Dean and Charlie always made time to hang out at least once a week, even if it just meant walking home from work together.
Between Dean's job at Bobby's garage, his part-time gig bartending at a local bar, and his college courses, he was stretched pretty thin. Charlie was in a similar situation, juggling two jobs, one as the head of the IT department at some big name enterprise and another at a bookstore, and a new relationship with her girlfriend Dorothy.
When Dean had decided to finally get his degree, having gotten his GED a few years prior, he had met Charlie at the bookstore where he had been looking for a copy of the textbook Sam had accidentally ruined. She had been working behind the desk, tapping away on her laptop while blasting some kind of pop music, when Dean had gone to the front to buy the overpriced textbook.
They had both winced at the exorbitant price, Dean cracking a half-assed joke that had fallen flat as he pulled out his wallet. She had given a courtesy laugh before brightening with a genuine smile and punching a cash register keys that immediately brought the price down by at least twenty percent.
Beaming, she had informed him, in a conspiratorial whisper, that she had used her employee discount, much to both Dean's delight and astonishment. They had been friends ever since, bonding over their shared love of all things nerdy and the struggles of being the only LGBTQ+ members of their families.
Now, two years later, they were as close as siblings, Charlie the sister that Dean had never wanted and Dean the sometimes overprotective brother Charlie had never had. Between their busy schedules, it was increasingly difficult to hang out, even just for an afternoon.
Not wanting to give up on their hang out day altogether, they simply improvised. Which is why there Dean was, walking Charlie from her office building to the bookstore a dozen blocks away.
"Oh my god, did you see the new trailer?" Charlie asked after taking a sip of her coffee, some kind of caramel latte frappuccino thing with a huge dollop of whipped cream on top.
"Yeah. Looks pretty good," Dean answered, weaving around a woman pushing a three seated stroller. She murmured a grateful thank you as she passed.
"Pretty good? Pretty good?!" Charlie gasped, thoroughly scandalized. It showed on her face as she gaped at him, her jaw slack as she pushed her glasses further up her nose.
She gestured aimlessly with her free hand, nearly smacking a passerby in the face in her unchecked enthusiasm. Yanking her arm back, she continued on, "It's Wonder Woman 2, Dean! It's gonna kick ass!"
"I know, kiddo," Dean chuckled, holding up his hand in a placating gesture. Taking a sip of his own coffee, black with just a little bit of sugar, he rolled his eyes at Charlie's outburst.
Both of them were devout comic book fans, Dean preferring DC while Charlie was a Marvel girl through and through. They had never missed a superhero movie and they didn't plan to, always reserving tickets for the premiere. Charlie's hacking skills, while beyond illegal, were extremely helpful.
"So..." she sing-songed, batting her eyes at him innocently. But from the tone of her voice, Dean knew that she was anything but. "Have you thought about what I said about my boss?"
"Ugh, Charlie. Not this again," Dean groaned, hanging his head as they crossed the street. Shaking his head, he firmly announced, "For the last time, I don't wanna go out with your boss."
"But why not?" Charlie whined in return, jutting her bottom lip out in an exaggerated pout. It was the same pout that was just as effective as Sam's ridiculous puppy dog eyes, maybe even more so. "You've never even met him!"
"Yeah, that's why I don't wanna go out with him, Charlie," Dean sighed, pinching the bridge of his nose. For the past few months, Charlie had been trying to convince Dean to go on a date with her boss, claiming that he was perfect for Dean.
Apparently, the guy's name was Castiel which was the most pretentious thing he had ever heard and he had once gone out with a dude named Brady. And according to Charlie, he was downright dreamy.
Dean had to admit that she was probably right about that. If even she thought a dude was dreamy, he must be a modern day Marlon Brando.
Charlie had talked his ear off about how handsome and considerate her boss was, detailing all of his contributions to various charities from the local animal shelter to Meals on Wheels. Not to mention how entrepreneurial he was, opening the bookstore with his brother a few years back when he had moved to Lawrence from Illinois.
She had even sung praises about how smart he was. One day she had spent fifteen minutes detailing her boss' time at Columbia, listing his degrees, and mentioning a few books he had written.
But as amazing as this Castiel guy sounded, Charlie making it sound like the dude shot rainbows out his ass that she assured him was objectively perfect, Dean had learned his lesson about letting friends set him up with people.
The last time he had gone on a blind date it was with some guy his friend Benny had set him up with. It was a disaster.
The guy's name was Fergus but he went by Crowley, probably because his parents had cursed him with a ridiculous name like Fergus. He had spent the entire date, dinner at some overpriced French restaurant where Dean had stuck out like a sore thumb in his flannel shirt and faded jeans, talking about himself and making lewd innuendos about the size of his dick.
That had been the end of Dean going on blind dates. Besides, he may or may not have had his eye on someone.
There was a regular at the bar that had captivated Dean since the first time he had seen him and he had been working up the nerve to ask him out for weeks. And he wasn't going to give up on the cute nerd he'd admittedly been pining for just because Charlie had a hot boss.
The first time Blue Eyes, as Dean referred to the man in his head, had come into the bar where Dean worked, he had looked like complete and utter shit. His black hair was messy, his clothes were disheveled, and he was sopping wet.
It had looked as though he hadn't gotten the memo about the storm that had drenched the city and filled the sky with strikes of pale lightning. Looking exhausted, dark circles under his beautiful blue eyes, thus the nickname Dean had given him, he had taken a seat at the bar. With a resigned sigh, he had ordered some whiskey, a bacon cheeseburger, and a plate of loaded nachos.
Blue Eyes had offered to share his nachos with Dean when the sound of his empty stomach rumbling had filled the air. Dean had been eternally grateful, giving Blue Eyes a beer on the house.
They had spent almost two hours talking, bantering lightheartedly as Dean made drinks for the others at the bar. And yes, Dean might have been a teeny tiny bit more dramatic as he used the cocktail shaker to make cosmopolitans and daiquiris, flexing more than necessary to show off his biceps in his tight black t-shirt.
He had been pretty disappointed when Blue Eyes had finally left the bar, though he had left behind a tip worth more than his meal. His disappointment didn't last long. Blue Eyes showed up again the next night.
He had ordered one of the fancy cocktails that Jo had come up with to set the Roadhouse apart from other bars in the area and it had somehow morphed into a little game between them. Every time Blue Eyes came in, Dean would surprise him with different cocktails, never telling him what the drink was called until he had tried it.
Dean would never forget the look on Blue Eyes' face when he told him that he was drinking an angel's tit. The poor guy's entire face had turned bright red as he choked on the mix of cherry liqueur, half-and-half, and white creme de cacao.
But for all of Dean's flirting through sexually named cocktails, he had yet to work up enough nerve to actually ask him out.
"Anyway..." Charlie drawled, whipping some whipped cream off the tip of her nose. "You doin' anything tonight? It's been way too long since we've actually hung out."
"I work at the bar tonight but I'm off all this weekend for once. No classes, no work," Dean replied, a wide smile stretching across his face at the thought. He couldn't remember the last time he had been able to sleep in past nine o'clock. He couldn't wait. "We'll have a slumber party. You can braid Sam's hair."
"Ugh, I haven't seen Sam in months. He's off being a hotshot lawyer," Charlie lamented, throwing her head back. Looking over at Dean, she narrowed her eyes and asked, "He still growing his hair out? It's gotta be past his ass by now."
"Oh, yeah," Dean agreed, nodding a couple times. "Pretty soon he'll be tripping over it."
Charlie laughed and started rambling on about how if Sam was Rapunzel then Dean must be a Disney princess, too. He nodded along as she debated whether or not he would be Moana, a free spirit who loved travel, or Belle, beauty and brains all rolled into one, until he was distracted by a store window.
It was an independently owned clothing store, an upscale boutique called Sew It Seams that catered to women especially. And by that, he meant that a large portion of their stock was lingerie.
They sold everything under the sun, from frilly lace panties to dominatrix-esque leather bustier, in every color imaginable. From what he had heard from customers at the bar, they actually had plus sized articles of clothing made for women who didn't just have hourglass figures or bigger thighs.
In their store window, there were a few torso mannequins, headless, armless, and legless as they advertised different types of lingerie. It was an unexpected sight on the street full of more family friendly shops which is probably why it caught Dean's eye.
Well, that and the fact that he had always been a bit fascinated by lingerie. Ever since he was nineteen and he'd tried on Rhonda Hurley's satiny pink panties.
Call it a kink, call it a fetish, call it a run-of-the-mill preference. Whatever the hell it was, he had it.
The only person he had ever dared tell was Charlie. Which is why he was glad she was with him.
As he admired a pair of bright red panties and a matching sheer babydoll, he reached over to nudge her hand. He groped under blindly under he finally made contact, muttering, "Hey, Charlie. Wouldn't I look sexy in that?"
He turned around with a cocky grin to see her reaction, expecting an eye roll or a punch on the shoulder. It was fair to say he was expecting to see Charlie standing beside him, not Blue Eyes himself.
The man blinked at him, his angelic blue eyes wide as Dean's face filled with heat. He quickly glanced around in search of Charlie, finding her about a yard away with a hand clamped over her mouth as she shook with poorly concealed laughter.
"Uh, I—" Dean squeaked, his voice high pitched, but he didn't get to finish his pathetic excuse because Blue Eyes cleared his throat and squinted at the store window.
"I suppose," he murmured thoughtfully, nodding to himself. But, turning to Dean, he pointed a finger at the store window and claimed, "But I believe that color would be better. It complements your skin tone."
His jaw nearly dropping, Dean inclined his head to look at the other mannequin that was adorned in the same style of lingerie. The babydoll and panties were pale pink, dainty and feminine and oh so intriguing.
"Uh, yeah... I guess you're right," he managed to stammer out scratching the back of his neck as he was overwhelmed with how much he suddenly wanted the lingerie set. Face still warm, he dropped his eyes to the sidewalk, staring at a spot of old chewing gum.
"So, uh..." Charlie's voice sounded, making Dean tense. He knew that tone. That was her 'I'm-about-to-meddle' tone. She confirmed it a second later when she announced, "I guess this is as good a time as any for introductions."
Dean whipped his head up so fast he was surprised he didn't break his own neck, narrowing his eyes at his best friend. She just smirked back at him before she spoke. "Dean, this is my boss Castiel Novak. Castiel, this is my best friend, Dean Winchester."
Dean's jaw immediately dropped as he turned to Blue Eyes, or rather Castiel. Charlie's fucking boss. The guy he'd been pining over and the guy she'd been trying to set him up with apparently one and the same.
Blu—Castiel offered a rather shy looking smile, drawing Dean's attention to the chapped pink of the other man's lips. He managed to tear his eyes away before things got even more awkward, returning Castiel's smile with one of his own.
Their moment was interrupted by Charlie who chimed in, "Y'know, as good as Dean would look in those panties, I bet they'd look even better on your bedroom floor, boss."
"Charlie!" Dean squawked indignantly, shooting a glare at his friend over Castiel's shoulder. "Stop hitting on him for me!"
"Well, someone has to, Dean," Charlie said simply as though it made complete sense. She rifled around in her purse for a moment, handing Dean her hoity-toity coffee as she did.
A moment later, she pulled out a slip of paper and a pen. After writing something on the paper, she handed it to Castiel, explaining, "That's Dean's number. He has the whole weekend off so you can take him on a date tomorrow."
She turned to Dean with a bright smile. "Well, I'm gonna get to work. You crazy kids stay here and talk about where you're going for your date—" she looked back at Castiel "—Dean loves pie. The diner on Fifth Street serves his favorite pecan pie. You should take him there."
Without another word, she spun on her heel and continued her walk to the bookstore, her ponytail swaying as she jogged across the street. Dean and Castiel were left to stare at Charlie's back before awkwardly glancing at each other.
"So..." Dean began, pursing his lips and shoving his hands in his pockets. He rocked back on his heels as he chanced a look up at Castiel. "Tomorrow night?"
"How about tonight?" Castiel countered with another smile, sounding adorably hopeful. After biting his lip, he elaborated, "I'll be at the Roadhouse tonight. Maybe we could split some nachos again? You could make me one of your dirty cocktails."
"Yeah, that sounds good," Dean responded, maybe a bit too eagerly. "How does a cock sucking cowboy sound?"
"Depends," Castiel said, nodding decisively. Smirking, looking much more confident, he inquired, "Is that the drink or you?"
Letting out a startled laugh, Dean answered, "Depends. How good are you gonna tip me?"
As Castiel laughed, the sound lighting him up from the inside, Dean acknowledged that he might have to change his stance on letting friends set him up. Then again, he hoped that he wouldn't ever need to be set up with anyone because Castiel seemed pretty damn perfect.