He stepped into the doorway of the room, her captor, Cas as he had been called, walking in to join him. The two whispered about something for a moment before Cas left and it was just Y/N and Squirrel left in the room.

“I’m sorry that we had to put you through that, but we had to get you away from Crowley.” The man spoke, walking towards Y/N.

“I don’t know you,” She screamed, kicking her legs out as he got closer. “Please let me go.”

Dean’s heart shattered at those words. She didn’t know him, how was that possible? Dean’s mind immediately went to the possibility that Crowley had done something to her. That he had kidnapped her in her vulnerable state and wiped her memory so she would never leave him. It made his blood boil to think about, but he could not let Y/N see him get angry knowing it would scare her if he did.

So instead he took another step towards her and crouched down to her level to speak. “You do know me Y/N.”

The woman shook her head, tears falling down her cheeks. “No, I don’t, I’ve never met you before today.”

“Baby girl, it’s Dean.” He tried placing a hand on her knee, but she jerked it away before he was able to touch her. “I’m your fiancé.”

Y/N shook her head, more tears trailing down her face. “No, I’m with Crowley.”

Dean stood, running a hand over his face the anger inside of him growing. Y/N could see it build behind his green eyes and it made her fear grow. She had no recollection of meeting this man before today, for all she knew he had her kidnapped to get back at Crowley or to live out whatever sick and twisted fantasy he had cooked up inside his brain. But she was too afraid to ask, worried that he would take that anger out on her.

“It’s okay baby, I’ll figure out what he did to you.” He said as he brushed some of her hair behind her ear before turning and leaving.

Y/N spent the next few hours alone in the chair, crying and praying that Crowley or anyone could hear her pleas and come help her. But as the hours dragged on it was clear that there was no one coming for her; how would they? Crowley probably had no idea she had been taken and even if he did how was he going to know where they took her. So, she stopped, her resolve waning with each passing minute.

In the fourth hour of being tied to the chair the dungeon door swung open again, revealing both Dean and Cas. Upon seeing the two men tears began filling her eyes and she struggled against the ties holding her wrists.

“Please let me go.” She begged, tears beginning to roll down her face. “I won’t say anything.”

Dean sighed, pinching the bridge of his nose. He hated hearing her beg and plead, he wished she would believe him when he said that they weren’t going to hurt her. He wished she would believe that he just wanted to help her get away from whatever Crowley had done to them.

“Y/N, we’re not going to hurt you.” Dean tried one more time, “Cas is going to look over you and try to figure out what’s wrong with you.”

“There’s nothing wrong with me!” she argued, kicking her legs out again, trying to keep the two men away from her.

Dean gave Cas a look and in a split second he was standing behind Y/N. And before she could argue or plead, he was pressing two fingers to her forehead. He held them there for a moment, Dean watching as Y/N’s eyes snapped shut against the feeling. He knew it did not feel good, having an angel rummaging around in your head but it was necessary if Dean wanted to help Y/N.  

When Cas took his fingers away Y/N slumped down in the chair, the events clearly exhausting her.

“He took some of her memories,” Cas said to the hunter.

“You’re right, I took her memories of you Dean.” A voice sounded from the doorway, making Dean whip around drawing his gun from his waistband.

Dean was seething with anger wishing that in that moment that a bullet would have been able to kill him. “Why the hell would you do that? How the fuck did you even get in here?”

“She asked me to, I didn’t do anything she didn’t want me to.” Crowley looked from Dean to Y/N, his own heart breaking at the sight of her tied to the chair, “I can’t say the same thing about you though.”

Dean’s nostrils flared, his fingers tightening on his gun. He didn’t believe a single word he was saying. There was no way that Y/N would have asked him to do that. He didn’t want to believe it.

“No, she would never.” Dean argued.

Crowley shook his head and reached inside his suit jacket to retrieve the contract Y/N had signed all those months ago. He knew that this was the only way to get Dean to realize that Y/N had asked for this favor from him. While falling for Crowley hadn’t been part of either of their plans.

“Read this.” Crowley said, handing the folded piece of paper to him.

Dean snatched the paper from Crowley, keeping his gun trained on the demon as he read the words printed on the paper. Dean’s eyes ran over the words, pain filling them as he read over the signature at the bottom.

“It’s fake. It’s got to be fake.” He screamed throwing the paper to the ground.

“Dean, you and I both know that its not. You broke that poor girl, and she came to me to help her. Neither of us thought it would end up like this. So, please just let her go, its over.”

Dean dropped his arms, putting his gun back into the waistband of his pants. His own heart shattering but he broke the devil’s trap, allowing Crowley to go and untie Y/N.

Y/N woke up with a headache, expecting to be still tied to the chair in whatever dungeon Dean had taken her to. But when she fully opened her eyes she was wrapped in crimson sheets, a silk night shirt covering her figure, and a familiar scent surrounding her.

She was home.

“Darling?” Y/N called out, her voice shaking slightly as she went to sit up.

It took a moment, but Crowley eventually appeared in the doorway, a tray piled high with all of her favorite foods held in his hands.

“I am so sorry love,” Crowley began to apologize as he made his way towards their bed. He set the tray on her lap before joining her in bed. “I never meant…”

“Hush darling,” she interrupted, “I don’t blame you.”