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waywardxwords · 11 hours

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Chapter 9 - Stay (Taking Chances)

Summary: After a random encounter introduces you to Dean Winchester, you can't shake the magnetic pull you feel towards him. For years, you've felt like everything in your life is under control--a promising career, financial stability and no real responsibilities. Dean's a hunter; it's his life and job. But somehow when you meet, your worlds are flipped upside down and you have to decide if it's a chance worth taking.

Chapter Warnings: Slight language

Pairing: Dean Winchester x female!reader

Word Count: ~3.4

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One blink, then two. The hum of the engine and vibration in the seat of the car reminded you where you were. There were so many emotions that coursed through you as you remembered: demons, monsters, Dean.

Your nose twitched as you smelled the air and your eyes were drawn over to Dean. The sun was out now–high in the sky.

“Dean?” You cleared your throat as you shifted in the passenger seat to sit up fully. He did a double take before he smiled.

“Morning, sunshine,” the gruffness to his words and the look on his face made your stomach flip–or was that hunger? You settled on a mixture of both.

“What time is it? Where are we?” You asked as you blinked a few more times to try to take in your surroundings.

“It’s about 8:30,” Dean answered as he glanced at the clock. “And we’re about an hour outside of Louisville, Kentucky.”

“Jesus, I slept for eight hours, Dean! You should’ve woken me up,” you rubbed the sleep from your eyes and felt around your hair inconspicuously. You didn’t want to give away that you were slightly concerned with what you looked like after passing out in the passenger seat. God, what if you drooled?! You swiped your fingers across your mouth quickly.

“Nah, you needed the sleep,” he answered simply. “You had a rough few days there.”

“Thanks,” you breathed. Suddenly your stomach groaned and you hoped he couldn’t hear it. “I’m starving. How about we stop and switch off again?”

“Sounds good to me,” he answered as he eyed the next exit.

“Let’s do fast food,” you said as he took the exit. “We can do a bathroom break and get it to go so we can get back on the road.”

It was a quick stop; you both used the bathroom and ordered breakfast sandwiches and hashbrowns to go and got back into the car to hit the road. You were thankful you felt fully rested.

“You should really try to get some rest,” the dark circles under Dean’s eyes, paired with how his eyelids looked super heavy, gave away that he was exhausted.

“You sure you’re good?” He gave you a side glance. You smiled and tapped the navigation system between you.

“I’ve got the map right here. I’m good,” you encouraged. He nodded once before he leaned back and closed his eyes.

The music played softly around you as you drove. You had tested it briefly about an hour after you had stopped, certain Dean had found a deep sleep by the sound of his soft snores.

You had to stop about four hours in for a quick bathroom break, but Dean hadn’t stirred. According to Google maps, you had just about two hours left now until you’d reach Lebanon.

“If you want it to be good girl, get yourself a bad boy,” you sang softly to the music that came through your speakers.

“What are you listenin’ to?” Dean’s voice was deep and gruff, still laced with remnants of sleep.

You felt like you jumped out of your skin and clutched at your chest as you sucked in a gasp of air.

“Jesus,” you muttered as you looked between him and the road. “Don’t do that!”

Dean chuckled as he pulled his hand over his face to wipe off the sleep. “Do what?” His lip picked upwards in a smirk.

“Scare me like that, you about gave me a heart attack,” you breathed as you tried to calm your heart as it thudded against your sternum.

“Sorry, sweetheart,” he grinned as he adjusted his position on his seat. “But seriously, what is this noise?”

“The Backstreet Boys,” a smirk tugged at your lips as you drove. Dean wiped the sleep from his eyes and you stole a glance. “I told you I’d get you listening to some boy band classics.” You remembered back to when you first saw Dean again and you had walked around town, talking about all of your favorite things.

Dean audibly groaned. “How is this on your list of favorites?”

“Oh, this song did things to me back in the day,�� you laughed softly.

“What kinda things?” Dean almost wiggled his eyebrows as he watched you. You just smirked and nibbled on your bottom lip with a shrug. “Uh uh,” he muttered, and without another thought he reached over and pulled your lip free with his thumb. “Keep that lip outta your teeth. It’s dangerous.”

Laughter bubbled in you once more. While you fully trusted Dean, there really hadn’t been any conversation about what this was between you now. Not after everything that had happened. It felt safer to change the topic.

“Only a few hours out now,” you glanced down at the navigation system. “I can stop for a bathroom break. Do you feel rested?”

Dean nodded. “Oh yeah, that’s the best sleep I’ve gotten in a while,” he said as he glanced at the map on the screen. “I should probably explain where Sam and I live to you before we get there.” He pulled at the back of his neck uncomfortably as you flipped on your turn signal to exit at the rest stop that was approaching.

You cleared your throat as you prepared to tell him what your brain had mulled over while he slept. “About that,” you said slowly at first. “I don’t want to invade your space, Dean. I was thinking it might be best if I stay in a hotel close by. At least until we figure out what’s going on.” You left out the words between us and avoided eye contact. The distraction of keeping your eyes on the road was a good enough reason to not meet his gaze.

He was silent, maybe he wanted to try to find the right words, so you filled the gap with your reasoning.

“I just don’t want to invade your space—for you and for Sam. I’d still be close by, in case of emergencies or anything,” you explained and stole a glance as you pulled into a parking spot at the rest stop. You could no longer blame keeping your eyes on the road for not looking at him, and you were also curious as to how he felt or what he was thinking.

“You’re not invading our space,” he tried to assure you. “But, I understand if you’d be more comfortable in a hotel.” The words seemed painful as he said them, but he didn’t push back, and you appreciated that.

“Just for a few days, maybe,” you sighed. “This is all just a lot.”

Dean nodded. “I get that,” he agreed. “A few days.” He smiled to show you it was okay.

The rest of the drive had gone well, it was easy. Dean found a hotel that wasn’t far from where he lived, and Sam had met you both there with the Impala.

“Hey, Sam,” you smiled at the younger Winchester as Dean moved his bags from your trunk to the Impala’s back seat, and then hauled your bags out to carry into the hotel.

“Hey,” he smiled, though you felt as though something might be off. “How was the drive?”

“Not terrible,” you took a glance at Dean as he closed your trunk. Sam cleared his throat.

“Listen, I just want you to know, you staying with us isn’t imposing on me at all,” Sam’s words sounded like Dean had filled him in via text at the rest stop earlier. “You’re welcome to stay with us.” He lowered his gaze to make sure you could see his eyes. You knew he was being genuine.

“I appreciate it,” you said truthfully. “I just feel like I need a few days to catch my breath and then I can reevaluate.”

Sam nodded, as he seemed to understand.

“Let’s get you checked in,” Dean placed his hand on your lower back just above your jeans. The feeling of his hand sent a wave of warmth even through the sweater you had on, and you relished in the feeling as he led you to the lobby of the hotel.

Both Sam and Dean seemed on alert as you checked in with the lady at the front desk. She didn’t seem phased as she handed you a key card and told you breakfast was between 6 and 9. You smiled and thanked her as you made your way to the elevators.

There was silence as the elevator climbed to the third floor. You scanned your key against the lock on the door, but Dean’s arm went out in front of you and he grasped the metal handle.

“Give us a sec,” his voice was low as he pushed into the room with Sam behind him. You caught the door with your foot and watched as they checked the room. It was just a bedroom and bathroom, so there wasn’t much to search. The rattle of the shower curtain echoed against the bathroom’s tiled walls. Once they felt comfortable, Dean nodded for you to come in.

You noticed then that Sam had brought a backpack up with him from the Impala. He set it down on one of the beds and unzipped it.

“So here’s the deal,” Dean said somewhat firmly. “You can’t leave this room under any circumstances unless Sam or I are with you. Don’t open the door for anyone.” Sam had taken a large container of what looked like salt and started putting it in front of the windows. “When we leave, I need you to take that salt and put it in front of the door, alright?”

“Do I want to know why?” You practically gulped as you watched Sam work.

“Probably not,” Dean answered softly. “I need you to wear this.” You noticed he had a dainty silver chain in his hand with a charm on it. Your fingers reached for the jewelry and you swallowed when your skin grazed his. Upon further examination, you realized this charm was a carbon copy of Dean’s tattoo on his chest.

“What is this?” You asked as you looked over the design.

“It’s an anti-possession charm,” he explained carefully. “If you have this on, demons—like Meg—can’t possess you. Like what happened to your friend, Jen.” He swirled his finger to have you turn around, and you did. Even though all of this sounded absolutely insane to you, all you had to do was pull the images of Jen/Meg from your memory to remind yourself it was all very real.

You gathered your hair over your shoulder and held it there as Dean adjusted the chain around your neck and his fingers worked to clasp it behind you. Every time his fingers flitted over your skin, you felt somersaults in your stomach.

The sound of an aerosol can being sprayed jostled you back to reality as you spun around to see Sam with a can of spray paint.

“What are you doing?” You asked as he finished a design underneath a rug in front of the doorway.

“It’s a Devil’s trap,” Dean explained. “We’ll put one in front of the window, too. If a demon gets in, they can’t get out of that and they can’t hurt you.”

That felt slightly reassuring, but you were still on edge. “I’m not getting my security deposit back, am I?” There was a nervous chuckle to your question.

“Sorry,” Sam managed a small, sympathetic smile as he finished his art work and let it dry for a moment before he tossed the rug back over. He went back to the window to create it again.

You were distracted by the sound of Dean emptying the remaining contents from the backpack onto the bed. There was, what looked like, an iron rod, a jug of water, more salt, a flask and then a serious knife—it reminded you of a hunting knife or something. The knife alone made you gulp, but everything combined had your head spinning.

“What’s all this?” The words came out as a whisper. Dean placed his hand on that familiar spot on your lower back once more and led you to the edge of the bed. This time was a lot different than when you were in that bed and breakfast just a few days prior.

“This,” he picked up the jug. “Is salt water. The flask is holy water,” he explained. “That’s an iron rod, extra salt for the doors and windows, and a silver knife. These are all the weapons I could think of for the monsters we hunt.”

“How will I know what to use?” You asked as your eyes moved over all of the things placed before you. Silently, you wondered if maybe you should have stayed with Dean and Sam, after all.

“Honestly, there’s so much to explain,” Dean started as he let out a breath. “Your best bet is to start slingin’ salt water and holy water,” he motioned to the jug and flask. “I don’t think you’ll see a spirit, because that’s more complicated—so you probably won’t need the iron. Werewolf or someone who looks like me, but isn’t me,” he picked up the knife. “Silver blade.” He paused for a second. “Shit, I didn’t think about the vampires…” his words were quieter as he processed.

“I’m sorry, werewolves? Vampires? And what do you mean, someone who looks like you but isn’t you?” Your thoughts were swimming around in your brain. But it wasn’t a leisurely swim, it was like there had been a damn tsunami and waves were flooding and crashing every second.

Dean somehow just knew. Maybe it was the way the words were flowing haphazardly from your lips, or the way your fingers had started to tremble. But he knew.

He reached down and tugged on your wrist so you faced him. “Take a breath, sweetheart,” he said softly. Sam had stilled his movements after he readjusted the rug by the window. “Sammy, can you give us a minute?”

Sam nodded. “Sure thing,” he gave you a small smile as he left the room and closed the door behind him.

Dean’s hand came up to catch your cheek in his palm. It was impossible not to be pulled into the warmth of his grasp. You closed your eyes at the feeling.

“I know this is a lot,” he kept his voice low. “I don’t want to overwhelm you, but I want to keep you safe.” His words hit at a spot in your heart that caused a flutter across your chest.

“You don’t have to save me, Dean,” you reached up and held his hand on your face in place.

“Oh, I’ll do whatever I can to keep you safe,” he said matter-of-factly. “That’s not even a question in this scenario. I’m just sorry I got you pulled into this shitstorm of my life.” His words felt sad to you, and you didn’t think he meant for them to be. His hand fell from your cheek back to his side.

“Dean, I really, really like you,” you made sure you held his gaze as the words flowed. He needed to see the sincerity behind him—to know you were speaking the truth.

“People I care about get hurt,” he said simply, but little worry lines had appeared by his eyes and between his eyebrows. His eyes matched the sadness of his voice. “Once we figure out what’s going on and I can make sure you’re safe,” he started carefully, as if he didn’t want to say the words but more so needed to. “I want to get you back to Virginia. Back to a normal life.”

The words struck as if you had been slapped and your eyes widened. That wasn’t something you had expected him to say. “I don’t know, I feel like that’s for me to decide. It’s my safety you’re worried about, right?”

“Just yesterday, you were determined I was a psycho serial killer who faked my death and was on the run,” he quipped with a sad smile.

While he wasn’t wrong, you still weren’t sold on his reasoning. “Can we just say we’ll take this one day at a time? Go from there?” You asked him gently.

His eyes moved between yours and he managed a single nod. “Okay. One day at a time.”

“Thank you,” you breathed. The heaviness of the day fell over you, and it seemed as though Dean noticed.

“I’m going to get going, let you get some rest,” he cleared his throat and took a step back. “I’ll be back first thing in the morning, or sooner, if you need me.”

You followed him towards the door.

“Remember, salt line behind the door once I leave. Don’t open it for anyone. I’ll say ‘Atlanta’ when I come back,” he placed his hand on the door handle and turned back once more.

“Got it,” you nodded as you listened to his instructions. “And Dean?” He turned back towards you again for you to continue. “Thank you for bringing me here. For keeping me safe.”

Dean nodded once with a small smile. There was a hesitation there, but you could almost make out when his heart changed his mind, and you could have sworn you heard a fuck it. He leaned back towards you and pressed his lips to yours with his hand on your cheek once more.

Heat radiated beneath your skin, and you weren’t sure if it was from the traces of his fingertips there or the rush of his lips on yours—probably a mixture of both.

“Goodnight, Atlanta,” he murmured against your lips as he pulled away.

“Goodnight, Dean,” you couldn’t help the smirk that tugged at your lips as he opened the door and closed it carefully behind him.

Dean climbed into the driver’s side of the Impala and closed the door behind him. Sam did the same in the passenger seat.

“She doing okay?” Sam asked.

“As good as can be expected,” Dean sighed and pulled his hand over his face. Sam was silent for a few seconds, but Dean knew he had plenty of thoughts floating around in his brain. “Go ahead and say it.” He said firmly.

“Say what, Dean? Everything I have to say, you already know,” Sam sighed. Dean didn’t respond, and instead put the Impala into reverse and backed out of the spot. “I just feel like it’s not the right time to get this sucked in.” There it is, Dean thought to himself.

“Don’t you think I know that?” He bit back but refused to meet his brother’s gaze.

“We know what we need to do for the second trial now,” Sam said carefully. Dean’s jaw flinched.

“Kevin figured it out?” He glanced between Sam and the road. Sam just nodded.

“We both know it’s going to get a hell of a lot worse before it gets better,” Sam glanced out the window and then back at Dean.

Dean nodded, his jaw set in a firm line. “I just need to keep her close by. At least until this shit is over. If Meg has made an appearance, we know more will be coming.”

“I thought we were keeping her close in the bunker. How are you going to keep her safe when we’ve got a fifteen minute drive between us? The bunker’s the safest place for her,” Sam wasn’t wrong.

“I know, but she’s scared. I was having a hard enough time trying to explain the bunker to her,” Dean sighed. “I’m dropping you off and going back to the hotel. I’ll sleep in the Impala in the parking lot.”

“Does she know that?” Sam smirked from his spot in the passenger seat, though he could’ve assumed the answer.

“No, and we’re keeping it that way,” Dean said firmly. “It's the only way I know I can keep her safe.”

A/N: Sorry for the delay on this one! We decided to extend our vacation by a few days, and I hate posting updates from my phone, so thanks for your patience!

Things will certainly start to pick up with this story now (after some consideration, I also think this might go beyond 13 chapters--TBD). I ended up getting some ideas as I re-watched bits and pieces of seasons 8 and 9, so we shall see what happens!

I hope you're loving it so far! Thanks for all of the likes, comments and reblogs. I appreciate you all!

Chapter 10 will be posted on Thursday, 5/2!

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waynes-multiverse · 1 day

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Plastic Hearts – Part 23

Pairing: Director!Dean Winchester x Actress!Reader

Series Summary: Los Angeles, 1985. Y/N’s a young actress without any success, hopping from one failed audition to the next until one desperate mistake brings her to her breaking point. Dean Winchester, on the other hand, is a grade A asshole and washed-up director at the end of his career, known for his godawful slasher movies in the 70s and his love for blow, booze, and women. Lost in the toxic Hollywood life, their paths cross when one hopeless little wrestling show changes their trajectory.

Chapter Warnings: +18, language, smut, fluff, angst, quiet hurt & a touch of heartbreak

Word Count: 5.7k

A/N: Oh, you'll hate me again for ending it like this. Have fun, guys 😂

<< 22 || Spotify Playlist || Series Masterlist || Main Masterlist

23. Every Breath You Take

“More?” Dean offers the half-emptied wine bottle and holds it over Y/N’s glass as they sit around the dinner table. The actress throws him a raised look with a little smile playing on her lips.

“Are you trying to get me drunk? You don’t have to. I’m already sleeping here,” she points out in amusement.

“Yeah, but when you’re buzzed, you let me do more shit.” The green-eyed director smirks.

“Ew, Dad!” Claire groans next to him. “I’m right here. This is why I don’t wanna do family dinner with you guys.”

“This was actually a nice idea,” Y/N says with a smile so bright it shows her dimples. “Thanks for cooking tonight. Perfect way to start our last week of filming.”

Dean’s heart stings slightly at her words, but he covers it with a tight smile. The last three weeks passed by rather quickly, and each week, he grew more worried, more nervous, more depressed, and more anxious. This was it. Seven more days before it all imploded. Six more nights before he might not see her again.

He has been wracking his brain, trying to come up with solutions to save the show – to keep her. Cas and Jo are out on fairs, networking with networks and showing their tape to other producers in hopes of getting picked up by someone else, still without any success.

“So, uh, any plans so far? Heard some of the girls are going to auditions, looking for other jobs,” Dean notes and nurses his beer. He doesn’t hold it against them. It’s the business, after all, and everyone’s trying to survive and find their next paycheck.

Y/N bobs her head and sets her wine glass down. “Yeah, actually. I was thinking about taking your advice and going to New York for auditions. I like the idea of doing theater or maybe even a musical.”

Dean forces a supportive smile on his face and hides the heartbreak in his ribcage. “Yeah, you should. You’d be great at it.”

“But, uhm, for now, I’m actually driving to San Diego in a few days for an audition for a musical. I’m not gonna get it, but I figured it’d be fun,” she tells him, and even though she downplays it, Dean can see the excitement sparkling in her eyes.

“Oh, c’mon, why wouldn’t you get it?” he encourages her. He promised himself he’d always be her cheerleader, no matter his own feelings on the subject. He’s trying a new thing these days – it’s called being less selfish.

But God, he hopes she gets it. San Diego is a lot closer to LA than New York.

Y/N snorts into her glass, chuckling. “It’s a Sondheim musical, Dean. I’m not expecting to get it. It’s just good practice.”

“Aiming high, huh?” Dean laughs despondently and takes a big gulp of beer to choke down his tears.

Dammit, Dean thinks. He wishes he could call the dude and tell him what a great woman and actress Y/N is. He’d be lucky to have her in his production. Maybe the director could bribe him to hire her? Would that take things too far?

“How are you gonna get down there?” Dean’s eyes drift to the leg in a cast that rests on a chair next to him.

Y/N gives him a shrug of her shoulders. “I don’t know. Take the bus?”

“I’ll drive you,” he says with a swig of his beer. See? Supportive. He’s really proud of himself, although he wishes he were a lot drunker right now.

“Ooh, uh, Claire, I borrowed two dresses from Alex for you. I put them in your room. You need to pick one for your Winter Formal,” Y/N tells his daughter with a bright smile.

But Claire shakes her head with teenage defiance. “I don’t need a dress. Jack and I are going ironically.”

Dean’s brow furrows in confusion as he blinks at his kid. “What the fuck does that mean?”

Claire rolls her eyes in response and groans. “Ugh, Dad, you’d think for someone who lived through counterculture, you’d understand.” With that, she gets up from the dinner table and takes her empty plate to the kitchen sink.

“I know what she means,” Y/N mumbles nonchalantly.

Dean’s bewildered gaze darts to her. “Really? What?”

Y/N coolly shrugs her shoulders as she sips on her wine before she sighs defeatedly. “Fine, I don’t know. I just wanted to sound cooler than you,” she admits with a cute smile.

Dean snorts a laugh. “Yeah, good luck with that.”

“I’m going to bed. Good night! Don’t be too loud!” Claire yells before the door to her room slams shut.

Dean watches Y/N as she leans back in her chair with a blissful sigh and empties her glass. She has pretty much spent every night at his place since the hospital. At this point, the director has gotten so used to it that he wouldn’t know what to do with himself if one night she didn’t. Why can’t it stay this way?

He never thought he’d be someone who wants to have family dinners every night.

“Too tired for dessert?” he asks with a wiggle of his eyebrows and his signature smirk.

Y/N laughs lightly. “I wish one of these days you’d offer me actual dessert,” she quips.

“Like what? Chocolate cake? Pie? I’d actually love some pie. Maybe we should get one for tomorrow night,” Dean muses, chuckling.

Y/N grins mischievously at him and leans her elbows on the dinner table, resting her chin in her palms. “Maybe you can eat pie off of me.”

Dean curls his lips, his cheeks blushing at the idea alone. His dick seems to like it, too. “God, I love… your brain,” he quickly corrects his course before the wrong words slip out.

And it’s not like it isn’t true. While Y/N hasn’t been able to act and tumble around the ring, she’s been coming up with storylines and basically coordinated matches for the past three episodes. She’s also constantly by his side and mans the booth with him. If Dean didn’t sleep with her and like her, he’d actually be scared she’s coming for his job. She’s pretty much directing at this point, and he just lets her because, well, did he actually ever care?

But his declaration is only a small part of the truth, the full truth being that he loves more than just her damn brain and has for a long while. He’s been trying to say the words for weeks now, started and stopped a hundred times, and tried to pack his feelings into a coherent sentence that honestly shouldn’t be more than three words long.

However, those are some big three words. Monstrous for Y/N. And deep down, Dean knows she might feel like he does, too, but can’t admit it and doesn’t know what the hell to do with it. To her, this little arrangement between them is nothing more than friends who fuck. Only Dean’s aware that they’re actually in a deeply serious relationship, which is maddeningly ridiculous.

But hey, if he keeps his mouth shut, they might make it another five years like this without Y/N running away, so that’s something.

Dean then rises from his seat and offers his hands to Y/N. Her leg is still in a cast, so she has been wobbling around on crutches or hopping clumsily across a room. It’s pretty darn cute.

“Thank you,” Y/N says gratefully as Dean helps her up and slings her arm around his neck before he fully hoists her into his arms. She giggles as he carries her into the bedroom. “You don’t have to do this every night, you know. I can walk just fine.”

“Says you, but truth is, you’ve never seen yourself walk on these things. It’s pathetic,” he teases her and plops her carefully down on the bed.

He flings off his shirt and removes his jeans and underwear as Y/N unbuttons her blouse. The mattress dips as he climbs into the bed and helps her discard her pants. It’s routine at this point, but Dean has really started to cherish the stability. Every morning when he wakes up and smiles at her, he loves knowing that he’ll fall asleep right next to her at night all over again.

Gently, he spreads her legs and slots between them. His lips find hers in the moonlit dark and kiss her with deep affection and burning love, always pouring his whole heart into each kiss and hoping one of these days it’ll stick.

Grabbing a condom from the nightstand, he rolls it over his throbbing length and positions his dickhead at her entrance, slipping into her tight channel till she’s full of him. Her lips part as the same little gasp escapes her that he hears every time he enters her. He loves hearing that noise almost as much as he loves to hear the big one when she comes and the medium ones in-between.

Sometimes, Dean makes her come before, but on nights like these, when she’s already had half a bottle of wine, he rather works quick. While wine makes her louder and more daring, it also renders her quite sleepy.

“Fuck,” she sighs and closes her eyes with a euphoric smile, her pussy gripping his cock tight as she clenches around him. “You’re always so good at that.”

Dean smiles amusedly. Wine makes her chatty, too. “I haven’t even done anything yet, sweetheart,” he remarks.

“Well, I guess I just-… I just love your cock,” she says bluntly and grins up at him. “And those lips.”

See? Wine.

“These ones?” Dean asks teasingly and leans down, pulling one of her nipples between them till she squirms.

“Uh-huh, yes…” she moans softly and cards her hands through his hair, causing a groan to pass his lips. “And that tongue.”

“This one?” Dean lets his tongue roll over that same nipple till it peaks, feeling her arch her back underneath him.

“Yes, and God, those hands and fingers…” she almost whines.

“Those two?” Dean snakes a hand between their bodies, two of his fingers finding her clit and drawing tickling circles.

There’s no more strength left for words. She bites harshly down on her bottom lip and nods vividly. Her cunt clutches him tightly, eliciting a giddy chuckle from him. He loves making her squirm.

Three more squeezes, and he knows he has to move before she grows impatient. He knows her well by now, knows every little detail about her, and loves that he does. They haven’t even been able to do half the things he wants to do to her due to her current injury and inability to move (or bend) as freely.

And yet, he’s still not fucking bored, not in the slightest. He keeps waiting for it, but it never comes.

On the contrary, he appreciates the feeling of knowing someone so deeply and intimately as he knows Y/N. She has become a part of his soul, and he doesn’t know if he could ever cut her out without severely hurting himself. He’s not sure if he could survive a wound this deep.

“Dean, please…”

That was the fourth – like clockwork.

Dean manages to thrust twice before loud punk rock music shakes the walls and drowns out every noise in the entire house. Hell, the whole neighborhood can probably hear it.

Frustrated, his head drops momentarily to Y/N’s shoulder as the actress snorts a giggle. He can feel her body and cunt trembling around him, but not for the reason it should.

“Claire!” Dean shouts angrily. “Turn that fucking music down! Y/N’s trying to sleep!”

“No, she’s not!” his kid yells back through the wall and the unbearable music. “I know you guys are having sex! I don’t wanna hear anything!”

“We’re not having sex,” Dean barks and watches as Y/N gapes at him in sheer playfulness.

“Wow, you lie like that to your kid?” she teases him.

“What d’you want me to say? ‘I’m sorry, you’re right. I’m inside of her now’?” Dean retorts wryly, making Y/N burst into uncontrollable laughter as she snorts into his shoulder. “Can you please stop laughing while I’m trying to fuck you? My soldier’s already retreating.”

But Y/N only laughs harder at that, tears streaming down her cheeks as Dean’s lips purse with a sigh through his nose. She then exhales a deep, long breath, trying to calm herself. He’s seen her do this very move a hundred times during an acting scene.

She clears her throat and tries to force a more serious look onto her features. “How about a little Russian motivation?” she says in her infamous accent and smiles when his cock twitches in agreement. “Maybe some oral manipulation, yes?”

“Oh, fuck yeah.” Dean grins and leans down to capture her lips. “God, I love yo… your pussy,” he quickly corrects himself once more. That was a close one.

Alright, don’t look at him like that and don’t judge him. He’s trying. He really is.

But Jesus fucking Christ, he loves living these days. Who knew his forties would be the best time of his life?

With a big yawn, Y/N rubs her eyes and stretches her arms over her head. The shower in the main bathroom is running with Dean already in it. She grabs her crutches and hops to the window, opening the blinds to let some sunlight in.

She takes a deep breath and enjoys the morning silence for a moment, her gaze drifting out the quiet neighborhood. It has never been this peaceful in the motel. The last three weeks, she has really appreciated waking up in Dean’s bed. She knows she’s probably overstaying her welcome at this point, but he hasn’t kicked her to the curb yet, so she hasn’t been in a hurry to return to the motel, either.

He was right – the memory foam mattress is fucking heaven, especially with a broken ankle.

All in all, she imagined being benched for the show would be a lot worse than it is. Dean’s done a great job of incorporating her anywhere outside of the ring. She’s helping with storylines, training, directing, producing – really anything that could use a few tweaks. The green-eyed director is unfashionably nice to her. Maybe it’s the sex or their friendship or a combination of both. Either way, she’s grateful for him.

However, there’s this tiny voice inside her head that keeps telling her there’s a reason why Dean’s been so nice, and it’s not just the sex. It’s certain kisses and touches and looks – especially the looks – that make her believe there’s something lying underneath the surface. An iceberg so gigantic it could sink the Titanic. Whenever she catches his clandestine gazes from her periphery, there’s this inexplicable feeling that creeps through her veins.

Her peace is disturbed when excessive knocking and an uninterrupted ringing of the doorbell draw her attention to the front door. A part of her expects to find her best friend behind it. Only Jo could be this ruthless and obnoxious.

Y/N hurries to the door as fast as she can, which isn’t fast at all, considering she’s on crutches. Everything is just awkward and slow these days, but she’s been practicing moving around in hopes of joining the show again for the final episode. Billie and Donna have been helping her, too.

But as Y/N opens the door, she’s not greeted by the familiar blonde but by a brunette stranger instead. The only similarity the woman shares with Jo is that she’s incredibly hot and angry, too.

“Can I help you?” Y/N asks with a look of bewilderment, although she shouldn’t be surprised to find a mad woman on Dean’s doorstep.

“I’m Lisa Braeden. I’m looking for my daughter,” the woman says, somewhat impatiently.

Oh.

“Uh…”

Y/N stumps for a moment, eyeing the woman in front of her closely. So, this is Claire’s mother. Dean’s ex. She tries not to feel insecure around her, but it’s hard, considering the woman is a bombshell with perfect curves and flawless features. And if she looks like that now, Y/N wonders what she must’ve looked like seventeen years ago.

The actress suddenly feels very exposed in only the director’s flannel. Truthfully, she looks like she just crawled out of a gutter. Maybe it’s the fact she has just woken up and is sporting major bed-head, but Lisa probably thinks Dean took in a homeless person. The cast and crutches don’t help, either. And then, Y/N wonders why a part of her cares at all what the brunette thinks and reminds herself it’s not a competition.

“Dean? Dean!”

Her voice carries a certain amount of panic that’s probably uncalled for. Yet, it helps. The shower turns off, and not a minute later, Dean stands next to her with only a towel wrapped around his waist, his broad chest still glistening with droplets of water.

He does know how to make an entrance.

Dean’s brow is deeply creased when he takes in the woman at the door, lacking a sense of recognition, however. “What the fuck is all that noise?”

“I’m the fucking noise,” Lisa replies dryly. “I’m here for my kid.”

“Oh…” Dean stumps as well. Then, he swallows thickly and gives her a nervous smile. “Hi, uhm, I’m Dean Winchester.”

“I know who you fucking are, you moron,” Lisa huffs, shaking her head. “You got me pregnant. Where’s Claire?” When neither Dean nor Y/N answer, Lisa rolls her eyes and waltzes past the two inside the house. “Claire!”

“Sure, come on in,” Dean mutters under his breath and shares a wide-eyed look with Y/N, hoping for some guidance.

The actress eyes him up and down, pensively licking her lips. “Maybe you should get dressed.”

With some pants and a shirt on, Dean and Y/N have retreated to the kitchen and sip quietly on their cups of coffee while Lisa and Claire scream at each other. It’s a classic mother and teenage daughter battle. Claire fights for freedom, while Lisa fights for control.

“I had sex with that woman seventeen years ago. Now she’s in my house, yelling at my kid,” the director voices his thoughts out loud, a hint of trepidation shimmering in his green eyes.

“Yup, life has a way of catching up with you. Kinda learned that this year,” Y/N notes with pursed lips and sends him a smile. “But hey, they’re your family now. Kinda nice, right?”

“I can’t tell if you’re joking,” Dean huffs with a bitter look and watches Y/N place her mug in the sink.

“I should probably go. Leave you guys to figure this out,” Y/N announces, one hop on a healthy foot away from walking out the door. “I’ll call a cab.”

“No, don’t! You can’t leave me here alone with them,” Dean pleads, the sheer panic and desperation visible in his eyes and audible in his voice. His gaze bores into her. “C’mon, I need you. This is one of those, you know, friendship moments. Like abortions and getting over coke addictions.”

Y/N lets out a small sigh. How could she leave him after everything he’s done for her? She basically has no choice but to stay and help him through this. “What d’you want me to do? Mediate?”

“I don’t know. Maybe.” Dean shrugs helplessly. “I just know I’m gonna say all the wrong shit at the wrong time. Please. I don’t wanna lose my kid. Help me.”

As she catches his gaze, there’s that inexplicable feeling creeping through her veins again. This time, it even tugs on her heart.

“Okay, uhm, alright. I’ll stay,” she promises him, offering him a small smile of comfort.

Unbeknownst to her, though, Dean comes close to saying the three ominous words once more. It’s getting harder every day to keep them inside. How long does he have until he bursts? He feels like a ticking time bomb.

“Maybe we should all sit down and talk?” Y/N suggests as soon as Claire has stormed into her room and slammed the door in upset.

“About what?” Lisa barks, half-annoyed as she rests her hands on her squared-off hips. “She’s been lying to me for months.”

“Okay, in my defense, she told me you were crazy,” Dean explains with an innocent shrug.

“I don’t care if she told you I beat her and locked her into the basement. If a kid has run away from home, you call their mother,” Lisa retorts furiously.

Dean purses his lips in defeat for a moment, especially when Y/N seems to agree. She’s kind of his moral compass, but he’s not ready to accept his loss yet. “Well, you didn’t call me to tell me you were having a kid. My kid,” he argues and knows it’ll probably backfire. He can tell by Y/N’s frown.

“Oh, excuse me for not calling the guy who didn’t stay for breakfast,” Lisa counters with an eye roll.

Dean’s brow furrows, shaking his head. “I don’t think that’s what happened.” Granted, he’s been high for two decades now.

“I asked if you wanted pancakes. You said, ‘No, thanks, but that was fun.’ And then you got into your car and bolted, never to be seen again,” Lisa recalls, frowning.

“Uhm, that sounds like it was a long time ago,” Y/N interjects in his defense, chuckling nervously. “He’s a different and more mature person now.”

Dean’s heart swells to twice its size. It’s probably the nicest thing anyone’s ever said about him. Although, he can tell she only said it to win Lisa over. She’s a good actress, making even him believe her words. But she’s helping him, so it’s the thought that counts.

“Thanks for the input. Who are you again? Are you his fucking maid?” Lisa arches a brow at her, eyeing her up and down.

“No, she’s not my maid,” Dean replies fiercely but then doesn’t know what else to say. Girlfriend? Lover? Friend? Nothing sounds right. “She’s my, uhm, she’s my actress. She’s my… You know, she’s… She’s Y/N.”

At that, Y/N’s brow draws together in the middle with a tilt of her head. Dean surmises that answer probably sounded even weirder.

“Yeah, I can see you’ve changed so much.” Lisa scoffs sarcastically and folds her arms over her chest, her patience running low.

Y/N subtly clears her throat, deciding to step in. God knows the director needs all the help he can get. “Okay, uhm, it doesn’t really matter who I am,” she says and shares a look with Dean, who anxiously chews his bottom lip raw. “What matters is that Dean has really connected with Claire over the last few months. He’s enrolled her in high school, she has joined AV club, she’s got a really nice and sweet boyfriend.” Dean grimaces at that last part, but Y/N skillfully ignores it and continues, “They’re going to Winter Formal tonight.”

“Yeah, I’m chaperoning,” Dean announces proudly. “This dance is very meaningful to her.”

Lisa snorts a laugh, clearly amused. “My kid does not go to dances.”

“Yes, I do!” Claire suddenly stands in the middle of the living room with the brightest smile. It’s freaky, really. She gleefully holds up the two dresses Y/N brought over last night, feigning her excitement. “Which one should I wear?”

Lisa and Dean disagree on the dress choice, but when Y/N sides with Lisa, Claire takes the hint and quickly disappears back into her room.

“It’s just one night, and it will give you two some time to catch up. Figure this out,” Y/N advocates suggestively.

“Yeah, what she said,” Dean agrees and clears his dry throat, wishing he had a bottle of booze in his hand to calm his nerves. Man, in stressful situations like these, he does miss coke sometimes. But fucking Y/N has been a great substitute, so maybe he’ll just do that as soon as that crazy woman leaves his house again. “Look, I get that you’re angry. But I’m really trying here, okay? She’s doing great at school, I gave her a curfew… I wanna make up for lost time,” he explains sincerely. Y/N sends him a proud smile.

“Fine, one night, but tomorrow we’re leaving,” Lisa relents with a sigh. “I’m not gonna indulge this fucking father-daughter fantasy,” she huffs and then finally storms out of the house.

Y/N exhales a long sigh of relief. “Well, that went better than expected.”

“You think?” Dean checks insecurely. He doesn’t know what he would’ve done if Y/N hadn’t been here to support him. “You’re coming tonight, right?”

Surprised by the request, Y/N’s brow meets her hairline. “You want me to go to your daughter’s Winter Formal with you?”

“Yes, obviously,” Dean states matter-of-factly and blinks at her. “You can’t leave me alone with that woman.”

Y/N heaves another sigh as she looks at him. “Okay, fine,” she surrenders.

Sitting on the bleachers of a fully decorated gym, Y/N realizes she has kind of missed high school. At least, everything used to be much simpler back then. Your crush would ask you to go steady, you’d say yes or no, and then you’d be broken up shortly after prom.

Adulthood is complicated. People are complicated. And love is goddamn unfathomably complicated.

“It’s so weird seeing her with her first high school boyfriend,” Lisa notes with a small sigh next to her. “I still remember her drawing with crayons. Now, she’s running miles away, lying, and making out with a boy.”

“Yeah, teenage romance is a lot more intense,” Y/N says, chuckling softly.

“She won’t wear a dress to my wedding. Refused to. Screamed bloody murder,” Lisa says thoughtfully. “But after spending a few months with her estranged father, she suddenly puts one on.”

“People are complicated,” Y/N reiterates her earlier sentiment.

Claire is complicated. Dean is complicated. And Y/N? She might be the most complicated of all.

“My fiancé is not,” Lisa says, a delicate smile playing across her lips. It’s enough to show her happiness. “I always used to date these guys that would run so hot and then completely cold the next minute. I never knew where I stood. It was exhausting.”

“Yeah, I get it…”

Y/N’s eyes drift to Dean as he chats with one of the other dads by the buffet. She doesn’t know what the director wants from her. She doesn’t know what their relationship even is. One minute, it feels epic, like a love so legendary it should only exist on the silver screen. And the next minute, it feels trivial, like it should’ve never existed at all.

But Dean’s not the problem. Deep down, she knows what that creeping feeling in the pits of her stomach is. And she knows she’s not ready for it. Truth is, Y/N has no idea what she wants and feels lost. Because if she admits one thing, it’d mean the end of another. If she stays in LA for a guy, what would that mean for her career? She doesn’t want to end up like Jo. She’s finally about to have it all, only to realize both at the same time are a mere dream.

And worst of all, even if she did know what she wanted, she’s doesn’t know if she deserves it.

“So, what d’you do, son?” an older man next to Dean asks. He’s already balding and gray, as is the scruffy beard he’s sporting. His suit jacket with a name tag that reads “Chaperone” looks a little worn and sleazy, too. The director figured he’d be one of the oldest dads here, so this guy comes as a pleasant surprise.

“I’m a director of a women’s wrestling show,” Dean replies and takes a sip from the fruit punch. None of the kids have spiked it yet, which is quite the disappointment. What’s happening to today’s youth, huh? “And you?”

“Oh, nice.” The man nods with a smile and pulls out a business card from his suit jacket, handing it to Dean. “Bobby Singer. I own a small chain of strip clubs, although my wife Ellen would probably like me to tell you I’m a small business owner.”

“Got it.” Dean chuckles and glances at the card in his hands. “Bobby’s Body Shop. Oh, hey, I know this one! ‘Where the girls are hotter than the asphalt,’” he quotes the club’s tagline proudly, grinning. “I’m there all the time! Actually got one of your girls in my show.”

Bobby chuckles. “Well, next time you’re there, ask for me. I’ll get you a discount.”

“Thanks.” Dean smirks. And Cas claims you can only network on the fucking golf course. “Oh, hey, you should catch one of our shows. It’s our last one this week. It’s pretty badass. We’re over at the old gym in Watts.”

“Alright, I’ll see you there,” Bobby says with a smile.

Dean’s eyes then drift to Y/N on the bleachers. Last time he checked on her, she was still chatting with Lisa, but the brunette has since left. And as he glances at her now, Y/N has found herself encircled by a group of horny teenage boys, causing his brows to draw together and meet in the middle. They’re like fucking vultures.

“Shoo!” Dean barks sternly at the young men as he approaches the group and watches them scurry away with their tails tugged between their scrawny legs.

With an amused smile, Y/N arches an eyebrow at him. “Glad you’ve decided to join me. It was getting crowded. I’ve turned down about twenty offers to dance.”

“Look at you, you little heartbreaking cougar,” Dean retorts with a teasing smile. “You’re gonna turn me down, too?”

“I have a broken ankle. Did you forget that part? I can’t dance,” Y/N replies.

“Oh, c’mon, that never stopped you before. ‘Sides, I’ve got two working legs and can’t dance, either. So, what d’you say, huh?” Dean holds out his hands for her to grasp.

“Fine,” Y/N relents and grabs his hands, hopping to her feet. “Let’s do some awkward swaying.”

“That’s the spirit.” Dean laughs and rests his palms on her hips, helping her stand as she locks her arms around his neck.

“Is that what you had in mind?” Y/N asks teasingly as she looks up and meets his gaze.

“Kinda.” Dean dips his head and catches her lips, deepening the kiss with his tongue slipping inside her mouth.

“Dean,” she scolds him softly with blushed cheeks and a giggle that surely won’t keep him from doing shit. “There’s people here. Teenagers.”

“So? It’s nothing they wouldn’t do,” Dean remarks mischievously. “And no one’s here that we know. Claire’s caught us like a million times already, and Lisa doesn’t care. C’mon, we never get to do those things in public,” he appeals with a wiggle of his brows.

“Alright,” Y/N surrenders with a small sigh and a smile, tiptoeing up on one foot to press her soft lips back on his. She feels him breath into the kiss, cherishing every second of it. His hands wander from her hips to cup her cheeks, causing her to almost topple over as he forgets that he’s been steadying her. “Whoa, Dean!”

Her giggle interrupts the kiss as she tightens her grip around his neck before he moves his hands back to their place on her hips, offering her support again. She leans her head against his chest, and he rests his chin on her crown.

“Sorry, got carried away there for a moment,” he apologizes with a snicker, pecking the top of her head gently.

“Yeah, that happens with you sometimes,” she teases and buries her head deeper into his shirt. “Your heart’s beating really fast. Are you on something again?”

Dean wants to say it’s love, but that sounds too fucking cheesy.

“Nope, still clean,” he replies instead and doesn’t take offense in her question. “Just nerves, I guess. There’s something I wanna tell you,” he says and licks his lips, swallowing thickly.

Y/N looks up and finds his green eyes, her brow knitting in curiosity. But there’s a perceptive shimmer in her orbs, and Dean knows she can already anticipate what’s coming next. Judging by her shift in weight, he can tell she doesn’t want him to say it out loud.

“Shit, uhm…” She squeezes her eyes shut and fumbles for an excuse. Dean gives her a plethora of time to find a believable one. “I have to go. I promised the girls we’d work out a plot for the finale together tonight, celebrate our last week.”

Dean’s lips quiver but manage to find a smile. “You sure?”

Reluctantly, Y/N still nods and lets out a tense breath. “Yeah.”

It feels like dancing around a big, pink elephant between them. Both of them pretend it’s invisible, although it’s painfully not. It’s even roaring or hooting or whatever the fuck elephants do.

“Alright, I’ll drive you to the motel,” Dean capitulates with a resigned nod.

“No, uh, stay,” she tells him and clumsily hops back to the bleachers to grab her crutches. “I’ll get a cab. You should spend your night with Claire. Figure things out with Lisa.”

“Okay,” Dean caves once more but then grabs hold of her, pulling her to his lips. The kiss is fervent and heated and desperate. So fucking desperate. “One for the road,” he says with a painful smile as he draws back. He doesn’t want to admit that it might be the last one they have shared.

Y/N’s look tells him she feels the finality, too. It’s the epilogue of the best book he’s ever read. The end credits of his favorite movie. The final episode of a show he loved.

“I’m sorry,” she says quietly with a hesitant lip bite and a harrowing swallow.

“Don’t be. Have fun, okay? I’ll see you tomorrow,” Dean says and sends her one last weak smile before he watches her walk away with an aching heart.