Chapter 1: Ruby's Plan
Ruby seemed to think that she could simple seduce Dean but that would be harder than she could ever imagine. When Dean went to hell, Sam was in a bad place but Ruby made it worse. She took advantage of Sam's grief but every time she left Sam, it was to sneak down & spy on Dean. She did not let either of them know about her plans, until it was too late to stop her.
She never let Dean see her until after he was so broken, he didn't care about anything except the pain stopping. She came to Dean that first night that Alistair had broken him. After he tortured the first person, Alistair gave him a room to rest in for a couple hours. He awoke on an empty dirty bed, in a darkened room. When he opened his eyes, Ruby was standing over him.
She said, “Well, well, what do we have here? Dean Winchester? Oh, how the mighty have fallen? Get up Dean, come on, I don’t have all day not that you can tell if it is day or night down here in the pit. Well, don't you want to know what I'm doing here?”
Dean could not move at first, after a moment he got up.
He said, “Ruby? What are you doing here? Shouldn't you be up there stalking Sammy or something? Well?”
She said, “Your such a sweet talker, I thought you'd be happy to see me? Who knows maybe I can help you out?”
She reached out & touched his shoulder but he pushed her away from him. Then he said, “Whatever your selling I ain't buying, you’re a liar. Just like you were gonna save me from this fate? Yea, I don't think so. Just get out of here, ok?”
She kept trying to touch him but he kept shoving her away. When he finally had enough of her crap, he pushed her against the wall hard, and then he started hitting her hard. Ruby took all the anger that Dean had in him, like it wasn't anything to her. Then he broke down and started crying, he just let everything that he had been holding in, he let it all out. He fell to his knees sobbing, like a baby. She started stroking his hair and this time he didn't push her away.
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Missing Chapters
RandomThis story has multiple pairings in it: there is Dean & Jo, Dean & Ruby at some point and finally Sam & Ruby too. It is mostly a twisted love story of sorts.