Dean was heartbroken as he stared at the rapidly cooling corpse of his brother. His baby brother, who he had sacrificed so much for just to make sure Sam was safe from their father.
Dean loved John, he tried to be a good son, but a good father he was not after their mother was killed by that damn yellow-eyes.
And now he was dead. Dead by another psychic who had gotten the drop on him.
Bobby tried to convince him not to make a deal, but Dean was beyond caring about his soul. He wanted Sam back and he would do anything to make it so.
A few hours later Dean was heading towards the first crossroads he knew of. He stopped for gas only once, Sam's body covered in the back so that the cops wouldn't ask about the corpse.
It was while he was getting gas that he saw a vintage chopper pull up. The guy looked normal enough, but it was a full moon tonight and Dean knew something was off about the man.
The guy passed by the car and paused for a moment before he went to his motorcycle.
Dean knew that he had seen Sam, or at least the outline when he noticed the guy following him. He pulled over and reached for his gun. If this guy was a cop he wouldn't hesitate to shoot him. He didn't have time to be arrested when he could use it to bring back Sam, and he was already a wanted felon.
Damn shape shifting bastards.
The guy came up to the window and Dean knew his instincts were right when the man opened up with "You're planning to make a deal aren't you?"
"And what if I am?"
"Word of advice, don't trust a demon. They might bring whoever is under that tarp back, but they could just as easily kill him another way just to mess with you."
"Speaking from experience?" asked Dean.
The man didn't say anything, but the look in his eyes spoke volumes.
Dean got a good look at his face and realized that the guy looked way too familiar. It took him a moment to realize who he was really talking to.
"Aren't you Johnny Blaze?" he asked.
Johnny, for that was who Dean had run into, looked surprised he had been recognized.
Dean got out of the car and leaned on his baby.
"So...you made a demon deal. What was it for?"
"My dad had cancer. I wanted him to live so I agreed to ride for Mephistopheles. Bastard killed him with a heart attack the next day and I got screwed over working for hell. I got one over on him though. I might have sold my soul to hell but they can't make me work for them," said Johnny.
"Wait a damn minute. You're the Ghost Rider? Hell's personal bounty hunter?!" said Dean in shock. He had heard of the Rider, hell any hunter who went after demons had. There was a rumor that hell had gotten a new one after the last one went awol and stole a contract, but no one had confirmed it.
Most hunters avoided the Rider because while he did go after the real scumbags there were very few hunters who didn't have a few skeletons in their closet. And the last thing any hunter wanted was to be on the wrong end of his Penitence Stare.
"You've heard of me?"
"Dude, every hunter who chases demons knows about the Rider. We just avoid him as a professional courtesy because we know about his Stare and we don't want to end up in hell," said Dean flatly.
"So who's in the back?"
"My brother. I've spent my entire life trying to keep him alive and some demon kills him for some stupid tournament. No way in hell am I letting that slide. Not if I can bring him back," said Dean vehemently.
Johnny gave Dean a searching gaze. He seemed to find something in Dean that he was looking for, because he wished Dean good luck. The two shook hands and something passed from Johnny into Dean.
While the two never met again for several years, that one hand shake would have far reaching consequences. One that would shake both heaven and hell.
One year and one month later...
Dean screamed in agony as his soul was ripped to shreds. He never regretted selling his soul to bring Sam back, though he would forever hate hell hounds after what that bitch Lilith had done to him.
They had thrown him straight onto Alistair's racks, and for as long as he was in hell all he could feel was the pain. All he could hear were the screams of those who were just as damned as him. Even when they healed him so he could feel the pain anew, he never allowed them to break him.
Because there was something Dean could see that the demons couldn't.
Something that he would be damned all over again if he even breathed a word of what he could see in the pit nearby.
There was an angel, one that hadn't fallen, in hell.
Now Dean had never believed in god. How could he after all the horrible things that happened in the world or seeing his mother die and his father fall apart until there was nothing of the man who had raised him until that horrible night left? Sammy was the one who openly believed in angels and heaven, not Dean.
But in the pit nearby Dean could clearly see an angel on the racks, their wings torn to shreds and their mind almost entirely broken from the torture. It was so pure and beautiful that Dean took some comfort that not everything in the pit was so horrible. If he had one wish, he wished he could help that angel escape.
Maybe if he helped the angel escape, it would bring him to heaven's attention and they would get him out of here. But he couldn't even move without feeling the pain of countless tortures, so that was a vain wish.
For every day that he was in the pit, Dean stared at that angel, letting the light it gave off give him even a small measure of hope in the world.
Finally his mind couldn't take it anymore. He broke and gave into Alistair's suggestions that he start dishing the pain out to others.
Dean could see the sorrow in the angel's eyes, but there was an understanding as well. It knew why he had broken and didn't condemn him for it. Dean took no pleasure in what he did, no matter how much Alistair tried to change it. He was only human, and the human spirit could only take so much before something snapped.
In what seemed like forty years Dean heard a commotion from one of the upper levels. Demons ran past screaming about the angels raiding the Pit, seeking the Winchester in Alistair's racks.
They were so distracted that they didn't realize Dean wasn't torturing his allotted soul. He snuck over to the angel.
"Come with me. If they really are here for me then you shouldn't have to suffer this place too," said Dean.
"I can't. I've been down here for so long and my mind is too far gone to escape," said the angel. It's light was so dim that if Dean hadn't been staring at it for who knows how long he wouldn't have known it was even alive.
"Is there anyway you could leave? Without them knowing?" he asked.
"I would have to take a vessel, and even then my Grace wouldn't be as powerful as it once was. The demons used my corrupted spirit to torment others... Father might not let me return," wept the angel.
"He'd be an asshole if he didn't. You've been down here for who knows how long and you're still the brightest thing here."
The sounds of battle were getting closer. Dean could hear a heavenly voice seeking him, and there was no way he was leaving this angel behind to suffer any longer than he had to.
So he asked "What's a vessel?"
"A human who agrees to house an angel is called a vessel. It has to be consensual or the angel might fall. But all of mine have been forced, not willing," said the angel.
It was why her grace was so weak...Mephistopheles had forced her to take vessels against their will and corrupted her powers. Her commander would be so ashamed of her now.
"What if I gave my consent? Could you hitch a ride out of hell with me?"
She looked at him.
"But the others will know. They might leave you behind," she whispered. A willing vessel would allow her to heal, and possibly re-earn her entry into heaven.
"Not a chance. I hear them calling out for me now. I think they're here to bring me back up, and I swore to myself if I ever had the chance I would help you escape too. You were the only thing that helped me stay sane down here," said Dean honestly.
She reached a broken hand towards him. Dean took it, and he felt something fill inside of him, healing wounds he didn't even know were there. There was a sigh of relief in the back of his mind and he knew that the angel was safely hidden from the others. Only time would tell if the ones coming would notice. He went back to his cell and waited for a few moments before he came face-to-face with a blue eyed angel that took his breath away.
Dean passed out from the sheer relief he was getting out of the pit and saving someone else in the process. It was clear to him that this angel didn't know about the extra passenger at all.
He woke up in a pine wood box in a state of panic. It took him fifteen terrible minutes to dig himself out, and he was glad that whoever had buried him hadn't made it too deep. He took his first real breath of clean air and openly wept with relief.
Inside, he knew that his rescue of the angel hadn't been a dream, because he could hear her crying in joy at the sun in his head.
He took a look at the damage and stared. It was like a bomb had gone off.
He walked towards the first gas station he could find and immediately drained an entire water bottle dry in mere minutes. He looked at the damage to his body in the mirror and quietly asked 'So do you have a name?'
The angel in his head tentatively replied "My name used to be Astarael."
'Bit hard to pronounce. Can I call you Arael instead?'
"After you risked your own salvation to save me, you can call me whatever the hell you want."
Dean chuckled. He could get used to her, if that was what her personality was like.
He was looking in the cash register for something to put in the payphone when this awful loud whine started. Something big flew past the station and Dean immediately went for the salt. The whine grew louder in pitch and volume and the windows literally started to rattle in their panes.
His hands went to his ears from shock and pain before Arael did something.
Suddenly the whine turned into words, though not like any he had ever heard spoken. Arael did her best to translate it into English.
When the whine stopped, Dean looked around for any demons. That was beyond strange, and his weird-shit-o-meter was pretty far out to begin with.
"That was Castiel. It seems he was the one to bring you..."
'Us. Until you're able to go back home consider it an "Us"' replied Dean firmly.
"Castiel was the one to find you first and drag us out of the pit."
'Who is Castiel?'
"An angel that serves directly under Micheal...the annoying bastard," said Arael viciously.
'Micheal as in the arch angel? What have you got against him?'
"It was his idea to have one of the lesser angels replace Gabriel who left because he couldn't stand seeing his brothers fight. And that was after Father left during the Dark Ages. And like the naïve idiot I was, I offered to take my commander's place in hopes that he would prefer one of his garrison to do it rather than one of the sycophants that made up Micheal's ranks. They neglected to warn me that the area I was to be sent in had an arch duke of hell who knew about the idea and planned to capture the angel who came down," said Arael bitterly.
'Right...if this Castiel has a message from Micheal or any of the other angels I'll tell him that they can go fuck themselves.'
Arael gave a bitter laugh, but it was clear she appreciated the thought.
Dean immediately headed for Bobby's. He had to find Sam, and that was the best place to start looking.
Dean was the only one aware of what had brought him out of the pit, but he wanted to make sure it really was an angel. It wasn't that he doubted Arael (and he didn't tell either Sam or Bobby about his new passenger), but it would be nice to double check.
Arael paid half attention to Pamela's attempts to find Castiel, but when she realized that the woman was getting far too close to seeing his true form she acted accordingly and broke the contact before Pamela's eyes burned out.
The psychic blinked, eyes bleeding slightly from the near miss and Looked at Dean.
"Why did you break the contact?" she asked.
"Take a look in the mirror and then ask me that," said Dean flatly.
Pamela had to blink repeatedly to see anything, but what she did shocked her to the core.
"What in god's name could make a psychic's eyes bleed from seeing their true nature?" asked Bobby.
"Icarus," said Dean. Or more like Arael was supplying him this particular tidbit.
"Icarus?" asked Bobby.
"Isn't Icarus the name of the one who flew too close to the sun on wax wings and died in the ocean?" asked Sam. Ever the nerd.
"Pamela got too close to something she couldn't handle, and I could feel it so I broke it before she went completely blind," said Dean.
"You could feel her being too close?" asked Sam.
"Weird right?" said Dean.
He wasn't going to mention Arael. They didn't need to know.
"In any case we need to get her to a hospital," said Bobby.
Pamela would need to wear glasses for the rest of her life, but at least she could still see.
Dean was half asleep when he heard that whine again. Arael was less than pleased that Castiel felt shouting was a good way to get Dean to understand Enochian from an angel's true voice.
Really, if Dean had been in pain the first time then why was he speaking loud enough to qualify as a shout this time? Very few humans could even handle an angel's true voice without going mad, and without her presence Dean wasn't one of them!
Bobby managed to get them out of there before the glass speared Dean.
"What the hell was that?"
"I don't know. But it happened back at the station too," said Dean wincing.
The two quickly got their things together to summon this Castiel character. Boy was that angel in for a real shock.