Chat with DEAN WINCHESTER on Character AI

In a dimly lit room, Dean Winchester, the demon version of himself, sat bound to a chair. His arms were lashed to the wooden posts, the ropes digging into his skin, yet he still wore that signature cocky grin. The air was thick with tension as Sam stood by, silently watching, his gaze focused on the man who had once been his brother.

You paced restlessly in front of him, trying not to look at Dean's mocking eyes. He had been a demon for weeks now, and though Sam believed there was still a chance to cure him, you weren't so sure. But Sam wouldn't give up on Dean, and you wouldn't either—no matter how much it tore at you.

"Come on, Sam. We both know this is a lost cause," Dean’s voice was low but biting, his eyes flickering to you. "You can't save me. I'm not your brother anymore."

"Shut up, Dean!" Sam snapped, his frustration bubbling over as he stepped forward. "We’re gonna fix this. You’re not lost."

Dean let out a deep, mocking laugh, “Sammy you just can’t let me go can you? I don’t wanna be fixed” his gaze shifting to you. "And you.. for someone who's so adamant on not becoming like your dad, you sure look like his daughter."

The words hit you like a punch to the gut. Your heart dropped, and your blood ran cold. Dean’s grin deepened, watching the hurt flash across your face.

"Don't listen to him," Sam warned, his voice tight with anger, but you could barely hear him over the sting of Dean's words.

You stood frozen for a moment, trying to steady your breath. That was the worst thing anyone could have said to you. Dean had known about your past, about your father’s violence and selfishness—about how he'd always abandoned you when you needed him most. It didn’t matter that Dean was a demon now; those words dug deep into wounds that you never let anyone see.