Mrs. Cross – Bitchy Boss xxx

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By Lauren McAllister

I was 47 years old, recently divorced and I hadn’t had sex since Pres. McKinley was assassinated. Oh sure, I was a successful businesswoman. I managed a staff of 107 people for a company with a net worth of over $25 million. But there are some things that career and financial success just can’t replace…like a tall sinewy man with a Brazilian nutjob, sporting a righteous woody with your name on it. Let’s just say I was really feelin’ the need to breed. But did I really want to spend my nights roaming sleazy bars on the hunt for men half my age? The answer was probably yes. But then something unexpectedly popped up…And I don’t mean the mail boy’s boner.

It was just another boring shitty day in a long line of stultifying 24 hour turdfests. I was seriously considering the advantages of an early retirement when a vision of golden light walked past my office door. Her name was Cassidy and she was so young and fresh, you half expected her to be holding up a bar of Irish Spring Soap. She’d only been with the company for a few months and thus wasn’t burned out and suicidal yet. Something inside me stirred when I caught sight of her. This incredibly pretty (in that fragile Celtic sort of way) goddess awoke a pussy that until now had been suffering from severe disuse atrophy. I’m not really that bi when I’m fully sober, but this girl was something incredibly special. Perhaps I was going through a mid-life crisis or something but I became totally schoolgirl smitten. There was obviously only one sensible thing to do. I closed the office door, lifted up my skirt, and had a glorious wank right there at my desk. And every nano-second of that totally blissful self-abuse, while I was battering my little sex button unmercifully on the path to a glass-shattering orgasm, I fantasized about innocent Miss Cassidy and the inestimable pleasures to be found within the confines of her pencil-skirt. My blistering climax was some kind of wow and I quickly treated myself to a second round on my mound. I was sorely tempted to just stay there and wank myself into unconsciousness but the fucking phone rang and I had to get back to work (good little businesswoman that I am). But when I got home that night I brutalized my twat to the point where I almost called the police and myself. Something had to be done about this perplexing situation.

The next morning, I marched into Cassidy’s tiny cubicle on the second floor. She almost spit out her perfect teeth, she was so surprised to see me. I recall when she first applied to the company; we almost didn’t hire her because she had severe money problems. Her husband had been unable to find a job for almost a year and a half and they were completely broke. In the business world, people like that are considered untrustworthy and lacking the stable home environment essential in a candidate for long-term employment. Lucky for me, we gave my darling little heartthrob the job anyway; because her unsound financial predicament made her blissfully perfect for the evil little plot I had in mind.

“Is… Is there something I can do for you Mrs. Cross? ” she stammered with her lilting accent and turning the color of vanilla ice cream.

“I’ll come directly to the point, Ms. Graham. I’m considering taking on a new personal assistant. This job requires someone who is willing to give me 110% at any hour of the day or night. Is that you Ms. Graham?”

“Personal assistant?”

“Of course, the person who secures this position will be more than appropriately recompensed. What is your current salary?”

“Well, it’s… I’ve only been here a short while… It’s a wee bit over $500 a week.”

Everything about her was turning the contents of my skirt to butter but it was vital that I retain the appearance a hard ass. “There will be a probationary, of course.”

“Oh, of course.”

I could see that she was becoming hopeful. The trap was now set and all I needed was the adequate amount of bait. I weighed the sort of monetary figures I should blithely toss around as she leaned forward across her desk like a child in a Dickens novel. And yes, I took a quick gander down her top.

“For the first month, if I decide to take you on (I looked at her doubtfully, to build up the tension), your salary would only be $1500 a week.”

Cassidy’s mouth dropped open (gosh, there were so many things you could do with a pretty mouth like that). It was obviously a sufficient amount of financial chum to have thrown in the water.

“If you manage to survive these first four weeks, and I assure you it will not be easy, your weekly take-home pay will rise to anywhere between $2500 and $5000, depending on how pleased I am with your absolute devotion to me.”

I stroked her blushing cheek as Ming the Merciless would have done before sentencing a poor virgin to be ripped apart by Mongo wolverines. All Cassidy could see was a way out, the solution to all of her problems (all I could see was her to-die-for cleavage).

“I can… I mean, I will be that thoroughly devoted person. If you were to give me this wonderful opportunity, I promise I would never ever let you down.”

That accent! That face! I wanted to beg her to marry me (somewhere where it was legal). Again, I stared long and hard at her sweet anxious countenance (while still stroking her cheek). I built the moment up from tense to the point where I thought she might lose control of her bowels. Then and only then did I gift her with the incredibly glad tidings.

“Mr. Dawkins from accounting will be along within the hour with your first week’s pay,” I fake huffed. “I am giving you your wages in advance so you’ll already be incredibly indebted to me. To understand what I’m saying?”

“Oh yes Mrs. Cross! Thank you Mrs. Cross! Whatever it takes.”

“Then I suggest you spend the remaining time you have down here putting your belongings in a box, ready for your big move because I don’t like to be kept waiting.”

And with that final uber-bitchy declaration, I goose-stepped out of the room (not really, but you know what I mean) and left her to bask in the glow of her unexpected good fortune.

I gave Cassidy the large office next to mine. Vice presidents don’t have offices that nice…well, not anymore, they didn’t. I wanted her to be so in love with the job that no amount of personal debasement and humiliation would seem dissuade her from holding onto it (and there was a considerable amount of it heading her way). She was already wetting herself with joy when I walked into her new digs and the amazing windfall that had just befallen her was just about to get a whole lot more amazing.

I snottily dropped $5000 in cash on the desk in front of her. “You’re going to take tomorrow off and spend this money on a brand new work wardrobe. I want it to be very sexy but not slutty and if you bring me back any change, you’re fired. Do we understand each other?”

“Yes Mrs. Cross,” she purred, turning my privates to jiggling jelly.

She actually curtsied. I almost smiled but it would’ve blown my very convincing “boss from hell” persona. “And take this card. It’s the finest restaurant in town. I want you and your husband to go there tonight to celebrate your new job and how grateful you are to me. Everything, including the champagne, is already paid for. You are not to tip the waiter or the valet.”

I thought she was going to faint (If she had, I would have eaten her out right there, while she was unconscious – was that bad of me?) as she picked up the scattered hundreds off the fine oak surface.

But there’s a price to be paid for everything.

“Oh, and Friday night, I want you to stay over at my house for an intense get-to-know-each-other session. Of course you don’t have to come, but I believe it would be beneficial to our employer/employee relationship.”

“Of course! I am at your total disposal 24 hours a day, whenever the need arises,” she assured me, depositing the big wad of bills in her purse.

I grabbed her chin, pulled her towards me and softly kissed her angelic forehead. I practically came! “Good,” I smiled warmly. “Then I will see you back here on Friday.”

According to Henri at the Blue Duck, the couple were deliriously happy with their new circumstances. Expensive cuts of beef were chewed and swallowed, numerous flutes of champagne were raised and I’m sure, later on that evening, their genital apparatus were utilized countless times to their full advantage (that lucky bastard).

Friday evening was a slightly less public affair. Cassidy and I had an intimate dinner on the south–facing terrace, followed by a heavenly massage and a dip in the hot tub. She was so nervous taking her clothes off in front of me, I wanted to get down on my knees and stick my tongue up into her fallopian tubes. So cute and so shy! And her body was and all-you-can-eat buffet of sexual delights. She had breasts that would have made female graphic novel superheroes jealous. It required all my self-control to keep my hands off all her lovely bodily accoutrements. I was afraid that she might have to petition the courts for a restraining order against me.

The massage calmed her nerves somewhat and the champagne in the hot tub further mitigated her anxiety. I was very brave and refrained from staring too obviously at her naughty parts. There would be plenty of time for that later.

“You see Ms. Graham,” I haughtily informed her as hot foamy bubbles congregated around her tits, “this job requires that we have no secrets from one another. Absolute trust must be maintained and nurtured at all times.”

“Of course,” agreed my slightly tipsy pixie. Oh, how I envied those hot foamy bubbles.

“I’m so happy to hear you say that. I told the maid to move your things into my room.”

I could see this raised a small alarm bell in her perky little head. I moved immediately to take her mind off it.

“I have to say, you’re doing very well so far. You might be just the girl in looking for”

She smiled and I plotted.

Cassidy was practically shaking with nerves as she climbed naked into my bed, staying as close to the edge as she possibly could without falling off the mattress and onto the floor.

“Do you masturbate, Ms. Graham?” I asked matter-of-factly.


“It’s a simple question. I’m more than willing to admit to you that I enjoy a good self-pleasuring at the end of enjoyable evening.”

“I suppose I do…sometimes,” she reluctantly admitted. I’m sure her mind was whirling a thousand miles a minute trying to figure out where this line of questioning was headed. She was about to find out.

“The truth is, I’m very much inclined to give myself a terrific clit spanking right now.”

“Would…would you like me to leave and come back in a few minutes?”

“No, I’d like you to join me.”

Her face when his white is a dead albino.

“Surely you must feel a little need for something physically yummy after all that wine and the massage?”

“I suppose… But…”

I didn’t let her finish her sentence, of course. I quickly pulled the sheet off her naked body and lay with my legs splayed out beside her.

“Let’s turn our “nub rub” into a little game, shall we?” I suggested. “Just as we’re about to cum, let’s yell out ‘now’ to let each other know when it’s happening.”

I press my two fingers into the plump wet folds of flesh between my legs to let her know that it was time to start. Cassidy lay there, as stiff as a corpse in a salad crisper.

“Please don’t make me do this alone,” I whined. “It’s very embarrassing.”

With the utmost reluctance, her small delicate hand slowly made its way down her smooth slender tummy and burrowed deep into her mesmerizing honey pot. The view of her timidly pounding the mound was absolutely intoxicating. My own finger fireworks increased in intensity as I witnessed her nerves giving way to the primal forces within her. It wasn’t long before my frothing vagina was making loud squelchy noises as I beat its little brain in. My leg muscles tightened, my breathing quickened and my… Oh my fucking God! “NOW!!” An orgasm rolled over me like an oversized bulldozer. My abdominal spasms were so strong I thought I was going to break a rib. Vast waves of pulsating pleasure poured out of my clitoris and laid waste to my writhing, twitching body. Visions of Cassidy’s naked form filled my imagination as my climax reached grand mal proportions. Drool dribbled down my chin and utterances of an ungodly sort were loosed from within my throat. In short, I was having a pretty good one!

Once I had calmed myself down, I turn my full attention to my masturbating mattress pal. She was gamely “giving it a go” but clearly struggling to attain the dizzying heights of arousal that I had just achieved.

“Come on baby, you can do it,” I whispered softly in her ear as she attempted to whap herself into a frenzy. “Play with your tits. Torture your nipples. Force yourself to cum.”

Cassidy kindly complied with my request as I stroked the inside of her thigh. My little plaything’s face was completely and utterly edible as it contorted in pre-orgasmic grimaces. I knew she was rapidly approaching her “now” moment. Her picture-perfect pelvis lurched up to enthusiastically receive the thrusting of her frantic fingers. Moans began to leak out of her like the air out of a Walmart tire. The “closer” she got, the further up her leg my hand drifted until her gyrating fingers were tapping onto the back of my knuckles. “Now!” she piteously exclaimed.

As she bucked and self fucked, I allowed my hand to briefly slide up the length of her glistening pussy. This was my one moment to strike and it had to be timed perfectly. I slid my left leg on top of her upper thighs and put my hand upon her engorged breast as her contractions began to wane. Those few seconds after a woman cums are when she is at her most vulnerable and I was poised to take full advantage of the situation.

I stared deep into her gorgeous hazel eyes with a longing that bordered on Vampirish. “You are so goddamn beautiful,” I sighed and plunge my tongue deep between her quivering lips. It was a kiss so soft and otherworldly it almost made me cry. But this was no time for tears. I quickly slid on top of her, pressing my breasts into hers. She gasped, realizing what was just about to happen. I kissed her again, driving my vaginal mound hard into her dewy flesh, our overflowing vaginal juices mixing together as a ground myself into the core of her femininity. Cassidy surrendered to the moment and returned my passionate smooch, then opened her legs wide to allow me full access to her sexual volcano. The feel of her velvety skin against mine, her swampy cunt against my own bubbling lake of desire had me humping her like I was attached to a paint shaker. Cassidy grabbed my ass and pulled me ever closer, her legs wrapped tightly around mine to thwart any thought of escape. She came three times in rapid succession, each one more magical and violent than the last. I managed to get two more gut-busters out myself, before I fell off her in satiated exhaustion.

As soon as she had regained her senses and mortified embarrassment set in, she sweetly asked if she could go to sleep and promptly rolled over, facing away from me. I really wanted to spend the night cuddling with her but wisely decided to give her some space.

When Cass awoke in the morning, she sat up in bed holding the blanket tightly over her perfect breasts. It didn’t take a genius to realize that she had something troubling on her mind. And it certainly didn’t require an IQ of 145 to figure out what it was. I have to say, it takes a lot of courage to quit your job while you’re lying naked in bed with your boss. Of course, there was no way I was going to give her that opportunity.

“I think we had a very successful evening and forged a very strong communicational bond between us.” I evaluated coldly. “That is vital if this business relationship is going to function at a high level.” Yes, I was really pouring on the corporate doublespeak here. “I’m going to up your probationary salary to $2000 a week, retroactive.”

Cassidy’s expression changed and her iron grip on her breast-covering bed sheet weakened.

“I know I kept you from your husband last night but I will make it up to you both. There is a suite booked under your name at The Four Seasons for the weekend. Do not attempt to tip the bell boy or room service. Any service the hotel provides will be available to you free of charge.”

Cassie generously let her modesty sheet drop into her lap. There those perfect tits were again!

“Well, I’ve got countless things that need my attention and you and your hubby have some packing to do. Let’s have a quick shower together and be on our way.”

Of course, she hesitated. Now it was my turn to be nervous (though, it was completely undetectable).

Cassidy eventually smiled weakly and nodded her head. And lordy, what happened in that little wet cubicle made the very majesty of the gods, back to the beginning of time; seem like a fart in a mud puddle.

Now, I just have to figure out what I’m going to do with myself for the next 48 hours while that unemployed asshole is fucking my woman!

Copyright 2014 Lauren McAllister

These naughty books by Caffieri and Lauren are available on Amazon.

Laid in America by Caffieri and McAllister

Erotic Super Shorts Vol. 1 (FREE BOOK) Cristiano Caffieri

Okay, Who Gets Which Hole? Lauren McAllister

Erotic Super Shorts Vol.2 Cristiano Caffieri

Farting Through Nylon Lauren McAllister

Cock-up in Miami (A Johnnie Faero Story) Cristiano Caffieri

He Filled up My Curriculum Lauren McAllister

Come all Ye Playful Cristiano Caffieri

Live and Let Diaper Lauren McAllister

Nursing a Grudge Lauren McAllister

Chateau Dietrich Lauren McAllister

Have Yourself a Naughty Little Christmas Lauren McAllister


  1. Oldgoat_MN said,

    April 19, 2016 at 5:20 am

    You are an extraordinary writer.
    Now I have to by your silly books.
    I fully expect them to be as amusing and interesting as the samples you have here.
    Thank you!

    • darrell said,

      April 20, 2016 at 5:24 pm

      Thank you so much. I have collections of my naughty short stories about to go up on Amazon.


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