Though this story is predominantly Dean's, the first two chapters are Sam's story as we say goodbye.
I know in canon Ruby said no demon had the power to release Dean from Hell, but I am ignoring that in favor of telling the story that has been teasing me since I first watched 4.09 — I Know What You Did Last Summer.
This story does not have a beta reader so any mistakes are my own.
The sky was an inky black dotted with stars. It used to be the kind of night Sam loved, one of those nights in which they would park the Impala in the middle of nowhere and sit on the hood, watching the stars. Those nights had come and gone though, there was no one to share the stars with anymore.
The crunch of gravel and his deep breaths were the only sound that broke the night. The animals you would expect in this part of Nebraska were absent. Perhaps they knew what lurked on this deserted road and they knew well enough to stay away. This was a place of darkness, even when the midday sun was beating down. Evil things lurked here.
He came to the right place in the road and he squatted. It was a little used path and the asphalt was covered with a deep layer of gravel, so he was able to make his offering easily enough. He laid the small tin in the hole he had uncovered and stamped the gravel down over it. Heaving out a great sigh, he closed his eyes and waited.
The first sign that he wasn't alone was a low throaty laugh. His eyes opened and he was staring into the face of a young woman with long, flowing black hair. Her russet skin made him think of Native Americans. She was beautiful, with her high cheekbones and almond eyes. Her full lips curved into a smile as she stared at him.
"Well, well, I wondered when it would be my turn."
He crossed his arms over his chest and stared her down. "Can you give me what I want?"
She walked forwards, walking in a circle around him. He could feel her eyes on his back, but he didn't turn to face her. She was trying to unnerve him, but he was beyond such tawdry manipulation. As she came to stand in front of him again, he thought he saw a glimmer of respect in her eyes for her failure to show his disquiet at her stalking him like an animal.
"I could give you what you want," she said in a conversational tone.
For the first time in three months, he felt something akin to hope. All the demons he had spoken to up till then had refused him outright. His jaw tightened as he fought to hide every emotion. Knowledge was power and he didn't want her knowing what he was feeling so she could use it against him. That was the mistake he had made before. His desperation had been obvious in his shaking hands and slurred speech, the result of too much alcohol. He was smarter now; he had learned from his mistakes.
She considered him for a moment. "Maybe."
At least it wasn't an outright no, he thought.
"You'll have to break it down for me. What exactly do you want?"
"I want to take his place," he said.
She tapped her chin with one well-manicured, blood red fingernail. "Keep talking."
"I don't want ten years. I don't want one year. I want to trade places with him."
She smirked. "A straight swap. Intriguing. I can't deny I have been waiting for you to come to me. We had orders, you see. No one was to deal with a Winchester again."
He noted the use of the past tense. "You had orders. What about now?"
She raised her hands to shoulder height. "They still stand for the others."
"Me… What I want isn't covered by orders. I have been waiting for you a long time. Three long months in fact. It took you long enough to find me."
His features twisted into a grim mockery of a smile. "What can I say, I've been busy."
She smiled knowingly. "So have we."
He didn't much care about that. He had a feeling he was close to reaching his heart's desire and any intrigue she was trying to cultivate would only divert him from his true purpose. "Will you give me what I want?"
She was silent for so long that he was sure she wasn't going to answer. He had almost decided to cut his losses here and move onto the next crossroads when she spoke up. "I will do one better. I will give you something you haven't asked for. Time. You can have a day to put your affairs in order before we come for you."
"I don't want time," he said brutally. Time was a bad idea. Time would give his brother a chance to find him. As much as he wanted to see Dean again, he didn't want him to have to see him dragged to Hell. He wanted no one to witness that.
"Too bad," she said. "Because you are going to get it. Call it my reward. I want him to find you. I want him to see you dragged to Hell."
"Why would you care?" he asked.
"Because I owe him."
"What did he do to you?"
Her lips curled back in a snarl better suited to a dog. "He killed my father."
He understood now why she was making the deal against orders. It was revenge for them both. He didn't care though. The ends justified the means. He would get what he wanted, his brother's freedom.
"Do we have a deal?" she asked.
In response, he stepped forward and gripped the back of her head. He pulled her towards him and slammed their lips together. She moaned into his mouth, and his stomach rebelled the contact. His nostrils were filled with the smell of sulfur and he had to fight against his instincts to not pull away.
Eventually, she pulled back from him panting. "I can see the attraction," she said breathlessly.
He wiped his hand across his mouth, disgusted at what had just happened yet jubilant at his success. "Are we done?"
"Yes, Sam Winchester, we're done."