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He wanted to tell him how much he loved him but ever since he had realized what he was feeling when he laid eyes again on his best friend in Purgatory after weeks of looking for him, it was like time, fate, destiny and everything imaginable was working against them.
There was not a single moment in Purgatory where he could have taken his time to take Cas to the side and reveal something like that, not when they could die at every moment and even more danger lurked around the corner. Dean didn't want his life to turn even more into a chick flick by having that confession be the last thing he ever said to Cas, he didn't deserve that and Cas sure didn't deserve that even less.
Dean also didn't know if he was ready because if he was being honest this epiphany scared the hell out of him, he hadn't been prepared for those thoughts crashing over him. The whole last year hadn't been enough to prepare him for the clues to finally clink together. Ever since Cas had gone behind his back to work with Crowley of all people, Dean had realized that as much as he was hurt because of the friendship Cas had betrayed in some way, he had been triggered in other ways even more. Dean Winchester had been jealous.
And Dean Winchester didn't handle jealousy well.
Not at all.
And then he had just come around and gotten Cas back, for that one split second where he had begged for forgiveness before the Leviathans had eaten him. He had held in that trenchcoat in his hands and he had wondered just why this hurt so much more than the other times before. He had lost Cas before, he had seen him getting exploded right in front of his eyes, so why had this hurt so much more...
Ever since, ever since...
So many ever since.
Later and later finding Cas again, finding him not knowing who he was, living with this woman, looking happy, looking happier than his Cas had ever had around him.
Dean Winchester did not carry jealousy well.
He had told himself this desire to have Cas remember was just because they needed him, they needed his help, and he needed his friend back. He hadn't let himself think that it was something else as well, it wasn't the place, it wasn't the time.
But when was it ever.
When was it ever indeed.
Cas had remembered but he also sacrificed himself for Sam, and once more Dean had had him back for only that split short moment.
Time was not on his side.
Especially not in Purgatory.
Once reunited they were never alone, Benny was always there, monsters were always there. An Angel and a Winchester, a beacon in this dreadful place, a beacon to get revenge. And a Dean who was bursting at the seams with something he was so scared of, more scared of than he had been of Archangels and Apocalypses.
The last person he had let his heart open to in this way had been Lisa and look what that had gotten him, and most of all her. He had lost Lisa and Ben forever, to keep them safe, safe from him and that toxic stain surrounding him and corrupted everyone coming too close. Like it had corrupted Cas as well a long time ago.
And still, every single time they settled down to rest for a while because Dean was still only human, his mind began to turn in circles while Cas kept close to protect him as he rested. Every single time. Around and around and around. And every single time he told himself 'I'm gonna tell him when we're out. I tell him and then we find Sam.'
He got out.
Cas didn't.
He lost Cas again. Without having told him how he felt.
Dean was truly destined to end up alone.
In the weeks that followed as Sam and him got into arguments, as he was eating at himself in guilt over what had happened at the portal, as he watched his hands in the night and saw Cas slip out of them again, he knew without a doubt that he would regret not telling Cas right away for the rest of his life.
And then Cas came back. He came back.
And he revealed that Dean hadn't abandoned him. That he had chosen to remain for penance.
Dean hadn't known what to say but in his head he had been screaming.
'I love you, I love you. Don't ever leave me again. I love you.'
--
His inner desperation to do something before time robbed him of his chances again built up and up, right until that moment where he was alone with Cas in their motel room during this weird Bugs Bunny case.
That intense reaction against Heaven.
"Talk to me."
The guilt in blue eyes.
"I caused a lot of suffering on Earth but I devastated Heaven."
Hearing him say he was afraid he might kill himself if he only made one step back into the field of slaughter he had made of Heaven when he hadn't been in full control of himself.
It became that moment.
That one moment.
--
In another world Sam would have barged into the room at that moment because he had found something for the case. In another world they would have brushed past that moment and never gone back to it. In another world Dean would have lost that moment because time would have once more been a bitch.
But not now.
Not here and then.
Dean reached for Cas' hands, wrapped his fingers around them, holding on when Cas almost instinctively lurched back, confusion taking over from guilt in his eyes.
"Dean?"
"You gotta listen to me right now, okay?" Dean began and Cas looked so lost, Dean squeezed his fingers, stroked a thumb over smooth skin. "Yes, you fucked up with the souls, with working with Crowley in the first place but even you are allowed to make mistakes. You're allowed to fuck up. Then you apologize and fix what you can. You did penance in Purgatory, I'd say that's about as rough as a punishment as it can get."
"Dean, I hurt so many people and I slaughtered the angel. My own brothers and sisters," Cas choked out and his hesitation turned into something entirely else when he clutched at Dean's hands now.
"And can you say that they wouldn't have done the same to you before?" Dean gently argued right against him, "You said it yourself you rebelled against Heaven. For me. So I wouldn't say yes to their precious Prince of Heaven. You helped put both of those super bastards into the Cage. Raphael already proved to me that Heaven had it out for you."
"Still, they were my family."
"Sam and I, we're your family, too," Dean pointed out and Cas dropped his head forward, eyes set on their knees that were touching now where Dean had slid more towards the edge of the bed. "Cas, look at me. Please." Blue eyes got raised again and Dean tried to smile even though his heart was going a mile an hour and this had to be one of the most terrifying moments of his life, even though he was in absolutely no danger.
Dean didn't talk about these kind of things but he couldn't let another moment go to waste.
Who knew what would soon come their way.
What catasstrophe would be unleashed upon them next.
Dean took a deep breath and moved, he let go of Cas' hands and framed his face with his own just as he stood up. He leaned down and closer and waited for a brief moment to see if anything else but that tiny spark of hope would flicker up in still confused blue eyes but nothing else appeared. So Dean crossed that last short distance and pressed his lips to Cas' in that first careful kiss, he smiled when Cas sighed right into it and let his eyes fall shut. He did the same and then Cas was kissing him back, trembling hands coming up to rest somewhere on Dean's waist, at least until Dean smoothed his hands down Cas' neck and shoulders to push him down onto the bed.
He followed him without breaking the kiss, something he regretted slightly when they shifted both at the same time to get more comfortable and Cas accidentaly kneed him in the stomach. Dean gave an "oomph" and all but faceplanted against the angel's chest which in turn had Cas grunt. "We're just glorious," Dean deadpanned when he had picked himself up again onto his elbows at least and he smiled at Cas, a smile that turned into a grin when Cas chuckled.
Unspoken they rearranged themselves until they were lying down properly on the bed with all limbs on the mattress, Dean shifted himself until he was propped up on his side, one hand free to trace over Cas' face, fingers trailing over cheekbones, jawlines and lips.
And then it was just easy.
"I love you."
The emotions that lit up Cas' face in the next second were worth all the doubts, all the fear, all the hesitation.
"I love you, Cas," Dean repeated and cupped Cas' face with one hand, "fuck Heaven. We did it without them once, we can do it again, whatever comes. You, me, Sam, that's enough. That's family. Mine and yours." Cas nodded, shakily breathing out.
"Dean, I... I love you, too."
--
When Sam ultimately returned and stepped into the room with his "Hey, got something" it was immediately followed with a yelped "Hey, woah, they did invent the sock on the doorknob for something, guys!"