Chapter Text
Snow drifted past the floor-to-ceiling window of Castiel Novak’s office, each flake twisting lazily as it fell to the city below. The late afternoon light had begun to fade, casting long, gray shadows across the downtown skyline. Inside his office, the warmth of central heating did little to dispel the cold ache that had settled deep in his chest.
His fingers gripped the edge of his desk as he stared out at the quiet snowfall. He knew the world below was bustling—cars inching along the slushy roads, people bundled in layers of scarves and coats, hurrying to escape the cold. Yet from up here, ten stories above it all, everything seemed still.
His phone screen flickered with the soft glow of an email notification, and his eyes, tired and heavy with something nameless, dropped to the message he had read hours ago but still couldn’t bring himself to answer.
Can't wait to meet him, Cas! We’re all so excited. Mom’s already planning the menu, and you know how she gets.
A lie.
A simple, stupid lie he had told in passing to stop the endless questions about his love life. He hadn't expected it to spiral into this—his family now eagerly awaiting the arrival of a boyfriend who didn’t exist.
Castiel exhaled sharply, rubbing his fingertips over the bridge of his nose. It wasn’t as if he was incapable of dating. He had the means, the home, the career. He was a successful therapist, a man with a well-respected practice, a beautiful house he barely spent time in, and enough financial security that loneliness should have been the least of his concerns.
But it was.
It always was.
He had spent years convincing himself that work was enough, that he didn’t need what others craved—companionship, intimacy, love. But now, as he sat alone in his pristine office, with nothing but the dull hum of his computer and the distant chatter of the city below, he knew better.
Dragging himself back to his desk, he unlocked his computer and hesitated for only a moment before typing the words he had never imagined searching for.
Local escort services.
A flood of options filled the screen, but one in particular caught his attention.
Divine Touch.
The name was absurd, and yet, his fingers moved instinctively, clicking on the link before doubt could creep in. The website loaded with a sleek, minimalist design—black background, gold lettering, clean and elegant. The moment it fully rendered; a large disclaimer flashed across the screen:
All services are strictly companionship-based. Anything beyond this agreement is between consenting adults and not the responsibility of Divine Touch.
He skimmed the words, then read them again, slowly this time, because part of his obsessive nature demanded it.
Only companionship.
That was all he needed—someone to stand beside him, to hold his hand when necessary, to smile when his mother asked about their “relationship.” A few days of pretending, and then they would part ways. Simple. Logical.
So why did he feel like he was about to step off a ledge?
His pulse thrummed as he clicked past the warning and into the selection of available companions.
Faces filled his screen—dozens of men, all polished and poised, their smiles perfected for the camera. Some were too young, others too sculpted, their carefully curated photos exuding an air of artificial charm. Nothing about them felt real.
His scrolling slowed as he neared the bottom of the page, his eyes tired and ready to give up. And then—
Dean Winchester.
The name alone had weight to it, solid and familiar, even though Castiel had never heard it before. He clicked on the profile, his breath stalling as the page expanded.
Dean’s photo was different from the others.
He wasn’t posing in an overly extravagant setting or wearing an expensive tailored suit. No forced smirk, no overly edited perfection. He sat in a dimly lit lounge, the warm glow of an unseen fireplace casting soft shadows over his sharp features.
Dean looked comfortable. Effortlessly confident.
His short-cropped, honey-brown hair was slightly tousled, as if he’d run his fingers through it moments before the photo was taken. His jawline was dusted with scruff, just enough to make him look rugged rather than unkempt. His green eyes weren’t just striking—they looked into the camera with an intensity that felt tangible, like they could unravel someone with a single glance.
And then there was the way he was dressed.
A deep emerald silk button-up, sleeves rolled to his elbows, exposing strong forearms and lightly tanned skin. The fabric clung to him in a way that was neither intentional nor overly styled—it simply fit, draping over broad shoulders and an undeniably well-built frame. The top two buttons were undone, revealing just a hint of collarbone, a whisper of something intimate without being obvious.
Paired with the shirt, he wore dark jeans, well-fitted but relaxed, as if to balance the elegance of the silk. He leaned back against a low-backed chair, one arm draped lazily over the armrest, the other resting on his thigh. A silver ring glinted on his right hand, catching the light just enough to draw attention to his fingers—long, strong, the kind of hands that knew both precision and care.
Beneath the photo, a short bio accompanied his profile.
Dean Winchester, 30
Confident, charming, and discreet. I specialize in authentic companionship—whether that means an evening of easy conversation or playing the role of the perfect partner at family gatherings. I adapt to what you need. No pressure, no expectations. Just an unforgettable experience.
Castiel swallowed.
The words were simple, but there was something about them that felt like a promise.
Something about him that felt… safe.
His heart gave a strange little kick as he stared at the small button at the bottom of the profile.
Contact.
His fingers hovered over the trackpad.
One click, and everything would be set into motion.
A few days of pretending. A man he didn’t know stepping into the role of something that had never truly existed.
Castiel closed his eyes for a long moment.
Then, with a slow exhale, he clicked the button.
The screen refreshed, and Castiel’s breath hitched as Dean Winchester’s full profile loaded before him.
The first thing that caught his eye—before he could even process the rest—was the price.
His stomach twisted.
- Hourly Rate: $500
- Overnight (8 hours): $3,500
- Weekend Experience (48 hours): $10,000
- Extended Exclusive Arrangement: Inquire for pricing
Castiel sat back in his chair, staring at the numbers.
That wasn’t just high—it was exclusive. This wasn’t some casual service for anyone looking to rent a warm body for the night. Dean was well sought out, a high-end escort for the elite, the kind of man whose clientele likely included politicians, CEOs, celebrities.
People who could afford to pay that much for someone like him.
And yet, the moment Castiel considered closing the page, his eyes drifted lower, to the rest of Dean’s profile.
Dean Winchester
Age: 30
Height: 6’1”
Build: Athletic/Muscular
Eyes: Green
Hair: Light brown
About Me:
You deserve an experience, not just a date. Whether it’s a night of deep conversation over a bottle of bourbon, a weekend of playing the perfect partner, or simply some much-needed companionship, I offer authenticity in every interaction. I adapt to your needs—whether that means making you laugh, keeping things low-key, or turning heads when we walk into a room. My job isn’t just to be at your side but to make you feel like I should be there. No pretense. No pressure. Just a night (or weekend) that’s about you.
Confident, discreet, and a damn good listener. Let’s make some memories.
Languages: English, conversational French, basic Spanish
Hobbies & Interests: Classic cars, whiskey, classic rock, cooking (breakfast is my specialty), live music, road trips
Specialties:
- High-profile events
- Family functions (pretend boyfriend, fiancé, husband)
- Travel companion
- Intellectual conversation & social engagement
- Exclusive, tailored experiences
Castiel swallowed.
He hadn’t expected something so personal. Most of the other profiles he had skimmed were all business—clean-cut, impersonal, straight to the point.
Dean’s, though?
Dean had character.
It wasn’t just an ad—it was a man talking, laying out who he was, what he brought to the table. He wasn’t selling sex, he was selling experience. Charisma. Presence.
And Castiel—against his better judgment—was intrigued.
He exhaled and scrolled lower, drawn into the images next.
The first was a headshot—Dean in a fitted navy blazer over a black button-up, the top undone just enough to hint at something playful without being unprofessional. His hair was short but slightly tousled, the kind of deliberate messiness that spoke of confidence. His smile was easy, natural, his green eyes sharp yet warm.
Then came the casual shots.
Dean leaning against the hood of a sleek black ’67 Chevy Impala, arms crossed over his broad chest, jeans snug but not too tight. A leather jacket stretched over strong shoulders, giving him the undeniable air of someone who belonged in a bar, whiskey in hand, laughing with friends.
Another showed him in a dimly lit lounge, sipping a drink, gaze directed toward the camera with the kind of intensity that made Castiel's stomach twist.
And then—
Dean in a silk button-up the color of deep burgundy, the sheen of the fabric catching the light in just the right way to emphasize his form. The sleeves were pushed up to his elbows, exposing strong, lightly tanned forearms. He was seated, legs spread slightly apart, relaxed, with a knowing smirk that made Castiel’s breath hitch.
The last photo was… something else entirely.
Dean in nothing but a silk robe, loosely draped over his shoulders, exposing his toned chest and the sharp lines of his abdomen. It wasn’t vulgar—it was suggestive, tempting, an unspoken invitation that lingered just on the edge of indecency.
Castiel’s face felt hot.
Oh.
He let out a slow, measured breath, pushing a hand through his dark hair.
What the hell was he doing?
This was ridiculous. He was a man in his thirties, a successful professional—he shouldn’t be this affected by a few pictures. And yet, something about Dean—something beyond the perfect face, the effortless charm—pulled at him.
It was in his eyes.
No matter the setting—casual, playful, seductive—there was something deeper there. A quiet intelligence, a knowing look, like he was always reading the room, always adapting.
Castiel’s fingers hovered over the trackpad.
He should walk away.
This was impulsive, absurd, expensive. He could just—he could make an excuse, tell his family his boyfriend had gotten sick, endure the teasing and the pitying glances.
But then he imagined it.
Sitting at the dinner table, his mother’s hopeful eyes, his siblings whispering about how he was still alone. The same questions as always. Why don’t you date? Why are you so focused on work? Aren’t you lonely, Cas?
He wasn’t sure he could take another year of it.
His gaze dropped back to the screen, to the contact button at the bottom of the page.
His chest tightened as he clicked it.
A simple message box appeared.
Name: Castiel Novak
Preferred Contact Method: Email
Request Details:
He hesitated before typing.
Hello. My name is Castiel Novak. I am looking for companionship for a holiday gathering with my family. I require someone to play the role of my partner for approximately four days. If this is something you would be available for, please let me know your rates and availability. Discretion and professionalism are important to me. Thank you.
His heart pounded as he read it over.
Too formal? Too stiff? He nearly erased the entire thing.
But before doubt could sink its claws in any deeper—he hit Send.
A confirmation message appeared, simple and impersonal.
Castiel exhaled, sitting back in his chair.
It was done.
Now all he could do was wait.
And pray to whatever higher power existed that he hadn’t just made a very, very expensive mistake.
The email was sent.
The moment the screen refreshed with a confirmation, Castiel let out a breath he hadn’t realized he was holding. His fingers lingered over the trackpad, temptation whispering in his ear to close the page, to pretend this had never happened.
But it was too late now.
Leaning back in his chair, he rubbed his hands over his face, heart still thudding against his ribs. This was irrational. He had spent his entire life making calculated, thought-out decisions—never acting on impulse, never choosing the unknown when the familiar was right there.
And yet, here he was, paying—no, hiring—an escort to be his date for the holidays.
His eyes flicked toward his phone, almost expecting an immediate response. But of course, there was nothing.
What if he doesn’t answer?
The thought sent another wave of doubt curling through him.
Dean Winchester was clearly a high-end escort, well sought-after by clients who probably didn’t hesitate to pay his outrageous fees. He likely had no shortage of offers from people far more interesting, far more attractive than Castiel.
God, this is ridiculous.
Castiel dropped his head against the back of his chair, staring at the ceiling.
What if Dean read his message and laughed? What if he saw Castiel’s name and immediately rejected him? What if he thought Castiel was too stiff, too formal? Maybe he should have written something more… casual. Maybe his email had sounded too clinical—like he was drafting a business proposal instead of hiring someone to play his boyfriend.
His fingers tapped anxiously against his desk.
Three minutes had passed.
Had it only been three minutes?
He reached for his coffee mug, took a sip, and immediately regretted it. Cold. Disgusting. He set it down harder than necessary, pushing away from his desk. Maybe he should go home, forget about the whole thing. If Dean replied, then fine—but if not, he could call his brother tomorrow and make up an excuse.
Five minutes.
Six.
Seven.
His chest tightened. What were you expecting, a response in thirty seconds? He was being ridiculous.
Just as he was about to shut his laptop, the “new message” notification pinged.
His pulse jumped.
He reached for it quickly, fingers fumbling slightly as he opened his inbox.
New Message from Dean Winchester
Castiel swallowed hard and clicked.
Subject: Now, that’s a name I don’t see every day
Hey, Castiel.
Gotta say, I don’t think I’ve ever met a Castiel before—kind of rolls off the tongue, don’t you think? Unique. Strong. Not bad at all.
I read through your request, and I have to admit, it’s not my usual gig. Holiday weekends—I can already imagine the nosy relatives, the concerned parents, the side-eyes from distant cousins. Sounds like a hell of a show.
So, tell me, sweetheart—what exactly do you need from me? Just a hand to hold and a smile to sell the story, or are we talking the full ‘can’t keep our hands off each other’s couple experience? Gotta know how deep we’re playing this.
Also, before we set anything in stone, I like to meet my clients in person first. Call it a vibe check—makes things easier for both of us. Let’s grab a drink. You pick the place, and I’ll be there.
Looking forward to it.
—Dean
Sweetheart.
His lips parted slightly, an unfamiliar tightness curling in his chest. It wasn’t that he had never been called pet names before, but something about the casual, flirtatious ease in Dean’s tone caught him off guard.
The message was both playful and professional—a perfect balance between charm and business. Dean was clearly good at this. Too good.
Castiel hesitated before typing his reply.
Dean,
Thank you for your response. I understand and appreciate your need to meet beforehand. I would prefer something quiet, somewhere we can talk. If you are available, there’s a lounge downtown called Evergreen—it’s discreet and not overly crowded. Would tomorrow evening at 7 PM work for you?
As for my request, I need someone to convincingly play the role of my boyfriend. My family will expect interaction, but nothing excessive. Just… natural. I trust we can discuss further in person.
Let me know if this time and place works for you.
Best,
Castiel Novak
He stared at the message, fingers hovering over the Send button.
Too formal again? Too stiff?
But before he could overthink it, he pressed Send.
Now, all he could do was wait—again. And pray that he wasn’t making an even bigger mistake.
***
The low hum of conversation filled Evergreen, a quiet, upscale lounge tucked into the heart of downtown. Castiel had chosen the place for its atmosphere—dimly lit, intimate but not suffocating, elegant but not pretentious. The booths were lined with plush, dark leather, and the air smelled of aged whiskey and subtle vanilla from the burning candles scattered across tables.
His corner booth gave him the perfect vantage point—far enough from the bar to avoid unwanted attention, close enough to watch the door.
And right now, all he was doing was watching the door.
His nerves were a disaster.
He checked his watch for what had to be the tenth time.
6:52 PM.
Dean was supposed to arrive at seven.
Castiel exhaled through his nose, forcing his hands to stay flat on the table, resisting the urge to tap against his glass. His foot, however, bounced lightly against the floor, betraying his composed exterior.
This was a mistake.
The thought hit him with startling clarity.
You should have just told the truth. Made up an excuse. Anything but this.
He had no business being here, sitting in a dimly lit lounge waiting for a man he had hired to play the role of someone who didn’t exist. The very idea was absurd. He could still leave—pretend this never happened, send an apology email later.
But then he imagined his mother’s eager smile. His siblings' knowing glances. The inevitable Aren’t you lonely, Cas? whispered over holiday drinks.
His fingers curled against his knee.
No. This was necessary.
He raised a hand to signal the waitress, hoping a drink would steady him.
“Whiskey,” he said when she approached, his voice lower than usual. “Neat.”
She smiled. “Any preference?”
“Surprise me.”
The words left his mouth before he could analyze them, and for once, it felt good to let go of the control he always clung to so tightly.
She nodded and disappeared, leaving Castiel to check his watch—again.
6:56 PM.
The seconds stretched, slow and relentless.
And then—
The air shifted.
The door opened, and before Castiel even looked up, he felt him.
Dean Winchester.
He wasn’t sure how he knew—maybe it was the way the room seemed to shift around him, or the way the soft conversations at nearby tables seemed to quiet just slightly, unconsciously drawn to the man who had just walked in.
Castiel lifted his gaze, and for the first time, he saw him.
Dean was… overwhelming.
The photos had not done him justice.
The man who had just stepped into the lounge moved with the kind of effortless confidence that couldn’t be taught—like he owned the space the second he entered it. He was tall, broad-shouldered, built like someone who knew how to throw a punch and make it count.
His dark red button-up clung just right, the sleeves rolled up to his elbows, exposing strong forearms, veins prominent. The top two buttons were undone, a hint of collarbone visible, teasing at the edges of something that shouldn’t have been distracting, but somehow was.
Dean’s green eyes flicked over the lounge, scanning, assessing, and then—locking onto him.
A slow, knowing smirk pulled at his lips.
And just like that, Castiel’s stomach tightened.
He forced himself to sit straighter, gripping his glass as Dean strode toward him with an easy, rolling confidence that only he could pull off.
By the time he reached the table, Castiel was convinced the entire room was watching him.
“Castiel,” Dean greeted, his voice rich, smooth, edged with something just teasing enough to make Castiel’s pulse jump.
Dean extended his hand, and without thinking, Castiel reached for it. “Nice to meet you.”
The moment their palms met, warmth flooded through him.
Dean’s grip was strong, sure. His fingers were slightly rough, calloused, like a man who had worked with his hands, despite the polished air he carried.
“It’s—” Castiel swallowed, his voice failing him for half a second. “It’s nice to meet you as well.”
Dean held his hand a beat longer than necessary, then released it, sliding into the seat across from him.
And then there was the scent.
Amber. A whisper of woodsy spice, the kind of cologne that wasn’t overpowering but lingered—something warm, masculine, something that settled in the air and made Castiel inhale just a little deeper than necessary, and he had to fight not to focus on it.
Dean leaned forward slightly, his elbows resting on the table, smirking just enough to make Castiel too aware of how intensely he was being watched.
“So,” Dean drawled, voice low, smooth. “First impressions—am I what you were expecting?”
The question caught Castiel off guard.
“I—” His mind blanked for a moment. “Your profile was… detailed.”
Dean’s lips twitched. “That’s a polite way of saying I’m what you paid for.”
Castiel stiffened. “That’s not what I meant.”
Dean chuckled, shaking his head. “Relax, baby, I’m just messing with you.”
Baby.
Something unfamiliar coiled tight in Castiel’s stomach at the way Dean said it, smooth and teasing, like he enjoyed watching Castiel react.
Dean’s gaze flickered over him again, sharp, assessing.
“So,” he said, leaning back, voice shifting into something more business-like. “Tell me what you need. Give me the rundown.”
Castiel took a slow breath, forcing himself to focus.
“I need someone to play the role of my partner for four days,” he began, keeping his tone professional. “My family is expecting me to bring someone, and I made the mistake of telling them I was already in a relationship.”
Dean raised a brow. “Ah. The classic fake boyfriend scenario.” He smirked. “Love it. So, what’s the dynamic? How serious are we?”
Castiel hesitated. “Serious enough to be believable, but not excessive. My family will expect interaction, but nothing too over-the-top.”
Dean tilted his head slightly, eyes glinting with mischief. “So we’re talking hand-holding, affectionate smiles, maybe an arm around your waist? Or do you need the whole package—kisses, stolen glances, finishing each other’s sentences?”
Heat rose unbidden in Castiel’s face.
“I—I suppose we can discuss that further,” he said, voice carefully even.
Dean grinned. “You’re cute when you overthink.”
Castiel bristled. “I don’t overthink.”
Dean hummed, clearly not convinced.
“I can do this,” Dean said, “but before we make it official, I have one important rule.”
Castiel frowned slightly. “Which is?”
Dean held his gaze.
“We meet as strangers, we part as strangers.”
A strange, hollow feeling settled in Castiel’s chest.
Dean’s voice was casual, but there was something beneath it. Something firm. Final.
“No messy attachments,” Dean continued. “No real feelings. We sell the story, play our parts, and when it’s over, we go back to our lives like it never happened.”
Castiel inhaled slowly.
This was transactional. That was the entire point.
So why did that simple rule feel like a warning?
“Understood,” he said quietly.
Dean studied him for a moment, then nodded.
His grin hadn’t faded, but his eyes sharpened, his posture shifting ever so slightly. The relaxed charm was still there, but now, it was layered with something more precise—business mode engaged. He leaned back, stretching one arm along the back of the booth as his other hand casually tapped against the table top.
Before Castiel could say anything, Dean raised two fingers, catching the waitress’s attention with an effortless ease that made Castiel wonder how many times he’d done this before.
The waitress approached, smiling. “What can I get for you?”
Dean glanced at Castiel. “You good?”
Castiel hesitated, then nodded. “Yes.”
Dean turned back to the waitress with an easy smile. “I’ll take a double shot of whiskey—same as him. And we’ll keep it open for now.”
The waitress nodded, taking Castiel’s empty glass and slipping away with a quick, professional grace.
Dean exhaled, rolling his shoulders back before returning his attention fully to Castiel. “Alright,” he drawled, the teasing lilt in his voice deliberate. “Let’s talk numbers.”
Castiel braced himself.
Dean took a slow sip of his drink before continuing, his tone smooth and practiced. “For four full days—travel, meals, social events, round-the-clock availability—you’re looking at $20,000.”
Castiel nearly choked.
He did his best to school his features, but something in his expression must have given him away because Dean’s smirk widened, amused.
“But,” Dean continued before Castiel could even attempt to recover, “since you’re a first-time client, I’ll knock off 20%. New client promo, let’s call it.”
Castiel blinked, quickly calculating in his head. That still left $16,000.
Sixteen thousand dollars.
For a fake relationship.
He could afford it—technically. He wouldn’t be in his position if he didn’t have financial stability. But knowing he could pay the amount didn’t make it easier to accept that he was about to drop a small fortune on a temporary boyfriend.
Dean must have caught the hesitation, because he leaned forward slightly, voice lowering just enough to feel more personal.
“I get it,” he said, his tone smoother now, reassuring. “It’s a lot. But what you’re paying for isn’t just someone to stand next to you for a few days.”
Castiel frowned slightly, saying nothing.
Dean gestured vaguely. “You need someone who can sell this. Who won’t break character when your mother starts grilling me about our romantic first date, or when your brother tries to catch me slipping. You need someone who can walk into that house and make every single person believe that we’ve been together for months. That we’re in love.”
Castiel’s breath hitched slightly at the weight of the words.
Dean wasn’t just confident—he was assured. Like there was no doubt in his mind that he could make Castiel’s family believe.
Castiel exhaled through his nose, knowing Dean was right.
“This isn’t about showing up,” Dean continued, voice low. “It’s about making sure no one questions a damn thing.”
There was a sharpness in his gaze now—not arrogance, but certainty. The kind of confidence that said I know exactly what I’m doing.
Castiel straightened his shoulders, his decision solidifying.
“I understand,” he said. “I’ll pay it.”
Dean’s brows lifted slightly, almost impressed.
“Alright then,” he said with a smirk.
There was something almost relieved in the way Dean leaned back in his chair, as if Castiel passing that hurdle had made him more interesting.
A moment of silence settled between them, but it wasn’t awkward. If anything, it felt like Dean was letting Castiel breathe before moving forward.
Then, Castiel spoke again.
“If we’re doing this,” he said carefully, “I need to know what you’re comfortable with.”
Dean’s lips twitched. “You mean how intimate we can get?”
Castiel didn’t let himself waver. “Yes.”
Dean tilted his head, his green eyes glinting with something unreadable.
“Well,” he said, voice smooth, “I have zero problem with casual affection. Holding hands, resting a hand on your back, playing up the couple act? That’s easy.”
His fingers tapped lightly against the table.
“Kissing?” Dean’s smirk deepened. “That depends.”
Castiel raised an eyebrow. “On what?”
Dean leaned in slightly, his voice just above a murmur. “On you.”
Castiel’s breath stilled.
Dean studied him, waiting, his expression unreadable.
“Some guys get weird about it,” Dean continued, low and steady. “Some don’t care at all. So tell me, Castiel—how comfortable are you kissing your fake boyfriend in front of your family?”
Castiel’s jaw tightened slightly, caught off guard by the reversal.
“I…” He exhaled. “If the moment calls for it, I wouldn’t be opposed.”
Dean’s eyes flickered with something sharp, something knowing.
“Good to know.”
The waitress returned, setting their drinks down. Castiel reached for his immediately, taking a slow sip to steady himself.
Dean, however, was still watching him.
“And behind closed doors?” Castiel asked, keeping his voice even.
Dean chuckled, low and rich. “That’s a different conversation, sweetheart.”
Something about the way he said it made heat crawl up Castiel’s spine.
“But if you’re asking whether I expect more,” Dean added, tilting his glass slightly, “the answer is no. I don’t cross lines unless invited to.”
Castiel nodded once, ignoring the way his stomach twisted.
Dean tapped the rim of his glass. “Alright,” he said. “Tell me about them.”
Castiel frowned. “About who?”
“Your family.” Dean took a sip of whiskey. “What am I walking into?”
Castiel exhaled. “My mother is excitable. She loves the holidays, loves family gatherings, and she especially loves doting on her children’s partners.”
Dean grinned. “So she’s gonna love me.”
Castiel’s lips twitched. “She’s going to interrogate you.”
Dean chuckled. “I can handle that.”
“My brother, Michael—he’s the oldest, a lawyer, always watching, always judging.”
Dean hummed. “So I gotta be on my best behavior.”
Castiel nodded. “My sister, Anna—she’s easygoing. More focused on keeping the peace.”
Dean smirked. “Sounds like an ally.”
“Then there’s Gabriel,” Castiel continued with a sigh.
Dean raised a brow. “Ah. And what’s his deal?”
“He lives to make my life difficult,” Castiel said flatly. “Expect sarcasm. A lot of it.”
Dean’s grin widened, almost excited. “Sounds like fun.”
Castiel gave him a look. “It won’t be.”
Dean just shrugged.
After a pause, he tilted his head, his expression softening just slightly.
“And you?” he asked. “Where do you fall in all this?”
Castiel blinked. “What do you mean?”
Dean’s gaze didn’t waver. “You’re hiring me to do this. That means there’s something about this trip that’s more than just a family gathering.”
Castiel hesitated.
Then, with a slow breath, he admitted, “They think I’m… lonely.”
Dean’s teasing smirk faded slightly.
He didn’t comment. Didn’t pry.
Just nodded.
“Well,” Dean said after a beat, voice softer, “guess I’m about to change that.”
Something about the way he said it made something shift in Castiel’s chest.
Dean exhaled, finishing his drink. “Alright,” he said, smirk returning. “When do we leave?”
Castiel took a slow breath.
“In three days.”
Dean grinned. “Then buckle up, sweetheart. You just got yourself a boyfriend.”