#deanwandamons3Kfollowerschallenge

[kickingitwithkirk]

Mascara and Masquerade

Summary: Jensen gets a new celebrity assistant who’s not what she appears to be

Pairing: Jensen Ackles x Reader

Word Count: 3896

Warnings: cursing, family issues, age differences, deception/hiding the truth, some angst, sexual fantasy, male masturbation, sex toy, loss of a child

A/N: for @deanwanddamons #deanwandamons3Kfollowerschallenge

A/N II: story set season 13 and told POV of Jensen and Reader and if it seems kinda crazy, it’s the characters acting outta character due to past experiences

Prompts: Secret Dating, “Did you just tell that person I was gonna ask out that we’re dating?” Third Wheel-Protective Best Friend

Squares Filled: @anyfandomgoesbingo -Escort AU @spnkinkbingo -DDLG @j3bingo -”Did you just tell that person I was gonna ask out that we’re dating?” @spnmixedbingo -Amnesia @spnaubingo - Demigod AU

Vancouver 

July 24th

~You~

“May I see your ID?” 

I hand my driver's license and temp pass out the car window to the guard, checking it against their paperwork and handing it back telling me how to get to administration to acquire my permanent credentials.

Even though I come in an extra hour early, some mixup delays me and when I finally reach the lot I am greeted by a harassed gopher grumbling at how late I am. 

Since they weren’t who I was working for, I didn’t bother to explain what happened and grab my work bag to follow as they gave me a quick tour before heading into the soundstage.

I’ve worked on several shows over the last four years but this was the first time a set had struck me dumb in amazement.

TV screens don't do justice to the attention to detail that had gone into the construction of The Bunker, briefly reminding me of classic movies where the builders meticulously created intricate woodwork and set designers used sumptuous material and antiques to create ambiance.

My escort showed me an innocuous corner to wait in until they were finished with the current scene and I watch amazed, as always, how actors can slip in/out of their characters. 

After checking the playback and being satisfied the director called for the next scene's setup the gopher approached one of the actors and said something pointed toward me and they turned, eyes me then frowned. 

Terrific start.

I squared my shoulders before walking over to introduce myself to the man whose life I’d been hired to, well, basically run. “I apologize for being delayed sir,” their eyebrows went up, “administration hadn’t received my visa credentials and took a while to sort out.”

“I’m not that formal so call me by my first name..”

“..it would be unprofessional Mr. Ackles.”

~Jensen~ 

It’d been a good day without Misha here distracting us, aka Jared, and looking like we’re getting done ahead of schedule when one of the gophers told me my new assistant had finally shown up, only three hours late, and when I see the person sent I’m disappointed, having requested a guy or older woman with industry experience. 

Instead, they’ve sent some dowdy looking, just knows gonna be wet behind the ears twenty-something. 

For a split second the way she walks reminds me of Jared, must have something to do with her height when she started apologizing. 

Someone raised her with manners but I’m less than thrilled when she calls me sir, last thing I want is to be reminded that I’m edging forty, saying it’s unprofessional to call me by my first name. 

“Where the hell did you come from..nineteen-fifty?”

“Texas actually.”

“Huh, don’t sound like it, where ‘bouts?”

She shrugged “just ‘bouts. I spent several years outta state for school, guess it eradicated my accent.”

Wasn’t sure what to make of the dodge but let it go, noticing some eavesdroppers, “it’s gonna be a bit till they’re done setting up so let’s head somewhere less noisy to finish this discussion.” 

Grabbing a cart I drive us to my trailer and held the door like the gentleman my mama raised me gesturing for her to proceed, “thank you si..Mr. Ackles.”

Deciding I’d better stay clear-headed so I don’t say something stupid pull a couple of bottles of water and hand her one before settling in the recliner, “I’m sorry but you’re not gonna do..” I trailed off when she slightly squinted and her forehead wrinkled. 

Huh, now she’s giving me Sam.

“Why not?”

“I asked for someone with experience, the last two were so young they couldn’t find their own asses let alone keep my shit in line.”

“I happen to know where my ass is and very experienced at keeping other people's shit in line.” 

She fished around in this ridiculous oversized bag she’s been toting hands over a few printouts for me to read. 

Y/N Y/L/N, graduated Magma Cum Ludi while working as Sterling K. Brown's celebrity assistant. Been hearing nothing but good things about his new show and interesting, even Milo gave her a recommendation.

“I’ll admit your credentials are impressive, obtaining a bachelor's degree while working the batshit crazy hours this industry runs on but I gotta ask, why’d you request a transfer? Sterling’s a good guy to work for.”

“I liked working for him but didn’t cotton to the LA bullshit. I thought about Georgia or New York, but neither suited me, Van has a more of the right vibe and people are nicer here.”

A straight shooter, I liked that. 

“I must be a glutton for punishment,” point a stern finger at her, “you're on probation ‘cause I’ve been burned by people your age young lady, so if you fucking flake on me..”

“..you’ll kick my ass all the way back to Texas?” 

“Damn straight,” someone knocks on the door yelling I’m needed back on set. “Come on, I’ll introduce you to Jared’s assistant, they can show you how to keep and coordinate our schedules. Now for some ground rules, you're gonna want to write these down.”

“I have an excellent memory.”

“Uh huh,” I mutter heading out the door and getting in the cart, “it's Jensen, my dad is sir. I expect you to be available at all times so if you’ve got something, let me know.”

I weave around an offloading truck, “be here by 6:30 and it's no secret I’m not a morning person so don’t try going over anything until I’ve had my coffee, black and strong and I’ll grab something from craft services.”

Parking near the set entrance we walk few steps and appraise her again in in the daylight. One things for sure, she’s as plain a Jobs ass behind those humongous spectacles, definitely no temptation there so I won’t have to worry about being in the shitter with HR.

“You’ve gotta get a different wardrobe,” she stopped with a questioning expression and I pointedly peer down frowning, “that outfit might be fine for some bumfuck lawyers office but here it’s long days so jeans, sneakers, or boots depending on the weather. When we’re doing public events wear a nice jacket. Entienda?”

Shifting that godawful bag held out her hand, “Sí, but I’m still gonna call you Mr. Ackles, otherwise it’d be impertinent. ¿Lo entiendes?”

I took her hand and we both got zapped, the kind you get when shuffling across carpeting then touching metal, and Y/N quirks a peculiar smile.

What the fuck about you keeps reminding me of Jared? 

I quickly plastered a pleasant smile on, “one week only kid, should give us time to get comfortable with each other.”

We head inside as I shook out my hand, perplexed. 

Gotta a feeling you're gonna be more than I’ve bargained for.

~You~

October 9th

Rogers Stadium 

How the hell did I get roped into this? I don’t even like baseball! 

I’ve done support for other charity events the show does but participate? Yet here I am, sitting in the dugout watching the casts practice session.

Truth be told, I’ve been watching my boss work up a sweat, I’m so not into the whole moist look on guys, on most it’s icky but what the fuuuck, does nothing look bad on Jensen?

He’s practically glistening under the stadium's lighting, even the damp bits of his hair are sexily sticky and feel a throbbing between my legs drop my head into my hands groan in frustration cause falling for my boss wasn’t part of the plan!

“Hey,” I peek and he’s close enough to see sweat gliding over his skin. “Yeah,” I squeak made his eyebrows shot up in surprise chucks a thumb at home plate, “your turn.” 

“Oh, I uhh, I don’t,” bat swinging gestured. That’s not a total lie, my brothers taught me how to hit a ball.

Okay, it was a kid’s plastic set and I was four but still, it counts. 

Jensen gives me annoyed Dean, “you’ve gotten off..”if you only knew how bad I need to, “..so get your butt out here young lady.” I obediently follow him off to the side and pick up a practice bat, “you know which end to grip?” 

 “I’m not Aunt Bea, thank you very much,” I groused making him laugh took my stance, “thought you said nobody likes a smartass.”

 “Depends how nice the ass is,” he snarked, stepping behind me places a hand on my hip, “widen your stance.”

Shifting made my ass bump against his crotch, hello Mr. Chub, can’t resist wiggling my money against him, “like this?” 

Jensens grip tightened and breath hitches before speaking in Dean’s roughened voice, “I’m gonna pitch a few so keep your eye on the balls.”

“Oh, I know how to keep my eye on your balls,” I innocently tease, then spot Jared not only watching us but overhearing flirty comeback tensed and pointedly throwing bitchface at me.

Foul ball

#SPNNOLA

October 29th

“Excuse us,” Jensen firmly gripped my bicep hauling me off the barstool marching us towards the back door.

Once we’re outside he slams it shut and shoving me against it leans in so close I can smell the bourbon he’s been enbidding, ”did you just tell that person I was gonna ask out that we’re dating?” 

“I was saving you from you, you jerk,” and before I can continue his expression grows dark. 

Fuuuck, if Jensen had channeled that into Demon Dean found myself almost acting like Pavlov's dog. Every time he drops into his dominant persona, its becoming harder to resist dropping into my little subspace and calling him daddy.

“Look, I get you're jonesing for some sushi but keeping your shit in line is my job so I’m now advising you not to fuck around with a swindel cat.”

“A What!”

“That person fucks people while secretly filming them then hands the vid to a shady distributor who’s gonna release it unless you cough up some cheddar,”  Jensen’s mouth dropped open, “your welcome.”

I grabbed his wrist checking the time, “let’s head over to Daisy Duke's, I got a sudden craving for biscuits and sausage gravy with a side of greasy breakfast and pot of coffee for you, last days in five hours.”

~Jensen~

I shut the door leaning back against it grateful this weekend has come to a close. 

Never in a million would’ve I imagined having my ass jam scammed let alone saved by my twenty-something assistant who persistently tails me when cruising bars on con weekends. 

What a pathetic piece of sh..divorcé..I’ve become.

On the way to shower I caught my reflection in the mirror stare at the leaner, tired face reflected back. Logically, I knew it was from getting older and not having a lotta time to work out more than to maintain these days turned my back to it and strip.

Walking outta the bath naked vigorously towel-dry my short hair and grabbed a pair of boxer briefs spot a box lying on the bed that wasn’t there when I came in. 

Opening its flaps find a Fleshlight Turbo Thrust Blowjob Masturbator nestled inside start devising pay back on the fucker pranking me, figuring it’s Jared or his new cohort Alex spot a handwritten note.

Wait, that’s my mousy, irritatingly persistent assistant Y/N’s handwriting, the person responsible for my balls being backed up from not getting any in weeks has wrote something I’d expect to find in penthouse forum.

Once again, I’m wondering if she’s taken her job of handling my shit a little too personally.

Fuck it.

I grab a couple of pillows to pad the headboard and grab the toy and lube outta the box squirt a generous amount in its opening and coat its outer lips start teasing my cockhead watch it swallow my shaft and, adjusting it tighter, start working it up and down.

Damn, does it feel good.

“Mmmm, that’s it, feels good but you can take more.. you look beautiful, mouth all stretched out taken daddy’s fat cock..suck harder..yeah, just like that..fuck little girl, you should see how my cocks bulging out your throat..oh shit gonna cum..fuuuck Y/N!”

Flight to Vancouver 

Without Jared, who detoured home, to keep me distracted chattering on about whatever his nerd brain was into at the moment because mine won’t stop replaying that fucked up fantasy I had starring Y/N again found myself trying to sort out what the hell going on with these fucked up feelings I keep having about her. 

Been a long time since I’ve met someone I’ve wanted an alternative relationship with impulsively pick up my phone.

>Hey, hadn’t👂from 🫵 miss the 🛩 

<tickling my 😆 🦴smartass, on ✈️ with 🫵

>don’t 👀 🫵

<;in coach ☹️

>I’m 😑 

<Ahh poor baby, stuck in🥇class while I’m smooshed like 🥫🍣  I’m 😫 ❄️ 

I chuckled at her sarcasm:

>need to 💬 about that 🔞🎁 

<did you👍 or to much a gentleman to 💋&🗣 

> 🦗🦗🦗 

< 😆 knew it’d 💡your 🧨 did your🕹💥

>I find that❓inappropriate young lady😡

&lt;I’m not sorry daddy😏

Switching off my phone glanced around before reaching down to adjust my chub and thunk my head against the seat back. 

So not how I wanted that to go.

Three days till Thanksgiving 

Jared bound into my trailer noticed my mood, “hey, what’s up?”

“My dog walker called,” the door opens and Y/N came in carrying some drycleaning gave Jared a tight smile.

For some unfathomable reason, she’s being more wary of him and he’s been acting weird since the charity baseball game last month.

Hell, maybe she has a crush on him and he knows so why does that thought give me acid burn?

“They've got a family emergency. Fuck, I didn’t wanna fly Icarus since he just had surgery but Mama insisted I be there, said all the families coming this year.”

“So what’s the excuse gonna be when the lady you're,” he does those finger quotes, “secretly dating doesn’t show again?” Y/N makes this weird face at his question.

“I’ll think of something.”

“I’ll take Icarus.” she offers and swear I can hear Jared’s gears grinding, “if you're worried about the cost, you’re welcome to fly with us, getcha as far as Austin.”

“Mr. Padalecki,”  her response is polite feel the temp figuratively drop, “I appreciate the offer but no thanks,” he starts to speak again, “my showing up for anything has never gone over well with my siblings. I’ll drop by for him tomorrow,” curtly nodding to Jared she left.

“What the fuck did I do to make her fucking hate me!”

Jared can be a lot to handle and know it bothers him when someone doesn’t respond well to his hyper personality, unlike me, Mr. Keep Your Damn Distance.

“I don’t know man, you’ve seen the shit she gives me,” Jared snorted, “like you don’t deserve it. Y/N’s friendly with everyone else..even puts up with Misha!” Jared fake pouts, “I overheard her and Alex planning some Christmas-themed bar hop next break.” 

I gave him a look and Jared bust out laughing then became somber, “wonder what happened with her family to feel like your not welcome. Fuck, don’t know if I could handle not being part of mine,” he remarked heading out and his words got me thinking too. 

Y/N is not the most open person, like me in that aspect, but thinking back, she deflects on a lot on personal stuff and got the idea of who might know something and plan on covertly visiting them in a couple of weeks.

December 3

San Francisco, CA 

Hyatt Regency SFO (Airport) Hotel

11:30 AM

Jared and I exited the stage and caught sight of JDM conversing with Y/N, laughing at some anecdote she’s saying before he’s called to the stage. 

Passing by, Jeff places a hand on my shoulder, halting me, and leans in muttering, “doesn’t she remind you of Jared when we first started?” 

He’s wearing his pay attention to what I’m not saying son, squeezing once joined Sam Smith onstage. 

“Hey,” Y/N tapping her wrist and cocking her head towards the prep room for me to hurry up and I follow and start appraising her with my director's eye. 

She’s fairly tall, but that’s not unusual for women nowadays, bland as hell hair color and could stand some different make-up, always wearing this unflattering lip rouge. Her wardrobe has some improvements but still, wonder if she’d let me take her shopping sometime. 

Hmm, it’s entirely possible this look is so she’ll be taken seriously still being.. Fuck, I don’t even know how old she! 

Her dark eyes start doing a weird, squinty blink, “your eyes bothering you?”

“Huh? Oh, guess it’s the A/C.” 

“I have some drops in my bag you can use.” 

“Thanks but I need the one for lens,” she abruptly stopped and did that downturn with her mouth.

“There’s a bottle in the front pocket,” pretending I didn’t hear that last bit, “help yourself,” and stroll out now knowing those glasses are fake.

~You~

December 18th

“What’d I do?” 

I turned to see Alex mirroring my shocked expression after Jensen snaps, no, fucking blew his fucking lid storming outta the makeup trailer. 

“I..I‘ve,” I stumbled over what to say because I’m not sure if he is aware of what happened four years ago. “It wasn't about you. Umm, I’m gonna head out and deal with the boss man.” 

Alex looked contrite, “okay, ahh..could you tell him I wanna apologize.”

“You don’t need to, been around long enough to know he’ll come to you hat in hand. So, I’ll see you tomorrow night at the pub crawl.”

~~~

I quietly shut the trailer door and sit next to Jensen finally get to see the photo I was told he always carries.

It’s a candid taken by his dad of Danneel, his mom, and him just before they’d had put JJ to bed that night four years ago unaware it’d be the last time.

He hastily tucks it away and on impulse I reach for the hand resting on his jean-clad thigh and tangled our fingers together when his chartreuse eyes cut to me, narrowing.

I learned when he does that, it’s not for people to drop whatever he’s not liking, it’s Jensen’s about to fucking go off for real.

“I went to LA,” I quickly dropped my gaze, “I’m taking you home and we’re gonna have a long conversation. Do you understand me, young lady?”

“Yes sir.”

I’m totally screwed.

~Jensen~

I shut her apartment door and immediately issue orders, “you’re gonna wash all that shit off and you’d better not come out till you’re squeaky clean, do you understand me?” 

Y/N’s eyes got big bit on her bottom lip and felt that sensation roll through me, “yes sir,” she whispered, “umm, it’s gonna take me a bit, make yourself at home. I don’t have much in the fridge but there’s a bottle in the cabinet over it,” and disappears through the bath door.

While she’s preoccupied I took the opportunity and have look around.

She lives in a very small furnished studio and don’t see one personal item sitting out, only a few Christmas cards on the dinette do something I’d normally never, ever do, and start going through drawers starting with the under bed storage found confirmation of what I’d observed and suspected about certain proclivities of hers.

Back to the kitchen I found the decent label bourbon grab it and pour two glasses then kick back on the sectionals chaise-end flipped through the channels finding an NFL game.

~~~

“What’s the score?”

“13 to..” my mouth dropped.

“I know,” downing the second glass of bourbon the alcohol roughed her voice, “I’m Jared minus the chest hair.”

I sat there amazed how the similarities outweighed their differences; minus the contouring makeup the shape of her face was Jared, even that tipped nose with random freckles instead of moles but her jawline was femininely softened and framed by much longer, cinnamony-chestnut hair.

Without the colored-contacts and hideous glasses I can see her fox-tilted eyes also have a unique color patterns. 

“I can’t wrap my head around this contrast,” waving my hand over her visage, “you lied, deceive us all..for what, shits and giggles?”

“This isn’t something I just started doing, I’ve been disguising this,” pointing to her face, “for years.”

“Why?”

“You gonna rat me out?”

“Don’t dodge my question.”

“This was Chad’s idea..”

“What the hell possessed you to listen to Murray? Know what, scratch that, start at the beginning.”

“David Copperfield beginning?”

“Don’t be a smartass.”

“You said it depends how nice the ass is and you could bounce a nickel off mine.”

“Now is not the time for levity.”

“If you're worried about Jared’s reaction, don’t. The only thing my famous brothers gonna care about is how fast you can ship me the fuck outta here!” The vitriol in her voice shocked me, only once I’ve heard her like this was when I was three sheets to the wind and acting like a bastard.

“I’m trying to wrap my head around the comments you’ve said versus what I know. The Padalecki's are one of the closest families I’ve ever met and I can’t conceive how it’s even possible for them to have hidden you all these years.”

“It started when Jared signed on with his management agency, some nonsense about our age gap and public opinion.” 

I remember opinions were more conservative back when we first started in the industry and public opinion is everything.

“How much of an age gap are we talking here?”

“Fourteen, you do the math.” 

“Holy fucking shit! You're only twenty-one?!”

“Twenty-two, my birthdays was on Halloween. Look, I’ll make you a deal, let me stay on til the thirty-first so I can get a leg up finding another position and..”

“And?”

“You apologize to Alex before he apologizes to you, he doesn’t know about JJ and this time of year.”

“Fuck, you and Jared are alike in more ways than one,” I refilled the glasses, “I’ll make you a counter-deal. You know I’m spending part of Christmas break with my parents,” she nodded, “pretend to be my girlfriend and..”

“What the hell? What makes you think I’d ever agree to that?”

“We’d be doing each other a favor, you’ll keep them off my back and I won’t say anything. We know enough about each other to get away with and you’ve proved to be one helluva actor, can improvise on the spot and I..”

“Just can’t bear to let the best assistant you’ve ever had go?” 

“If you’re wanna stick around, we’ll discuss a mutually beneficial off-the-clock relationship.”

“Why is my spidey sense tingling?”

“Maybe because I found some interesting items under that bed,” holding up one said items smirk, “wouldn't have taken you for a little.”

Y/N smirked back, “wouldn’t have taken you for a daddy.”

“You’ve been very, very naughty,” I unbuckled my belt and slipped it through the loops, “so daddy needs to reminded you what happens to bad girls.” 

SPN TAGS: @donnaintx @lyarr24 @flamencodiva @b3autyfuldisast3rr @lassie-bird @nancymcl @spnbaby-67 @leigh70

Sam/Jared: @idreamofplaid

Dean/Jensen: @thoughts-and-funnies @stoneyggirl2 @akshi8278 @beabutterfly987 @smoothdogsgirl @siospins2