Castiel had imagined it happen a thousand times, maybe even a million. It was, after all, his job to do so. In order to protect his charge, he had to imagine worst case scenarios every second of every minute of every day.

Of course, those were all imaginary scenarios. He'd seen gruesome things in his mind's eye. Demons ripping flesh, hell hounds tearing muscle, monsters as terrifying as God himself sneaking out of the darkest corners of the night and destroying the very thing Castiel had worked so hard to protect - Dean's life.

He'd imagined it in every way, but never by his hand.

It was as if his mind was speeding into overdrive, trying to think of anything possible to stop what was happening. But he couldn't. There was no answer, no quick fix, no easily healing fingers. Nothing. Nothing to save his charge. Dean Winchester was dying by his hand tonight, and there was nothing he could do to stop it.

Castiel held Dean in his arms, pressing his thin hand over the wound in Dean's chest. It wasn't doing any good. Blood gushed out of Dean's chest, the stark red colour contrasting against Dean's pale face like some sick form of modern art.

"Dean," Castiel said, voice thick. "Dean, stay with me." His hands were shaking now. He needed to remain calm and steady, but he was losing his grip on his emotions. It wasn't as easy to control them now that he was human.

"Cas…" Dean wheezed, gripping Castiel's trenchcoat, jaw clenched in pain. "It's okay."

"No…" Castiel shook his head frantically. "I can…I can fix this." He scrambled to remove his coat, and wadded it up, pressing it harder on Dean's wound. "I'm sorry," he gasped, trying not to break into tears.

"It's okay," Dean reassured him weakly, attempting a smile. His freckles were dark against his ivory face, and under any other circumstances it might made Cas smile.

Castiel shook his head harder. His throat hurt, and he felt sick. His vision was blurring. Something warm and wet was streaming down his face - tears. He'd never cried before.

"Dean, I c-can't save you this time," Castiel said, biting his lip, trying to stop the tears from coming.

Dean gave a stiff nod. "I know."

Blood was accumulating in a small pool around them. Castiel's shoes were wet and sticky with Dean's blood, and it nearly made him sick.

He couldn't just stand there and watch Dean die. Dean wasn't just his charge anymore. Dean was his friend. Castiel was cursing himself because he'd let himself get too close. Because he'd let himself care.

Because he'd let himself fall for Dean, who was now dying in his arms.

What would he tell Sam?