Sam lagged behind when they began to approach the building and Dean held back from rolling his eyes. Hadn't Sam said he would trust him? What was the point of it if he was going to-
Dean stopped that train of thought. Sam could have his reservations – Dean was sure as hell going to keep a firm hold on his suspicions of Ruby. It didn't change the fact that Castiel was back in his presence again.
Castiel's step faltered, his body seizing up, and it was Sam who grabbed and steadied him before he could fall. "Whoa, man! You okay?"
Dean belatedly grabbed Castiel's other arm to help support him, but soon both brothers' hands had been shaken off. "I'm fine. I'm just tired. The sooner we find the girl the better; go."
The look Sam shot Dean was wary, but he walked to the doors of the church at the older hunter's nod. Dean leaned close to Castiel when his brother was a few feet away. "Castiel, you need to sit this one out? We can handle picking up some chick, but if you clock out on us-"
"I'll be fine."
Dean didn't pretend to be satisfied with Castiel's answer, but he decided to let it slide. Castiel was right, they had to find Anna soon, before the other demons could get to her. They'd already been too close for comfort and Dean would be much happier if he knew the girl was out of their grasp.
The two caught up to Sam quickly, and from there the trio entered the building easily enough. The front door was unlocked, and Sam and Dean were cautious, peeking in and assuring that no one was inside before slipping through the doorway. Castiel followed behind them, eyes roaming the walls.
He looked oddly in place in the church; his stillness would have been almost unsettling if Dean hadn't gotten used to it through Inias' random appearances. The angel was even more motionless than Castiel with less practice at appearing human than the demon. Castiel, from what Dean had observed, knew how to shift his weight from foot to foot every so often, to blink and look around and include so many little human nuances that the angelic warriors didn't seem to understand.
"No one's here," Sam murmured after they searched through the main floor. His voice, even as quiet as it was, carried through the empty church, Dean motioned that he had heard, and Castiel's arm came up to point. Following Castiel's direction, Dean saw the set of stairs nestled in the corner and nodded to himself.
He and Sam crossed the room to the stairs, but Castiel remained where he was. "You coming?" Dean hissed.
Castiel's head shook. "Get Milton, take her somewhere safe. There is something I have to take care of." Castiel started to walk away, but stopped and added, "Don't wait for me. I'll find you when it's safe."
Dean opened his mouth to reply, but Castiel was gone before he could even decide what to say. He scowled after the demon and Sam's hand on his shoulder focused him again.
The two of them moved fluidly together up to the second floor. The stairs, spurred on both by age and their combined weight, creaked loudly as they climbed.
An empty room with a large circular window greeted their eyes as they finished their ascent. Sunlight streamed through the colorful glass, highlighting dust motes that floated around and painting everything in faint shades of color. It was quiet.
"Anna," Sam called. "You in here?"
There was no reply, and Sam and Dean started to slowly inspect the room. Sam paused suddenly, the stop catching Dean's attention. Sam motioned towards the cluttered space in the room to the left of the large window. It was piled high with boxes and other things, blocking their view of the corner. Dean listened closely, nodding to his brother when he, too, heard the shuffling sounds coming from there.
"Anna, my name's Sam Winchester, and I'm here with my brother Dean. We were just at your parents' house; they're worried about you, and they asked us to help. It'd really help if you'd talk to us." Sam gripped the demon-killing knife as he said it, but his hand was relaxed and resting at his side. Dean was the one who crept slowly closer, ready to spring into action should the need arise.
It didn't. Before either brother got the chance to peek behind the haphazard stack, a girl's face poked out. Her hair was bright red and a stark contrast against her pale skin. Large eyes scanned the hunters quickly and efficiently under a furrowed brow.
"Did you say Winchester? The Dean Winchester?" she asked. The intense focus that she immediately placed on them was unsettling, and Dean took a subtle step closer to his brother before he replied.
"That would depend where you've heard of me before. As far as I know, I'm the real deal."
Anna Milton stood up a little straighter behind her makeshift barricade, lips pressing together. "The Dean Winchester who was in hell."
The girl didn't falter as she waited for a response; her gaze was steady, her hand still where it hung at her side. A humorless chuckle escaped from Dean's lips.
"One and only."
Anna bit her lip and the brothers watched as her eyes surveyed them both one more time.
"We don't have all day, sweetheart, we're on a bit of a schedule. We only have so long before more demons show up," Dean said after a few minutes of waiting.
Anna gasped, eyes flying wide open at the comment. "They're still following me." She sounded more resigned than anything else. Dean could recognize the tiredness in her eyes, the slight slump in her shoulders. He wished he could do more to help than just get her away, but he didn't have many more options.
"We have friends who can help you get away from the demons. But it would really help if we knew why they want you," Sam interjected, easing closer to Anna with his hands held at shoulder level.
"You don't need to treat me like I'm about to fall apart," she snapped, hazel eyes narrowing in irritation. "I'm not a damsel in distress. I probably know more about what the hell is going on than either of you."
Dean was about to respond, but the sudden screech of rage from outside brought them all to a stop. The brothers rushed to the large, circular window, Anna a quiet presence at their backs. Dean couldn't see much, but what he did see was enough to set his hair on end.
Castiel's trench coat flared by the road as the demon whirled, face contorted by a vicious snarl as he wrestled with an older man. They grappled and fought, and Dean felt his stomach sink a little when the older man – a demon no doubt – tossed Castiel aside like he was no more than a plastic bag. The smaller demon's cry, although unheard, was easy to see in the twist of his features. Dean grabbed Anna's arm as Castiel sprang back to his feet and launched himself at the other demon and began to drag her away.
"We have to go now," he said. Anna didn't protest, though she did shake off his firm hold and opted instead to walk between the brothers. They were out the door and scanning for danger in minutes.
The yard was eerily silent. Neither demon was in sight.
Dean ushered Sam and Anna out of the church and towards the Impala, hand resting on his gun even as he made his way to the car. Then there was movement and Dean was spinning to attack and he was shoved forcefully towards the car by a blur of long dark hair and intense eyes. "Drive! Now!" Ruby shouted as she climbed into the backseat next to Anna. The redhead screeched, something about Ruby's face, but Dean was frozen behind the wheel as Castiel flew into sight again.
The demon looked even worse for wear; his coat was torn and covered in dirt stains. Castiel managed to land in a roll that placed him on his feet, but he swayed as the other demon rushed him, pinned him to a tree and leaned close. Castiel grabbed at the hand on his neck.
"Dean! Drive, go! Whoever that is won't be able to keep Alastair occupied much longer!"
Ruby snapped Dean from his stupor and the hunter stomped on the gas. The Impala roared and rocketed away, and Dean saw the two men turn in the rearview mirror.
Castiel's mouth opened in some sort of shout, but Dean couldn't spare the focus to figure out what. The other demon simply opened his jaws in a howl that shook the very air.
Dean stopped only long enough for Sam to run into the Milton house and grab Anna's parents and then they were off again; he was grateful they had packed before leaving the motel - one less delay to deal with. Dean felt better once they were on the highway and putting distance between themselves and the strange demon. He didn't allow himself to feel guilty about leaving Castiel; Castiel was more than capable of keeping himself safe.
The first thirty minutes of the ride were tense and silent but for Anna fidgeting between her parents. Whenever Dean glanced at them in the rearview, the young woman was staring over at Ruby with distrustful eyes, looking almost horrified. Dean wasn't Ruby's biggest fan, he'd admit, but the demon didn't deserve a disgusted stare. The redhead settled down a bit after that, though Dean could tell she was still tense in the cramped back seat.
His thoughts, without anyone talking for distraction, wandered to Castiel as he drove. He hadn't been at the top of his game, and Dean hadn't so much as blinked when he left him behind. Even knowing that the demon would need more than one beating to break him, he still worried. Castiel had given them precious minutes to escape without Alastair – Dean made a note to find out whom, exactly, that was later – focusing on them.
Something in Dean's gut left him uneasy about the situation, but things were how they were. If they turned back now, it would only serve to get them caught. So Dean filed his concern away and focused on the tarmac that flew by under his tires as the day wore on.
Eventually, keeping in her thoughts must have proven too much, because when they were several hours out Anna blurted, "She's a demon!"
Sam was the one who handled the situation, thankfully. He was better at this than Dean, dealing with people and calming them down. "It's okay," he said, "Ruby's a friend of ours. She helps us."
"But her face-!"
Ruby grumbled something that Dean thought was "It's just a face, relax." Sam continued, "She's not like the ones that were chasing you before," and somehow that actually worked to help calm the girl down.
"Like that one at our house?" Mrs. Milton asked. Dean's fingers curled tighter around the steering wheel. Her tone was suspicious as she said, "Castle? He acted like he knew those other ones-"
"Castiel saved all our asses by hiding us," Dean said. "And he saved us again back at the church when we were getting your daughter by holding off- By holding off that other guy. Alastair."
The Impala's rumble filled the otherwise awkward silence. Dean glanced in the mirror again and saw Ruby's eyes locked on his own, dark and still.
"What?"
"That was Castiel holding Alastair off?" Something about her tone struck him the wrong way. Dean pulled onto the shoulder as Ruby leaned forward. Her hand curled uncomfortably close to his shoulder on the seat, and he leaned away even while he twisted to look at her.
"Yeah. Why, didn't you recognize him?"
Ruby shook her head. Dean would have taken great pleasure in the flabbergasted expression on her face at any other time, but right now it was anything but comforting. Sam's hand fell on his shoulder to restrain him before he even got a sentence formed in his mind.
"Why does it matter? Castiel can handle it," Dean said.
"He can handle it? Dean, did you even listen to what I said? That was Alastair he was fighting!"
Like that was supposed to make any difference? Dean didn't care who it was, even if the name was one he felt he should recognize.
Dean found himself uncomfortable under Ruby's expectant, unrelenting stare and he escaped from the Impala to pace beside it in long strides. Ruby followed him, slamming the door behind her and crowding his personal space. "Dean, this isn't some game, it's…" She stopped with her mouth hanging half-open to continue. Then her eyes blazed. "You don't remember. How can you not remember Alastair? Dean, he's… There is no way you could forget him!
"We have to go back."
Dean scrambled around even as Ruby returned to the Impala. "What?"
The demon rolled her eyes, hands on hips and expression dour. "I'll be the first to admit that Castiel and I aren't friends, and we don't like each other much, but if he's helping you then he's helping Sam, and I'm not leaving him alone fighting Alastair."
Dean rushed forward himself to hold the Impala's door closed when Ruby tried to slip back in. "Castiel's a big boy; he can make his own choices."
"Castiel would be hard pressed to match Alastair on the best of days. From what I hear he's not at a hundred percent right now. How do you think he's gonna fare?"