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The CEO's crush (Tom Holland)


Requested by tomholland098: Y/N is an intern at the company that Tom is the CEO of. He has feelings for her but has a girlfriend, though his girlfriend is always really mean and bitchy towards Y/N. One day, Tom steps in and says something about how his girlfriend treats Y/N before breaking up with her. After the break-up, he goes to Y/N, and finally confesses the feelings that he has for her.


I walked through the office, my heels quietly padding along the carpeted floor as I carried the files in my arms. I gave my coworkers small smiles and 'hi's as I walked to Tom's office. I got to it and raised my fist to gently knock it against the door.

"Come in." His muffled voice sounded. I opened the door, making my boss look up at me as I walked in.

"Oh, hey, darling. I was hoping that it'd be my favourite girl, and I was right." He teased, making me smirk and shake my head as I shut the office door. I had started as an intern at Holland Enterprises six months ago, the start of corporate life being one that very much scared me. Or, had scared me until I had seen who my boss was. I quickly got assigned to be the personal assistant of Mr. Tom Holland, the CEO and therefore head of the entire company. This had kick-started rumours immediately about what I had done, whose dick I had sucked to get that position, as apparently it was unheard of for Tom to give the job of his personal assistant to an intern. Everyone was very shocked to hear that I had gotten the job simply because Tom had taken a liking to me, not that I had done him any sexual favours, but no one thought that it was more than that. In reality, I knew that Tom had feelings for me that ran deeper than a boss employee relationship, even deeper than friendship. Within weeks, I had started to notice the longing glances that I received when I'd been in his office, the gentle smile that no one else seemed to get, even his eyes trying but failing to subtly look at my ass when I'd be in a particularly tight pencil skirt. And the truth was that of course I felt the same about Tom. He treated me well as his employee, but was just an incredibly kind man in general. I couldn't count the number of times where I'd been stressed and so he'd let me off of work a few hours early, or when we'd both stayed well after-hours absorbed in deep and meaningful chat. We loved each other, that was clear. But that was where the problem started. The problem coming in the form of a stick-thin, five-foot-ten blond goddess of a woman called Talia. A bitch of a woman called Talia. Even before I had started to figure out that Tom had feelings for me that were more than friendship, she had had it out for me. I dreaded being in Tom's office at the same time as her because she would always make snarky comments about how I was dressed, how I looked, she would even comment on the supposed shittiness of the work that I was doing for Tom. I tried to not let it get under my skin, but when I was in Tom's office pretty much constantly and she made a comment every time that I was in there, I'd hear how fucking awful I was several times a day, and that was more than enough to affect a person.

"Love? You okay?" I snapped back as Tom spoke. I looked at him, the man chuckling and biting his lip at me as he looked at me from his desk.

"S-sorry, I was daydreaming." I chuckled and shook my head as I walked forwards and put the files on the mahogany surface.

"About me, I hope." He flirted again.

"Stop it." I scolded, making him smirk and chuckle as he leant back in his chair to look at me. That was another thing. Whilst it was clear that Tom and I had feelings for each other, I refused to flirt with him, refused to let him touch me in any non-friendship way, refused to do anything that would cross that line before he broke up with Talia. Tom agreed with my morals, him also not wanting to be a cheater, but it was getting harder by the day, especially given why Tom and Talia had started dating in the first place, a year ago now. Because the truth was that their relationship was more a business deal now than it was a loving relationship. Tom admitted that at the start of their relationship, he did like her, but that quickly fizzled out when he discovered how horrible she was. But of course, it wasn't as simple as that. Talia's father owned the second largest company in London, after Tom's of course, and so their relationship was integral to keeping good relations between the companies. So, whilst Tom and I were under no illusion who he really loved, we weren't going to do anything until he had ended it. I was determined about that.

"So, how's your day been so far?" I asked as I walked around to his side of the desk and leant against it with my legs resting out next to his chair.

"Darling, you can't stand like that, because that makes me really want to put my hand on your thigh." He shook his head and rested his cheek against his forefinger.

"Touch my knee instead, friends can touch knees." I chuckled, making him smirk and nod as he rested his hand on my knee.

"It's been fine. The budgets are in for this month and are under, so that's good as always. Nothing much more to report, apart from that my day got better when you came in." He continued to subtly flirt. I sighed and bit my lip at him. My heart melted every time that he said something like that to me, and he knew that, hence why he did it. But it also hurt. It hurt knowing that right now, I couldn't have the man that I loved, and knowing that Tom was stuck in a relationship with a she-devil that he didn't want to be in. I hoped that the day of Tom ending things would come soon, but that was what I'd been thinking for the last few months, and so now, I had no idea when it would be. I knew that that wasn't Tom's fault, though.

"Tommy, you can't say stuff like that to me-."

"Why not, though, sweetheart? We all know that Talia and I don't love each other, it's not as if it's a real relationship." He scoffed and shook his head as he wheeled his chair to me so that his body was by my legs as he put one arm over my legs.

"It's still a relationship, one that you're very much in. Look, I know that you two and I know that your relationship is transactional now and doesn't include love, but I'm still not going to let you cheat on her with me. If you want to have me, that's okay, but you need to end it with her first." I nodded.

"I know, love, and I respect you for not letting me cheat, I just...it's hard, you know that. There are so many moving parts, it's not as simple as me breaking up with her. But you know that the second that I can, I will." He reassured.

"I know, Tommy. And you know that I'll wait for you." I returned.

"Thank you, love." He nodded before leaning down and kissing my leg.

"Oy, no, kissing a leg is not a friend thing." I chuckled, making him groan teasingly as I stood up and headed back around his desk.

"I thought that I'd get away with that one. Come by at the end of the day for a drink, darling?" He suggested as I headed back to the door. I looked at him and bit my lip.

"Sure, Tommy. A friend's drink." I emphasised.

"As much as I don't want it to be." He smiled, making me return it and bite my lip as I opened the door and slipped out of his office.


"I'm being serious, you know how messy Harry can be, so we're sitting in this really expensive and classy restaurant, and he's got to spend the rest of lunch in this wine-soaked shirt because he spilled two-hundred-pound wine that my dad bought, all down himself!" Tom exclaimed, my body almost falling off of the desk as I laughed my ass off.

"I can totally see Harry doing that too!" I laughed and shook my head.

"Exactly!" Tom exclaimed again, only making me laugh more as Tom and I drank whiskey together in his office and talked about the somewhat disastrous lunch that Tom's dad had taken him out to today. This was something else that was commonplace with us. Tom loved to unwind from a stressful day with me and a single-malt whiskey, even if he couldn't have me in the way that he wanted me. He referred to it as the last hour of peace and love that he'd get before going home to Talia, something that I was honoured to be a part of, but also still broken-hearted by because of the situation.

"What about your day, love? What did you get up to, apart from looking really good in that outfit whilst you got me files?" he smiled, making me playfully roll my eyes at him as he raised his drink to his lips.

"Nothing exciting. Just my normal duties of bringing the boss his paperwork. The boss who won't stop flirting with me. Really, I should file a sexual harassment case, because it's just ridiculous now." I teased, making him laugh as he moved the tumbler back down from his lips.

"It would be sexual harassment, if you didn't like it, love." He returned the teasing with a nod as he stood from his chair and put the tumbler down before looking at me. I bit my lip and returned the glance, Tom's eyes flicking between my lips and my mouth as he moved closer to me. My heart was thumping harshly in my chest, my mind wanting nothing more than for him to lean in and finally kiss me. We couldn't, though, and that was what hurt me daily. Tom didn't seem to care, his hands raising to gently hold my arms before they moved down to my waist as he moved closer to me. I gulped harshly, my mind telling me that this was wrong, but my heart wanting to let it happen as he was now right in front of me. He looked down, his head starting to dip to close the gap between our lips.

"Tommy...we can't, this isn't good." I whispered and shook my head, though I made no effort to move away as his lips got closer to mine.

"No, sweetheart. What isn't good is me staying in a fucking broken relationship for the sake of my business, when I work with the girl that I love daily. And I'm sick of it." He mumbled, making me gulp as he continued to lean down. Suddenly, the door flew open behind us, Tom's eyes widening as he quickly stood back up.

"Tom, I-WHAT THE FUCK?!" I gulped and let my eyes flutter shut, my heart leaping in my chest as Talia's screeching voice rang out.

"Talia, what the fuck are you doing here?" Tom scoffed as I quickly stood from the desk and smoothed out my skirt as I desperately tried to ignore my harshly blushing cheeks at the fact that Talia had caught Tom about to kiss me.

"I thought that you'd fancy a drink before we headed home, but I can see that you already had one with the office slut." Talia spat, making me gulp harshly and try not to cry as I kept my eyes to the floor.

"Woah, hey, there's absolutely no need for that." Tom scoffed.

"Of course there is, Tom, do you think that I don't know what you two have been up to since she came here? Fucking sneaking about behind my back like the little whore that she is?" She snapped.

"How fucking DARE YOU speak about her like that! She's done more for me in the last half a year than you've done in our entire relationship, so I will NOT have her shown such disrespect!" Tom yelled.

"Mr. Holland, I-I think that I'm just going to go." I gulped, my eyes still on the floor as tears started to leave them.

"Y/N, no, don't leave until you get an apology from Talia." He nodded.

"Are you fucking delusional, Tom?! I'm not apologising to your fucking bitch of a side piece-."

"I'm sorry." I choked and shook my head, the whole situation becoming too much as I rushed out of Tom's office.

"Darling, please!" I heard Tom call after me, but I ignored him as I quickly grabbed my bag and coat from my desk before starting to rush towards the lift.


Tom's P.O.V

"It would be sexual harassment, if you didn't like it, love." Tom returned Y/N's teasing with a nod as he stood from his chair and put the tumbler of whiskey down before looking at Y/N. She bit her lip and returned the glance, Tom's eyes flicking between her lips and her mouth as he moved closer to her. He knew that what he was about to do would breach the friendship status that they'd been trying not to cross out of, but he couldn't help it. Y/N just looked so fucking perfect perched against his desk, just like she had every single day since she'd started work as an intern, and then as his personal assistant. Tom was falling more for the girl by the day, and it hurt that he couldn't kiss her, couldn't touch her, not until he broke up with Talia. But that was coming soon, especially if his bitch of a girlfriend continued to speak to Y/N the way that she did. But that wasn't what he was thinking about right now. He was thinking about how much he wanted to kiss Y/N, how much he wanted to take her right against the desk. Even if he couldn't, yet. Tom didn't particularly care anymore about the idea of betraying Talia though as his hands raised to gently hold her arms before they moved down to her waist as he moved closer to her. Y/N gulped harshly, her eyes flicking up to him as he was now right in front of her. He looked down, his head starting to dip to close the gap between their lips.

"Tommy...we can't, this isn't good." She whispered and shook her head, though she made no effort to move away as his lips got closer to hers. Tom had always respected Y/N for the fact that she didn't want to do anything with him whilst he was still with Talia, but ultimately both of them were giving in, especially as it was clear that he wasn't with her for love. He wanted a relationship that was filled with nothing but love, and he knew that he'd get that with Y/N. Even if it had to overlap slightly with his relationship with Talia.

"No, sweetheart. What isn't good is me staying in a fucking broken relationship for the sake of my business, when I work with the girl that I love daily. And I'm sick of it." He mumbled, making her gulp as he continued to lean down. Suddenly, the door flew open behind us, Tom's eyes widening as he quickly stood back up. He gulped harshly, his heart leaping as Talia stood at the now open door.

"Tom, I-WHAT THE FUCK?!" She screeched.

"Talia, what the fuck are you doing here?" Tom scoffed as Y/N quickly stood from the desk and smoothed out her skirt before the pair of them moved away from each other.

"I thought that you'd fancy a drink before we headed home, but I can see that you already had one with the office slut." Talia spat, making Y/N gulp harshly as she kept her eyes to the floor.

"Woah, hey, there's absolutely no need for that." Tom scoffed.

"Of course there is, Tom, do you think that I don't know what you two have been up to since she came here? Fucking sneaking about behind my back like the little whore that she is?" She snapped. Tom's eyes widened, anger starting to bubble up inside of him at how Talia was speaking about Y/N.

"How fucking DARE YOU speak about her like that! She's done more for me in the last half a year than you've done in our entire relationship, so I will NOT have her shown such disrespect!" Tom yelled.

"Mr. Holland, I-I think that I'm just going to go." Y/N gulped, her eyes still on the floor as she refused to look up at either of them.

"Y/N, no, don't leave until you get an apology from Talia." He nodded.

"Are you fucking delusional, Tom?! I'm not apologising to your fucking bitch of a side piece-."

"I'm sorry." Y/N choked and shook her head, Tom's eyes widening and his heart breaking as the love of his life rushed out of his office.

"Darling, please!" He called after her, but she ignored him as she grabbed her bag and coat before starting to rush towards the lift. Tom scoffed and shook his head, nothing but anger in his heart for Talia as he ran a hand through his hair.

"What the fuck?! Was all of that name calling really necessary?!" He snapped as he looked at her.

"Of course it is! She's fucking my boyfriend, of course I'm going to call her names-."

"The funny thing is, Talia, is that we've done fuck all. We've not even touched in a sexual way out of respect for you, meanwhile, you've actually been fucking your side piece. So, don't come at me and her, slut-shaming her and yelling at me when we haven't done anything more than be friends, whilst you've actively been cheating on me." He nodded. Her eyes widened slightly, a scoff leaving her lips at his words.

"How did you find out?" She shrugged nonchalantly, as if Tom hadn't just caught her actually cheating on him.

"It was pretty fucking obvious when the third payment to a hotel went out of my account, and the timing coincided perfectly with when I was home for the night, just like it had done the first two times. You could have at least tried to hide it out of respect, I haven't touched Y/N in a sexual way out of respect for you, and you couldn't even show me the same courtesy." he spat.

"Whatever, Tom. You caught me, boo fucking hoo." She scoffed and shook her head. Tom clenched his jaw and looked at her. In that moment, he felt nothing but seething anger for the woman, when all that he'd felt five minutes ago in Y/N's presence was love and adoration. He knew what he had to do. And he had to do it now.

"I can't do this anymore, Talia. I can't do the pretending, the transactional relationship, the not being able to touch the woman that I actually love out of respect for you. I'm done." He stated. Her eyes widened.

"Tom, we can't just break up, you know better than anyone that our companies need this-."

"I don't care anymore. I'm sick of putting the business in front of my own happiness and love. I'm sick of not being able to kiss Y/N, hold her, treat her as my girlfriend instead of my friend because of our relationship, especially because you didn't even offer that same respect. I'm done, Talia. Tell your dad, tell the boards, tell whoever the fuck you need to, but I don't care anymore. I'm done." He shook his head, the girl staring at him with wide eyes as he grabbed his jacket before running out of the office.

"Tom, you can't just leave! Fucking come back!" She yelled after him, but he didn't care. If he was quick enough, he could catch Y/N before she went home. And so that was what he was planning to do.


Y/N's P.O.V

I walked along the dark street, the relentless rain having already soaked me through as I walked to my car. I shivered uncontrollably, tears running down my face and mixing with the drops of water falling from the sky as I walked away from Tom's office. It broke my heart to walk away from him, especially after the amazing moment in which we'd nearly kissed, but I couldn't handle standing there and letting Talia verbally abuse me like that. Though I had appreciated Tom standing up for me like that, I had just had enough. I was going to go home and cry myself to sleep after downing a bottle of wine, given that I couldn't spend the night with Tom like I wanted to.

"Y/N!" I stopped in my tracks, my eyes widening slightly as Tom's voice rang out. I looked over my shoulder, my eyes wavering and my heart leaping in my chest as surely enough, the boy was jogging to me, his hand above his head in a futile attempt to protect his hair from the rain.

"D-did you follow me?" I scoffed as I turned to face him fully.

"Well, it sounds creepy when you say it like that." He teased, making me chuckle and bite my lip as he walked towards me. He gulped and looked down at me, water now dripping off of the end of his curls as we stood in the rain.

"I just broke up with Talia." He admitted. My eyes widened.

"W-what? But your companies-."

"I don't care anymore, love. I don't know what it was, but hearing her insult you like that, hearing her be so fucking horrible was the final straw for me. I'm in love with you, darling. I'm so fucking deeply in love with you, and I'm done not acting on that. To be honest, it was stupid for me to stay with her for my business in the first place, because what the fuck is the point in being successful if I'm not happy and with the person who I love? That's you." He nodded. I bit my lip, my heart racing and tears leaving my eyes at his words. Because this was it. This was the moment that I'd been waiting six months for, and it was finally here. And fuck was it worth the wait.

"I love you, Y/N. I love you." He nodded before taking my face and leaning down. He pressed our lips together, me returning it immediately as my eyes fluttered shut. I raised my hands to hold his wet cheeks, his hands moving down to hold my waist as we kissed in the rain. Fireworks were going off in my head, every fibre of my being working overtime to make me realise that yes, this was actually happening. Tom had finally ended it with Talia, and he was finally kissing me. In the rain, too. It couldn't get much more romantic than this. I broke the kiss and touched our foreheads, my eyes fluttering open to see that Tom was already looking at me.

"I love you too, Tommy. Fuck, I love you too." I choked and shook my head. He smiled and bit his lip, making me return it as we just held each other.

"Come on, let's get to my car and get somewhere dry. Because now that you're my girlfriend, we're going to be doing a lot more than just kissing." He nodded, making me laugh as he leant down and pressed our lips together again. I returned it, my arms curling around his shoulders and pulling him closer as we made out in the rain. He broke the kiss and took my hand, laughs leaving our lips as we ran to his car, even though both of us were now soaked through anyway. I didn't care, though. All I cared about was the fact that I was now officially Tom's. I was now officially Tom's girlfriend, and that made me the happiest girl in the world. 

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