Work Header

A Date for The Holidays

Chapter Text

“Cas, I need you to approve the budget for the Christmas party,” Charlie called from her desk outside of Castiel’s office at Novak Industries.

He looked up from his oversized cherrywood desk and stared at the open doorway as if it held all the answers. “Me? Why would I approve that?” he asked.

He waited for Charlie to respond, but when the reply didn’t come he sighed and picked up his phone, dialing one to get connected to Charlie’s desk.

“It’s been almost a year Cas. You’ve got to get used to having an assistant,” she chided. Charlie was Castiel’s oldest friend at Novak Industries, and when he got promoted to Chief Financial Officer, he got his choice of assistant. It had been a no-brainer for him. Charlie was smart, quick with numbers, and always by his side.

“I know, it just feels lazy to ask you to do things I’m capable of,” Cas pleaded into the receiver.

“Fine. Pay me to write fan fiction. I don’t care,” Charlie ribbed. “I need that budget today though. If I don’t get this cater booked we won’t have food, but more importantly, we won’t have booze. And if there is no booze, there is no fun. Do you want to be responsible for taking the fun out of Christmas, Cas?”

“No. Of course not.” Cas sighed, leaning his head back against his plush leather chair. The back came up about six inches higher than his head, and it made for a cozy resting place. His chair was the only part of his office he enjoyed. Though, he wasn’t too upset about the private bathroom.

“I ask again, why am I the one signing off on this? Shouldn’t Zachariah be handling this?” Cas pulled the handset away from his face to stare at it when he heard a click. It sounded as if Charlie hung up on him. It wouldn’t be the first time she disconnected their call out of frustration. Sometimes Cas had a passing thought of talking to her about showing him more respect in the office, but quickly shook the idea away. She could be rumbustious, but she was amazing at her job. Probably better suited for his position that just that of an assistant. She was brilliant and spunky, but because she hadn’t finished college, it was harder for her to move up the ranks in a place like Novak Ind.

“Zachariah is a tool, and if he saw the budget he would cut all the fun stuff. CFO approval means we get lobster and Cristal,” Charlie said, poking her fiery redhead through his open office door.

“What?” Cas squeaked.

“Kidding, Cas. Calm down. I mean you and I are getting Cristal, but your peasants are getting a very fine mediocre wine and middle shelf liquor.” Charlie strode across the soft carpet, the wide legs of her red jumpsuit bellowing around her. The light from the floor to ceiling window directly behind Cas shone through her short curls, making her look like her hair was shining.

“Don’t call them peasants, Charlie. We would have nothing without them.”

“I know, that’s why were are giving them the party of the century.”

Charlie plopped down in the seat directly across from Cas, pushing a stack of paper across his obsessively tidy desk. “Just look it over real quick. I checked last year’s budget and it’s nothing more than we spent then. I skipped Zachariah because Mr. Novak wanted me to plan this party personally.”

“You know I hate when you call me that,” Cas sighed, reaching forward to pull the papers closer to him.

“I do. But you also know I hate ol’ Zachy boy and he’s a Scrooge McDuck. He was already talking budget cuts the day you got promoted before you saved me from the carnage that is the seventh floor.” Charlie leaned back in her chair, dramatically crossing her legs.

Cas looked up, giving his friend a long-suffering look. “You have risen from the ash to become the Phoenix you were always destined to be.”

“Damn right I have. Now just sign the paper.”

Not bothering to look at the cost of the annual holiday party, Cas signed his name quickly and pushed the paper back across his never-ending desk. He often compared the monstrosity to a queen-sized bed.

“What’s with the jumpsuit?” Charlie was always colorful in her attire, but a fire engine red jumpsuit was a little loud, even for her.

“Oh.” she looked down at herself, smoothing away an imaginary wrinkle. “I just thought I would try something new. I, uh, have a date tonight. It’s too much, isn’t it? I feel ridiculous.”

“No. I think you look lovely. Just a little, uh, different than what you usually wear. But she’s going to think you’re gorgeous.”

“If only you were that smooth with strangers, you’d have a date other than a holiday party budget this weekend, too.” Charlie bounced up from her chair and out of the office before Cas could think of a reply.

It wasn’t as if Cas didn’t want a date for the weekend, especially the week before Thanksgiving at his mother’s. He would love to have a partner there to help him field the awkward conversations that were bound to happen again, just as they did every year. Where’s your date Castiel? Have you even been on one date since last year? All those years of prep school and you can’t talk to a man? How will you run this company without a man by your side?

Naomi Novak never batted an eye when Castiel came out to her when he was sixteen. Her solution to Cas being gay was adoption. She was a cutthroat bitch with exceedingly high expectations for her four sons, but Cas never doubted her love. She inherited Novak Industries from her father when she was a young new mother. Her husband Chuck was never around, and she always said her children were her saving grace. Cas believed that because when she walked in the door, she left the business behind. There were many nights she worked late, or weekends she wouldn’t be home, but those were rare. By 7pm she went from Mrs. Novak, CEO to mom.

His older brothers didn’t get the attention Cas got because by the time he came along Naomi was settled into a routine. Lou was the oldest, and bitter. Their mother made all the mistakes with him and wasn’t able to give him the time she gave Castiel. There was always tension between them, but it had ramped up since Cas’ promotion.

Lou was the first and only sibling to be given his executive position at Novak Ind. When that didn’t work out, and Naomi had to demote him, she vowed to make her children rise through the ranks. Michael was six years younger than Lou, and the acting CEO since their mother’s retirement at the beginning of the year. Gabriel ran the technology department, and Cas ran the financial side.

It wasn’t as though Lou had a low-level job, or was making a meager wage. He was still in the one percent and played an important role in the company. But he felt entitled to CEO, which ensured that the upcoming holidays were going to be full of tension, wine, and drama.

For reasons unbeknownst to him, Castiel was dreading the holidays with his family more than usual. It would stand to reason his anxiety was coming from his new position in the company. When he was middle management in the financial department, it was easy to show his face at the holiday party and leave before the conversation pushed past casual small talk.

      Thinking back to Charlie’s quip enforced that having someone to tend to or another person that needed to meet his date could be a good distraction at both the company party and dinner with his family. But he was inept when it came to dating. He was shy and awkward, with a heavy case of ugly duckling syndrome. He knew he wasn’t a bad looking man, but years of teasing and berating from his brothers had him wholly convinced he was a weirdo that couldn’t date.

Charlie had suggested earlier in the week that Castiel call an escort service and hire a date for both Thanksgiving and Christmas, and huffed when Cas balked at the idea. He may be an awkward shrew, but he wasn’t stooping so low as hiring a prostitute. Which lead to a long lecture from Charlie about the indignities sex workers face on a daily basis, and they didn’t need Castiel looking down their nose at them.

She came back twenty minutes later to first apologize and then explain that an escort is not a prostitute. Cas wasn’t blind to his privilege, liked to believe he was not the type to judge a person by what they did to make a living. Companionship was important, and oftentimes hard to come by, so Cas didn’t begrudge anyone choosing to sell their company. It just wasn’t a service he could see himself using.

But as the days drew closer to the impending Thanksgiving day meal, Cas started to rethink his stance on escorts. It had been years since he had been on a proper date with anyone, and just over a full year since the one time he tried a one night stand. Perhaps going on a date with an escort would take the pressure off being likable. His main drawback to inviting a professional to dinner as his date would be lying to his family. He wasn’t good at being dishonest, and he was sure he would slip up and embarrass himself. But he decided to give it more consideration for the holiday party. At home, his family knew he was awkward and shy, but schmoozing with an entire company was enough to make him want to call and book the appointment on the spot.

He considered for a moment. The event was two weeks before Christmas, and probably a busy time for the industry. If he wanted a good, charming, date he should move quickly.

It took Castiel two hours and Charlie asking if he needed anything else as she slipped on her black peacoat before he came clean with his desires.

“Um, yes. Just one more thing. Can I—I mean do you have the number for that escort service you mentioned?” Cas’ face flushed with embarrassment as he looked down at the stack of papers in front of him.

“O-M-G, Cas are you going to do it? Eeep, this is great. My friend Dorothy always uses this company, Succubus. She loves it. They are the best in the city. Super high class and––”

“Charlie, have you forgotten that I have no interest in women?” Cas asked.

“What? Why would you think that?” Charlie stopped buttoning her coat to stare at her boss.

“Well, a Succubus is a female demon that––”

“Oh. No! No it’s not just female escorts. Though I can see why you would think that. But no they started out as a female only business, but have recently expanded to include men. They even have a worker who is Agender. Crowley is really inclusive in his business.”

Cas stared at Charlie, wondering why she knew so much about what was essentially a legal form of prostitution. She made it sound like a high-class business. Cas mentally scolded himself for such judgmental thoughts. He had no idea how the business worked, and for all he knew it was a high-class business.

“Wipe that dirty diaper look from your face, Cas. It’s not like you’re thinking. It’s a nice place. And it’s not about sex with them. I mean, sex is involved I think, but this place is legit. They are about companionship. People with money find it hard to date casually. Your guy won’t come cheap, but he’ll be professional and fit right in with the esteemed Novak clan.”

Cas rested his elbows on his desk and dropped his head into his hands. This conversation was humiliating, and all he wanted was to get the website, get drunk, book the damn date, and forget this conversation ever happened. Maybe if he kept Charlie busy from the moment she walked in the door Monday, she will forget about it, and not probe him for details.

“Fine. Give me the details,” Cas mumbled into his hands.

“I can’t hear you, but I’m assuming you said, ‘thanks Charlie you really are the best. I owe you one.’ To which I would respond, ‘yes you do owe me one. I’ll add this to the ever-growing pile of ones you owe me.’”

Cas didn’t look up, but he could hear Charlie’s fingertips rapidly dancing across her screen. The ping of his phone confirmed that Charlie just texted him the website. Pulling himself from his quiet tantrum, Cas slowly raised his head to thank Charlie and assure that she was due one, as she said , for helping him book a fake date, because he was pathetic enough to not be capable of finding his own.

Several hours passed before Cas left the office, though the last half hour was spent looking for a way to incorporate pumpkin into a cocktail. Just because he was a wealthy well-respected man didn’t mean he wasn’t also a basic bitch at times. All the flavors were transitioning from pumpkin to peppermint and he hadn’t had his fill. He simply wanted to taste the flavor of the season, it wasn’t at all because he was avoiding the Succubus website.

After he was home and in his coziest sleep pants, Cas polished off his third pumpkin spice martini, staring at a blinking cursor of the incognito tab. Just a few letters and a quick tap of enter and he would be staring down the face of some of the best escorts in the industry. At least that’s what the thumbnail said in the message Charlie had sent him.  

Drawing in a deep breath, Cas quickly typed the address in and smashed the enter key. He wasn’t sure why he was so nervous, it wasn’t like looking at the website was a commitment. Cas almost laughed at himself when the page loaded to be a plain but elegant introduction page. It was black with red font. There was a simple menu icon and a slideshow of photos showing men and women out having a good time. A couple getting into a limo, two men laughing outside of a theater, a black and white photo of an elderly couple dancing.

Cas read over the about section quickly and moved on to the page called Our Talent. There he found several photos lined up similar to a yearbook page. Men and women in photos that looked as if they were professionally done. Everyone was beautiful. It seemed impossible to pick between them, each one was uniquely attractive.

After a little fiddling around, Cas was able to filter out the women, leaving seven men. They were handsome, and as he clicked through their bios, he learned they all were intelligent as well. Each biography was written with care and poise, but none of the men stood out the Castiel. They all seemed on equal footing in the looks department, but none of the hobbies or interest were things he wanted to spend a whole night talking about. He wondered if they had a random button and it selected a candidate for you.

Succubus let you browsed the Talent , as they called it, but to book a date, you had to call and schedule with the office. Cas’ eyes flicked up to the top of his screen. Fifteen minutes, he had one-quarter of an hour to decide if he wanted to go through with it.

He had a million thoughts, and just as many questions. Should he schedule someone for Thanksgiving and lie to his family? Would sitting through dinner with a pretend date be easier than sitting to the right of his mother—perched at the head of the table—listening to her preach about the importance of starting a family? Should they meet before going to his mother’s so they could learn a few basic things about each other?

Nine minutes left. Cas reached for his cell phone. He liked the idea of having a pre-date meeting with his date. It eased his nerves a little that he would at least look like he’d met the guy before showing up on his mother’s doorstep.

The phone rang twice before a slow, sultry voice said, “Succubus Escort Service, this is Meg, how can I help you tonight?”

“Ah, hello, Meg. I—um—I want to, I guess, book a date or, uh, schedule a date. I’m not sure how you say it.” Cas brought his palm to his forehead and scrunched up his face. He felt the tips of his ears burn at his own stupidity.

“I can help you with that, sugar. Have you used us before?” Meg asked.

“Uh, no. First time,” Cas responded.

“Do you know who you want to schedule a session with?” Meg could be heard tapping away at her keyboard on Castiel’s end of the call.

“I don’t think I have a preference other than he should be male, is that a problem?” He couldn’t imagine it would be.

“Not at all. Just give me the dates you are looking for and I’ll tell you who I got open that day,” Meg said.

“Okay, well I am hoping to find a date for Thanksgiving. I know it’s short notice, but I would also like to meet him before the day of, to hash out details.” Cas felt the childish urge to cross his finger they had an opening so close to the holiday.

“Okay, looks like you’re in luck. I have a new guy available. He isn’t on the site yet, but he has an opening on his calendar. Just because he’s new doesn’t mean he’s going to be a rube. Crowley only hires the best.” Meg sounded almost defensive.

“That sounds perfect. I’ll take him,” Cas said.

“Okay, so he’s got tomorrow as his only opening. You just need him on Thursday? You’re not staying over with the family?” she asked.

Cas thought for a moment. Naomi liked to host Thanksgiving at her country home. The house he spent his summer in when he was back from prep school. He usually did spend the night, but since Naomi wouldn’t insist on them sleeping in different rooms, it could get awkward. Though he supposed the guy might have had many paid overnights.

“No. Tomorrow and Thursday will do. I will also need him on December 18th, can you check if that is open?” He felt relieved at the idea of having backup to help him deflect the questions of his family.

“Yup, he’s open. I got you in for all three dates. I just need your email address to get you some forms to fill out.”

Cas rattled off his email address and answered all of Megs questions. It was easier for him to get a job as CFO than it was to answer the questions on the forms Meg emailed him. One thing he was certain of, Crowley vetted his clients well.

All the forms were submitted, the intrusive questions answered, and payment processed before Cas got the name of his date (he wasn’t going to say talent) . Dean Smith. Meg sent him the photos and bio that were getting added to the website. The man was beautiful, rugged in an eloquent way. He looked as though he could grow a two-day beard and take you camping in the desert. Or give himself a clean shave and take you to an art gala. He was thankful he hadn’t been able to choose. Dean sounded perfect.

Cas mixed himself one last martini and pulled out a legal notepad. He wanted to make a list of everything Dean would need to know. He planned on telling his mother they had been seeing each other for a month. He had to make it believable that Dean wasn’t after him for his money. His family knew he didn’t flaunt his wealth and considered the merit of telling his mother that Dean didn’t know about his fortune.

He wasn’t sure how this had spun so completely out of control. Less than twelve hours he wasn’t even considering hiring someone to be his date for a holiday party, now he was preparing to lie to his whole family to save a little embarrassment. If fiction had taught him anything, this was bound to fail.