The first few "visits" to Heaven, he talks easily.

Still weak from Purgatory, Castiel is exhausted, he's confused, and he doesn't realize until it's too late what he has said. The treacherous words slip from his lips before he knows it, and by the time it sinks in, Naomi sends him back to the loving arms of his beloved Winchesters. It's a perfect system.

Of course, it's too good to last.

Every passing day, Castiel grows stronger. Each time he is snatched away from his human pets he seems to recall more about the previous visits. He guards himself more carefully. It takes longer and longer to get him to talk, until one day, he won't say a word.

"Tell me about the Winchesters, Castiel."

"I won't."

The words seem to echo around the brightly lit office. Naomi looks up, disappointed but not surprised. Castiel has built up a reputation for being strong-willed and annoyingly loyal to his pets. She has known all along that it was only a matter of time before he was able to resist her will.

"I'm sorry?"

"I said," Castiel growls, contempt in his voice, "I won't. I will not betray them."

Naomi sighs and slowly gets up from her chair, smoothing out her suit before walking around the desk to stand directly in front of Castiel. She folds her arms and stares at him for a while.

"Now, Castiel," she says, still smiling, in a voice that a mother might use to address a small, disobedient child. "Don't be foolish. We had an agreement. You must honour your will honour your side. The only question is, how easy or hard it's going to be on you."

This earns her a small smirk from the recalcitrant angel.

"You make an excellent bad cop, Naomi."

"Excuse me?"

"Bad cop," he repeats, "I would ask for some pointers, but I'm afraid they would be wasted on-"

"Silence, Castiel." Naomi says, raising her voice for the first time as anger finally breaks through her normally cold, calm demeanour. "Enough stalling. Tell me about the Winchesters."

Castiel stares back, all traces of sarcasm gone, defiance etched on every feature as he slowly shakes his head.

"No."

Naomi takes a deep breath and regards him cooly for a second, before nodding. "Very well. I regret doing this, I really do, but you leave me with no choice. You've tasted Heaven's persuasion before, if I am not mistaken. Let's see if some of my associates can loosen your tongue."

It takes them three months to break him.

Naomi doesn't stick around for the interrogation; she has other, more important things to do, and she knows this is going to take a while. When she receives the message that he is ready to talk, she takes her time getting to him. He isn't going anywhere, after all.

The first glimpse she gets of their informant, she hardly believes he's still alive. Every inch of him is covered in blood, bruises, or burns. The only part of him that remains untouched are his wings (there are some lines even Heaven's most ruthless torturers will not cross). They are folded against his back, glossy and black. They shake as he cries.

Naomi is puzzled by the display of emotion. The pain has stopped; she cannot fathom why Castiel is crying. But she is not here to understand his emotions. She is here to collect information.

He sobs out a few short sentences through parched, bloody lips. Naomi can hardly hear him; the screaming has worn his voice down to barely more than a whisper.

Since their last chat, the Winchesters have taken on several small, relatively simple cases in rural towns in the United States. They have kept in contact with the Prophet and his mother, but their conversations never involve location. Crowley is still in possession of half of the tablet, and his whereabouts also remain unknown. Nothing has changed.

The information is useless. Naomi does not understand why Castiel has guarded it so fiercely, through such brutal torture. Nonetheless, she smiles. It has taken time, yes, wasted it even, but it is progress.

And this small victory means that breaking him will be easier the next time he attempts something as silly as defiance.

She stands and smoothes out the wrinkles in her suit before turning back to regard her spy still weeping on the rack.

"Thank you for your co-operation, Castiel," she says impassively. "As you were."

Castiel appears seconds later in a diner in Idaho, whole, without so much as a scratch on him.

"- side of fries, garden salad for you, and… for you, sir?"

He blinks. The waitress is looking at him expectantly, pen poised on the small notepad in the palm of her hand.

Right. She expects him to order food.

"Uh, nothing. I'm fine. Thank you."

She smiles, nods, and walks away. He turns to stare out the window, suddenly struck once again by the feeling of uneasiness that has been plaguing him ever since leaving Crowley's warehouse. It's worse this time than it has ever been before. He feels as though he has failed in some way, failed someone he cares about deeply. It is a ridiculous notion, of course, but one he can't seem to be able to dismiss. He frowns.

A second later, he notices Sam staring at him.

"You okay, man? You look a little, you know-" he waves his hands around his head, "spaced out."

Castiel shakes his head and forces himself to smile.

"I'm fine, Sam. Really."

Lying comes easier to him these days. He doesn't want the Winchesters to worry about him, so he keeps the truth to himself, buries it down deep along with the little voice screaming at him that there's something very, very wrong.

The truth is, he isn't fine. He's terrified. And he has no idea why.