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First Day

Author: Maxiwick
last update Last Updated: 2025-10-28 03:41:50

I knocked on Mr. Conti's door on my first day of work, not sure what to expect and a little bit nervous.

" Come in," he said in that stern, impersonal tone.

I step through the door and stop, too intimidated to go any further.

He looks up from his work and with a confident air says, "Close the door and come sit."

I close the door behind me and the air in the room immediately feels tense, like there isn't enough. I walk to the chair in front of his desk on shaky legs. This man is too good-looking to be human. It's not fair. I sit in the chair as his beautiful green eyes follow my every move.

Once seated, I look up, desperately hoping he suddenly became less hot. He stands, undoing the button on his suit and walks around his desk. He casually sits back against the edge of his desk in a pose that belongs in a men's advertisement. His hands grab the edge of the desk and I feel myself get a bit wet watching them tense and flex for a moment. Just imagine how they would feel on me.

"I thought I'd run you through my expectations and show you what I like," he says calmly.

"Yes, sir," I nod. I look for a notepad to take notes but I must have forgotten to bring one.

"Don't worry, this will be more of a demonstration. No notes needed," he says in a husky tone.

I look up at him to see he's removed his jacket and is now rolling up his sleeves to show off toned forearms that have me squirming.

He walks over to me and leans down on the armrests. His face is inches from mine when he says, "Your squirming is giving you away."

He lowers to one knee and before I can register what's happening, he grabs my skirt on either side of the slit and rips it right up to my waist, exposing my lacy underwear. I gasp in shock and he just chuckles.

"This is going to be so much fun," he teases. Next, he rips pulls open the front of my blouse, the buttons falling and rolling along the floor. I'm staring at him in complete shock, not sure what to do but also paralyzed by my arousal.

The smirk on his face tells me he knows the effect he has on me. Keeping me hypnotized by his stare, he brings his finger to my center and easily sinks into me with how wet I am. "F-ck," he groans as I whimper.

He pumps his finger a few times, then adds a second. My head falls back as my hips start moving, wanting more.

"I wasn't expecting you to feel so tight or to get so wet," he says, his composure fraying at the edges.

I can't speak, too overcome with sensation. I'm panting and trying to hold back from making noise since we're in an office, but when he latches onto my nipple and sucks, I can't help the scream that escapes.

"F-ck, I wasn't going to take it slow, but that won't be possible anymore. You're too goddamn tempting," he says. He quickly takes away his fingers, making me whimper at the emptiness.

He stands me up and basically carries me over to his desk since my legs are like jello. He faces me away from his and bends me over the edge. He kicks my feet apart and commands, "Hold on."

I barely have time to grab the edge of the desk before he rips my lace thong and rams into me from behind. I call out from the fullness of the intrusion. He pumps into me hard and fast, having lost all control. I love the sound of his grunts and the slapping of his balls against my clit.

The orgasm that was interrupted before is back on track and building higher. Mr. Conti surprises me by landing a hard slap against my ass that I can feel all the way in my toes. My forehead drops to the desk from the overwhelming sensations and I beg, "More."

I can feel Mr. Conti's excitement as he grows inside me and praises, "You're going to be the best assistant I've ever had."

He slaps me again and again, alternating sides, until my ass cheeks are numb. I'm right there and he knows it. He leans forward, placing his chest on my back. The weight of him against me makes me feel trapped. That feeling combined with the hard bite he places on my shoulder, sends me barreling headlong into the most powerful orgasm of my life.

I scream out his name as I cum and cum. He swears and cum, dumping such a big load in me that it leaks out, down my thigh.

A knock on the door has me coming back to reality. I panic. It's my first day at work and I had s-x with my boss. Even worse, now we're going to be discovered. The knocking keeps going but Mr. Conti says nothing.

The knocking gets louder and more insistent until it sounds like an alarm.

I open my eyes and suddenly I'm on my back looking at the ceiling. I sit up and look around to find that I'm in my bedroom. A quick look down shows that I'm in my bed. In a daze, I reach over to my phone to turn off the alarm.

I finally fully wake up and feel dread at the realization that I just had a s-x dream about my new boss that I was starting work for today. Oh god, it's going to be so much harder to face him now! I'm going to have to look at him and know I had an orgasm while dreaming of him taking me in such a brutal way.

I take a cold shower and dress in an outfit that has no slit and no buttons. Better safe than sorry.

 

A week later I enter my new office with renewed energy. It feels like 3 months ago when I started at Magna Corp, only better because I would be meeting with Tony at the end of the work day to debrief. (He quite literally entered it into our shared calendar as Debrief).

At reception, I am handed a badge and told to proceed to the top floor. The reception at the top floor then directs me to a corner office. I'm starting to get curious about who I'll be working for. I assumed that Mr. Conti was saving me from Mr. Finch and they might not actually have an open position for me, especially for an executive.

I enter an office with two desks with a similar set-up to my last workplace, only this place is bigger and more modern, which I prefer. There is a door at the opposite end to the room that I assume leads to our boss's office. The best part, though, is that we have our own little break room and private bathroom!

"This is Jessica," the receptionist explains, "She is the first assistant and you will answer to her. I'm Claire if you need anything else."

Claire leaves and I turn to Jessica and reach out to shake her hand, "I'm Alexa, it's nice to meet you."

She looks at my hand with distain, then walks around me and says, "Follow me."

She takes me on a light-speed tour of the office where I do my very best to keep track of every name and direction she gives me. Once back in our office, she gives me a brief overview of what my duties will be and, had I not been an executive assistant previously, I would have been lost.

I spend the first couple hours of the day tracking down the IT guys to get access to all the systems. Marty, the IT guy, is super sweet and wishes me luck with Jessica, "I'm scared of the girl, everyone is. She sucks, but for some reason she doesn't get fired. Stay on her good side, if she has one."

When I return to my desk, around 10am, with my access all sorted, the door to Mr. Conti's office is open and I can see he is in deep concentration at his desk. Just as I'm about to sit, I hear him yell out, "Coffee!"

Jessica had listed that as part of my duties, so I look to her and ask, "How does he like his coffee?"

"Your first task and you're already asking questions," she shakes her head at me like I'm pathetic, then returns her attention to her work.

While I have no clue how Mr. Conti takes his coffee, I am thrilled to get to use the fancy coffee maker in our private break room. Judging by Mr. Conti's intense demeanor and manliness, I decide to keep it simple and go with a black coffee.

I check to make sure he isn't on a call, then enter the office and place the coffee on the coaster on his desk.

"How is your first day so far?" He asks, surprising me. I assumed there would be no chit-chat.

"It's been great so far," I say, "I have access to everything and I love the coffee machine."

He takes a look at his coffee and asks, "Black?"

"Yes," I respond, "but I can grab milk or sugar if you need."

"No, this will be fine. Thank you." He doesn't look back up after that, so I take it as my cue to leave.

I head back to my desk and intend to start on the list of morning tasks I'm supposed to be doing when Jessica looks at me with a saccharine smile and says, "Don't worry if he didn't like the coffee. It's hard to get it right the first time."

I nod, not bothering to tell her he accepted the coffee. I don't know her well enough to understand her intention in saying that comment, but I know it isn't kind. I assume I can now check black coffee off of the list of coffees that Mr. Conti likes. I'm watching and he hasn't taken a single sip. I'll have to try something different tomorrow. I wonder why he didn't just tell me he didn't like black coffee. Maybe he was trying to be nice on my first day.

The rest of the day seems to go fine until 4:30pm comes around and Jessica dumps a load of urgent work that needs to be done on my desk. I text Tony to cancel our plans and get comfortable for the night ahead. Jessica stays until Mr. Conti leaves. She had been ready to leave for an hour, scrolling through social media on her phone. When Mr. Conti came out of his office she pretended to stand up like she just happened to be leaving at the same time.

I can't help the huge smile that breaks across my face. Her desperation is flowing off her in waves and you can tell Mr. Conti is annoyed. I quickly look down towards my work so that Jessica won't see my smile. After just one day, it's already pretty evident what kind of person Jessica is. She gave me all this urgent work, yet she sat there doing nothing for the last hour.

She doesn't know that anything is better than working with Mr. Finch. Watching her attempts to land Mr. Conti might actually be entertaining. I'll have so many funny stories for the gang.

I get a text from Tony saying he'll miss me and not to work too late. I send him back a text asking him to do some cyberstalking on Jessica. He loves that kind of thing and after the little tricks she pulled today, I assume there is more to come. He promises to get to me by the end of the night and I can't help the smile that comes to my face. I'm so lucky to have met Tony. He is a really loyal friend.

They say 'know thy enemy' and I intend to do just that.

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