Falling for a Hunter (Female Reader x Dean Winchester)

Book 2 Chapter 1: Brave New World

Welcome to Book 2 of "Falling for a Hunter!" This is another lengthy chapter, but hopefully, you love it! 

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In five years, a person can reshape their entire life—graduate from college, find a career, fall in love, get married. The possibilities are endless, but for the Winchester brothers, five years meant something much darker, something far beyond the usual milestones of life. Their years were filled with loss, pain, and battles against forces no ordinary person could fathom. The tragedies they faced piled up faster than victories, leaving scars that would never truly heal.

It started with Bobby's death. Three months after losing you, they lost the man who had been their mentor, their father in all the ways that mattered. Dean hadn't recovered from losing you, not really, but he was getting by—until Bobby was murdered by the Leviathans. Losing Bobby broke something in him, a wound that ran deeper than all the rest. That's when the descent into darkness truly began. Dean found himself trapped in Purgatory, a realm of endless nightmares, fighting his way through bloodthirsty creatures, desperate to find the portal back to the mortal world. Every day in that place was a battle for survival, and every night was haunted by memories of you and Bobby.

But Dean didn't quit. He couldn't. Not after everything. Not with Sam still fighting by his side. He needed to keep going, keep moving, keep hunting because his mission wasn't over. There was still too much at stake. Every day, he longed for the moment he might see you again, but until then, his focus was on the war at hand.

When he finally escaped Purgatory, it felt like things might turn around. Sam was there, waiting for him, and they had a new ally in Kevin, the Prophet of the Lord, who was working with them to close Hell's gates for good. And then they found the Men of Letters bunker—a safe haven, a base of operations, something that felt almost like a home. For a while, it seemed like nothing could stop them. They broke down each seal, one by one, on their way to shutting Hell forever.

But the final test—the one that required Sam's life—was too much for Dean. He had already lost you, had already buried Bobby. He couldn't lose Sam too. So he stopped the trials, knowing it would doom them both to continue fighting. Castiel returned, ready to help, but his trust in Metatron led to disaster. The archangel tricked Castiel, casting every angel out of Heaven. The sky lit up with falling stars as angels plummeted to Earth, powerless.

Desperate, Dean made a dangerous choice. He took on the Mark of Cain, hoping it would give him the strength to defeat Metatron and the other fallen angels. And it did—at a cost. The Mark twisted him, turned him into something darker, something ruthless. In the final battle with Metatron, Dean was killed, but the Mark wouldn't let him die. Instead, it brought him back as something worse—a demon.

Crowley, King of Hell, orchestrated Dean's resurrection, and the man who rose from the dead wasn't the Dean Winchester anyone remembered. This new version of Dean was cruel, cold, and driven only by a thirst for violence. He tore through anything that stood in his way, leaving chaos in his wake. Sam, Castiel, and even Crowley's witch mother, Rowena, worked together to find a cure. They discovered a spell powerful enough to break the curse of the Mark, but the final step required the unthinkable: killing Death himself.

Dean, however, had other plans. He summoned Death, desperate to rid himself of the Mark once and for all. But Death had his own warnings—removing the Mark would unleash something far worse than anything they had ever faced: the Darkness, a primordial force from before God's creation. Death offered Dean a way out, to send him away, far from Earth, to contain the Mark and keep the Darkness sealed. But Dean couldn't do it, not when he learned that the price of his freedom would be Sam's life. Death argued that Sam would never stop trying to save his brother, and so Sam had to die.