Author's Notes: This is my first attempt at fanfiction for Supernatural, so any kind of constructive feedback is more than welcomed. This story can also be found on my writing journal, restlessbrook, on livejournal. :)

Also, there are spoilers for season five, episode ten, Abandon All Hope, here. If you haven't seen the episode yet, I don't suggest you read this, as the spoilers mentioned are pretty significant.

Summary: He is always joking, as Zachariah so aptly put it, because joking is the only way he knows to deal with the utter gravity of his situation. Joking remains his last line of defense in his world where nothing ever ends up exactly right. Joking is the only appendage holding his sanity together.

Disclaimer: I own nothing involving Supernatural. This was written for entertainment purposes only.

Angels Are Watching Over You

"Angels are watching over you."

The maternal glow of her blue eyes. Her blond hair, encircling her sweet smile just like those halos she'd always told him about just before she tucked him in. The brief warmth of her lips against the skin of his forehead just before she left to turn out the lights. Every attempt he makes at closing his eyes now, all these old memories rush back to the surface, desperate like the souls who'd escaped the devil's gate that fateful day so long ago.

He wonders if his mother actually knew the truth behind those words, or if she was merely enacting the usual rituals of a parent, depending upon the false security of faith just to make it through the day. He wonders if she knew just what kind of angels were really "watching over" him.

Dean Winchester doesn't sleep anymore. He hasn't for a long time actually. Sure, he'll grab a few hours of shut eye here and there, letting Sammy drive for a couple hours while he dozes off for a few miles, or curling up in the moth-eaten sheets of their cheap hotel room for a couple more hours right after a hunt. But he can't remember the last time he's gotten a decent night's sleep.

Every time he dares to hope for more than four hours of slumber, that wide, gaping hole within him, that empty space he's carried with him since his return from down under, starts to burn again, and his eyes open in an instant, and he's rolling around desperately, shaking off the covers and just trying to find a way to get back to bittersweet oblivion. And of course, no amount of tossing or turning ever works. No matter how much exhaustion has eaten away at his resolve, like rusted pipes, he remains awake at the most ungodly of hours. The ticking of his watch, with each minute that passes him by, beats as loudly in his head as his nervous heartbeat.

It's a miracle that Sam has yet to say anything. Yet. Dean's certain his younger brother is more than aware of the rings, dark as bruises, haloing (ha) around his eyes. He's messed up on the job once or twice, fallen on his ass a few times. Nothing some lame wise crack can't smooth over. Still, it's hard to avoid the concern lingering in his younger brother's eyes. Yet, every time, Sam says nothing.

Perhaps it's for the best. Things between them still aren't like how they used to be. He would give anything for it to be otherwise, but he just can't ignore the lingering hurt, throbbing faintly now, like a sprained ankle, in the pit of his stomach. Right next to the gaping hole where some part of himself used to be. Some days are better than others, but Dean still feels like he's perpetually walking on glass.

He groans before finally giving up on sleep. He takes his time sitting up, all his thoughts rolling around in his head like marbles recently spilt by a clumsy child, randomly clashing against each other with no real purpose. Every limb feels heavy, weighed down by lead as he unfurls from the bed and makes his way over the bathroom. He figures this whole mess, the whole end of the world deal, must be the main reason for his sudden insomnia. Some inner voice within him snorts, that same darkness he once confronted shortly before going to hell. The darkness that knows him better than himself.

The water is arctic; it stings as he splashes his face, desperately seeking clarity. He feels slightly dizzy, off-balance. He hopes that just maybe, sleep is finally catching up with him, even at the cost of winding up face down on the unforgiving bathroom tile.

He abandons all hope the moment he catches sight of the other face in the mirror. At once familiar, and yet strange, that face he knows so well simply stares at him, almost right through him. Those steely eyes that had watched him surpass a brief childhood for a demanding life as a hunter. That firm mouth, curved slightly in a rare smile, now silent, lacking in orders to watch out for the demon just around the corner, or that vengeful spirit in the closet-to look after Sammy while he's away.

"Dad?" He blurts out the word before he can stop himself. Even after all these years, he has yet to lose the habit.

He turns around abruptly to find John Winchester in the flesh, standing directly behind him. And he knows better than to believe in the image, understands almost instantly that this is an illusion of some kind, hiding angel or demon, he can't be sure. But knowing this doesn't prevent the sudden surge of childish glee from fluttering around like panicked butterflies in his stomach. Nor does it suppress the fear; his instinctive reaction to his father's intimidation still drilled into him after all these years, combining with the dread of just who this stranger might be. He fights the urge to ask him questions as to what he should be doing next. He knows better.

"Hey, son." His father, or, more accurately, whoever's masquerading as his father, steps closer, hands shoved awkwardly in his pockets. Dean's not entirely fooled by this false display of modesty. There's something familiar about his presence that has nothing to do with his father.

"You're not my father." His voice hardens as he speaks. John's smile widens just slightly, going crooked, in response.

"I'm going to take a stab in the dark here. Michael, right?" Dean stands firm, arms crossed in his usual, take-no-bullshit pose, attempting his usual cocky demeanor. But even he can't entirely ignore the trepidation starting to manifest itself through his body. His hands are shaking, hiding in the crooks of his elbows. He can feel the sweat begin to stick to his sickly-looking skin.

"Close, but no cigar." His father, who apparently isn't Michael, either, walks closer, and Dean can feel his stomach as it plummets to the ground. "You've got the wrong brother."

"Lucifer." He growls the word, like a mad dog itching to get off his chain. He releases his arms, feels as his hands furl into tightly clenched fists. Yet, a strange paralysis falls over him. Much to his annoyance, and against every gut instinct he's ever had, he remains still while the devil stalks closer. Circling him, like a bird of prey.

"What the hell do you want with me? How the hell did you even find me?" Dean twitches. He's fighting so hard not to give in to the shudders simpering like boiling water just beneath the surface of his skin.

"You're dreaming, Dean." The way he pronounces his name, just like his father would, sinks into him like a set of hellhound's teeth, and Dean can taste the anger as it rises as incendiary as hellfire in his throat. He hates that the devil knows just which trigger to pull to ignite him. In a way, it reminds him of Alistair, a thought that only makes him loathe the man pretending to be his father all the more.

Yet he's so entranced by the devil, Dean doesn't even pause to think about what he's just said-that he's dreaming. This whole nightmare reeks of reality like hell reeked of sulfur, blood and burning flesh. Once again, he feels cornered, without any hope of escape. Nothing good could ever come with such close contact with the being who brought about the end of the world.

"You are a fascinating man, Dean Winchester." Lucifer rakes his eyes over his form, calculating. "Almost as interesting as your younger brother."

"And just what is that supposed to mean?" He asks, more in control of his fear, now. Or at least, he hopes he appears as such. "Aren't I public enemy number one in your little campaign to end the world?"

"Yes. And you did shoot me." The devil quirks his father's countenance into a look of bemusement. "I'm an honest being, much to the surprise of your people; that hurt a little. Well, a lot, really. Regardless, it doesn't matter now. I'm just so intrigued on how dead set you are on stopping me, and yet, you refuse to do the right thing."

The devil's words chill him to the bone. He wonders if this is another ploy set up by Zachariah, and he lets out another growl. He is so fed up with this entire, manipulative angel bullshit.

"Oh no. It's not what you think. I'm really me." The figure posing as his father spreads his arms and opens his palms pointing upwards, a shallow gesture of peace. "I came here of my own free will."

"Yeah? But you still haven't explained why you're here." Dean wants so badly to come off as angry. He tries to ignore the fact that he feels ten again, pressed up against the wall trying to avoid being hit by his father's disappointment.

"You belong to no one, Dean Winchester. You're independent, tough-unwilling to let others manipulate you." Lucifer smiles, and Dean feels like he's back on the rack, the way that familiar grin, at once his father's, and yet not, twists into him like a wicked blade. "It's a trait I especially admire in a human."

"You've withstood the horrors of hell, and lived to tell the tale. Although, from what I've heard, you really would make an excellent demon." Here, Lucifer at last sheds the image of John Winchester for the form of his current vessel.

Dean visibly shudders. Admiration from the devil is absolutely the last thing he needs right now. And he can no longer deny the fear creeping through his bones like insects. He finds himself suddenly at a loss for words; he cannot bring himself to speak. Part of him almost wishes the devil would just kill him now and get it over with.

"Which is why I regret the fact that I'm going to have to kill you, of course." Lucifer is just barely keeping his vessel together, Dean notices, as the devil backs away slightly, a triumphant glow in his eyes. Even more blood trickles down the side of his face, like so many streams, and his skin is starting to crack.

He's died before. Many times, in fact. Death itself isn't anything new to him; he really shouldn't feel so afraid right now. But the fact remains that he is scared shitless at the thought of dying at the hands of the devil. Still, he somehow manages to swallow his fear, and plaster his trademark, cocky smirk on his face.

"I think you'll find you'll be doing no such thing." Before he even gets the chance to speak, another, familiar voice breaks out in the shadows behind the devil. The devil pivots abruptly, as Dean cranes his head over to the side to catch a glimpse of his newest, unwanted guest.

With a painful, almost silent gasp, he takes in her familiar, blond hair and lively, brown eyes. It seems like just yesterday she had still been alive, making wisecracks as she turned down his half-assed, end of the world speech. An agony similar to the pain he suffered losing his father surfaces, summoned by the illusion of her existence.

"Hello brother. I was wondering when you'd show up." The devil's greeting rings out surprisingly flat, lacking in its typical arrogance.

Dean wonders if he's imagining it, the way Lucifer's shoulders suddenly tense up, the way the entire body of his vessel shrinks into itself. He comes to the conclusion of its integrity moments later, when he catches the lapse in confidence in the devil's eyes. Dean is suitably impressed, almost in awe.

"It's been awhile, Lucifer." Jo's voice sounds so deep and strangely formal. Dean turns his attentions back to her as soon as she speaks, noting the stiffness of her posture, like that of a hardened soldier. "But I really don't think now is the best time to be playing catch up, as the humans call it."

"No, you're right. Some other time then." Lucifer turns and vanishes, startling Dean with the hastiness of his retreat. He turns back to Jo to find her almost expressionless, a hint of disdain seeping slightly through her countenance.

A new dread rises up in his throat like bile at the prospect of being left alone with the other angel. He's faced angels and demons and ghosts before. Hell, he's even faced other archangels, and the devil, no less, before. But there is something deeply frightening about the prospect of facing Michael that catches him off-guard.

"Hello Dean." Such a simple phrase, and yet, spoken in her voice, with his intonation, forces him to close his eyes momentarily, hoping for some sort of respite from this long, never ending moment. "I've wanted to meet you for a very long time."

He opens his eyes to find Jo directly by his side, looking up at him with an intensity even greater than Cas.

"Yeah, because you want in my meat suit, right?" He is always joking, as Zachariah so aptly put it, because joking is the only way he knows to deal with the utter gravity of his situation. Joking remains his last line of defense in his world where nothing ever ends up exactly right. Joking is the only appendage holding his sanity together.

"That's right." Dean finds that he can't look away, no matter how much he wants this all to go away. "I will not lie to you, Dean. I never have. But I'm not as much of heartless brute as you think I am."

"Really? That's funny, because all the other archangels I've ever met have said they same thing, and they all turned out total douchebags." Dean is growling again, perhaps just because it is Jo saying all this to him. Jo trying to recruit him for the angelic cause they had fought so hard to remain separate from. Jo, who had become one of the first (of many, no doubt) casualties in this war of angels and demons.

"This form upsets you." Dean's reminded of Castiel in the way that Michael pronounces this statement, like a scientist discovering something unusual about his lab rat. "I am sorry. I thought it would be best to approach you in the form of the person you most wanted to see. Since you're dreaming, it's no problem. I can change."

He finally realizes he's actually asleep, for once. He wonders how he could have been so stupid so as to not have seen it before. Of course this is all just in his head. But this confirmation does little to settle his nerves; instead, it only unnerves him further. How in the hell could the devil get inside his head so easily?

"Is this any better?" This time, it's the voice of his brother that startles him out of his thoughts. "The form of the person you love the most?"

"I don't suppose you could just take on the form of get the hell out of my sight, now, could you?" Dean ignores the rush of relief at the sight of Sam's freakish height and warm, concerned eyes. For the first time in a long time, despite the fact that he still feels exhausted, even in his sleep, he just wants to wake up again and not sleep until kingdom come, which, if things kept on the way they were going, wouldn't be too much longer, actually.

"Dean, I know you don't like me. I don't blame you. But this is important. This about saving the world." What strikes Dean the most about this archangel, this powerful, almost mythological being is the amount of patience he displays. Even then, in his attempts to press Dean to warm to his cause, Michael did not raise his voice, did not lose his temper as Zachariah would have done.

"This isn't about saving the world; it's about ending it, and all because of this stupid fight with you and your brother." Dean shouts now, angry enough that he felt he might punch a hole through the wall.

"I'm trying to save my brother, actually." Michael says this in Sam's quiet tone, the kind of voice that never fails to grab Dean's instant attention. "You can relate, can't you?"

Dean cringes, images of Sam flickering vividly in his mind-Sam, high on demon blood, of Sam kicking his ass back in that hotel room-of Sam, lying still, as cold as the air around them so many years ago, just before he'd sold his soul to bring him back. And, the most vivid, Sam, poised perfectly in that white suit, wearing the spirit of Lucifer inside him, stepping down on his own neck five years into the future.

"You may not believe me, but I love my brother, Lucifer. I always have. If we win, and Paradise does spread to Earth, he will be redeemed. He will no longer burn in hell." Dean hates the sudden surge of sympathy Michael draws up from him with his words. And yet, he really can't deny their power. Sam's voice, laced with Michael's words, sounds surprisingly stark and honest.

"Last time I checked, doesn't heaven winning involve killing your brother?" Dean points out, vindictively happy to undermine the other side in any way he possibly can.

"Yes." Michael replies. "I know you're not the most dedicated of believers, Dean, but death is only the beginning. With heaven on Earth, Lucifer, like every other casualty, will be reborn into paradise. All those you've lost will have a second chance at life. No one will ever die again."

Dean knows better than to trust such pretty words. Almost since he was born, he had been raised to see through the transparent depths of such promises. Propaganda, really. Yet, within him, he can feel his resolve crumbling, his smirking veneer fading. He shocks himself by how much he desperately wants to believe in what Michael is saying, how quickly his own skepticism is losing ground in favor of the ideals in Michael's words.

"Dean, I admire your courage. Your independence, and your determination to fight this battle in your own way. You were raised as a warrior of the noblest kind. You put your family before even your own well-being. You've endured a wasted childhood and the fires of hell. Let me help you regain your family. Let me help you save your brother, before Lucifer gets to him. If you let me in now, we may be able to get to the devil in his current vessel."

"You really think that'll work?" Perhaps because it is the form of Sam saying this to him, Dean relinquishes his venomous front. He sighs, and he acknowledges the aching exhaustion within him. He is so tired of living. It's probably why he feels so tired even now, he thinks, even in his sleep. And he has never thought of it before, the possibility of destroying Lucifer before he inhabits his younger brother.

"You don't have to say yes right now." Michael concedes, moving away from Dean. "I can see that you need your rest." Dean smiles weakly, in spite of himself, at the familiar concern on his brother's face looking over him from within. "Take care of yourself, Dean."

Dean watches Sam's retreating back as his eyelids begin to droop heavily. He does not feel content, exactly. In fact, he feels even more conflicted. He sympathizes with Michael, does not hate him like he hates Zachariah. In fact, he would even go as far to say that he almost likes him.

"Oh, and Dean?" Suddenly, just before he gets the chance to fall back into oblivion, Dean sees Sam turn around, with something akin to mirth in his eyes. "Tell Zachariah, the next time you see him, that he's a-what's that word you humans use?-oh yes. A douchebag."

Dean falls back into dreamless sleep laughing.

He opens his eyes to find himself sprawled across the bathroom floor. With a groan, he picks himself up, head heavy, as if under the weight of yet another hangover. He wanders over to the window, looks to see that Sammy's still out like a light, and that only a couple of hours have actually passed. Deep down, he understands that all of what he saw was real.

He turns to gaze out at the starless night, thinking it all over. He cannot get Michael out of his head, and he wonders if he's already given part of himself over to the archangel. He remembers the impressive way in which Michael banished Lucifer, and still confessed to a love him, afterwards. Of course, it could all be a trap. He knows this. Yet, the larger part of him still yearns to believe, and he wonders if he's feeling the religious sort of faith for the first time.

He sighs again, looks out at the night.

At the very least, Dean hopes now that his mother is watching over him.