Dean's eyes could barely open, weighed down by a sweet, blissful sleep, holding them together like glue. Taking a deep breath through his nose there was an odd smell; it wasn't bad, only slightly unfamiliar. 'It smells like cinnamon...and watermelon?'

He tried to turn away from the glaring light that was currently trying to burn through his eyelids but the slight shift caused him to realize that there was a weight resting on his chest. For the first time, he actually peeled open his eyes and looked at where he was. 'This...isn't my apartment.'

Those words were usually followed by dread and slight panic, especially if you knew you were drinking your troubles away at a club the night before. 'Seriously? Why do I keep waking up everywhere but my own bed?!'

His first conclusion was that he was either kidnapped or was so stoned that he redecorated his entire bedroom in a night. Okay, maybe not that last one but Dean thought about it for like...a second.

A glance down at his chest helped to calm the momentary panic. His vision was mostly obscured by messy black hair and memories of last night's events. A gentle snore broke the clip show and Dean smiled down at the man sleeping soundly on his chest, absently running his fingers through his soft hair.

He lay his head back against the pillows and sighed, content to go back to sleep. His other arm moved lazily over Castiel's waist causing him to nudge further into Dean's side while remaining blissfully asleep. Dean couldn't help but think that this was nice. Waking up to Castiel felt almost natural as if they haven't just met. It just felt like a peaceful Monday morning filled with blissful sleep and –

Wait.

Monday?!

Dean's eyes flew open and he grabbed the clock on the nightstand almost knocking a lamp over. It read some minutes to ten. He felt like he was gonna have an aneurysm.

Somewhere in the middle of the screaming thoughts telling him he was so very screwed, and not in the nice way he had previously been thinking about, he remembered that he, in fact, had a very beautiful angel sleeping on his chest and if he propelled himself from the bed like he had been planning to do it would make for a very rude awakening.

So instead he made a more civilized decision. He slowly pried himself from Castiel's grip making sure that the other man was still asleep and carefully slid off the bed to try and gather his scattered belongings. He was late already, so why rush the inevitable.

He found his shirt mixed up among the bed sheets and quickly dragged it on. It felt tighter around the arms and shoulders than last time but he paid it no mind as he searched for his pants while picking up his boxers from off the floor. The pants he located hanging over the bathroom door quite a distance from the bed. How they got there was beyond him, though he did remember last night being a bit...wild.

Looking around a couple more times he failed to locate his jacket or his shoes so he bent to look under the bed where he found his phone.

'Five missed calls from Sam...he does care' he smiled and grabbed his keys and wallet that were some distance from the phone.

When he got up Castiel was rubbing his eyes, his legs crossed over the sheets and a pillow tucked conveniently between them. He yawned and Dean smiled "Mornin' Sunshine"

Castiel blinked a few times obviously still groggy with sleep and gave him a lopsided smile, tilting his head as Dean tried to straighten his shirt.

"Good morning Dean...I believe that's mine" he pointed to the shirt that was struggling to cover Dean's chest and Dean followed his finger looking down at it too, brows raised and lips pursed.

"Well that explains a lot"

Castiel leaned over to the pillow that Dean had slept on; reaching behind it he brought out a crumpled white shirt similar to the one Dean was wearing. "And this one is yours"

He climbed off the bed, letting the sheets drag behind him and fall from around his waist. He started to undo each button slowly and Dean watched his fingers intently. When Castiel reached the last button, he trailed his eyes up to Dean's exposed chest, pausing briefly at the odd gold necklace hanging on a black corded string around his neck, then finally to the eyes studying his every move.

"It was a gift from Sam when we were in high-school."

"Sam. That very tall friend of yours who seems taken with Jessica?"

"Yup. That's the one"

"He has good taste" Dean raised his brow, dismissing the twinge of jealousy in favour of the feeling of Castiel brushing his palms over his chest. Castiel then moved his hands underneath the shirt, pushing it off Dean's shoulders. Dean shrugged it off the rest of the way letting it fall as he leaned down to kiss Castiel's lips.

Castiel smirked into the kiss, draping the shirt he was holding over Dean's shoulders and pushing gently against his chest. "As much...as I like this-" Dean kissed him again interrupting his sentence.

"-You...have to go to work"

"...psh, I'm already late" Dean whispered.

"Dean..."

"Fine" he pulled his shirt on properly as he left the room looking for the rest of his things. Castiel grabbed the sheet off the floor and draped it around himself to ward off the cold morning air, and followed Dean to the living room.

Dean found his suit jacket over the couch and pulled it on not bothering to button it up and stepped into his shoes near the door. Castiel had never expected his morning to play out like this, like a scene from a domestic romance novel, but god knows this was a welcomed change.

As Dean stepped through the door, Castiel had enough confidence to grab his hand, holding the sheet around his body with the other. Dean turned to him surprised.

"C-can I see you again...tonight?"

Dean stared at Castiel for a few minutes, studying his shy smile and his hope-filled eyes. His heart fluttered and when he finally spoke his voice came out breathy "Sure, Cas..."

Dean made a mad rush for his office as soon as he drove away from Castiel's apartment. He managed to reach his building in less than twenty minutes, record time considering the traffic in between. He stopped at the lobby's cafeteria for a bagel and coffee, whipping out his phone while he waited.

Dean: 'Sorry for the rush, the first day as CEO and I am sooo late'

The waitress came back a couple minutes later with his coffee and he thanked her, speed walked to the elevator and pressed the number of his floor taking the time to get a sip of his beverage. His phone buzzed and he looked down at the reply.

Cas: 'Well, at least no one can fire you, Mr Executive Officer' that was followed by the winking emoji with its tongue sticking out.

Dean snickered despite himself, realized what he did and coughed nervously, subtly looking around to make sure no one was in the elevator with him. In hindsight, he should have done that in the first place.

Dean: 'Was that a flirtation?' he typed out quickly as he got off the elevator making a beeline for his office and trying not to get noticed by anyone. He waved to his new secretary at the door.

Dropping his bag on the couch near the door, not bothering to take in the look of his brand new, extremely huge, view of the bay office, he sat down in the plush leather armchair behind an oak desk.

Cas: 'Hey, that's my line'

Dean rolled his eyes.

Dean: 'So, what do you actually do during the day, don't tell me you really are a tax accountant'

Cas: 'Haha, no. That seems like a dull job, no offence to the tax accountants of the world of course'

Dean paused in the middle of typing when there was a knock at the door. "Uh, come in!"

A short young woman came in carrying a stack of papers. She looked like she was barely in her twenties, her medium length, curly black hair was caught in a sideways ponytail tied off with a big cream coloured bow. Dean recognized her from the desk at his offices' entrance; his secretary.

Dean forced a smile as she came in and placed them on his desk. He eyed them with dread "These documents need your approval Sir, and I was told to inform you that there will be an important meeting at around 2 this afternoon"

"Okay, thanks..." Dean glanced down at the name tag on her cardigan "Nancy"

She nodded shyly and smiled "You're welcome Mr. Winchester if there is anything you need please don't hesitate to ask"

Dean nodded and she continued smiling as she turned on her heel and walked briskly out of the room.

When the door closed he narrowed his eyes at the pile of papers, picking his phone up to resume typing.

Cas: 'I'm actually going to visit my little brother later, he needs some help with a biology project.'

Cas: 'I have to stop by one of my older brothers first to ask for a ride though...

Cas: 'Can't afford a car on a bartender's salary, unfortunately'

Dean: 'You seem to have a lot of brothers'

Cas: 'Yes. I'm the second youngest of five children.'

Cas: 'Michael is the oldest, then Balthazar, Gabriel, me and the baby, Samandriel'

Dean: 'Oookay...what is up with those names?'

Cas: 'Well, they're the names of angels. My family is very religious. It isn't a coincidence that I work at a bar named Heaven, you know'

Dean had to fight the urge to throw his head back and laugh, which resulted in a series of stifled giggles and long, silent, open-mouthed gasps. If anyone saw him like this he would probably shoot them...then himself.

As if to test how true that statement was, the door flew open and he slammed his phone face down on the table so hard he actually flinched afterwards, praying that the screen hadn't cracked. It would be a bitch to replace.

Standing in the doorway was none other than Sam. Only that giant man-child would have the audacity to open the door to an executive's office in such a manner and stand there grinning like an excited puppy.

His grin turned into a cheeky smile coupled with a raised brow when Dean let the tension loose from his shoulders and rubbed his brow. "Sam...what are you doing here? Don't you have work to do?"

"Came to check out the new office" He grabbed one of the two smaller leather chairs in front of the desk, spinning it around so he could sit down with his legs on either side and his elbows crossed on the back. Dean vaguely wondered why he couldn't sit like a normal person then remembered that Sam was anything but normal.

"You couldn't come up with a better excuse to get out of work?"

"Nope." Sam smirked looking around with mock interest at his surroundings "Pretty fancy"

Dean rolled his eyes, pushing the phone away subconsciously. It flipped over as he leaned back in his chair. Thankfully the screen wasn't broken.

He stared disinterestedly at a random abstract painting on one of the walls near the private bathroom and sighed. "Yeah, I guess. Didn't really notice"

"Oh? Thought you were excited to see the place, the way you were speeding up here. Could barely get your attention cause you were buried in your phone and you couldn't even bother to call me back? Why the heck were you late this morning anyway? You're never late-"

Dean's phone interrupted Sam just then and they both looked down to see that he had received a new message from 'Cas'.

Sam's grin came back full force. "You should go ahead and answer that"

Dean blushed slightly; grabbing the phone he glanced at the message and smiled again before remembering he was being watched by a pair of amused honey brown eyes. He cleared his throat and put the phone face down as far away from his friend as possible. "It's not important"

"Uh huh" Sam cocked a brow, the smile never leaving his face "You don't have to be embarrassed you know, he's cute."

Of course, Dean chose that moment to take a sip of his previously neglected coffee and almost choked.

Sam burst out laughing when Dean spat some of the coffee onto the desk and cursed as some got on the front of his shirt. It took Sam a couple minutes to compose himself but he almost started laughing all over again when he saw Dean's expression; eyes bugged and jaw hanging open in shock.

"Oh man! I should take a picture of that face you're making and send it to Charlie!"

"Sam...What the hell?!"

Sam wiped an invisible tear from his eye and sighed exaggeratedly in content, leaning back in his chair and crossing his arms behind his head. "Well...I did have the pleasure of meeting 'Castiel' last night when he came looking for you"

Dean could only stare at his best friend, a mixture of annoyance, confusion and embarrassment swimming on his face. He wasn't particularly upset that Sam knew, wasn't like he didn't want to tell him. The problem was that the moose had found out on his own and so Dean would never hear the end of it.

"So..." Oh god, here it comes "Get up to anything interesting last night?"

"No"

"Aww, was he that bad?"

"Shut up, Sam"

"Did he take you to heaven?"

"I will shoot you"

"Psh. You might as well tell me all the details, I'm not gonna stop bugging you"

Dean leaned back in his chair and sighed, furrowing his brow. He felt a migraine coming on. God he hated Sam sometimes.

"Let's just say, mixing drinks isn't the only thing he's good at"

Sam wore an expression of shock, but mostly he was just giddy, so giddy that Dean could clearly see he was resisting the urge to bounce in place. His excitement was barely contained in his voice. "Is...Is that why you were late this morning? Oh wow"

"Yeah yeah" Dean waved him off silently wishing Sam would leave now, because he actually had work to do, not because he wanted to go back to texting. Of course not.

"So, what are you gonna do about Jo?"

And there was the question he didn't even know he was avoiding.

"There's nothing to do about Jo"

Sam raised an eyebrow surprised, "So you're planning on dating them both? You know I'm all for living life to the fullest but-"

"It's not like that"

"Then what's it like? Don't tell me this is just a one nighter, cause it sure as hell isn't, obviously and if you really believe that, I'm gonna call you an idiot"

Dean sighed, frustrated with this conversation "That's...exactly what it is"

He wanted to believe that, that this thing with Castiel would be just a one-time thing, but god who was he kidding. He couldn't wait for work to be over so he could go back there.

Sam leaned back in his chair crossing his arms over his chest "You're an idiot"

Dean sighed and rolled his eyes. Sam was tapping his foot rapidly against the floor, the impatient sound echoing off the walls, nagging Dean to look at him. Dean gave up and did, facing Sam's intense glare and the clenching and unclenching of his jaw that made Dean slightly nervous, which he would never admit.

Dean opened his mouth in an attempt to ask what the hell Sam was suddenly so pissed about but almost choked when Sam flung his arms up in the air and nearly caused Dean to fall out of his chair.

"Are you serious right now? Come on Dean, you gotta see what's happening!"

"What are you talking about?!"

"Jo! I'm talking about Jo, you dumbass! Charlie might joke about it and I've never said anything before, but dammit Dean, she is not good for you!"

Dean's eyes were wide as he stared at his best friend. It's not like he didn't know that, he just, always assumed that it was probably just him...and well, Charlie but he summed that up to her strong dislike.

"Especially now that I've seen you this happy with someone else...I know for a fact now."

"Sam-"

"Shut up and let me finish ranting"

Dean's mouth shut.

"Look, I get it, there's a lot to think about, but, think about this too. You were happy this morning, you came in here smiling like a dumbass and you didn't care who saw you. Last night, you were happy, Saturday you got drunk and sang every Taylor Swift song that came on. Dean, that's the happiest you've been in three days than you have been in years"

Dean could only stare at Sam incredulously. His bluntness was like a slap to the face that he never realized he needed. "Charlie would be proud"

"Damn right she would and she'd probably slap you in the face"

Dean laughed a little at the thought and rubbed his eyes, suddenly he felt extremely tired and the day's work hadn't even started yet. "You're right Sam; I know you're right but-"

"All I'm saying" Sam started, leaning over the table to place a comforting hand on Dean's shoulder, meeting his gaze "Do what makes you happy and you won't have any problem with us, okay?"

Dean couldn't help smiling, playfully brushing Sam's hand off his shoulder "Yeah yeah, now get back to work before I fire you"

Sam straightened up and laughed, loudly, stuffing his hands in his pockets as he headed for the door "Ha, you can't threaten me with that; I'm your best friend!"

He flung open the door the same way he had when he came in and yelled "Ya hear that everybody, the boss is my best friend! I'm golden!"