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luci-in-trenchcoats · 7 months

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The Princess & The Playboy (Part 1)

Summary: After one of the reader's last concerts of the year, she unexpectedly runs into notorious playboy Dean Winchester, quarterback of the LA Wolves. Only Dean's a big fan and he seems to want more than just a photo if given the chance...

Masterlist

Pairing: NFL Quarterback!Dean x Pop Star!reader

Word Count: 4,400ish

Warnings: language, family trauma/angst, kidnapping

A/N: I promise there'll be more Dean and reader interacting in person next part! Needed to set the scene with this!

_________

You groaned the second you were alone. You’d survived the summer tour but you were exhausted. All you wanted was a greasy hamburger, chicken nuggets, and to sleep for a month. After changing into a pair of joggers and oversized hoodie, you texted your bodyguard Eric, telling him you wanted to get out of there quietly. He knocked twice on your dressing room door before entering with a smile.

“Great show tonight,” he said. You rolled your eyes, Eric grabbing your backpack for you.

“Like you pay attention to anything besides harassing the security team,” you said, resting your forehead against his strong chest. “I never want to tour again. I’m so tired.”

“You’re just cranky cause you’re hungry and need sleep,” he said rubbing your back. “You only have two more shows this year and then we can sit on the couch eating cookies and binging divorce court.”

“This is why I keep you around, buddy,” you laughed, taking a deep breathe before looking up. “Speaking of food-“

“Let’s get you out of here and full of some chicken nuggies.”

“Back in five,” you said to Eric thirty minutes later, your wallet in hand and panic button in your pocket. He let you go out without it sometimes but not after a show and especially not when you were in the press so much lately.

It was nearly midnight as you walked into the nearly empty McDonald’s, a guy in a hoodie at the counter with his back to you.

“Hi,” you said, stepping up to the other register. “Can I get a quarter pounder with cheese, a medium fry and a twenty piece chicken nugget with barbecue sauce? Oh and a bottle of water.”

You paid, the girl behind the counter staring at you like she recognized you but was too nervous to say anything.

“Holy shit,” said a male voice. You glanced left, the man in the hoodie pushing it down to reveal him in a black baseball cap. He was incredibly handsome and had such pretty green eyes. Something seemed vaguely familiar about him but you couldn’t place it. “You’re Y/N Y/L/N…and apparently you eat like a linebacker.”

“Dance on stage for three hours every night and you would too,” you said, the man humming.

“Do you mind if I get a pic?” he asked.

“Sure,” you said, the man handing his phone to the girl behind the counter who eagerly took a few. He was practically giddy when he got his phone back, a bag of food coming out for him.

“Thanks for indulging me,” he said. You noticed a few strands of confetti on top of his hat and smiled. He must have been at the concert. He almost walked away and out the door when he spun around, parting his lips. “Can I give you my number?”

“Sure,” you said again. It was much safer to just take the number and hand it off to Eric to do a background check on the person than try a rejection. The man scribbled it down on the back of your receipt, your cashier now acting as his wing woman and making sure he had a pen.

“I uh, hope to hear from you soon,” he said, flashing you a wink before leaving. You eased when he was gone, the girl at the counter handing you your bag of food after a moment.

“He’s so hot, isn’t he?” she said, your eyebrows raising. Not the reaction you were expecting from her.

“Mhm. Thanks for the food. Have a good night,” you said, quickly leaving. You ducked outside, Eric waiting in the backseat for you.

“Any trouble?” he asked, nodding to the man farther down the parking lot, slipping into a large SUV.

“Just a fan,” you said, handing him the paper with the guys number. He gave you a side eye as he took it from your fingers. “He was harmless.”

“I’ll check it out to be sure,” he grumbled, stealing a fry from your bag. “Did you get me-“

“Yes I got you your nuggets,” you said, Eric relaxing back into his seat. Your driver headed for home and in twenty minutes you were on your couch chowing down. Eric was at the kitchen counter, lazily scrolling through his phone, probably grateful that you were secure in the house for the night.

You watch his eyes go wide, gaze shooting to you.

“I swear I didn’t do anything.” You kept eating your burger, Eric silently watching you. “Dude, you’re freaking me out.”

“That fan from McDonald’s posted the pic of you,” he said. You rolled your eyes and got up, sulking over to him.

“Oh tell me he’s not some whack job.”

“He’s Dean Winchester,” he said, showing his phone to you. You shrugged, walking back to the couch. “Dean Winchester? NFL quarterback? Three time Super Bowl winner?”

You stared at him, Eric groaning.

“He’s the quarterback for the LA Wolves…he went to Kansas State the same time you did, Y/N. You probably went to his football games.” He rolled his eyes at you. “How do you not realize you’re taking a picture with a sports legend?”

“I must have missed it with all my free time over the past dozen years with all the touring and ten albums and other shit in my life. And frankly you’re the one that told me it doesn’t matter who it is, I need to be careful of everyone, whether they’re famous or not.” He sighed, putting his phone away.

“Alright, I get your point,” he said, returning to eating. “Dude’s kind of a player anyways it seems like. Nice guy but I know you’re more the sensitive guy type.”

“Emotionally available,” you corrected, plopping down on the couch once more. “Why would you think he’s into me anyways? Plenty of people are fans without wanting to get in my pants.”

“Well, it’s Dean Winchester so he definitely wants in your pants,” he joked. “Also the caption, genius.”

You quirked your eyebrow, Eric tossing his phone over to you. You pouted when you went back to the post, actually reading it this time.

DWinchester67 Y/N Y/L/N Saturday Night Concert at the Wolves stadium. AMAZING TIME with the crew. Worth getting ragged on by the boys all week for taking them to the show just to see them belt their hearts out to #FinishLine (video soon)

Then had the awesome luck to snag a pic with Y/N grabbing a midnight snack. I was dying on the inside at meeting my crush. Sorry for being awkward when you were trying to get your grub on. Next time it’s on me ;)

Your eyes met Eric’s when you finished, his chicken nuggets nearly gone.

“Yeah, like no reason he’s into you, right?” smirked Eric. You grumbled, returning to your late night dinner. “I’ll background check that number in the morning.”

“He’s a player that wants to have sex. Don’t bother with the background work. He’s harmless.”

“As you wish, princess,” he said with a little bow, earning himself being hit in the face with your balled up burger wrapper. “The abuse I put up with. Tsk tsk.”

“Yeah, yeah. Tell that to your generous benefits package,” you said, Eric chuckling as he double checked the back doors were locked one last time. “Eric…”

“Mhm,” he hummed, ruffling your head gently as he walked past the back of the couch. “See you in the morning, kiddo.”

“Night. Oh!” you said, sitting up on your knees on the couch, Eric throwing his head back. “It’s nothing bad! Just…can you ban everyone from the house until ten? I really want to sleep in and try to catch up.”

“You want me to fend off your team? After Dean Winchester posted that? What do I get out of this?” he teased, crossing his arms. You batted your eyes, jutting out your lip. “You got to do better than that.”

“I’ll buy you box seats to an LA Wolves game of your choice?” He looked blank faced which meant he was really tempted to take the offer. But Eric didn’t like extravagant gifts from you for doing his job. He already said his paycheck was more than enough and he barely accepted the Christmas and birthday presents you’d get for him.

You held up a finger, Eric calculating the move.

“Give me one good reason for not accepting.”

“First off, it’s too much. Second, I’m your primary protection agent and need to be available-”

“Please Eric? They’re going to be vultures in the morning with that whole post and you haven’t had a day off in six months. You’re as exhausted as I am. I’m asking as your friend, not your boss.” He grumbled, shaking his head. “Is that a yes?”

“It means I’ll think about it and I’ll see you in the morning,” he said. “We’re going to watch football all day. I’ll teach you all about it.”

You growled, Eric snickering the whole way out.

Dean POV

The first game of the season was always a good one. The team was healthy. We had home field advantage for once.

And I really enjoyed the hell out of playing football in a packed stadium. It wasn’t an ego thing like for some people. No, I loved putting on a show and entertaining people for a few hours a week, give them a fun escape before they had to return to the reality of their lives.

That’s what football had always been to me and I knew for most fans, it gave them that same sense of belonging.

And women tended to really like seeing a bunch of muscular men run around in tight pants.

“Winchester, surprised you’re here,” said Michael. I glanced over my shoulder in the locker room, a big smirk on his face. “I thought you’d be in the burn unit with how hard you crashed and burned with Y/N Y/L/N last night.”

I rolled my eyes at the taunts of the room, ignoring them as they riffed on me for a good ten minutes. When Benny walked in though they finally calmed down, Ben taking a seat in his cubby beside me.

“Let me have it,” I sighed. Benny leaned in close, covering his mouth from the rest of the room.

“If you really want that girl to go out with you, you got to do more than make an insta post. She’s classy. She’s not going to fawn over you like every dipshit you’ve dated because you’re good looking. So you better impress her.” He gave me one last look before reaching down to his duffel and pulling out his cleats.

He had a point. Y/N had never cared for cocky flirts. I could remember her in college, always spending time at parties with the shy academic guys that chatted her ear off about music theory and english papers. I swear the only time she gave a single jock attention was when she’d grab a guitar in the late hours of the night and sing a song none of us had heard before. She could stop a group of drunken college students in their tracks with a single note. Nowadays her music was all pop but back then, just her and a guitar…I’d have sworn an angel fell out of the sky straight in front of me.

No woman had made my heart swell up with comfort and longing the way she had the night I laid eyes on her for the first time.

The years had done little to diminish a teenage boy’s crush. If anything, seeing her last night, getting to talk to her for even a brief moment, made my insides burn hotter than before. Maybe it was only a crush, an infatuation with a beautiful woman with an even more beautiful voice.

I felt Benny’s stare on me as I lazily watched my feet before me.

“You’re still in love with her.” He said it as a statement so I didn’t respond. I’d never claimed such a thing despite Benny insisting on it back in college. But he’d always been good at sensing those kinds of things.

Or at least he wasn’t afraid to say it out loud.

“I talked to her in english lit once, about you.” My head snapped up, eyes wide as he was now down to his boxer briefs, tugging up his pants. “She heard what happened to Sam.”

“Why are you bringing up Sam?” I whispered, giving him a hard glare. Benny smiled, curious since he knew not to bring him up unless I did. “Half the school offered their condolences. Of course she-”

“She didn’t. She offered…hope. Apparently her little brother went missing once too.” I turned my head away.

“Everyone who knows anything about Y/N Y/L/N heard that story. Congrats. We both have little brothers that were kidnapped and never heard from again. Fucking awesome we can share that trauma,” I spit out. Benny leaned in close, gripping my shoulder.

“She wrote a song for her brother. Finish Line. She showed it to me long before she got famous. Look up who it’s fucking dedicated to and maybe realize there is a deeper reason why you fell in love at first sight with that girl. I have a feeling she’s the only girl in the world that could get you and you knew it long before your head did.”

I was seething, storming out of the locker room and into a trainers room next door, quickly shutting the door behind me. What the fuck was Benny thinking bringing Sam up right before a game? I could handle thinking about a girl but Sam?

I angrily typed Finish Line dedication into google, freezing at the short paragraph that appeared as the top result.

Chart topper Finish Line by Y/N Y/L/N was notoriously written by Y/L/N in her senior year of highschool after the disappearance of her younger brother, Max. Max is presumed to have been abducted while walking home from a friends house. The music video of Finish Line states the song is “For Max & Sam” although Y/L/N has never stated who Sam is. Fans theorize “Sam” is a representation of all abduction victims however…

I immediately tapped on the youtube video of the song, scrolling all the way to the end, bottom lip wobbling as I read the stark white letters against the black background.

She never gave me the time of day back then yet she knew who I was, what it felt like to have a piece of you go missing and you couldn’t do anything about it. She put my baby brother in a song for her baby brother and we weren’t even friends.

I swallowed thickly, forcing myself to calm down.

“Sammy,” I whispered, closing my eyes. “Is this a sign or something? Is she as fucked up as I am and the world doesn’t know it? Is that why she’s never been seen with a boyfriend her whole career? Did she shy away from connections when I buried myself in meaningless ones? Are we both so screwed up on the biggest stage in the world and that’s why I still feel breathless when I see her? Tell me I’m not crazy, Sammy. Tell me there’s a reason I’m still head over heels for this girl.”

I slowly opened my eyelids, staring at coach who was staring back at me on the other side of the room by the far entrance. I quickly cleared my throat and turned to leave, coach’s whistle stopping me in my tracks.

“I don’t know who the hell you’re talking about son, but my advice as someone who’s been married longer than you’ve been alive…you know when you fall in love. That’s the easy part. Admitting it and trying to get the balls to say it to her face is the harder part.”

“Sir, she doesn’t even know I exist. Or barely knows I do,” I said quietly. “I should-”

“Your little brother, god rest his soul, wants you to be happy, Winchester. So shoot your shot with this girl so you can stop having an existential crisis before my home opener, got it?” I glanced over my shoulder, coach’s face surprisingly soft for how close we were to game time. “She must be special to tame you.”

“She had me the whole time. The rest were me trying to forget.” He nodded, picking up his playbook again.

“Then go get this girl so you have your answer,” he said. “And stay out of my training room before games. Only place they can’t find me.”

“Yes sir.” I ducked back into the locker room, Benny gave me a raised eyebrow, silently asking if I was okay. I nodded and sat down to tie up my shoes, an idea sparking in my mind before I opened instagram. “Ben, take a picture of me.”

“Good god,” groaned Michael from my other side. “Like your insta doesn’t have enough shirtless selfies.”

He snagged my phone out of my hands, sighing as he took a photo of me smirking in my cubby.

“I regret being your friend,” he said, handing it back to me while Benny chuckled.

“Same, Michael,” I smiled back before I was on insta and typing furiously. I posted before I could stop myself, Benny and Michael sharing a look and immediately going to their own phones. But they weren’t fast enough apparently.

“Winchester are you serious?” shouted Gabe from across the room, the whole team looking at their phones now.

“Yup,” I said, standing and tugging on my under armor v-neck, my shoulder pads and then my jersey.

“You can’t force a girl to go out with you!” he shouted.

“I’m not forcing. I’m offering a donation to her charity if she does feel inclined to go out with me,” I said with a shrug. Benny grabbed my shoulders, looking at me like I was crazy.

“Five million dollars? That’s not what I mean when I said impress her you idiot!” he said.

“That’s what the picture was for,” I said with a wink, my phone already buzzing non-stop at the incoming flood of texts and calls. “You think she’ll take me up on my offer?”

“This fucker’s really about to get a fucking date with Y/N Y/L/N through a fucking bribe,” said Michael, shaking his head. “Dude, you’re crushing so hard it’s in psycho territory.”

“One date is all I want,” I said, smiling when coach walked in, rolling his eyes at me. “Come on boys, time to focus on the game!”

Y/N POV

I was currently hiding in my bedroom, reading a book on Sunday evening, Eric doing his best to get my agent and manager and PR head out of the house without force. As expected, they’d reemed my ass out for not capitalizing on the Dean Winchester picture in the moment but I didn’t care. I didn’t care about hanging out with pretty fuck boys for publicity’s sake.

But I had followed him on my private account no one knew about. It’d taken a moment but I remembered who Dean Winchester was in our college days. He was flirty back then I remembered. And a good football player I guess. But I just remembered what happened in the spring semester, how the whole campus knew his pain before he had a chance to even process it.

My heart ached for a boy I’d said nothing more than a passing hello to at parties.

I still felt that ache whenever I sang Finish Line. I’d never realized Dean went on to his own version of fame all those years ago. But I knew the hurt still existed in his heart. There was no healing it but some part of me wished I could soothe it for a moment. I forgot in the music sometimes. Maybe he could do the same when he played his games.

Maybe I really should have talked to him last night.

My phone buzzed and I saw a new post, this one of him making my jaw drop. “Hot damn you are good looking, Winchester.”

Then I shrieked when I looked at the caption.

DWinchester67 Hey @Y/NY/L/N it was fun running into you last night. How about you take me up on my offer and let me buy dinner for our first date?

Oh and to sweeten the deal, I’ll donate five million dollars to your charity if you say yes (plus another million for each touchdown I throw tonight, those are freebies for ya).

You got my number so waiting on you sweetheart. ;)

Eric was in the room before I could raise my head, eyes darting around the room before he determined there was no threat.

“Jesus, girl. I swear if you saw a bug-”

“Dean Winchester asked me out. Publicly.” Eric narrowed his eyes as he tucked his gun back into the holster.

“Okay…you made it clear to the team today you don’t want anything to do with a publicity stunt. What’s the problem?” You tossed the phone to the end of the bed, Eric sitting on the bench at the bottom to pick it up. He did a double take, eyes skirting to meet yours. “I’m doing a full background check on this man. He either really wants in your pants, to profit off you or he’s obsessive. To be honest, I don’t like any of those options.”

“Me either but five million dollars to the charity? Plus more? That could help kids, Eric. We could find a safe way to do this, right?” He pursed his lips, nodding once.

“One date at a place of my choosing. My team will be there in the background and I’m going to talk to this boy and let him know all of the ways I can kill him if he tries anything.” You smiled, Eric handing the phone back.

“You’d kill your favorite football player for me. You’re too sweet Eric,” you chuckled. He stood up, adjusting his sports blazer.

“You know why I stuck with you when my agency assigned me to the Princess?” he asked, a dry laugh leaving his lips. “You always listened to me. You didn’t always agree but you listened and we could have conversations. We could have conversations about safety without you acting like a brat or me like an asshole. You respected me and that earned you loyalty all these years later.”

You stared your hands in your lap. “My parents lost one child. I don’t want them to lose another.”

You were surprised to find him come closer, sitting on the edge of the bed, turning to face you. He tucked your hair behind your ear, smiling softly.

“Don’t lose hope now, kiddo. I’ve always admired that about you.” You looked away, Eric stroking your cheek with his thumb. “Someday we’ll find the truth. I promise.”

“My mom wishes it were me,” you said, shaking your head. “If I didn’t make my parents so much money I’d think they’d be plenty happy to let some crazy fan take me away forever. All because I was five minutes late to pick up Max and he decided to walk home.”

“Hey!” Eric gripped your shoulders hard, hard enough that you felt the strength of his hands down in your bones. He was always so gentle you with guiding touches here and there you often forgot he was as deadly with his hands as he was a weapon.

You met his gaze, Eric sighing.

“That is not true and you know it.” His stern expression softened when you shook your head.

“She told me the day we had a funeral for him Max should have been there and I should have been the one missing. So I know, Eric.” He pulled you into a hug, letting you squeeze him tight.

“I know she did,” he whispered, your chin resting on his shoulder. “She has so many regrets from that time and knows what she said broke something with the two of you. But I have had countless conversations with them over the years. I know you trust me so trust me when I say, you are their world and it would destroy them to lose you. She always asks me if you’re happy because she says you put on your fake smile for her. She doesn’t blame you one bit for it.”

“I hate when you have points,” you said, closing your eyes, getting another squeeze from him.

“Happy to help my buddy. So you don’t give up on Max yet, alright? Everyone else has. If he’s out there, he needs you to keep going for him.”

“No wonder your team adores you. Soft cuddly bear under all the threats of violence aren’t you?”

“It’s how I land so many chicks,” he chuckled. He kissed your temple and stood, cracking his back. “Respond back yes if you want to. Let me look into this Dean Winchester before you agree to anything else though.”

You hummed, clearing your throat when Eric was in the doorframe. “I-I do remember one thing about Dean in college. He had a younger brother Sam that went missing too. Never found him.”

Eric kept his back to you for a beat, nodding once.

“Do you think Dean is a bad guy?”

“Gut check says no. Probably just wants a hookup,” he said before stepping out and pulling the door shut fast behind him. “Rowan, I swear to god you bother this girl tonight and I’ll shove my glock up your ass.”

“He asked her out! I need to talk to her!” he yelled back on the other side of the door. You sighed and put on your noise canceling headphones before going to instagram and tapping on his post.

Y/NY/L/N @DWinchester67 One date. As friends Winchester

Not five seconds later you received a winking emoji and “friends” in response.

“Dear god, you’re going to be a handful, Winchester.”

________

A/N: Read Part 2 here!

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