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Dean Winchester was going to be the death of me. Not metaphorically either I mean quite figuratively as it’s four thirty in the morning and instead of sleeping I’m being driven to the jail to pull boss out of jail for a drunken brawl. Crowley, his publicist, had already been alerted thankfully and Benny, his driver, had picked me up without such much as a word other than buckle up.
“Benny, I’ll meet Cas up front but can you pull around back? I’m going to try to get him out without paparazzi if I can,” I request and Benny nods pulling up as Cas opens the door helping me out. I wrap my sweater around me as Cas gets me in through the throng of reporters.
“I’m sorry Y/N. He wouldn’t listen to me. I swear I turned to piss for one minute and come back and he’s swinging. Some bodyguard I am,” Cas huffs helping me into the police station.
“You’re a great bodyguard, Castiel. Dean could start a fight in a prayer circle and at least you saved him from getting hurt. Any idea what the fight was over or with whom?”
Cas chuckles pulling out his phone, “I just know it’s that wannabe Cole Trenton. I’m not sure what caused it, but I’m fairly certain Dean has ruined headshots for him for a while.” Cas passes me the phone with pictures of Cole bloodied and most definitely a broken nose. I know I should be mad at Dean for fighting but this is Cole. Cole was creepy and had been forward on more than one occasion.
“Well, he couldn’t have happened to a nicer fellow but let’s get our boy home,” I sighed as we made our way to the counter.
“Your boy, maybe,” Cas raised his eyebrow at me and I bumped his shoulder. “You ever going to tell him?”
“Don’t know what you’re talking about Cas,” I do know what he’s talking about and it’s the last time I play truth or dare while drinking tequila. Okay, so besides being a huge pain in my ass I’m stupidly in love with my boss. Dean’s a good guy though. Maybe likes to party too much but otherwise you couldn’t meet a better person. Or funnier, cuter, knows every line to Star Wars, and is actually really handy.
“Y/N Y/L/N!” an officer shouts not a moment too soon as Cas gives me the eye like he knows all. It’s not childish to stick your tongue out in the middle of a police station.
I hand the officer my ID and he nods with a sigh, “He’s been asking for you since they locked him up.”
“So he’s been a handful?”
“Basically ma’am,” the officer leads me back through the halls to the door that led to the cells. Cas left to meet up with Benny and make sure our getaway was clear so I was about to have a handful of drunk Dean Winchester. “Right through here ma’am another officer will escort you to Mr. Winchester. Good luck.”
“Thanks,” the second officer led me down the hall but I didn’t need him too. Dean’s badly off-key rendition of I’m Too Sexy rings through the cement halls. I’m going to need a raise after all of this. The officer motions me on and states he’ll return with Dean’s paperwork and belongings. I took a breath rounding the corner as Dean continued singing to the amusement of the few others in the cells around him.
“Y/N! Y/N! There she is! My beautiful assistant! I didn’t think you’d come, Sweetheart,” Dean’s eyes are dazed from the alcohol as he leans against the cell with a grin.
“I didn’t want to Dean. It’s four thirty in the morning and I do require a few hours of sleep. Cas could have brought you home without me or with Crowley having to know until the morning but now here we are.”
“But Sweetheart, Cas isn’t as pretty as you are,” Dean smirked trying I suppose to suggestively wiggle his eyebrows.
I rolled my eyes as the officer returned handing me Dean’s things, “You sure that I can’t leave him here, officer?”
The officer laughed, “Sorry he’s officially all yours now.” The officer unlocked the door and Dean stumbled out before pulling me into a tight hug. Although usually, I enjoyed his hugs Dean reeked of alcohol enough that I felt nauseous. I managed to pull his arm around my shoulder as I led him back to the hallway and the first officer directed us to the exit where Cas and Benny were waiting. Thankfully, Cas and Benny took Dean from me pretty much shoving him into the SUV.
“Y/N, you want me to drop you off at home, chere?” Benny asked holding the door open for me.
“Thanks, Benny but there’s really no point. With all the damage control Crowley will want me there anyway. I’ll catch a nap on his couch. It wouldn’t be the first time and I dare hope it will be the last,” I squeeze Benny’s hand then slide in next to Dean.
Benny and Cas share a knowing look before Benny shakes his head closing the door. I hope that’s the end of it because I’m too tired to argue. Dean leans over letting his head rest on my shoulder as I sit back in the seat. Cas though doesn’t plan to remain quiet as he takes the passenger seat, “Y/N, you can’t keep running yourself down like this. You’re young and you should have a life beyond work.”
“He’s right Y/N,” Dean mumbles into my hair. “You work too hard.” I glare down at Dean but he only snuggles in closer and I give up. Yeah, he will definitely be the death of me.
The smell of robust coffee under my nose wakes me from my light sleep on Dean’s couch. With a squint, I open my eyes to see Dean sitting on the coffee table waving the coffee cup in front of me, “Rise and shine Princess. Crowley will be here soon.”
“Crap,” I groan forcing myself to sit up as Dean hands me my glasses. “What time is it?”
“Nine thirty-ish,” Dean hands the coffee over and surprisingly he made it just like I like, sweet, creamy, and able to keep me up all night. I look Dean over and marvel at the fact that a few hours ago he was in a drunken brawl and now he looks like he’s had the best sleep of his life. He’s freshly showered, clear eyed, and he’s wearing that cologne that reminds me of the Yankee candle I keep at my place. It’s moments like this that I love being so close to Dean. He’s really beautiful, “You know staring is considered rude.”
Then there is that cocky asshole I love so much, “Why don’t you look like shit?”
“I’m too beautiful,” he jokes nudging my foot with his. “Thanks again for coming to get my drunk ass. I should’ve listened to Cas, but I couldn’t help myself. Sorry, it was so early.”
“What happened, Dean? I know Cole’s a grade A prick but we’re trying to keep you out of the tabloids. Marvel isn’t going to like this kind of coverage.”
“Hey, Clint Barton would have punched Cole if he heard all the shit he was spouting last night. Hell, Marvel will probably be like hey that’s a great casting decision. He is his character,” Dean mocks before standing and moving to the kitchen.
I follow him of course because I need to know, “Dean, stop dancing around the issue. What did Cole do to provoke you? I shall the pictures from Cas and he was messed up.”
Dean’s braced himself on the counter looking down to avoid making eye contact with me, “He was talking shit Y/N and I wasn’t going to listen to it. Just let it go!”
“Fine don’t tell me Dean but you need to tell Crowley when he gets here,” I take a sip of my coffee climbing onto one of the stools.
“He was talking about you Y/N. He called you a whore and said a whole bunch of shitty things about you and how you look. It was uncalled for. I don’t care what he thinks about me but you don’t deserve that. You’re the nicest person I know and he wasn’t going to say that stuff about you.”
I don’t know how to respond but my heart does this weird flutter. He’s my boss. He had to defend my honor and I don’t need to make a big deal out of it. Instead of saying anything I climb off the stool and walk around pulling him into a hug, “Thank you, Dean. Cole always gave me the creeps anyway.”
Dean wraps his arms around me, “Well, now he knows better. Thanks, Y/N.”
“Sorry to interrupt the love fest but there is the matter of your career and controlling the damage, Dean,” Crowley’s voice echoes forcing me out of Dean’s arms. As soon as we separate Crowley thrusts a list of errands in my hand and once again it’s all business. Never a boring day in Casa da Winchester.
Thankfully, Marvel accepts Dean’s explanation and as he said they said it was exactly what they were looking for and Dean is cast as Hawkeye for the Marvel universe. I couldn’t be happier because I know Dean will do a great job and now I get the pleasure of hanging out on set. The weeks leading up to filming are stressful but it’s going to be worth it as I continuously remind Dean. Today’s his first scenes in the actual suit and I’m waiting patiently to see. He promised I could see first.
“Come on Birdboy! They are going to be here any second and I want to ogle you, sir!”
“Hold your horses,” he shouts before the door to the room opens and he steps into the living area. I bite my lip as my eyes trace his frame. Dean had hit the gym like no one’s business to fill in the suit and it is not disappointing. He looks beyond amazing and I feel those butterflies again that I plan to ignore.
“Dean you look incredible,” I smile looking him over as I blush unable to stop myself.
“So, hey, I wanted to ask you a question,” Dean suddenly gets serious as he leans against the counter looking down at me.
“I’m intrigued,” I close the laptop where I was working on Dean’s social media presence giving him my complete attention.
“So, you’ve been with me for what three years now?”
“Yeah, I think so.”
“Okay, well you’ve been with me through my relationships and all that and where I messed up and how I can be better.”
“I was there for Jo and Lisa, Dean. Come on just ask me,” I’m not sure where he’s going but I’m really getting concerned.
“Well, do you know Jessica? She’s Scarlett’s stunt double who had lunch with us last week?”
I swallow nodding. Jessica’s beautiful and I knew she’d been flirting with Dean but I didn’t think he’d been perceptive of it. I’m starting to get that I was wrong. “Yeah, she’s great!”
“Yeah, I just feel really connected to her and I think there’s a future there, but with my track record, I’m scared. I don’t do feelings and my past relationships have failed, but I think there is something here. I need your advice Y/N. You’re one of the few people I trust and I feel like I can talk to.”
My head screams at me to tell Dean that he should give me a chance, but I can’t. Dean doesn’t feel that way and it’s wrong of me to try to force that on him. He’s my boss and I’m his assistant. I sigh as he looks to me and I already regret what I’m about to say, “I think if you feel so strongly that you’re coming to me. I think that means you should go for it. Now, you could get your heart broken or you could have the greatest love affair the world has ever known, but you’re not going to know unless you try.”
The smile that Dean gives me breaks my heart and then he leans over kissing my forehead. Thankfully, they come to get him for his scene leaving me time to decompress. I’m such an idiot. I leave Dean a note about running some errands and head out to clear my head. I knew when I first realized it that I could never have Dean, but I didn’t expect to be the one who gave him advice leading him to someone else. I decide to head back to the hotel texting Dean and Cas that I’m not feeling well. I snagged a joint off one of the crew so I should be able to get a nice buzz and just sleep for a bit. I set my phone to silent and kick back on the bed throwing open the balcony doors smoking away all the things I’m feeling. I can do this. I can be a grown up and do my job without letting my heart get in the way.
After that night I make a rule to keep things a lot more professional with Dean. I keep set work hours, never staying over or coming early, no more sleepovers on his couch, and while on set I only address him as Mr. Winchester. Cas questions my new work ethic but I wave him off unable to answer his questions. As for Dean, he senses the change in the mood but does nothing to try to talk with me about what’s going on. He has lunch with Jessica on and off but I make sure to eat with the crew members if I can manage to eat at all. Jessica herself has never been nicer. Her pretty blonde wavy hair and sweet personality make it really hard to hate her, which I don’t hate her. If anything I’m jealous of her. I can see how Dean would fall for after knowing her only briefly. She and Dean have a lot in common that way. Falling for him had been effortless and unexpected and I imagine that’s how Dean felt about Jessica.
“You okay?” I look up as Cas takes a seat next to me passing me a beer. It’s late and Dean’s hosting his own wrap party with the cast. It would look bad if I didn’t attend so I bought a new summer dress and made myself available, if only for a little while.
“Yeah, just a little tired. I’ll be heading out soon I only agreed to stay until ten,” I offer taking a sip from the beer Cas gave me.
“It’s been a weird couple of months. You finally ready to talk about whatever is bugging you?”
“Cas, I’m fine. I’m just trying to be a little more professional. It’s working for the best. I finally have some resemblance of a home life, Dean’s staying out of trouble, and by now I’m pretty sure he and Jessica will be moving in together anytime.”
Cas spits out his beer with a chuckle, “What’s that about Dean and Jessica moving in?”
“Dean has a thing for her. He asked me what he should do about it when he first started filming and they’ve hanging out on set a lot. It makes sense and it’s been keeping him out of trouble. It’s good I’m sure they’ll make each other happy.” It’s the same mantra I’ve been repeating to myself for weeks.
“Jessica? You mean Jessica Moore?” Cas looks at me incredulously.
“Yes, Cas, Jessica, Scarlett’s stunt double,” I growl as Cas erupts in full body chuckles before taking another drink from his beer. “What the hell is so funny?”
“I don’t know what Dean told you but I can guarantee it isn’t what you think. Jessica is dating Dean’s brother Sam. They’ve been together for almost two years and Dean helped her get the job as Scarlett’s double. You’ve met Sam before.”
“Obviously, but this doesn’t make any sense,” I’d met Sam before and he did mention his significant other Jess but I’d never met her when Sam did visit. But why would Dean ask me about her then? Maybe he felt guilt over crushing on his brother’s girlfriend. “I mean Jessica has never mentioned Sam to me.”
“Probably because you actively avoid her Y/N,” Cas chastised and he wasn’t wrong.
“Then why would Dean ask me about it? Or how he had feelings for her but didn’t want to screw it up? Maybe he just feels bad because it’s Sam’s girlfriend. We can’t help who we love,” I swallow down the beer handing him the bottle. “I’m just going to go Cas. I think I’ve had all the fun I can manage.” I don’t know why I’m mad at Cas, maybe madder that instead of falling for me Dean fell for his little brother’s girlfriend, which shouldn’t surprise me. I guess it doesn’t just hurts more than anything.
Before Cas can speak I turn and make my way back to the house where I run right into Sam and Jess. Their hands entwined, “Hey Y/N!” Sam speaks cheerfully, “So how’s your summer been looking over my two loons?”
Fake it ‘til you make it, right? I smile, “It’s been a great summer. Jessica and Dean have been on their best behavior.”
“You wouldn’t talk to us if we misbehaved,” Dean’s voice from behind makes me jump. “We’d be lost without her.” Dean throws his arm around my shoulders and I think it’s the first time he’s been this close in months.
“Yeah I wanted to get some more girl time in with you, Y/N, but you were always so busy. You need a vacation,” Jessica chuckled looking over at Sam. “Sam’s taking us for a mini vacation once he’s done with the case he’s working on.”
“That’s great Jess. Maybe we can get together when you get back,” I offer out of politeness mostly. Dean’s arm on my shoulder feels so heavy. I just want to go home and curl up with Ben & Jerry’s and call it a day.
“I’d absolutely love that. Maybe we could go on a double date sometime? I know this great place that would give us our own privacy,” Jessica continues talking as Sam smiles down at her and I feel like I’m going to vomit. Does she know Dean’s in love with her? Are they seeing each other behind Sam’s back?
“Actually if you guys would excuse us I need to talk to Y/N about something in private,” Dean speaks up as Jessica and Sam share a knowing smile before walking away as I allow Dean to steer my back into the house. Dean leads me past the guests and up the stairs before opening his bedroom door. “It’s okay I just want to talk for a second.”
Dean closes the door and I sit down on the edge of his bed. Of course, it’s a memory foam mattress and I sigh with how comfortable it is. Dean seems suddenly nervous as he walks back and forth, “Dean, just spit it out. My days almost done and I want to go home.”
“Why have you been avoiding me?” Dean spits it out stopping his arms crossed in front of my chest.
“Dean? I work for you. It would be kind of hard to avoid you. I’m just trying to be more professional,” I take a breath. “Plus if you’re in love with your brother’s girlfriend I want no part of that. I never would have told you to go for it if I had known it was Sam’s girlfriend.”
Dean swallows and walks over sitting beside me. Silence hangs in the air until his hand lands on my thigh turned up. I know I should just leave but I put my hand into his as he deflates, “That’s not what that was, Y/N.”
“Then what was it, Dean?”
Dean groans, “I wasn’t asking about talking to Jessica. I was asking about you.”
I turn looking at him wide eyed in confusion, “Me?”
“Yeah, I’m kind of totally smitten with you. That’s why my relationships with Lisa and Jo didn’t work out. I think they knew before I did. Well, I know for sure Lisa did,” he admits with a chuckle.
“Dean, please,” my heart is pounding because this stuff only happens in the movies. It doesn’t happen in real life and it certainly doesn’t happen to me. “Please don’t be messing with me.”
He smirks before his free hand is caressing my face. I can’t respond as his lips are pressed to mine and I got to say it’s better than I ever imagined. He’s gentle and there is a slight hint of mint as his lips part. This is actually happening. I’m finally kissing Dean and he’s kissing me. I pull back placing my hands on his chest. I suck in a deep breath and exhale trying to accept what is happening, “Y/N?”
“So, you’ve been in love with me this whole time? Why the hell didn’t you ask me sooner why I was being distant?”
“Well, I actually thought you knew Jess was Sam’s girlfriend and you just needed time to figure out I was talking about you. Then it just seemed like it was taking forever so I asked Sam and he laughed because he told me he’d never introduced you to Jess. So I realized I was an idiot and that once you found out about her you’d think I was a shitty brother. I had this whole elaborate plan to tell you tonight after the party. When I saw you in that dress I just needed you to know right now.”
I laugh because it’s so ridiculous and so Dean that I don’t know why I ever thought he was smooth. I reach up pulling him into a kiss as a look of hurt crosses his face, “You literally turned your own life into a romantic comedy Dean. I mean a convoluted declaration of love, misinformation, and you spill your feelings. I’m going to have to write this all down one day.”
Dean flicks my nose as I collapse on his bed in giggles, “Oh that’s it, Sweetheart! You are going down!” Suddenly Dean is hovering over me tickling my sides in every place that makes me squeal. There’s no fighting him off before he’s straddling me looking down. He slows and suddenly the playfulness slips from his eyes to something darker. I already feel his stiffening arousal so I rock my hips up into his as he hisses then warns, “Don’t start something you can’t finish, Princess!”
“Wasn’t going to Hawkeye,” I sit up already deciding I want this to happen before I quickly undo his belt. “Think you can keep up with me?” I bite my lip as I pull the belt from his jeans tossing it across the room.
“Oh Y/N,” Dean grins leaning down pressing me back into the mattress. “You shouldn’t have said that. Challenge accepted.”
Needless to say, Dean makes extremely good on my challenge. After losing track of how many times we made each other come apart we fall asleep cuddled up. Dean throws the covers over us kissing my forehead before I bury my head into his chest. I look up as the light catches a smirk on his lips before he cuts it off.
I don’t know what’s going to happen when we wake up tomorrow but I do know two things. One, Julia Roberts can suck it this is the best movie I’ve ever seen. And two, Dean Winchester will very much be the death of me. I’m totally okay with it, “Love you, Dean.”
I can feel Dean smile against my forehead, “I love you, too.”