What would have happened if the Red Eyed Demon had made a different deal with Dean, instead of giving him a year, demanding his life as payment right then and there? Disclaimer: The Winchesters and all affiliated characters are property of Warner Brothers/Kripke Ent. & Co., not me. This is not for profit. Some dialogue was taken word for word from episode 2.22. Thanks to my dad, who provided first hand car knowledge based on his own 1966 Impala.

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Dean Winchester stood in the middle of the crossroads, waiting for that Red Eyed bitch to show up and make the deal to get Sam back. Dean had been as close to catatonic as a walking man can be in the two days since Sam got killed. He blamed himself for everything that had happened, and since life wasn't worth living without his brother, he had decided to make a deal with a devil to get Sammy back, in exchange for his life. At least he would be able to spend the next ten years of his life with his little brother alive before his bill came due; a deal sealed with a kiss.

"Come on already." Dean said quietly to himself, he'd been waiting only a few seconds, but his patience for such things had grown very thin in recent days. "Show your face, you bitch!!!" Dean yelled impatiently to the darkness.

Then, from behind him, in a silky smooth, glassy calm voice came, "Easy, Sugar, you'll wake the neighbors."

Dean turned and saw the pretty woman with black hair dressed in a provocative black gown with glowing red eyes standing provocatively behind him. He couldn't help but let a sneer of disgust curl his lip.

"Dean," she said almost lovingly, a sadistic grin on her face. "It is so, so good to see you." Inhaling, she advanced on him. "No, I mean it. Look at you. Gone and got your family killed, all alone in the world. Heh, it's too sweet."

Dean simply looked on her with disgust, he knew she was just taunting him, but he needed her. And, after all the demons Dean and his family had vanquished, he wouldn't rightfully expect her to be cordial.

She put her mouth close to his ear and continued her mockery. "Excuse me, you're gonna have to give me a moment. Sometimes you have to stop and smell the roses."

"I should send you straight back to Hell." Dean barked, unable to hold his tongue any longer.

She inhaled seductively, "Oooh, you should -- but you won't." She walked off a little behind him. "And I know why."

"Oh, yeah?"

"Yeah," she said, facing him, like the eight-grade teacher's pet about to give an answer none of the other students knew, and proud of it. "Following in Daddy's footsteps, you want to make a deal. Little Sammy back from the dead, and -- let me guess -- you're offering up your own soul?"

"There are a hundred other demons who'd love to get their hands on it." Dean knew he wasn't very popular in her world, and hoped it would give him some leverage.

She bit back a laugh, though her eyes betrayed that she knew he was right.

He continued, "And it's all yours, all you gotta do is bring Sam back. You give me ten years...ten years, and then you come for me." He knew the desperation he felt was making his voice waver, but he didn't care and couldn't help it anyway.

As soon as Dean had said 'ten years', the woman in black looked incredulous, and as soon as the last word was off his lips, she said "You must be joking."

Silence hung in the air for the briefest of moments, and then a disbelieving Dean said "That's the same deal you give everybody else...?"

"You're not 'everybody else'." The demon immediately retorted. Dean looked like a lost puppy as soon as she said it, but she did not let up her assault. She advanced on him again, and whispered in his ear, "Why would I want to give you anything? Keep your gutter soul; it's too tarnished anyway."

Dean didn't look her in the eye as thoughts coursed through his mind. Shit, he thought. He knew it had been a possibility his reputation would require a few years to be knocked off the deal, and though he didn't care to agree to this, life without Sammy was too unbearable to conceive. He nodded in understanding, and said "Nine years?"

"No." She spat back, stepping away.

"Eight?" He said, frustrated.

She laughed, toying with him. "You keep going, I'll keep saying no."

Dean took a deep breath. This didn't look good. "Okay, five years. Five years, and my bill comes due. That's my last offer. Five years, or no deal." He said resolutely.

The demon smiled again in her wicked, sadistic way, and walked in close to his face again. Leaning in as close as a kiss, she brushed the side of his mouth with her tongue as she formed the words "Then no deal."

He did not pull away. He simply glared down at her horrible visage mere centimeters from his face. "Fine." He said gruffly.

"Fine," she said in a mirrored response. She grinned her Cheshire Cat grin and began to walk away. "Make sure you bury Sam before he starts stinkin' up the joint."

Crushed, Dean closed his eyes and fought back tears. Don't let her walk away, stupid! She's your only hope! He heard his own gravelly voice calling before he knew what was happening, "Wait!"

She stopped, and whispered jokingly to herself, "It's a fire sale, and everything must go." She turned.

"What do I have to do?" Dean's voice was pathetic and tired. She could tell, he was willing to pay any price she asked.

She turned and walked back to him. "First of all, quit groveling. Needy guys are such a turn off." She paused, and exhaled, thinking of her options. "Look. Look, I shouldn't be doing this, I could get in a lot of trouble. But what can I say? I've got a blind spot for you, Dean. You're like a...puppy; you're just too fun to play with." She paused for effect. "I'll do it."

"You'll bring him back?" Dean wanted to make sure he had understood her correctly.

"I will." She turned and looked away, knowing she might be pushing the deal too far. "But here's the thing. It's my head if they find out I let a Winchester out of Hell, so for me to bring him back, your bill is due upon receipt."

"What?" Dean was incredulous. "Now you must be joking. That's not a deal--"

"Well, if the answer's 'no'..." She turned and walked back toward the way she had come.

Dean watched the evil incarnate walk away for a few seconds, knowing that even though it was a terrible deal, it was the only one he would ever get, and if he let her get away now, he doubted she would answer his hails later. Not to mention, 'later' would be too late for Sammy.

That's my job, right, look after my pain in the ass little brother? Dean thought, as he remembered trying to comfort his dying baby brother two days earlier. He couldn't bear the thought that he had failed the only person in the world that he loved.

"Fine!" he shouted over his shoulder toward the woman in black.

She turned slowly, Cheshire cat grin back in it's place. "I knew you had it in you--"

"But," Dean cut her off this time, "I have to see him alive."

"No," she said flatly. "Just as the last time I saw you, my word is my bond. And besides, I'm off my quota this month. He'll be alive before your cold rotting meat hits the ground. That's the only offer you'll get. So do we have a deal?"

Dean looked at the ground with his jaw clenched for a moment. He'd been willing to give his life for Sammy's in a heartbeat for as long as he could remember, and this was no different. He was just taking stock of his surroundings; the cool night air, the chirping of the crickets, the smell of the wild lilacs nearby, the sound of a train in the distance, and how his Impala looked. He wished briefly that it had been daylight, so he could see her gleaming the sun one last time before he died...the moon seemed to be mocking him, as it was not out either.

"Tick tock." The woman's voice broke into Dean's thoughts.

He jerked his head towards her, glaring. "I swear to God, if you are lying to me, I will crawl out of Hell itself to kill you."

She sneered, "Now, now, Dean. Gift horses, and all that." She then cleared the distance between them and positioned her face directly in front of his, then asked impatiently, "Do we have a deal?"

Dean looked at her for a few seconds, then leaned in and kissed her forcefully.

As the seal between their lips broke, Dean felt a searing pain in his chest, which moved to his head as he fell to his knees. Unable to even scream because of the severity of his anguish, all Dean could do was watch the dark of night turn in to the pitch black of eternity around him. I love you, Sammy, was the last thing he thought before he sank into oblivion.

The woman in black watched the handsome young man crumple to the ground dead with no compassion whatsoever. As the last gargle of life escaped the body before her, she turned away, disappearing into the night with the sadistic smile still playing on her lips, leaving Dean's body lying unceremoniously in the center of the crossroad in the middle of nowhere.

Dean Winchester was dead.