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chiriwritesstuff · 4 months

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The Girl in IT - 3. Vroom Vroom

A Boss! Joel Miller x IT Specialist F! Reader AU

The LIST │ Series Masterlist

Chapter Rating: E (18+, MDNI)

Chapter Preview: "I want that Model X. Blacked out. The one that drives itself." He nods approvingly, not bothering to conceal his satisfaction. "Done. Anything else?" You can't help but scoff at the audacity. "Just like that?" "Just like that." "Come on, Joel. You don't just surprise employees with new cars out of the blue." "Well, lucky for you, you're not just any employee."

Chapter Warnings & Tags: No outbreak AU, Boss x Employee Relationship, Sugar Daddy Lite, Daddy Kink, Smut, SO MUCH SMUT, Age Gap, Praise kink, Overstimulation, Squirting, Older Man/Younger woman, So much dirty talk, DD/lg (kinda? they're both into it), Vaginal Fingering, Exhibitionism, No PIV (yet), Virgin Reader

Word Count: 6K

A/N & Chapter Notes: Two birthdays, ten years apart.

This is filthy, and I have no regrets.

Hope you enjoy!

Ten Years Earlier.

Joel lingers outside your house, the lively sounds of your 26th birthday party spilling into the night air through open windows. He adjusts the collar of his chambray button-down, opting for a change from his usual flannel attire. With his hair slicked back and facial hair neatly trimmed, he sighs, contemplating the small bouquet of sunflowers he acquired from a nearby florist.

His mind goes to the conversation he had with the florist earlier.

"Sunflowers? That's an interesting choice." The florist smiles, gently taking the flowers from his hand. "Did you need this wrapped? Maybe a bit of ribbon?"

Joel nods. "Please. It's for—"

The florist glances at him, a twinkle in her eyes as she observes his nervous demeanor. "Did you know that the sunflower symbolizes adoration? It's the perfect flower to give to someone you're interested in."

"Oh, it's nothing like that, It's for a... a friend. It's her birthday today."

The florist gives Joel a wry look. "If she's just a friend, might I suggest daisies? Surely they would be more appropriate and cheaper—"

Joel shakes his head. "The sunflowers," he motions to her hand. "Please."

He smiles at the memory, looking at the bouquet once more, knowing he made the right choice.

He spots you through the window, the vibrant yellow of your sundress gracefully accentuating your curves, creating an ethereal silhouette that seems to glow, like a beacon of light calling out to him. His breath catches in his throat as he watches you. A genuine laugh escapes you, a sound that always catches him off guard, echoing through the air with a light that he finds irresistible.

"Joel," your father approaches, his expression clearly showing his displeasure. "What are you doing here?"

"Hello Sir, Well, I'm here for a birthday party, and-" he lifts the invitation, "I believe I was invited."

"I can see that, but the question is why. Surely, a man of your age at a party filled with twenty-year-olds? Doesn't that seem... odd to you?"

"It's only odd if you make it odd, I reckon."

"Can I ask you a serious question? What are your intentions with my daughter?"

"Well, I would like to wish her a Happy Birthday, maybe eat a little cake-"

"... and how old are you, Joel? aren't you a bit bothered by the fact that your daughter is older than mine?"

"... well, she's not, sir." Joel smiles, "She's older than Sarah."

Unamused, your father continues. "I'm going to level with you. I'm not about to let my daughter be swept away by some middle-aged man barely scraping by." He shoots Joel a stern look, shaking his head in disapproval. "My daughter deserves the world, and quite frankly, I won't have her settle for someone beneath her. Not for some small-time contractor."

"Sir, that's not my intention at all. Sugar invited me, and-"

He shakes his head in disgust. "I think you should go, Joel. Take your flowers and go. You're lucky I let you still have this job."

Joel nods in defeat, his gaze lingering on you through the window. He takes a final appreciative look at you, radiant in your yellow dress, and offers a warm smile. Turning towards your father, he speaks with sincerity, "I apologize for any disturbance, sir." Joel strides purposefully towards his truck, adding, "Please convey my regrets to your wife."

Present day.

Joel: Hey Sugar, did you head out to the office yet? Sugar: Hi Mr. Miller, Good Morning! No, I haven't. Still getting ready. Should be heading out in 15. Did you need something? Did you get locked out of the company portal again? I told you that we change passwords every six months, I wrote it on a sticky note for you like you asked! Joel: No, Sugar, I haven't. It concerns me how little faith you have in me. I am not that hopeless! For your information, I am not in the office yet. Sugar: Oh? So it wasn't you and Ellie trying to figure out how you managed to print the printer manual ten times over last week? Joel: I'm sure that was Tommy, but it's ok, I forgive you. Anyway, does this mean you're still at home? Sugar: Sure, Joel. Ellie would say otherwise. Yes?? Joel: ??? Not sure if you're at home? Sugar: No. Yes. I'm at home. Joel: Good. I'm outside.

"Joel," you say, locking your front door, looking surprised. "What are you doing here?"

"I'm kidnapping you for the day," Joel announces from his truck. "Thought I'd give you a ride to work." He winks as he exits out of the cab, wearing a chambray shirt and jeans instead of his usual work-issued flannel. It's a nice change, being that you didn't think the man owned anything other than flannels. "Come on, I've got coffee and donuts."

You give him a wry smile. "What if I'm not a coffee person?"

Joel presents a coffee to-go cup, a tea bag tag hanging out. "Lucky for you, I've got your favorite green tea."

"Smooth move, Miller," you grin, approaching him and planting a kiss on his cheek. "Very smooth."

"What can I say? I have excellent attention to detail, especially when it comes to you."

"Just not with computers, right?"

"Alright, alright, none of your teasing this morning, why don't you hop in," Joel grins, holding the passenger door open for you. You slide into the truck, still puzzled by his unexpected visit.

As he drives away, the scenery doesn't match the route to the office. You raise an eyebrow, looking at Joel with a playful smirk. "This doesn't look like the way to work. Where are we going?"

"Well, if I told you, then it would ruin the surprise, now would it?"

You snort. "What's happening today that's so important it warrants a surprise?"

Joel glances at you, a wide smile on his face. "A little birdy told me that it's someone's birthday today."

"Yeah and? It doesn't mean that we blow work off, I actually have a scheduled meeting with Tess today-"

"Fuck Tess."

You frown. "Joel, be serious."

"I am serious. I handled Tess. She's fine, don't you worry your pretty little head off, she's ok with pushing back to tomorrow."

You look at him warily, sighing. "I got a bad feeling about this."

Joel reaches over and kisses your forehead. "Don't frown, baby. None of that nonsense is allowed when we're together, okay? Just let me do something nice for you on your birthday. Nothing too crazy, promise."

"Why do I have the feeling that you don't mean that?"

Joel drives into the mall's parking lot, heading towards Neiman Marcus, driving into the nearest parking stall to its entrance.

He cuts the ignition to the truck. "OK, I don't promise. I intend on dragging you into the store whether you like it or not, sliding my shiny Amex to the first salesperson I see, and spoiling the absolute shit outta you. Do you have a problem with that, baby?"

"What if I allow you to spoil me from the comfort of the clearance rack?"

"Sorry to break it to you, baby, but this Amex won't work on anything discounted. Do you know what it means to have a black one of these?"

"That you have a big cock and an even bigger ego?"

"Funny. What it really means is that I can walk into one of them Tesla dealerships and buy you a Model X before you can ask me if I'm being serious." He takes your hand in his. "Because I am. Serious, that is."

You scoff, sinking further into your seat. "You're not going to buy me a Tesla."

He laughs. "Maybe, maybe not. I do know you need a new car, and I know one thing for sure—" He gives you a wry smile as he lifts your chin to face him. "There's no way in hell I'm going to let you drive that damn death trap anymore, Sugar."

"Hey! I'll have you know, I've had that death trap since college, it's the first thing I bought without my father's money!" you huff, "Now that I'm not in the ninth layer of Hell at Best Buy anymore, I can finally afford to buy myself a car. You know, something sensible, like a Kia."

"A Kia? Baby... only more reason for me to buy you a new car. Tell me, if you could have any car, money, and cost be dammed, what would it be? Sky's the limit."

"Seriously?"

He leans in, eyes challenging. "Try me."

"I want that Model X. Blacked out. The one that drives itself."

He nods approvingly, not bothering to conceal his satisfaction. "Done. Anything else?"

You can't help but scoff at the audacity. "Just like that?"

"Just like that."

"Come on, Joel. You don't just surprise employees with new cars out of the blue."

"Well, lucky for you, you're not just any employee."

A smile tugs at your lips, appreciating the unexpected attention. "Really?" you playfully inquire. "So, I'm more than just a random employee, huh?"

Joel gently caresses your chin, offering a small, satisfied smirk.

"No, Sugar, you're not just some random employee," he declares, pressing a chaste kiss on your lips. "You're everything."

"You don't mean that—" you stutter, "Joel, what's going on? Why are you doing this? I'm not someone to be bought or bribed like I'm some sugar baby. I liked you back then, before all of this—"

"When I had nothing? When my company was still in the red, when your father's job was the only one turning a profit," he peers down at you. "What if I told you that I wouldn't be in this position if it weren't for you? If your father didn't talk some sense into me all those years ago, I wouldn't have worked my ass off to get where I am now."

Your eyes narrow. "What are you talking about?"

Joel lets out a heavy sigh, his gaze intense. "Your father made it clear back then that I wasn't good enough for you. He didn't think I was the right fit for you. He did me a favor if I think about it now. It was your father's skepticism that fueled my determination to prove him wrong, to build something from the ground up."

Your mind races, trying to grasp the weight of his revelation. "But why keep it a secret? Why now? You didn't give me any signs that you were interested in me, I even invited you to my birthday party, which you didn't even bother showing up to!"

Joel winces. "Yeah, about that-"

Your face softens. "Wait, Joel, the sunflowers?"

"Your father made sure to point out the inappropriateness of a middle-aged man attending a party full of co-eds. Thinking about it, it wouldn't have been a good look, especially since I couldn't take my eyes off of you, wearing that yellow dress… I was enchanted by you, baby girl."

You blush, smacking his shoulder. "Oh, that dress was horrendous. My mom made me wear it!"

"Well, remind me to thank your mom for giving me the mental image I've had of you all these years."

"You know, that explains why the sunflowers were in the trash can, I thought it was so odd! They were beautiful, by the way. I snuck them out and kept them in my room, you know." You shake your head. "I can't believe my dad would do something like this. I hate that I stuck around for so long. I wish I knew, Joel. Back then. You were the only person I looked forward to coming that night, and when you didn't, I thought-"

"Well, I was there, baby."

"… but you didn't stay! How was I supposed to know?!"

He runs a hand through his hair, clearly frustrated. "I didn't want you to feel like you were settling or that my feelings were tied to any of this. I needed to prove myself first. I didn't want you to think I was using you or that I wasn't good enough for you."

A mix of emotions swirls within you—surprise, confusion, and a hint of realization. "Joel, I had no idea. But why go to such lengths now? Buying me a car, showering me with gifts?"

He looks into your eyes, his expression sincere. "Because, despite everything, my feelings for you have always been genuine. I wanted you to see that I can give you the life you deserve and that I've overcome the doubts from back then. I had nothing to give to you back then, hell, I was being eaten alive by debt, I couldn't put Sarah through college - she worked her ass off trying to get as many scholarships as she could on her own. I wasn't in a position to make you mine, not yet."

"Joel," you say, taking his face in your hands, a sad smile on your face. "Do you think I care about all of this? I would have been with you then, all you had to do was ask."

"Well, I'm asking you now. Will you let me make up for missing your birthday all those years ago up to you?"

You give him a small smile. "Okay."

Joel breathes a sigh of relief. "Okay. Now, get out of the truck and into the store. That's an order."

You share a playful eye roll before complying, opening the truck door, and stepping into the crisp air outside. The familiar chime of the entrance doors signals your arrival at Neiman Marcus.

Joel walks beside you, his arm casually draped around your shoulders as you both make your way into the store. The ambiance of luxury surrounds you, and the scent of high-end perfumes lingers in the air. You can't help but marvel at the elegant displays showcasing the latest in fashion and accessories, the air smelling distinctively expensive and high class, something you would never associate yourself with.

"So, what's the plan?" you ask, hesitation evident in your voice.

Joel grins, steering you towards the women's clothing section. "I'm looking for just the right-" he stops midsentence, his eyes locking onto the stylishly dressed woman lying in wait for her next victim.

"Lenore!" he shouts, "Just the person I was hoping to find."

"Mr. Miller! What a delightful surprise," the saleswoman exclaims, her face lighting up. "What brings you here? how are your girls?"

"They're doing fine, thank you for asking."

"... and who is this pretty baby peeking out from behind you?" she asks, casting a warm smile your way. You instinctively recoil at the unexpected attention, a familiar sensation from the years spent trailing your mother at Neiman’s, deliberately making yourself inconspicuous to deter any unwanted conversations. It felt safer that way, you reflect, offering Lenore a slight smile. "There's our lovely girl. No need to hide behind this old dog; you're far more interesting to look at than he is!"

"Lenore, allow me to introduce you to someone very special—this is Sugar," Joel says with a proud smile, gesturing towards you.

"Sugar, what a sweet name! Pleasure to meet you," Lenore responds, extending a hand in a friendly gesture.

The tension from earlier begins to dissipate as you shake Lenore's hand and manage a genuine smile. "Nice to meet you too, Lenore."

"Sugar, why don't you take a look at the clothes over there and let me talk business with Lenore for a second?" You raise your eyebrows in suspicion, "Maybe you'll see something you like?"

Joel, his eyes gleaming with excitement, leans in and whispers, "Lenore, today is no ordinary day. It's Sugar's birthday, and I'm in the mood to make it special for her. We're going to be spending an obscene amount of money today, so I hope you're ready. You got your work cut out for you, I promise you that."

"Nothing can be as worse than the time I tried to convince Ellie to wear a gown for the prom last year," she winces, "Sorry about that again, Mr. Miller." She slides up beside Joel, flashing him a knowing smirk. "How obscene are we talking?"

Joel hands over his sleek black Amex, and Lenore's eyes widen in surprise. "Obscene. Don't let her talk you out of something because of the price, hell, rip off the damn tags if you have to." He steals a quick glance back at you, a vision standing amongst the designer goods, a subtle smile on his face. He glances at Lenore once more. "Do we have an understanding?"

The saleswoman nods her head frantically, pocketing the Amex in her pocket, the weight of it making an indentation through her blazer. "Understood, Mr. Miller. I'll fetch you a coffee and set up a seat for you in her dressing room. Is there anything else?

Joel nods. "Yeah. Do your worst, Lenore."

Lenore gives Joel one last look as she heads towards you, not hiding the fact that you look like a deer caught in the headlights. She places a hand on the small of your back. "Come along dear, we're on a mission." She gives you a conspiratorial smile. "You're in desperate need of Celine."

Lenore scrutinizes you for a moment, gently lifting your arms to assess your form. "I take it you're a size 10?"

Surprised, you ask, "How did you know?"

"Honey, I've been here for the last twenty years. Not only can I tell your dress and bra size, but I've also mastered the subtle art of reading people." She confidently places her hands on your hips, nodding to herself. "People are not as secretive as they think. I can dissect their entire life story the moment they walk in the door."

Curious, you inquire, "Oh? And what conclusion did you make about me?"

Lenore begins rifling through the racks, selecting a few monochromatic pieces. "Well, you seem to go through life trying to hide yourself."

"Is it that obvious?" you ask with a hint of self-awareness.

Lenore continues her assessment, her experienced eyes scanning the clothing options she's pulled out. "You go through life trying to hide yourself," she repeats, her tone thoughtful. "But, sweetheart, hiding doesn't mean you're weak or scared. It means you've faced challenges, learned to protect yourself."

She steps back, considering you with a knowing gaze. "We all wear different masks, dear. It's just a matter of finding the one that feels right for the occasion. Now, tell me, what's the story behind the layers you've wrapped yourself in?"

"Well..." you bite your lip thoughtfully, "Today is my 36th birthday. My mom, she had me when she was 26. By the time she was my age, she had her whole life figured out - the husband, the kid, the house. I remember thinking how much I wanted that for myself, how I thought my life would go... and now, at 36," you pause, sighing, "I don't have any of that. I'm not married, I don't have any kids, and I rent an absurdly overpriced shoebox that I share with my cat," you softly chuckle to yourself.

"It's not like I haven't tried to put myself out there. I have—met a few people, went on a couple of dates, which—I felt like wasn't terrible, you know?" You admire a sheath dress on the rack, adding it to the growing pile of pieces Lenore has accumulated. "...but it was always just a first date, and then rejection, maybe if they were kind, but most of the time I never hear from them again. After a while, after I hit 30, I just... stopped. I stopped trying to put myself out there. It's exhausting, and I can't keep wondering what makes me so undesirable."

"Sometimes... Sometimes I feel like I'm defective, too broken for anyone, not good enough to have the kind of life I want."

"Sweetheart, life rarely follows the script we write for it. Comparing your journey to your mother's or anyone else's is like comparing apples to oranges. Each story is unique, and yours is still unfolding," she reassures you.

She continues sorting through the clothes, selecting pieces that seem to resonate with your style. "Now, about those layers you wear," she begins, her focus returning to the task at hand. "Perhaps it's time to shed the expectations and judgments, not just from others but also from yourself. These layers, they're not defects; they're experiences that have shaped you."

Lenore hands you a beautifully tailored blazer and nods approvingly. "Try this on. Let's see how it feels."

As you slip into the blazer, Lenore continues, "You deserve a life that brings you joy, and that starts with accepting yourself. When you embrace who you are, others will too. It's not about being 'good enough'; it's about being authentically you."

Lenore, her hands expertly moving through the racks, pauses for a moment, her gaze thoughtful. "And what about Mr. Miller?" she asks with a knowing smile. "There's a story there too, isn't it?"

You glance at her, surprised by her perceptiveness. "Joel? Well, we've known each other for ten years, but we've only worked together for six months. There's nothing more to it than that."

Lenore raises an eyebrow. "Sweetheart, I've been around enough to recognize when there's something more. The way he looks at you, the way he cares—it goes beyond the confines of a professional relationship."

You hesitate, unsure of how to respond. Lenore gently continues, "I've seen people in love, and I've seen people trying to hide it. Joel's got a soft spot for you, dear. It's written all over him."

"Is it? because with my track record, all it feels like is me waiting for the other shoe to drop. I like him... I've liked him", you correct yourself, "...for a very long time. I tried to put myself out there to him back then, only for him to reject me. What makes me different now? What didn't I have then?"

Lenore listens attentively, her gaze filled with compassion. "Sweetheart, people change, circumstances change. What may not have worked before doesn't define your worth or potential now. Maybe back then, Joel wasn't ready or didn't see what was right in front of him. It doesn't mean you lacked anything—it just wasn't the right time."

She pauses, choosing her words carefully. "Love can be messy, complicated, and unpredictable. But if you feel something for Joel, and there's a chance he feels the same now, it's worth exploring. Give yourself permission to embrace the present without being burdened by the past." She gives you one last smile, her tiny frame effortlessly handling the mountain of clothes with an ease that comes with her years of experience. "Come on, we can't leave Mr. Miller waiting. He's already waiting for you in your dressing room."

Joel is already seated in the room one would call a dressing room, a vast space encapsulated by mirrors. Lenore places the clothes on the rack, giving the two of you one last-knowing nod as she makes her way to the door. "I'll give you guys some privacy," she winks, her hands on the doorknob. "You just holler if you need anything, okay?" You smile meekly at her as Joel nods. "Thank you, Lenore."

"Well', you breathe, making your way to the center of the room, taking it all in. "This is... something."

"It is, right? Perfect amount of mirrors to admire your form."

"It's just... a lot, Joel. I'm not used to seeing myself like this."

"Like what, baby?" He asks, making his way over to you as you fiddle nervously in place. Tenderly, he envelops you in his arms, hands brushing away stray strands of hair behind your ears. "Turn around and face the mirror," he softly directs, gently guiding you by the hips. You find yourself in front of the mirror, Joel standing behind you, his eyes locking with yours as his hands trace down your silhouette, fingers deftly navigating the buttons of your blouse.

"Let me paint a picture for you," Joel whispers in your ear, his eyes locked with yours through the mirror as he delicately starts to unbutton. "I see someone who drives me fucking crazy." Pausing at the last button, he eases your top from the waistband of your skirt, peeling the fabric from your skin to unveil the modest cotton bralette you chose for the day. "Beautiful," he breathes, slipping your top from your shoulders. A shiver runs through you as his hands graze your skin, leaving a trail of goosebumps in their wake.

"You think you can hide yourself behind all of these clothes but I see you, Sugar. I've seen what's inside, and I would like to get to know that girl that's begging to come out of that shell of yours." His fingers linger on the elastic at your waist, his eyes silently asking for consent. You nod, taking a deep breath as he slowly slides your skirt down your hips, leaving you standing against him in just your underthings, your body suddenly on fire as he continues to hold you against him. You swear you can feel the hardness of his desire from behind as he continues to caress you, his eyes never leaving yours. "Will you show me?"

His fingers find the skin of your torso, and you shudder and gasp at how it suddenly ignites you, the fire you kept dormant for so long suddenly ablaze from his ministrations, leaving you breathless. He places wet open-mouthed kisses along the length of your neck, his eyes never leaving yours as his fingers start to travel down to your waist.

The corner of his mouth creeps slowly upwards. "Are you going to let me show you just how much I fucking adore you?"

You swallow thickly, nodding absentmindedly as you find yourself caught in his web, exactly where he wants you. "Yes", you whisper, "Please, Joel."

"Do you know how long I've waited for you?" he whispers, his fingertips grazing the outline of your panties, inching lower and lower, the sensation driving you mad with want. You instinctively rub your thighs together, your body craving more friction than what's currently being provided. Joel tsks at the gesture, shaking his head at you through the mirror. "You keep these legs spread for me, baby." His fingers wander upwards, hooking onto the elastic of your underwear, as he watches you closely, a question written across his face. He quirks his eyebrow at you curiously.

It was all you needed to know just exactly what he was asking.

You give him a tiny nod.

"Use your words, baby girl. I need to know for sure that this is what you want. I need you to be specific," he commands, his fingers twitching against your skin.

"Please Joel," you whisper, the entirety of your body trembling against his, "Please undress me."

He grins wickedly as he complies, the fabric slipping slowly down your hips, peeling gently down your legs. "I remember the day we first met at your house, how shy and skittish you were. I remember what you wore, even then," he says, taking his time, your panties caught on the ankle of your foot. He tugs them free, his eyes darkening as he realizes that they are soaked through with your slick, glistening under the lowlight of the dressing room.

You swear you hear his breath quickening as he holds them high against the light in reverence, tucking the scrap piece of fabric into his back pocket.

"Did you know that you were going to see me that day?" he asks, turning his attention back to you. "Is that why you didn't bother to wear a bra under that shirt of yours?" He shakes his head slowly as he places his hands on your hips once more, his fingers slowly making their way down to your inner thighs. "It was downright indecent, the fabric was so thin I could practically see your tits," his voice sounds more considerably wrecked as he slides his fingers upwards until they hit your slit, a calloused finger expertly parting your lips until they reach the button of your clit.

He stops. "Have you ever let anyone touch you like this before?"

You shake your head in response, your body arching against his as you desperately seek his touch. "I came close once, back in college, but I-" your voice gets caught in your throat as Joel eases his finger through your lips once more, his fingertips at the precipice of your entrance. You can't help the moan that escapes your lips. He pulls his fingers away from your heat as he reaches into his back pocket, reaching for your panties as he holds the wad of fabric against your mouth. "Open," he commands, stuffing your mouth with the fabric, the tang of your slick so sharp it makes your mouth water even more. "This is a public place, baby, I can't risk us getting kicked out because you can't control yourself, you hear? Nod if you understand me."

You nod.

"Good." He bends forwards slightly, his fingers parting your slit once more, your pussy lips quivering as he gathers your slick, his fingertips breaching your entrance once more. "I know you're still a virgin, Sugar", he breathes as he kisses your neck once more, his eyes locking onto yours. "I'm not going to fuck you with my cock in a dressing room, but I am going to show you just how you make me feel. Is that okay?"

You nod once more, your voice muffled through the fabric of your panties. He breaches your entrance slowly, the thickness of his finger filling you as your body jolts from the intrusion, your eyes closing in pleasure.

"Look at me, Sugar. Look at what I'm doing to you."

Your eyes shoot open as you see Joel adding another finger into you, the squelch of your wetness against his fingers echoing loudly throughout the room as they slowly pump in and out of your pussy, his fingers crooking inside you slightly as your hips shift against his erection. Joel groans at that, shifting his thigh between your legs. "Lean against me, baby. Watch as I fuck you with my fingers."

You look at yourself in the mirror, the straps of your bralette sliding down your shoulders as Joel fingers you in earnest, tears forming at the corners of your eyes as you wither and tremble against his thigh. Joel pulls the chair he was sitting on earlier towards the both of you, pulling his fingers out of you once more as he plops onto the seat, spreading his legs. He beckons his fingers coated in your slick at you. "Come sit on Daddy's lap like a good little girl."

You stumble inelegantly onto his lap, his hands spreading your legs to rest on his, spreading you out entirely as he gazes at your pussy in the mirror, your ass situated on his jean-covered cock as he starts to grind against you. He pulls your breasts out from the confines of your bralette, the slick of your pussy leaving a trail against your skin as he cups your tits, pinching your nipples as he groans into your neck. "Look at you," he praises, slipping his fingers into your pussy as he begins to finger fuck you into oblivion. You look completely debauched as he thoroughly fucks you, his groans growing louder as he continues to grind his cock against the swell of your ass.

"Sweet innocent little Sugar, playing hooky and getting wrecked by her boss in public", he spits, his fingers increasing in speed as you mewl against the fabric in your mouth. "What would everyone say, huh? Pulling into the parking lot with your brand new Tesla, walking into the office tomorrow morning in your brand new clothes Daddy bought you?" He rubs his thumb against your clit, your body arching back as you cry from overstimulation. "Are you going to take everything that I'm going to give you?" he pulls the fabric from your mouth, a line of saliva trailing it as you breathe harshly, desperately trying to even your breath. "I asked you a question, Sugar. Are you going to take everything I give you?" he rips his fingers out of your pussy as it clenches on nothing, whining from being so violently edged out. He slaps your pussy for good measure, and you swear you could come from the motion alone. "Answer me!" he growls in your ear.

"Yes!" you half-scream. "Joel, it's too much, I can't-"

"Yes, you can, baby. Fuck- keep grinding that ass on my cock, I'm so fucking close", he grips your hip harshly, his fingers digging into the meat of your skin you swear it'll leave a mark. "I can feel you quivering for me, baby, are you gonna come?" He's thrusting, thrusting so harshly against you it's almost to the point of pain, but you're so caught up chasing your release that the pain riles you up, you find yourself gyrating against his hardness as Joel nearly jumps out of his seat in response.

"Joel, what's happening? I feel so wet, you need to stop, I feel like I'm gonna-" You gasp, the pressure building within you so strongly it feels like you're going to implode. Your body moves in sync with his, the groans and shouts of pleasure building, the tears flowing freely down your cheeks. "It's too much, it's too-" You scream, a gush of wetness flooding out of you as Joel fingers you to completion, a look of shock on your face as he grips your hips and comes in his jeans.

"FUCK!" he groans as he shoots his load so violently you swear you can feel the ropes of cum through his jeans as he comes down from his high. You sob into his shoulder, his mouth desperately finding yours as he finally kisses you, his tongue running along the seam of your lips, begging for entrance as he grips the back of your head. You kiss him back in earnest, turning yourself around and straddling his thighs, your bare pussy raw against the fabric of his jeans. "Thank you," he mumbles against your lips, his hands cupping your cheeks, his thumbs wiping your tears away. "You did so good, baby, so fucking good, you came so hard for me you fucking squirted, FUCK! Such a perfect girl, my perfect girl-"

Your eyes widen in shock as you take in the scene before you, the wetness of your slick coating the surface of the dressing room. "Joel, I can't believe I-" You shift on his lap, panicking. "Fuck, Joel, what are we gonna do? I just came all over the dressing room, in Neiman Marcus for fucks sake-"

Joel chuckles softly, gently tucking your hair behind your ears. "Do you realize the power a black Amex wields? Silence. Lenore's commission today will be outrageous; a few stains here and there won't even register."

"But what if it ruined the merchandise? I haven't even tried anything on—"

"No need. Lenore's already taken care of it on the card. I trust her taste." He plants another tender kiss on your lips, retrieving a sleek silver card from his jeans pocket, the unmistakable Tesla logo gleaming.

He hands you the card with a smirk, and your eyes widen in astonishment as you delicately accept it.

"Happy Birthday, Baby."

The Updated List: (Line items 4, 15 & 16 completed this chapter_)

Taglist: @sarcasm-theotherwhitemeat, @gwendibleywrites, @joeldjarin, @brittmb115, @thewiigers,

@auteurdelabre, @quicax3, @casa-boiardi, @amyispxnk, @untamedheart81,

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chiriwritesstuff · 4 months

Text

The Girl in IT - 2. Off to the Races

A Boss! Joel Miller x IT Specialist F! Reader AU

Previous Chapter │ The LIST │ Series Masterlist

Chapter Rating: E (18+, MDNI)

Chapter Preview: You hesitantly reach for the massive bouquet, looking at the beautiful mix of colors in awe. "Joel," you breathe, "They're beautiful." "The woman at the shop said that certain flowers can have meaning. She asked me about you." He points to the flowers in your hand. "Lilies, well, they mean infatuation. Chrysanthemums, for excitement." He points to the pink rose. "For sweetness and admiration." "and the carnations?" "For fascination and enchantment." "Joel.. you don't mean that, do you?" He chuckles. "Oh, I absolutely do, Sugar. Those flowers are just my way of expressing what I already know."

Chapter Warnings and Tags: Joel Miller is hungry and wants to EAT, Smut, One massive Tess sized-cockblock, Boss x Employee relationship, Time Jumping to and fro, Joel Miller is a silly flirt, Joel jumps right in, Explicit language, Did I mention smut?, Soft boy Joel Miller

Word Count: 3.6K

A/N: You GUYS. YOU GUYS (!!!!!)

Thank you so much for all of the love for the first chapter of my silly little series with my even sillier Old Man Joel and his Sugar. I am absolutely flabbergasted by all of the likes, reblogs, and comments from all of you, it really means a lot to me! Thank you, from the bottom of my heart. You have no idea how much it means to me.

I have the first few chapters written and planned out, and I hope to post at least a new chapter once a week. I can't make any promises as I go back to work next week, but I will try. I apologize in advance if I skip a week, it is not my intention to let you guys down.

I hope you all enjoy!

Today.

[Hey Sugar, are you in your office right now?]

Yes, did you need something, Mr. Miller?

[Yes, actually, I do. I'll come to you, don't leave!]

A knock on the door startles you.

"Hey, Sugar?" Tommy Miller's voice rings out from the other side of the door. "Have you seen Joel? I know he said he had to ask you about something, but that was an hour ago-"

"Yeah?" you reply, almost in a whine, your head tipped back in pleasure as you try to muffle a scream. "Joel? No, haven't seen him around. No, not since this—"

There's a pause, and then Tommy's voice comes again, this time with a hint of amusement. "Still wrestling with his laptop, huh? The man can't even change his wallpaper without causing a crisis. I'll check his usual spots. If you see him, tell him Tess needs him in her office, pronto."

Just then, the muted sound of a cough under your desk catches your attention. You look down to find Joel, crouched beneath the desk with a sheepish grin on his face.

"Now, where were we?" he chuckles, his eyes meeting yours with a mischievous glint.

“Joel!” You smack him playfully as you roll your desk chair back. “Tess will have your head if you don’t show up soon!”

“But I’m starving, baby! Just let me have a little snack-“ he pulls your chair back to him as he situates himself under your desk, lifting your skirt as he smiles at the sight of your barely-there scrap of lace one would call underwear. “Shit baby, is this for me?” He lowers his head to your aching cunt, his arms wrapping around your thighs as he pulls you closer to his mouth. He rubs the tip of his nose along your slit, a satisfied smirk forming on his lips. He licks at your covered mound, the tip of his tongue adding just enough pressure for you to gasp out in pleasure. “I asked you a question, baby girl. Who did you wear these panties for?”

“You,” you say breathily, covering your mouth to muffle up your moans as he plants kisses along your thighs. “You, Mr. Miller. Only you.”

“Who owns this pretty pussy?”

"You do, Sir."

"Damn right, I do." Joel licks his lips as he pushes your panties aside, licking your clit. "Fuck, she's aching for me, isn't she?" He locks his eyes with yours, his mouth hovering over your pussy. "Can I?"

You nod, not trusting yourself to keep quiet.

Joel shakes his head, displeased with your answer. "No baby, use your words-" he growls, nipping at your thighs as you wince in pain.

"PLEASE Joel, keep going!" He smiles at your eagerness, licking and parting your folds with his tongue. He pins you against his face, tightening his hold on you as your body trembles.

"Fuck, you taste so fucking sweet-"

"JOEL!" Tess's voice reverberates through the hallway, the urgency evident in her heavy-footed approach, each step echoing past your office door. "Has anyone seen him?!"

Joel lets out an exasperated groan, his head dropping onto your lap as you suppress a giggle. "Duty calls, Mr. Miller. Can't keep your boss waiting, can you?"

"I am the boss, just so you're clear on that."

"Sure, Joel, keep telling yourself that."

Joel crawls out from under your desk with a grunt, stumbling onto the carpet with a thud. "I'm definitely too old for this shit," he mutters, trying to regain his footing.

"It's your list, Mr. Miller. You make the rules, I just help you execute it," you quip, smirking as you extend a hand to help him up.

He takes your hand, a mischievous glint in his eyes. He yanks you towards him, and you end up falling into his lap. "Right where I want you," he smirks, capturing your lips in a kiss.

You smile as he starts to kiss along your jaw. "You are insatiable."

"Only for you, Sugar."

"JOEL, FOR FUCKS SAKE!" Tess bellows from across the building.

"You better go before she breaks down all the doors," you wince as you give him a small frown. "Again."

Joel sighs, pressing one last kiss on your forehead. "Fine, but once I'm done with Ms. Pain in my ass-"

"You're going to go back to work like a good boy?" you reply sweetly, straightening out your skirt as Joel heads towards the door. He gives you one last glance as he turns the doorknob, a hungry look on his face.

"This isn't over, baby girl. When I come back, I expect to eat."

Ten years earlier.

"Joel! Tommy! Thank you so much for coming! Please, come in, come in!"

Joel straightens up and smooths out his flannel, nervously fiddling with his tool belt slung taut on his hips. He gives a curt nod to the client, turning to his side expecting to find Tommy next to him. His eyes narrow at the empty space. "Tommy, you fuck," he hissed under his breath at his brother, who was casually smoking a cigarette off to the side of the client's perfectly manicured lawn. "Put that out and stop fucking around, we're getting paid for this shit!"

Tommy takes a long drag, exhaling a long plume of smoke before flicking the cigarette onto the street. "This is small-time shit, Joel. We should be playing with the big dogs, not wasting our time doing residential work. How much was the bid?"

"20."

"Bullshit. This is no more than 5, and you know it. It's just a fucking scorched roof, and at only one side, it's not even a complete replacement."

Joel scoffs at his brother, his eyes narrowing in irritation. "Have you seen the size of this fucking house? We're in fucking Westlake Hills, for fucks sake. Think of the potential! Maybe we can convince them to replace the entire roof, replace their windows... fuck, I just want to make a good impression!"

"Oh, so is that why you're dressed like a fucking moron? Cowboy boots? Really? You're 46, not 26." he appraises him as he makes his way towards the front of the house. "Don't tuck in your shirt, man. I can see your fucking beer belly from here!" Tommy looks towards the front door, the client having already retreated into the home. He cocks his head and whispers to his older brother. "Is the wife hot? Shit. Maybe I should have run a comb through my hair-"

"They want this project done in a month."

Tommy whips his head towards Joel. "Are you fucking KIDDING ME? JOEL-"

"Boys!" The client's voice cuts through the building tension between the brothers, a sweet conspiratory smile on her face. "Are you coming?" She looks out into the distance beyond the brothers, a big smile blooming across her face. "Oh, Sugar! come and meet the boys who are fixing up the roof, you know, the side where your antenna thing exploded?" She beckons to the figure who was suddenly behind them, motioning her to join their conversation.

She's a sweet little thing, Joel muses, all nerves and jitters like a baby calf attempting to walk for the first time. So fucking cute, he thinks to himself. You were dressed for the brutality of the Austin summer, with barely there cut-off shorts and a tiny white baby tee, the sweat forming on your skin wetting the thin fabric, and if Joel looked hard enough, he swears he saw the outline of your nip-"

"Baby," the client rings out, forcing Joel to look away in embarrassment, a blush forming on his neck all the way up to his face. "You remember Joel Miller, the contractor we ran into in the mall?"

"Yeah. I remember. Hi, Mr. Miller."

You cringed as you approached, your head downcast as you awkwardly reached your overbearing mother. "Tommy, come and meet my daughter, we call her Sugar, because she's so sweet! She's back home from UT Dallas, she's working her way up to her master's in IT! We're all so proud of-"

"Mom," you whine, glaring at the ground as you shift around uncomfortably. "I don't think they care about what I'm doing at school."

"Don't be silly, Sugar," the mom chided with a dismissive wave. "These fine gentlemen surely appreciate a smart, capable woman, right, Joel? Tommy?"

Joel, momentarily caught off guard by the unexpected introduction, nodded with a friendly smile. "Absolutely, ma'am. Education is valuable, and we're glad to have such esteemed company. It's hard enough to go through earning your bachelor's, I'm sure it's hell trying to navigate trying to get your masters!" Joel clears his throat as he gives her a nervous smile. "You look great, by the way. You look well rested, I reckon this break is doing you some good."

Tommy, giving Joel an amused look, chimed in. "Smart is the new sexy, Sugar. Nothing to be shy about. I agree," Tommy winks at his brother as his smile widens at Joel's nervous shuffling. "Joel sure likes them smart and capable, alright."

You blushed, still uncomfortable with the attention. "Well, uh, nice to meet you, Tommy, and it's nice to see you again, Joel," You mumbled, avoiding eye contact.

"Pleasure to see you again too, Sugar," Joel replies.

Tommy chokes on nothing as he witnesses his brother taking the girl's hand in his, placing a soft kiss on it.

"Oh, brother of mine," he whispered to himself, shaking his head at seeing how smitten his brother was for you. "For fucks sake, what the hell am I going to do with you?"

Six Months and One Week ago.

"Sugar? Is that you?"

You turn towards the deep voice, smiling at the body that it's coming from. "Mr. Miller, it's nice to see you again. Thank you so much for this opportunity-"

"I heard from your mother that you got that Masters, I'm proud of you, girlie."

"Oh," you stammer, "It was nothing-"

"Don't do that," Joel says with a frown, shaking his head in disappointment.

"Do what?" you ask, matching his frown as he steps towards you. You can't help but gasp at his sudden boldness. You keep your hands glued to your sides, willing yourself to not reach out to his chest. You forgot just how much he affected you, even if it's been a decade since you've seen him last. He's older, sure, with strands of grey peppered throughout his curly hair... but he's different too, the remnants of his boyish charm morphing into something harder, more rugged, more broad. You tremble under his scrutiny. You force yourself to meet his heavy gaze. "Do what?" you repeat out louder, your voice getting caught in your throat as you push an errant strand of hair away from your face.

"You shouldn't downplay yourself like that. Earning something like your Master's is a big deal, don't sell yourself short like that, okay?"

You grant him a small smile. "Okay."

Joel, satisfied with your answer, nods. "Want to grab a cup of coffee with me?"

Six Months Ago.

"Are you sure she's good? Joel! Are you fucking listening?" Tess snaps, her fingers snapping for emphasis as Joel jolts in surprise. "It says here that she's been working at the Geek Squad for the last eight years; that's hardly enough experience to run an entire department—"

"She has her masters in Management Information Systems from UT Dallas, and the person who vouched for her-"

"Yeah, her mother? If she's as old as you, I highly doubt she can grasp what we need... what are we doing Joel? Are we just letting little old rich ladies headhunt for us now? I don't need no privileged priss in some ball gown running IT, we're a multi-million dollar company-"

"... who didn't even have a decent IT department in the first place, and now that Gloria is retiring, shit, Tess-" Joel runs his hands through his hair as he groans in frustration. "... she's better than everyone else we've interviewed, hell- at least we know that she's a lifer, being that she's worked for minimum wage at Best Buy for almost a decade! We have a chance to bring someone in to help out with the draftsmen, shit, she's even proficient in Revit! Tess, level with me: with her knowing that 3D modeling shit - we need her! More than she needs us!"

"So it's not that you want to fuck her, then?" Tess rolls her eyes as she throws your resume on his desk. "Yeah, Tommy mentioned your little high school crush on her, it's funny, you conveniently forgot to mention that-"

"Tess, don't."

"So if we decide to hire her, I won't catch you fucking her in your office? Her office? The conference room, the supply closet..." She glares at him, tipping her head back as she pinches the bridge of her nose in annoyance.

"For fucks sake Tess, are we hiring her or not?"

Tess rises from her seat, running her hands down her slacks to straighten them, and gives Joel one last glance. With a half-smile, she shakes her head as she heads toward the door. "I'll email her an offer. If she takes it, she takes it... But, I will be starting her off at our base pay."

Joel nods, suppressing the urge to beam as much as he'd like. "That's fine."

"Oh? And Joel?" She pivots back to Joel, hand on the doorknob. "I didn't hear a no. If I catch you guys in my office, I will fucking castrate you, you hear?"

Two weeks ago.

To: [email protected]

Fr: [email protected]

Subject: About that list...

11:30 am (30 min ago)

Sugar,

Thanks for saving my ass last night. The meeting with The H Hotel went off with a hitch and Tess was none the wiser for my little mishap... no harm, no foul, right? Right.

About earlier today, when you said "Let's do this", was that a "Yes, maybe?" or a "Yes, definitely?" because I would very much like to do this, with you, at your pace, of course. I don't want to pressure you or anything. I'm just fucking excited, you know? You have no idea how much I've wanted to talk to you back then... I let shit get into my head, you know? Fuck. I'm rambling.

Thank you for giving me a chance, Sugar. I promise I will do everything in my power to make it worth your while.

Joel

To: [email protected]

Fr: [email protected]

Subject: RE: About that list...

11:45 am (0 min ago)

Yes, definitely. Yes to all of it.

When do you want to start?

One week ago.

[Hey Sugar, are you busy?]

Not at the moment, I'm about to clock out for lunch, what's up? Did you click on a phishing link again?

[Sugar, have a little faith! Say, I'm about to head out to lunch too, meet me in the parking lot in 5?]

That's rather forward and presumptuous of you, Mr. Miller. What if I had already brought lunch from home? What if I was looking forward to eating my adult lunchable?

[What the hell is an adult lunchable? It sounds terrible! What if I take you to that little Sushi joint down the road? Would that be enough to convince you to come out with me? I'll let you snack on the lunchable on the way there.]

Hey! Don't knock my charcuterie! Also, Doesn't that "little sushi joint" have a two-month waiting list? It's impossible to get in! I thought that it was only open for dinner?

[Baby, don't you know that we built that restaurant? Masayoshi is a good friend of mine, and he owes me a favor. All it takes is one call, what do you say? Nothing's impossible for my Sugar.]

Nothing's impossible for my Sugar. Sugar. My Sugar. You read Joel's message over and over again, your stomach growling as you contemplate the current state of your life. If someone had told you six months ago that you would manage to not only crawl your way out of the depths of Geek Squad hell, snag a decent job, and catch the eye of your hot-as-fuck boss, you would have laughed in their face at how ridiculous that sounded. It is ridiculous - how one little mistake led to having everything you could have possibly wanted out of your minuscule life, hot man included. So what if you haven't had a serious relationship since college? It's not like you were with your ex long enough for you to go all the way, and even then, you weren't remotely even into him, he was too skinny and nerdy and didn't scream 'man' at all. His nervous laughter and awkward shaking did nothing for you. Joel, on the other hand- now that was a man. A man you wouldn't mind climbing like a tree, all thick and firm and sturdy...

[Sugar? You still there? Are we doing this or not?]

You snap out of your daydreaming, your decision already being made. Your hands shake as you type out your response, your fingers striking the keys with a finality that you never would have thought you would ever have the courage for. Well, you think to yourself as you press enter. Here goes nothing...

I'll be right there. See you soon.

[That's my good girl.]

"Hey, Sugar," Joel greeted with a playful grin from the driver's seat of his F-150, his arm casually resting on the open window. His eyes lingered on you as if savoring the moment. "Hop in, Masayoshi is heading over to the restaurant now."

You rolled your eyes with a teasing smirk as you approached the passenger side, clamoring into the cab with a bit of awkward grace. "Just like that? A single call to your chef friend, and he drops everything to cater to your every whim? Color me impressed, Mr. Miller."

Joel chuckled. "Well, what can I say? I am sort of a big deal." He reached for your hand across the center console, fingers intertwining, his thumb tracing soothing circles on your skin. "Is this okay, Sugar?" He lifted your hand to his lips, planting a gentle kiss. You couldn't help but smile, feeling a delightful flutter in your stomach. Turning your head away, you mumbled, "It's very okay, Mr. Miller."

"Now, what did I tell you?" Joel teased, a glint in his eyes. "It's Joel, none of this Mr. Miller nonsense. Save that for when we're crossing off items on my list, alright?"

You couldn't help but laugh nervously, a blush creeping up your cheeks as Joel's easy charm and forwardness caught you off guard. "You're going to be the death of me, Joel," you quipped, half-jokingly, half-serious, unsure how to navigate the sudden closeness. The air in the truck seemed to hum with a subtle tension, and you wondered if Joel could sense the rapid beating of your heart.

Joel's gaze held a playful sparkle, and he grinned. "Well, Sugar, I hope it's a good way to go." He revved the engine, and the truck rumbled to life as he pulled out onto the road.

"So, Sugar, tell me something interesting about yourself," his fingers tapping the steering wheel to an imaginary beat.

You chuckled, playing along. "Well, Joel, I like to teach myself new things, I have a British shorthair named Sir Bubbles, you know, because I was obsessed with Bridgerton, And, by the way, it's Mr. Miller only when executing things on your list, right?" you teased, recalling his earlier remark.

Joel shot you a sly grin. "Sharp memory, Sugar. You're catching on quickly."

As you neared the sushi restaurant, the conversation seamlessly transitioned to lighter topics. Joel shared stories about his work, and how it felt working with Tommy and Tess, and you found yourself drawn into his earnestness and honesty. The playful banter continued as Joel made his way towards the edge of town, your cheeks hurting from how easy it was to smile in his company.

Parking the truck, Joel turned to you with a playful glint in his eye. "Ready for some sushi and more of my irresistibly charming company, Sugar?"

You roll your eyes, feigning reluctance. "Oh, the charm? I don't know if I can handle it, Mr. Miller."

He grins, opening your door with a flourish. "Well, brace yourself, because it's coming."

As you step out, Joel pauses, reaching behind your seat. "Wait a sec," he says, unveiling what looks like the botanical equivalent of a small garden. "A little something to brighten up your day."

You raise an eyebrow. "Is this part of the list?"

Joel chuckles. "Maybe."

You hesitantly reach for the massive bouquet, looking at the beautiful mix of colors in awe. "Joel," you breathe, "They're beautiful."

"The woman at the shop said that certain flowers can have meaning. She asked me about you." He points to the flowers in your hand. "Lilies, well, they mean infatuation. Chrysanthemums, for excitement." He points to the pink rose. "For sweetness and admiration."

"and the carnations?"

"For fascination and enchantment."

"Joel.. you don't mean that, do you?"

He chuckles. "Oh, I absolutely do, Sugar. Those flowers are just my way of expressing what I already know."

You playfully roll your eyes, holding the bouquet to your chest. "You're quite the charmer, Mr. Miller."

"Only for you," he replies with a wink, taking your hand as you both head towards the sushi restaurant. "After you, baby girl."

After lunch, you and Joel emerge to find the heavens have opened up, rain pouring down in sheets. Joel stops you in your tracks, his eyes locking onto yours with a mixture of sincerity and mischief.

With a twinkle in his eye, he asks, "Mind if I tick off the first thing on my list?"

You smile, stepping closer to Joel as he tucks an arm around your waist, pulling you closer to him, the both of you soaked to the bone.

"Yes please, Mr. Miller."

Taglist: @sarcasm-theotherwhitemeat, @gwendibleywrites, @joeldjarin, @brittmb115, @thewiigers,

@auteurdelabre, @quicax3, @casa-boiardi, @amyispxnk, @untamedheart81,

@paleidiot, @bbiophiliaa (I apologize if I missed anyone, but if you are looking for any of my fic updates, please feel free to follow my updates blog @chiriwritesstuffnotifs!)

As always, dividers by @saradika-graphics

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