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There was little Dean didn't know about Castiel, from the biggest secrets, to the smallest little things that where unspoken. Castiel knew about that much about Dean, so when they found something new about each other, it was quite the surprise to the both of them.

There was one time they remember quite fondly, despite the situation. 

It was a cold night, Dean was laying on the couch, drinking a beer. The newly humaned Castiel sat on top of him casually, the extra weight bothering Dean more than he cared to admit. Finally, Dean couldn't take it anymore.
"H-Hey Cas, why don't we do something?," Dean croaked, from under the man. Castiel looked down, a tad bit of honey on his cheek from their previous meal. Dean smiled at the goofy smile Castiel wore, which was rare nowadays.
"What where you thinking of doing, Dean?," Castiel asked, his bright blue eyes meeting Dean's dark green ones. They stared at each other momentarily, Castiel's blue eyes searching Dean's as they forgot about all else. Just lost each other in the quiet green and blue daydream.
Dean blinked after a few minutes and smiled, wider than before.
"I'm not sure, angel, what do you think?," he asked, looking up at him, his breath short, making his voice breathless and a tad bit horse.
"Well, we could go for a walk," Castiel stated, nodding slowly. Dean thought for a second, and shrugged, nodding along with his boyfriend.
"Sure, but grab a jacket, its cold," Dean said, looking at Castiel's plaid robe with dissatisfaction. He never liked that robe much, covered up to much of Castiel's body, in Dean's opinion.
Castiel nodded once again, before jumping up and accidently hitting his leg on the coffee table. He let out a loud growl, as he tried to act as if he didn't already have a new bruise forming. Dean winced at Castiel's growl, knowing that Castiel still wasn't used to the human form of pain. His sorry filled green eyes met Cas' pain filled blue ones, as Dean stood as well.
Dean was in some baggy pajama pants, and a white T-shirt, both of which hung loosely around his frame. Castiel took that moment to admire Dean's firm stomach, and hard muscles. He felt his cheeks heat up when his eyes landed on Dean's freckled cheeks, just the slightest bit. There was always a deep love for those freckles buried deep in the ex angel. They had always reminded Castiel of stars.
Castiel felt his face turn a slightly pinker shade as his eyes went from the man's freckled cheeks to the plush pink lips in the middle of them. He almost shuddered at the thought of what those lips had done to him just a few hours ago, but he bit the urge Back.
Eventually Castiel's wondering eyes landed back on Dean's mildly amused ones, as those lips curled into a deep pink smile.
"Take a picture, Cassie, it lasts longer," Dean's rough voice said, playful anger in his voice. There was no doubt in his mind what Castiel was thinking of, because he couldn't stop his mind from wondering there as well.
"I'll go get my jacket, meet you at the door," Castiel grumbled, shocked he'd been staring long enough to have been caught. He quickly scurried away, leaving Dean a smiling mess in the living room.
Dean smiled as he walked to the door, now in a more out doors appropriate outfit. He shrugged his jacket on as he heard some quiet shuffling behind him, and then a small grunt.
Dean slowly turned around to see a slightly overdressed Castiel.
"Cas, you dont have to wear every piece of clothing you own to go outside for a walk," Dean said, chuckling a little as he pulled off one of the extra jackets Castiel had on. Cas pouted, looking down slightly.
"But its cold, and last time it was cold, I got sick," Castiel stated, confusion written on his features. Dean couldn't help but let out a loud chuckle, though he tried his best to hide it as a cough.
"No, Cas. You got sick because you wore just a shirt and some pants. You can get away with only wearing a jacket and some good, thick shoes," Dean stated, as serious as he could be under the circumstances.
"Okay," Castiel said, bending down to remove the extra pants he had on. Once he was properly dressed he looked up at Dean, almost for approval. Dean smiled and wrapped his arm around the slightly shorter man casually, before heading towards the door. A silent okay.
The two men silently wondered into the grass, the only sound their footsteps. Castiel's hand slowly ventured towards Dean's, inching its way into his grasp. Dean couldn't help but smile, shaking his head as he looked forward at the dark night around him.
"Hey Dean, where do you think we are going?", Castiel asked after they'd been walking for awhile. Dean let out a grunt, along with a shrugged. Castiel nodded in response, biting his lip as he stopped slowly. He found himself looking up at the sky, his blue eyes staring up at them. Dean felt his hand tug as he started to walk, then turned back and looked at what was stopping Castiel. Castiel's eyes where wide, almost innocent at the bright stars in the sky. Dean looked up as well, his eyes twinkling against the bright stars.
"Wow...," there was only one whisper, the both of them awestruck at the twinkle.
There was a long while before either of them spoke, though their hands never each others.
"You know, Dean.. The stars, they remind me of you," Castiel mumbled, his eyes barely moving from the sky as he went to glance at the man.
Dean stopped staring at the sky, his eyes surprised as he looked at the ex angel.
"You- Why's that?", Dean asked, his face red in the dark moonlight. He felt his ears head up against the cold air of the outdoors.
"You're freckles," he mumbled, his eyes dancing with Dean's.
"My freckles?", Dean asked, his eyes soft against Castiel's. He barely croaked it out, the lump in his throat forming hard.
"Yes, your freckles. They always remind me of the twinkle of the stars, the view I always got from heaven," he whispered against the sounds of the night, and the drum of his own heart in his ears. He felt his cheeks heat up at the gentle love in his eyes.
"Wow," was all Dean could force out, the lump in his throat growing thicker. He couldn't get himself to say more, all he could do was stare into his blue eye'd angel.
Dean's eyes spoke volumes more than his voice did, as he leaned in to touch Castiel's cheek. Castiel smiled gently, as he touched Dean's back, his cold fingers against the cheeks softly. Dean felt himself breath in. There was a spark against his cheeks where the fingers just were. They stared up at each other for what felt like hours, before Dean finally got the courage to move closer and press his firm lips against Castiel's. Dean felt himself lock up, not sure what else to do. When it came to romantic, fluffy, chick flick stuff, Dean was no good. He always fumbled and tripped over his own feet. Flirting he was good at, romancing, not so much.
Castiel's lips moved against Dean's ever so gently, the crisp night around them nipping at their blushing cheeks as they kissed in the night, the stars shining up above.
Almost brighter than before

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