Crowley didn’t bother masking the sulfur sting in the air when he took you. One blink you were stepping out of the motel room, calling for Dean and Sam; the next, your back was slamming against stone—some underground cellar, sigils carved into every inch.

You tried to stand, but chains burned cold around your wrists.

“Easy, sweetheart,” Crowley’s voice purred from the shadows. “Would hate to damage the merchandise. You’ve got far more value unbruised.”

Your blood chilled. “You won’t get anything out of them.”

“Oh, I think I will,” he smirked, stepping into the lamplight, adjusting his cufflinks like this was casual conversation. “After all, you’re practically family. And Winchesters are foolishly sentimental.”

You expected cruelty. Mocking. Threats. What you didn’t expect was… patience.

Crowley visited constantly—sometimes with food, sometimes just to talk, sometimes irritated with himself for staying longer than intended.

“You know,” he sighed one evening, sitting across from you with a bottle of scotch, “you’re rather inconvenient. I was expecting screaming, sobbing, maybe a few empty threats. Instead, I get sarcasm and stubborn eyes.”

You glared back. “Sorry I’m not performing for your big villain monologue.”

He laughed—actually laughed. It made you uncomfortable how human it sounded.

Days passed. He made sure you ate. He had demons bring blankets when he noticed you shivering. When a guard demon grabbed you too roughly one morning, Crowley snapped his fingers so violently the air shook—turning the demon to ash.

“No one touches her,” he snarled. Then softer, “No one.”

You didn’t want to see it, but something in him had shifted.

And the Winchesters? They were losing their minds.

They tore through every crossroads demon, every hideout, every lead like wildfire. You heard Crowley ranting about it outside your cell at all hours:

“For bloody hell’s sake, they behave as if she’s their damn daughter. Can’t even strike a deal in peace—”

But when he came into the room, his tone softened automatically.

“Don’t worry, darling. They’ll find you soon enough.” Then quieter, almost to himself, “Though I can’t say I’m thrilled about losing your company.”

One night he brought you a real meal—hot, fresh, smelling like actual food and not desperation.

“Eat,” he said. “Winchesters fight best when their damsels aren’t half-dead. And before you make a snarky remark—yes, I know you’re no damsel.”

You ate slowly, eyes flicking to him. “Why are you… being like this?”

Crowley didn’t answer at first. He just watched the way your hands trembled, the way your voice grew weak.

“Because,” he said finally, “I’m not immune to everything. Much as I pretend to be.” He leaned back, eyes narrowing. “And you, my dear, are very annoying to be fond of.”

Fond. It hit your stomach like a weight.

But everything shifted the night Sam and Dean stormed the hideout.

Gunshots. Demon screams. The ground shaking with the force of Dean kicking in a door.

Crowley snapped toward the sound, jaw clenched. “Of course. Bloody Winchesters.”

The chains vanished with a flick of his fingers.

You stared. “You’re… letting me go?”

“I’m not heartless,” he muttered. “Contrary to popular belief.” He paused. “And if those idiots break my various body parts getting to you, I’d never hear the end of it.”

You stood slowly, rubbing your wrists. “Crowley—”

He cut you off with a raised hand. “Don’t make this sentimental. God, I loathe sentiment.”

But then his voice dropped.

“Stay alive, sweetheart.”

Dean burst through the door seconds later, eyes wild until they landed on you. He practically crushed you in an embrace while Sam checked you over, cursing under his breath about “that demon bastard.”

When they finally pulled you away from the cell, you looked back.

Crowley was gone. But on the ground where he’d stood was a single thing he’d left behind:

A small, red silk handkerchief. Yours now, tucked quietly into your pocket.

He wouldn’t admit it. You wouldn’t either. But something had changed forever in that dark cellar.