Hi guys! I know, this is not another chapter of Four Letters, and I know that it's kinda gruesome, but I am having so much writer's block right now, so enjoy an idea that's been bouncing around my head until four minutes ago.

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"Crowley, sir?" The man spoke up hesitantly, looking concerned.

"Yes?" Crowley drawled back, looking bored.

"Are we really quite sure that this is the best course of action, considering the circum-"

"Of course it is!" Crowley snapped back, looking quite ruffled. "He's the son of my nemesis, he died and his soul went to hell, he's fair game!" There was a moment of silence. "Besides," Crowley said offhandedly, "he killed a Winchester."

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Jack found himself at the end of a long hallway, one oak door ahead of him. It was dark here, and his heart ached. There was only one way to go.

Jack walked through the door with an ominous creak, a confused look adorning his face. It was dark here, and humid. As he glanced around the room, he could barely see various shapes scattered throughout the room, though he could not properly make them all out. Even as he stared, there was movement in the darkest of the corners, and a darkened, twisted being stepped into the light.

He was small, shriveled looking, with leathery skin and no hair whatsoever. A simple pair of pants, though bloodstained, rested on its bony legs. He could see matted blood leading from its mouth down to its chest, some of it still seemingly fresh. However, the most terrifying of the creature's features had to be its eyes, which were swimming with blackness and tears of red.

"Demon." Jack's breath caught in his throat. It had to be. Then, he turned to look once more back the way he had come. "Wait- how?"

"Time is fluid here." The demon's voice was deep and gravelly, and his mouth was filled with simple blackness, not the twisted maw of thorny teeth Jack had imagined. It was almost scarier, in a way.

"Why am I here?" His voice came out shakey, though the question remained.

He thought he could see a flash of sympathy in the twisted creature's eyes, but it was quickly gone, replaced with indifference, and a little malice. "Your punishment, for all those you failed to save, for all those who died needlessly. You thought you were going to heaven, Jack Kline? You're an abomination, no better than me." The creature took a step in his direction. "Let us begin."

To his credit, the creature started out slow. When Jack questioned him, he simply did not respond, though he tied the ropes a little tighter. Jack looked down at them in fear, as the blood on them still seemed fresh. It had not yet turned brown, and was still slightly damp against his pale, perfect skin.

The creature tortured him then, or at least did his best to. He started with mortal instruments, moving from there to different techniques as each weapon before him failed. He never seemed upset, he simply watched as the wounds healed themselves, examined as Jack's own skin stitched back together perfectly, peachy and white. He never cried out in frustration as Jack felt he would. In fact, past those first few sentences, the creature never spoke another word.

Eventually, the creature turned to the last blade in the room. He picked it up, turning to face Jack, and smiled. It was really that smile that got to him, made his blood run cold, though not because of the creature's toothless mouth, or cracked and bleeding lips. It was a smile of one more knowledgeable, and one of malice. He knew, then, that the blade would puncture his skin, and allow his blood to run freely. He knew, somehow, and he was very afraid.

He was right.

What would Sam and Dean have done?

The blade glided smoothly through his skin, parting it and allowing red droplets to well up to the surface. He let out a small whimper of pain.

What would Castiel have done?

The demon kept carving, slowly flicking little bits of his skin away, until nothing but muscle and bone remained.

What would a Winchester have done?

But the torture went on. Time and time again, Jack could feel the blade grazing his skin, could feel it sink deep into his arm and wedge there. He could feel it as his teeth were knocked out, and his mouth matched that of his tormentor, and he could feel it when the slashes from the corners of his lips rendered him permanently, grotesquely, smiling. He could feel it in his very soul, though he wasn't even sure he had that anymore. Did the son of Lucifer even have a soul? It sure didn't feel like it anymore.

What would my family have done?

Did he even deserve to still call them that? He didn't know. The only thing he knew was here and now.

He was powerless to stop it, however, as the creature slunk around him, blade glinting golden in the low light. It was like they knew his every weakness. He hated its inexplicable knowledge. He hated himself for being so weak. And he hated himself, most of all. How could I let myself sink this low? All the way to hell?

His thoughts were almost worse than the physical pain, almost. He let out another wordless cry of fear and pain as the blade sliced clean through the tendon at the base of his leg, and he felt his foot go numb. The world began to become fuzzy.

Next, the creature turned his back to him, turning around with a box of pins in his hand, and extracting the largest one. It glinted with the same sharpness and malice of the blade the creature had cast aside. And then he inserted it into the base of his skin, right underneath his fingernail.

"Castiel!"

He didn't deserve to cry his name.

His eyes went wide. He hadn't meant to call out quite so loudly in his pain. His cheeks colored both with pain and embarrassment as the creature turned to him once more. And then it leaned forward, driving the golden pin even deeper under Jack's fingernail. He could feel his nail crack, and large tears began to run down his skinned cheeks, mixing with the blood there already.

He could still remember Dean's face as he plunged the archangel blade through his chest. He could still remember Sam's anguished scream of pain and horror. He could remember the look in Sam's eye as he cradled his brother in his arms during his dying breaths. He could remember that pain clear as day. The tears only streamed down his cheeks faster.

The pain went on for days, weeks, months. Jack lost count. All he could see in his mind's eye was Dean's look of betrayal as he plunged the archangel blade into his chest. It wasn't your fault, some little part of him hissed. You didn't know he was no longer possessed by Michael. He ignored that voice. That voice told nothing but lies.

He had become precisely the monster that he had struggled so hard not to become.

It must have been years before something changed. The creature was moving sluggishly that day, for some reason, and had gotten sloppy. Though Jack could barely see through his own bloodshot eyes, he saw the creature set down the blade a little too close to him, turn its back for just a little too long.

And then he moved. The blade made a sick kind of thunking noise as it was driven straight through the creature's back. A sudden light filled the room as both Jack and the creature cried out in pain, and then all was still.

Jack quickly cut through his restraints, falling to the floor in an undignified pile. With shaky legs, he stood up, though his flayed skin had long since hardened, becoming leathery.

First he checked the door, though it was locked. Whirling around, he began to squint into the dark corners. Maybe there was something back there that would help him. He began to drag the body of his tormenter with him, to examine the darkened corner that it had first emerged from. And then then saw it. He nearly dropped the creature in shock. There was a pile of bodies in the corner, seeming to expand as far and as deep into it as his blurry eyes could make out. All of them were identical to the one he held.

Carefully, gingerly, he tossed the body onto the stack, sitting beside them as more silent tears ran down his cheeks, horror overtaking him as he finally understood his circumstances.

The door, the previously locked door, opened slowly, with a creak. Jack stood up to meet the gaze of the boy looking around in his confusion, and barely contained his gasp.

"Demon," The boy said, before turning back the way he had come in confusion. "Wait- how?"

And then Jack walked closer to the boy, knowing what was next to come for him. "Time is fluid here," He simply replied. He knew his lines, he knew his part, and he knew that this would be the worst punishment for himself yet. He just couldn't believe how far he'd fallen.