I Fucked My Boss’ Daughter
Copyright© 2026 by Highlander90
Chapter 1
Fiction Sex Story: Chapter 1 - 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
“Just another few lines.” I muttered quietly too myself. I just had to check another few lines of this document and I could get away from this cramped cubicle for the day. Turn this overly bright monitor off and retreat to the sanctuary of my apartment.
“Last section.” I did my best to concentrate on the work. My eyes had already flicked to the time; official finishing time was well over an hour ago.
A couple of minutes later, I was finished. I could have left this for tomorrow, but I know tomorrow I will get more reports to complete. I move the mouse cursor over the start menu, clicking the power option and click the shut down button. Official finish time was five and it was now after six. I slowly tossed my suit jacket on and grabbed my briefcase.
“Leaving so soon?” The pompous dull tone of one of my co workers said. His name was Jerry and he was a total kiss ass. He was always first one in and last one to leave, it was so clear he was so desperate for the vacant senior managers role. I personally would love to get it just to get one up on him.
“It’s six o’clock Jerry.” I said flatly as walked past him.
“That attitude will never get you far.” He said in a disapproving voice.
“Fuck off Jerry!” I replied as I flipped him the middle finger as I left.
I worked in a large cooperate building in the city. My office as they like to call it, was on the seventeenth floor. The building had three elevators, and it was the middle one that opened. There was already someone inside.
Anyone coming from above was either in the legal department, HR, or executives. I did my best to give her a courtesy nod and a small hello, making sure to keep my eyes on her face. She was an absolute stunner. She had dark blonde hair tied up in a bun behind her head. Her face had just the the right amount of make up to make her blue eyes pop. She wore a black blazer with a white blouse that looked like it was busting at the seems. To say she had a large chest was an understatement. A short black skirt with tights and heels completed the outfit. Not to mention the designer handbag hanging off her arm with her phone in hand. She only gave me the briefest of smiles as the elevator door closed.
It was an awkward decent until she got off at the fourth floor. Her heels breaking the silence. She was in the executive department as the fourth floor was only reserved for their cars. Myself, I was another two floors down.
As it often was the parking lot was very empty. I had made sure that when I got a promotion from the customer service department, I got my own space. It was always a fight for spaces before and was even worse going for public transport.
I climbed into my pride and joy. A cherry red BMW Z4 with a hard top. It was not the most flashy or fancy car, but I had always wanted one so with my bonus I got one.
As the crow flies, I only live about fifteen to twenty minutes away but with traffic it doubles.
I get back to my apartment block and park up in the garage. It is a six-floor building with the garage taking up the ground floor. I managed to get a great price on a one bed corner apartment on the top floor.
My apartment is nothing special, but it is mine. All thanks to my parents I am mortgage free at the age of twenty-nine. There was a small entrance hall which then opened into a modest open planned kitchen and living room area. There was a large window in the opposite corner that let in plenty of light. The bathroom was to my immediate right, and the bedroom was the door after. I headed for the bedroom and striped down, planning to take a shower. Once undressed and I walked into the bathroom and leant against the sink. Looking at myself. My short deep brown hair not as well kept as it was this morning. Small bags and droopy eyelids hid my brown eyes. I ran my hand across the dark stumble that had formed along my narrow chin.
I did not consider myself ugly and personally thought I was a decent looking guy, but it has been two years since I have had a girlfriend and several months since I have been laid. With a deep sigh I get myself showered.
My night followed the normal routine. Shower, dinner, tv then bed. I was in bed when my phone went. It was my older sister of two years.
“Hello Nicholas!” Her voice said cheerfully, I sighed deeply. My birth name was Nicholas, but I have never used it apart from official documentation. I have always gone by Nick whenever I can.
“Hello Elizabeth!” I replied, knowing it would annoy her just like me. Again, her given name was Elizabeth, but she always went by Lizzy. I mean we both could have legally changed our names but neither of us would do that to our mother.
“Ok ok touché!” She spoke. “Anyway, what are you doing this weekend?” She asked, frantically.
“Eh nothing probably why?” I replied, laying on my bed staring at the ceiling. I do not know why she even asked, I barely have plans for the weekend. I have tried to go out on dates before but after a bad run, I gave up.
“Perfect, my friend Catherine...”
“Nope, no way!” I said cutting her off. I knew exactly where she was going with this and I was not going on another blind date with one of my sisters’ friends. Oh, I need to clarify that the blind dates with her friends before having turned out to be girls that my sister met at the hairdressers, at the supermarket, on the train. They are not really friends.
“What? You do not even know what I was going to say!” She said a little defensively.
“I do, you were going to say that your friend, insert name, is recently single and that you think we would make a great match. She is funny, smart, and good looking. Insert description, oh she’s, blah blah years old as well.” I rambled off a speech I have heard a few times.
“Well ... her name is Catherine, she has been single a while, ex boyfriend moved away or something. She is funny and smart, a very blonde girl. She has a large chest like I know you like and she is only a year younger than you! What is the big deal?” Again, she sounded defensive, even offended.
“Because every blind date you set me up on, you fail to mention their red flags.” I tell her.
“Red flags? Name one!” She scoffed.
“Ok ... so Violet was never off her phone, Natasha was a racist, Braelynn was a stuck-up bitch and don’t even get me started on Tatiana!” I said to her rattling off names.
“What was wrong with Tatiana? She was a lovely girl?” Lizzy asked.
“Lovely? She was a fucking physco! She threatened to rip the waiters balls off for bringing over a vodka Coke not a JD and Coke.” It was quite scary and that was just a simple mistake with a drink.
“Well, if he got it wrong...” Lizzy tried to defend.
“Lizzy! She threatened him with a knife.”
“Ok ok so some weren’t great, but Catherine is different!” She spoke. I sighed deeply and weighed my options. Have a date with a stranger or spend the weekend alone.
“Fine...” I conceded.
“Yeah? You will?” She asked excitedly.
“Yes, I mean I don’t have anything better to do anyway.” I sighed.
“Exactly! Ok perfect, I will text her and send you the details. How does seven on Saturday sound?” She offered.
“Yeah ok, where?” I asked.
“The olive grove?” She suggested. I nodded silently, I have been there before, and it is a good place for a first date. Classy and nice but not overly expensive.
“Ok yes, go for that. I will make a reservation.” I tell her. Lizzy and I speak for about another ten minutes before we hang up and I get to sleep.
“I’ve already been here an hour Nick” That dull voice said as I passed Jerry who sipped his mug of coffee like in some victory. I just ignored him and go into my cubicle, taking a deep sigh as I press the power on button.
“Good morning, Nick.” A pleasant voice said from behind me. The voice belonged to a tall slim black-haired girl called Stephanie. She was a sort of secretary come admin for the floor. She was a very pretty girl and pleasant but her presence this early was never good.
“Morning Stephanie” I replied out of politeness.
“These are the reports that need completed by end of play today.” She said as she placed the pile of files onto my desk. I closed my eyes and sighed silently as I looked at the stack. I was in for one long hell of a day.
“Thank you Stephanie.” I replied trying to not sound pissed off. It was not her fault. She was just the messenger.
“Oh, and Mr Holcomb wants to see you in his office.” She said with a slightly down tone. Being called into the boss’ office this early was never good. Especially on a Friday.
“Just now?” I prayed for later.
“Mhmm.” She hummed and then left.
“Great” I muttered to myself as I slowly got up. I did my best to ignore Jerry who was tutting and shaking his head.
“Fucking Jerry” I hissed quietly as I head to the far end of the office. Mr Holcomb’s office took up one whole side; it was bigger than it needed to be but in fairness he needed a big office to fit his ego. I took a deep breath before knocking on his door.
“Come in” I heard his gruff voice call back. As I entered, he was stood by the large bay window drinking coffee. He was dressed in his usual tailored suit. Mr James Holcomb was a small plump man with a bald head, a round belly, and an aged look on his face. He was in his sixties but could easily pass for seventies.
“Hello Nicholas, come in and have a seat.” I gritted my teeth like I always did when he used my given name and walked towards his desk, taking a seat. Even the seats were over excessive.
“Lovely day isn’t it.” He said, admiring the view he had out of his window.
“Yeah, it is.” I agreed simply.
“Mmm” he hummed as he took a drink of coffee and took a seat in his large leather chair. “Tell me Nicholas, how long have you been working for me?” He knew the answer, he made it his job to know everything.
“A few years or so ... sir.” I added at the end. I was not this man’s biggest fan, but my father always installed respect in me. There was a small element of fear as well. He was known to become extremely angry and a couple people have been fired as a result. So, it was easier to just show him the respect he wants.
“Mmmmm yes, I remember when you first started, you had such drive, such enthusiasm.” He tutted. “Now ... now not so much. I mean I put great faith in you. Thought you would go all the way to the top, but you just do not have that in you anymore. You don’t have that thrive like Jerry does.”
I winced at the mentioned of his name, Jerry was a fucking kiss ass anyway. There is no way he would go anywhere. He does too much for Mr Holcomb. I did have enthusiasm when I started but when every day turns into the same and you start experiencing Groundhog Day it is hard not to feel complacent. I have been putting in effort but admittedly my work effort has dipped. The only reason I have not quit is because it pays well and to be honest, I do need this job.
“I can only apologise sir; I just like to get my work done and keep my head down.” I told him. I just wanted to do enough that he had no grounds to fire me.
“That can be a dangerous attitude Nicholas, I want to see that drive, that enthusiasm back with you.” He punched his hand to emphasise each point. “Can you do that for me?”
I took a deep sigh before replying. “Yes sir, I will do my best.”
“Good lad! Keep up the splendid work.” He said waving his hand to dismiss me. I nodded my thanks and left the room.
It was indeed a hard ass, ball aching day. I kept my head down and did my best to fire through them whilst not letting standards slip.
“Mr Holcomb finally talk sense into you?” Jerry jeered as he stood outside my cubicle.
“Told me I had to pick up your slack!” I replied not turning to look at him.
“Ha” he barked. “My slack? Yes, right I am the best there is in this department.”
“Then why haven’t you been promoted then?” I shot back. I grinned at his initial silence.
“Eh well, Mr Holcomb needs me and unlike you, I don’t want to let him down.” He finally said.
“Oh, I see, maybe that’s why he offered me the senior position then.” I lied.
“He what?” I almost let out a laugh at his sudden outburst. “There is no way. That is not true! You are lying!”
“Why would I lie?” I teased him.
“No no, that is my position! You are lying! Fuck you!” He spat as I heard him storm off.
“Ok that was worth it.” I chuckled to myself. The smile quickly faded as I waded back into the work.
By the time I was finished and drove home, I had a quick bite to eat and shower then was in bed. Sleep quickly consumed me.
My sister texted me several times the next day to make sure I would not bail on Catherine. I promised I would not. Even as much as it might be hell, I would never do that.