the last couple of years had started aching from time to time. Especially when it was overworked like now.

But Skye continued to pace, wearing a shallow trench in the dirt floor. It still beat sitting on her ass, feeling sorry for herself. That wasn't going to get her out of this. She needed to think, to try and find a weak spot, anything she could turn to her advantage.

Skye had been ready to die after Ava had lied to her. The thought of her son being dead had just torn her heart out. But Andy had risked anything to give Skye back hope. She knew now that Connor was alive and safe. He was with Dean. It gave Skye a reason to fight now. As best she could anyway.

Whatever they wanted with her? Skye wasn't going to do it.

The basement door opened above her. Skye turned towards the stairs, pausing mid step and waiting to see who it would be this time. The man that came down the stairs, beaming like the cat that got the cream wasn't familiar at all. But the moment Skye saw the sickly yellow eyes watching her from within what was otherwise a handsome and friendly face; she knew who she was dealing with.

The Yellow Eyed Son Of a Bitch was how Dean had usually described him. Skye found herself backing away, looking around for some sort of weapon, but still coming up empty.

"I really must apologise for the accommodation. It's not exactly five star. But I like to think it has that nice, homey, down to earth feel about it." Azazel smiled widely as he stepped off the bottom stair.

"The view could be better…" Skye deadpanned, folding her arms across her chest to hide the fact she was trembling. It was terrifying, being face to face with the demon that had caused Sam and Dean so much pain. "Maybe something with a balcony next time?"

"Funny. Using humour to mask how you really feel….not unlike someone else we both know."

"Shut up." Skye growled softly, watching Azazel carefully.

"Attitude too. You'll fit right in with that family…" Azazel smiled. "Which brings me to why you're here." He approached Skye and slowly circled her, revelling in the way she seemed to draw into herself, unwilling to let him even brush against her. The smell of fear was so rich, despite the display she was making.

"You used me to set Sam up." Skye said accusingly. "What other reason did you need?"

"Oh Skye…you're worth much more to me than a little misdirection. In fact, you're the key to me gaining all the power I could ever want. Because of you? I'm going to bring Hell to earth."

"You already have. Or haven't you been watching what's happening out there? The people that are dying?"

Azazel waved his hand dismissively in the air. "Collateral damage. Casualties of war…however you want to paint it. It's always the civilians that pay the highest price." His smile returned a moment later as the demon winked at Skye. "I need you to help me usher in a new age of peace. A world where demons rule mankind."

Skye snorted, watching the smile fade from Azazel's face. "Exactly how am I supposed to be doing that?"

"With this." The demon pulled out an old western style revolver and handed it to Skye. She turned the gun over in her hand, her eyes widening as she saw the inscription down the barrel, the markings carved into the handle. "This is the Colt. The Colt. The one you took from John….the gun that can kill you."

"The one and the same." Azazel nodded. "It's a little less impressive when you see up close, isn't it?"

Skye lifted the gun, struggling to pull back the hammer, taking comfort from the sharp click as the gun cocked before she aimed it at Azazel's head. "Looks pretty damn good from here."

"Oh my…" Azazel raised his hands in a mock surrender, his voice light and full of scornful laughter. "How could this have happened? How did I not see this coming?" The mirth was gone a moment later as the demon fixed Skye with his yellow eyes, a small smirk on his face. "Hear me out first…"

That gave Skye pause. How the hell could he stand there face to face with the Colt and be so damn calm?

"All I want you to do is open the Hell's Gate for me. Just walk up to the door, turn the key and bingo, the rest of your life gets to be candy canes and lolly pops. Connor can live to a ripe old age, rich and happy. You get to watch him, maybe have a few more pups to add to the family bloodline. I'll even throw in Dean for you, alive and unharmed until the day he dies of old age….and all I'm asking in return? Is one little thing. What do you say?" Azazel lifted his eyebrows in expectance of her answer.

Skye pulled the trigger, hearing it click hollowly. Nothing happening.

"I'll take that as a no?" Azazel shook his head, acting disappointed. "Did you really think I'd be stupid enough to give you the Colt loaded? Apparently you've picked up the Winchester's ability for stupidity too."

"Fuck you."

Skye was suddenly thrown back across the basement, slamming into a wall hard enough for everything to white out for a moment. She could taste blood in her mouth and realised she'd bitten the inside of her cheek on impact. Blinking away tears, Skye tried to move and found she was pinned by some unseen force. Her heart was pounding in her chest, wondering if she was about to draw her last breath at the demon's hands.

Azazel stepped up to Skye and leaned in, meeting her frightened gaze only inches from her face. "I was willing to play nice. To give you everything you wanted and you throw it back in my face?"

"I'm not helping you. Open your own gate!"

"There's a slight problem with that idea. You see, the whole area is one big Devil's Trap. But Samuel Colt was no fool. He not only made sure that no demon would enter the place…but no one with demon blood in them either. Which leads me to my little problem…and you being the key to solving it." Azazel informed her pleasantly.

"I've already told you I won't do it."

The pleasantry was gone, Azazel's smile evaporating and a hard sneer replacing it. "You're under the impression you have a choice here. Let me make this very clear. If you don't open that gate for me? You'll die. Slowly….in agony. But not before you watch me kill your son. I'll peel the skin from his bones. I'll make you eat his eyeballs. I'll bring so much pain down on his little head that you'll be screaming his name for an eternity in Hell. Am I making myself clear?"

Tears slipped down Skye's cheeks as she tried to remove that horrible image from her mind, feeling like she wanted to vomit, wishing she could die instead. "Alright…" The word was a broken whisper as she hung her head.

"What was that?"

"I'll do it….whatever you want."

Azazel's smile was back full force. "I knew you were a smart girl. Just keep that sweet little face of your son in mind, Skye. I'll be back for you soon."

Once the demon had left the room, slamming the door behind him, Skye was released, falling to her hands and knees. She curled her knees in under her and sobbed, hating herself, praying that Dean would find some way to get her out of this.

Trying to recall happier memories, Dean's face, and Connor's laugh.

Anything but the harsh reality of what she was facing.

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Valentine, Nebraska.

"Missouri, we're here." Bobby gave the psychic a gentle prod in the shoulder, smiling to himself as he watched her blink blearily, sitting up to take in her surroundings. The sight of gently rolling hills met Missouri as she looked through the windshield, noting the simple yet attractive looking farmhouse to her right. The gentle sound of cattle lowing to each other echoed around her.

"And just where exactly is here, Bobby Singer? You've dragged me out into the middle of damn nowhere!" Missouri fixed Bobby with a stern look that covered her anxiety.

"This is Phill McCallister's place. He's a good man. Knows his stuff and watched my back on a lot of hunts. We set up the idea of hunter's safe house here when the signs started to show that the demons were on the move. Sort of a rally point for everyone." Bobby explained as he opened the driver's door and climbed out.

"You still haven't told me where we are, Bobby. I might be a minder reader, but I sure as hell don't like going into that grease soaked head of yours unless I have to."

Bobby shot the psychic a dirty look and nodded his chin towards the house. "We're about half an hour out of Valentine."

"Nebraska?"

"No, Cuba…what do you think?"

Missouri gave Bobby a look that could freeze lava. "I'm thinking my foot's going up your ass if you use that tone with me again, Bobby."

The mechanic waved Missouri off, unable to hide the smirk on his face as he led the way to the house.

The sharp, crisp sound of a shotgun cocking cut through the air and Bobby froze in his tracks, bringing his hands up slowly. "Easy Phill…it's just me and Missouri like I told you over the phone."

A large man stepped out on the porch of the house, the shotgun held easily in his hands. Phill McCallister stood just over six foot tall with broad shoulders and a body that spoke of a life of labour on a cattle ranch. A scruffy beard framed a weather worn face that looked a little older than its 35 years, but the eyes that watched Bobby were sharp like a hawk's. "Man can't be too careful, Singer. You know that."

Bobby caught a silver hipflask as it was tossed to him. He eyed it for a moment, then lifted one eyebrow in a question mark as he looked up at Phill. "Holy water?"

"Yup. You and Missouri be kind enough to have a nice long drink of that, we can let you inside."

With a casual shrug of his shoulders, Bobby twisted off the cap and took a long swig of the water, smiling at Phill as soon as he'd swallowed it. He then handed the flask to Missouri and waited patiently while she followed suit.

"Satisfied?" Missouri asked coolly.

"Guess so." Phill drawled lazily, tipping up the shotgun and resting the barrel on his shoulder. "You've missed out on breakfast, but there's plenty of coffee in the pot. Come on in." He turned and walked back into the house, letting Bobby and Missouri follow him inside.

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"Bobby Singer…it's about time you got here." Ellen Harvelle spoke up from her seat at the kitchen table. Her daughter Jo was sat across from her, idly playing with her father's knife, much to Ellen's disapproval as the former Roadhouse greeted Bobby and Missouri.

Ever since Bobby had sent them here to hide out after the Roadhouse burnt down, Jo had been arguing with her mother. That they should be doing more, that hiding out wasn't the answer. Ellen could see so much of Bill in her daughter right now and that terrified her. John Winchester had been there when Bill died and although Ellen didn't believe the man was responsible for her husband's death? She wasn't ready to completely absolve him of it either. Winchester's were trouble. Plain and simple. Dean and Sam had used Jo as bait on the one hunt she had gone on with them. That was one hunt more than Ellen ever wanted her daughter going on

For a while, Jo had left the Roadhouse, had worked in bars, done some small time hunts on her own and with Gordon Walker. The man was like an Uncle to her, taught her the ropes, how to look after herself on a hunt, watched her back.

It was through Gordon, that Jo had begun to learn the truth about Sam Winchester, how he was going to become something evil. Some great leader for the demon world.

Coming face to face with Sam in that bar in Duluth, had really opened her eyes to what Gordon had been saying about the Winchesters being a threat. Dean was blind to the danger, that much Jo was sure of. Bobby too.

" Jo-Anna Beth, you want to go make sure that coffee's hot?" Ellen looked pointedly at her daughter, the look inferring she should put the knife away. Now.

"How you doing, Jo?" Bobby asked quietly, noting the tension between mother and daughter.

"I'm fine." Jo bit off abruptly, pushing her chair back sharply and heading to the percolator. "How is it out there?" She looked over her shoulder at Bobby, some of the fire in her replaced with worry.

"It's bad. Real bad. Lot of good people are dying out there." Bobby stated honestly. "Where's Ash?"

" Dr Bad ass is still asleep." Ellen drawled tiredly. "He was up all night trying to figure out what all these signs are leading to. Said something about a planetary alignment being due to happen tonight."

"Sam was right." Missouri shared a look with Bobby. " You should call John, let him know."

"John?" Ellen sat up and looked sharply at the pair. "John Winchester? Then Gordon was right."

" About what?" Bobby asked coolly. He didn't like the idea of Gordon Walker and the Winchester's being mentioned in the same sentence. The man was bad news.

"That he was back. Gordon said he was some sort of winged demon now, released from Hell itself. I'm surprised to see you in one piece if you've been with them, Bobby."

"Now you just hold on a minute.." Bobby growled. He'd had his doubts at first too, but the more the mechanic saw of John and the boys, the more he realised that all they were. Despite everything, they were still the family he loved and trusted like his own kin. There was no way he wanted to have them being seen as the enemy thanks to Gordon Walker. "Ellen, when did you last see Gordon?"

"Last night." The touch of cold metal to the back of his neck made Bobby freeze. He knew the feel of a gun barrel when it was that close. To his left, he could see Missouri's eyes widening in fear. All the conversation had distracted the psychic to the point where she'd been caught off guard….Bobby too. "Now just take it easy, son.."

The world exploded red, then began to slide sideways as Bobby took a heavy blow to the back of the skull that brought him to his knees before he pitched face first to the floor. As everything faded out, he heard Gordon Walker's smooth, smug voice. "You shouldn't have sided with the Winchesters, Bobby. You picked the wrong damn side of this war to be on…"

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A/N : Don't you just hate cliffhangers? LOL Next part should be up soon!