On the Head of a Pin Part 1

Sam was driving.

"Ruby will meet us outside Cheyenne." Sam said. "She's been tracking some leads. I know she's not exactly on either of your Christmas lists, but if she can help us get to Lilith—

"Hey, Sam, work with Ruby, don't. I don't really care anymore." Angela said.

"What's up with you Angie?" Sam frowned.

"Pamela didn't want anything to do with this and we dragged her back into it, Sam." Angela replied.

"She knew what was at stake." Sam shrugged.

"Oh yeah." Angela sneered. "Saving the world. And we're doing such a damn good job of it."

"Angie—

"I'm tired of burying friends, Sam." Angela muttered.

"Look, we catch a fresh trail—Sam started.

"And we follow it, we know, Sam." Dean replied. "Like Angie said, she's getting tired. And frankly so am I."

"Well, get angry." Sam said.

~/~\~

They entered the room.

"Ah, home crappy home." Dean said.

Sam flipped the lights.

"Winchester and Winchester and Morgan." Uriel said.

Uriel and Castiel were waiting inside the room.

"Oh come on." Dean groaned.

"You are needed." Uriel said.

"Needed?" Dean asked. "We just got back from needed."

"Now, you mind your tone with me." Uriel warned.

"No, you mind your damn tone with us." Dean retorted.

"We… we just got back from Pam's funeral." Angela said softly. "Please."

Dean nodded. "Pamela. You know, psychic Pamela?" Dean asked. "You remember her. Cas, you remember her. You burned her eyes out. Remember that? Good times. Yeah, then she died saving one of your precious seals. So maybe you can stop pushing us around like chess pieces for five freaking minutes!"

"We raised you out of hell for our purposes." Uriel replied.

"Yeah, what were those again? What exactly did you want from me?" Dean asked.

"Start with gratitude." Uriel said.

"Oh." Dean nodded.

"We know this is difficult to understand." Castiel said.

"And we," Uriel started, giving Castiel a significant look. "Don't care. Now, seven angels have been murders, all of them from out garrison. The last one was killed tonight."

"Demons? How are they doing it?" Angela asked.

"We don't know." Uriel replied.

"I'm sorry, but what do you want us to do about it?" Sam asked. "I mean, a demon with juice to ice angels has got to be out of our league, right?"

"We can handle the demons, thank you very much." Uriel retorted.

"Once we find whoever it is." Castiel cut in.

"So you need our help hunting a demon?" Angela raised a brow.

"Not quite." Castiel shook his head. "We have Alastair."

"Great." Dean shrugged. "He should be able to name your trigger man."

"But he won't talk." Castiel replied. "Alastair's will is very strong. We've arrived at an impasse."

"Yeah, well, he's like a black belt in torture." Dean said. "I mean, you guys are out of your league."

"That's why we've come to his student." Uriel replied. "You happen to be the most qualified interrogator we've got."

Dean looked down.

Angela glared and walked up to Castiel and Uriel. "You can't as him to do this!" she exclaimed. She looked at Castiel. "Cas, please, you, you can't." she said.

Cas' eyes flickered to the ground and then back to her. "Angela, I'm sorry." He whispered. "Dean is our best hope."

"No. No way." Dean said. "You can't ask me to do this, Cas. Not this."

Uriel walked up to Dean. "Who said anything about asking?"

Sam and Angela looked around. The room was empty.

"Dammit!" Sam yelled.

~/~\~

Alastair was visible through a window in a door, chained to a hexacle standing in the middle of a devil's trap.

"This devil's trap is old Enochian. He's bound completely." Castiel said.

"Fascinating." Dean turned away from the door. "Where's the door?"

"Where are you going?" Castiel asked.

"Hitch back to Cheyenne, thank you very much." Dean walked past Uriel, then stopped: Uriel was blocking his path.

"Angels are dying, boy." Uriel said.

"Everybody's dying these days." Dean retorted. "And hey, I get it. You're all-powerful. You can make me do whatever you want. But you can't make me do this."

"This is too much to ask, I know. But we have to ask it." Castiel said.

Dean watched Castiel for a moment, then turned back to Uriel.

"I want to talk to Cas alone." Dean said.

"I think I'll go seek revelation." Uriel replied. "We might have some further orders."

"Well, get some donuts while you're out." Dean said.

Uriel laughed. "Ah, this one just won't quit, will he? I think I'm starting to like you, boy."

Dean watched Uriel vanish. "You guys don't walk enough. You're gonna get flabby."

Castiel didn't react.

"You know, I'm starting to think junkless has a better sense of humor than you do." Dean sighed.

"Uriel's the funniest angel in the garrison. Ask anyone." Castiel replied.

Dean walked up to Castiel. "What's going on, Cas? Since when does Uriel put a leash on you?"

"My superiors have begun to question my sympathies." Castiel said.

"Your sympathies?"

"I was getting too close to the humans in my charge. You and Angela. They feel I've begun to express emotions. The doorways to doubt. This can impair my judgment."

"Well, tell Uriel, or whoever… you do not want me doing this, trust me."

"Want it, no. But I have been told we need it."

"You ask me to open that door and walk through it, you will not like what walks back out."

"For what it's worth, I would give anything not to have you do this." Castiel replied.

Dean closed his eyes.

~/~\~

Dean wheeled a loaded cart covered with a cloth into the room where Alastair was imprisoned. Alastair watched Dean enter, grinned, and started to sing, moving within the chains almost as though he were dancing.

"Heaven, I'm in heaven, and my heart beats so that I can hardly speak." Alastair sang. "I seem to find the happiness I seek, when we're out together dancing cheek to cheek…"

Dean pulled the cloth off the cart, revealing an assortment of torture implements. Alastair laughed. Dean ignored him.

"I'm sorry. This is a very serious, very emotional situation for you." Alastair said. "I shouldn't laugh, it's just that, I mean, are they serious? They sent you to torture me?"

"You got one chance. One." Dean replied. "Tell me who's killing the angels. I want a name."

"You think I'll see all your scary toys and spill my guts?"

"Oh, you'll spill your guts, one way or another." Dean replied. "I just didn't wanna ruin my shoes."

"Oh, yeah." Alastair said.

"Now answer the question." Dean pressed.

"Or what? You'll work me over?" Alastair asked. "But then, maybe you don't want to. Maybe you're, ah, scared to."

"I'm here, aren't I?" Dean asked.

"Not entirely. You left part of yourself back in the Pit." Alastair replied. "Let's see if we can get the two of you back together again, shall we?"

"You're gonna be disappointed." Dean walked over to the cart.

"You have not disappointed me so far. Come on. You gotta want a little payback for everything I did to you. For all the pokes and prods. Hm?"

Dean was impassive.

"No?" Alastair asked. "Um… how about all the things I did to your daddy?"

Dean's head came up.

~/~\~

Sam opened the door for Ruby. Angela sat on one of the motel beds.

"I can still smell them." Ruby said in disgust. "Seriously, Sam, I'm not exactly dying to tangle with angels again."

"We need you to find out where they took Dean." Sam replied.

"Not sure if I see the problem." Ruby said. "You know they have Alastair strung up six ways from Sunday. Dean cuts himself a slice, Al's reduced to a quivering heap, and the good guys get the goods. What's wrong with that?"

"He can't do it." Sam said.

"Look, I get it. You and Angie don't want him going all torture master again."

"No." Sam shook his head. "I mean, he can't do it. He can't get the job done. Something happened to him downstairs, Ruby. He's not what he used to be. He's not strong enough."

"And you are?" Ruby asked.

"I will be."

Angela stood up, having enough of this. "Don't you get it Sam?" she asked, walking over to him.

Sam frowned and looked at her, confused.

"Dean's going to torture." Angela continued. "These angels are forcing Dean to the thing he has nightmares about!" she exclaimed. "So, please, pull your head out of your ass for one god damned moment and stop worrying about who's stronger than the other, and start worrying about how we can get Dean back so he doesn't have to do this!" she yelled.

Sam went wide eyed at swallowed thickly.

~/~\~

"I had your pop on my rack for close to a century." Alastair said.

"You can't stall forever." Dean replied.

"John Winchester." Alastair mused. "Made a good name for himself. A hundred years. After each session, I'd make him the same offer I made you. I'd put down my blade if he picked one up."

"Just give me the demon's name, Alastair."

"But he said nein each and every time. Oh, damned if I couldn't break him." Alastair continued.

Dean took off his leather jacket.

"Pulled out all the stops, but John, he was, well, made of something unique." Alastair said. "The stuff of heroes. And then came Dean. Dean Winchester. I thought I was up against it again."

Dean drank from a bottle of something probably alcoholic.

"But daddy's little girl, he broke. He broke in thirty." Alastair said. "Oh, just not the man your daddy wanted you to be, huh, Dean?"

Dean put down the bottle.

"Now." Alastair smirked.

Dean picked up a jigger and filled it from a large bottle of water that had a rosary in it.

"Now we're getting somewhere." Alastair said. "Holy water? Come on. Grasshopper, you're gonna have to get creative to impress me."

Dean looked up finally. "You know something, Alastair? I could still dream. Even in hell. And over and over and over, you know what I dreamt? I dreamt of this moment."

Alastair began to look nervous. Dean picked up the needle.

"And believe me, I got a few ideas." Dean said.

Dean filled the needle from the jigger, sprayed a little water from it, and went over to Alastair.

"Let's get started." Dean smirked.

~/~\~

"Oh, man. Ooh." Alastair groaned.

Dean put the needle back on the cart with his other tools. "Let me know if you want some more. There's plenty left."

"Go directly to hell." Alastair replied. "Do not pass go, do not collect two hundred dollars."

Dean smiled.

~/~\~

Ruby chanted, holding a lit candle to the corner of the map. Sam and Angela watched the fire spread around the edges.

"Relax." Ruby said. "The fire is our friend. Besides, the only part of the map we need is the 'where's Dean?' part. Out."

The flames vanished. The map was charred to unreadability; a small circle in the middle was untouched.

"There. Dean's there." Ruby said. "It's a good thing angels aren't concerned with hiding their dirty business. Not used to being spied on. I mean, who'd be stupid enough to try?"

"Ruby, it's been weeks. I need it." Sam said.

Angela glanced over at him.

"You don't seem too happy about it." Ruby replied.

"You think I wanna do this?" Sam asked. "This is the last thing I—he sat on the bed. "But I need to be strong enough."

Ruby straddled Sam's lap and Angela took this as her cue to leave the motel room.

"It's okay." Ruby cooed. "It's okay, Sammy. You can have it."

Ruby kissed Sam. She pulled a knife from an ankle sheath and cut her arm, drawing blood. Sam drank it straight from the vein. Ruby stroked his hair.

"It's okay, Sam." Ruby smirked.

~/~\~

Angela closed the motel room door and walked out to the parking lot. She ran a hand over her face and sighed, looking up at the sky.

"Cas?" she asked. "Um, I, I know you're most likely busy at the moment, and I know you and I haven't exactly been on the best of terms... we disagree and you probably don't like me all that much, but uh, I, I could really use someone to talk to right now." She prayed.

She swallowed thickly and waited for a few moments before she heard the familiar flutter of wings.

"What do you wish to talk about, Angela?" Castiel asked, walking over to her.

"Sam." she replied. "I… I can't talk to him about this and Dean has so much on his plate already, and I... I'm sick of holding all this in." Angela replied. She ran a hand through her hair. She glanced back at the motel room door.

Castiel nodded. "Well, I appreciate that you decided to talk to me instead of keep it in." Castiel replied. "And for the record, I do like you. We just tend to have... disagreements."

She smiled softly at his last comment, then let out a small sigh. "To be perfectly honest, I'm not mad at Sam anymore for cheating on me. I'm not. I'm not even pissed at Ruby anymore. Sure, I hate the bitch, I think she's manipulative and using Sam, but that's not the poin. I'm not mad at either of them to be perfectly honest." She whispered. Tears suddenly pricked at her eyes. "I'm just… I don't even know how to describe it, Cas…"

She sighed and looked up at Castiel.

"I just…." She started. "What does she have that I don't?" her voice cracked. "Besides demon blood, of course." She murmured. "But, what makes her better than me? Is she prettier? Sexier?" she wiped away a few stray tears. "What does she have that caused Sam to throw away our whole relationship? And the worst part is, I still love him dammit. After he threw it all away, I still love him." she said. She shook her head. "I'm sorry, I shouldn't be dumping this on you, not now…"

"Angie…" Castiel whispered. He gingerly took her face in his hands and she looked up at him, slightly confused by the action. "Angela Morgan. You are a treasure. You are beautiful, you are smart, you are kind, and you are willing to do so much for people." Castiel smiled a bit.

Angela felt new tears prick her eyes. Not tears of sadness, no, these were different. "Cas…" she whispered.

"And it's okay to still have feelings for him." Castiel assured. "I mean, that is why you started a relationship with him in the first place. Because you loved him." He said. "But that doesn't mean you can't move on. He may always have a place in your heart, but you still deserve a chance at happiness." He murmured.

Angela smiled softly at the angel. "Wow, Ca-Cas, I had no idea that you had such a way with words." She murmured. "Thank you. Really, thank you so much." She said. She gave him a quick kiss on the cheek.

Castiel smiled softly at the gesture. He sighed. "Now, I'm afraid I do have to return to where Dean is. You are free to join me. Of course, we won't be in the room with him, just outside."

She thought for a moment and nodded. "Okay. Okay, yeah, I'll go with you."

~/~\~

Dean held Ruby's knife. Alastair looked at it and laughed.

"That's that little pig-poker." Alastair said. "I wondered where it went."

Dean dipped a ladle into a bowl of what is presumable holy water and poured it over the blade.

"Do you really think this is gonna fix you? Give you closure?" Alastair asked. "That is sad. That's really sad. Sad, sad."

Dean approached Alastair, watched for a moment, and stabbed him. There was a sizzling sound.

"I carved you into a new animal, Dean. There is no going back."

"Maybe you're right." Dean shrugged. "But now it's my turn to carve."

"No!" Alastair yelled.

An unseen hand began to turn a faucet. It began to drip, right onto the chalk of the devil's trap on the floor.

~/~\~

Castiel and Angela were in the next room. They listened to Alastair's groans. The lights flickered, catching their attention; the bulb exploded. Anna appeared behind Castiel and Angela.

"Anna." Castiel said.

Angela turned her head to look at Anna.

"Hello, Castiel. Angela." Anna greeted.

Castiel turned to look at her, and Angela did the same.

"Your human body—Castiel started.

"It was destroyed, I know. But I guess I'm sentimental. Called in some old favors and…"

Alastair became slightly more audible.

"You shouldn't be here." Castiel replied. "We still have orders to kill you."

"Somehow I don't think you'll try." Anna said. "Where's Uriel?"

"He went to receive revelation." Castiel said.

"Right." Anna nodded.

~/~\~

Dean pulled the knife out of Alastair, whose head fell forward. Dean tilted it back up, ignoring the blood. Alastair laughed.

"Now it's your professionalism that I respect." Alastair said.

Dean turned away, disgusted. Alastair spit blood.

~/~\~

"Why are you letting Dean do this?" Anna asked.

"He's doing God's work." Castiel assured.

"Torturing?" Anna scoffed. "That's God's work? Stop him, Cas, Angela, please. Before you ruin the one weapon you have."

Angela looked at her feet. "I want to stop him Anna, I do." She whispered. But, she knew it wasn't in her hands.

Castiel looked at Angela and took her hand in his comfortingly. "Who are we to question the will of God?" Castiel asked.

"Unless this isn't his will." Anna said.

"Then where do the orders come from?" Castiel asked.

"I don't know. One of our superiors, maybe, but not him."

~/~\~

Dean splashed Alastair in the face with holy water; it steamed and sizzled. Alastair gargled.

"Who's murdering angels?" Dean asked.

Alastair choked.

~/~\~

"The father you love. You think he wants this? You think he'd ask this of you? You think this is righteous?" Anna said.

Castiel couldn't meet her eyes.

"What you're feeling?" Anna asked. "It's called doubt."

~/~\~

Alastair screamed and chocked. Dean poured out more holy water, splashed Alastair in the face, and watched him sizzle.

~/~\~

Anna touched Castiel's free hand.

"These orders are wrong and you know it." She said. "But you can do the right thing. You're afraid, Cas. I was too. But together, we can still—

"Together?" Castiel yanked his hand away from Anna. "I am nothing like you. You fell. Go."

"Cas." Anna said.

"Go." Castiel repeated.

Anna vanished. Castiel and Angela listened to Alastair scream.

~/~\~

Alastair spit out blood and holy water.

"You're just not getting deep enough. Well, you lack the resources." Alastair said. "Reality is just, I don't know, too concrete up here. Honestly, Dean…"

Dean poured salt into another container.

"You have no idea how bad it really was, and what you really did for us." Alastair continued.

"Shut up." Dean whispered.

"The whole bloody thing, Dean. The reason Lilith wanted you there in the first place."

"Well, then I'll just make you shut up." Dean grabbed Alastair's chin.

"Lilith really—

Dean poured salt into Alastair's mouth. Alastair tried to scream.

~/~\~

Alastair spit out blood and tried to breathe.

"Something caught in my throat. I think it's my throat."

"Well, strap in, 'cause I'm just starting to have fun." Dean went back to his cart.

"You know, it was supposed to be your father."

Dean poured out more holy water.

"He was supposed to bring it on. But, in the end, it was you." Alastair continued.

"Bring what on?" Dean asked.

"Oh, every night, the same offer, remember? Same as your father?"

Dean shook the salt onto the blade of Ruby's knife.

"And you finally said, 'Sign me up.' Oh, the first time you picked up my razor, the first time you sliced into that weeping bitch…"

Dean turned to face Alastair.

"That was the first seal." Alastair smirked.

Dean did not visibly react. He walked closer. "You're lying."

"And it is written that the first seal shall be broken when a righteous man sheds blood in hell. As he breaks, so shall it break."

Dean turned away.

"We had to break the first seal before any others. Only way to get the dominoes to fall, right? Topple the one at the front of the line."

Now that Dean was not facing Alastair, his shock was visibly on his face.

"When we win, when we bring on the apocalypse and burn this earth down, we'll owe it all to you, Dean Winchester."

Dean closed his eyes, trying not to react.

"Believe me, son, I wouldn't lie about this. It's kind of a religious sort of thing with me."

Alastair noticed the dripping faucet and the broken edge of the devil's trap.

"No." Dean said. "I don't think you are lying. But even if the demons do win…" Dean looked at Ruby's knife. "You won't be there to see it."

Dean turned around. Alastair was right behind him, out of the chains.

"You should talk to your plumber about the pipes." Alastair replied.

Alastair punched Dean, who went down. Alastair grinned.

A/N: Hey guys! I hope you really liked this chapter. I did tweak the scene with Cas and Angie a bit and I'm still not entirely happy with it, but I do think it panned out rather nicely. I tried to write Cas as in character as possible, but I wanted him to be really tender with Angie. What I'm going for is that it could sort of be inferred that Cas has a little crush on Angie, but isn't fully aware on how to deal with it because 1. He's not really supposed to feel emotion, yet with her it's different and 2. She does still love Sam, so Cas isn't really sure what to do there.

So, we will get more small Cas/Angie moment in future chapters. I know there was really no jealousy factor with Sam, but I really am trying to fit it in, so just bear with me guys. :)

Don't forget to review, review, review! Love you guys!

~Emily