Potential series I got going on here
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It's hot and unbearable but Dean has slowly grown accustomed to the infernal temperatures of Hell. He's been rotting in the pit for what feels like 40 years now and Alastair says he'll eventually embrace the insane heat. Alastair claims he doesn't notice it anymore though Dean has seen him fan himself briefly on more than one occasion. In any case, the heat wasn't as terrible as it once was – perhaps there is some amount of truth to what had been told. Nevertheless, Dean knows he will never get used to the horrifying sights surrounding him.
Hell seems endless with a constantly changing landscape. The only thing that remains somewhat consistent is the web of chains up in the realm's sky and the flashes of lightning followed by thunder and terrified shrieks of tortured souls. Dean spends most of what he refers to as 'nights' looking up at it and thinking. Sometimes he thinks he catches glimpses of light far away which he has come to identify as the way out of Hell. A part of him strongly believes that if he can just find a way to climb up to it he can be free but he never attempts.
Dean only tried to flee from Alastair once and it hadn't gone entirely well. His absence had been noticed rather quickly and the price he had paid for his disobedience was as worse as any torture he had suffered during his initial thirty years in the pit. Alastair had warned him that if he ever tried to flee again, he would be put back on the torture table for all eternity. Dean is too afraid to test the threat.
Notwithstanding of the fact that Alastair had tortured him mercilessly for three decades, he and Dean got along fairly well. Alastair definitely finds pleasure in his job and honestly hates leaving Hell when he is summoned or tasked to do so. He is a relatively good and surprisingly patient teacher, rarely snapping at Dean for his reluctance in committing certain acts. He seems to understand that Dean is very much human and that that part of him will not burn away any time soon. As he puts it: "I've got all of eternity to see you turn".
The 'day' has ended and Dean retreats to the room Alastair had once brought him to upon his release from the rack ten years prior. Even though the terrain shifts constantly, the room he has come to see as home remains in the same location and Dean can always find his way to it. He is rarely bothered by daemons anymore now that Alastair has officially taken him under his wing and – for a demented reason – he's rather thankful. Some do still try to get their hands on him for revenge's sake but Alastair has taken the liberty of providing him with the tools necessary to defend himself. Of course, he had to earn them and the feats he had to accomplish had been far from easy. In any case, Dean is as safe as he is ever going to be in Hell.
He barely falls onto the stone bed when he feels the familiar presence of his mentor invade the room. Dean nonetheless doesn't spare him a glance and gets comfortable before shifting on his side. "What's up?" He asks.
"I'll be leaving for a short while." Alastair informs, "I want you to make sure the others under my command fulfill their tasks. If they do not, you know what to do."
"Where are you going?" Dean asks curiously.
"Business at the Gate." Alastair says and he seems partially annoyed, "Some scuffle the buffoons can't manage on their own."
The mention of the Gate has Dean's heart throbbing and beating painfully in his chest. A sort of excitement and hope takes over him and has him sitting in seconds as his mind begins to race. He wonders if the Gate really is the light he occasionally sees in the gloomy sky. He wonders if he could escape if he follows Alastair. Alastair senses the thoughts crossing his protégé's mind and smirks as he takes steps closer to Dean and leans in. When he stops, his lips are inches away from Dean's ear and the tickling of his breath unnerves him to no end. He whispers: "Remember the warning I gave you Dean-o. If you try to follow me, you'll be back where you started in seconds for all of eternity this time, understood?"
Dean gulps audibly and nods briefly. Alastair pulls away and stands upright.
"Wonderful." He says, "This also doesn't give you an excuse to slack with your job."
"Yeah, I know." Dean mumbles. "Have fun."
And just as such, Alastair is gone. Dean pauses for a minute and makes sure he is completely alone before curling in on himself and sobbing. He isn't sure how he manages to produce the tears in an environment in which he feels severely dehydrated all the time though he supposes Spirits in Hell don't necessarily abide by the laws of human biology and logic. And so he cries and cries and remembers his life when he was alive which only makes him feel worse. Dean misses Sam. He misses, Bobby, Ellen and Jo too. He didn't even have the chance to say goodbye. He hopes they're okay and looking out for Sam – God knows the kid is lost without him. But Dean trusts in Sam and in his strength and believes he can defeat and overcome whatever is hurled his way.
And so Dean spends the 'night' as such. When 'morning' comes, he returns to the torturing tables and supervises the other daemons as commanded by Alastair. They all seem strangely focused but Dean brushes it off as something positive. He goes to his station and commences torturing as well. The first soul he is served on that day is a young woman that was once a drug dealer. She is utterly frightened and confused – an obvious newcomer to Hell.
"Please!" She begs Dean and struggles against her restraints, "Help me!"
Her tone changes quickly as she sees Dean scan his tools, debating which to use first. She begins to beg for mercy and forgiveness and Dean finds himself unfazed. He has grown immune to the pitiful apologies and cries of his victims over the decade and has actually begun to find a certain degree of enjoyment in what he does. He supposes it's normal considering Hell is burning away his humanity. One day he will become a daemon and forget himself in the process.
Dean settles on the scalpel. He figures he'll start small and gradually get bigger. He did always prefer his smaller tools. They permitted for more precise and detailed incisions.
The following part is like a dance to him. Dean swings the scalpel brilliantly, cutting through the flesh as though it were softer than butter. Drops of blood splash in every direction, dotting all of the surrounding surfaces. The girl shrieks louder than a banshee and remains rigid and tense as Dean cuts through her. Though she still struggles for freedom, Dean has learned long ago how to make the slices and slashes he desires on an agitated target. Alastair had been particularly proud in regards to how fast he had caught on.
When Dean stops, his hands are soaked in the girl's blood and she's a whimpering mess. She tries to stay as still as possible to minimize the pain surging through her body but she has yet to realize logic ever rarely matters in Hell. The dark realm has a set of laws of its own and they are very different from those of Earth.
He looks back at his tools, now struggling between a crooked dagger and pliers. He supposes it has been a while since he's denailed one of the souls presented to him. Dean reaches for the pliers and with a snap of his fingers, the girl's fingers and secured. Alastair had taught him the trick shortly after being released from the torture tables. One of Hell's many laws was that the imagination of daemons shaped the realm. Typically, the strongest daemons were the most creative – and consequently the most disturbed. "You're only limited by your imagination." Alastair had told him.
"Please stop!" the girl begged through ragged sobs as Dean squeezed the tip of her fingernail between the pincers, "I'm sorry! Please! I—"
Dean dryly yanks the nail from her finger and pulls a gut-wrenching screech from the new soul. She wails pitifully and grossly upon recovering from the pain and Dean readies another finger. He tells himself to use said torture method more often seeing as the results are quite…lovely.
He pulls out another nail so as to distract his conscience but it fails. As the girl breathes heavily and whimpers from the pain, Dean pauses and reflects on his recent thought. Never once in his life had he killed or hurt anything that didn't deserve it or hadn't attacked him first. In any case, to delight in the pain and agony of another human being was still disgusting and Dean begins to second guess his actions. He looks at his trembling hands and wonders just how much as Hell corrupted his soul.
Just then the piercing shrieks of daemons fills the air. Dean is panicked and confused – he doesn't understand what is happening when he sees a blue light zoom pass him. It goes directly for the daemon a couple of meters away and smites him. Dean backs away in pure terror, wondering if the creature will come for him next but, instead, it moves on to another daemon. Soon more of them appear and kill everyone except for Dean – seemingly ignoring him. Dean is still terrified and doesn't know what to do. Alastair has never mentioned whatever those things are and so Dean has no idea how to deal with them.
Suddenly, one of the moves to him and it's so close that Dean can tell it's a man and it has wings. He flaps them gently and the cool breeze it creates washes over him and Dean unexpectedly feels pure. He allows the sensation to wash over him for an instant, basking in it until he is compelled to open his eyes and sees the winged man reach out for him. He seems to be inviting more than anything and Dean feels urged to follow.
"Come…" He says.
His voice is soft and gentle. He oozes with love and kindness and Dean doesn't understand how something so beautiful – so angelic – can be found in such a rotten place. Nonetheless, Dean hesitates. He is unsure whether or not he should obey and looks around for advice. However, those who have been with him for ten years have been smitten and the only one who can tell Dean what to do is Dean himself. He looks back at the pure being in front of him and begins to see his face. The creature resembles a human man – short hair, strong jawline and plush lips – the only dissimilarity being the large white wings.
"Come…" he repeats and his tone sounds a bit more urgent than before.
Dean spares one last glance around him before slowly stretching out his arm to meet the winged man's welcoming hand. Their fingers brush and the sensation of peace and quaintness is like electricity – as odd as the comparison is. Dean is at a loss of words and doesn't know what to say or ask the angelic being but it seems to assess the general idea of his long train of thought.
"Do not worry, Dean Winchester." He says softly and takes all of Dean's hand in his, "You are leaving this wretched place."
And Dean couldn't help the tears that trail down his face. If he was being tormented by a daemon's illusion, he would surely never recover from it. The being pulls him closer and looks at chained sky in which the light Dean occasionally saw can be seen clearer than day. They exchange one last look before Dean is pulled firmly against the man's broad and strong figure. The action surprises him but not as much as the sudden and powerful flap of wings that propels them towards the light.
Everything seems like a dream, Dean can hardly believe this is happening. He feels like he will wake up any second and be disappointed by what surrounds him. Nonetheless, he hopes he doesn't wake up. He doesn't want to be in Hell all over again and despair that no one would ever come save him.
"You are safe, Dean Winchester." The man tells him and holds him closer – almost as though hugging him. "You are sav—"
Out of the blue, a black mass collides with Dean and his saviour, halting their progress and rendering the pure creature confused. The winged man looks around for the assailant when Dean suddenly spots Alastair standing angrily on one of the many chains in the sky. He seems livid and his vicious eyes burn through Dean's soul, inspiring the worst terror he has ever felt.
"Dean, Dean, Dean…" he shakes his head disappointedly. "What did I tell you would happen if you tried to escape?"
Out of pure fear and instinct, Dean clutches to the man's chest and looks at him in desperation. He hopes his saviour won't abandon him. God knows the punishment Alastair has installed will be worse than everything he has ever experienced and will last him the rest of eternity. However, the winged man doesn't shrink at Alastair's hinted threat and flaps his wings menacingly and growls.
"You will not harm him." He hisses.
And just like that, with another powerful beat, Dean and the winged man are propelled closer to the light. They are moving impossibly fast and yet Alastair has found a way to keep up. Dean realizes they're in the midst of a race and he hopes his saviour will win.
What happens next is a blur.
It seems like the exit to Hell is only inches away and the winged man reaches for it but never quite touches it. A heavy mass collides with them again and Dean is unsure if it's Alastair or a different daemon. In any case, one second they're flying and the next they're falling. And then everything goes black.