Fics like There Are Roads Left in Both of Our Shoes

"You’re the only angel I can trust with this request.” He didn’t completely trust her, either. But they’d never tried to kill one another, which was at least something. “I know I’ve been focused on Jack’s soul today. But I was hoping...I’d like you to check if I have a soul.” What happens when Cas wakes up in the Empty a second time, and rescues his own damn self? At first, it seems like the happy ending Dean thought he’d lost his chance to ever know. But as the two set out on a celebratory road trip and begin enjoying their new life together, there’s a darkness clinging to Cas that refuses to completely let go. They may need to make an altogether different kind of journey in order to put the past fully behind them. And meanwhile, where is Jack, anyway?

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