warnings:SMUT, swearing, sir kink, rough sex, slight degradation kink, oral sex (female receiving) & slight choking
summary: y/n really does love Tom, and he really does love her but y/n refuses to make their relationship official. This is a good plan for y/n’s somehow flawless reputation and for better secrecy for the both of them, though this does mean the boundaries for the other female coworkers are long gone. So y/n has to show them better yet scream it for them.
a/n: the odd thing is, with all these kink warnings i’ve written a lot dirtier
y/n sat at her neatly organized desk. The cold metal flushed up against her warm skin as she typed away at her computer. She looked over to across from her, imagining Tom sitting there doing absolutely nothing but still managing to look like a god. At times she wants to kick herself for falling for him. In all truth, she wanted to stay completely professional and more importantly so wanted to steer clear of the cliche. Unfortunately, she had slipped into the status quo of the personal assistant falling head over heels for her boss.
It was so childish when she realized it, like something out of a romance novel. When she caught wind of her feelings y/n prayed that Tom feels the exact same painful way that she did. If he didn’t want a relationship with her, then she would have to get over her stupid emotions and move on with her life. But of course, Tom had fallen almost identically.
He also didn’t want to express how he felt because it felt widely inappropriate for him to be seeing an employee, let alone his own personal assistant. Those few short months were agony for the both of them, wondering if the other wanted them or not. Passing each other in the hallways with just the feeling of each other next to their bodies, the lingering lustful looks that would never seem to end and the obvious but mindless flirting that would get on everyone’s nerves. At that point, they were desperate for an answer or anything for that matter. Luckily it didn’t take long for them to strip each other and use the late night as a secret rendezvous to enjoy the others’ bodies.
From that moment onwards, They decided to see where a romance could go with them. So now, three years along and an engagement, they were still going strong and she still feels the exact same way she did when she first met him.
“Hey, do you know if Mr Holland is in,” a high pitched female voice caught y/n in her daydreaming. y/n peered up at her, she was the last person she wanted to see. Cheryl stood in front of y/n’s desk, her red claw-like nails tapping away at the shining wood causing y/n to feel the incoming headache she always gets whenever Cheryl is around.
“Yeah, he’s just on a call but I can take a message,” y/n almost spat, Tom wasn’t on a call but there was no way in hell y/n was going to leave Tom alone with her. Cheryl’s face turned into a hard scowl once y/n refused to let her in. Her arms folded underneath her obviously enlarged breasts causing y/n to get worried that they would burst.
“I actually have the weekly reports from the L.A branch, I’m sure Mr Holland can see me,” Cheryl let her frown turn into a smirk as she held up the portfolio filled with neatly stacked papers. y/n knew the right thing to do was to allow the she-devil to see her secret fiancee but her emotions had another plan.
“It’s actually quite important, he’s making sure the investors from Dubai close in on their deal,” y/n lied through her teeth. Of course, they closed off the deal but Tom hadn’t discussed it with anyone other than herself and his family. “If you leave it here, I can give it to him when he gets off, courtesy of you of course.”
Cheryl’s deep green eyes shot daggers at y/n as she slammed the folder on y/n’s desk and stomped off. y/n gave herself a silent pat on the back. Thank god she dodged that temptress of a bullet and better yet she had a reason to go see him.
Though she knew Tom would never cheat on her, they did have a deal. Both of them knew if they announced their relationship to the company then y/n would take major heat for it, people would talk about y/n behind her back saying that she got to where she is because she’s sleeping with Tom. Though she was seeing him, y/n made it clear that she would stay independent and not have to rely on him and his money. So they both decided that they would continue acting as they did before they got together, which means Tom has to act as if he is single.
y/n got up from her large desk and walked over to his office, her plum heels clicking against the marble tiles. Before she knocked, y/n made sure she had herself under control and waltz in. Tom’s face lit up when he saw her approach him.
“What can I do for you angel face?” Tom asked sweetly as he sat up straight in his faux leather armchair.
“Cheryl wanted me to give the L.A reports to you,” y/n kept to her words as she slid the papers across to him, Tom caught it and started to flick trough.
“Weird, Cheryl would usually give these to me herself,” Tom sighed, he knew exactly why Cheryl wasn’t standing in his office trying to seduce him like she always is but he found it quite amusing to see y/n let out the green-eyed monster and he wanted to toy with it and see what it would get him.
“Well, she left them with me,” was all y/n could get out, she knew she shouldn’t be mad at Tom but she couldn’t help it. y/n felt like she was sharing him with a woman who doesn’t want him for anything except his money and impressively large dick.
“Sweetness, did you tell her or did she leave them?” he pondered, Tom knew the answer but he wanted to see if he could get her to crack.
“She left them,” y/n responded curtly never breaking eye contact with him. y/n knew what he was doing and she wasn’t going to let him play with her. y/n watched Tom slowly get up from his seat and stride over, y/n felt her face heat up too quickly for her liking as he got closer. She didn’t falter though, making sure to keep her head high.
Tom’s hand snaked itself around her almost cinched the waist, while the other went from the engagement ring that was hidden between the curves of her breast. He sighed softly when his digits played with the warm diamond-encrusted ring, he really did love her and Tom wanted to tell everyone about it, but he respected her wishes to keep it a secret until after the wedding.
Still, though, he couldn’t help but tease her. Tom obviously knew y/n was jealous, she had been for weeks but Tom hadn’t picked up on it since a few weeks ago when y/n nearly blew his head up with her death glares as he innocently chatted away with ever-present Cheryl. Tom looked up at her, making sure not to lose himself in those eyes.
“Are you jealous darling?” Tom asked huskily, y/n felt almost offended by how he spoke. How dare he speak that sexy to her, it felt like she had to cave in but y/n’s pride was a bit bigger than her lust at this moment. y/n’s own hands cupped his cheeks and brought him closer to her.
“No,” she replied. Tom didn’t respond but instead, he let one eyebrow lift up and allow a sly smirk to fill his lips. y/n stared up at Tom before she placed a soft chaste kiss on his lips. “I’ll see you at home.” y/n told him sweetly as she pulled away from Tom and walked out.
Tom wondered how long and how drastic his game could go before she caved. He felt sort of guilty for toying with her but Tom couldn’t deny that seeing her jealous and in a way territorial was so fucking hot, he needed an excuse to bend her over his marble desk and pound her into next week and just the thought of y/n being envious was enough for him to feel a stirring within himself.
Tom knew exactly how to push her buttons. He knew exactly how to get her in the palm of his hand in a matter of moments. Before Tom met y/n, he definitely would consider himself a playboy or for a better term; a fuckboy. Though he hated talking about it now and he has changed, Tom still knew how to work with a woman especially with her yearning.
Tom couldn’t wait for tomorrow.
━━★✼☆｡
Tom stood in the elevator with y/n standing idly beside him, their normal morning routine felt off as the tension from yesterday had carried over to today. Tom let the smirk he had been hiding all night slip onto his face, y/n took notice and slight offence.
“What are you smirking at mister?” y/n asked playfully as he attention was stuck on the clear metal of the elevator doors.
“That you are jealous,” Tom replied, he didn’t need to look at her to know the face she was giving him currently. y/n had her arms crossed under her bust and her slightly plucked eyebrows were furrowed in a mixture of annoyance and anger. It’s the look she gives him when she hears that he’s done something stupid and Tom really is.
“For the last time Tom, jealousy is an ugly emotion and I don’t feel it,” y/n told him sternly. y/n was determined to get this into him, even if it was total bullshit.
Tom felt a wave of playful hurt wash over him so he retorted with, “you’ll have no problem with me possibly flirting back with Cheryl.” Tom knows he shouldn’t do this but his curiosity is off the rails now.
y/n stared up at him trying to keep her face expressionless with his mind screaming at him to not even look at that red-headed witch. “No problem at all Tommy, just make sure your eyes come back to me.”
The tension was sliced by the doors swinging open and both of them walked out, making sure to keep their heads held high. y/n watched as Tom walked into his office and quickly made work on mentally scolding herself. How could she be so stupid? She obviously let her stupid ego shut off the part of her brain that makes all the rational and adult decisions. It was too late now to tell him the truth, it would end up sour and that is the last thing y/n wants. Or maybe coming in a close second to the sight of Cheryl with a cheeky smile and her blouse unbuttoned so low that y/n could basically see her nude bra.
It was routine for her at that point. Have a snarky but pointless snap at Cheryl before allowing her to see Tom for 5 minutes before interrupting to make sure her hands stayed where y/n could see them. But now that she had basically given the all clear for Tom to reciprocate the banter with Cheryl, it was her worst nightmare.
“Looking tired today y/n,” Cheryl told her somewhat sweetly as she taped her heel infront of the sleek wooden desk. y/n stared up at Cheryl, her face completely blank with her brain screamed with a mixture of anger and panic.
“Yes, quite tired of your pointless bullshit Cheryl,” y/n retorted curtly, not in the mood for their game of verbal ping pong but instead just want to skip to the part where y/n confidently dismisses her.
“I need to speak with Mr Holland,” Cheryl told her bluntly. y/n thinks that by now, Cheryl should have a new way of manipulating y/n into letting her secretly flirt with her fiancee but no, same old trick.
“I give you this answer every morning Cheryl, he’s not ready to start meet-”
“Ah, Cheryl,” Tom’s smooth voice made y/n grip at the corner of her desk, “we need to discuss the L.A branch’s numbers, why didn’t you get in here sooner, pet?” The name rolled off his tongue, y/n now loathed that word.
y/n eyes frantically went from Tom who was cockily leaning against the pure wood of his office to Cheryl, who was basically undressing him with her needy gaze. y/n wanted to protest but her voice was caught in her throat. So, with wide eyes, she watched as Cheryl gave her a wicked smirk before she skipped off down the hall to meet Tom. He gave y/n a dark smile before allowing Cheryl to walk in.
y/n sat dumbfounded and furious. She was now only realising how painful this day was really going to be. How could she be so stupid as to let her pride allow Cheryl to continuously flirt with her fiancée and allow Tom to do it right back? She wasn’t going to break through, there was no way in hell she was going to admit that she was jealous. Little did she know; this was only the beginning of Tom’s dirty game.
She was so in her feelings and mindless thoughts that y/n didn’t even realise that it had been 15 minutes since Tom and Cheryl started ‘talking’ shall she put it. The only she was pulled out of her angry daydream by the soft chime of a text message. Quickly she fished it out her bag and stared down at the bright screen.
I never really noticed how aggressive her flirting can be. The text taunted her in a way like Tom was dangling it in front of her face. Of course, he was going to start texting her in the middle of his so-called meeting, he wanted her to know that he was in that room with Cheryl all by themselves.
I notice it every fucking day. She responded quickly, desperately want Tom’s attention to stay away from Cheryl. Meanwhile, Tom sat in his massive chair as he droned out from Cheryl’s rambling. He immediately regretted letting Cheryl get him alone, but he was determined to follow through with his plan.
Really, I must be blind. He typed away remembering to peer up at Cheryl to make sure it looked like he was listening to her.
Well, it sounds like your little meeting is boring you, Tommy. y/n sent the text with the intent to draw him away from her, and by that, she means to get him so worked up all he’ll be able to think about it here. Tom knew what she was trying to do, he wasn’t a complete fool, but he wasn’t opposed to saying no especially when he knew the outcome.
You have no idea princess. y/n got a rush from all of this, she felt good about stealing Tom away from Cheryl. Tom didn’t need to guess what he needed to say and it seemed like she didn’t either because Tom could somehow already feel himself stiffen slightly.
Maybe I could give you some excitement? If y/n was in the room with him right now, Tom knew exactly how she would have said that, her lust blown pupils would stare up at him through those impressively long lashes of hers and she would let her nails rack ever so slightly over the curve of his enclosed dick. Tom let the vision wash over him with pure bliss.
I wouldn’t be opposed. Tom sent back, y/n stared down at her phone with a wide gleam. y/n quickly looked around the massive waiting room and snapped the picture. Tom didn’t expect to get that kind of response from her so fast, either way, Tom choked on the very air he was breathing when he opened a picture of y/n with her already tight nave blouse undone past her lacy bra and her fingers dancing on the skin right above her nipple, simple yet so explicit. Excited yet?
Extremely but I’m not done yet. It took a while for Tom regain his composure and he wanted to test her emotions to the very edge, so sadly he had to decline the wonderful offer. y/n read the text and slammed her hands down in frustration. She doesn’t know how much longer she going to last.
━━★✼☆｡
y/n had been standing at the coffee machine for 10 minutes now. She doesn’t understand why Tom doesn’t just install another one. Hopefully, he can spare 30 bucks in his endless amount of money. Still, she got her coffee and walked off in a hurry to drink this bad boy.
As she walked down the seemingly never-ending hallway, y/n let her mind wander for a bit. Maybe she should just give in. Sure she didn’t want to give him that gratuitous satisfaction but y/n had no clue to what extent Tom’s plan was going to go for and how extreme it was going to become.
Maybe they should make their relationship public. For god’s sake, the wedding was only a few months away and they were still sneaking around like dumb teenagers. She knew just how badly Tom wanted to announce to basically the whole company that they were getting married but y/n doesn’t feel so comfortable yet. Still, a healthy relationship is founded on trust and compromises, y/n knew that she couldn’t keep denying him that urge. y/n mindlessly giggled at her, of course she would use those word to describe him.
Just upstairs, Tom sat at his computer typing away as he thought of what he should do next. He was having too much fun with this, he was having too much fun making y/n writhe with anger and need. Still, he didn’t take into account that maybe his plan worked in another way or in better words another person.
Tom felt his phone go off, he flipped it over and checked the screen. It was one of the new investors from New York, they weren’t extremely important so he could excuse himself from taking the call but if he did, Tom would have to call them back.
So to create a legitimate excuse, Tom stood and basically rushed out the door and started pacing slightly in the hallway.
“Mr Holland, are you okay?” Cheryl’s voice asked him from afar. Tom swivelled around to meet her eyes. Tom took notice that there were exactly three buttons undone, not too much to look obviously sexy but not too little to not tell him anything.
“Yes I’m fine Cheryl,” Was as far Tom wanted the conversation to go, but of course Cheryl didn’t notice and crept forward.
“Are you sure? You looked a bit frazzled,” Cheryl asked again, this time with a sultry tone in her voice. Tom didn’t like where this going, sure he could play it off as just part of the game but he wasn’t really in quite the mood to fake flirt with her and y/n was nowhere to be to seen.
“Really, well I must go fix myself up then,” Tom laughed awkwardly as he attempted to flee but Cheryl’s cold hand clamped around his wrist, thank god he was wearing some sort of protection for those icy fingers.
“I could help you fix up if you don’t mind,” Cheryl winked subtlely, Tom froze for a second before he quickly undid the tight grip.
“Cheryl what you’re insinuating is extremely inappropriate,” for a moment, Cheryl looked like she was not only taken aback but also slightly embarrassed by Tom’s rejection. But of course dove right in again.
“Mr Holland, don’t be shy you can touch them if you like,” Tom was confused for a moment before he stared down at her not blatantly on display breast. He was going to retort when both Tom and Cheryl heard a soft cough just close by. Turning around to see y/n was like a miracle for Tom, he let a little smile appear while Cheryl wasn’t looking.
“Cheryl, I’m sure no one wants to touch those balloons,” y/n retorted, her face contorted with only annoyance. Tom wondered why she was red with fury yet.
“Get lost, y/n,” Cheryl seethed, “this is none of your business.”
“It may not be, but I do need to speak with Mr Holland about our most current investor,” she looked at Tom with wide eyes and he immediately pulled away from Cheryl. y/n’s coffee was long gone by now, she fought the urge to almost pull him inside his office. But she waited patiently and watched Tom duck around her and y/n happily followed him. She gave Cheryl one last look before she closed the doors behind her and locked it.
“Well did you enjoy yourself?” y/n suddenly darkened. Her heels harshly meeting with the tiled floor until she was nose to nose with Tom. He only stared down at her in glee, he had her right where he wanted her.
Tom simply walked away, his expression completely unfazed. “Possibly.”
y/n stared at him in disbelief, he was really taking it this far! “Well, you’re going to enjoy making me scream a whole lot more.”
Tom was taken aback by her sudden outburst, Tom could feel his arousal heating up with every second she was near him. “Oh I’m sure I’ll love to hear your pretty little moans and you’ll adore getting pounded into next Friday,” with every word that escaped from his lips, Tom moved closer until he was face to face with her again. “But you just have to admit it doll.”
y/n coward beneath him, the mere thoughts alone were almost blinding her with lust. One of Tom’s hand pressed gently on her warm cheek while the other slowly traced the skin around her panties. His long fingers dipping in every so often making y/n’s legs almost buckle at the long-awaited sensation, “you are so wet for me, you really want this,” Tom chuckled darkly, peppering soft kisses at the nape of y/n neck. She couldn’t respond, her voice caught in her throat and her lips only releasing short and simple whimpers. “Use your big girl voice,” he told her softly. His touch was starting physically weaken her so she gave in.
“I’m jealous,” she admitted quietly, Tom could just hear it but he wasn’t totally satisfied with her answer.
Tom let his hand drift slightly down to her lips where he pulled her bottom lip down with his thumb and his own lips hover so close to hers that she felt static, “of what?” he demanded. y/n looked up at him with desperation in her eyes, Tom wasn’t backing down.
“I’m jealous that other women look at you like they need you,” y/n told him again, this time louder and more firm. Tom stared down at her with a wide smirk on his face. Without a word of warning, Tom picked y/n up and rushed to harshly slam her against the wooden wall. y/n hissed at the rush of pain that shot through her back but she was immediately distracted by Tom’s hot and soft lips upon her giving y/n quick and heated kisses.
“That’s all you had to say baby girl,” Tom spoke happily as he stabilized y/n against the wall and physically tore her blouse right down the middle causing y/n to squeal loudly. "How about I take you up on the offer to make you scream,“ he told her slowly as his hands fondled at her enclosed breasts. y/n didn’t respond verbally but she did nod her head so fast she thought it was going to fall off.
Tom mouth started littering her decolletage with small bruises and marks, slowly getting closer to the valley of her breasts. Finally, his nose was deep in her cleavage and his fingers were flicking and pinching at her clothed hard nipples while her’s were tugging softly at the tuffs of brown locks. "Oh god, yes sir,” y/n slipped out in a moment of blinded passion. Tom stopped all of his movements and got face level with her once more.
“You want to play that game,” Tom spoke darkly as his easily made work of her lace bra, y/n gave him a wide smile, “you’re not going to say anything unless it’s that name coming out of the pink lips,” Tom ordered as he started to get on his knees still keeping y/n in place against the wall.
Her legs were draped over his shoulders and Tom’s hands stabilized her by her ass. Tom’s face was now inches away from that delicious cunt he calls paradise, hell he could even smell the divine nectar. He quickly tore her matching pantie down her legs and threw them across the room. “Use that dirty mouth to let everyone know,” With that, he dove in.
Tom’s tongue latched itself on her already throbbing clit, sucking every so often. His fingers would spread her wet lips before diving into her at a slow and gradual pace curling once he found the right spot inside her. y/n above was barely able to keep her eyes open, every little thing he did to her made y/n squirm and moan more and more. Tom decided to remove his tongue from her sensitive nub and start tongue fucking her fast and his fingers now took over by circling figure eight above.
“H-Holy shit,” y/n moaned atop him, she felt her orgasm approaching. She had never cum this fast, she was slightly embarrassed. So she tried to keep it a bay for a long as she could but unfortunately for her, Tom knew when she was holding back from him. Tom released himself from her little haven to stare up at her with dark eyes. y/n saw the shining juices dripping from his nose down to the small stubble on his chin. “How dare you hold back for me,” y/n had never heard him so work up, it was getting even harder to hold herself back. “You’re a jealous slut and you’re not coming, you’re a pain in the ass,” he growled lowly as he gave her bare ass cheek a hard slap, his fingers never stopping the relentless assault on her pussy.
Tom stood up slightly causing his fingers to slid into a deeper part of her that even y/n didn’t even know existed and started to dig themselves harder into her. Within almost a second y/n’s orgasm was ramming into her, she swears she saw only black as she came around Tom’s fingers, a string of praises and screams tumbled out of her mouth.
When she opened her eyes, she saw Tom almost tearing his clothes off him. His suit came off first then his show and finally his boxers slid down to reveal his painful erection that had been stirring since this morning when she sent that photo. y/n leaned forward to stroke it but Tom’s hands clamped down on her wrist. “Get on my desk with your legs open,” Tom snapped at her, his expression completely blank. y/n doesn’t know if she’s afraid of excited about what’s to come.
y/n paced over, the desk was a little taller than she would have liked so she had to jump up giving Tom a gorgeous view of her bare ass. She sat down, the cool metal piercing her flushed skin. Tom let out a slight giggle before he waltzed over and basically swiped half of the utensils on his desk to crash on the floor. y/n stared up at Tom in disbelief, she was about to give him a scolding but was cut off by a hard push from Tom to have her back flat against the surface.
“Be a good little slut for sir and keep your arms above your fucking head,” Tom whispered before he stood straight. For a moment, Tom stared down at her in awe. He was about to fuck the life out of a girl most guys would die for, his eyes caught her engagement ring in the light. He paid 40 grand for that thing.
Without warning, Tom slammed into y/n. Her back arched and a loud almost pornographic moan tumbled from her mouth. Tom gripped tightly at her hips, suppressing the instinctual groan that came with feeling y/n clenched around him. Tom didn’t hesitate to start slow instead, he immediately began to pound himself into her. The only sound was the hard slapping a raw sweating skin, their combined moans and of course the constant noise of the office just outside.
Sure they had fucked in the office before but never when there was a whole fleet of people just outside, It aroused both of them. Tom brought y/n down ever so slightly to meet his slams, making y/n writhe and squirm as she tried to keep her arms above her head.
“C-can I plea-fuck, please touch you s-sir,” y/n just barely managed to get out through estranged moans and hard slamming. Tom smiled down at her, for a second y/n thought he would give in to her request.
“No, but I can touch you all I like,” he laughed menacingly. As he continued to pound y/n into oblivion, he leaned forward and stared litter bruised across her hot flesh before his finger danced up to her neck. He had always thought about it and now was the time to test it. “If I squeeze to hard tell me straight away.”
“O-okay,” y/n replied shakily. She felt one of Tom’s hands grip softly around her neck. He was fucking choking her. God this is the hottest thing he’s done. Tom lent forward to have his toned body now heave on top of hers as he felt their combined orgasms approaching. y/n was in utter heaven, the feeling of Tom’s massive dick filling every inch of her up, his muscular body squished up against hers and his long finger daintily wrapped around her neck.
“Sir, I-i’m going to cum,” y/n warned him, she was now rolled her hips onto him. Tom let his other hand start tracing soft circles on her clit.
“I know, so am I,” Tom replied as he picked up the pace, y/n didn’t even believe that was humanly possible.
Together they reached climax, y/n felt her second orgasm way more intensely than her first. She trembled and screamed underneath him, breaking his rule by clutching onto his broad should for support. Tom couldn’t care that she disobeyed him, because he was too busy seeing stars as he let his hot seed fill her up.
Tom pulled out and witness their combined liquids trickle out of her. He scooped some up with his finger and brought it to her mouth, which she promptly swallowed. He was the luckiest guy on earth.
Slowly they started to get redressed. y/n picked the spare clothes she always leaves his in his office and Tom just decided to wear his half-tattered in honour of his accomplishment. Tom went to stare over at her when he saw y/n slip the ring off her secret necklace and onto her finger.
Tom rushed over and looked at her with wide eyes, “are you sure, you want to go public?” he asked softly.
“Babe, you just fucked me senseless while the entire office is still working right outside,” she giggled sweetly, making Tom’s heart swell. “If I didn’t want to go public, we wouldn’t have just done that.”
Tom pressed a soft chaste kiss to her lips to which she happily responded, “I love you,” was all he said.
“I love you too,” y/n told him. “But now, I want to enjoy my victory,” she fluffed his already sweaty hair and skipped out of his office.
Summary: heavily influenced by the movie “the proposal”
Faced with deportation to his native United Kingdom, the playboy CEO Holland’s Tech Point located in the Big Apple, Tom Holland, tells the world that he’s engaged to marry Y/N Y/L/N, his hapless assistant. Y//N reluctantly agrees but has a few propositions of her own, including flying across the country for him to meet her eccentric family.
With a immigration agent hot on their trials and watching their every move, Tom and Y/N must stick to their plan despite numerous bumps in the road.
pairing: ceo!tomholland x secretary!reader
warnings: will be posted with each chapter, almost like a crack fic, tom is a bit of an asshole sometimes, SMUT, steamy, super sweet
