A/N: Thank you to all my reviewers, you've given me a lot of encouragement in the continuation of this story. I hope that a lot of unanswered questions can be resolved here as the plot thickens. Sorry, pardon the cliché. I know this has been a while in coming; the "glitch" drove me nuts. But enjoy!

Disclaimer: Supernatural and all its affiliates belong to Eric Kripke.

The demons circled their prey silently, forming concentric rings around him. Several bodies littered the field, their owners lying unconscious in the wake of having malevolent spirits removed from their forms and the man with the brilliant blue eyes turned slowly, stare trained steadily on the many who still surrounded him. There was no fear upon his face, only the same concentration that bespoke hidden power and years of experience despite his relatively young appearance.

Castiel.

The one word was spoken in a flawless, ethereal voice, resounding with authority and somehow lifted above the rest of humanity. It couldn't have belonged to any mortal alive, and yet Dean didn't find himself falling back against the tall stalks of corn, cringing and clutching his bleeding ears. Suddenly, there was a flash of light that would have blinded him had he not thrown up his arms to shield his face in time. He was knocked flat on his back but the image of what he had seen was forever sealed deep into his memory.

The moon's soft light fell upon Castiel's face, which held a myriad of emotions even though angels were supposedly not able to experience such feelings. Surprise peppered with disbelief flashed across his features, evident in the slight raising of his eyebrows and the noticeable widening of his eyes. These were quickly overtaken by a downward pull of his mouth and then a slight furrowing of his brow. There was a remarkable softening of his gaze, the likes of which Dean had never seen so plainly displayed on the angel's face before, these hints which could only connote regret.

No artist on earth, no matter how talented, could have ever managed to twist compassion and sorrow so finely in one face; no pen could have ever done justice to the description of the raw sting of betrayal he saw there. And as the angel crumpled to the ground like a marionette whose strings had just been cut, Dean saw the same brand etched into Castiel's forehead and the hunter struggled to sit up, trying to see past the swarm of demons that were now converging on their helpless victim.

As wakefulness pulled at his senses, Dean for once fought against the light of consciousness and strained his eyes, catching the sight of the lone figure that stood above Castiel's limp frame, a figure made of both darkness and light.

"Do you think we should wake him up?"

"Nah, should probably let him sleep. Boy looks like he hasn't seen a proper bit of shuteye in weeks."

Sam carefully set down the covered pie tins next to the lamp on the small table beside the couch where Dean lay draped over the cushions like a sack of flour, head lolled back against the armrest and mouth halfway open in sleep. The diner had both cherry and apple pie and since he couldn't remember which one his brother preferred, he'd gotten both.

"Hey, Bobby?"

"Yeah?" The older man looked up from where he sat pouring over a textbook that even law students would've cried at the sight of.

"You got a blanket?"

"The ijit's on top of it."

Bobby watched Sam tilt his head to the side, trying to figure out to pull the blanket out from under Dean's sprawled out form without waking him. Presently, the younger Winchester shook his head and defeat and shucked off his own flannel jacket, carefully placing it over his brother's shoulders. A smile pulled at the elder hunter's mouth and he watched appreciatively as Sam sat down in the armchair near the couch with a sigh, picking up the dissertation written by someone or other that had fallen from Dean's slack fingers. He stared at the pages for a moment, and chuckled quietly, shaking his head in disbelief.

You've got to be kidding me. Sam flipped through the pages, glancing at the messy chicken scratch of notes written in the margins. Dean was never the one to do any research, more than often not he took upon himself the duty of hustling pool or choosing the location of where they would get their next meal. And here he is annotating like a college student. Unbelievable.

He had once told Dean that there was ten times as much lore about angels as there was about anything else they had ever hunted, and they had already been through this process once before, several months ago after Castiel had first pulled Dean out of hell. Sam sighed and flipped through the pages, skimming over the copious material. He had to wonder at the reversal of everything now though, for instead of finding out how an angel could pull someone out of Hell, now what they were trying to find out was if and how it was possible to land an angel in Hell.

It would've been a near impossible task if not for Bobby's library of lore that consisted of everything that went bump in the night and apparently things that fell from Heaven too. Sam snuck a discreet look at the other, who was still reading. The way Dean had turned wide, panic-stricken eyes upon Bobby that morning when they had arrived on his doorstep had been enough to goad him into agreeing to help. He had suggested seeking out Pamela for help as well, although the idea quickly withered away when Bobby reminded him exactly how she'd gotten her eyes burned out of her skull.

What're we supposed to do? Sam shut the book and leaned his head back against the headrest, gazing listlessly up at the ceiling, slightly yellowed with age and grey-brown in some areas where Bobby had some trouble with leaks. They had been researching for nearly six hours nonstop and had yet to find anything useful or substantial.

"Find anything yet?" he asked aloud, more of an excuse to fill the emptiness of the silent room than to actually expect a response. To his surprise, the reply came filled with tentative wonder.

"Maybe." Sam stood, moving forward toward the desk.

"What is it?" He frowned at the small, block-style print and pulled the textbook closer for a better look. "Sex Diluculo ac Hora," He murmured, doing some quick and rudimentary Latin translation in his head. "Six daybreaks and hours? What does that mean?"

Bobby pointed at a graphic in the bottom left hand corner of the page. "Does that look familiar?"

Sam stared for a moment and then fumbled amongst the papers on the desk for the single sketch of the brand that Dean had drawn. He could still see his brother's face when he had touched the tip of the pen to the paper, face contorted in a mixture of confusion and pain. What had struck him the most though, was the stark fear he read on Dean's face, the fear of uncertainty and the horror of what he had seen behind closed eyes possibly coming true. It had been the face that stared back at him for days before Jessica's death, the same haunted gaze punctuated by dark circles around his eyes and the tightness of the cheeks as tension swallowed him whole. Sam remembered that face alright. It had been the face he wore days before Dean's contract expired and he hated to see it on anyone else's face, especially that of his older brother who was too self-assured and confident to be that frightened of anything.

His fingers finally grasped the sheet of paper ripped off from the memo pad at the motel's front desk and pulled it loose from all the other junk cluttering the desktop and spread the crinkled surface smooth, placing it on top of the book for a close comparison.

Perfect match.

Bobby pushed slightly away from the table exhaled deeply, taking his hat off and rubbing the back of his head. "Dean said that he saw this on the angel's forehead?"

"Yeah, like it had been burned onto the skin, branded there like the handprint on his arm." Bobby's face was grave, almost solemn and a cold, heavy feeling swelled in the bottom of Sam's stomach. "Why, what is it?" He tried to read the caption underneath the picture but it was in Latin again and this time was far too advanced for his comprehension.

"It's a part of a ritual for the breaking of another seal. Your angel…" Bobby shook his head. "To put it lightly, he's in real bad shape."

Souls flooded into Hell by the multitude each and every day, individuals of all shapes and sizes, young and old, male and female. It almost seemed as if ambassadors from each and every race and tribe on earth were being sent down into the Pit for here; there was no discrimination or division between sex, race, or whether one had been a good person or not. Here, they were all one and the same- nameless, faceless souls that screamed out identical pleas for mercy and desperation as they begged for relief in the form of a death they would never taste.

Creators of those famed post-apocalyptic movies concerning zombies and whatnot had a common theme: when Hell filled up, the dead would walk the earth. What they didn't realize was that there was always room for more in Hell. The abyss was like a deep canyon that stretched on into the depths of forever, its entrance black, gaping, and always ready to accept its newest guest. Many came in and no matter how long, loud, or fervently they screamed, no one ever got out.

Until the day an emissary from above dove down deep into the deepest circle of the Pit, flaming form reducing to ashes those who had the ill fortune of being too close when he passed by. No one could restrain him, no one wanted to try even though demons and tortured souls alike raged when the angel's hand fell upon and closed firmly around the arm of one particular man. A stern blue gaze surveyed the landscape and the angel spoke in a voice that sounded like the roar of tens upon thousands of voices and a multitude of trumpets blasting coinciding with the clash of thousands of cymbals.

"Adveho."

With the soul of Dean Winchester in his grasp, the angel beat his great wings and rose up from the fires of Hell and grey plumes of smoke, up out of the Pit and into the realm of light and the living.

Now, the same souls and their tormentors who had witnessed such a display of power some time ago (it was hard to quantify or even pay attention to time in the midst of eternal agony) watched as a man who was still alive and yet not a man at all being brought down into the deepest level of damnation.

He was no ordinary soul, that much was certain for there was a light that emanated from within his form, surrounding him and repelling demons that tried to rush at him from all sides. Clearly, they recognized this man with eyes of piercing sapphire and forehead branded with the inverted cross and Lucifer's seal and all beheld the shadows of rising wings that flashed on the walls for the barest hint of an instant when a spurt of hellfire flared up.

Unlike many of the souls delivered into the abyss, he was not struggling. The man's jaw was clenched tight in obvious discomfort, his brow was furrowed and yet his step was steady and his gaze directed straight ahead as he was more or less dragged by means of chains connected to manacles encircling his limbs deeper into Hell.

Who would have ever imagined seeing an angel in Hell… twice?

"Well, kiddo. We meet again." Alastair moved forward, white eyes meeting and clashing with blue. The chief executioner and torturer for all the realms of damnation looked his newly acquired prize up and down, pleased. "This time though," he hissed, sidling up to the angel bound within mortal form, "this time, you're in my territory."

"Come again?" The now-empty pie tin was tossed aside without ceremony and Dean leaned forward, features strained in anxiety. "Sex Diluco what?"

"Six Dawns and Six Hours," Sam quickly supplied, looking to Bobby for guidance as to what to say next. "It's- uh, it's Latin and it's a ritual that, when completed, breaks another seal."

Dean swallowed hard and looked down at his hands , clasping them tightly together to hide the fact that they were shaking worse than a high school boy waiting to pick up his prom date. Six hundred possible seals, sixty-six that need to be broken and now this. Geez, what is it with evil and the number six? "Yeah? What is this ritual, anyway? And what does it have to do with Cas missing?"

"…a part of it requires the sacrifice of an angel."

In one swift, deft move, Dean reached out and snatched away the textbook, a difficult task to do with one hand given than the volume held more than two thousand pages. After nearly ripping several pages out and almost giving himself tendonitis, he balanced the book on his lap only to be confronted by letters strung together in what seemed to be nonsense phrases. The elder Winchester looked up. "It's in Latin," he said stupidly, stating the obvious. Really hard Latin.

"We've been working on a translation when you were asleep." Sam pulled out several legal pads covered with his lopsided scrawl. "From what we can figure, this ritual is divided up into different segments, each whose requirements have to be met before moving onto the next and they're…" He flipped through several pages of notes and blew out a lungful of air. "They're pretty extensive and intense."

In a response to the elder Winchester's silence, Bobby took up the lead. "As you've probably gotten from the name, it has to take place over a timespan of six days. On the first day, it says that a battle will be instigated between the forces from above and those hailing from below. At the end of the second day, the sacrifice will be betrayed into the hands of the wicked and branded into its vessel by means of Lucifer's seal, trapped and essentially, no more powerful than you or me."

"That's the mark you saw, Dean," Sam said quietly, observing how his brother's knuckles were going white; he was clenching his hands together so hard. "The text doesn't say much about what happens on the third day, only that 'temptation and tribulations will be presented as trials'." He turned the legal pad sideways, squinting at his own unintelligible writing. It pretty much says the same thing for the fourth and fifth dawn except that 'the land will become one filled with wickedness to hasten the breaking of the angel's will. Once again, the temptation will be offered but he shall refuse, seeing the ritual into the sixth dawn.'"

"What temptation?" Dean's voice was hoarse, his throat tight.

"Freedom in exchange for Lucifer's vessel."

Sam cast a glance at his brother. Dean was still sitting in the same position on the couch that he had assumed at the start of the narration, frozen in shock at what had just been revealed. It was quiet now, Bobby having fallen silent as the words uttered began to sink in with its terrible and tragic implications.

There was a knock at the door- firm and unrelenting, bordering on the edge of being a demand and Sam stood abruptly, grabbing the shotgun that leaned almost innocently against the wall. Inching closer to the door, he reached out for the knob as another rap of knuckles against wood rang out, this time with definite impatience. Suddenly feeling very much like he himself had been infected with Yellow Fever, he steeled himself, took a deep breath and flung open the door with such force that it bounced off the wall, swinging creakily on its hinges. He brought the shotgun up to chest level quickly, pointing it at the dark-haired girl who stood there looking irritated.

"You can put that down, Sam." He stared.

"Ruby? What are you doing here?"

Dean's eyes snapped upward from where they had been fixed firmly on the floorboards to glare at the girl who strode into the house like she owned it. Bobby mirrored his movements for it was clear that there was no lost love between him and the demon race, but Sam made a placating gesture, silently pleading for just a few seconds. Dean, although he noticed his brother's signal, made no such effort to reign in his disgust. I'm not going to give this bitch the time of day let alone a chance to explain why she's here on our doorstep.

"Why the hell are you here?" he spat out, a demand far harsher than Sam's stunned inquiry. He half rose from his seat, hand wandering into his jacket pocket where his wandering fingers curled around several vials of holy water.

"I have information that you might be interested in, idiot." Ruby, while having switched vessels, still had a tongue that was sharper than ever when provoked. "I'll pretend to be intimidated, you can sit still and act like you've got some brains in thick skull of yours and we'll all play nice for a minute."

Dean's chin lowered, his jaw set and he glared upward through hard, emerald slit eyes cold as death and ready to shred the other to ribbons. "You wanna say something, then stop being coy and just say it, bitch."

Ruby's eyes narrowed. "Don't call me bitch," she hissed, eyes going black as her pupils expanded over the irises and the whites of her eyes.

"Aw, I'm sorry. Did I hurt your feelings… bitch?"

The demon made an angry move toward him but Dean whipped out one of the vials of holy water, flipping off the top with his thumb. Don't even think about it. Ruby drew away slightly, cowed. "Look," she said angrily, "Do you want to know this rumor I picked up about your angel or not?"

Dean's brow furrowed at the diction. My angel? Since when did he become my angel? Sure, he pulled me out of Hell and all, but still… "More demon whispers, huh?" he muttered sarcastically.

Sam took the chance to jump in on the tense exchange. "What did you hear?"

The three men were floored with the words that came out of the girl's mouth next. "That land filled with wickedness your little book's talking about? Where else could that be but Hell? You boys are moving into the fifth dawn." Ruby nodded out the window where the sun was slowly rising up over the horizon, bathing the land in crimson and hues of blood red.

Dean literally flew out of his seat and grabbed her.

With a sudden swiftness and ferocity that he had never experienced or exuded before, the hunter seized the demon by the throat in a grip hard enough to bruise, mind whirling at a hundred miles per hour. In a towering rage, he slammed her back into the nearest wall, the heat in his veins overflowing like an uncontrollable flood.

"Who did it, huh?" he growled, not caring that he was almost definitely cutting off her air supply, not caring that she had helped them before in the past, not caring that Sam was calling his name and trying to pull him off the demon. "Who has the power to do this?" Dean held the image he had drawn of the brand an inch away from Ruby's face. "Answer me!" he roared, shaking her hard until her teeth chattered.

"Dean!" Sam was amazed at his brother's strength. Ruby's feet were kicking half a foot off the floor and still Dean showed no indication of letting go, his face frozen in a mask of fury. "Bobby, help me!" With the older hunter's help, the two of them managed to pry Dean away and hold him back as Ruby collapsed in a heap, gasping for breath.

"You haven't answered me," Dean said coldly, no remorse in his eyes as he drilled the demon with a glare that could have melted the sun. Ruby glared up at him, eyes shifting to black again.

"Who else, asshole?" she spat in return, contemptuous venom lacing her words. "One of his own kind."

Two seconds passed as the news sunk in and then Dean shook off the hands that were loosely restraining him, swearing in words that would have made even the most foul-mouthed demon flush. "Uriel," he somehow ground out from in between gritted teeth. "I knew it. That goddamn son of a bitch-"

"Didn't do it," Ruby interjected, pushing herself up off the floor. She ignored Sam's desperate shake of his head and mouthing no and stared into those cold panes of emerald. "It was your girl Anna."

A/N: I think Ruby's awesome; she's an interesting character and the dynamic she displays as being a demon who's aiding the side of good really intrigues me (although I really preferred Katie Cassidy's performance over the new actress, so that's how I wrote her here). Let me know what you think!