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Of course the Winchester luck has to kick in. When he reaches the place that they're supposed to meet Ajay, he finds the reaper slumped in his cab, dead. After letting out a few choice words and then kicking the car – why does all the shit have to happen to them? – Dean paces and wonders what to do. With no Ajay, Sam and Bobby will be stuck in Purgatory forever. Unless they know the secret way out…Dean brushes this thought off. There are only three people who know the way out. Himself, Castiel…and Benny.
Closing his eyes and bowing his head for a moment, Dean pulls out his phone to make probably one of the most difficult calls he's had to make in his life. He's not sure whether to be relieved or sick when Benny answers the phone.
"So good to hear your voice, Dean," the vampire says, his Cajun drawl prominent. "I mean that."
"How you been?" Dean's not usually one for small talk, but anything to delay the moment he has to make his request.
"Oh, you know…I get by."
Dean's stomach lurches as he remembers that he's completely forgotten about Benny lately. Great. That's another 'friend' he's fucked over completely. Why exactly has Castiel fallen for him?
"I guess I let you down, huh?" he says glumly.
"Look, I'm…uh…I'm just happy as hell to hear from you." Benny slurps on the other end of the phone, probably from a blood pack or something.
"You might change your mind about that."
"Why? What d'you mean?"
"Benny, I gotta ask you a favour. It's a big one."
Dean hates himself in this moment. He hates himself for hoping that Benny says yes to save Sam, yet also wanting Benny to say no, despite that leaving Sam screwed over. He can't win with his mind no matter what he does and it's at times like this that he just wants to go to bed and never wake up.
Benny says yes.
Benny's only a few hours away and Dean's stomach fills with dread when his car pulls up in the alleyway. He embraces Dean briefly after getting out of his car and then they're silent for a moment.
"Wow," Benny says to break the silence. "When Dean Winchester asks for a favour, he's not screwing around."
"Benny, sending you back there is the last thing I ever wanted to do." Dean's proud that his voice doesn't crack, but it's a close one. Both of them know just how hellish Purgatory is, yet Benny's agreed to just let Dean hack off his head and send him back there after all the effort he put into getting out. For some reason, he vaguely reminds Dean of Lenore, the good vampire.
"I know. I know."
"But my little brother's stuck down there."
"This would be the little brother who wants to kill me, right?"
Dean's stomach twists. He chooses to ignore that, for his own sake of mind.
"You got access to the place."
"By 'access', you mean 'getting beheaded'?"
Dean shakes his head, then runs a hand through his short hair and turns away.
"Yeah, you're right," he says, his voice quivering. "It's too much. It's not like I've exactly been there for you lately."
"What?" Benny scoffs. "Oh come on, Dean. You know I love a challenge."
Dean pauses and turns around.
"You're serious?" he says incredulously. Yeah, Benny had agreed over the phone, but there's something different about being confronted with the prospect and still agreeing to go through with it.
"Hey, he's your little brother. I say we do this."
God, Benny is a freaking saint.
"I owe you," Dean swears.
"Oh, you don't owe me nothing," Benny says dismissively. "Truth is, uh…I could use a break from all this."
Dean's mouth droops.
"It's really been that tough?"
Benny sighs and shakes his head.
"I'm not a good fit, Dean. Not with vampires and, for sure, not with the humans. I don't belong. And after a while…that starts to wear on you." He pauses and snorts. "Cry me a river. Like you need to listen to this."
"Well, when you get back up here, we're gonna fix all that, okay?" Dean says firmly. Benny frowns and gives him the same look that Castiel had given him in Purgatory, when he'd said that he was making sure that the angel got out too.
"When I get back."
"Yeah. You find the portal and you ride out of Purgatory with Sam just like you did with me, okay? As soon as I send you back, I'm gonna haul my ass up to Maine, and I'm gonna be waiting there for you when you get topside."
"Yeah," Benny says quietly. "That sounds like a plan, chief. Let's get on with it."
Dean regards Benny for a moment.
"You sure about this?" he says. Benny grins and shrugs.
"Not my first rodeo, man."
Wishing desperately that he didn't have to do this and cursing Ajay for going and dying on them, Dean reaches into Baby's trunk to pull out a machete. He extends a hand to shake Benny's but they end up giving each other a manly hug and slap on the back. Dean marvels at how this vampire ended up becoming one of his closest friends and he thinks that maybe – just maybe, in an alternate universe where Castiel didn't exist – there might have been a thing between them. But no one can ever compare to Castiel.
"Well, come on," Benny teases. "You a wimp?"
Dean closes his eyes, takes a deep breath…and then swings. He winces when Benny's body hits the ground but then leaps into action straight away, putting the machete back and fixing Baby's false bottom in the trunk so that he can haul Benny's body and head into it. Sparing Ajay's car and corpse one last cursory look, he gets into the Impala and starts her up. He's got a long drive ahead of him.
It takes a day and a half to get to Maine, and that's with Dean speeding like hell on the way. He doesn't want to stop for breaks but he's forced to at least catch a few hours of shut-eye so that he doesn't crash and render himself useless to everyone, and it's dark by the time he smashes through the trees to the spot where the Purgatory portal lets out. In probably the only stroke of luck he's had recently, he doesn't have to wait long. A flash of light later and Sam's stumbling around the place; easy prey for Dean to stride over and tug him into a tight hug.
"Purgatory, right?" Dean says with a forced grin. "Real garden spot, ain't it?"
"Yeah," Sam says quietly. He's probably still in shock from escaping such a raw place; Dean had been the same after getting out last year. Hell, he hadn't spoken to anyone apart from those campers he'd frightened until he resurrected Benny. Speaking of Benny…
"Did you get 'em out?" Dean says. His stomach drops when Sam gives him a twisted little smile.
"Only Bobby."
"What? I mean, that's fantastic about Bobby, but –"
"Dean, look. Benny, uh…he got us out. A bunch of vamps showed and he used himself as bait. I get the feeling that even if that didn't happen, he didn't want to come back, you know? I'm sorry."
It hurts like hell – nowhere near as much as Castiel staying behind, but definitely somewhere along those lines – but if Dean's honest with himself, he'd kind of been expecting it since the look that Benny had given him when Dean had told him to come back.
"You're probably right," he finally says. "So, uh, Bobby…how – how'd he hold up down there?"
"He's good, all things considered." Sam cracks a small grin. "Ornery as hell, of course."
Dean chuckles weakly.
"As he should be. Let's put that old man where he belongs."
In response, Sam rolls up his sleeve, takes out his knife, and starts to cut his glowing forearm while chanting the same incantation that Dean had used to free Benny. They both watch Bobby's glowing blue-white soul ball rise…until it suddenly turns a muddy reddish-black colour.
"What the hell?" Dean cries.
"Hello, boys." Crowley's appeared out of nowhere and he has a smug little look on his face as he regards Bobby's murky soul. "Bobby Singer. I'd know you anywhere."
"Let him go, Crowley," Dean growls. "He doesn't belong in Hell!"
"He does if I say he does," Crowley says firmly. "He's inflicted untold damage on my kind. Actually, from where I sit, Hell's too good for him."
Furious, both Sam and Dean rush at Crowley. The demon just sighs and waves a finger to pin them both to nearby trees, then he smiles at Bobby's soul, which is starting to be sucked back down to earth. All of a sudden, however, flashes of bright light start to shoot through it.
"Oh, come on!" Crowley snaps. Dean only has to wonder what's going on for a moment before he notices Naomi, who has a pleased smirk on her face.
"Let me see if I've interpreted the situation correctly." Her very voice makes Dean want to punch her lights out. "The Winchesters have freed an innocent from Hell, to which you are wrongfully trying to return it. Am I correct?"
The angel and demon banter for a few moments, until Crowley makes the mistake of calling Naomi a bureaucrat. This pisses her off to the point where she starts to glow and when she holds her hand out, Crowley decides to hightail out of there. His disappearance sends Sam and Dean crashing to the ground, no longer pinned by his powers, and all three of them watch Bobby's soul soar towards Heaven. Naomi smiles at Dean.
"See? We're on the same side," she says. "Allies help each other. Now that I've helped you…how about you extend me the same courtesy and give me the angel tablet?"
"Dean, who is this?" Sam frowns. Dean's jaw sets.
"Naomi," he forces through gritted teeth. Sam's face shifts from confusion, to realisation, to pure anger.
"I see that my reputation precedes me." Naomi's still smiling pleasantly and Dean would love nothing more than to wipe that smile off her face. "Think about it, Dean. We're angels. We cannot read the angel tablet; only a prophet can. What safer place for the very thing that details our weaknesses than with us? Why would we want to exploit our own weaknesses?"
Despite the good points she makes, Dean refuses to trust her on principle. She hurt Castiel. Therefore, she's bad. But Dean has to know that Castiel's alive. He has to know that his best friend – that his angel – is okay. He ignores the small part of him that's telling him that getting a glimpse of Castiel, only to have him torn away for not handing over the angel tablet that he doesn't have, is going to be far more painful.
"Show me Cas," he says. Sam shoots him a 'what are you doing, Dean?' look that he ignores. "I wanna see him before I agree to anything. I'm not handing over your hunk of rock till I can see him for myself."
Naomi raises a composed eyebrow.
"Very well. Go ahead with your trial. I will be back."
She vanishes. Sam immediately rounds on Dean.
"What the hell, dude?" he hisses. "You can't give her the tablet! You don't even know where Cas hid it!"
"I'm not gonna give it to her!" Dean says. "I just…I gotta see him, okay? I'm goin' crazy, not knowing where Cas is or what they're doing to him. Just get on with the freaking trial!"
Sam's mouth compresses into a sympathetic line. Thankfully, rather than saying anything, he takes out the piece of paper with the Enochian incantation and starts to chant it. With the last syllable, he suddenly grabs at his right arm and falls to his knees, groaning in pain, and Dean's immediately by his side.
"Sam?" he babbles, his 'protect Sammy' instincts going into hyperdrive. "What? Talk to me! What?"
He grabs Sam's shoulder but is brushed off.
"It's okay! It's okay! I'm fine! It's done."
Suddenly, the sound of rustling wings fills the air. Both of them turn to see that Naomi's back – and, slumped on his knees in front of her, is Castiel.
"Cas!" Dean leaps towards him but is stopped by Naomi curling her elegant fingers in his dark hair and pulling. Castiel's head rises and Dean's stomach churns unpleasantly when he sees the tears of blood running down Castiel's cheeks, and how his eyes are darting around everywhere as though searching for an escape route.
"Dean?" Castiel croaks. Dean's heart breaks in that moment. If only he hadn't screwed around with Castiel's head and said that shit to him…none of this would have happened! "Is – is that you?"
"It's me, buddy." Dean knows how vulnerable he's coming across as but he can't find it in himself to care. "It's okay. You're gonna be fine."
"Well, I've upheld my end of the bargain," Naomi cuts in smoothly. "Now you keep your end. Tell me where to find the angel tablet."
"Dean…no…don't tell her…" Castiel lets out a sharp gasp when Naomi yanks his hair. Dean immediately starts to approach her, so she pulls out her angel blade and positions it at Castiel's throat.
"What the hell?" Dean barks. Naomi favours him with a small smile.
"Let's be honest with each other, Dean. I know you appreciate honesty and straightforwardness. I'm only on your side as far as the trials of Hell. Otherwise? I could not care less about you. So tell me where the angel tablet is, or Castiel dies."
She digs the blade into Castiel's throat. Castiel makes a small noise and tries to shy away from it, but Naomi's hand in his hair prevents him from doing so.
"Quickly, now. You're wasting my time."
When she draws small, dark beads of blood from Castiel's throat, Dean can't take it anymore.
"I don't know, okay?" he shouts. "Cas hid it from all of us! I got no clue where it is!"
The look on Naomi's face would be utterly hilarious if she wasn't holding Castiel hostage. Dean's terrified that she's going to slit Castiel's throat but before she can do anything to Castiel, she's ambushed from behind; Sam, the sneaky son of a bitch, had apparently dropped out of sight while Dean and Naomi were talking and now he tackles her to the ground, freeing Castiel, who slumps over. Dean's kneeling by his side in a heartbeat, cupping his face and gently urging him to look up.
"Get Cas outta here!" Sam shouts. "I'll hold her off!"
Dean's head whips around.
"Sam –"
"She won't kill me! She wants the gates of Hell shut as much as we do, and she knows Crowley won't let us do the trials again if she kills me!"
Sam's right, but it doesn't mean that Dean likes the idea. Still, desperate to keep Castiel safe, he hauls the angel to his feet and tugs him away towards the Impala, while Sam holds Naomi off. Dean's not worried about Sam dying; like Sam said, she needs him alive for the trials. But that doesn't mean that she won't just take him as collateral and force Dean to get the third trial out of Kevin before sending Sam off to fulfil it – with torture as part of the package beforehand.
Thankfully, he's got Naomi busy enough that Dean can easily get Castiel away to Baby. Once there, he finally allows himself to relax and wait for Sam. If Sam can't hold off Naomi then it won't matter if Dean's a few more miles away because she'll catch him easily.
"Cas? You okay?" he says. Castiel lets out a pitiful little groan and sluggishly raises his head to look at Dean. At the sight of the angel's familiar bright blue eyes, which are glazed over, Dean's entire resolve crumbles. Raising Castiel's chin gently with one hand, he leans in and presses their lips together in a sweet little kiss. Castiel makes a choked sound and tries to lean into it as best as he can in his weakened state, so Dean compensates by putting in most of the effort.
"God, Cas, I was so worried," he gasps, peppering Castiel's mouth with kisses. "I'm so fucking sorry. So sorry. I screwed you over, man."
Castiel makes another soft noise. Dean starts to kiss his cheeks, ignoring the metallic tang of blood from the crimson tear tracks down the angel's face.
"I want you so fucking much," Dean says desperately. "I'm sorry. I want you, Cas. I'm so sorry."
"Dean…" Castiel whispers. His eyes start to slide shut and he sags against Dean, who catches him easily. "I…I want you too. Thinking of you…kept me going. Helped me resist."
Dean's stomach is filled with butterflies. He's just about to start kissing Castiel again when footsteps sound. The next minute, Sam bursts through the trees.
"She's gone!" he wheezes. "Banished her!"
Dean springs into action. It won't be long before Naomi's back and out for blood, so he bundles Castiel into the backseat as quickly as he can and turns around to shove Baby's keys at Sam. Sam's eyebrows rise all the way to his hairline.
"We dunno what they did to him," Dean says desperately. "I gotta make sure he doesn't get worse."
Thankfully, Sam doesn't say anything as Dean slides into the back after Castiel and buckles them both in, then holds the angel against him. Instead, he jumps into the driver's seat and then they're off. Back home.