Dean knelt at the foot of the grave, running his fingers over the faded grass. Beneath it he could sense the dog-tags Sam had buried there long ago, their father's dog-tags. Stronger still was an achingly familiar "presence" of sorts – that of himself. Someone, Sam or maybe Bobby, had returned to scatter the ashes of Dean's corporal body here too.

When he was alive Dean would have never admitted to ever feeling lonely. In truth, he had always had some sense of it. It terrified him. The brief amount of time he'd spent without either his father or brother at his side had been unbearable. He'd sold his soul to avoid it, never realizing that loneliness and despair were part and parcel of Hell's vacation package. Hell taught him many things, most of them bad, but it also honed his ability to deal with loneliness, and that, ironically, made him a good angel.

Angels were lonely beings. They could look but not touch. They could feel, but most of the time could not express, entrapped in a perpetual log jam of emotional turmoil from which there was only one escape – disobedience, a fall from grace. If being an angel was lonely, being a dispossessed angel was much, much worse. To combat temptation, angels kept busy and tried not to think for, or about, their selves.

Dean had always buried his emotions in work. Work prevented him from dwelling too much on the things that hurt him, and longing for the things he knew he could never have. Even when he wasn't on the job he was "working." He spent his spare time tending to his tools of the trade – his weapons, his car – or charming his way into someone's bed. If ladies were unavailable, Dean played pool or poker, earning the money that kept gas in the Impala and food in his own belly. Leaving humanity behind and becoming one of God's worker bees, hadn't been much of a transition.

The only thing Dean found himself really missing was Sam – his brother, his best friend and confidant.

He hadn't been exaggerating when he described his job in Heaven as "WalMart door greeter." Dean ushered newly arrived souls toward their destinations, and on rare – very rare – occasions had to keep order when something or somebody went awry. Even for an angel he was lonely. He performed his duties alone, and had never been accepted by his fellows. They shunned him, knowing his past. It was that spirit of camaraderie he'd had with Sam that Dean missed. He missed brotherhood, and feeling needed. Together he and Sam could do anything, including putting a stop to the Apocalypse.

Sometimes Dean wondered if Sam weren't barred from Heaven not because of Azazel's taint, but to keep him as far away from Dean as possible. Heaven and Hell both knew how dangerous they could be together.

It should have been Sam wearing the wings though, not Dean.

Every time Dean pointed a new soul toward the Pearly Gates he thought about Hell. He couldn't stop himself. In Hell he had also been assigned to new arrivals, but his duties were not so benign, nor had his own torture fully ended. Alistair gave him souls who were simply victims of their own folly – those who, like Dean himself, had made deals with demons to save a loved one. None of them were truly evil - none of them deserved what they got. Dean couldn't even rationalize what he did.

Kneeling at the foot of his mother's grave, Dean curled his fingers into the cool earth, and squeezed his eyes shut tight. He could still recall his first victim quite clearly. It had been the spilling of her blood that broke the first of the sixty-six seals set upon Lucifer's prison door. He had been fresh from a tutorial from Alistair and bitterly resigned to his duties, convinced that inflicting agony upon others would make the memories of his own torture bearable. Work, he needed work to make him forget. The only work available in Hell was that of torturer.

She'd been a young mother who had made a deal to save her infant son ten years earlier. The boy lived and thrived, and she'd raised him to be the best he could be in the time she had remaining. On the eve of his tenth birthday the Hell hounds came. Her husband and son would later assume she'd been killed when she walked in on a burglary in progress.

Upon her descent into Hell she'd wound up bound in iron shackles and strapped spread eagled upon a slanted wooden table.

Don't. Don't think about this, don't…

Dean had taken his time, not stalling so much as he had been prolonging her terror. He had a job to do. He'd turned off compassion. He'd smothered guilt. Those things had only brought pain, and he was done with pain.

At least, he was done with his own pain.

He cut off her clothing first, piece by piece. Nudity increased vulnerability, produced fear – God had given torturers that tool when he'd cast humankind from the Garden. She had begged for mercy the entire time but Dean had ignored her pleas. He'd popped the buttons from her shirt one by one, and pulled it away from her chest with the tip of his knife, exposing her skin. In doing so he'd accidentally nicked her and drawn blood. A crimson spot no bigger than the head of a pin rose to the creamy white surface of her left breast….

And thus a righteous man, drawing blood in Hell, shattered the first Seal.

It had also been the nail in Sam Winchester's coffin.

The fluttering of ethereal wings broke through the screams echoing through Dean's mind, interrupting the memory before it went on any further. Dean had never gone into any specific details about Hell to Sam. Anna, wherever she was, knew some things, but not everything. Only Castiel, who had been the one to finally break through Hell's forces and free him, had any real perception of what Dean had done.

He looked up at Castiel with tears in his eyes. "What do I have to do to save him, Cas?"

Castiel appeared sympathetic. On any other angel the expression would have been patronizing, Castiel was Dean's friend before he'd been his superior. The sentiment was genuine.

"I don't know," Castiel said. "But Dean, your purpose here is not to save Sam. Those were not your orders."

"I can't let him go to Hell, Cas. I can't." Dean rose to his feet. "Not when I know…."

Castiel reached out and grabbed him by the arm. "Dean, listen to me. Listen to me as your superior and as your friend. Whatever you choose to do about Sam, I will not stop you, but remember your orders. Do not fail to accomplish your assigned tasks. It is vital, perhaps more so than any of us know. Ruby's child is a danger that must be eliminated."

"Cas…"

"Don't screw this up, Dean."

"Like I usually do?" Dean asked, jerking his arm out of the angel's grasp. "Why in the hell didn't you assign someone else to this one, huh? Why use me?"

"I have my orders too," Castiel said quietly, and abruptly vanished as quickly as he'd appeared.

Hurt, frustrated, grieving, Dean picked up a rock and threw it as hard as he could in the direction in which Castiel had vanished. He knew he would not disobey his orders, but afterward...

Dean would find a way to save Sam, even if he had to go back to Hell himself.

Evan's pain blocking had stopped working. The constant, nagging pain that had dogged him for the past five years had come back, and worse than before. It was reminiscent to the pain he used to feel when his abilities first manifested, when he'd be knocked flat by visions of things that were to come – usually deaths. The only difference was that when the vision was over, the pain would go away. This pain never went away. Sometimes it felt as if his head were surrounded by a helmet made of knives, all of them stabbing at him in rapid succession.

"Have you eaten anything lately?"

Sam started. He thought he'd gotten used to the angel's abrupt comings and goings – apparently not. He glanced quickly over at the passenger's seat to confirm Evan's presence there.

"Coffee."

"I meant food."

"I know what you meant. I figured you'd know what I meant." Sam said. "No. I haven't. The medication I take makes me sick. I can't afford to spend money on food that's just going to come back up again."

The scowl on the angel's face deepened. "Jesus, Sam…" he murmured.

"Won't you get in trouble upstairs for that kind of language?" Sam asked.

Evan didn't answer, instead he said, "Ruby's on the move. She left Toronto two days ago. Cas thinks she's headed for Saginaw."

"Damn, that means word got back to her."

"Or she's been doing some scrying herself. We need confirmation."

"You know, I've wondered about that from the get go. I can't believe a couple of angels can't locate one demon running around on Earth."

"She's good." Evan shrugged. "She's an old witch, and the one who taught her was even older. There's a lot more to her than just hex bags and kinky sex."

Sam shot him a quick glance. He'd noted back at the motel that Evan's mood seemed to have radically changed from the quirky smart-ass he'd been when he'd first showed up. He seemed distracted and darkly moody – which was more Sam's bag. Something had set the angel off, something he was keeping from Sam.

Instead of grilling him, however, Sam decided to back off instead. Habit, he supposed. Dean had always been one to internalize, and over the years Sam had grown adept at getting him to open up when he didn't necessarily want to open up. You couldn't push him. The more you pushed Dean the more he shut down and shut up.

"I know Ruby saw the Black Plague as a child. She told me," Sam said. "So how old was her mentor?"

Evan grunted softly. "You're an educated man. Let me give you a hint." He turned toward Sam with a wry look. "Ruby's mentor was named Nimue."

"Nim…" Sam knit his brows. He'd lost a few brain cells after the stroke, and sometimes the knowledge he retained took a while to find. This, though, came to him immediately. "Wait…the Nimue?"

"Yep," Evan replied. "She made that knife you're carrying. It's related to another weapon she's famous for."

"You're shitting me?"

"I'm an angel, I don't shit."

"Funny."

"Yeah," the angel said quietly. "Your brother has the dubious honor of being killed by Excalibur's second cousin twice removed." His tone turned bitter. Sam heard him mutter under his breath: "Shoulda got a freakin' tee shirt."

Sam drove on, quietly absorbing this information, information that made him understand what they were setting themselves up against. Ruby was far more dangerous than he'd ever realized. After a moment he asked, "Whatever happened to Nimue?"

"She died," Evan said bluntly.

"How?"

He felt the angel's stare. Sam turned to meet his gaze, and something in it made him shiver. It was frank, accusatory, and unforgiving.

"There are only two people alive who know the answer to that question," Evan said quietly. "One is Ruby – if you can even consider her alive. The other is the man who killed her." He looked away out the window. "She had more than one name you know. In some versions of the story she's called Viviane, in others, Elaine, but her real name was…."

"Lilith," Sam interjected. His voice was rough. "Nimue was Lilith."

Out of the corner of his eye he saw Evan's gaze go from the window to his hands, his head bowed almost as if he were praying.

"Your tainted soul is just a convenient excuse. Heaven is scared of you Sam. You killed one of the most powerful she-demons in history. You stuffed Lucifer back into jail. The very idea that you might get in makes the big-wigs upstairs shit their pants."

"So I've been banned."

"You've been banned."

"Nice to know."

"For the record, I think it sucks," Evan said sourly. "You deserve better."

Sam couldn't disagree with that. He'd done a lot of things wrong, made a lot of mistakes, but he'd tried damn hard to make up for it. The bottom line remained – he'd been dealt a bad hand from the very beginning. He'd fought it though, fought it with everything he had. He couldn't be held entirely responsible for his failures given his dark opposition, and in the end he'd made the right choice. That should mean something.

Apparently, it didn't.

"Does Dean know?" Sam asked. "Does he even remember?"

"Remember…?"

"Me, himself, being human."

"Oh. Yeah. He talks about you a lot."

"I'll bet," Sam said wryly.

"All good," Evan assured. "He misses you."

Sam repeated his first question after taking a moment to compose himself. "So does he know," he asked roughly, "Does he know about me, that I'm going to Hell when I bite it?"

"Yes."

"I wish he didn't."

"They say in time everyone forgets."

"Ruby didn't," Sam said quickly. "She told me it was more denial than anything else. Those who want to forget do, and those that don't, don't." He gave the angel a quick look. "Dean won't forget."

"So both of you are punished," Evan said softly.

"And why is that exactly? What did we ever do to deserve the shit we got, other than being freaking born in the first place?"

Evan didn't reply, but then the question had been halfway to rhetorical anyway. Sam could sense something brewing beneath the angel's surface without resorting to any psychic tricks. A cautious little probe, however, confirmed his suspicions. Evan was upset about something, and that's all Sam caught before the angel realized what he was doing and shut him down.

"I felt that." Evan said coolly. "Man, Sam. You've got balls. Trying to psychically screw with an angel? That's exactly why they don't want you in Heaven."

"So I've got nothing to lose do I?" Sam shot back in a similar tone. "You want to tell me what you're keeping quiet about?"

"Not particularly."

"If it's regarding the case I have a right to know."

Evan was obviously reluctant.

"Aside from the fact that it's bugging the crap out of you," Sam added. When Evan remained silent, he continued. "You're different," he said. "I got that right away. The younger generation always thinks they know it all, always want to strike off on their own to prove it – I know, I was there once. You've already flirted with disobedience by getting me involved in your assignment. You follow orders, but don't necessarily like them, and you're always trying to come up with a loophole." He nodded. "Yeah, I was just like that."

"You would have been a good attorney," Evan chuckled.

"No, I would have been a shitty attorney, because I have a heart. I've been screwed up, and screwed over all my life, and yeah, I admit I'm pretty bitter right now, but I'll still keep going and I'll still try to do what's right. If whatever you're sitting on is related to this case, I have a right to know, orders or no orders, so spill it or I'll dump your feathered ass out on the side of the road and go to Saginaw on my own – and don't think I don't have ways of keeping an angel off my back. If Ruby can do it, so can I."

"We're not hunting Ruby," Evan said bluntly. "We're hunting her kid."

Sam had to look to see if he were joking. From the grim look on his face – he wasn't.

"Her kid?" he repeated. "Seriously?"

"Yes."

"From when she was human?"

"From five years ago."

Almost unconsciously, Sam stomped his foot down on the brakes, bringing the Impala to a sliding, screeching halt in the middle of the road and nearly putting Evan through the windshield. The angel seemed to have expected this kind of reaction. He braced himself and avoided cracking his vessel's skull.

"I'm guessing you did the math," Evan said after the car came to a complete halt. He glanced behind him. "I think you left half the tires on the pavement back there."

"Demons can't get pregnant." Sam felt his chest tighten. His vision swam, and memories of his time together with Ruby flooded his mind. He'd used protection – hadn't he? Of course if Ruby wanted to get pregnant she would have had no trouble sabotaging things. "They can't get pregnant," he repeated.

"Ruby did. Apparently you're special."

"No." Shaking his head, Sam stared out the window, his hands clenched in a white knuckled grip around the steering wheel. "No. I can't…"

"You can, and you did, and now the little bugger has Heaven's collective underpants in a knot." Evan glanced on the rearview mirror. "Sam if you don't start driving or pull off the road, the next semi that comes over that hill is going to leave us all over the pavement."

"I was careful."

"Not careful enough. Sam…"

Sam's stomach churned. He felt as if he were going to be sick.

I have a kid.

I have a half-demon kid.

"Oh my God."

"SAM!"

"Shit!" Sam jerked the wheel and hit the gas, moving the Chevy off onto the berm just as a dump truck came barreling over the hill behind them. It breezed by the driver's side door with only inches to spare, the angry driver blasting the horn as he went past.

"Sam you need to calm down," Evan said breathlessly.

"Calm down?" Sam asked, fixing him with a hard look. "Calm down? You just dumped on me the fact that I not only have a kid out there, but it's half-demon and we're hunting it!"

"Him."

"What?"

"It's a boy. We're hunting him."

"Oh, well thanks for clearing that up," Sam said bitterly.

Evan sighed, and there was no mistaking the remorse in his tone. "I can only say 'I'm sorry' so many times…"

"You're asking me to kill my own son."

"I asked you to help me find Ruby. That's all. You can still bow out."

"And let you kill my son?" Sam stared at his companion, and in Evan's expression he saw a reflection of the turmoil going on inside his own head. "Could you?"

"It's not human," Evan said quietly. "It's an abomination, a wild-card, and it can undo everything, Sam. Ruby has the key to Lucifer's cage in her hand. If he gets out again, there won't be anyone who can stop him this time." He met Sam's gaze unwaveringly. "If this kid lives, Hell will rise."

Sam looked away. Physical pain was nothing compared to what was now stabbing him mercilessly through the heart. "They said that about me once."

"And maybe if you raised your son the way your father raised you, things would be different. This boy was raised by a demon, a demon just pissing herself to get back in Lucifer's good graces. He won't turn the tables on them like you did. He'll throw open the doors to Hell and say 'come on in.'" The angel's voice softened to a barely audible whisper. "You can't save him, Sammy. It's too late."

Without replying, Sam turned the car back onto the road. He got the impression that Evan was surprised, but regardless of what they would do when they got there, the first step toward making that decision was actually getting to Sagniaw in the first place.

"Someone should have told me and maybe it wouldn't be too late."

"We didn't know."

"Riiight.

"I swear, Sam. Me, Castiel, those of us who would have told you, weren't in on the secret and I'm not even sure the top dogs knew until recently.

Sam scowled. "Why would you have cared? I don't even know you. We just met."

"I…I've heard Cas talk about you, your brother, the things you've done." The angel smiled, looking ever-so-slightly smug. "You're heroes."

Sam looked away with a grunt. "Heroes and whores – the only difference is that whores get to choose who fucks them over, and the pay is a hell of a lot better."