The next night, Impala loaded to the nines with anything and everything they could think of, the crew rolled down a dark, wet alley hours from home. Through the mist of the drizzle, they could just see a dingy yellow cab sitting in the alley. There was a tall dark haired man standing near the cab. Parking a few feet back, they poured out of the car, Sam and Dean taking the lead position.

"Ajay. Need to talk to you for a sec," Dean barked through the rain.

"You know my name," the stranger said, not really sounding surprised.

"And what you do. We want to do business," Sam continued seriously.

"But you are mortal - flesh and blood... most of you," the taxi driver said eyeing Cas.

"But if we wanted to cross the border into Hell -" Sam started.

"With a visitor's pass," Dean interjected.

"No one wants to get into Hell," the stranger said, chuckling.

"But could a coyote like you do it?" Sam cut to the point. The trio stood just a few feet behind the brothers, watching the cab driver. He wasn't exactly what they had expected the reaper to look like. Castiel was staring at him hard; not entirely approving of this rogue worker. But then again, he knew he had no ground to stand on from which to cast stones.

"It's possible. But I have special skills. I have overhead. It will be pricey," the figure murmured.

"How pricey?" asked Dean.

"You two are resourceful. One day, you will owe me a favor," he stated simply.

"You say that like you know us," Sam pried, already fearing the answer.

"Of course. You're the Winchesters," he replied.

"Sorry. Have we met?" Dean asked, wanting all the information.

"I am the reaper who took Bobby Singer to Hell," and for a long, stiff breath nothing happened as this horrible news settled in their hearts. Dean and Sam had shared stories of Bobby Singer with the trio. He was more their father than John had been and they loved him fiercely. His death and his haunting had been painful for the boys. This news did nothing to heal that wound.

"Bobby in Hell? We burned his bones. Once we did that, it was over. End of story," Sam was the first to come to.

"Hmm... Not necessarily," the reaper said.

"No, no, no, 'cause, see, Bobby was on the good side of things, and good guys go to the penthouse," Dean said with anger in his voice.

"Usually, mostly. Depends on who you know, what palms get greased. If you're on the King of Hell's no-fly list, no way you cruise the friendly skies," the reaper chimed like he was ordering take out.

"Crowley," the eldest Winchester spat, marking another strike against the King of Hell, "Okay, let's do this. How much for a trip down and back?"

"Dean," Sam said quietly.

"What?" and Sam pulled his head back. His brother followed, annoyed, as Sam came upon the group again.

"What the hell are you thinking?" Sam snapped.

"You heard the guy - Bobby's in Hell. We're gonna spring him," Dean explained.

"We've gone over this, Dean. I have to do the trials solo," Sam started.

"This is Bobby we're talking about, Sam. Now let's face it - you have not exactly been up to full speed lately, okay? We got one shot at this. We can't miss. Besides, with the wonder bunch here, we gotta be a shoe in," Dean said smiling, wrapping his arm around a nervous looking Ron's shoulder.

"I'm not gonna miss. I'll bring him back," Sam said seriously.

Dean spun to face the waiting reaper.

"How does this... Work?"

"Not to fret. You'll be back in exactly 24 hours time," the reaper replied.

"I'm in. Just me," Sam said stiffly, approaching Ajay. Locking eyes with Dean as they all walked up to follow the two, Ron stepped just a little bit closer to Sam.

As the youngest brother and the reaper stood before a painted mural in the alleyway, the paint began to melt as a bright light started to leak out.

"Take my hand," Ajay ordered.

"And it gets creepier," Sam chimed. The light continued to grow and seconds before the two bodies disappeared, Ron lurched forward, seizing Sam's arm. As the light flashed, blinding those in the alley, Sam, Ron and Ajay disappeared across the void, on the journey to Hell.

The bright light around them faded and they were in a forest that seemed white-washed, dimly lit. It reminded Ron of how Harry described memories; in color but the color was muted and faded like an old photograph. Only the light was startling; it was bright but disturbing, like the unsettling lights in a doctor's office. Ron looked towards Sam, who looked shaky and angry.

"Ron what the..." Sam started and Ron just shrugged, smiling. He wasn't entirely sure why he had done it; he felt like he owed a lot to these brothers. He knew that Sam would never have allowed Dean to accompany him, afraid of what returning to hell would do to his brother. But just maybe he would walk this road with a friend.

"Come on, Sam. You don't have to do this alone," Ron said, clasping his shoulder, eyes darting around. Smiling ruefully, Sam turned to the reaper.

"So, this is Hell?" he said surprised, looking around. His own time in hell had been in the pit with Lucifer and he very much doubted that anything would ever come close to that…

"Not at all. This is Purgatory," the reaper replied casually.

"What do you mean this is Purgatory? This isn't what we paid for. We booked the Hell tour," Sam said, the panic clear in his voice. Ron and Sam had talked about what Purgatory had done to Dean; honestly it scared Ron more than hell.

"Whoa, whoa, Winchester, detach. This is Hell-adjacent. Been down this highway many times before. Follow the stream to where three trees meet as one. Where they meet, there are rocks. Between the rocks is the portal," Ajay explained.

"A portal?" Ron queried.

"A back door to Hell. Trust me - it'll work," he reassured.

"Wait. So you're not coming with us?" Sam asked with scrunched eyebrows.

"Don't be ridiculous. Smuggling mortals across the border is risky enough. But gate-crashing with a Winchester into Hell seriously blows. No. I'll be back in 24 hours, precisely. Be here," Ajay explained as he took a few steps back.

Sam nodded stiffly. He shrugged his hands and pulled a long machete out of its sheath against his leg. Handing the wicked looking blade to his friend, he palmed that short fierce blade with the eerie markings along the side.

"It's a good thing you brought that. It is not an easy place," and as the two travelers turned to face the reaper there was a flash of light and they were completely alone.

Ajay reappeared in the empty alley, the other visitors had long since left. Clutching the bag he had made a pit stop for, he climbed into his car and pulled out the greasy, foil wrapped hamburger.

"Hello, Ajay. It's been awhile since we chatted - too long," an accented, oily voice crooned out of the backseat behind the reaper. Crowley's voice was the last sound Ajay heard.

The Impala pulled back up to the door of the bunker. They had about 19 hours left before they had to return for Sam so they returned home to rest and wait. As they walked into the kitchen, Kevin was sitting at the library table, pouring over the scattered pages of notes and scribbles.

"You're back?" he asked, yawning.

"Yeah, just waitin to pick Sammy and Ron up from their play date," Dean said. "How goes the prophet life?"

Kevin stared at him, clearly not amused. Kevin had been a straight A student Ivy League bound when he had been called to the life of a prophet. Since that day he had watched people he loved die, been kidnapped and tortured, and just generally had a pretty miserable life. He didn't know it, but Dean pitied the young man. Dean and Sam had never really known any other life, although Sam had tried a time or two. And the memories that Dean kept under lock and key of his year with Lisa and Ben never really left. But Kevin had lived most of his life as a normal kid. And now he was neck deep in demons and angels and responsibility.

"Keep pluggin kid. We can't do it without you," Dean said, clasping the young man on the shoulder as he trudged to his room. Kevin looked after him. Part of him loved these boys like family. And part of him felt like a very useful screwdriver. He tried to keep that part quiet.

A few hours later Dean was walking through the nearly empty gas-and-sip, resupplying the bunker. He needed something to do besides sitting there waiting for his brother. A flutter in the light caused him to put his hand inside his jacket, around the handle of his gun. He turned around slowly and there was a middle-aged woman in a pants suit with dark red hair pulled into a neat bun staring at Dean, a fake smile on her face.

"Hello, Dean. We haven't been formally introduced. My name is Naomi," she stated, sticking her hand out. The brother took a cautious step back.

"Oh, I know who you are. And I know what you did to Cas after he got out of Purgatory," Dean spat.

"After I rescued him from Purgatory, you mean, at the cost of many angels' lives," she said seriously.

"You screwed with his head and had him spy on us," he barked.

"Well, it is true that I have spoken with Castiel many times, trying to reach out to him, trying to help him. Dean, you must have noticed how Purgatory changed him. I mean, he's been unstable in the past, but I was shocked at how damaged he is now," she said with mock sympathy in her voice.

"Stop, okay? Don't - don't try to spin this. You think I don't know that you told him to try and kill me?" Dean said, holding his hand up to stay her flow of words.

"Hmm. Yeah, I suppose that is how he would hear it. When I learned of the Angel tablet, I did tell Castiel to get it at any cost. That's my job - to protect heaven. I'm a warrior, just as you are. What would you expect? And now Castiel is in the wind with a hydrogen bomb in his pocket, and I - I'm scared, for all of us," again the ingenuity in her voice raked at Dean. He forced every image of Cas and Hermione safe in the warded bunker from his mind, just in case she was trying to tap that vein. Inwardly, he was praising that young girl that anchored his friend in a way he had never seen. Without her, he probably would be MIA on the run. But where she was, he would always return.

"Save it. See, I don't trust Angels, which means I don't trust you."

"Yet here you walk bold as brass, for any willing eyes to see. I know you don't want to believe it, Dean, but we're on the same side - shutting the Gates of Hell, bringing Castiel in from the cold. Take a moment. Think about what I've said. Oh. I know you've been doing business with Ajay. He did mention, didn't he, that his way into Hell is through Purgatory? I knew you'd want to know. You see, we can be of help to each other," she revealed more than Dean ever wanted to hear and before he could reply, she was gone in a flutter of wings.

Slamming the door of the bunker hard, Dean yelled through the depths.

"CAS!"

Having taken to moving through the bunker in ways that didn't leave him open to angelic interference, Cas came running in the kitchen, picking up on the concern in his friend's voice.

"Dean, what is it?" he asked quickly.

"Had a visit at the store from your old pal... Naomi," Dean finished slowly, anticipating his friend's response.

"Naomi?" and the air around Cas snapped and crackled.

"Yeah, she is still hot and heavy after you man. Be careful," Dean still wasn't sure why they hadn't found him in the bunker or why Cas was able to get in and out so easily, knowing the wards they had etched into the stone. But he wasn't going to poke holes until the roof came down. "Listen, she said something about Ajay's way into hell..."

Covered in great splotches of blood and pouring sweat, Ron and Sam slashed their way through Purgatory. When the first monster had appeared, Ron had tried to fight it with magic. But it had no effect on the creature. After Sam had dispatched the vampire, Ron tried a few more spells before realizing that his wand was not going to be an option for them in Purgatory. They then began fighting and running from one attack to another, desperately trying to find the portal to hell. Ron had cut down more monsters than he had ever met, which was saying a lot. Finally, they came upon the point where the three trees met. Locking eyes, they approached the shimmering portal. In a soft glow of light they were sucked into hell.

Standing in a low dark hallway, they could hear screams and mutters echoing through the passages. Grimacing and squeezing their blades a little harder, they ventured forward. Slowly they passed by cells covered in bars and metal. Although it turned their stomachs, they looked into each one on the hunt for the plaid-clad old man in a trucker hat. Ron would never unsee what he saw in this hallway.

Sam came to yet another door. Peering in, he didn't see anything at first so he gave the door an experimental push. As it swung slowly in, he noticed the tally marks scratched into the wall. Staring harder at the shadows he could just make out a stocky figure. Hoping against hope he stepped forward as Ron stepped into the cell behind him slowly.

"Bobby?"

The figure turned slowly. His cheeks were thin and white, his hair was matted and dirty and his eyes looked very close to hollow but there he stood; Bobby Singer.

"Get the hell out of here, you black-eyed son of a bitch," was his reply to Sam's question.

Confused, the youngest Winchester stuttered, "What? Bobby, it's Sam!"

"Yeah, and I'm Elvis. OUT!"

"Bobby -" he began again.

"I said get!" and the old man started to move aggressively toward the two men.

"It's me! Okay, listen. If it's not Sam... Then how do I know all about you and Tori Spelling?" Sam said hurriedly.

"What?" the old man faltered.

"You're a fan. Yeah. Or - or, uh... Okay. What about your free pedicure at the Mall of America? You made Dean swear to never tell another living soul how it changed your life," Sam continued quickly, Ron stifling a chortle.

The eyes of the man seemed to clear a little bit and he stared at Sam as if seeing him for the first time.

"Sam?" he moved forward to pull the boy into a fierce hug, "I'm sorry, Sam, but you're the 200th Sam I've seen today. That's how they screw with me. Just endless Sams and Deans all wearing the same black eyes although usually they are alone..." Bobby noticed the red headed teen behind his adopted son.

"Ugh, Bobby, this is Ron. He is a friend, we can trust him," Sam explained.

"Wait a minute. What the hell are you doing here? Please don't tell me it's what I think it is," concern flared in Bobby's face.

"No, no, no, Bobby, I'm good. We're good. We are ugh, here to get you. You don't belong here, Bobby," Sam said smiling. He handed the ancient demon killing knife to his mentor and pulled another shorter knife from somewhere on his person.

"And we're getting you out."

Dean hadn't taken the time to call for those in the bunker so only Harry rode with him as he tore back to the alley where he had last seen his brother. Harry had taken to sitting on the old motorcycles in the garage of the bunker, when he wanted time to think. That was where he had been when he had seen Dean sprint into the garage. He had barely made it into the Impala before Dean peeled out into the night.

Through gritted teeth the brother explained why he was ripping the quiet apart.

Pulling into the otherwise deserted alley, they saw the small little yellow cab sitting alone in the exact same place it had been before. Parking close to the cab, Dean leapt from the car and walked to the driver's door.

"Ajay? Hey," but he stopped short as he opened the car door and Ajay was staring blankly upwards, black blood covering his front.

Leaning against the hood of the Impala, Harry waited for Dean to finish his phone call. He had been so freaked out when he had seen the dead reaper. Without pausing for as much as a moment, he pulled his phone out, punched a few numbers and waited for whoever he was seeking to pick up on the other end. He strolled around the empty alleyway as he talked in a low voice. Holding the phone out and staring hard at it for a moment after clicking the red button, he finally made his way back over to Harry. The teen looked at Dean, concern and questions written all over his face.

"I... ugh... I called Benny," Dean said, not looking at Harry. Sam and Dean had both talked about Benny to Harry, although usually not in the same room. Dean had always spoken of him in the past tense, like he was a memory that couldn't be touched. It surprised Harry to hear his name come up, considering everything that had happened the last time they had talked, especially to Sam.

"He is meeting us halfway through Arkansas. He is going... to get them out," Dean explained, which meant that the vampire was going to return to Purgatory to guide Dean's family home. Harry felt the cold that he was sure was covering Dean spill over into him. When Dean talked about Benny, Harry understood what they had been through together and he knew that Dean saw him, for whatever he was, as family. Dean could never explain how much it tore at him to ask Benny to do this and, with Harry, he didn't have to.

Without another word they jumped into the car and roared down the empty highway.

Bobby, Ron and Sam burst back into Purgatory breathing hard. They had ended up fighting about half a dozen demons on their way out of hell, trying to be as quiet as they could so as not to put worse creatures on their scent. The stories that Sam and Dean had told Ron about the hellhounds continually played over in his mind.

Sam checked his watch as the three caught their breath.

"Where in the sam hill are we?" Bobby barked looking around at the creepy calm forest.

"All right, don't get all hopped up but... Purgatory," Sam said the last word slowly and maybe a little quieter.

"Balls!" Bobby snapped and Ron couldn't help but smile, recalling all the times the brothers had imitated the expletive of the old man.

The three trudged through the forest that was too quiet, talking softly as Sam guided them back to the spot where the reaper would come for them. As they tried to quietly move through the forest, a handful of sick looking monsters that were alone had made for the group. One by one they had easily been dispatched by one of the men. And still they moved forward, quickening their pace just slightly as the time ticked away.

Suddenly Sam stopped, looking eagerly around.

"What's going on, Sam?" Bobby asked, picking up on the anxiety of his son.

"This is it. This is the place. I'm sure of it," Sam spun around expecting to see Ajay.

"This is where he left us," Ron chimed, his stomach starting to churn.

"When is your cabbie supposed to show?" Bobby asked.

"At exactly... now," Sam looked at his watch.

"So, he's running a little late," Bobby ventured hopefully

"He was very specific, like, to the minute," Ron replied, checking his own watch.

"And if he doesn't show...?" the question hung in the air.

"We got no way out."

"Dean, good to see you brother," and Benny hugged the hunter as he stepped from the car.

"You too man, really."

Harry stepped out of the car and the three men talked in low, heavy voices for a few minutes. Dean's voice betrayed his guilt at what he was asking Benny to do. Benny, for all his bravado, couldn't hide the relief that was coming from his heart. Being topside had been a goal all the time he was in Purgatory. But being a vampire in a human world wasn't all it was cracked up to be; it was hard not to feed. Bagged blood just wasn't the same. There was a small part of him that craved the kill or be killed simplicity of that insane place.

As Dean moved to the trunk to retrieve the machete, Benny stepped toward Harry.

"You look after them now. They are good people but they get in their own way," Benny said, staring straight at Harry. Harry was confused at the speech of the man; the plan was for Benny to return with Sammy and the others as soon as he got them to the portal in Purgatory. Nonetheless he nodded and clasped the hand the vampire offered, feeling the cool skin and tight grip of the man about to die... again.

Dean squared off against Benny as he stood stoically, his eyes just a little red.

"You sure about this?" Dean said again standing with the long blade in his hand.

"Not my first rodeo, man," Benny chuckled. Dean stuck his cold hand out to Benny who took it and pulled the Winchester into a tight embrace. Dean squeezed hard against his friend and sighed a deep breath as they broke apart.

"Thank you," Dean said looking into Benny's eyes. He nodded, swallowing hard.

After a hard moment, Benny broke the silence, "Well, come on. You a wimp?" and Dean smiled weakly as he brought the blade up quickly, Harry turning his head away as the blood splattered on the brick wall behind the headless corpse.

"Dean spent a year in this place?" Bobby panted as the three men paused from fighting another twisted monster.

"Running and fighting, all day, every day," Sam huffed.

"Must have been hell on you not being able to get him out all that time," when Sam avoided Bobby's eyes the old man pried further, "You did try?"

"Look, Bobby, Dean and I had an agreement, okay?" Sam defended.

"I know that agreement. I taught you that agreement. That's a non-agreement. I get the feeling a lot must have happened while I was gone," the old man finished darkly. Suddenly there were four or five vampires hurtling toward them. Each of the three men threw themselves at the beast nearest them, slashing and hacking at their throats. When they whipped around to take the two that had been trailing, they saw the bodies already fallen under a large, pale man who was spitting out chunks of their throats he had bitten off. His fangs glittering with blood, Bobby moved to end this beast as well.

"Bobby, no, no, wait! Wait! Wait! Why are you here?" Sam snapped at the vampire as he stood to face the three men.

"Dean sent me," he said softly.

"Dean? Not my Dean. Not working with a frigging vamp?" Bobby stammered.

Memories of stories registered with Ron as he stepped forward, "Benny?" he ventured and his guess was confirmed by the man's bloody smile.

"He's a buddy of Dean's," Sam said stiffly.

"Well, you two really went off the rails while I was gone, didn't you?" Bobby said frustrated.

The four had set off through Purgatory after another handful of monsters had attacked. Benny explained to Sam what he had to do to get Bobby's soul out. They slowly came up to a steep hill. As Sam and Ron moved toward it, it started to crackle blue and white.

"That's it... it can sense you two. Better get moving," Benny barked over the sound, his eyes roving the forest. Slowly Sam, face tight, pulled his sleeve up and cut a gash into his arm as Bobby did the same. The two locked eyes as they grasped forearms. Slowly Bobby turned into white glittering lights and seeped into the slit in Sam's arm. Yellow speckles swirled around the arm of the youngest Winchester as he gasped, the weight of Bobby's soul bearing down on him.

Having seen it done, Ron turned to the vampire as he rolled his sleeve up. As if on cue, four vampires poured from the forest far away. One of them shouted, recognizing Benny.

"Benny. Still working with the Winchesters," he taunted.

"Hurry!" Ron snapped as the blood trickled down his outstretched arm.

"Time for you two to go," the vampire smiled and turned toward the other beasts.

"Benny!" Ron yelled over the portal noise. The vampire turned back toward them, a small smile on his face.

"Go on. It's me they want. Go on. You just make sure you tell Dean I said goodbye. I was never any good up there anyway," and on the last words he turned to make his move.

"BENNY! Wait," he twisted quickly to face Ron who threw him the long thin machete. He caught it deftly, smiling as the other vampires were almost upon him.

In a crack of light and sound Sam and Ron were sucked out of Purgatory.