Whiskey River

Chapter 1

It was the same thing each and every morning. Wake up in your small little cell, barely big enough for your rotting cot that you slept on. Getting dressed was easy, a choice of two outfits hung on a peg by the door, both smelling of musty, old blood.

Food wasn't a necessity for a Demon, so you began the short trek to the torture halls. Filing past Demons heading to their own jobs, brushing shoulders, growling as others got too close. Watching as one Demon threw another over the bridge into the river of lava, it's screams dying quickly.

The Demonic work rush was always a thing of nightmares, and you often tried to get to work before anyone else. But today you had laid there on your hard cot, staring up at the leak in your roof, thinking. Seeing a pair of haunting green eyes pleading with you to stop. Amazed at how true the stories about Dean Winchester had been. He was strong, and brave, and more fearsome than any other man you had met before. Besides Alistair.

You hoped that you wouldn't have to torture him today. That you could get off with the greedy businessmen, and the stuck up models that had traded their souls for looks. They were easy to torture. A couple of mind tricks, a slash or two of the blade and they were a quivering mess. It was a mindless job, and that's exactly what you needed today.

"There's my favorite Demon!" Alistair exclaimed as you entered the main room. Hallways led off four different ways, a couple of desks in the middle of this circular room. Screams were already heard, a sound you had easily grown accustomed to. "I was getting worried. My favorite torturer is usually never on time."

"I was just planning new ways of torture," you lied, watching as his face lit up. To Alistair everyday was like Christmas. There was nothing he liked more than flaying the skin off of a helpless soul.

"That's my girl! And perfect timing because I have you torturing the one and only Dean Winchester again."

"Really? I was thinking you would want a crack at him," you mumbled as the two of you began the trek down the main hallway. It was reserved for the top torturers, those capable of handling the worst souls. It's where you had been working for the past hundred years or so.

"I do...I do..," he spoke in that creepy voice of his. "But I'm afraid I will busy most of the day. Meetings with the king of hell and such. But I do expect a full report of how it went today. And remember, this is Dean Winchester we're talking about. Even down here he's very dangerous and needs to be taught a lesson."

"I understand," you answered, not sure you could face Dean again. Sure, you were a hardened Demon who had tortured thousands of lives. But Dean was different, and that scared you.

"Oh and Y/N?" Alistair called out. "Maybe the special cat of nine tails that I made you! And some mental torture would be great as well!"

With that he left you standing there, staring at your usual door. Trying to remind yourself that it was just another day at work. That Dean was just another soul. Reaching over, you pulled the new weapon that Alistair had specifically made. Much like a normal Cat of Nine Tails, this one had razor sharp wire balls. They did horrific things to skin, getting stuck and ripping skin out in shreds. You had only used them twice, leaving them for Alistair.

Hanging heavy in your hand, you stepped inside, your eyes always accustomed to the darkened interior. The smell of brimstone and sulfur a comforting smell as you stepped forward, seeing Dean tied up on the rack. "Hello Dean," you spoke, letting Dean see the scary weapon you were currently holding. "Ready for another day full of misery and agony?"

"You can go to hell," he spat. "Oh wait, we're already here. Do your worst, you won't break me."

A part of you hoped that was true. You didn't want to see this proud man broken because of you. But you still had to do your job. Gritting your teeth together, you raised the Cat, swing it with an easy flare. The wires immediately caught in his skin, ripping it like it was paper. Dean cried out, his eyes never wavering from your face as you pulled on the weapon.

Again and again you hit him, watching as his skin ripped, his blood poured to the stone floor below. When you couldn't handle it anymore, you left the bloody Cat on the floor, Dean hanging his head as you stepped into the hallway.

Leaning your head back against the cool stone, you took a couple of deep breaths. Trying to remind yourself that he was just another soul. That there was no reason he should be getting to you like this.

"Y/N!" Another voice called out, and you turned to see a tall, lanky brown haired Demon making his way towards you. It was Everett, one of the other seasoned torturers. "Alistair said you would need help."

"He did?"

"Something about mentally torturing a soul," he explained. "Said it's a big deal. Who do you have in there?"

"Dean Winchester," you muttered, taking a deep breath.

"No shit! So, how are we going to torture him? Brother, Mom...?"

From your brief knowledge of Dean, you had an idea of what would hurt him the most right now. "I think we'll have to go with Dad. Show Dean that his Dad is getting tortured, before getting off the rack and torturing him as well."

"Ooh, I like! What do you want me to do?"

You knew you had no choice. You had to go through with this. "I want you to torture me. I'll be his Dad."

With the details figured out, you quickly transformed yourself into a version of Dean's Dad. With the lean build, the salt and pepper beard, you could see where Dean got his good looks. Letting Everett tie you to the rack, you stayed silent as he willed you into the room.

"Wake up stupid human!" Everett screamed, splashing Dean with water. Dean came to, sputtering, his eyes growing wide when he saw you, or rather his father, tied up in front of him.

"Dad?"

"Dean, what are you doing down here?" You asked, your voice so much deeper than normal.

"Hellhounds. But I thought we freed you," Dean cried as Everett moved closer to you, holding a wicked looking knife. It would hurt you, but you would heal quickly.

"This is going to be so much fun. Letting you watch as I slice your Father to shreds," Everett muttered, running the knife along your cheek, slicing deeply.

"No! Stop! I'll do anything. Just leave him alone. Please!" Dean pleaded, pulling at the ropes and hooks holding him.

Everett ignored him, slicing what looked like Dean's Father. Dean continued to plead, his voice finally going hoarse before you decided it was enough. Giving Everett the signal, you watched as he dropped the blade, untying you. "I give in! I'll do whatever you want. Please!"

"The tortured becomes the torturer," Everett said, pointing towards Dean who watched with wide eyes.

Smiling wickedly, you picked up the knife, saddened at the look of dismay in Dean's eyes. Pain didn't break him, but something like this certainly could.

"Dad, please! You don't have to do this," Dean pleaded with you as you raised the knife up high, slamming it down in Dean's shoulder as hard as you could. His scream was loud, echoing through the stone room as you pulled it free.

"Oh, but I want to," you whispered. "Dean, you have been nothing but a disappointment to me. This is what you deserve."

Taking the knife, you slid it across Dean's arm, watching as tears slipped down his cheeks, knowing that you had finally taken the brave hunter down a step.