I Fucked My Boss’ Daughter - Cover

I Fucked My Boss’ Daughter

Copyright© 2026 by Highlander90

Chapter 2

Fiction Sex Story: Chapter 2 - This is a story about a guy who accidentally fuck’s his boss’ daughter. He then keeps fucking her.

Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   Cream Pie   Oral Sex   Big Breasts  

I was awoken some point later that day from an afternoon nap by the repeated sound of text notifications and then a phone call. They were all from my sister.

“Hello...” I said with a groggy voice.

“What the fuck Nick! What the actual fuck is your problem!” She shouted down the phone; it was so loud I had to pull the phone away from my ear. “Well? What do you have to say for yourself?” There was a pause.

“First of all, Lizzy, I’m gonna need you to stop shouting at me!” I told her a little irritably. “Secondly, what the hell are you on about?”

“What am I on about? I’m on about Catherine!” She was still shouting but all be it not as loud.

“What about her?” I asked confused.

“What about her?” She repeated. “Are you being serious? Do you not even care that you ditched her?” Lizzy was pissed off.

“Wow wow wow” The memories coming back to me of last night. I was out on a date with this chick Catherine who was great fun until she ditched me for another guy. Then I went home with that slut, fuck I didn’t even get her name. “Lizzy ... what did she tell you?”

“That you fucking bailed on her at a bar, left her all alone!” She shouted.

“Lizzy stop shouting at me and talk to me like a fucking adult!” I shouted back. “And for the record, I didn’t ditch her, she fucking ditched me!”

There was a long moment of silence, the weight of what I said sinking in with her, so I pressed my advantage. I kept my voice calmer now as I explained. “So, we had dinner and it was great, I paid for it by the way but that’s not the point. We had a good connection, and she suggested drinks, so we went to a bar. I bought us more drinks and felt the night was going well. I went for a pee, came back and she was off with some other guy making out with him.” I had been raging at the time, but the little whore made it all better.

“Oh...” she said in a softer voice. “That’s ... um that’s not what she told me.”

“That is the truth Lizzy, I did leave her at the bar because she had clearly found someone else. If that guy bailed on her then in honesty, she deserved that.” I told her.

“Nick ... I’m sorry...” she said in a quiet thoughtful voice. “I ... that fucking bitch.” Her tone flipping at the realisation of what actually happened. “That little cunt, you wined and dined her and then she went off with some other bloke?”

“Pretty much.” I agreed.

“Oh Nick, I should have just asked you. I’m sorry I jumped down your throat ... what a horrible date that must have been.” She said in a sad voice.

“It’s cool, just in future ... don’t set me up on any blind dates.” I chuckled lightly.

“Ok deal.” She laughed back. “Let me send you half the money you spent? That’s not cool to spend all that money for nothing.” I could tell she genuinely felt bad, but I wasn’t going to take her money.

“Lizzy don’t worry, next weekend, let’s go out for dinner ourselves? We haven’t done that in a while.” I suggested.

“Yeah ok, I’d like that! I’ll pay though.” She said sternly.

“Won’t here an argument from me.” I laughed. We spoke briefly more before we said goodbye. I spent the rest of the day moving around the apartment like a zombie, the takeaway for dinner helping heal me a little.

I just made work on time on the Monday. My body and mind were not in go mode; it was very much in wish I had five more minutes in bed mode.

“You look like shit.” Jerry commented as I passed him.

“Still better looking like you.” I replied to him, not giving him a second glance. I had barely sat down at my desk when my cubicle was filled with the sweet aroma of perfume.

“Good morning, Nick” Stephanie greeted me.

“Good morning, Stephanie.” I replied as I swivelled my chair to face her. Today she had on a very professional looking pant suit with high heels. She was looking hot as ever.

“Good weekend?” She asked politely.

“Yeah, it was ok, yours?” I asked back.

“It was nice, my boyfriend and I went for a hike up the hills.” Ok good to know that she is not single. Not that I don’t think I’d have a chance with her anyway.

“That’s cool” I nodded, my eyes trailing to the small stack of files in her hands. “Are those for me?” I asked hopefully.

“No these are for Jerry, I don’t actually have anything for you, well not at the moment anyway. I do believe Mr Holcomb has a special task for you.” She said.

“Really? Did he say what?” I asked a little nervously. I had been happy flying myself under the radar all this time, but it seems Mr Holcomb is taking an interest in me. Suppose good thing is, it will probably piss off Jerry.

“No sorry he didn’t, he has some meetings this morning anyway.” With a smile she walked away. I tried to shake the thoughts of what he could want and tried to get on with some work.

It wasn’t until after lunch when Stephanie came to get me. I entered Mr Holcomb’s office and he was on the phone and indicated me to sit down.

“Hello hello Nicholas” he greeted me as he hung up the phone.

“Hello sir” I nodded back politely.

“So, I have a big task for you, my daughter is going to be working with us until she heads off to college. I’m a busy man so I want you to show her around, be her guide, be her tutor. Can you do that for me?” He asked but by his tone and demeanour it wasn’t really a question.

“I mean yes sure I can sir but maybe there would be better staff to carry the task out?” I didn’t really want some stuck-up little bitch hanging around me and snitching me up to her father.

“Nope, I think you are the exact right man for the job. You are young and ambitious, and I don’t want some sleazy creepy guy looking after her.” The image of Jerry instantly coming to the forefront of my mind. I mean there was a lot of other staff on our floor, a few women as well but it wasn’t clear his mind was set.

“Ok sir, sure I can do it.” I nodded in acceptance.

“Great, she’ll be here any minute.” He beamed with the apparent pride in his daughter. Sure, enough less that five minutes later the door opened. “There’s my sweet baby angel.” He said grinning widely as he stood up and coming around the desk. I was sat in a chair facing away from the door and only rose from the seat when he had embraced his daughter in a large hug, almost like he hadn’t seen her in months.

“Nicholas, this is my daughter Sydney. Sydney, this man will be looking after you while you are here.” I turned to face her and extended my hand. My heart sank, my face went pale, I somehow had enough muscle memory in my arm to keep my hand up. I stared at the brown eyed, brown haired girl in front of me. It was the girl from the bar, my supposed little whore.

“Nicholas, it’s a pleasure to meet you!” She smiled broadly at me as she shook my hand. No sign of recognition on her face. Either I had the wrong girl or she didn’t remember me.

“Yeah, um yeah ... it’s eh nice to meet you too.” I managed to speak out as I shook her hand.

“You can close your jaw now Nicholas.” Mr Holcomb chuckled. “I know my daughter is quite the stunner isn’t she.”

“Oh, daddy stop.” Sydney said she she swatted her father. The use of that word triggering my memory. It definitely sounded different from how she said it the other night.

“Yes ... yes, she is sir. Your daughter is exceptionally beautiful.” I naturally took a step back, I needed distance, I needed time to think.

“Now Sydney sweetie, daddy is a busy man at work so if you need anything you just ask Nicholas here, ok?” He said holding his daughters’ arms in his hands in a comforting way.

“Ok daddy, no problem.” She said in a sweet innocent voice. Nothing like the dirty foul mouth of Saturday night.

“Now Nicholas, to make room, use the spare office down the other end of the floor. Anything she wants you see she gets it but make sure she works, I don’t want her thinking this is completely a free ride.” He said the last part with a wink to her and she just bashfully giggled.

“Yes sir.” I nodded. The office down the other end had been empty for a while and was rumoured it would be the office of the senior manager, one below Mr Holcomb.

“Good man” he nodded back at me. “Now run along sweetie, daddy needs a few more words with Nicolas here.”

“Sure.” She smiled and stepped up and pecked her father on the cheek. “See you soon Nicholas.” She said to me as she skipped out of the office.

“Can’t believe she turned nineteen last week.” He shook his head disbelievingly as he walked round and sat behind his desk again.

“Nineteen sir?” I coughed a little. I had slept with someone who was ten years younger than me.

“I know can’t believe it myself. I remember only yesterday when it was her first day at school. Soon it will be her first day at college.” He said thoughtfully. Oh man if he only knew. Surely, I had got mixed up and had gone home with someone that look very much like Sydney. The girl I had sex with had to be twenty-one anyway to get in.

“Anyway...” he waved his hands. “I’m putting my trust in you here Nicholas. I want to see that ambition grow within you! Show me your true potential.” I wasn’t exactly sure how I could do that with babysitting his daughter now.

“I will sir.” I just said back to him. I could only imagine how he would react if I was right and it was his daughter I fucked.

“Good man, I’m counting on you!” He said as he waved me away dismissing me just like that. I left his office and headed for my cubicle, looks like I was moving to a bigger space for the time being.

“Shit did you see the ass on the new start.” I heard one of the guys mutter.

“Yeah, it’s massive but damn her chest looks even better. I’d love to rest my head on them.” The other guy agreed. I chuckled inwardly if they only knew who she really was I doubt they would be so vocal about their desires. I grabbed my things and headed for the office. I got in and closed the door. Sydney was sat on top of the large desk, her leg crossed over the other. Her skirt riding high because of it.

“Small world isn’t it.” She said in a much lesser innocent tone than she had used in her father’s office.

“What the fuck? If I had known you were...”

“I was what? The big bad boss’ daughter you wouldn’t have fucked me?” She said coyly.

“What the hell?” I looked around to make sure no one was looking or listening.

“Oh please...” she scoffed lightly. “He has no idea ... So, your name is Nicholas huh?”

“I prefer Nick but yeah...” I said as I walked to her side and put my stuff at the small desk to her left.

“Hmmm I like the name Nick ... Or maybe I can call you daddy...” She said the last word in that seductive tone she had used Saturday night.

“You can’t say that around here!” I panicked as I looked around again.

“Aww come on, where is that big dominant man that fucked me Saturday night?” She teased me.

“Saturday night never happened! I could lose my job if your father found out!” I made sure to keep my distance from her and keep my eyes away from her too.

“Oh I did happen, my pussy was still hurting last night from it ... want to see?” At this she opened her legs, spreading them. The way the desk was positioned, and she was sat, it wasn’t obvious to anyone outside what she was doing.

“Sydney, that’s really not appropriate nor professional!” I told her but I couldn’t help myself from looking. The small glint of light red panties was obvious under her black skirt.

“What’s wrong Nick? It’s not like you haven’t been there before.”

“Not the point, I didn’t know who you were and didn’t realise you were only nineteen. I assumed you would be at least twenty-one to get into a bar.” I had to turn myself away from her, I couldn’t trust myself not to look.

“Well, that’s the thing about having a beautiful body like mine and a seductive smile. Me and my friend walked right in.” She said.

“That’s not right...” I muttered. More out of the fact that it was confirmed I had sex with someone ten years my junior.

“Aww don’t be like that Nicky, look I’ll close my legs so you can at least look at me.” She said to me. I did give her a moment and then looked; she had indeed closed her legs. “There you go, you can look now.”

“Look Sydney, I don’t know how this will work. I don’t want to lose my job.” I told her truthfully. “It’s best I maybe get someone else to do this.” “Well, if you do that my dad will ask why you can’t do it ... why he specifically asked for you and then you pass me on. Don’t think he would be very happy.” Damn she had a great point. I was stuck. I really didn’t want to lose my job and switching with someone else is probably a sure-fire way of doing that.

“Right ok ... but we need ground rules.” I said sternly to her.

“Oh, I like rules, this is the daddy I took home.” She said with a wry smile.

“Ok straight away you can’t be referring to me like that!” I said to her, as much as it made my cock twitch when she called me it. It was definitely not for the office.

“Just in the bedroom ... ok...” she said with a pout. I took a deep sigh.

“No more sexual references, no sexual advances, this is to be strictly professional. You can never tell or let on that we knew each other especially the reasoning.” I said to her.

“Mmm look at you laying down the law.” She smirked.

“Sydney, that needs to stop.” I say sternly.

“Aww but where’s the fun in that. I mean you making all these rules sounds exciting to break them ... Means you have to punish me.” She said coyly as she bit her lip. I sighed again; I wasn’t going to win. This was going to be hell if I wanted to keep my job but by god, she knew how to press my buttons.

“Just please, act somewhat appropriate and professional please?” I said with a soft pleading voice.

“Ok fine dad ... I mean Nick.” She giggled and flashed me a wink. “Ok fine, where do we start?” She asked hopping off the desk. Her heels clicking off the floor as her large tits bounced a little.

“I’ll show you around the main office, where everything is and what not. Then I’ll show you the day-to-day business we do.” I say to her.

“Sounds super boring but ok let’s go.” She smiled as she headed for the office door.

 
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