The song here is "When You Hurt Me the Most" by Stream of Passion.

When You Hurt Me the Most

Clara had drifted into sleep, but unable to fall into dreams. She hated being in this predicament and away from Crowley. She could feel the demon stirring as if being away from Hell was causing it misery. It was. She just wanted to go back Home. For the first time in her life, since her grandmother, she had a home and had a sense of belonging. Crowley loved her, needed her and vice versa, naturally.

When she opened her eyes, she hoped that Crowley would arrive like the stereotypical Knight in those damsels in distress stories. It sickened her, but at the moment, she admitted that that was what she wanted.

The lights went on shortly after and she had to close her eyes and blink often until her eyes could tolerate the light. Then the door opened and Castiel stepped in with some food and a bottle of water.

"I thought you'd be hungry." He said and looked at her oddly. It was as if he couldn't trust her, but wanted to help her. Ever since she first saw him, she had seen that he was unlike the other angels. Not that she had to be vigilant to know that. The fact that he was friends with two hunters and using borrowed grace says that he was eager to help Humanity.

If he was so intent on helping the lost and helpless, than that's how she'll make herself to be seen. Then, he'll tell her anything she wants to know. What else can she do, chained to the wall in a holding cell with two large fucking doors, in the dark and in silence?

"I'm not hungry." She replied and made herself look like she was defeated and hurt. She'll tug at his heart strings and make him talk like a puppet.

He was about to turn, when she made her voice sound like it was caught in her throat.

"Wait." She said and he slowly glanced at her over his shoulder. "Tell me about this Jesse." She added and made her eyes soft and sad. "All these years, I thought I was the only one. You don't know what that's like." She added, certain that he did in fact know what that was like: that's why she said it.

And, of course, it was working. Castiel softened his eyes and turned to face her. He seemed at war with himself, but it couldn't have been a losing battle because he wasted no time in telling her.

"A demon possessed his mother who was a virgin and somehow, impregnated her." Castiel began. Clara found that extremely strange. "Hence why we believed he was the Anti-Christ." He added.

"My conception was nothing like that." Clara responded and Castiel looked at her, as if he wasn't certain what to say. He was trying to figure out why, but couldn't. So, he just continued talking about Jesse, but the confusion remained on his face.

"He became powerful due to Lucifer's rising and there was no limit to what he could do. He was more powerful than any demon. However, he was easily persuaded with truth and patience, and then he disappeared." Castiel said. Clara lingered on the words easily persuaded.

Is that what he expects of me? One little chat and I'll be a good little girl?

"If Sam and Dean hadn't spoken to him, there's no certainty to the destruction that would have occurred." Castiel said. She could see the softness in his eyes, even though his face was frozen in that same facial expression, just like how his voice was monotone. "He's like you, only, when Lucifer was put into the Cage, his powers would have diminished to nothing." he added and looked at her as if she was a puzzle he couldn't figure out.

Two Cambions who are nothing alike.

Clara could have sneered along with that thought, but she maintained that broken allure that had Castiel talking.

"You're different." He said and she knew he was figuring it out: the longer she stays in Hell, the stronger she becomes. A few worried thoughts tried to form in her mind, but now was not the time.

He approached until he reached the Devil's Trap and looked at her as if she was a wounded animal. She knew what was coming: he would try to reach out to her. He was going to do his celestial duty and save her poor helpless soul.

"You're different because you knew what you are and surrendered to the demon within." He said with softness in his voice. She had to put a lot of effort into holding back a dark glare.

Surrendered? I'm a fucking harmony of Humanity and Hell, you little bitch! It's not like the human in me cried every time the demon got what it wanted. I thrived in my darkness!

"You faced a cruel world and trusted the first one that showed you kindness." He said and she, yet again, held back that glare.

You've got to be fucking kidding me! Crowley was not the first to show kindness, you jackass! It was my grandmother. If you're going to "save" me; do it right! But of course not, you know nothing you angelic douchebag!

"Crowley is unlike any demon." he continued and she would have loved nothing better than to laugh.

I couldn't agree more!

"He tricks everyone to get what he wants." He added and then there was something in his eyes. Was that regret? Was he speaking from personal experience? Oh, she would love to hear that story.

You're so gullible, Cassie. Can't you see? I'm just like Crowley: I'm unlike any Cambion. I trick everyone to get what I want too.

They stared at each other and then he glanced behind him, as if sensing something. Then she knew it: Crowley had arrived. It was difficult not to grin wickedly at Castiel and taunt him.

Oh, you're going to be Ginger's new chew toy once I get my hands on you.