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Ruby is a demon. She's also Jane Doe, and a woman, and a Winchester. (It's just too bad they don't see it that way). She's a girl, lying in hospital, with her spirit flown; she's a creature, with her hands around a man's face, around his neck - and she could break him so easily, and he could break her back, harder. (Sam, Sam, dream of me, Sammy.) She feels pain, and it burns - along her mid-section, and over her skin, and inside her chest (dream of me, Sam, when no one else will) - and she screams, and screams, and screams.
No matter what they say, she's a Winchester - she walks with them, and she fights with them, and she protects them (it's true, if she does say so herself). The blood drips down her chest, and across her hands - and the one man she needs doesn't trust her, won't care for her (dream of me, Sam), after all they've been through (Sam, Sam, screaming his name, his fingers carding through her hair - and it's hot and it hurts, and it's fire, Sam is the forest, and she is the flame - and that's all they need for it to glow).
Ruby's worn a lot of faces, over the years - the many, many years, before the world was different, and before she had to see Lilith burn (and Sam could do that, and he could get it right, and he won't). This one doesn't fit her - but it's as close as she can come, in a barn with an angel, the same girl who trusted her (she's different) - and Anna's a pillar of white light, and she's yelling - and Ruby closes her eyes, as the cosmos shifts again, and another bright spirit is gone, consumed by the angels.
There's a tree outside, and as Ruby walks away from it, it weeps blood. She doesn't look back, because she can't. I'll see you again, Sam, she says, and means it. As she leaves, past a shaken Dean ('cause that angel's got him all shook up, oh yeah, all shook up - that blue-eyed angel, who's just the same as all the others), and they share a nod - because they have something in common, and that something is Sam.
And Dean's going to Sam's side, like he always does - but Ruby notices the glance he sends out, the way his eyes flit. That blue-eyed angel's got him all shook up, and there's gonna be Hell to pay - Hell itself, in the stinking darkness, where she'll never return (where she never returned from). She presses a hand against the tree (just like Anna had) and waits - and there's no response.
Anna said she could feel her Grace - could feel that it wasn't there. Ruby waits, and can feel nothing, apart from the cold, and the blaze in her chest. Maybe that's the way it's supposed to be; because now, she has no choice but to go back on the road, and (in her heart of hearts, although they're apart) become a Winchester once again. The highway calls for her, and she answers it. Spreading her wings wide, Ruby (Winchester, someday) closes her eyes, and soars.