It was the middle of the afternoon, the blazing sun peeking from behind a rogue cloud high in the sky above the Winchester tower. The tower housed a thousand or so employees, from janitors to the very king himself: Dean Winchester. Dean sat upon his throne, slumped over in an unkingly way in order to lean forwards and click his spine out from its usual ‘stick-up-his-ass’ posture. Though, to Dean’s credit, the stick was only there to keep him from keeling over from a mixture of severe boredom and a dire case of the cumbersome inbox of death, practically overflowing onto his desk. Perhaps it would’ve been wise to go fully online like his secretary had suggested, his secretary being the one with the more natural serious streak in his mane of chestnut hair. Maybe Sam should take over his position as CEO, perhaps /then/ Dean would be able to indulge a little in the luxury that was time to himself, for himself. The thought of a cold beer, dripping with condensation in his hand, hot sand between his toes, snaps of the Grand Canyon on his desk taken by him and not some photographer unknown to him… those thoughts brought the briefest smile to his lips before the opening of his office door snapped him back to reality. Sam gently placed a relatively small stack of papers to the clear corner of Dean’s desk and gave him a small yet worried smile. Dean just shook his head and let his head hang a little, an action that Sam knew meant for him to back off and leave Dean to his misery of a heavy work day.
Dean knew he could just give himself the day off, like other CEOs; he could take the day off and go golfing or fishing from his boat that sat gathering algae in the marina. But that was what Dean always did on his days off and he’d be damned if he let his own fun get boring to him. Perhaps he could forget he was a CEO, don a baseball cap, a thick and well-worn plaid shirt and broken-in jeans that hung low on his hips. Maybe he could trawl a bar or two, get a little too drunk and take some random bar chick to a skeezy motel (okay, maybe he wouldn’t go that far) and fuck her brains out - give her a good time.
He sighed. He was still CEO, with the fate of a thousand or so people’s livelihoods on the line, he still would have this pile of crap to contend with, and he still had no time for Dean, nor did he have time for poor Little Dean.
Eyeing the door, now firmly closed behind Sam, his mind began to pay a little more attention to Little Dean; thoughts of nimble fingers dragging his zip down, easing his slacks down to his knees along with his boxer briefs. Nails tracing the upward curve of his cock. Lips dancing teasingly on the underside.
He hadn’t meant to yell, he hadn’t meant to say a single word; but there he was, having launched himself to his feet his hands wide across the desk and his eyes glaring daggers at his secretary.
“I,” He took a breath. “Am takin’ the day off. I want this pile at least halved when I come back. I want no calls. If anyone asks where I am, tell 'em I died, I went to Cancun. Tell 'em I’m on a fishin’ trip with Trump for all I care.”
With that, he gathered his briefcase together, loosened his tie and left his wood panelled office walls and made a break for freedom.
He ended up in a bar, one just out of town called 13 Kings. Unfortunately, as far as eligible bachelorettes went, things were slim pickings. One was a wary looking bartender with unnervingly large eyes that protruded a little, another was a geriatric woman that insisted she was 25 when she was probably closer to 52. It was in those times of romantic struggle that Dean allowed his eyes to linger on others, male others. There was a guy that fancied himself something of a cowboy type, rolled up sleeves on his button down shirt that tucked into his levis held up by an old leather belt with a confederate flag buckle. Yeesh, he’d have to get him out of that ensemble before he could appreciate the pretty face that smouldered beneath the scruffy blonde bangs.
Dean sighed and glanced at his phone. Five missed calls, 19 voicemails, 27 texts and an email notification. The good thing about being a notorious technophobic business man, it meant that people that had to email would email Sam - not him. This meant that the email notification was a little more significant to a man like him, so he opened it. It didn’t take long for him to realize that his curiosity was to be disappointed. Spam, the type of spam that came from websites that you would sign up to for just a little nose around, rose its ugly head as a reminder of that one time he had explored 'Grindr’. Dean looked side to side, an embarrassed blush sweeping across his nose. Taking his whiskey from the bar, he meandered over to an empty table for one over in a corner. Tapping on the header of the email, he was sent to his profile page that he’d made… it had to have been at least 3 years ago. He’d set his picture to a close-up of a what could be described as a cheeky poke of his tongue between his teeth and lips. Guys liked to focus on his mouth.
He looked up from his phone, back over Mr. Cowboy who was now chatting quietly with a guy that Dean would also class as a perfect depiction of Mr. Cowboy 2. The two men left the bar as he watched and Little Dean reminded Big Dean that a man had needs, and the needs needed to be taken care of pretty soon.
Dean looked back down at the Grindr profile, /his/ grindr profile and gave yet another frankly pathetic sigh. He threw the whiskey to the back of his throat, set it down with a tip, and headed out of there and ducked into the gleaming black Chevy in the parking lot. He wasn’t drunk enough to do this in a public place.
Once home, the oxfords were toed off and left by the door, the stuffy suit was discarded in the laundry basket for his housekeeper to take care of whenever it was she decided to come and do her job. He slumped on his plush corner couch, the cool of the rich leather greeting his hot skin with open arms. Dean grabbed his phone from the coffee table and found himself looking at his cringe-worthy photo again, maybe a more recent photo would help. Scrolling through his phone, he found a shot he’d taken from a photoshoot that he’d done for an entrepreneur magazine where they’d decided that the hunting supplies and sporting goods CEO guy should definitely be moping around in a fountain. He’d never understand the media. But, one good thing that had come of it had been one of the photos they’d decided not to use: gleaming tiles in the background, water trickling over his face, hanging precariously from his eyelashes, and draping almost obscenely over his bubblegum pink lips. That was the one, that was the photo he’d use for his profile. He uploaded it, cropped it to only show what he wanted to show and, with a moment of hesitation, he posted his profile once more. DWimpala67. Single. Looking for chats, hook ups and friendship.
