CharlyChatfeild
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Summary
“The Angel Castiel, is dead.” She states, in the same tone you would tell someone the weather.
Deans whole body freezes.
“Castiel is dead” She repeats “Your mother is dead. Your father, Bobby, Charlie, Benny, and every other poor soul that you couldn't save.” She spat out harshly, her false smile faltering only slightly.
Or ---
Dean makes a deal with a Cosmic Entity and gets sent back in time.