Dean had never been so sure of anything in his life. He was sure this was the worst idea he had probably ever had, but he was also sure it was the only option they had. He'd do it for Sam. He'd do it for Jack. There wasn't anything he wouldn't do for his family. And right now they needed him.
They needed someone to beat Lucifer. The only one who could beat Lucifer was Michael. But with all that extra Nephilim juice, Michael needed his sword. Dean. It was crazy, and deep down he knew it wouldn't end well. Yet he was so willing to give himself over as a vessel that his chest ached.
It was the only was to save Jack and Sammy. And the world, again. His bargain was ridiculous, he could see it in Michael's eyes that he would never hold up his end. Michael in his suit, but Dean stays in control. It was the only way he could convince himself to say yes. Cas was here to vouch for the deal when Sam would undoubtedly throw a mental fit over it. Cas…
If he said yes to Michael now, he'd never see Cas again. No more Sam, no more Jack, no more Mom. No Bobby and Charlie. Even if they were the alternate reality versions, he'd still miss them like hell, just like he missed his own versions of them everyday.
But he was tired. Tired of fighting, tired of losing. Tired of losing everyone he loved. Earlier he had been telling Sam that they should retire. It was a foolish thing to hope for, they both knew it would never come true. But it was a nice thought. Sam, Dean, Cas, matching Hawaiian shirts, toes in the sand, ice cold drinks and an endless horizon of water… Something that would never be, no matter how much they deserved it.
Again, Michael asked for consent, and Dean just stared into his cold, ruthless eyes, knowing that this was the last time he'd ever be free. Before he answered, he turned to Cas to say goodbye. The only thing that hurt more than knowing he would never see his Angel again, was seeing it written on Cas's face that he knew too. Bracing himself, he leaned in to do the one thing he had always been too afraid to do.
Dean put as much emotion as he could into that kiss. Their first and last. Looking back, it had been stupid of him never to do it before. But it was too late to change the past, so he'd just have to make up for it now. Time stood still, but by the time Cas started kissing him back, Dean had pulled away, careful not to look into those beautiful blue eyes. He was terrified of what he would see there, more than he was of saying yes to Michael.
"I Love you." It was barley a whisper and as he saw Cas open his mouth to reply, Dean twirled around to face Michael instead, uttering one word before his reality fell apart. "Yes."