It’s Monday, 7:45am and I have just finished getting ready for my first day at the office. I have opted for a slim black pencil skirt, a pink silky blouse, and a pair of shiny Jimmy Choo stilettos, with a smart leather handbag. My square rimmed glasses perched on my nose, and shiny red lipstick to match my manicure. It is my first day working as a Personal Assistant for Willie B. Hardigain, CEO of Interlink Investors. This isn’t quite what I expected myself to be after a 1st from Kings and a graduate programme, but needs must in the current economic climate. Truth be told I’m two months behind on my rent and my credit card is almost maxed. Still, no excuse for not being fabulous – I apply a second flush of red Chanel lipstick, and put it into my handbag, along with my lunch (packed lunch as money a bit tight right now) and some paperwork. As I open my Uber Taxi app, a little pop-up appears on the screen:
“NEW! Try UberPool today. Share a taxi and save up to 25% on your journey!”
Never one to miss a bargain, I book myself an UberPool, and 4 minutes later I am on my way to the office in a black Toyota Prius with tinted windows. Just as I am heading through the City, the taxi drivers sat nav lights up, and we stop just outside of Liverpool Street station to pick up another passenger. I move my Mulberry bag off the empty seat, and a smartly dressed gentleman aged around 45 enters the taxi. “I’m just going to St Pauls-” he says to the driver, without looking at me. He takes his seat and glances over.
“Err-“ he starts, talking to my shoes for some reason “Hey… er… hello. I’m Ben, RBS. Who do you work for then?”
“I’m with Willie B. Hardigain, just starting today” I reply, feeling a little awkward.
“Ah, I started at Hardigains a long time ago… Will open many doors for you. If you…”
He trails off, staring at my top. Confused, I look down to realise I haven’t buttoned up properly, and to my horror, the top of my red silk bra is on full display, with my areolas peeking over the red chantilly lace trim.
“Oh my-!” I hastily button myself up, feeling suddenly hot and embarrassed. I look over to Ben and can’t help but notice a little peak slowly rising and falling in his smart navy blue suit trousers. He inches closer towards me on the seat and runs his hand up my right leg. I frown at him, offended, and to slide further left towards the door. Inch by inch I move across the seat, until I can’t move any further, and have my back to the door, legs crossed tightly, glaring at him, yet tingling with excitement. He leans forward and runs his hand up my stockings, stopping when he reaches the smooth skin of my upper leg.
“Now really! Haha! Stop doing that- this is really so inappropria-“ I trail off, breathlessly, as I feel his fingers between my legs, gently massaging me through my silk knickers. He leans forward so his face is only millimetres from mine.
“I know Hardigain.” He says “We go way back. It would be a shame, a real shame, if your career in the City ended before it began.”
He moves his fingers further back between my legs and towards my bottom
I sit there, not daring to speak, as he unzips his trousers and begins stroking his cock. The radio is on full volume and the Uber driver is glued to his sat nav, unaware of what’s going on in the back seat of the car.
“Lie down” Ben commands.
Embarrassed, but excited, I lie on the back seat, and he kneels over my body, one leg on either side of my perfectly pressed silk blouse.
“Suck my cock” he says, looking me in the eye.
“Ben… I am sorry but I am NOT that sort of woman. I don’t care where you went to school or who your friends are or who you think you are. You are a misogynistic! This isn’t the 80s! Women in the city have the same right to be here and I am going to-“
Before I can finish, he stuffs his pulsing cock down my throat, thrusting violently, then pulling out and using the tip to smear my red lipstick all over my face and nose. I can’t help but secretly enjoy it as he pinches my nose, making me gag and gasp for air.
“You love that don’t you?” he asks, pushing deeper down my throat and making my eyes water “Call me “Boss” when I’m using your mouth”
“Yes Boss,” I reply, feeling a wetness building up between my legs. He leans back and pulls up my pencil skirt, revealing my silk knickers, and embarrassingly, the large damp wet patch at the front where I’ve soaked through them.
“Lie on your front” he says. Obediently I turn and lie on my front, and feel him pull my knickers to one side, and rub himself between my bum cheeks. I begin gently rubbing back against him, and a few moments later, I feel him grabbing my ass, and a warm trickle as he cums all over my bum. He moves back, pulls up his Calvins and zips his trousers back up, just before the Uber slows down at his St Pauls. Without a word, he exists the taxi, and I watch him stride towards his office, glancing at his watch.
Business as usual.
As I reapply my lipstick, pouting into my compact mirror, the drivers sat nav begins flashing again, and just a few streets later, the taxi stops in front of an old beautiful bank. For crying out loud! I’m going to be late if we keep stopping like this. The door swings open, and out strides a much older gentleman, a tatty briefcase and a copy of the Financial Times in one hand. He approaches the car, enters, sits down and looks over at me. “You must be freezing-“ he says- pointing at my skirt.
Oh no! I’ve completely forgotten to pull back down my skirt, and my stockings suspender belt and soaking silk knickers are in full view! “Oh my God I am really so sorry. It’s such a long story, I just… sorry” I smile apologetically, struggling to get my tight skirt back down in such a confined space.
“Well,” he says, in a deep rumbling voice “I think, you deserve a spanking for being so naughty, don’t you?”
Still so horny from my last encounter, I hear myself saying, without really thinking “Yes, yes I do Boss”. I bend over the seat and wait… and wait… and then finally a large firm hand stings my bottom from behind. I feel my bum getting hot after 10 or so spankings, and then, without warning one of his fingers slowly entering me from behind. Shocked, I squeal with pleasure, spreading my legs so he can go deeper. As he curls his finger upwards, I feel myself getting very wet and about to cum on his finger. Just as I’m nearly there he stops-
“No!!” I plead desperately, my voice barely audible over the car radio “Please don’t stop!!!”
Still sat in the chair, I see him unzipping his suit trousers… and teasing his hard cock out from the fly. Immediately, I move towards him, uncontrollable horny, and jump on top, facing him and riding him as he kisses me passionately and plays with my breasts. He grabs my bum and begins bouncing me on top, rocking me backwards and forwards. The car in front stops suddenly, and our taxi has to break at the last minute before a red light. The car lurching forward causes him to thrust deep inside me, and I scream out loud with ecstasy, and a second later, holding me down and pushing into me he cums deep inside of me, moaning out loud and squeezing my bum. I collapse on his chest, kissing his neck as he strokes my hair.
What an eventful first day at work!
The taxi rolls towards the Gherkin and stops.
“Remember to pull your skirt down bad girl!” he says, grinning as he zips up, and then exits the car.
The Uber driver is looking at me in the mirror, slightly confused as to why my makeup is messed up. Luckily, I manage to get myself straightened up and begin looking through my notes to make sure I am prepared for my first meeting. Only seconds from my destination, the sat nav begins flashing again and the car slows down!
Right… well… have some self restraint Billie, I tell myself, tentatively waiting for the door to open. To my complete surprise it’s-
“Mr Hardigain!!!” I exclaim, anxiously as my new boss gets into the car. Straightening up my glasses on my nose, I try my best not to appear nervous. “Billie!” he replies “What are the odds- are you prepared for our 12:45?”
“Oh yes Mr Hardigain I am. I was thinking, if we go in for anything less than 4% they’re going to know we’re keen to sell and try to drive the price even further down, so if we start at around 7 or 8%, the Chinese won’t want to risk… Um, Mr Hardigain??
Mr Hardigain is making it very obvious he isn’t listening, and has moved his leg ever so slightly across the seat to rub against mine.
“You are one sexy little minx” he says, looking me up and down, my stocking-clad legs crossed conservatively, leading down towards my extra shiny stilettos “Now I remembered why I hired you. You leave the negotiations to me, your job is to make sure I’m… nice and relaxed for meetings. Do you understand?”
“I think so Mr Hardigain. But you should know I have a first from Kings and…”
“- Every morning I want you in the office half an hour early. I will tell you what to wear. I will tell you what to do. I will tell you when to swallow when to lick my arse when to ride me and when to give me a massage and when to bend over and when stay still. Do. You. Understand?”
Shocked, I feel the wet patch and the front of my silk knickers spreading.
“Yes. Yes Mr Hardgain. Yes I do.”
“Good. So bend over and stay still.”
I manoeuvre myself in my tight pencil skirt and bend over. I feel his hands rolling my skirt up, over my stockings, then suspenders, then over my bum. I feel him grabbing my bum and jiggling it about.
“You want a fucking promotion?” he asks, two fingers gently resting on my clit “well how does Executive Personal Assistant with company car sound?” he asks. “A nice Mercedes S-Class with a driver?”
“Oh Mr Hardigain! Thankyou… that would be so lovely!”
“Well you’re going to fucking earn it Billie. Now beg me for a promotion-”
He moves my now soaking silk knickers to one side and begins doggying me very roughly in the back of the car, my face pressed hard against the seat. With sufficient motivation, I find myself to be very good at begging indeed.
“Pleaase…” I beg “Please Mr Hardigain… Please… I’m begging you… Please Boss…”
He puts his hands around my neck and begins choking me, going so deep my eyes start to water and my body begins shaking, trying to escape. I fall onto my font, and he climbs on top of me, grabbing my hair and pulling my head back, kissing me roughly and spitting into my mouth. Flattened onto the seat, with his full weight on top of me, I scream out loud, cumming very hard, twice in a row, as he goes harder and deeper, calling me a slut.
“Beg me for my cum” he drags my hair round so I’m facing him
“Please Boss, please can I have your cum. Please-“
I begin licking Mr Hardigains balls as he wanks himself, taking them into my mouth and looking up at him, cheeks stuffed
“OH YOU LITTLE… NASTY…”
He says, holding my head onto his cock and cumming down my throat. After he’s finished he keeps my head there, making sure I swallow every drop.
I watch, still aroused, as Mr Hardigain fastens his black leather belt. He pulls out a leather wallet and takes out some notes.
“By Thursday I want you to get some proper stockings. None of this hold up synthetic nonsense, I like silk. And I want a white blouse. Take this.” He hands me some money to buy the things with.
“Thankyou Mr Hardigain,” I say, leaving the taxi behind him and walking towards the office in my smart shiny heels.
At 12:45 myself and Mr Hardigain arrive on time at City Social for our client dinner and are directed to the private dining area. We walk in, and I feel prepared and confident about for todays meeting, but… oh no!!!
“Billie, this is Ben Thornton,” he says nodding me towards an all too familiar face. It’s ben from the Uber! Humiliated, and hoping he doesn’t say anything, I shake Bens hand
“Well hello Billie” Ben says, staring at my blouse, “An absolute pleasure to meet you”
“And this is Gregory Pennington” Mr Hardigain says, introducing me to the second older gentleman from the taxi!
Surely the world can’t be this small.
“Hi Gregory, really nice you could make it” I say, trying not to make eye contact.
“Oh no problem at all” he says, smiling at me “Luckily I got an exceptionally speedy Uber taxi earlier today” He winks at me as I stand there, feeling uncomfortable.
“Now Billie,” Mr Hardigain says, locking the door to the dining room and facing me. Ben and Gregory have told me a few interesting things about some skills you have that you appear to have left off your CV-“
I see Ben and Gregory watching me, as Mr Hardigain continues-
“We’ve been talking about the distinct lack of female talent in The City, and how fantastic it is that a young upstart like yourself had decided to pursue a career in finance.”
I stand there uncomfortably, not saying anything.
“Ben and Gregory are going to leave now. We need to have a talk about that… promotion I mentioned before”
The two other gentlemen leave the room.
“Mr Hardigain, I am so sorry! I’m not sure what they told you but basically it was all one big accident because what happened was, I took an UberPool, it’s this new thing that just came out and then I was in the car and then they got in the car and honestly I’m not the type of person who-”
“Here’s what we’re going to do” Mr Hardigain interjects, speaking over me “In order to be my PA I’m going to need you to exercise some bloody self-control. I pick my PA’s very wisely. No more of this ditzy promiscuous nonsense. Let this be an end to it. You will be MY personal assistant and no one else’s. Am I understood?”
I prickle with embarrassment.
“Yes Mr Hardigain” I reply.
He steps towards me, towering over me even in my heels and pulls me by my waist towards him. Our bodies pressed against each other, we kiss deeply and passionately.
To be continued…!