Author's note: Do you like adventures through Hell with a 91748492568403% chance of never coming back? Yes? So do I! So here's your story:
Elena stumbled at first, her new surroundings surprising her. She was in hell, all right, but not in chains like last time. She looked around, slightly afraid of what she would see. Nothing appeared to happen, so she took a step forward.
Again, othing happened, and she began moving at her normal pace, checking out the room she was in.
She hadn't asked Cas where the book would be.
"Shit." She said, and she ran a hand through her dark mess of hair.
"Cas! A little help? Where's the Enchion?"
She felt his presence in her mind.
'Right now you're near Crowley's "throne" room. It will be somewhere near there. They have to have a sort of treasury.'
She nodded and felt him leave. Her surroundings were silent except for the soft rumble of voices from outside the room.
She leaned into the door, straining her ears. She heard the accent of Crowley, along with another demon, who seemed Irish.
She tried to make out their conversation.
"-need it anyways!"
"She's still here. So find her, and everything is resolved. She's dead, the book's secret is dead." She heard Crowley speaking.
"If we kill her, they'll just send someone else."
"Then kill them. Kill them all." The King responded.
She heard no noise after that, and she opened the door a crack. Looking around, the 'throne' room was empty.
She tiptoed into the room, spotting the king of Hell's chair in the back center of the room. She looked at the pillow seated on his throne, and she smiled wickedly, glad to have enough time to mark it with a demon trap.
Making sure Crowley's ass got stuck to that pillow became one of her top priorities, behind finding the book and getting home safely. She cut the tip of her finger barely, using one of the knives in her pockets. She drew the trap carefully on the bottom of the pillow, wishing she would have the chance to see Crowley walking around with it stuck to him.

"Remove this. Now. I am your king. I command you." She mimicked his accent, and placed the seat-pillow back where it was originally, hoping he wouldn't notice it had been moved.
She moved to the other side of the room, opening the door in the front of the room barely a crack, her having come from the back-end of the throne room. She spotted no demons, and so she walked out, making sure to hide behind crates and boxes occasionally.
"Cas! Which way?"
'I'm not familiarized with Hell. They wouldn't keep it here though. Its power is too holy. They'd keep it in a quarantine cell of some sort.'
She nodded, and started moving a little faster, checking each turn before making it, and looking for doors along the way. It seemed to just be one long, empty hallway.
She jogged to the exit, trying to listen to the other side of the door. What she heard didn't make sense, so she opened it up, expecting a machine or something. Instead, an office full of workers typing away on computers, making calls, and taking lunch beaks in their cubicles sat behind the door. Upon closer inspection, each worker was in fact a demon. "So this I what keeps Hell up and running..." She mumbled, not surprised.

A man in an all black suit approached her. "Are you the new-comer? You're in prison hall."
"What?" She asked, confused.
"Well get down there!" He said, patting her on the back, and then he looked her up and down, then back up to meet her eyes. "Where have I seen that jacket before?" He asked, his eyes narrowing as if trying to recall
She tugged Dean's jacket defensively around her, and even though it was far too big, it felt perfect.
"I don't know. But it's mine." She stomped off towards the sign that read 'prison.'
To think, this was what Hell was really like, behind the whole torture thing.
She swung open the door carefully, peering into the prison holdings. If this was where the humans were tortured, couldn't she be harmed easily if she stepped foot in there?
She took a hesitant step forward, and she was teleported somewhere else.
"You don't have the stomach for it." Dean stood in from of her, and she walked around him to see Sam holding a knife to his brother's throat. Dean was a demon. Sam pulled the knife away from his brother's throat, as expected, and she was sent somewhere else.
John Winchester walked through the forest, his boots crunching in the leaves and twigs. She walked behind him, nowhere else to go, and they came to a clearing, a bloody mess. Some large animal sat in between two children, and it seemed the animal had exploded. One child was simply standing there, scared, while the other, completely terrified, was on the ground, looking up at the other boy. She then realized the boy on the ground was child Dean, soaked head to toe in blood. The other on was Sam, also covered in blood.
John looked towards Sam as if he was a monster, first asking Dean if he was okay. It was easy to see that Sam had done something, him standing there, crying as Dean was helped up. "I'm sorry!" He said, tears flowing faster, as she was sent to another memory.
She ended up in a nursery, a crib with a baby who was crying. A man stood over the child, and he held a knife. She gasped, but her hand traveled through him as she tried to grab him. It was a memory. She couldn't stop it.
He then slit his wrist, and she was confused until he held the blood to the child's mouth.
Sam. This was his Hell she was experiencing.
The demon's eyes were glowing a bright yellow as the blood dripped onto the child's face and into his mouth. She heard soft footsteps coming from the hallway, and the door swung open to reveal Mary, her face struck with horror. "Sam!" Se shouted, running towards the demon. He flicked a wrist upwards and she was flung up to the ceiling, pinned there. "Sam!" She shouted again, this time it sounded like she was choking.
Fire erupted around her, and she was engulfed in flame, setting the roof around her on fire. Her nightgown billowed around her and Elena covered her mouth, pain surrounding her chest. Sam would have to see all of this. Sam still thinks it's his fault. John had entered by the time the demon was gone, and he looked horror struck, grabbing Sam and forcing him into Dean's arms. "Dean, take your brother and run." He commanded.
"But, Dad-"
"Just do it!"
Dean nodded and ran with Sam out of the house and onto the street. John had dropped to his knees, yelling angrily, holding his head in his hands. "Mary!"
She almost fell over as she came back to the Hell prison. That's what Sam would see when he died? She peered down the hall. Would she have to see more? She didn't want to watch any more of that, it was torture enough to know Sam would be shouting and crying.
She took another step forward, carefully, and was glad to see she was fine. She looked at the different prison doors, names engraved on each one. One caught her eye, and she read it.
'Sam Winchester'
Is that why she had seen those things? Her hand ran over the door and it changed suddenly to 'Chelsea Reiner.' She had no idea who that was, but she felt bad for the girl who had to go to Hell.
She ran her hands over the other door names and they all changed. There were six doors in total, three on each side, as well as a door at the back of the hallway and the front, the front one she had entered from The end door was locked tightly when she tried the knob. Either way it would have to wait. She focused on a specific name, and wiped her hand across one of the labels.
'Dean Winchester'
He had come back and acted so strangely, not once giving them any insight as to what he saw. He was still sensitive about it. She hoped they couldn't see what exactly she was doing as she opened the door.

"Cas, where is she?" Asked Dean as she disappeared again.
"This isn't supposed to happen." The angel mumbled, checking over the portal. Sam looked down into the black, thinking. They were all in silence as she reappeared, almost five minutes later.
"What was that?" He asked, watching her look of confusion and shock. They watched her staring at the doors in the hallway, rubbing her hand across them repeatedly. She then shut her eyes next to a door, looking like she was concentrating as she drew we hand across it. She looked around, opening the door, and she disappeared again.
"Cas, can you rewind or something like that?" Dean asked.
"I can alter time in the portal to see what was on the door." He said, and he reached an arm into the black, twisting his arm a few times. When he retracted his hand, it was changing their view to the inscription on the door.
'Dean Winchester'
"What does that mean?" Asked Dean, looking down at it, confused.
"Behind that door is your personal Hell. She's a human, so she's easily pulled into the torture of Hell. She may pretend to have a reason to go in there, but the real reason is the influence Hell has on humans."
"I thought she wasn't human any more?"
"But she till has that essential element. Emotion."
She looked around for any sign of Dean, and then she spotted him, holding Sam's lifeless body. She was sent through scene after scene of Sam hurt or dead in his arms. Tears flowed down her face as she watched each painful memory, Dean's sad expression the same almost every single time.
The Impala was now in front of her, and John was speaking down to Dean.
"I wouldn't have given you it if I knew you'd break it." He was complaining about the rust that wasn't there on the car.
Dean's memories of his father weren't the brightest ones. She watched each one in turn, him yelling at Dean to go faster, dodge quicker, to do it already. Why did Dean respect his dad so much?

Then she saw Dean as a terrified child as he sat on the street below his burning house, baby Sam in his arms. John and Mary were still inside, and he was crying. He was a child, and he was driven to this, forced to watch their house burn, not knowing what was happening to his parents inside the fire. Dean looked up suddenly, sniffing. "Who're you?" She looked down to see him speaking straight to her.
"I'm Elena."
"Where'd you come from?" He held Sam closer, protective. She bent down next to him.
"Dean, you and Sam will have a lot to deal with in the future. You're lives will be hard, and you'll struggle every day. But promise me you won't give in. You'll struggle through those things, and meet me in Michigan in 20 years, April 29th." She hugged him close, and even though he was tense at first, he began to feel safe in her arms, and she was pulled away from him as she traveled to another memory.
"Bye Elle!" He called.

The blackness glowed red for a moment, and Castiel's eyes widened. "Something happened." He reached his hand into the portal again.
"Dean do you remember the night you brought Sam out to the street when your house was burning down?" He asked.
It pained the hunter to recall it, but he nodded. "Yeah, so what?"
"She changed something. A burst of her emotion altered something in your past or in your Hell."
He remembered that night clearly. "I ran outside, sat on the curb and waited. Nothing else happened."
Castiel nodded. "Your Hell then. She's managed to alter your hell and speak to your past self. Even though you don't remember it, now it's happened."
He was surprised, looking into the blackness. Cas grabbed his arm, pulling it touch the black. "You can see."
Dean's eyes stopped showing him the room he was in. Now he was watching Elena hugging a small child who sat on the curb of a street, a small child in his arms. The house behind them was on fire, and he knew this was his memory.
Dean couldn't help but smile, a laugh bubbling up in him. He knew his Hell would transfer back to it's original state, and Elle probably didn't know what she was doing anyways, but he felt pride and love watching her encourage him. Each bad memory she was sent to after that, she faced with tears in her eyes.
Someone grabbed his shoulder, pulling him out.
"If you stay any longer like that, you'll be pulled in." Cas said, looking down at the black. It faded back to Elena, who was now walking towards the door in the back of the hallway.

Elena tried the door knob again, but it didn't work. She rammed into the metal door, trying to knock it in, but then again, it was a metal door.
"Dean, let's hope you a least packed..."
She reached into the pockets of the jacket, digging around in the pockets. She found a knife in one, holy water in another, and a flashlight in one of the inside pockets. The rest were empty and there was nothing left to search.
"Damn... Nothing to pick the lock."
She placed a hand on the door knob.
I'm supposed to be connected to this book of Enchion... She thought, trying to figure out a way to use that. She looked up suddenly.
"Cas!" She shouted excitedly. "Get Dean to open a door!"
'Why?'
"This blood bind is the only way you can get to the book." She replied.
'He's going to open one. When should he?'
"Three... Two... One...Now." She twisted the door knob at the same time he hopefully was, and the door swung open, the handle making a complete turn.
"Thanks angel." She whispered, sliding into the room. There was no light, so she used the flashlight Dean gave her in his jacket. She did a scan of the room with it, then found it to be empty except for a chest in the back. She approached it, kneeling next to the opening. She placed both of her hands on the trunk, pushing up until it popped open with a small click. She looked inside. The book sat alone in the bottom. She collected it, pushing it into the jacket, between her arm and chest.

She returned to the door, walking out of the room, and coming face to face with the demon that had greeted her before.
"What were you doing in there?" He asked, annoyed and tapping his foot.
"I...uh-"
"It doesn't matter. The King requires your assistance. As our new prison guard, you have other duties too."
"Shit." She said, and he dragged her along towards the throne room.
"I know, shit shit shit, we're going to be late!"
She was dragged along, helplessly.
"Cas?" She questioned.
"You'll get your cash, just hurry up!"
'I can't pull you out. The only way for you to get out is being resurrected again. Unless a demon sends you to the surface.'

"Likely." She mumbled.
Elena then pushed the book deeper into the jacket.
"Could I use the restroom first?"
"Restroom? Oh right, you're new. Demons don't need to use the bathroom." He continued to pull her by her hand. When he pushed open the door, and no one was there.
"Hmm... Guess he already left. You'll have to wait for his return. In the mean time, I need help catching up on my work if you'd help."
Anything to get her mind off of the worry she was feeling. How soon before she gets out?
"Of course." She said, following him to his office, where he handed her a stack of paper work.
"I appreciate the help." He said. "Just fill these out using this information." He handed her a pale-yellow file folder, then sat down at his desk, typing away onto the computer.
She looked down at the papers. They were all contracts for selling souls. She wrote down the assigned numbers of the different demons, writing out the human's name and what the deal was, based on the report from the demon in the deal. She noticed most of the cases were stupid.
'Sold soul for beauty'
'Sold soul for a more exciting job'
'Sold soul for money'
'...for skills in acting'
'...for better athletic ability'
'...for abs'
She laughed at the last one, and he looked over to her, questioningly.
"Why do people sell their souls for this shit?"
"We don't tell them it's their soul. We tell them 'we'll come to claim what's ours in ten years.' That way there's not much question. We tell them it's a 'small price.'" He did smile amusingly though, when she pointed out some of the ridiculous deals people had made.
"So what deals have you heard of that weren't on paper?" He asked casually, hoping she's heard some of the exciting ones.
She was careful, because if she didn't reply about any, he'd be suspicious, but if she gave too much away...
"Of course I've heard of the Winchester's deal with Lilith."
He nodded, pleased with her answer. "One of our greatest soul collections. Although I do miss having Lilith here… Did you hear about the massacre we performed in Romania?"
"Yep." She lied, feigning a laugh with him.
"We gained so much power after that. All those people sold their souls for the same exact thing. And they all dropped dead ten years later."
She nodded, agreeing. "So... I've heard rumors..." She prodded. "About reversing deals, so that the human gets their soul back but keeps the benefit of the deal. Is that true?"
He looked strange. "Who told you that?"
"Lots of demons outside of the office are wondering." She lied through her teeth again.
"Well... If those papers were changed, then it could be entirely possible for that to happen."
She nodded. "So if someone just typed up 'brother comes back to life', that'd be considered a full contract?"
"Yes. The exact reason Crowley, our King, created this place. We're here to keep track of and mostly protect the contracts."
"Then who created the office setting?"
He shrugged. "Maybe the King or someone enjoyed organization and mild humor. 'The office of Hell.'"

"Any other questions?" He asked.

"Yes… What's one way to reverse a demon back to a human?"

He looked up suddenly. "Tell me you aren't planning-"

"No, no." She said, laughing. "I'm just wondering."

"Well, human blood was recently found to work." He leaned in closer to her "Also, recently we discovered that if a demon suffers extreme emotional trauma, he'll be drawn back to his original human form."

She nodded, her eyed asking if there was more.

"I'm not entirely sure on the details, but one man killed his entire family except for one. That one suicide, and he lost it his demonism. He became a human because everything he loved had been destroyed."

"Hmm." She commented.

"I'm sure it's a rumor though."

She barely smiled, nodding, but her eyes showed she was thinking for more than she was paying attention.
He noticed, and he waved a hand in front of her face. "You know, you're really curious."
"Sorry." She muttered, snapping back to reality.
"No, it's fine. I enjoy the company. You should help me more often."
Helping him meant spending her time in a small room, out of sight, with a person who didn't entirely act like a demon should. It was better than suffering the memories down in the 'torture hall', or possibly spending all her time in frickin cubicle.
Elena nodded. "Do you already have an assistant?"
"Actually, last month he was killed by hunters in Colorado."
"Oh." She distinctly remembered killing a demon in Colorado last month. "Oh." She repeated.
"So there's a position open if you'd like it."
"Sure." She said, even though she was completely disinterested.
He held out a hand, and when she took it, he shook it vigorously. "Thank you so much! Your first job will be after you finish those." He pointed to the stack and then typed away with a new energy.
She sighed, then continued with the work.
Cas. Can you still hear me?

"Elle. The portal is closing. We can't watch you anymore, and I won't be able to reach you."
Dean grabbed Castiel by the shoulder of his coat.

"Why is it closing?" He asked, and Sam held him back as Cas closed the view of Elena with a swipe of his hand.
Dean struggled against his brother's grip, close to breaking free.
"What did you do?"
"Dean, it had to close or Nicole would die." Sam told his brother, struggling to keep him back from Castiel.
Cas looked to Dean apologetically. "She says she'll be back soon."
Sam released Dean, exhausted, who went to tackle Cas, but the angel was gone.
"Damn it!" He shouted.
Nicole sat up suddenly. "Where's the hot guy?" She asked sleepily, then fell unconscious again. Castiel reappeared, now that Dean had slightly calmed down.
"She'll be asleep for at least a week. She'll be fine though. She won't require nourishment until she awakes."
Dean left, still steaming, and him and Sam climbed into the Impala, leaving Cas behind, so he could travel back to Heaven.
"Dean, she said she'll be back."
"Of course she said that, Sammy. Elle will lie until the angels cry if it means keeping us safe."
"You need to relax."
"I can't relax when she's down there alone with things that would love to kill her. How long until she gets out, Sam?"
"Cas said it could take only a day."
"Or months, or years." Dean added, staring only at the asphalt of the road ahead.
The motel was in sight now, its shabby and rusted neon sign was missing a few letters, but the stain was left to distinguish 'motel' from 'm_te_'
He pulled into the parking lot, Sam completely silent, not wanting to upset him.
"The things I said to her today, before we left… The argument Elle and me had... You think she was acting at the house so nobody would notice she was all sad and stuff?"
"No." Sam said, "Elle wouldn't be able to fake that. She really loves you, Dean."

"But why? I mean how can you love someone that screws up as much as me? I mean, I'm a dick, I'm annoying, I do all these bad things and she'd fine with it."

Sam didn't respond, knowing his brother would deny all possibilities.

The driver turned on the radio, filling the car with classic rock, knowing their arguing normally would have ended up with a smack in the head for both of them from Elena.

Elena wrote down names and numbers for why seemed like hours, until she finally finished. "Done. So, what am I doing next?"
He didn't look away from the screen. "I'm sending you to collect souls under my name."
You mean..." She pointed towards the roof. "Up there?"
"Yes, the surface. I already have a few set for you." He placed a sticky note in front of her, and she read over it.
"Coordinates?" She asked, looking at the numbers closely.
"Just teleport to each location and you should be back shortly, I hope."
She would make her escape then. She nodded. "So how do I get out of here?"
"Like this." He hit the enter key on his key board and she was suddenly sitting at a bus stop, a homeless man beside her. He looked surprised by her sudden appearance.
"Who are you?" He asked, scooting away from her.
"Excuse me sir, what state is this?"
"Ohio." He replied, then deciding he had imagined her teleportation, he looked away.
She nodded slowly. "Thank you."
She stood, walking towards the nearest corner. A taxi was pulling away from the stop light and she jumped in front of it, then once they stopped, she climbed into the back.
"Which way?" The driver asked, as Elena dug in her pockets for cash. "How much to get me to Michigan?"
"Michigan?" She asked, her eyes widening greatly. "Do you know how far that is?"
"No idea."
"We'll get there at seven if that gives you any clue!"
The time was now 5:00.
The driver seemed to consider something. "It'll cost at least a hundred."
"What?"
"No... Two-fifty. I need gas payments."
"150 dollars for gas?" She asked, knowing the driver was full of shit.
"You heard me. It's a long drive and I have a family to get home to. She looked Elena up and down. Actually, that jacket would do nicely."
"Hell no." She practically growled, glaring in a way that would scare anyone. The driver instantly backed off. She pulled the jacket tightly around her.

Elena was ticked, but she took off her necklace, one her mother had given her. "Just get me there. I have family waiting too." Dean would have been upset and insisting she gave away the jacket instead, but why should she care? Her mom was dead anyways.
The driver stared down at the silver-emerald jewelry. "How much is it worth?"
"More than your life. Now drive."
The driver sped off in fear, hoping to make record timing to please her customer.
Elena drew the book from the jacket, opening it up to a random page. She looked down at the strange symbols, confused.
"The Enchion is in Enochian?" She mumbled. She didn't realize how closely the names were related until now.
She flipped through the pages, but didn't recognize anything. No English, no pictures. She sighed, tossing the book into the seat next to her. It was hopeless. She'd have to wait until she could call on Cas without scaring the living shit out of the taxi-driver… again…
She looked out the window for the rest of the ride, hoping Sam and Dean were still in the same motel room.