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jahayla-parker · 1 year

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Hey 💜💙 I was wondering if you could do a Tom Holland x reader fanfic with #19 from the kissing prompt list? The scenario can be that Tom and the reader are in a secret relationship because the reader is his personal assistant. Tom and reader have had sex before with other people in prior relationships but this will be their first time with each other so this will start with kissing and end with a good amount of smut if that makes sense at all lol

Getting Personal: Tom Holland x Reader Smut

Description: 13.5k wc smut where Tom falls for his personal assistant y/n and the heat between them is palpable but he struggles given their professional relationship.

Warnings: 18+ smut content, jealousy, p in v, unprotected sex, riding, mentions of orgasm, cum, masterbation, etc. teasing, and similar sexual content.

“So Tom here are the posters you need to sign for the fans” y/n says, setting the papers down on his desk as he looks up from his script.

As she pulls back, her hand brushes against his bare arm, sparks shooting through her as a result.

Tom seems to feel it as well as he tenses but smiles up at her as she stands behind him.

“Thank you y/n, do you mind grabbing me a new sharpie for them?” He asks kindly.

“Do I even want to know what you did with the last one?” She laughs, shaking her head as she walks to the door.

Tom secretly watches her hips as she walks away from him and mentally yells at himself for fantasizing about his personal assistant.

“Harry lost this one, I swear” Tom defended, making her laugh again before exiting the room.

“Girl” y/f/n gushes, coming up to her.

“Hmm?” Y/n asks already knowing where it was heading.

“You’ve gotta act on this. Look at the dumb grin on your face each time you leave his office” y/f/n smirks.

Y/n rolls her eyes, “there’s nothing to act on”.

“He can’t stop staring at you regardless of where we are, gives you secret smiles across the room, always checks to see your thoughts on projects you have no business giving input on, and you’re saying there’s nothing there?” Y/f/n groans, following y/n to the supply closet.

“That’s what I’m saying, yes” y/n says as she hides her now red cheeks behind the shelf.

“So oblivious” y/f/n scoffs before walking back to whatever she should actually be working on.

“Tom?” Y/n asked, waving a hand in front of his face.

He shook his head rapidly as he began blinking to stop staring at her, “sorry”.

She giggled and shook her head, “it’s okay, are you alright?”.

“No” he admits, sighing.

“What is it? What do you need me to do?” She asked quickly.

“It’s not that….I'm afraid I can no longer keep this professional situation going” he muttered.

“Oh” she whispers, “okay. What did I do though? If it was because I came in three minutes late last Wednesday, I-“.

Tom smirked and shook his head as she rambled an explanation due to misunderstanding his statement.

He grinned to himself as she tucked her hair behind her ear as she continued talking.

Tom felt a strong pull and instantly wrapped his arms around her waist to get her closer.

He looked down at her now closed lips before looking back into her eyes to see if she was okay with where this was going.

When he felt assured she wasn’t against it, he pressed his lips against her’s softly.

Tom smiled as he felt her lips start moving in sync with his after a few seconds of surprise.

He rested his forehead on her’s when they pulled back.

She blinked slowly up at him, “You kissed me."

"You kissed me back” Tom pointed out with a smirk.

“And I'm not here to apologize." She smirked back, tangling one hand in his hair.

“You need to stop doing that” he purrs, closing his eyes.

“Hmm, why?” She asked, and while he hadn’t opened his eyes yet he could hear her teasing tone as he tightened her hold on his hair.

“I think I wanna do a little more than just kiss” he admitted with a groan.

Before y/n could respond, there was a knock at the door, making the pair separate instantly.

Tom rubbed the back of his neck as he walked to answer it.

“No, no, let me. It’s my job “ y/n laughed nervously, desperately trying to find ways to ensure the guest didn’t know what had happened seconds before.

“Oh, Uhh.. right “ Tom agreed, sitting back at his desk.

Y/n straightened herself out before she opened the door and let Tom’s brother Harry in, offering him a kind welcome.

From that day on, y/n decided she had the upper hand and would utilize it.

It was not her first rodeo teasing men with their desire, so she knew just what to do.

As she walked into his office again, she smirked as she saw him reading his script.

He looked up and gave her a shy smile before going back to reading.

She sat down in her chair across from him, making minimally provocative sounds as she rubbed her neck as if it hurt.

Tom glanced up from his script as he tightened his grip on the packet.

He forced himself to focus back on the next line he had to memorize.

But he soon found himself distracted yet again as y/n moaned as she stretched.

“Y/n” Tom warned, seeing the teasing shine in her eyes.

She raised an eyebrow at him In feigned innocence as she raised her arm to stretch more.

As she moved her arm across her body, it pressed her breasts up further, exposing more skin, as she made another moaning sound.

Tom glared as his grip crumpled the edges of the papers in his hands, “Would you be quiet? l'm trying to work"

“I’m not doing anything Tom “ she said quietly.

He rolled his eyes, “don’t tease me”.

“I would never do that” she scoffed with a faint smirk as she let him get back to reading his script.

“Are you ready?” Y/n asked, stepping into his office as she tugged her dress down a bit.

“Yeah, I just need to g-“ Tom choked, his eyes widening as he faced her.

He couldn’t hide the way his eyes lowered to her chest, then to the slit leading from her thigh to her hip, then back to her lips.

“I'II take it that you like what you see” y/n winks, spinning so he can see the low cut back.

Heavily breathing, Tom whispers “I am not affected..."

Y/n giggles, walking to him and placing her arms on his chest, “no?”

Tom glares at her before he caves and pulls her to him, his lips aggressively moving against her’s.

He pulls back suddenly, his eyes scanning her features, “Do you want to do this?”

Instead of responding, she simply pulls him against her, her lips passionately pressing on his as she licks his bottom lip.

When they pull back, y/n smirks at him, “not affected huh?”.

He groans, looking away from her eyes, “fine, I’ll admit the dress is making this hard.”

“This or you?” She teases, biting her lip.

“Ha. Ha. You know, I would prefer you naked, but that dress also looks breathtaking on you” he admits, his hand resting on the dress material right above the slit on her hip.

She bites her lip harder as she stares at him, unable to speak.

"I can't wait until we're done with this event. There are so many things I want to do to you right now” he mumbles, eyes tracing her body again.

“Y/n?” Tom grinned, as she silently stared at him.

“The way your eyes get darker when you get aroused, is making me lose my mind” she whispers.

Tom chuckled, pulling her hip closer to him and leaning down to press a teasing kiss to her neck just below her ear., “Want to find out what we can get away with before someone comes looking for us?"

She took a shaky breath, “I will get in trouble if you’re not on time”.

Tom hummed, interlocking his hands behind her back, “fairly certain I will not get you in trouble love”.

“No trouble? Not even a little?” She teased, licking her lips and playing with his tie.

“You know l'm holding back from fucking you over this desk, don't push your luck” he grumbled, pressing his face into her collar bone.

She ran her hand down his chest with her bottom lip in between her teeth.

Tom groaned, grabbing her hand with his, “Stop being so hot please, l'm trying to get my work done”.

She chuckled, stepping back to give him some room, “Says the one who was just trying to get me to allow him to skip the event”.

Tom sighed, “You said the fans won’t be there for another hour yes ?”

Y/n nodded, playing with the necklace resting just above her bust.

“Well if we won't be missed for awhile, we should take advantage of that." Tom winked, stepping closer to her.

Tom’s hands went around her again, this time grasping her hips as he lifted her slightly off the ground.

She gasped and clung to him as he carried her to his couch.

Tom gently laid her down before hovering over her.

Y/N’s eyes lowered to his button up shirt, her fingers playfully toying with the buttons.

Tom dipped his head and began placing open mouthed kisses along her neck.

He started at the bottom, just above her collar bone and worked his way up, savoring the feeling of her skin and scent of her perfume.

Y/n began unbuttoning his dress shirt just as his lips pressed on a sensitive spot just below her earlobe.

Tom smirked against her skin as he felt her body twitch under him and a small gasp left her lips.

He opened his mouth more and began to suck on the tender point.

“T—Tom” she moaned, tugging on his hair to pull him back before he could leave a mark.

However, that only made him even more turned on, his lips now buzzing against her skin as he hummed.

As his cold fingers pushed up the hem of her dress, he lifted his gaze to look at her face.

He nearly moaned as he saw the lust in her eyes, “love, your eyes are already saying yes, now I just need your mouth to tell me the same."

Y/n grinned and whispered “yes, now.”.

Tom smiled, holding her waist, “Turn over, love."

Y/n complied, Tom’s hands assisting her spin around.

Tom delicately lowered the zipper on her dress, his lips coating the newly bare skin.

“God, love, you’re so soft” he breathed against her skin.

Y/n smiled into the padding of the couch under her as Tom lowered the shoulder straps off of her body.

She reached back, her hand blindly finding his upper thigh.

Tom groaned, glancing down at her hand before going back to the task at hand.

Y/n stretched her arm until her hand cupped his bulge through his dress pants.

He moaned loudly and dove his head down to her shoulder, his lips pressing hard against her upper spine.

“Shhh, you gotta be quiet or we're gonna get caught" y/n warned, moving her fingers to undo his zipper.

Tom quickly helped in removing his pants, lowering them enough to be out of her way before towering over her again.

He gasped as she blindly searched his waist for the hem of his underwear, her soft fingers tickling his skin, “I want you. Now”.

She smirked into the couch, before spinning around to stare up at him.

“Settle” she teased, rubbing his hip before slipping her fingers between his underwear and bare skin.

Tom growled lowly as she stroked his length, twisting her fingers to squeeze his balls.

He threw his head back in pleasure, his eyes closed as he moaned her name.

“Feel good?” She asked, letting the tips of her fingers dance along his already twitching tip.

He moaned again, looking back down to smile at her.

“How good?” She asked, licking her hand before wrapping it around his length and sliding up and down.

Tom gritted his teeth as he tried to be quiet, “fuck, reality is even better than my dreams”.

“You’ve dreamt of this?” She questioned, massaging random spots.

Tom was certain his face somehow became even more flushed at the confession but nodded, “of us. All the damn time, I just- ahh”.

Y/n smirked, her own cheeks brightening, “and this is better Hmm?”

“Still just as damn gorgeous as always” he hummed, his hand lowering to her waist as he finally came back around to the task at hand.

“But- hhhhh- your hand feels much better than my own” he admitted, smirking as y/n blushed over the idea of him masterbating to the idea of her.

Tom grinned wickedly as y/n moaned when his pointer and middle fingers suddenly pushed past her underwear and dipped into her.

“Quiet, baby, the others will hear." Tom teased, his fingers roaming her walls gently.

“Please, keep going!" She begged, squeezing his length as her body convulsed faintly.

Tom moaned and felt himself twitch in her palm but complied with her wishes, pressing slightly harder against her as he trailed every inch inside her.

He noticed her smirk disappearing as she gave in to the feeling, her hand slowly sliding down his erected penis.

Tom decided to take advantage of this and flip the situation on her, hoping to make her feel as desperate as he had been with all of her teasing as of late.

“Is it good when I touch you here?” He whispered, his voice deeper as he danced his fingers over a warm patch inside her.

She closed her eyes and nodded faintly, hips lifting to his hand.

“Or maybe here?" He asked, turning his finger to the side and prompting her leg to shake slightly.

She hummed, prying her eyes open to look at him lazily, “d-don’t stop”.

Tom nodded with a wink, slowly pushing another finger into her.

He licked his lips as her hips bucked upwards against his hand, “stay still, don't move your hips."

She groaned, “I c-can’t Tom. I need more”.

Tom nodded, glancing at her questioningly.

Once she nodded back, he pulled his fingers out easily due to her arousal.

Tom drunkenly glanced up at her before he brought his fingers to his mouth, seductively licking her arousal off of him.

She fluttered her eyes as she smirked up at him.

“Shit, you taste amazing” he complimented, his eyes unconsciously dropping down to her exposed core, “I want it. I want to taste you."

Y/n hummed, as he peered back up at her for permission she dragged her eyes slowly from his face to her waist.

Tom grinned excitedly and quickly lowered his face until his nose was pressed just above her mound.

He felt his heart beating out of his chest as he rubbed her thigh comfortingly before his tongue slid down her throbbing lips.

“I knew you looked good enough to eat” he mumbled against her.

“Thomas, you take any longer and I'II do it myself” she groaned, her hip twitching as his breath teased her skin.

His wide eyes flashed up to hers before he smirked and complied, his tongue finding her entrance.

Tom hummed as his tastebuds became coated in her.

She clenched at the vibration from his pleasure and tugged on his hair.

He moaned into her, causing her to buck her hips again.

Tom firmly set his hands in her hips and pushed them back to the couch, his words muted from their proximity to her skin but never less demanding, “don’t move”.

His tongue danced around her as deep as it could reach.

As she got comfortable, Tom moved his left hand towards her chest.

He squeezed her breasts through her bra, pleased by her shared moaning.

She kept her hips in place but hooked her legs around his shoulders, using her legs to pull him closer to her center.

Tom chuckled to himself, bringing his right hand up and pressing his thumb onto her clit.

Y/n gasped loudly, slamming her hand over her mouth.

“Ahh, you like it when I fuck you like this?” He asked, pulling his mouth back to breathe.

She nodded faintly, staring at the ceiling.

“Yeah you do” he agreed, rolling his thumb in a circle, feeling her clit harden slightly in arousal.

Y/n all but screamed into her own hands, Tom smiling proudly as he watched her swollen core drip onto the couch below them.

Tom left his hands where they were but contorted his body so he could kiss her lips quickly, “what pretty noises you're making for me... am I making you feel good?"

“Tom, no one's ever touched me like this, fuck” she cried out, reaching one hand towards his waist.

He felt an immense amount of pleasure and pride at her statement, his head lowering back down to her until the tip of his tongue replaced his hand on her clit.

“Fuck- T-Too-Tooomm” she moaned against her palm, scratching at his back with her free hand.

Tom groaned, palming her warm labia.

“I need you” she muttered, tangling her hand in his hair.

Tom nodded, leaning up from her waist enough to speak, “I’m here”.

“No, not enough” she argued, pushing him back slightly.

Tom slid back, looking at her in confusion.

She grinned and placed her arms behind her to push herself up slightly, before reaching for his waist and tugging him to her.

Tom smiled but bit his lip, “I do-don’t have a-“.

She nodded, “I’m on the pill. And, I trust you”.

Tom nodded, hands resting on her hips once again as he lined himself up.

Once he heard her whispered approval as he stared at her, he desperately slid himself in.

He moaned as her tight walls opened enough to let his girth inside, “you feel so good!"

Y/n tried to giggle but it came out more as a grunt from the pressure her lower half was under.

“Are you okay baby?” Tom asked, restricting himself from entering her further until he knew she was okay.

She nodded, “jus-…ahh”.

Tom stroked her cheek, tilting her gaze towards him, “need me to stop?”.

Y/n shook her head, taking a deep breath and Tom felt her walls loosen around him but he stayed frozen until he was sure.

“You’re, yo-you’re just big Tom” she praised, hand pressed against his chest.

Tom closed his eyes and squeezed her ass with his right hand as he moaned, thanking her for the compliment.

Y/n knew he always enjoyed getting praise, so it wasn’t surprising to learn he did in fact have a praise kink in the bedroom too.

She grinned innocently up at his heavenly sculpted face, her arm aggressively dragging his waist towards her, shoving his erection further into her, “it’s incredible”.

Tom was certain he was going to die in that moment.

He’d been dreaming of this moment for longer than he’d ever openly admit.

But the way she felt was far better than anything his mind could have imagined.

She tasted so unbelievably delicious, making him crave her instantly.

And the way she would take control when he practically melted in her arms only made him even more aroused.

Not to mention that he noticed she’d picked up on his praise kink, already driving him wild.

He threw his head back so far the back of it touched the base of his neck.

“I never thought I'd hear you say that, fuck, that's hot." Tom admitted when he came back around, his eyes instantly finding her face.

He wanted to just freeze the moment, being able to feel her while taking in every beautiful detail of her face.

Y/n smirked, and opened her mouth to say something but only gasped loudly as Tom pressed himself on her until he was completely inside her.

Tom moaned as her walls clenched around him shakingly, her frantic legs moving so much it drove him upwards a little.

As she tilted her head backwards in ecstasy, Tom dove and began sucking on the sweet spot he found minutes before.

She circled her hips against him, moving his dick with her as she let him have his way with her neck until she felt a bruise might be forming from the suction.

“Tom” she moaned, nails digging into his back as he hit her favorite spot.

Tom moaned back, his hands playing with her buttcheeks as he pushed into her more; all without stopping the suction on her neck.

“Y-you’re going to- fuck-“ she breathed, intentionally clenching her walls around his length and grinning as he moaned so loud she could hear it despite his mouth being covered by her neck.

“You’re going to leave a mark” y/n warned, dragging her nails across his sweaty chest.

“Mmmm” he nodded, sucking harder.

“I want to give you a hickey” Tom explained, licking her skin to relive some of the pain he figured she’d feel.

“So everyone can see how I feel about you” he added quietly, his arms firmly pulling her ass towards him, her hips slamming upwards into his.

They both moaned loudly, forgetting they needed to stay quiet.

Y/n shook her head, politely pushing his head from her neck, “we have an event tonight”.

Tom shrugged, a side smile and wink being sent her way.

Y/n rolled her eyes, “people will talk. Besides, it’s my turn”.

Tom sighed at her argument but lifted an eyebrow at her last remark.

She grinned and lowered her hips, shoving him off of her by his chest.

Tom’s back hit the edge of the couch, his arms slamming into the seat to stable himself.

As his eyes widened and he licked his lips, y/n stood up and walked to that end of the couch.

Tom’s eyes traced her entire body, his length twitching against his stomach as he waited to her next move.

She grinned down at him, towering over him and giving him a soft kiss which he desperately followed, his head moving towards her as she pulled back.

She reached over and grabbed his underwear from the floor, flirtingly tossing it back at him with an evil smirk.

His mouth dropped and he audibly scoffed.

“We have to get going” she winked, grabbing his pants next.

Tom growled, reaching for her, “Get back down here, we're not done yet."

Y/n chuckled and bit her lip to suppress the moan trying to escape her lips at his orders.

She turned to look at him, more than pleased by the desperation in his eyes as he laid there before her in the corner of the couch in his office.

Never did she think she’d be in this situation.

Sure she’d been with other coworkers before, but not Tom- her boss- and not in his office.

She wished for this many times, but never imagined he’d be sitting there looking so drunk off of her and like he’d give her the world if she asked for it.

She bent down, her ass just out of reach, as she put her heels back on after having kicked them off earlier.

Y/n watched his eyes plead with her as he palmed himself aggressively, his facial muscles struggling to keep an authoritative expression.

As she rose back to standing, she licked her lips and strutted closer to him.

She stopped just before him, smirking at his eyes snapped to her’s and silently screamed for her.

She kneeled over his waist on the couch, her calves pressed against his outer thighs as her feet and heels dangled loosely off the edge.

Tom moaned, rubbing himself so hard the skin burned.

Y/n smirked again and tore his hand away from himself, “that’s not your’s”.

Tom eyes froze and stared at her as his hands reached for her waist.

She curves both hands around his swollen dick, one thumb rubbing the tip and the other rubbing his base.

Tom whimpers under her touch, his back pressing into the couch cushion more.

Y/n proudly smiles to herself before tilting her head down and kissing his collar bone, her fingers still pleasingly teasing him.

Tom rested his head against the couch and closed his eyes, squeezing the couch material in his fists.

Y/n lowered her head in a tauntingly slow pace, Tom visibly squirming for more friction.

She moved one hand from his dick to his thigh, holding him in place.

“Faster! Please, let me cum!" He begged, cupping her face as her tongue danced between his tense abdominal muscles.

She smirked against his chest, twisting her hand that was still on his cock, “soon”.

Tom moaned, throwing his head back again as she tasted more of his chest while his hands tangled in her hair.

He nearly jumped out of his seat as she placed an open mouthed kiss against the skin just above his dick still in her hand.

His eyes shot open and he bit his lip hard as he looked down at her, not wanting to beg her to suck him off, especially this early into their real-whatever this was to her.

However, he could have sang her praises when he noticed she was already planning on doing that.

She licked her lips as she examined his cock, his sperm already dripping faintly from the tip in anticipation.

Y/n hummed, peering up at him as she slid off his lap and onto the floor, her hand moving to pull his hips towards the edge of the couch.

Tom eagerly scooted his butt to the edge of the couch, his legs opening wider as her hands trailed up his inner thighs.

Y/n looked at him through her eyelashes before licking her lips again and looking back down.

Tom moaned louder than he recalled ever having done before as her swollen lips surrounded his cock.

His hands found her hair again but he tried to hold back from tugging her closer to him, wanting her to take whatever time she needed to adjust.

Y/n resisted the urge to gag as she pressed her head into his lap further, his dick hitting her tonsils aggressively.

Her lips quivered slightly but she quickly recovered, her tongue licking lines up his length as she pursed her lips together.

Tom moaned, slamming his face into the cushion beside his head to silence himself.

Y/n laughed, the action shaking his cock in her mouth, making him moan again, his hands tearing at her hair now.

She pursed her lips into a tighter hold, sucking in air, his cock throbbing against her tongue as Tom sank into his seat.

“You like that?” She asked, pulling back just as she felt he’d cum.

Tom assertively nodded, stroking her cheekbone, “so damn much darling”.

Y/n smiled proudly, her fingers trailing over his wet lap teasingly.

“Mmm, come on love” he begged, his eyes heavy

“I like you begging” she admitted, Tom groaning as he pulled her closer by the grip he still had on her hair.

“Open your mouth for me, baby" he asked, tilting her head towards his lap.

She looked up at him, her mouth wide open.

Tom groaned and shook his head at her painful teasing, “fuck, please”.

Y/n laughed at him but nodded, her hand moving his dick until it was in the spot she wanted.

Without any further warning or teasing, Tom found himself in her mouth again.

He moaned as she let her tongue explore him as her hands held his testicles.

When she began bobbing her head, her lips and suction moving around his dick fearlessly, he felt himself tense.

“Love, I’m.. I’m going - darling-“ he rambled, incoherently.

But y/n knew what he was trying to say and nodded, her head not leaving his trembling cock as she began sucking harder.

Tom leaned back as he let himself relax knowing she was okay with him cumming in her mouth.

However, he soon desired to be able to watch her pretty face suck him off; and found himself pushing himself up enough to see her.

She lifted her head, her lips moving to the top of his dick and let just the edge of her teeth glance over his tip before aggressively slamming her mouth back down his length.

Tom moaned loudly, his previously broken record shattering as he felt the most intense orgasm take over his body.

He let himself explode inside of her mouth, pleasantly impressed as she simply licked it from his cock without choking.

Tom hummed as she swallowed around him, his hands holding her hair again, this time pulling it out of her face so he could see her.

“Holy fuck y/n” he praised as she finished licking him clean.

She grinned at him as she rocked herself back from his open lap, licking the few drops of his semen from her lips without breaking eye contact.

Tom shook his head, his heart beating out of control, “god you’re amazing”.

She winked, “thank you, Sir.”

Tom froze at the nickname leaving her mouth, his grip in her hair tightening in reaction.

Y/n noticed and wiped her mouth with the back of her hand, “amazing enough for a raise?”

Tom saw the playful look in her eyes but nodded affirmatively, “whatever raise you’d like, fuuuck”.

Y/n laughed loudly, standing up with a shake of her head, “how about we get to that event Hmm?”.

Tom furrowed his eyebrows at her as he watched her grab her underwear from the floor.

“You didn’t cum yet” he stated simply, pushing himself off the couch.

She shrugged, stepping into her panties as she tried to reassure him “I did have an orgasm though, so it was better than most hookups”.

“Hey” Tom whispered, spinning her around by her waist.

She finished raising her underwear before looking up into his eyes and nodding.

“Love, you know this-“ he said, looking around the room, rubbing his neck shyly.

“Tom, it’s okay, it doesn’t have to mean anything” she told him, his lips curving into a frown.

“What?” He asked, grabbing ahold of her wrist.

“This isn’t my first one night stand Tom” she giggled, kissing his cheek, “I know it doesn’t mean anything to you. It’s not a big deal”.

Tom wanted to scoff and pull her to him, kissing her until she understood just how wrong she was.

Instead he sighed, scolding himself for acting on his feelings so primally that she misinterpreted what the moment meant to him.

He had wanted to ask her out and take it slow, letting her have time to be comfortable dating her “boss”.

But when she walked into his office the way she did, he couldn’t think clearly any more.

She smiled at him softly and kissed his cheek again as she stepped back and grabbed her dress.

Tom stood frozen as he watched her slide the dress back on, the material instantly clinging to her body.

His mouth watered but he swallowed and opened his mouth to try and explain.

However, she spoke before he could, “can you zip me?”.

Tom nodded slowly, carefully sliding the zipper up from her tailbone.

“Wait, one more” y/n giggled, wiping the tissue against Tom’s neck as she removed another lipstick stain.

Tom silently let her work, his frown still present.

Once she knew he looked fine and there were no more signs of their scandalous behavior on his body, y/n stepped back and sighed.

“Why are you so pouty?” She groaned, rolling her eyes, “if it wasn’t for your cum painting my esophagus earlier, I’d think you didn’t enjoy what we did”.

Tom blushed deeply, “it’s just… you… you didn’t-“.

“Cum? I know, you said that already Tom” she laughed, “but again, I’m fine. Besides, I promise if that changes I’m more than capable of taking care of myself later”.

Tom shook his head in frustration over the fact she misread what he was going to say but then scoffed as he realized her second statement.

“If that happens, I deserve the chance to make up for it” he argued, “let me take care of you if that happens”.

“There’s nothing to make up for Holland” she rolled her eyes, resting her hands on his chest as she adjusted his tie, “most guys don’t make me cum”.

“Your boyfriends have never-?” Tom gasped, looking into her eyes to see if she was simply trying to make him feel better.

She shrugged with a small laugh, “they have Tom. Never thought I’d have this conversation with you, but yes my exes… well, most of them, have made me cum at some point. I just meant it’s not that often”.

Tom huffed, “then they need to be putting in more effort. You deserve-“.

A knock came from the door, making both of them freeze.

“Tom? Y/n? What’s taking so long? The guests are waiting” Tom’s friend Harrison shouted through the locked office door.

“Coming!” Y/n assured him, dropping Tom’s tie into place and stepping back.

“Well that’s ironic” Tom joked, grabbing her hand.

Y/n gasped and smacked his arm, shaking her head as a small laugh left her lips.

Tom smiled and pressed his lips to her temple, “one last thing before we go”.

She paused and turned to him in confusion.

“You really do look divine y/n” he complemented, squeezing her hand.

She cursed herself for actually blushing over the compliment given what they’d just finished doing.

Tom smiled and tugged her towards the door.

“Mate, god, could you stop for like one day?” Harrison groaned, shaking his head at Tom.

“Stop what?” Tom asked, glancing over at his friend.

“Eye-fucking her” Haz laughed, nodding towards y/N’s direction as she talked to one of the guests.

“I-I’m not eye fucking her Harrison” Tom defended.

Harrison rolled his eyes, “the hell you’re not. Mate, you’ve had a crush on her forever. You’ve been in love with her for at least a few months now, everyone can see it”.

“Really?” Tom asked, his eyes darting back to y/n, his heart speeding up as Kolby put his hand on her back.

Kolby was one of the guys Tom knew y/n had seen.

He wasn’t sure if they dated, her never wanting to discuss such matters in the office, but he knew they’d at least been together.

Tom knew he shouldn’t care, especially since he had now been with her as well.

But Tom wanted more than that.

He wanted to be the last one she was with, the only one she was with.

Tom knew this much to be true even before tonight.

But she made it clear she did not see tonight’s events the same way he did.

So all he could do was toss back his drink as he tried to calm himself down.

“Yes really. Fuck even when I point it out, you don’t stop staring” Haz laughed, shoving Tom’s shoulder.

“Everyone can tell?” Tom clarified, his heart pounding in anticipation.

“Duh” his friend teased.

“Even… even y/n?” Tom asked, breaking his eye contact with the scene across the room from him.

Harrison stopped laughing and set his hand on Tom’s shoulder, “mate, I don’t know. Probably, I don’t see how she couldn’t by now”.

Tom shook his head, “I need a drink”.

Harrison sighed, stepping around his friend to block him from moving, “you’re already drunk off y/n, so nice try”.

Tom groaned, his eyes flickering to y/n across the room; her smiling as she looked his way.

He forced a kind smile in return but it fell instantly as Kolby dropped his hand lower on her back as she talked to some woman.

“Mate” Harrison laughed, waving his hand in front of Tom’s face as his eyes traced where he was looking.

“We-we-“ Tom muttered, his conscious stopping him from confessing, but his predicament and lack of focus fighting to blurt it out.

“You what? Tom just make a move, she’s probably interested in you too. Just ask her out” Harrison encouraged.

“I can’t “ he argued, the tension in his chest doubling as Kolby’s hand dropped to y/N’s ass.

Harrison began talking but Tom’s attention was stuck on y/n.

He watched as y/n turned to Kolby with a confused look on her face, politely stepping out of his embrace until his hand wasn’t on her butt anymore.

Tom smirked to himself as Kolby froze in surprise.

However, Kolby wasn’t giving up.

So he moved forward when the woman they were talking to left, his hands grabbing y/N’s hips.

Even from across the room, Tom could see Kolby’s thumb intentionally resting on the exposed skin of her thigh.

Y/N’s eyes flickered as she looked back to where she last saw Tom, her eyes locking on his before she faced Kolby and picked his fingers off from her.

“Excuse me” Tom murmured, moving in her direction, not having heard any of Harrison’s comments.

“Mate!” Harrison laughed, blocking him again, “just ask her out so you two can date already”.

Tom glanced over and saw y/n was okay and back to talking with guests so he returned his focus to Harrison.

“You said you think everyone knows, even her” Tom sighed, “if that’s true… I already know her answer”.

“Shit Tom, why the low confidence?” Haz scoffed.

Tom shook his head, he wasn’t having low confidence.

In fact, he felt on top of the world after the moment earlier.

Especially considering it had been with y/n.

But despite his confidence, he allowed himself to realize if Haz were correct, she only wanted to sleep with him.

If she knew Tom liked her the way he did and was interested in him the same way, she wouldn’t have called their lovemaking a one night stand.

“Thomas” Harrison complained.

“We slept together” Tom blurted causing Harrison’s eyes to nearly spike up to his hairline in shock.

“Shit, tonight huh?” Harrison grinned, “that’s what you looked so happy about this event! You weren’t happy, you were satisfied”.

Tom growled but nodded, “but she called it a one night stand”.

Harrison sighed and nodded slowly, scratching his neck, “oh… geez… I’m sorry mate…”

Tom bit his lip and sighed, “it’s fine. Don’t get me wrong, I love that she even looked at me that way… I just…”.

“Wanted more” haz concluded for him.

Tom nodded once in agreement, letting his eyes roam to where she was, “so much more”.

“I mean normally one has to push their mates to keep finding ways to try and hook up with someone, but since you’ve already done that” haz smirked, earning a shoulder punch from Tom, “in this case I’m going to push you to keep trying to get her to be interested”.

Tom glares at him protectively, “I’m not going to force her to date me and I’m certainly not going to trick her into it or into being into me”.

Haz smirked at Tom’s sudden change of tone, glad he wasn’t sulking anymore, “just saying you should let her know how you feel”.

Tom stared at Harrison silently.

“I know, but maybe she didn’t see it the way everyone else did. Maybe she just thought you wanted to simply sleep with her” haz shrugged, glancing over at y/n, “can you blame her? Most of the guys here want to get with her just to say they did”.

Tom grumbled to himself and while Haz couldn’t make out what he said, he was sure it was something about y/n being worth more than the sexual target of the office complex.

It wouldn’t be the first time he made such a remark, Harrison often laughing and positioning out they were in an office building with a ton of stuck up celebrities and their assistants so it shouldn’t be a surprise.

“How about a drink for confidence?” Haz asked, grabbing a glass from the waiter who roamed by them.

Tom took the glass from him, tossing it back and letting the alcohol burn his throat.

He sighed as he realized he could still taste her, so much so he could hardly taste the alcohol; as if his mind was stuck on every lingering detail of her.

“Okay” Tom mumbled, shaking his hands loose at his side’s nervously.

“Hey Tom…” y/n whispered, appearing behind him, Haz smirking at Tom as he turned around.

“Y/n, love, you alright?” He asked, setting his glass down on the nearby table and reaching for her hand.

She smiled softly, raising her hands until he grabbed ahold of them both and squeezed.

Tom stared at her silently, looking over her stressed features as he allowed her time to breathe before explaining why she looked so worried.

“I’m okay, I…” she mumbled, glancing behind Tom’s shoulder at Harrison.

Haz got the hint and smirked as he shuffled out of the area when Tom followed her eyesight.

“What is it?” Tom asked, tugging on her hands so she stood closer to him.

She glanced up at him before hesitantly letting go of his hands and snaking one arm around his waist.

He watched intently as she looked up at him for approval as to if she was okay.

They’d been closer than colleagues before tonight, practically best friends, minus the big secret desire between them.

So this behavior wouldn’t be unusual to the guests present but Tom suspected she was uncertain where they stood after what happened a few hours ago.

He nodded and smiled down at her, his hand softly resting on the covered area of her hip as she relaxed into his side.

“Did you tell Makayla?” Y/n asked lowly, biting her lip.

Tom shook his head instantly, “course not, why?”

Y/n glanced across the room towards the woman in question who was about a year older than y/n.

Y/n knew that Tom and Makayla had slept together at some point in the last year, and suspected the woman’s behavior towards her tonight was out of jealousy after hearing what y/n had done.

“Love? Are you alright?” Tom asked, rubbing her hip calmingly.

“Sorry, yeah” she laughed breathily, “it’s just Jake and her are being assholes more than normal tonight”.

Tom glared over in the direction of the two in question, his hold on y/N’s waist tightening and pulling her closer unintentionally.

Y/n felt her heart surge at the behavior, mentally questioning if it meant he cared for her more than just a one night silt and or if he was just being possessive after this evening.

“What happened?” Tom asked her, turning back to look at y/n.

“Jake hasn’t left me alone tonight, being far more interruptive than normal” y/n rolled her eyes before looking over towards Makayla, “and she seemed jealous or something tonight is all”

Tom nodded, “there’s nothing between us. It was one drunken night after I lost that audition. That’s all, so I doubt it. She told me she is trying to make her way through the office”.

Y/n laughed loudly, covering her mouth with he free hand, making Tom smile.

“She actually said that to you?” She laughed.

Tom nodded and shrugged, “it’s fine, I didn’t have any feelings for her. But I’m just saying she’s not likely jealous about that, plus I didn’t say anything”.

“Hmm” y/n hummed “crazy she actually is doing that, whereas I have a few office flings over the years and suddenly I’m the office sl-“.

Tom stiffened, stepping back to stand in form of her, holding her in place before him as he looked into her eyes, “ don’t finish that”.

Y/n blushed but gave him a soft laugh and shrugged, “it’s what everyone thinks”.

“No it’s not. Not me” he argues, eyes staring into hers.

“Thanks Tom, but I don’t really care. Plus, it doesn’t say anything about you, even after tonight” she assured him, rubbing his bicep kindly.

Tom glares at her, removing his hands from her shoulders to cross his arms against his chest, “stop “.

Y/n raises an eyebrow at him, confused by his serious demeanor, “I promise. I’ve been with like two others here, most people know that but it just gives them something to gossip on without Makayla trying to slander them in revenge. But, it won’t taint your image or-“.

Tom groaned, rubbing a hand down his face, “my god. I don’t fucking care y/n”.

She froze and stared at him in shock, him never having used that kind of language with her in such a serious way.

He noticed her body language and sighed, dropping his arms to his side as he took a deep breath, “I’m sorry. I just mean, I don’t care love. Okay? I’m pissed they’re gossiping about you, especially when I’m the one who slept with more people”.

Tom looked across the room, glaring at each of their semi-coworkers he suspected participated in the rumors.

He turned back to y/n, delicately grabbing one of her hands, “but I don’t care what it says about me. Even if it were true. I don’t care because I… tonight was….”.

Y/n looked at her heels and nodded slowly.

Tom felt hopeful it was a signal she misinterpreted his words, wanting to take it as a sign she was secretly disappointed when thinking he didn’t take tonight seriously.

As such just as she began to mumble something about understanding, Tom took a chance and held up one fingers pressing it against her lips.

Y/n slowly closed her lips, her top lip staining his finger red as her lip brushed against it.

Tom glanced around, hating there were so many people present for a moment he envisioned being private.

However as he looked back at her and saw the hope and fear fighting in her eyes, he ignored that thought.

“I was not done” Tom states, lowering his finger back down and tugging her closer with his other hand.

“I was going to say, I’m…” he took a deep breath, focusing his gaze on her eyes in an attempt to communicate his sincerity, “I’m in love with you. I was going to say tonight wasn’t just a hook up for me… or at least I hopped it wasn’t”.

Y/n froze in place her eyes boring into his as she took shallow breaths.

“I know it’s a lot. You don’t have to respond, nor do you need to feel the same” Tom mentioned, softening his hold on her hand.

“I apologize for making our profession relationship complicated and I.. oh god, I totally overstepped. I know I asked if you were consenting beforehand… but as your technical boss, I should’ve handled it differently “ Tom rambled, squeezing his eyes shut, “I mean I never saw myself as your boss, rather as a friend. I mean Haz is my friend and he was my personal assistant for awhile… oh fuck, I’m making this worse”.

Y/n pulled herself together as Tom kept rambling about him being sorry and that he should’ve made his feelings clear before sleeping with her and that he didn’t want to make her feel uncomfortable or violated.

She smiled as she digested his confession of being in love with her; shocked he felt the same way she had for months now.

“Tom” y/n whispered, Tom shutting up instantly and fearfully looking back at her.

“I’m in love with you too. Not because you’re my boss, but because you’re you” she admitted, slowly placing her hands on his chest so he could move away if he wanted.

Tom’s bottom jaw parted from his top jaw slightly before he broke into a wide smile as his cheeks reddened.

“Seriously?” He laughed, “shit I should’ve acted sooner then. I’ve been in hell for nearly a year”.

Y/n gasped, tugging on his tie to bring his face down to her level more, “a year?!”

Tom shyly looked away as she bit his lip.

Y/n smirked, pulling him the rest of the way to her by his waist, his chest now pressed against hers.

“Yes, you should’ve acted earlier” she whispered so lowly he struggled to hear her over the background music and surrounding conversations, slinging one arm over his shoulder.

Tom bit his lip aggressively, his hands on her waist as she pretended they were dancing but he knew better.

She smirked at him as she lowered one hand to his waistband, “I mean seriously, you had to keep me waiting this long?”

Tom chuckled, moving one hand to pull her head against his shoulder as he whispered into her ear, “I’ll make up for it”.

Y/n smiled into his shoulder, walking her fingers over the middle seem on Tom’s pants.

Tom moaned quietly into her ear, “easy now love”.

She shook her head against him, sliding one finger in between the flaps of fabric buttoned together over his crotch, “you love me, don’t you?”

“If you don't stop darling, I've no other choice but to take you right here and now against the wall there” he warned, looking to the closest wall.

Y/n lifted her head from his shoulder, slyly removing her finger from its place over his underwear.

She looked around and smiled at him before walking away.

Tom sighed, his eyes glued to her shifting hips and the way her ass moved as she strutted away from him.

He nearly headed her way when he saw Kolby approaching her.

Sure she admitted she was in love with Tom, but that didn’t mean he enjoyed the idea of her ex being all over her.

However he stayed where he was when he saw Y/n shake her head, say something to him, and he sulked off.

Tom smiled to himself, burying his hands in his pockets as he waited to see why y/n left his side suddenly.

He laughed as she grabbed a brownie from the dessert table and spun back.

She grinned at him as she bit into the dessert on her way back.

Tom rolled his eyes playfully, removing his hands from his pockets and resting them on her hips when she was close enough.

Y/n shrugged, taking another bite and smirking as Tom stiffened when she licked the crumbs from her lips.

She spun the last bite in her fingers for a second, glancing up at a confused Tom.

She wiped the frosting off the top of the brownie, slowly chewing on the remainder.

Tom glared as she smirked at him knowing how hard he was getting already.

She began to lick the frosting from her finger teasingly before she ran the finger across his white dress shirt.

“Oh, I’m sorry” y/n smirked, “Your shirt got a little dirty, how about we go take it off?"

Tom smirked, his eyes glowing as he firmly grabbed her hand, leading her out of the event center.

“Tom, where are you going? The fans are just arriving” Harry stated as the couple entered the hall.

Tom groaned, “y/n is.. I got my shirt dirty, I need to change”.

Baz sighed, shaking his head, “fine, you’ve got probably five minutes anyways. If that. Y/n please ensure he actually hurries, Harrison said he was already late tonight”

Tom blushed, his fingers dancing over the back of y/N’s hand at his side.

“Of-“ y/n began but Harry cut her off.

“You know, he’ll kill me for saying this, but normally when you’re here he’s actually on time, probably trying to impress you” Baz smirked, “so maybe now he’ll arrive when the fans get in”.

Y/n giggled, “Harry!” biting her lip to keep from smirking instead of pretending to brush off Harry’s comment the way she normally would prior to Tom’s confession, “I’ll take care of it”

Tom griped to himself as y/n got a shirt out of the closet in his office.

She always had at least one extra suit and one extra set of standard clothing in the office closet so that if Tom had a sudden meeting, event, or wanted to go for a walk without being noticed, he could without having to go back to his house first.

He pouted as she tossed him the other dress shirt, not turning to look at him as she requested the dirty one so she could put it in the dry cleaning bag.

“Y/n” Tom whined, making her turn around and laugh at him.

“Tooomm” she teased, hands on her hips as she walked to him.

“We had plans, screw Harry” Tom stated.

“You want me to screw Harry?” Y/n joked, “what weird ass situation did I get myself into”.

Tom glared and scoffed, “not like that, and you know it”.

She giggled, grabbing the shirt he finally removed, kissing his cheek before she left.

“People will know if you’re late again Tom” she warned, tossing the shirt into the bag and zipping it closed.

“So, let them. I’ll tell them myself, I told you I’m in love with you” he reminded her, buttoning up the fresh shirt she gave him.

Y/n set the dirty dry cleaning bag on the back of his desk chair so she would remember to take it in for cleaning later.

She smiled over at him, tucking hair behind her ear, “doesn’t mean they need to know we’re fucking in your office”.

Tom nodded in agreement, not wanting the other men to be thinking of her in that way.

Y/n approached him, helping him with the rest of his buttons and then his tie, “not saying I don’t want to fuck in your office”.

Tom chuckled, pulling her waist to him as he pressed his lips against hers in a needy manner.

The kiss got heated just as y/N’s timer on her phone went off.

Y/n groaned as she and Tom pulled back.

He grinned at the way her eyes still held his with a burning passion.

“I will take care of you soon love” he promised, kissing her softly before departing from her arms.

Tom smiled at the fans as he autographed the headshots his agency had printed for him for the event.

He glanced over at y/n, trying not to laugh teasingly as she shifted in her seat uncomfortably.

“You alright love?” Tom whispered in between fans.

Y/n glared over at him, wordlessly sliding another print his way to sign.

He grinned and placed his spare hand on her thigh under the table.

Her eyes snapped to his with a warning stare but he ignored it, rubbing her inner thigh slowly.

“Ello” Tom greeted the next fan casually, as if he wasn’t trying to edge his personal assistant under the table.

The fan squeaked and thanked him for signing the picture.

Tom smiled innocently as he thanked her for attending, his hand secretly never leaving y/N’s leg.

Over thirty minutes passed this way, Tom’s hand taunting y/n under the table as she tried to keep her composure.

Tom painted on yet another fake innocent smile when a fan asked for a photo.

However, his eyes darkened and widened as his fingers hit something wet this time.

He instinctively curled his fingers, causing y/n to grip the sides of her chair firmly in an attempt to stay still as her thighs shook under his touch.

Tom closed his eyes, claiming it was him blinking When the fan took the photo.

He removed his hand slyly, needing to compose himself for the photo.

Once the fan left, he glanced over at y/n, a faint smirk showing more in the glimmer in his eyes than on his lips as he whispered a warning , “y/n”

She looked away in annoyance and slid another paper to him.

Tom laughed and signaled for Harry to let the next fan approach.

“You alright love?” Tom chirped as he rounded the corner.

Y/n had stepped away from the table several minutes prior so once the last fan left, Tom sought her out.

She ignored him as she shifted her thighs, rubbing them together to relieve the tension between her hips.

Tom smirked, walking over and grabbing a hold of her hips firmly, “what is it you’re doing Hmm?”

Y/n rolled her eyes, “as I said early, I’m able to take care of myself”.

Tom shook his head, pushing her backwards until her back was supported by the wall, “still so horny? Even after I fucked you so well earlier?”

Y/n moaned as his warm breath hit her ear and his erotic words echoed in her mind, “yes”.

He pressed a firm kiss to her neck, just to the side of the spot he knew she desired, “I said I'd take care of you, did you think I wouldn't follow through on that?"

She shrugged, making him glare as he tightened his grip on her, one hand dropping to squeeze her ass as it pressed against the wall.

“Hmm, well maybe I’ll just have to show you I’m a man of my word then” he whispered, moving his mouth to her sweet spot.

Y/n moaned, gripping him desperately, “We're really going to fuck here? What if someone sees us?"

Tom laughed, “you’re the one who can’t seem to wait love”.

She took a shaky breath, “I can too”.

He shook his head at her stubbornness, “the grip you have on my shirt, and the placement of your other hands says differently darling”.

Y/n glanced down and blushed as she registered her hand roamed down to press against the bulge in his pants.

Tom licked her neck slowly, “don’t be embarrassed love, it’s hot how needy you are for me”.

Y/n fought to compose herself, not willing to be so submissive immediately.

She leaned back against the wall, making his lips separate from her neck, much to her disappointment but she knew it was needed.

“I’m not needy” she remarked, crossing her arms to increase the distance and allow herself to be more believable when the tempting contact broke.

Tom raised an eyebrow at her, “please, darling, you were basically begging”.

Y/n glared weakly, “I don’t beg”.

He smirked at the challenge, “wanna bet?”

She smirked back and nodded, “Loser pays for the date tomorrow”.

Tom agreed despite knowing he was going to pay regardless, especially since he’d suggested the date to begin with.

“Who is the one begging?” Y/n teased as Tom’s eyes roamed her exposed body, lust taking over his normally kind eyes.

“I never said I was too blind to appreciate your gorgeous body, my love” he argued, stepping back from the couch as he lowered his pants.

She shook her head, “what’s your plan then hmm?”

Tom rolled his eyes, leaning down to kiss her lips, licking them quickly, “I don’t need a plan. You’ll be begging soon, love”.

Y/n laughed but nodded, waving her hand over her body tauntingly.

He bit his lip as he undid his tie, getting an idea as he watched the way her hands went down to her core.

Tom tsked and grabbed her hand just as the tip of her fingers touched her outer lips, “no. There will be no touching. That’s cheating love”.

Y/n groaned, tugging her arm from his grip with an grin, “good luck stopping me”.

He smirked as his idea echoed in his mind, his hands lowering the tie from his neck, eyes flickering between the tie and her hands.

She seemed to catch on at that moment, eyes widening.

Tom smirked, but let his eyes soften as he looked for her consent when he grabbed her wrist.

She smiled at him and shrugged, “not going to help get me to beg, but sure”.

He scoffed and shook his head.

It wasn’t the end of his plans with her, but he suspected it would help more than she thought.

If nothing else, it would keep her hands off him which would help him not cave in to her touch before she began to beg for him.

He needed her, but he desperately needed her to beg him the way he had begged her earlier.

“Hands behind your back." Tom ordered, unbuttoning and pulling his shirt off as he waited to her to turn around.

She nodded and stood up, intentionally taking her time as she dropped her hands behind herself.

She made sure to let her hands smack against her ass as she waited to him to tie her hands.

Tom gritted his teeth as his eyes locked on the bounce of her butt under her soft hands.

Composing himself, he assertively gripped her wrists with one hand.

He watched as she squirmed slightly, her thighs rubbing, as he tightened his necktie around her wrists; pleased at how soon it had started to work.

“Now, I have work to finish” he told her, walking to his desk.

He tossed the garment bag off into the corner before settling into his seat, grinning at her across his desk.

She glared at him, “really? You’re not going to even touch me?”.

Tom smirked and shrugged, “how bad do you want me to?”

She scoffed at his pleased expression as she contemplated her situation.

“You know, you can touch me without it meaning you lost the bet” she told him.

He nodded, pretending to consider her idea.

She pouted over at him, walking over and sitting on the edge of his desk.

Tom gulped as his eyes noticed the way her bare ass was pressed against the desk, the corner making an indent in her skin the way he wanted his hands to.

Utilizing his turn on, she pressed her butt against his desk harder as she told him, “you can grab my ass Tom, you can even spank it if you want”.

Tom groaned as he saw her notice the way his cock visibly twitched.

He shook his head, ignoring her comment as best as he could as he pushed down his underwear to relieve the force compressing his erection down.

She wanted to cave as his enlarged dick flung up to his stomach, so she did the last thing she could think of in her current predicament.

“Kolby would do it” she whispered, not looking at Tom.

He instantly stood from his seat, grabbing her bound arm and pulling her up.

“What?” He asked firmly, staring at her.

“Bet or no bet, Kolby would smack my ass” she pushed.

Tom immediately gave in and brought his hand back before slamming it hard against her butt.

Y/n gasped at the contact, Tom watching as her eyes widened before being coated in a look of pleasure.

He shook his head, spanking her again, “don’t say his name again”.

Y/n nodded but when Tom sighed in relief, she added, “I’ll try… Jealousy seems to be a great motivator for you."

Tom glared at her, one hand smacking her ass again while the other gripped her inner thigh.

She arched her back as she moaned, her hands twisting in the restraints.

“I don’t want to hear his name” he replied, and while he was hiding it well, she could sense some sincere jealousy there, not just the teasing way she meant it.

“Tom,” she said, lowering her tone to a soft sound, “you don’t need to be jealous of him. Or anyone”.

Tom nodded, his hand squeezing her ass and pulling her closer.

Noticing some apprehension in his attempt to fully believe her, she bent her head to rest on his shoulder, ”I don't want anyone else. It’s you I’m in love with. Besides, no one else can make me feel like you do."

Tom grinned to himself, his grip on her ass cheek tightening as he tried to get her closer to him.

She groaned as his erected penis pressed against the outside of her outer lips in the process.

He smirked despite the growing desire in himself that risked him caving to her unspoken demand.

“Beg for it." He ordered, his thumb rubbing her mound before lowering his hand to his cock to pump it.

She took a shaky breath but remained bratty, “And if I don’t?”

Tom sighed and sat down again, “then, It's my thigh or nothing, I'm not helping you get off."

She furrowed her eyebrows at him in annoyance but took a seat on his thigh, her legs on each side as her privates rested on the muscles of his thigh.

He leaned back and watched her silently, keeping his face stoic.

Y/n scoffed and began rocking herself on him, Tom feeling her warm up against him.

He stretched, reaching his hands behind her to keep her from falling off as she increased her speed as he let out a seductive moan to entice her.

Tom’s stoic expression shifted to a taunting smirk as she moaned, her eyes closed, as she aggressively rode his thigh.

As he felt her arousal drip onto his thigh, he placed a hungry kiss to her collar bone while her head arched back.

“Fi-fine” she whimpered, tugging her restraints and whining as she tried desperately to increase the pressure on her core with his thigh.

“What’s that?” He asked, biting his inner lip to keep from touching himself or scooping up her juices.

“Fuck-“ she groaned, slamming her head forward onto his chest as his hand slipped to her and slapped her mound.

“Okay. I give in” she cried, “please give me more”.

Tom smirked, holding her head up as he looked into her pleading eyes, “I’m not sure I understand”.

She whimpered, shaking her head, “please Tommy. I can be good, I swear. I can be so good”.

Tom nodded, his head lowering to her neck as she leaned into him, “who would I be to deny you my love? But I just need to know what it is you need.”

She pushed her shoulder against him, Tom responding by helping her sit upright on his leg with her head up.

“Please! Give it to me!" She begged, the desperation clear in her voice and eyes by now.

Tom grinned in relief that he didn’t have to resist anymore.

He nodded sweetly, stroking her cheek and letting that hand trace her skin as he lowered it to her waist.

“Of course my sweet girl” he encouraged, pleased with the shock and intense pleasure that rushed over her as his first three fingers pushed into her without warning.

She gasped as he curled his fingers and moved around inside her, “oh god, yes”

He moaned, jerking himself as she clenched on his hand, “let yourself go beautiful”.

She nods once weakly before throwing her head back as she screams, Tom’s fingers firmly pressing onto her g spot.

Tom groans in discomfort as he tries to increase his own pleasure with his spare hand as he guides her through her high.

She rocks her hips against his hand, prompting him to improve the tempo and pressure of his fingers.

“Holy fu-“ she shouts, digging her nails into her own hands due to the tie, “god damn Tom”.

He removes his hand from himself as he feels her walls loosen, not wanting to finish yet.

Tom smiles proudly as she cums over his fingers, not stopping the tapping of her g spot.

She moans throughout the rest of her orgasm, leaning back as she stops cumming on him.

He quickly braces her back to keep her from stumbling backwards, “that’s it love”.

She glances down at him, lifting her legs off of him.

Y/n looks down shyly as she sees the mess she made of his fingers and thigh.

Tom winked, “you cum so beautifully my dear”

She blushed and moved towards his chest, using her thighs to push his apart.

“Words” Tom ordered, seeing the glint in her eye.

She chokes out a whine, “Tom, please, I need you”.

Tom bites his lip, his hands securing her hips as she stood before him.

Knowing he demanded more, she dropped to her knees, looking up at him.

And fuck, Tom thought that position, would be the death of him.

And a blissful death it would be.

The way her messy hair stuck to her flushed face, her hands tied behind her back with his necktie, kneeling before him, eyes begging with him, as she lowered her mouth to his crotch.

Tom threw his head back as her lips gripped his dick in desperation, her moaning vibrating against him.

It took himself several seconds into the blowjob and a near orgasm before he snapped back to his goal.

As she licked his member teasingly, he gripped her hair, pulling her back.

She groaned as she looked up at him, “I told you I could be good”.

Tom moaned, free hand pushing on his dick at her words.

“Not right now. As much as I love you letting me fuck your mouth “ he confessed, tugging her hair, “you mouth needs to be doing something else”.

She chuckled softly at his rambling prior to his order but nodded.

She lifted her thighs off her shins and pushed herself back to a standing position.

Y/n glanced down at Tom and whimpered, her eyes locking on his cock.

“How can I help you y/n/n?” Tom inquiried, dragging his hand down her shoulder.

She shivered under his touch, “please, I need you Tom. Just please help me, I’m begging, I can’t get myself off, I need you. Tom, please, please, please”.

“I told you, you would eventually start begging." He smirked, mockingly stroking her face with one hand, squeezing her ass with the other.

She arched her back slightly and moaned, “I know. You win, okay. Fuck-… Tom you win, just…”

Y/n gasped as Tom smacked her ass and pulled her hair while his eyes scanned her body.

“Please Tom, just fuck me already. I need you “ she sobbed, “I need your dick, I need you in me, please”.

He smirked and removed his hand from her tangled hair, dropping it next to his other one as he firmly cupped her ass, “god I love it when you moan my name”.

Y/n moaned as he gripped her cheeks tightly, enjoying the feeling of his hands on her butt, “Tom, please”.

Tom grinned and used the grip on her ass to pull her to him, firmly guiding her until her core was against his dick.

She gasped as his warm penis touched her.

Y/n glanced up at him with thankful eyes before she gently shook her arms.

Understanding her wish and also personally desiring her hands to be free, he whispered, “Be good for me and I’ll untie you”.

She nodded, “I - I will be good”.

Tom moved his hands to her wrists, grabbing the ends of the necktie restraining her, “promise? How good will you be for me?”

She whimpered, batting her eyes at him, “so good, Sir. Fuck, I’ll be so good”.

Tom moaned at the nickname, his fingers rapidly undoing the tie on her wrists.

Y/n sighed and tangled her hands in his hair, her lips pressing kisses all over his face.

He hummed, leaning his head back as he let her hands rover all of his skin, relishing in her touch.

“Sir, I want more, please, give me more!" She pleaded, her hands pumping his cock as precum dripped from it.

Tom’s heavy eyes met hers, “show me what you want, and beg for it, like you promised”.

Y/n nodded immediately, her hand squeezing his dick, “I need this, your enormous cock Sir, I need it in me. I need you railing me, please”.

His eyes flashed open, one hand tugging her hair and the other back on her ass again, “fuck y/n… no more sir, I need you to beg me. Not your boss. Me. Tom”.

She stepped back and pushed his legs together, straddling his waist within seconds.

“As you wish, after all, can’t disappoint the best I’ve ever had” she winked, playing into his praise kink.

Tom moaned, resecurring his grip on her and tightening his hold.

“Tom, handsome, I need you” she exclaimed, rocking her hips closer to him, “so so so badly”.

Tom nodded and groaned as he leaned against his desk chair.

“Please Tom, help me out, I need you, I can’t handle this anymore, I’d do anything “ she whimpered.

He immediately caved, hand leaving her hair to grab his girth and line it up to her.

“Me or you?” He asked her, giving in.

She grinned and sighed in relief, “I don’t care right now”

Before he could decide, she tore his hand away from himself and replaced it with her own as she aggressively pushed his dick into her opening.

They both moaned scandalously as their hands trailed each other and lips roamed the other’s body.

Y/n rode him as Tom audibly sucked on her neck, “you’re so good for me y/n”.

She hummed, making cursive letters with her hips as she lowered herself onto him further.

Tom cursed and aggressively slapped her ass as he bit her neck.

“Oh fu-“ she gasped, tugging his hair, “motherfucking hell Tom. Do that again”.

Tom smirked and repeated his actions and let out a hellaciously loud moan as she spelled his name in cursive with her hips as he kept spanking her butt.

Just as he noticed what she was spelling with her movements, he felt himself let go and finish inside of her without notice.

“Fuck, I’m s-“ Tom mumbled, leaning up and his breath hitching as his cock trembled against her walls.

She held one hand over his mouth, the other pushing him back down in his chair, riding him as he went through his high.

Tom was acutely aware of the insanely erotic sounds he was making, but kept squeezing her ass in his hands as if his life depended on it.

When he was done, his hands held onto her waist to keep himself inside her, “my turn”.

She gasped as Tom lifted them both up, her legs wrapping around him as she felt herself clench around him as he walked with his dick inside her.

“Tom” she moaned as he approached the table, them unknowingly having moved away during their erotic activities.

“Let me hear you love, no one else is here” he cooed, stroking her hair as he reached the desk.

“I don’t even care anymore, they can hear” she gushed, “I can’t help myself, you’ve ruined me Tom. I need you, please, I can feel another one”.

Tom chuckled, “oh I know. Don’t worry love, you’ll cum again”.

She whimpered at his words but moaned loudly as he slammed her back onto his desktop, his lips traveling her chest instantly.

“G-“ she gasped, scratching his bare back as he hovered over her, his dick still inside her.

“Gah, fuck Tom, no” she cried as he started to remove himself from her.

He smirked as he kept bringing his hips back for a few seconds before suddenly throwing his hips forward, making her scream his name.

“You like it when I fuck you on my desk Hmm?” He asked, grinning as she nodded wordlessly as she gasped for air.

“You just love it when I pound you like this don’t you y/n?” Tom teased, lowering his lips down to kiss her breasts as he thrusted his hips into her again.

“Fuck yes” she screamed, “please Tom, please don’t stop”

“Shit love, Your thighs are shaking so much” Tom commented, rubbing them delicately, “just let go baby”.

She whimpered, tugging on his hair, “I need your lips, kiss me please”.

He nodded within seconds, but backed his hips up, pulling himself out making her frown.

He laughed and smirked, leaning his lips down until they were mere millimeters from touching hers.

Tom thrusted his hips forward with as much force as he was sure she could handle, his mouth connecting with hers as he absorbed her loud moaning.

Tom groaned as he felt her warm cum engulf his dick in the already tight space he was working with down there.

As she continued to cum, her walls stretched, allowing more room for both him and the ongoing cum.

She kept moaning in his mouth as he sucked on her nipple, using his other hand to flick the other nipple.

When he felt her cum stop but walls remain flexed and wider, he pressed a kiss to her sternum before ramming her again.

“Tom!” She screamed, her eyes glazing over as she moaned loudly, “fuck, yes, oh my god. Again Tom! Please! Again!”

Gripping her hips to keep her in place so her movements wouldn’t mute any sensations, he removed himself from her.

He sunk his fingers into her core, grinning at her as he removed them and sucked her cum from his fingers, “I need some room”.

She moaned at his teasing and closed her eyes in pleasure as Tom delicately used his fingers to clean her out.

Once he felt confident he got most of it out without causing a significant amount more to release, he licked his fingers clean, moaning before lining himself up.

“That’s it, that’s my girl” he praised as she reached down and pulled his cock into alignment with her entrance in desperation.

Tom held her hips firmly again as he brought his ass backwards and arched up to the ceiling.

She whimpered as she watched his length quickly slide through the air and crash into her, feeling his length fill her as she screamed into his shoulder.

Tom smirked as he felt her cum even more this time, so much so he could feel his cock sliding out of her from the slippery fluids pushing against him.

“So good for me, look at how much you came” he cheered, squeezing her ass as he praisingly gazed at her dripping cunt.

She threw her head back against the wooden desk as she took a shaky breath, a pleased smile on her lips.

Tom kindly stroked her face, brushing the hair off her skin and placing sweet kisses in their place.

He gave her a passionate but gentle kiss to her lips, “y/n my love, you can give me another one, can't you baby? for me, please?"

She took a deep breath and nodded, fingertips dancing over his jaw.

“I’ve got you love, don’t hold back” he said, dropping to his knees before his desk.

“Tom?” She asked faintly, in a bit of a blissful daze from her last orgasm.

He softly tugged her legs towards him, sliding her until her butt on the edge of the desk, “I’ll do the work, you just relax”.

She mumbled an agreement and relaxed her muscles as he rose himself up until his mouth was at her entrance.

“You taste so fucking good love” Tom commented seconds before his tongue licked her outer lips.

“Mmmm Tom “ she whispered, pushing her hips and butt closer to him.

“Settle dear, I’ll take care of you. I promise” he encouraged.

He leaned back into a different angle, using the empty chair area of the the desk to position himself just below her cunt.

Tom took a moment to memorize every detail of this intimate part of her.

Then, he gave her hand a gentle squeeze as a courteous warning before he dove back in.

He swore he came again as he used his tongue to drag the cum out of her sensitive center and swallowed her.

Tom moved his mouth to her clitoris and pressed a soft kiss first, watching as she trembled under his delicate touch.

“Doing okay love?” He checked in, knowing he’d already given her several orgasms tonight.

“Great” she murmured, squeezing his hand that was still holding hers, “your lips feel so good”.

Tom smirked and pressed his mouth back to her clit, this time swirling his tongue around it and watched as she twitched over and over.

He sunk a finger into her vagina, curling it as he instantly found her g spot as if he knew every inch of her already.

Tom removed his tongue and began to suck on her clitoris needily as he tickled her g spot before pushing his knuckle against it.

As y/n screamed, her throat burning from the intensity of the force she was using, Tom moved his mouth to her opening and pulled out his finger.

Tom shouted her name loudly as he lapped up the cum dripping from her onto his mouth below her hips.

“Sorry” Tom panicked, pulling his hand back from her as she flinched.

She laughed faintly and shook her head, “I’m okay Tom, just a bit sensitive”.

He nodded, slowly lowering the wet towel back to her legs.

“I promise, you did good Tom. So good” she assured him, squeezing his arm.

Tom blushed and glanced up at her with a shy smile, “I didn’t go too hard?”

She shook her head, “I would tell you. You know, you don’t need to do the aftercare thing Tom, you’ve done more than enough for me tonight”.

He chuckled, leaning down to place a soft kiss to her forehead, “shh, I’m always going to take care of you and clean up my mess, love. It should only take a few seconds”.

She smiled as she watched him focus on cautiously cleaning their fluids from her body, seeing him double check each location to make sure he didn’t miss any.

“I suppose we don’t need to wait for the standard protocol of the third date to initiate sex now huh?” Y/n teased, her head resting against Tom’s chest as he held her to him as he laid on the couch.

Tom chuckled, kissing her cheek, “I hadn’t planned on it happening this way, but I’m not sure I can hide my physical desires for you after today”.

Y/n rubbed her head against his chest as she got more comfortable under the blanket he had draped over them, “that’s not quite what I asked”.

Tom laughed, tickling her sides, “I won’t tell you sleep with me before our third date, but I’d appreciate it”.

Y/n busted out laughing as she snuggled into his embrace, “god I love you”.

“I love you too y/n, I’m more than pleased we got more personal” he winked, stroking her hair to encourage her to sleep.

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