I've decided to change to a narrative for this chapter (and possibly others) in order to get a good feel for ALL the characters. The next few chapters I'm planning on going into some side stories and it'll be easier if I just do a narrative.

CHAPTER SIX: Welcome To Hell

As Dean stared wide-eyed at his brother, his fellow inmates stared at him with worry.

"Dean?" Jo asked tentatively, her eyebrows creased with concern.

The eldest Winchester couldn't help himself. He had to be positive it was his brother or he'd drive himself crazy. "SAMMY."

Sam and Dean made brief eye contact before Ruby shoved the youngest Winchester forcefully into his very own cell right next to Bobby, the door closing with a final clank that echoed against the dark walls.

"Wow, you just seem to know everybody." Cas quipped from his position on his cot.

"Fuck off, Cas." Dean spat, not in the mood to deal with the hormonal angel especially when he saw Ruby sauntering her way towards him.

As she stopped in front of Dean's cell she leaned forward to rest her arms on the horizontal bars, a sense of confidence coming off her in waves. "Are we having fun yet?"

The eldest Winchester banged on the bars, getting as close to Ruby as allowed with his nostrils flaring. Dean's voice dropped dangerously low with a warning in his tone as he spoke. "I swear if you touch him, I'll kill you myself. And trust me when I say this, when I make a promise, I keep it."

As the demon looked in the hatred filled green eyes of the hunter in front of her, Ruby couldn't help but have her sly grin falter a bit as she took a cautious step back. "Will see about that, Winchester." Her voice shook as she tried to respond boldly, falling short.

The inmates all watched as she made her way down the hall and slammed the door shut.

Sam barely remembered how he got here, he just remembered Ruby flinging him against a dumpster.

As he regained consciousness, he noticed the demon was dragging him down the hall by his hair.

"What the fuck?" He snarled as he helplessly went with Ruby down the dark hallway. The tall hunter gagged slightly as the smell of burning flesh penetrated his nostrils.

"I'll let your brother explain everything." Ruby purred, obviously happy about the situation, the loud click of heels echoing against the walls.

"Dean's here?" Sam questioned, his anxiety level spiking. "Where am I?" There was a trace of fear in the former hunter's tone as he took in the creepy atmosphere.

The demon reached forward, yanking a door open with her free hand before hauling him inside, his eyes trying to adjust to the dim lighting. "Hell." She answered simply as the door shut behind them firmly.

"SAMMY."

At the use of the familiar nickname, the youngest Winchester looked up, immediately making eye contact with none other than his older brother.

Before he could yell out a response, Ruby shoved him inside a musty cell, the door sliding shut with finality.

As Ruby made her way down to the opposite end of the hall, Sam glanced around the cells near him, noting an agitated looking African American man in the cell across from him.

"Sam?" A voice from beside him questioned. Positioning himself as close to the wall separating him and Bobby as possible, he briefly got a glance of a worn baseball cap.

"Bobby?" Sam asked incredulously, not believing the old hunter was down here as well.

"Balls." The man next to him muttered. "Dammit son, not you too."

"Bobby, what's going on?"

….

"It'll be okay Dean." Charlie tried to reassure the distressed hunter who had not stopped his pacing. "Meg has a plan remember?"

Dean ran a tired hand down his face as he stopped, resting his forehead against the cool bars. "I just wish we could get on with it already." He sighed, a trace of desperation in his voice.

Without any warning, all their cell doors opened signaling it was time to go out to the contact non-yard.

Dean tried to catch a glimpse of his brother but there were too many bodies shoving people forward. Be patient. Just wait two more seconds, Dean tried to keep up reassuring thoughts as they all made their way to the yard.

….

As Sam confusedly made his way out to the yard, his gaze searched frantically for his older brother. Bobby had stuck relatively close to his side but right now, the youngest Winchester really needed his older brother.

Dean pushed past Cas and Charlie, his eyes landing on his brother who had a lost puppy dog look to him. Approaching him, Sam looked like he was just bursting with questions.

"Hiya Sammy." Dean started but was cut off when the taller man rushed forward to embrace his family member he hadn't seen in years. "Good to see you too, I guess." Dean added awkwardly, not liking the chick flick moment.

"Dude, what the hell?" Sam asked after pulling away. He glanced at the multitude of diverse people that passed them, Gordon sending them a quick glare for standing in the middle of the path. Dean nodded his head towards his group's usual table and Sam followed him over, sitting across from him.

The eldest Winchester cleared his throat, not sure where to start before it just started to flow out of his mouth. The whole time Dean was explaining, Sam had a look of concentration as he took it all in with his eyebrows furrowed. Once the short-haired hunter had finished, Dean really had a chance to look at his little brother.

Sam was dressed in jeans and a nice dress shirt with a gold wedding band on his finger. His hair had grown to just above his shoulders and he had bags just about as deep as Dean's under his eyes.

"Wait, I still don't understand why I'm here. I mean, you sure I get." Sam hesitated, sending his brother an apologetic but a 'come on, you know it's true" kind of look before continuing. "But I haven't been hunting in years. Why am I being dragged into this?" Sam was spinning his ring around his finger unconsciously, his worry for Jess occupying his thoughts.

Dean rolled his eyes, ignoring his brother's comment about him basically belonging down there. "I don't know Sam. To get back at us? I mean it's not like our family is completely innocent on the demon spectrum." The eldest Winchester glanced at the ring, a pang of guilt going through him. I should've prevented this from happening.

Sam ran a nervous hand through his hair before wiping it down his face. "What the hell are we gonna do?"

"Oh, Dean-o here has a great plan for that." Benny drawled as he plopped down next to his friend. "A stupid plan, but a plan."

Sam glanced at the newcomer warily, before Cas, Jo, Charlie, and Bobby all joined them, filling up the table completely.

As introductions were made, the worry lines on the youngest Winchester's face seem to deepen, not wanting to trust all these people with his and his brother's life.

All gazes turned to the door as Meg walked into the room, her eyes filled with concern as they landed on Dean. "Someone wants to see you."

TBC

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