Attempt 1

Castiel doesn't know why he's there the first time.

When he sees Dean, he thinks Dean's come to save him. He knows something is wrong. Heaven is not right,Castiel is not right. He needs help. He needs Dean's help. He rushes to Dean, calling his name, but as Castiel reaches for him, he dissolves into the air.

Cas is left alone in the huge warehouse.

Attempt 2

Naomi tries yet again to explain to Castiel that no one must stand in the way of reaching the tablet. Anyone, even the Winchesters, must be eliminated if they are endangering the tablet.

Castiel is confused, but does as he's told. When entering the warehouse again, he sees them. The two brothers are walking there, in front of him. He hesitates, unsure of what to do. Naomi urges him to kill them. He walks closer to them. He's behind them now, the blade in his hand.

Dean turns around.

He smiles.

Cas stops dead in his tracks. He can't do it.

Attempt 7

Castiel doesn't even try.

Attempt 11

He sneaks behind them, hoping they won't turn around. He touches Sam's shoulder, keeping him in place as he raises the blade. Dean turns around, with wide eyes, yells out "Cas!"

Castiel can't do it.

The two brothers fall on the ground by themselves, leaving their motionless shells on the floor.

Attempt 15

Naomi talks to him. She tells him lies. She tells him that the brothers, they're working against the angels. Cas knows this isn't true, but he listens and nods.

The brothers are walking through the warehouse again, Castiel tailing them not far behind. He hurries soundlessly up behind Sam, grabs him by the neck and forces him downwards. He raises his blade to Sam's throat, Naomi urging him on.

Dean begs Cas not to do it.

He doesn't.

Attempt 19

Castiel pins Dean to the ground, and cuts his arm in doing so. Dean yells out in pain and squirms beneath him.

Cas teleports away. He stands in the other end of the room, breathing harshly after wrestling Dean to the ground. He's shaking.

He can't do it.

Attempt 25

Castiel manages to grab onto Sam again, bringing the blade close to his huge chest, even though Sam's resisting. The man is strong, but not as strong as Castiel. He manages to stab him, albeit slowly. Something inside his mind is screaming, telling him this is wrong, everything is wrong. Sam's yelling and resisting, but goes still.

Castiel feels like his insides are turning out.

Even though he doesn't touch him, Dean falls to the ground as well, moments after Sam died.

Naomi walks over and puts a hand on Castiel's shoulder. You did well, she says.

His mind is still screaming.

Attempt 30

After several practices of killing only Sam, Cas barely flinches when he stabs him this time.

Dean is nowhere to be seen among the corpses of his brother.

Cas doesn't want to do this anymore.

Attempt 33

Naomi decides to only practice on Dean.

Castiel refuses. He tells her it is not the right thing to do, Dean is innocent.

She kills Dean herself out of frustration.

Cas yells at her. "No!" he screams, but too late. Dean's lifeless body crumbles to the ground.

Cas crumbles with him.

Attempt 37

Castiel can't sense Dean's soul. This isn't Dean he tells himself. And yet, when he looks at Dean's face, he recognizes the bright green eyes. He can't bring himself to do it. The blade slips through his hands.

Dean drops dead by himself again.

Attempt 40

Cas punches Dean. He slams him to the ground, knocking his head. Dean groans and bleeds beneath him.

Cas is so confused.

Dean is hurt. Why is he hurt?

He reaches out to heal him. Dean's body falls to the ground and his skull cracks. Castiel stares horrified at the corpse, until he realizes it was Naomi who killed him yet again.

Cas feels his skull breaking too.

Attempt 42

When Cas approaches Dean this time, he talks.

"Cas?" he asks, looking worried. He reaches for his gun. Castiel knocks it away.

"Cas, what are you doing?" Dean says now, voice raised.

Castiel hits him, grabs him by the arm and forces him down.

A small blood streak slides down from Dean's right eyebrow, where Cas hit him.

"Cas, no, please don't do this..!" Dean begs, winces when Cas raises his hand again. He grabs blindly at Castiel coat.

"I'm …." Cas starts. Naomi interrupts him, yells at him to do it, to finish it.

"Dean I," Cas falters, his hand falters, his mind falters, everything stops.

He stares at the man before him.

He turns around.

Naomi yells at him again.

Castiel doesn't care.

Attempt 46

Naomi tells Castiel he mustn't speak with Dean.

Instead, while Dean pleads, he looks in his eyes.

Castiel gets lost in Dean's eyes.

Attempt 53

Castiel breaks. Slowly, one at at time, pieces falling from him.

He doesn't get lost in Dean's eyes anymore.

Bit by bit, something inside him breaks, every time he breaks Dean's skin, every time he hits him.

He breaks down next to the beaten Dean.

Attempt 58

Castiel barely feels anything as he beats Dean down now.

He wishes Dean would just shoot him with the gun he holds.

Dean almost does.

Cas breaks his wrist.

The crack echoes through the warehouse.

Castiel can feel it echo through his being.

Attempt 66

Castiel beats Dean down.

He acts by himself suddenly, Naomi's orders ringing through his head. His arm comes down in a swift movement and the blade pierces Dean's chest.

As the body drops to the floor, Castiel suddenly realises what he's done.

Another piece breaks off inside him.

Naomi rushes to Castiel before he stabs himself.

Attempt 68

After Castiel stabs Dean, he cradles him close, whispering soft words to the moaning man.

"It's alright Dean," he mutters, lips pressing against Dean's temple. "It's alright."

It isn't.

Attempt 71

"Cas, please, this isn't you, I don't understand … Cas… Cas..!"

He stares as the empty, bloody body falls to the floor.

Castiel feels empty.

Attempt 79

Dean almost cries.

Castiel's heart breaks.

Attempt 81

Dean cries for Sam this time.

Attempt 87

Castiel tries to stab him from behind, tries to avoid seeing Dean's face.

He still feels that twinge inside him.

He wished he could die instead.

Attempt 274

He flinches when Dean says his name.

Attempt 283

He's not quick enough.

Naomi wants it quickly done.

Attempt 372

Dean says something different.

"I trusted you," he whispers, before the life fades from his eyes.

Cas doesn't know how to react.

There's nothing left to break.

Attempt 823

Castiel kills Dean.

He falls to his knees besides the body.

He doesn't know what to do.

Attempt 1031

"No, Cas .. No…!"

Dean crawls away from him.

"No, Cas, don't … please.."

Castiel raises his blade.

He kills Dean. Doesn't even flinch. Doesn't even blink.

Doesn't break.

"No hesitation. Quick, brutal… Everything's back in order."

She smiles.

"Finally," she says. "You're ready."