Ruby had met up with the boys during their most recent hunt. Once Sam realized that demons were behind the deaths in this town he called Ruby in for help, much to Dean's chagrin.

Sam was tried of listening to the bickering so he had jumped at the chance to go on a supply run, eager to have some peace and quite for at least a little while.

Dean was sitting back on one of the beds in the motel room, flipping through the few cable channels the motel offered. Every so often his eyes would drift over at the dark haired demon that was sitting at the table pouring over Sam's notes on the case.

Finally Dean couldn't stop himself, "What kinda game are you playing here Ruby?"

"What are you talking about Dean?" Ruby replied in a bored tone, while she continued to read.

"You know what I'm talking about, this thing with Sam. Helping us. I know you aren't doing all this out of the kindness of that demon heart of yours."

"What do you know about my heart?" She said too quietly for Dean to hear. "All you need to know is that I won't do anything to hurt Sam."

"And you don't think all of this isn't going to hurt Sam? Where do you think Sam is going to end up if he stays on the path you have him on? Huh? I doubt he will end up on the guest list at the pearly gates."

"Is that what you are worried about? That Sam might end up in hell?" Ruby shakes her head and mutters under her breath, "Fucking short bus!"

"Hell yes that's what I am worried about." Dean replied, turning off the television and throwing the remote down on the bed. "I didn't sacrifice myself and go through all I went through downstairs for Sam to end up there."

Ruby finally looks up from the notes she is reading and looks at Dean, his features are a combination of worried, scared and angry. She can't believe he never really thought about all of it. She got up from the table and walked over between the two beds and sat on the empty bed facing Dean. "It doesn't matter Dean.", she told him in a soft voice.

"Doesn't matter!! Yes it does fucking matter I don't want my brother to end up in hell!"

"I didn't mean it like that. I meant it doesn't matter if he uses his powers or not. If he does things my way or your way."

A look of confusion crossed over Dean's face.

"Sam's name was removed off the guess list the moment Azazel dropped his blood in Sam's mouth." Ruby told him in a calm voice.

"You don't know that!" Dean yelled.

"Yes Dean, I do."

"No with all the evil things we have fought, all the people we saved. As long as Sam's doesn't use his powers anymore there is no way they will let him go to hell."

Ruby sighed and shook her head sadly, "They already did."

"What are you talking about?"

"Sam has already been to hell Dean."

"When?"

"Please Dean, I am trying to be kind at the moment and you asking stupid questions like that is making it difficult. When he died Dean."

"Wha.. wait he was dead for about a day…"

Ruby interrupts, "Which you know is over four months in hell."

"But he's never said anything to me about it." Dean says quietly.

"He doesn't remember."

"Then how do you know?"

"His was the purest soul that was ever put before me down there." Ruby said looking down at her hands. "The others they relished tearing him apart day after day. But me I hated it. It felt like my first months in hell all over again. And Lilith I think she knew how much it bothered me, she made sure I was there for every second of it. And then you made your deal. She was completely beside herself, she was going to get all three Winchesters to play with."

"Three?"

"Your dad was still down there at the time. But I ruined that one for her. When the Devil's Gate opened I grabbed your father and flew like a bat out of hell, literally!"

Dean was speechless. Different thoughts were running through his mind, Azazel's comment about Sam after he killed Jake, seeing his Dad there. "How do I know you aren't making all of this up?"

"Why don't you ask your angel buddies about it. But don't tell Sam." Ruby stood up and walked back over to the table to continue with her research.

Dean lay back on the bed and stared at the ceiling, he wasn't sure what to think.