TigerLilyNoh
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In an alternate version of Destiny's Child (15x13), when TFW realize that they need Ruby's help to get the Occultum, but can't bring her back from the Empty, they concoct an unusual plan: to borrow another Ruby from the multiverse-- a better one, a loyal one. But they quickly learn that they've gotten far more than they bargained for. And all the while, Sam must confront his past.
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Sam takes a turn trying to make Rowena beg. She’s fairly confident that she can hold out, but he has a few tricks up his sleeve.
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Sam confronts his feelings for Rowena when he agrees to assist her with an intimate spell... which doesn't go entirely to plan.
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Sam would’ve expected the Apocalypse to have been the most difficult chapter in his life, but that ordeal had been a sprint compared to the marathon of his later years. For decades the hits kept coming one after the other: addiction, illness, and loss— all piled atop a world that had turned harsh. The year is 2078, and the world around him has changed, twisted by ecological disaster, extreme wealth disparity, and the struggle of non-humans trying to integrate into society.
During the last few painful decades of his life, Sam had turned inward as he focused on trying to protect and mentor his family’s next generation of hunters: Jack, Dean’s half-reaper daughter, and his demonic genderqueer child. But during his latest case, he discovers that his family has become caught up in something much bigger than expected. Their investigation leads them into some of the unsavory corners of the city’s supernatural underground, and pieces from Sam’s tragic and sordid past start coming out. He just wanted to protect his family, but it was just like a Winchester to have good intentions go so very wrong.
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Ever since Dean’s transformation into a knight of Hell, Sam has been following the trail of mangled bodies left in his brother’s wake. His goal is to save Dean, but blind in his pursuit, he fails to see the trap set for him. He discovers that not only has his brother found a new, sinister purpose, he’s also found a partner in Abaddon. As their prisoner, Sam struggles to survive and remain a good man, while Dean attempts to twist and mold him into a servant of Hell. Of course, Sam expects to be tortured, but the lengths that his captors will go to in order to break him is only comparable to the absurdity of what they want from him.
Note: This is canon divergent after season nine.