The first time you kill Dean, he doesn't say anything, just stares up at you with open eyes as your hand tangles in his jacket, the other gripping a blade. "You have to run," you tell him, "just run." He doesn't, though, and neither do you.
She's behind you, that ice angel on your shoulder, coaxing you on, a dedicated coach. "Bring you arm down, Castiel. It's simple. One simple movement, like swatting a fly."
You won't listen to her, you tell yourself, you won't do it, but there's something heavier than words in the weight of what she says, and before you can stop yourself you've driven the blade straight through the man in front of you.
The third time, you manage to throw the angel blade across the wide white room, barely noticing as it arcs through the air, a silver flash. Your eyes are on Dean, checking to make sure he's okay after you threw him on the floor.
You kneel in front of him, level, and you put a hand on his shoulder and nod. "I'm going to get you out of here," you promise. "I'm going to save you." But the blade is returned to your hand, and Dean is focused on your face so it would be so easy to catch him off guard, one simple movement…
The seventh time is the first one where Dean talks. He begs, first, and that catches you off guard. You stand there frozen, blade raised above your head while he pleads, "Cas, don't, it's me." The blade falls from your hand, its clatter echoing in the empty expanse.
"Dean?" you say, cautious, because the Deans you've killed never talked before and maybe this is him, maybe this time it's real and there won't be another Dean around the corner. His expression opens up like he's not so scared, like he trusts you and he's worried about you even though the worst is over, and you can feel a tug from inside you.
"Yeah, Cas," he says with a faltering smile. "Yeah, it's me." Shame curdles in you so much you nearly flinch, that this is your best friend and you could've hurt him, could've… "It's okay," he says quickly. "Cas, it's okay. It's okay, it's okay." He says that and he keeps saying it and he's still saying it when you snap his neck.
After that they all fade into each other, like extras getting killed off in one of those movies the real Dean might watch. There are milestones. The twelfth Dean runs, finally, but you catch him. You always catch him. The fifteenth Dean fights back, and you dispatch him quickly. The twenty-first Dean tries to give you this big speech, "You don't have to do this, Cas. I know you're in there, I know you…"
You cut him off.
The forty-seventh Dean tells you he loves you, and you're scolded for weeping when he dies. Dean number sixty-three tells you to go ahead and kill him, and that he forgives you, he forgives you for everything. You almost hesitate when you stab him in the chest.
The seventy-eighth time Dean screamed like he had in Hell, and the eighty-third time he whimpers like a child, but none of them are as bad as the ninety-ninth time.
The ninety-ninth time you kill Dean (and you know, because you've counted them like scars), he twists beneath your arms as you drive the blade down, watching him convulse and then stop, dead. It's the worst time because you realize, as the light leaves Dean's eyes, that you didn't feel a thing.