TRIGGER WARNING: There is mention of attempted suicide (not Dean nor Cas) in this chapter. Just a heads up. It's when Meg enters. If anyone would rather not read that part, just hit me up and I'll give you a different version of that scene (email or another post) or tell you what you missed. I'm completely willing to do it, so just let me know. Love ya'll! :)

Castiel slowly woke up, hearing papers being shuffled nearby and the sound of the air conditioner coming through the vents. He could, also, hear the soft playing of Frankie Valli coming from a small radio. He opened his eyes to a warm lit room with blood red walls and mahogany floors. The room was empty, except for the black loveseat he had been laying on and its twin across from him along with a bookcase on the opposite wall. He turned around and saw Azazel calmly sitting down at a desk reading papers through thin framed glasses.

Castiel bolted upright, suddenly more aware of his surroundings. He glared at Azazel, "Where am I?"

Azazel glanced up with a smirk on his face, "We're at my place of course."

Castiel narrowed his eyes and stood up quickly from the couch. He instantly felt dizzy and disoriented, falling back to the couch. Azazel chuckled as Castiel grabbed his head and closed his eyes, "You took a pretty nice blow to the head. I wouldn't be making any sudden movements if I were you."

Castiel ran his fingers through his hair, feeling a small bump on the back of his head. He let out a humorless laugh. How could he have been so naïve to turn his back on Azazel, even in a public place? "The blow that I'm assuming you delivered?"

Azazel grinned, "Oh, no, I never get blood on my hands. Though, I did give the order."

Castiel tried to ignore the throbbing of his head, pulsating violently against his temples, "And what are you going to do with me now that you have me here? Kill me?"

Azazel gave him a crooked smile, "Nothing for now. The main guest hasn't even arrived yet."

Castiel felt his heart stop, "Who?" He asked, but his stomach dropped, he already knew the answer.

Azazel shuffled some papers and took his glasses off, then stood from his chair and walked around the small desk. He leaned against it with his arms crossed, grinning widely at Castiel, "Why, my dear Dean of course."

"Dean is not your's," Castiel practically snarled at the man.

Azazel held up a finger, "Maybe that's true, but not for long."

Castiel rolled his eyes, and then closed them. He took a deep breath, desperately praying for the pain in his head to go away. He needed to think of how he was going to get the hell out of here. Whoever Azazel really was, he definitely had some man power and in Castiel's state he didn't even think he could take on Azazel let alone any lackys.

When he opened his eyes again, Azazel was staring at him with a knowing look, "There's no use in hurting your pretty little head over it, Castiel. There's guards all over this place. You'll never make it out unscratched, if even alive."

Castiel swallowed as Azazel confirmed what he had already guessed. Azazel continued, "And I doubt you have any fighting skill that could take down a Demon, even the ones on the lower part of the food chain."

Castiel scoffed, "A demon? What? Are you saying that you have the key to the gates of Hell or something?" Azazel seemed to get more deranged by the minute.

Azazel laughed, "No, but if there was such a thing I'd love to get my hands on it. Have you really not caught on yet? You're quite slow."

Castiel just narrowed his eyes at him and Azazel sighed, "Demons as in The Demons? You know the gang? One of the factions of the Knights of Hell?"

Castiel blinked and his mouth dropped slightly. It seemed to be the reaction Azazel had wanted since he chuckled at it. He bounced off the desk and strutted towards Castiel. Castiel pressed his back against the couch in response. Azazel leered at him as he leaned over him with his hands on either side of Castiel's head. He whispered in a sultry voice that dripped with menace, "Do you understand who you're up against now? I'm probably the most powerful man you've ever met. Everyone looks up to me around here and obeys my orders at the simple flick of my wrist. These people are willing to do anything to please me. They'd even die if I asked."

Castiel tried to not let the fear he was starting to feel rise in his chest show on his face. He took a deep breath through his nose and didn't take his eyes away from Azazel, "No matter what you do, Dean will never become who you want him to be. He'd never give his life for your's."

Azazel clenched his jaw, "Even after all that I've said, you still won't back down will you, Castiel? You'll fight till you're bleeding on the floor and giving your last breath before you let me have Dean, won't you?"

Castiel's voice was steady and confident as he replied, "Yes."

Azazel raised his eyebrows, "You love him that much?"

"Yes," Castiel didn't back down from Azazel's intense stare.

Azazel nodded and leaned away from Castiel, "Well, I have to respect your devotion and loyalty."

Azazel looked out the large window behind his desk for a second and then, without warning, swung his fist at Castiel. Castiel almost fell off the couch from the impact and turned back to Azazel before the man's knuckles came into contact with his face again. Castiel felt like he could barely see through the pain that was fogging his mind and he felt blood running down his face. But Castiel was more prepared when Azazel threw the third time and he stood up and caught his hand, before hitting him square in the jaw with his other hand.

Azazel stumbled backwards in shock and brought his hand up to his nose. When he pulled it away and saw blood, he chuckled looking back at Castiel, "I think you broke my nose."

Castiel panted heavily as his head swarmed and promised, "Come near me again and I'll do much worse. And what happened to not getting blood on your hands?"

Azazel smiled wickedly at him, "I think I can make an exception for you." Then, a young man walked into the room. Castiel's eyes followed him until he stopped in the middle of the room. He couldn't have been more than sixteen and his all black suit hung loosely on his thin body. He had black eyes and hair to match that was slicked back. His eyes widened at the sight of Azazel, "Master, are you alright?" His eyes flickered to Castiel, looking slightly frightened.

Azazel rolled his eyes and walked over to his desk grabbing a tissue to hold to his nose, "I am fine, Tom." He turned to him with cold eyes, "Is there a reason you interrupted my friend and I?"

Tom glanced warily at Castiel before answering, "Yes, he has finally arrived. Brady is looking after him downstairs."

Azazel smiled, "Very well, bring him here in a few minutes. I need to finish the conversation I was having with my dear friend, Castiel."

Tom nodded and left the room with one last curious look at Castiel. Castiel tried to stand straighter as he glared at Azazel, "Don't you dare lay one finger on Dean."

Azazel met his eyes with a forbidding gaze, "Wouldn't dream of it. But Castiel, I think you should be worrying more about your own safety."

Castiel didn't respond and Azazel spoke in an amused tone while still maintaining an air of threat to it, "Well, obviously I'm not letting you walk out of here alive. I think it's about time I show Dean how serious I am about him returning to my side." Azazel smirked at him and tilted his head, "And killing you in front of him seems like it would do just the trick."

Castiel didn't allow his expression to show the fear that was shaking his chest. He wouldn't say he'd been surprised at Azazel's words, but hearing them clearly spoken still sent a panic through him. He wasn't going to give Azazel the satisfaction of getting to him, though. He cleared his throat and spoke in what he hoped was a confident voice, "Even if you were to do that, Dean won't come back to you. If anything, he'd just want to get revenge and you don't want to be looking over your shoulder for Dean Winchester all your life, do you?"

Azazel's grin faltered, but only for a second and his smirk was soon back in place, "Well, that would mean Dean wouldn't leave me, wouldn't it? Even if the circumstances are less than what I wanted. I'm sure eventually I could turn him back around."

He was happy with any attention Dean would give him, even if he was trying to kill him? Castiel's eyebrows scrunched together as he looked at Azazel in disgust, "You're sick."

Azazel merely shrugged in response, "Maybe I am. Doesn't make any difference to what's going to happen to you." He strutted to the door and looked over his shoulder before twisting the knob, "Better make your final moments worthwhile. Get your final thoughts in order or whatever." And with that he left Castiel alone in the room. He heard the soft click of the door locking and it felt ominous as anxiety gnawed at Castiel's heart.

DIVIDER

As soon as Azazel left the room, Castiel collapsed against the couch. He rested his elbows on his knees and held his head in his hands. There was a menacing pulse against his skull that felt like a jackhammer. He didn't dare close his eyes, though, knowing that he'd instantly become unconscious. He couldn't move his head too quickly without his vision blurring and feeling like he'd pass out. His body was screaming at him to just give in and close his eyes, even if just for a moment, and it was extremely tempting. But his mindset was unwavering. He needed to keep his guard up and stay awake, ready for when Azazel walked back through that heavy wooden door.

His thoughts wandered to Dean, praying to whoever was listening that the man was alright. In the moment he was thankful for Azazel's infatuation with Dean, knowing that it'd at least keep him alive. For now. A cruel voice in the back of his head reminded him that it had been Azazel's own men who had attacked Dean in Italy and Azazel telling him people disapproved of Azazel's obsession with Dean. Castiel could clearly imagine a few of the gang members roughing Dean up a bit before Azazel could step in.

The memory of Dean bruised and broken in an Italian hospital flashed through his mind. His heart tightened and it became hard to breathe as if a heavy weight was sitting on his chest. An overwhelming feeling of anger flooded through him as he remembered Dean struggling around his apartment on crutches and almost falling. Mary's worried voice on the phone and thanking Castiel for taking care of Dean. Dean's depression of being bedwritten for a month. The small table covered in medication. Anna's hysterical voice on the phone telling him Dean's in the hospital and it didn't look good.

God. Castiel tried to stop his thoughts before they could dive any deeper into heartache. He needed to figure out how they were going to get out of this, if there was even a chance. No. Castiel couldn't think like that. There was a chance and he'd find it if it killed him. He just hoped that wouldn't have to be the case.

Castiel leaned against the back of the couch and looked over at the window. It was pitch dark outside and he couldn't see a thing. The window took up most of the wall and he walked over to it wondering if this could be his chance. He searched the panels for a latch or anything, but with no look. The large window was built into the wall and apparently didn't open. He sighed in disappointment.

As he turned around the door opened and Castiel felt his stomach drop, but then he saw who the person was as she snuck in and rushed to shut the door behind her.

Castiel's shoulders relaxed slightly as she walked towards him, "Meg?"

Dozens of emotions flickered across her face, before she finally decided on anger. Her voice was strong, but Castiel could still hear fear in it as she spoke. The words came out breathless like she was overwhelmed with emotion, "I would slap you if you didn't already look like you had the shit beat out of you!"

"Azazel –"

Her eyes stared into his and Castiel found it hard to look away, "I know who it was. This is why I warned you, Castiel. I told you to break things off with Dean before any of this could happened. He's going to kill you, Clarence! Do you realize that? Azazel is going to kill you and there will be nothing quick about it."

She looked over her shoulder at the door behind her, "I told Azazel some of the boys had turned on him and shot the guys guarding the safe room. He ran off to go get a handle on things. Even with his obsession with Dean Winchester, he can't ignore that kind of problem. It should stall him for fifteen minutes before he goes to get Dean."

Castiel felt relaxed at her words, but confused. "You're a Demon, aren't you? Just one of Azazel's little minions. You're the one who's been informing him about me, aren't you? Pretending to be a fan of my art. Why do you even care what happens to me?" Castiel retorted frustrated, wondering why this woman who he barely knew was helping him.

She did slap him at that and he looked at her in shock. She pointed a finger at him angrily and growled through her teeth, "Don't youdare think you know anything about me. You have no idea why I'm here or why I to act like every other damn moron who waits on Azazel hand and foot."

"Enlighten me," Castiel glared at her feeling his cheek sting and guessing there was a red handprint on his face now.

Meg sighed frustrated and glanced away from him, "We're cousins."

Castiel's eyes widened and she scoffed, "Yeah, and don't say you see the resemblance. His father took me in when I was a kid after my parents died. And with Alistair being the leader of the entire faction, I couldn't exactly chose a different profession. Family business and all."

"Alistair?" Castiel asked confused with his eyebrows pulling together, "Azazel said he was the leader?"

Meg rolled her eyes, "Well, he's next in line and when Alistair got terminally ill, he took over. He's running the gang into the ground. Cain's going to drag us all to Hell sooner or later. We used to be just drug dealers and would only kill during drug wars, but now with Azazel in power money became second after Make everyone fear my name."

"Cain?" Castiel repeated, trying to keep up with her.

She explained impatient, "Cain, the Father of Murder. You know, the guy who runs the Knights of Hell? The Demons are just a faction of the national gang. If there was a top dog, he'd be it. And a couple decades ago he changed his ways and gave us one law to follow, To not kill recklessly. And he's very serious about it. A couple years ago, he took out the entire west coast faction. Hundreds of people brutally murdered because they didn't listen."

"And you think the Demons are next?"

Meg's face paled at the question, but she nodded, "Soon enough. He'll get to us."

A moment passed between them and Castiel asked, "Why are you here, Meg? What? Did you decide to turn a new leaf and help me?"

Meg stared at him for a second, her face softening and she shrugged, "Why not? There's nothing left for me here. Alistair's dying and he's the only one I owe my life to. I don't owe Azazel and his bloody tantrum shit. It's the perfect time to escape with Azazel so focused on Dean. He won't even notice I'm gone. I need to get out of here before Cain makes a visit, anyway." She paused and then, smirked at Castiel, "Besides, I like you, Clarence."

Castiel tried to not feel hopeful at her confirmation of helping him out. There were still things she hadn't cleared up, "Haven't you been against me this whole time? Burning down my apartment? Giving Azazel information on me?"

Meg sighed and looked down at the hardwood floor. Her leg ticked nervously, while she leaned on the other, "Azazel just assigned me to observe you. See who you were and what your connection to Dean was. I started going to your art exhibits around six months ago."

Castiel tilted his head, "But Dean and I weren't even together then? How did you even know what our relationship was, anyway? Did you stalk me?"

Meg looked at him offended, "No, I'm not a fucking stalker. I just went to the museums when I knew you were going to be there. I wasn't going to follow you around and take notes about what kind of cereal you like."

"Then, how did you know about Dean?"

Meg stared at him like he was an idiot, "The paintings, moron."

It was still going over his head and Meg rolled her eyes, "Dean was in almost every one of them. I'd seen a picture of him from Alistair and I saw him hanging around him when we were teenagers. I knew what he looked like."

Castiel blushed slightly, thinking no one would had ever figured that out, "But I never drew him outright. It was either just his eyes or-"

"His freckles," Meg continued, "or his bowlegs or his golden hair or his clothes. May have fooled everyone else, but it didn't get by me. Just the eyes were pretty obvious or that reoccurring shade of green. I'm pretty smart, you know."

Meg chuckled at his expression and she strolled over to the couch, "Anyway, I never told Azazel much. Just that you were in love with Dean and that you were an artist. Pretty much what anyone could have figured out."

Castiel walked over to the couch and sat beside her. She turned her head and smiled at him, "See, Clarence? I'm not such a bad girl."

He narrowed his eyes at her, still feeling doubt, "My apartment?"

She frowned and shook her head, "No, that wasn't me. That was Ruby's craftwork. A plus psycho original. Bitch is totally bat shit crazy, almost as much as Azazel and she's his second in command after Abaddon. Which is way above my pay grade, so I couldn't do anything to stop her if I had wanted to."

Castiel believed her, but still had trouble believing Meg was on his side. There had to be more reason than simply saying Why not? "Why do you want to help me, though? I'm sure you can easily just go out the front door without any trouble."

Meg looked away from him, "I really am a fan of your art. But that's all it had been the first couple of months. I wasn't willing to do half of the shit that I am now. But then…"

Meg trailed off, not finishing her sentence. Her smirk left her face and she looked pissed off as she glared at a bookshelf. Castiel was about to prompt her to continue, but then she turned to him, "You saved me, okay? That's all you need to know."

Her eyes returned back to the wall as she bit the inside of her cheek. Castiel tried to think about what she could be referring to, but he couldn't pull a memory up from before he met her at the art show. "Meg, I don't know what you're talking about."

She laughed humorlessly, "Of course you don't." She muttered to herself, "While I can't seem to forget about it," but Castiel was sure he wasn't supposed to have heard that part.

She faced him again and her eyes searched his face for something. Disappointment flashed across her face, when she didn't find what she was looking for. She sighed, "It was after one of your art shows. I almost walked in front of a bus, but you pulled me back right before it would've hit me."

Meg's eyes willed him to remember, but Castiel couldn't recall ever doing that, not that he was going to deny it. "You don't seem like the type to give your life to someone who saved you from an accident."

Meg closed her eyes for a minute, before saying, "It wasn't an accident, though."

"But-"

She cut him off, "I wasn't carelessly stepping into traffic like some dumb bimbo on her cell phone. I meant to do it."

Castiel stared at her in shock and she broke eye contact, "I was pissed off and tired. I didn't want to do this anymore. Live this kind of life, it seemed pointless. Then, you pulled me back and I don't know. I didn't think anyone would care if I did it and then this random stranger who was practically on my gang's hitlist stopped me. You made sure I was okay and told me to be more careful. I'm not much on faith, but it seemed like a sign. The world telling me to step back and rethink some things."

She looked back up at him and stood up from the couch. She made a face at him, "Aw, Clarence, don't get all mushy on me now."

Castiel didn't respond, not really knowing what to say. She arched an eyebrow at him, her smirk back in place, "Any more questions?"

Castiel was about to ask how she planned on getting them out of here, when something hit him, "Wait, you said Ruby burned down my apartment?"

Meg nodded, "Yeah, why?"

"Blonde girl? Looks like Kate Cassidy?"

Meg gave him a weird look, "Yeah, you know her?"

Castiel nodded thinking of the waitress that got Sam hooked on drugs, "She was friends with Sam in high school. I met her a couple weeks ago."

Meg shrugged, "Ruby's always been pretty fanatical about doing whatever Azazel wants her to. She probably got close to Sam to get close to Dean or to use him as leverage if needed. She loves Azazel's order of things. She thinks he's the reincarnation of Satan or something. Like I said, the bitch is pyscho."

Castiel stored the information away for later, trying not to wonder who else was in the Winchesters' lives that had been put there by Azazel. "Meg, how are we getting out of here?"

She grinned at him, "Believe it or not, but I've got a plan that I think even you would approve of, Clarence."