What Could Have Been

Chapter 20

The screams were louder here.

Millions of souls shrieked and wailed, the sound of their anguish a cacophony that reverberated off the walls and threatened to drive Cas insane. He could barely hear Dean now but he could still sense the agony that rippled across his prayer line and he knew that Dean still called for him.

His soul was a beacon of light in the darkness that drew Cas in deeper.

The last time Cas had been here Hell was under siege from his garrison. At first, demons had thrown themselves into battle like waves dashing against a rocky shore and angels had effortlessly ripped through their ranks. As they began to realise the power of their enemy the lesser demons fled in terror, while those older and stronger pushed through to the forefront. The charge had disintegrated into a one-on-one melee and Cas had been forced to leave his soldiers behind to pursue the mission. Many angels had died, but in the end Cas was successful. He had raised Dean.

But this time Cas was alone. If he failed, there was no one to take his place. Dean would be lost.

A demon leapt out of the shadows onto his back. Claws dug into his shoulder. Teeth gnashed at his neck. Cas spun and threw the creature to the ground. It scrabbled to stand but Cas slapped a palm against its forehead and a burst of Grace burned the twisted soul to ashes.

Cas stared at his hand in shock. His Grace had been waning for years but now he felt power pulsing through him. When Castiel had touched him, the shock of their paradoxical meeting must have revitalised his core. That was good. Maybe he stood a chance after all.

More demons came rushing towards him, alerted to his presence by the flash of light. He launched into the fray. Demons ripped and slashed at him. Hand-to-hand combat skills he had refined with Dean and Bobby enabled him to block and parry blows, dodge attacks, duck into openings and move in for the kill. He felled two demons, twisted a gnarled limb so the creature howled and released him, shoved an assailant into the wall, seized the horn of one’s head and flung it down the passageway into three others, killed another. He could tell that many of these demons had never fought an angel before and he made use of that fact. They were fast but he was faster. His wings flared wide, knocking half a dozen over like pins from that bowling game he had played with Dean. Light bursting sporadically from his vessel blinded the creatures accustomed to perpetual darkness and his hands burned through them.

A dozen lay dead at his feet but more were coming.

Hell was filled with demons. The supply was almost inexhaustible.

Cas surged forward, pressing towards his goal. His kills were brutal, efficient, nothing pretty or elegant but effective.

Just as he had taken out three demons in quick succession a knife arced out of nowhere, embedding in his chest. It was a strangely familiar sensation. Cas pulled it out, much to the shock of the demon who had stabbed him, and recognised it to be the same knife the adult Dean had tried to kill him with the first time they met. He took a closer look at the demon.

“You must be Ruby,” he said. She was supposed to be the one to corrupt Sam Winchester.

He stabbed the knife straight through her eye and kept going. Her body thudded to the ground, lifeless.

The knife proved useful. Cas dispatched demons faster than ever, leaving carnage in his wake. He knew exactly where he was going; he had been there before.

I’m coming, Dean.

Green eyes watched in terror as the blade inched closer and closer to his face.

“So pretty,” Alastair purred. “Such a pretty boy. Makes me wanna strip the skin from your bones.”

Dean jerked back instinctively but the chains held him in place. The tip of the knife pressed into his cheek, not quite breaking the skin. He went deadly still, hardly daring to breathe.

“That’s right, Dean. Wouldn’t want me to slip now would you? You know how angry I get when you spoil my art work.”

He dragged the tip lightly down his chin and across his throat. “Such a beautiful canvas,” he murmured, “ready to be painted in blood. Shall we see what new masterpiece awaits us today?”

“Please don’t,” Dean whispered. He didn’t care how weak and pathetic he sounded. He was long since passed caring.

“But Dean, you love our sessions together. You never want them to stop. Isn’t that what you told me?”

God, he wanted nothing more than to be free from the fear and the pain. But the alternative…

“You enjoy being on the rack. Spread-eagled for my viewing pleasure.” Alastair raked his eyes slowly down Dean’s body and back up again, a smirk playing on his lips. “Bondage play,” he breathed. “Chains around your wrists and ankles, meat hooks embedded in your flesh. Vulnerable. Helpless. The sweet anticipation of the tortures that await you. Never knowing when the pain will begin.” He twisted the blade in the hollow of Dean’s collarbone, slowly, painstakingly, pressing deeper until the skin broke and blood welled up to the surface. He leaned in close, his free hand slipping into Dean’s hair to pull his head back, and lapped at the crimson flow with his tongue. Then he bit down, hard.

The smile he offered Dean dribbled with blood.

Dean closed his eyes. He couldn’t bear to watch.

Fire lanced through his stomach. Dean’s eyes snapped open in shock.

Alastair tutted, dragging the blade out of his gut. “Now see what you made me do? It is bad manners to look away from me, Dean.”


“That’s better. Now, watch closely. You will need these skills someday.” He cut a small incision into Dean’s chest, then used his well-trimmed claws to pull the wound open wider, splitting the skin in a long jagged line. “Maximum pain, minimal damage,” Alastair stated calmly over Dean’s scream. “Then, to maximise trauma…” He dug his claws in deeper, ripping, tearing, burrowing inside. When he pulled his hand out he held a fistful of intestines. “Beautiful, aren’t they? That is the wonderful thing about Hell. I can turn you completely inside out and you won’t die because you’re already dead. You get to be aware of every single sensation, every exquisite ounce of pain. Would you like to see your heart? You can watch it beat in frantic terror as I crush it in my fist.”

Alastair took his time, peeling Dean’s skin off layer by layer. He discarded shredded globules of flesh, shaking them off his fingers to drop into the rapidly expanding pool of blood beneath their feet. He tore into muscles and shattered bones like glass. He reached in and gripped Dean’s spine, snapping it in half with a brutal yank that almost ripped it out of his body. He rummaged through Dean’s insides, swirling organs into slush, pulling his heart out as promised. He ensured it remained connected by a few critical nerves so Dean could feel it be reduced to pulp in the demon’s hand.

Alastair laughed as Dean screamed until his vocal chords swelled and burst. He destroyed him piece by piece, leaving his eyes until the very last, forcing Dean to bear witness to his own destruction.

Only when there was nothing left did Alastair take a step back.

The soul repaired itself, as it always did, but it was a little more broken, a little more damaged than before.

Dean opened brand new eyes to see that he was whole again.

Alastair stood nearby, running his hands through the flame of a torch to sanitise them.

“You have the power to end this, Dean,” he said. “I can take you off that rack.”

It took all the strength Dean possessed to shake his head.

“The torture is going to happen either way. You’re not saving anyone. The only person you can save is yourself.”

“I…won’t…hurt…anyone,” Dean rasped.

“Pity. I’ll see you tomorrow, Dean.”

He walked away, leaving Dean alone.

Dean sagged in his chains, lacking the energy to stand even through the meat hooks pulled agonisingly at his flesh. His head dropped.

Tears fell.


“Five years today, Dean-o!” Alastair announced. “If we were living by Earth time you would be twenty-one by now. A fully-fledged adult ready to take on the world, imagine that. Of course, age is meaningless down here. You ain’t growing any older and nothing about your life is ever going to change. This is all there is. Torture and death, over and over, for all of eternity. We will be here together for your tenth anniversary, and your hundredth, and your thousandth…”

Alastair was right. The pain was never going to end. He was trying to be strong, trying to hold on to his humanity, but there was no salvation in sight.

He couldn’t do this forever. He couldn’t.

And what was the point anyway? He was going to break eventually. He could feel it. He could see it in Alastair’s eyes.

What difference did it make to anyone if he gave in now? He was never going to see his family again so he would never have to see their looks of disappointment. Whoever he had to put under the knife was going to be tortured by a demon anyway.

By refusing Alastair’s offer he was only hurting himself.

“So, what shall it be today?” Alastair asked. “Shall I use my razor to carve you into a new animal? Shall I use fire to bubble the flesh from your bones? Shall I drip acid into your eye and let it burn through into your brain? Shall I shatter every single bone in your body? Shall I use the whip…? Oh, yes, the cat-o-nine-tails, that’s a favourite of mine. You screamed so delightfully the last time I used it, do you remember?”

Dean remembered. He remembered every moment of every torture session in vivid techni-colour detail.

“Wait,” he whispered. “I’ll do it.”

Alastair turned from his table of torture devices, eyebrows raised. “What was that?”

“I’ll do it,” Dean said louder. He hated himself. “I’ll do whatever you want. Please, just get me down from here. I’ll do anything.”

Alastair began to grin. “Really? You’ll be my apprentice? You’ll torture souls with me?”

They were going to be tortured anyway. It didn’t matter. “Yes.”

“Well, well, well. I thought the great and famous Dean Winchester would be a tougher egg to crack.”

Dean’s jaw clenched. “Are you going to mock me or are you going to get me off this thing?”

“So eager to get started. You, Dean, are going to be my best pupil yet.”

Dean glared but said nothing; he had made his choice.

Alastair moved forward and began yanking meat hooks out of Dean’s body. He screamed at the release of each one and crumpled to the ground when the last one was ripped from his shoulder.

The wounds closed over. Slowly, painfully, Dean climbed to his feet. He felt weak and shaky, but he was free. The torture was over.

Alastair snapped his fingers and a woman abruptly appeared in Dean’s place on the rack. She was sobbing hysterically.

“Here’s your first soul,” Alastair said. “Fresh meat. You, my boy, get the pleasure of being the first one to make her scream.”

Dean looked into her eyes. She was clearly terrified out of her wits. He wondered what she had done to be sent down here. He tried to picture her as a mass murderer or something, hoping it would make this easier.

“Here, boy.” Alastair pressed the hilt of a knife into Dean’s hand. “Show me that you have been paying attention to the lessons I’ve taught you.”

Dean looked down at the blade. It was razor sharp. It would slice through her skin like it was butter; Dean knew because his own skin had been shredded beneath this knife hundreds of times before.

“Please,” the woman sobbed. “Please don’t hurt me.”

Dean hesitated.

“I’m sure you’re aware of this, Dean, but if you don’t do as you’ve been told you will go straight back on the rack. And I won’t be nearly as merciful as I have been thus far. There won’t be any second chances. You will scream for eternity, I promise you that.”

Dean raised the knife.

Please!” the woman shrieked.

Tears welled up in his eyes. His hands shook. “I’m sorry,” he whispered. He lifted the blade and poised it over her stomach, preparing to make the first cut of hundreds.

“Dean, no!”

Dean spun around.


He stared in shock at his angel. The tan trench coat was torn and tattered and covered in blood and gore. The mop of dark brown hair was dripping with sweat.

Dean wasn’t even sure that it could be him. It had been so long.

But he would recognise those blue eyes anywhere.

“Yes, Dean. It’s me. I’m here.”

“Castiel,” Alastair said. “What an unpleasant surprise.”

“Alastair.” Cas spun the ornate knife in his hand, shifting into a half-crouch, ready for battle.

“You really want to fight me again? Last time it did not end so well for you.”

“Get out of my way, Alastair, or I will kill you.”

“Now see, you threatened to kill me once before. Swore you wouldn’t let me hurt your precious Dean as I recall. But you didn’t keep your promise, did you Castiel? Tell me, have you heard the boy screaming for you? He was counting on you to protect him, you know. Even when he had forgotten his own name, he always remembered yours. But you let him down boy-o. You weren’t here when he needed you. And now you’re too late.”


“Dean has made his choice. He is mine now.” Alastair threw an arm around Dean’s shoulders, crushing him against his side.

“Step away from him, Alastair. This is your final warning.”

“So you want to do this the hard way, do you?” Alastair asked. “As you wish. Sorry, Dean, it seems we are going to have to put your torture tutorial on hold for a little while. Pass me the knife so I can dispatch this winged insect, there’s a good boy.”

Dean’s grip tightened around the hilt in a silent and terrified refusal.

Alastair sighed and with a swift movement snapped Dean’s arm. He yelped and his hand sprung open instinctively. Alastair caught the knife out of the air. “Don’t disobey me, Dean,” he said mildly.

Dean was too busy cradling his wounded arm to react fast enough when Alastair suddenly turned the knife on him – it plunged deep into his gut and tore out again.

“No!” Cas cried.

Dean sank to his knees, too stunned to scream. The pain was supposed to be over.

He shouldn’t have disobeyed. He should have known that Alastair would not be forgiving.

“Do not fret, Castiel, Dean will be repaired shortly. I cannot say the same for you.”

Cas lunged forward. Alastair side-stepped nearly and sliced his knife across Castiel’s arm as he stumbled.

“I see your technique hasn’t improved at all,” Alastair observed dryly.

Cas eyed the rip in his sleeve but shook off the sting of the blow and circled around, looking for another opening. He feinted to the left, ducked and struck for Alastair’s stomach. The demon leapt back. Cas swept a leg to knock Alastair off balance but he jumped nimbly over it and aimed a hard punch at Castiel’s face. Cas blocked it and retaliated with a slash across Alastair’s cheek.

Alastair swiped at the blood. “Cute.” He made a curt hand gesture. Cas frowned in confusion –

“Cas, look out!” Dean yelled.

Cas dropped and a hammer narrowly missed his head. It spun through the air into Alastair’s hand.

“Dean, Dean, Dean. You mustn’t do that.” A flick of his hand choked off Dean’s voice. “Now where were we? Ah yes, pest control.”

Alastair swung the hammer and knife simultaneously. Cas avoided both blows but was nearly caught from behind; a glass bottle glanced off his skull and shattered on the floor. Acid sprayed everywhere, hissing and burning where it landed. Dean flinched, cowering away.

All the other instruments of torture leapt off the table and jerked through the air towards Cas, forcing him into a series of evasive manoeuvres. The cat-o-nine-tails ripped across his back but the layers of his clothes protected him. Cas rolled and made another stab for Alastair but a swift deflection meant he barely scratched the demon’s hand.

“Well, you’re good for a work out I’ll give you that,” Alastair said. “But I’m bored of dancing now.”

This time it was Alastair who initiated the attack. He was fast and brutal. Weapons swirled around him in a furious storm that battered Cas from every angle. Alastair stabbed and sliced and cut, striking at every inch of Castiel’s exposed skin to inflict as much pain as possible. He was a cat playing with a mouse before moving in for the kill.

Cas was almost able to hold his own until his weapon was knocked from his hand. It skidded across the floor, out of his reach.

In a last ditch effort, Cas darted in close and slapped his palm against Alastair’s forehead. His eyes glowed blue-

-but nothing happened.

Alastair laughed. “You think something like that works on something like me?”

There was no hope for retreat. Alastair grabbed him around the throat and ruthlessly began to squeeze. Cas scrabbled at the back of his hand but he couldn’t break the demon’s hold.

“I have never had the pleasure of having an angel on my rack before,” Alastair smiled. “I look forward to exploring your pain threshold and finding out just how loud an angel can scream.”

Cas made a choked sound, flailing helplessly. The glow of his Grace spluttered and extinguished, revealing terrified blue eyes.

“Change of plans, Dean-o,” Alastair said, snapping the fingers of his free hand to make the woman on the rack disappear. “You’re going to torture Castiel.”

Dean looked up at his angel. He tried to say ‘No’ but the word wouldn’t come.

“I would think twice before you defy me, Dean,” Alastair warned. “Castiel’s pathetic attempt at a rescue has failed. No one else coming for you. There are only two options for you now. You can do as I say and torture the angel, thus sparing yourself an eternity of torment. Or you can refuse. I will kill Castiel outright and you will take his place on the rack. Whaddya say?”

He waved a hand, releasing the obstruction to Dean’s voice, and waited expectantly.

Five years of torture flashed through Dean’s mind. The only thing worse than the thought of being ripped apart and pieced back together again every day for the rest of forever, was the thought of having to watch someone he cared about suffer the same. He couldn’t do it. Not to Cas. Not after the angel had come all this way to try to save him.

“Do what you want to me,” Dean croaked. “I won’t hurt Cas. Find someone else to do your dirty work.”

Alastair’s face darkened. “Fine. You can watch your lover-boy die slow, then.” He shifted his grip to Castiel’s hair, yanked his head back to bare his throat and laid the knife against his jugular.

In that moment, Dean realised that Cas was going to die.

He couldn’t let that happen.

With the arm that had barely begun to knit itself back together, Dean snatched up Castiel’s discarded weapon and lunged at Alastair.

“Dean, no!” Cas yelled.

Alastair spun.

Dean plunged the knife deep into his chest.

The demon grunted. His eyes widened in shock. Flashes of light jolted through his body.

Dean yanked the blade out and slammed it back in. Agony radiated up to his shoulder. Alastair gurgled on blood.

Dean thrust the knife straight up through his chin into his skill. Lightning flashed. The demon’s eyes rolled back into his head.

The body collapsed and Dean followed it down, stabbing it over and over and over again.

“I won’t – let you – hurt him!” Each word punctuated a blow. “Not – my – Cas – you bastard! I hate you! I hate you! Why won’t you just – die – you son of a bitch!

“Dean. Dean! Stop! Dean you can stop, he’s dead.”

Castiel’s voice broke through the haze. Dean stopped and the world came crashing in around him.

He was covered in blood. The ground was covered in blood. The mutilated body beneath him was barely recognisable as the demon who had tortured him for five years. It looked like a wild animal had torn Alastair to shreds.

I did that, Dean realised. I killed him.

The knife dropped numbly from his fingers.

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