After re-watching 'On the Head of a Pin' recently, this whole idea of Dean's will being broken, thus breaking the first seal, really struck me so I wanted to write what I imagine happening in hell to get Dean to that point. This is what I consider a 'Chuck Fic'.

Dean's wrists were badly chafed. He suspected his ankles looked the same, if not worse. He wasn't sure why he bothered fighting against the chains that held him to the rack just loosely enough to allow for some struggle but never enough to actually do any good. It had been weeks, months, years… maybe even decades, but still, he couldn't help himself. He had to fight against the pain. It was as natural a reaction as squinting after stepping into direct sunlight.

Sunlight. How long had it been since he'd seen that? Somehow that felt even longer ago.

He'd kept count for the first year. He would whisper it under his breath at the end of each day, at the end of each session. When Alastair laid his razor down on the table of instruments he kept close, Dean would grit his teeth and, through the blood in his mouth, groan out the number. The last he recalled saying was 368.

On day 369, he couldn't remember what yesterday was. Every day contained the same thing so he was surprised he'd kept track as long as he did.

"369," Alastair said when Dean didn't. His voice was unnaturally sympathetic. That startled Dean more than what he said. "It's day 369, Dean." He'd sobbed that day. Not that he hadn't cried before here, but this time it wasn't because of the pain—not totally, at least. Hearing his name said softly, almost kindly, broke his heart completely.

How long ago had that been, Dean wondered. Day 369 became 370, then it was 400, then he gave up keeping track when he realized that he had started counting because he believed it would end one day. But it wouldn't. This torture, this excruciating pain, it would never end.

On whatever day it was this time, Alastair glanced at Dean, returning from cleaning his blade on an already blood-soaked towel nearby. Dean's jaw clenched tightly, the only pain he could control, and his eyes shut. His hands balled into fists and he tensed, knowing exactly what was coming. The day was nearly over, he never knew how he knew that but somehow he just did, so Alastair was cramming in what he wanted to finish before time was up.

The razor cut into the flesh just below his ribcage and, though he tried to keep silent, Dean cried out until his throat was raw. Or at least more raw than it had been at the start of the day. Water, or better yet whiskey, was unheard of down here. He knew screaming was just as useless as fighting, but he was powerless to stop either. No one would help, no one seemed able to hear, except Alastair.

Not that Alastair was the only one who took pleasure in Dean's agony. Others came, some demon, some human on their way to becoming demons. But today it was just Alastair.

Finally, the master of torture stepped back, tilted his head, and smiled. He was hideous in every way, his un-vesseled form, but his smile made the ugly, evil face even harder to look at. Dean refused to open his eyes, instead hearing the smile in Alastair's voice when he stated, "There. I think that's quite enough for one day, wouldn't you agree?"

Then, the same sounds he'd heard every night since he awoke here, suspended and chained in the abyss: the familiar metal-on-metal tick of the razer being placed on the table; a few footsteps; scribbling; Alastair's notebook closing; more footsteps, nearing this time. Dean knew what the demon would say next and he knew what he had to say.

But yesterday something had changed. He'd felt his strength waning. Not that he had any left, but his reserves, the ones buried way down deep, were failing him. Years upon years of this had stripped away every ounce of resolve he had. And yesterday, when Alastair offered to take him off the rack, Dean hadn't replied. It was the first time that he couldn't find the will to say 'no', or one of the many other sarcastic responses he'd come up with. Instead, his silence spoke for him and Alastair returned the next morning with his tools and evil smile.

Dean couldn't open his eyes if he wanted to look at the figure hovering over him, taking stock of the damage the demon had inflicted. Dean couldn't recall ever being so exhausted. He had endured so much pain, he was at his breaking point.

"Did you know it's our anniversary today, Dean?" Alastair asked, his voice just above a whisper.

Dean could barely breathe, his body torn to shreds, but he fought to focus on the words. What could it be, five years? Ten? Twenty?

"I know, you wanted to get me something special to celebrate but you've been just so darn tied up lately." He laughed. Dean cringed. "Don't worry, I got you something special."

Alastair leaned in even closer as Dean angled his head as far away as he could manage. "I was thinking tomorrow, we get… a dog."

Tears burned behind his closed lids and one escaped down his bruised cheek. His fists ached but he couldn't release them. He imagined breaking these chains and… and what? There was no getting out or getting back to earth.

And Dean knew what kind of dog Alastair was referring to. A hellhound. It wasn't the first time Alastair had let the beast at Dean but it had been a while—that was one thing Dean was thankful for.

"Oh, bother, I shouldn't have told you. Now you're so excited you won't be able to sleep," Alastair teased, straightening. "Unless, of course… you don't want to." He almost sang the words. "You know, if you wanted to get out of here, we could go somewhere nice to celebrate."

There it was. The offer. Cruelly disguised as freedom, but it was there all the same: get off the rack and take Alastair's place. Stop being the victim and start on his path to becoming a demon.

Alastair waited patiently. Moments passed and Dean said nothing. He couldn't speak. He wanted to decline, scream it, shout it, spit it, but nothing came out.

"Alright," Alastair finally replied, an odd mix of pleasure and disappointment in his tone. "Then I will see you bright and early tomo—"

"How long?" Dean didn't recognize his own voice but he knew from the grating in his throat that he'd managed to speak.

"I beg your pardon?"

Dean swallowed painfully. "How long?" He forced his eyes open and tried to look Alastair square in the face.

The demon smiled. "How long have we been together? Why, Dean, I'm hurt. I thought you were keeping count this whole time." He waited, expecting a snippy reply, but Dean had nothing to say. Sighing, Alastair replied, "30 years."

Dean could have fainted. If it was earth and the natural rules applied, he would have. 30 years. To some extent, he couldn't believe it had been so long but he was equally as shocked that so little time had passed. It felt like an eternity already. How could he possibly endure more, much less more without end?

His thoughts shifted to Sam, the only comfort he found here. Was he happy now? If 30 years had passed, Dean could believe that Sammy had moved on and had been able to forget about him. He'd be over 50 now. Dean almost smiled at the mental image of his brother with thinning hair and—

"And no, Sam isn't an old man now."

Dean froze.

"You see Dean, time's different down here. Oh yes, it's been 30 years here, but it's only been 3 months up there."

That statement, whether true or false, burned the last atom of strength Dean had left. He couldn't fight anymore. He had fought for 30 years. 3 decades to the day. And he couldn't take it any longer.

"Well, I'll just be going now."

Knowing the satisfaction it would give Alastair almost made Dean keep quiet but he also knew what would come tomorrow if he didn't. "Wait."

Alastair stopped at the door, his hand on the rusty knob. He didn't look back. "Yes, Dean? Something you need?"

Dean closed his eyes against the spinning room. His heart slammed against his ribs like a sledgehammer. He was giving up and his body, or maybe his soul, hated him for it. "I'll do it."

The footsteps approached again. "I might have some blood in my ear, Dean, so could you repeat that? I want to get it just right for my diary."

"I said… I'll do it." His voice was still unrecognizable to him. It was weak, unsteady, raw, just like the rest of him. It suited the victimized, abused man he'd become.

Then suddenly, he was that man no longer. His hands relaxed and the agonizing tension in every muscle eased. This had happened a million times before but this time the 'healing' felt different. He felt like himself again; powerful and capable, young and alive. The chains fell open as Alastair snapped his finger and for the first time in 30 years, Dean was free from bondage. He sat up slowly, cautiously. He felt sure that this was a trick, that the chains would close again around his limbs and he would be stuck again, left to contemplate his absolute aloneness until Alastair returned.

But it didn't happen.

He swung his legs over the side of the cold metal rack and his torturer stepped back, giving Dean space. Dean couldn't shake the unease he felt as Alastair watched him like Alastair was a starved monster and Dean was his lunch.

Even though he was whole again, uncut, unbloodied, Dean's legs were not what they once were and his knees buckled when his feet touched the floor and his weight shifted. He held onto the rack and cursed. Alastair abruptly walked to the other side of the room to a cabinet that Dean had never seen open. Swinging it open and revealing at least a dozen bottles of liquor, Alastair glanced back. "Can I interest you in a drink to celebrate this momentous occasion?"

Dean's mouth watered and his stomach growled at the sight. He was proof that food and drink wasn't a necessity to survive in hell, he hadn't eaten since his last meal at Bobby's house, but he still craved it.

Alastair selected one and moved to the door. He opened it and called, "Bring her in." Dean watched in shock as two demons dragged a woman in, wailing and begging. Dean moved away from the rack in horror as she was strapped into the space he had filled for the past decades. She too fought against the restraints uselessly, crying, her eyes darting around the room. She was as panicked as he had been his first day in this God-forsaken room.

Dean turned away from the sight, covering his face with a shaking hand. He knew what was expected of him, what his end of the bargain was for the woman taking his place. But he had spent his whole life helping people, saving them from monsters. Would he really become the monster now to spare himself?

"Oh Dean," Alastair sang above the woman's shrieks. Dean slowly, almost against his will, looked at the demon. Alastair held out the bottle of liquor but Dean wasn't unaware of what Alastair was really offering him. His free hand rested over his razor and he tapped his finger impatiently on its handle. "Come on, grasshopper, it's time to get started."

Resisting the urge to vomit, if that was even possible in hell, Dean yanked the bottle from Alastair's hand, broke the seal, and drank it greedily. He could barely stop but he needed air. Lowering it, he inhaled deeply, gruffly. Perhaps this was when the real torture began, he considered. Maybe there was a way to get free, to—

Suddenly Alastair was directly beside him, his hand tight against Dean's throat. "I know what you're thinking, Dean, and before you think it a moment longer, I want you to know that if you don't pick up that blade and do exactly as I tell you, you will spend the rest of your days on this rack without another offer. And don't forget, 'the rest of your days' is really just a figure of speech. You understand me?"

Dean understood perfectly. This was his only chance to be free of an eternity of suffering. He nodded once.

Alastair released him and moved away, close to the woman. "Hello, my dear," he swooned. "You are in for a real treat, I mean a real treat. You see this man, oh he's really something special, dear. You might even say he's a virgin and you're going to be his first. Yes, this is going in my diary for certain. Now come on, Dean, let's not waste the lovely girl's time, can't you see she's ready and waiting?"

Dean finished the bottle. Slamming it down, he heard the woman cry out in surprise at the noise before continuing to sob, begging Alastair to let her go. Dean wished he was deaf. And blind.

With a trembling hand, he gripped the blade and turned. She eyed the razer and screamed even louder than before.

Alastair grinned. "That's right, come here now."

Dean didn't remember much of what happened next. He listened to Alastair's instructions, where to cut, how to cut, what places on the body produced the most and least amounts of blood, and so on. To Dean's disgust, Alastair was teaching him.

Something in Dean's mind switched 'off' that day. And it was at the exact moment that Alastair's blade, held tightly in Dean's own hand, sliced through the woman's skin, drawing the most fear-filled cry he had ever heard. But she wasn't afraid of Alastair. She was afraid of Dean.

To protect himself, he imagined, it was as though his humanity turned away and all that was left was the wounded animal who finally, after 30 years, had the chance to inflict pain back. He couldn't hurt Alastair, but he could imagine that every soul placed before him was the demon.

And instead of counting the days, Dean began counting souls. Until he lost count of those, too.