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There wasn’t much Dean Winchester would ask for right this moment. He was… content. Well as content as someone with his past could be anyway.
But right now? Right now everything has kind of settled down. Kevin was with his mother, Sam was practically living in the library of the bunker, reading every single book it could offer - just for the heck of it for a change - and even Bobby’s soul was back safe in heaven. As were the rest of those dick angels.
So yes, Dean was content.
Except for one thing. There was missing something. Something Dean hasn’t realized until recently that he has lost way too many months ago. Something he didn’t even know he cherished as much as he apparently did.
Cas’s smile.
This particular angel didn’t truly smile anymore. Which was something that was definitely on Dean’s list of unacceptable things. So of course he planed to change that. He wanted to make him smile again. He wanted to make Cas smile for him.
He wasn’t sure if his final plan would actually succeed or cause the polar opposite but for now it was his only one. So he just went for it and made the call.
—
He didn’t tell Castiel where they were going. He just told him to get his butt into the Impala and don’t ask questions. Cas, of course, did. The ride took about an hour and a half and when they arrived they were somewhere in the nowhere.
Dean noticed that Cas started to look more and more quizzical but only smirked at him encouragingly and parked Baby. They made the rest of their way walking until they arrived at the top of a steep mountain cliff. The only thing there was a large bag lying right next to the slope.
Dean felt the angel get restless. “Dean…”
"Pssht." He shushed him and made his way towards the bag, Cas following behind hesitantly. "Close your eyes."
Castiel frowned. “Dean, what are you…”
"Come on." Getting slightly nervous himself, Dean put a hand on his shoulder. "You need to trust me on this or it won’t work, okay? Do you?"
Even though he looked vaguely frustrated, Cas nodded firmly.
The hunter huffed out a breath he wasn’t even aware he was holding. “Good, so go on. Close your eyes.” When the angel did, Dean turned back towards the bag. “Keep them closed and keep still.” Castiel hummed in agreement. Dean tried to hurry and quickly pulled out the necessary parts out of the bag. He stepped into the suit and precisely fastened the belts around his torso and shoulders. When he was done with himself, he walked towards Cas. When he slung the first belt around the angel’s torso, he felt him stiffen.
"Dean, what…?"
"Don’t worry. Just keep your eyes shut, you said you trust me, no?"
"Of course I do, but…" He squirmed. "What are you doing?"
A slightly nervous laugh left Dean’s mouth. “Wouldn’t be a surprise if I told you.”
The angel huffed. “I wasn’t aware it was supposed to be one.”
"Well, it is. So shut up and let me go on." Cas sighed and relaxed, so Dean quickly finished fastening his belts as well, pulling Cas’ back flush against his chest, securing an arm around his hip in addition to the leather. He pulled a little and then smiled to himself when everything was ready. "Now… I don’t actually want to give you a heart attack, so I will warn you that this could be unpleasant at first, but I got you, alright?"
He felt Castiel squirm again and squeezed his hip to calm him down. “You are very ah… touchy today.” The angel observed.
Dean most definitely didn’t blush. “Have to be, or this would be hell of a lot harder.” He cleared his throat. “Alright, move forward slowly and remember that I’ve got you. Don’t panic and keep your eyes closed.”
"Panic? Really, Dean what…" The rest of his words turned into a startled yelp as he most certainly felt the bottom underneath his feet vanish. Dean has pushed him. Over the cliff. "Dean!"
"Eyes closed, Cas!" Dean warned, tightening his grip around the angel’s waist.
"They are closed, Dean, but we are falling!" There really was panic in his voice but he tried to calm down.
Dean laughed into his ear, a little breathlessly. “Not for long. Just a second, you can open your eyes soon. I’m gonna need to let go of you now, but you’re secure, alright?” Slowly steadying the fall by spreading his arms and legs out, Dean managed to get them into a horizontal position in no time. “Okay, open them.”
And Cas did, quickly followed by a loud gasp. “Dean, we are…”
"Flying, yes." And they where. Flying over the sea of treetops, the wind carrying them over the world.
"Flying…" Dean heard a breathless huff underneath him. "But how… what…"
"It’s called a Wingsuit. It’s an extreme sport but I figured nothing’s actually too extreme for us." He smirked, moving them slowly to the right. He’s memorized the map the night before, he knew where they had to land.
"This… this is amazing, Dean." The words were so soft that the hunter barely heard them. He smiled to himself.
—
The flight only took a little over two minutes and soon Dean had to draw the parachute, making sure to land safely. Once they had solid ground under their feet, Castiel sagged against Dean’s chest. “Woah there, are you okay?” Worried, Dean circled his arm around his waist again.
Cas was breathing heavily. “I’m fine. Untie me.” The words where rushed and Dean made quick work to unfasten the belts, afraid his plan really did the opposite of his goal. But even before the last belt fell to their feet, Castiel whirled around and almost tripped in how fast he threw his arms around Dean’s shoulders. He hugged him as tightly as possible, burying his face in his neck, breath still shallow.
Dean gulped, not sure if everything went wrong of if his plan succeeded after all. “Cas? Are you okay?”
"I… I flew, Dean." The words were slightly muffled by the hunter’s jacket. "I was flying for the first time in months, I… I am more than fine. Dean, I don’t even know what to say.” He leaned back to look up at the hunter and Dean froze when he saw the actual tears in his eyes. Oh crap, he messed up, didn’t he?
But then… Then Cas smiled. A big, bright smile that lightened the blue in his eyes and crinkled them. “Thank you, Dean.” He smiled for him.
The plan was a success.