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That morning as they packed their bags to leave the hotel after a successful hunt Dean gave himself a deadline to tell Sam in five years maximum.
After two hours on the road he couldn't take it anymore and he parked the Impala on the side of the road.
“Why did we stop?” Sam asked.
“I have to tell you something and I don't want to do it while driving.”
"Okay tell me."
Dean took a deep breath, now there was no turning back.
"I’m bi."
He took a deep breath once more. He was officially out of the closet, true he hadn't told everyone but he had told the person who mattered the most. It was done.
Sam smiled at him, Dean waited for him to say that he was happy for him, and that it didn't change anything, maybe even that he loved him. Instead what Sam said was:
“I know, I always knew.”
Sam's tone was affectionate but there was also another tone in the middle that seemed to say Oh Dean do you really think you can tell me something about yourself that me the great and wise Sam Winchester hasn't been aware of for a million years, oh my how adorable .
“Did you always know? Really?”
“Well not always, but for basically the last decade, yes.”
"Okay now I know you're lying because ten years ago I had no idea."
“Well maybe you're not very good at noticing things, that's okay. You have other qualities…so is there anyone specific that made you have this realization about yourself?”
"Oh you said you know everything, you don't know who it is."
"Actually I'm pretty sure I know, but I want to hear you say it."
"The only thing you'll ever hear me say is you're an smug asshole."
Sam laughed.
"But seriously Dean, thanks for telling me, it was really brave, I'm proud of you."
"Whatever." Dean said and started the car.
They had barely made it back onto the road when Castiel appeared in the backseat. Sam smiled at him and said:
“What a coincidence Cas, we were talking about you just now.”