Takes place between episodes 4.10 and 4.11, after Dean and Sam save Anna with Ruby's help, who is tortured by Alastair using her own knife.

***

"So… did you enjoy Hell?" Dean found his teeth gritting hard against his jaw. He knew where this conversation was leading, and it was a good thing that Sammy was at a local library researching some dipshit about Maulio Curses. Being the considerate brother that he was, he insisted that Dean patch up a cut on his shoulder while he digs into some ancient news rolls.

"More than you'd know," Dean replied sardonically. He knew that her statement was sarcastic, but little did she know the truth of her words.

Leaning against the door, Ruby's glare softened. "It didn't have to be like this." Her voice was strained, almost hoarse. Dean winced as the needle trembled in his fingers and he jabbed into his taunt skin a bit too deep, which caused a wave of prickling pain to wash over his body.

A sudden wave of anger struck him, and he burst out, "It's too fucking late for that, don't you think? You don't think that we exhausted every single possibility before I was sent to Hell? You don't think that if there was anything—"

"I know what happened in Hell!" Ruby interrupted, her voice traced with hysteria. "Alastair told me when he was torturing me."

Dean's jaw tightened, his tongue now speechless.

She walked slowly towards him, their gazed linked. "You and I both know that there are no words to describe the pit. Only someone who's been down there would understand. Look, you need help with that? At this rate that cut's going to fester with bacteria tomorrow and let me guess, you're going to blame me for it." Dean looked at the bloody mess he was making with the needle, and then shook his head.

"I'm fine—" But Ruby moved swiftly, and before he could protest she was practically on his lap, her fingers weaving the needle through his skin. Up close, the gray blouse she was wearing exposed plenty of cleavage, and there was something alluring about the way her dark hair framed her pale face, lips, and fell to her bosom. If this demon chick knew one thing, it was how to pick a body. When Ruby finished with the final weave, their gazes met for a brief moment, and then she rose towards the door.

"I didn't need your charity, demon. I can take care of myself."

"You know, a simple thank-you would have sufficed." She smiled deviously.

"Well, care to explain something to me? I was only in the pit for six months, and I had lost myself. How could you possibly keep your humanity after six hundred years?"

"I don't—"

"I won't listen to that shit! I want answers." Something had changed inside Dean, Ruby realized. Something significant had shifted inside him, irrevocably, as if he wasn't all here, just a remnant of a soul that had been dragged back. "Sammy may trust you, but I don't, and I never will. I've seen the way you look at him, not like a human but a tool. I see how you've changed him, whispering lies—"

"I saved his life!" the dark-haired demon interrupted, her voice hysterical at the injustice of his statements. "From you. From his grief over you."

"Oh no, no, no—"

"You were the one who changed him, Dean. Not me. Not Azazel. Do you have any idea how much grief and agony he bore from the guilt of living while you rotted away in hell? Do you really think you were doing him a favor?"

"I did what I had to. He would have done the same for me."

"That's what you say, but remember this. You can try to shield him all you want, but we've all changed. He's not the same little brother who's followed you around. Sam has a destiny, and he's going to fulfill it whether you like it or not."

The door slammed behind her. The room was eerily silent, like the calmest before the night tempest. With the wave of one arm, Dean swept everything from atop the dresser, sending metal and glass smashing to the ground, but he could care less. It wasn't because that bitch Ruby was wrong. It was quite the opposite.

Dean fucking hated it when that whore of a demon was right.