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When the Secretary becomes the Boss!

Jack had been Nikki’s boss until the tables were turned!
This is my first ‘girl spanks guy’ story. The experience for writing it comes from the occasional spanking I give my boyfriend Brad, and the inspiration from a guy at my work who really could do with some of this! Nikki.

I paced the large office, my four-inch Christian Louboutin, Maudissima patent heels click-clacking on the polished floor as I retraced my steps like a caged tigress. Being the executive editor of the fashion magazine had been my dream since I began working here and I loved it but today had been difficult and I needed some relief from the stress of it all. I entered the small private cloakroom and looked in the mirror closely. Thankfully there were still no signs of crow’s feet around my eyes.

At twenty-eight I was beginning to worry about lines but my skin remained in good condition no doubt helped by lashings of expensive moisturizers. I had inherited my darker skin-tone from my mother who came from Brazil and the illusion of an even tan had been the envy of many of my friends. My father had met Mum during a business trip thirty years ago and brought her back to England, she had been working as a dancer and I owed her many of my ‘assets’. My long raven-black hair reaching to my waist had only ever been trimmed, never cut; and I also had her fabulous legs for which I would be eternally grateful!

I opened my white blouse and reached for the little bottle of ‘A Touch of Pink’ and treated myself to four or five puffs across my neck and breasts, the smell of sandalwood and jasmine mingling to make me feel sexy. My breasts were another feature from Mum. They were above ample for my petite five foot one height, measuring in with a healthy 36B cup, nicely encased in a pretty lace demi-bra from Victoria’s Secret. I buttoned up the blouse and unclasped my business skirt to tuck it in before hitching it back up just above my knees, smoothing my hands over it to remove creases and straighten the satin lining.

Strutting out purposefully I pressed the intercom. I didn't speak and it was late but knew Jack would reply, not daring to leave until I gave him permission. The building would be almost deserted by now.

''Miss Pentic?'' he inquired.

''Who else, you idiot. Get in here now!''

He didn't reply but the door opened and he entered within thirty seconds carrying a notepad.

Jack was small for a man, probably little more than five-four but he looked good in his smart suit and colorful tie, his thick curly flaxen hair and maintained stubble giving him a boyish charm. He was about the same age as me but looked younger.

I stepped out from behind my huge desk, the super high red soled stiletto heels click-clacking as I rounded it and stood in front of Jack in the center of the room. Power dressing was certainly my thing, jacket and business skirt had been tailor made in a black woolen material with a faint pinstripe, the hemline just cruising around my knees, legs shimmering in sheer black, seamed nylon stockings. With my heels I was about the same height as him but I felt taller and certainly empowered.

''You won’t need this,'' I said confiscating the notepad and discarding it on my desk. I pointed towards the ground; his eyes following my long slender nail polished fingers. ''Down on your knees,'' I ordered. My pussy tightened in excitement at the sound of my own words.

Jack obeyed without question kneeling before me. I moved in on him and pressed the front of my skirt against his face, the scent from my perfume and the smell of expensive couture exuding from me.

''Put your hands up my skirt and describe what you feel,'' I whispered.

He knew he was on probation and yet I was allowing him to explore me, to do what I knew he had drement of doing from the beginning. His hands slithered up the sides of my legs and under the hemline of my skirt into the warm, dark recess of my femininity.

''Well?'' I demanded.

''I can feel the tops of your stockings,'' he began, ''they feel smooth but lacy,'' describing my stay-ups perfectly. His fingers quivered as he slid up further. ''Your skin is soft above your stockings.'' His voice became slightly breathless, ''your panties are silky, probably satin.'' I felt his fingers smoothing over the soft material covering my well-rounded bottom then down the cleft between the top of my thighs, sliding around to the front. I didn't flinch as he explored the covered entrance to my pussy, my high heels clicking as I opened my legs a little; the pilot light of my pussy suddenly igniting inside me. Looking down on him I could see his cock leaping to attention in the front of his suit trousers hardening quickly as the heat on his fingertips intensified.

''Now tell me what color panties am I wearing,'' I husked. Each wrong guess will earn you two strokes of my cane, I added in a whisper, my pussy getting moist with the threat.

Jacks fingers trembled as he played them over the tiny patch of lace at the front, moving around again to my seat and the larger area of my panties allowing him to rub his palm across them. But what color were they?

''Black,'' he offered, no doubt assuming they would match my stockings.

''Two strokes of my cane,'' I barked triumphantly. ''Did you think I would be that predictable?''

''White,'' he guessed again without thinking.

''Four strokes of my cane, do you think I am a virgin?'' I said sarcastically.

''Pink,'' he panted rubbing his fingers along the edge of my panties, his cock without a doubt iron hard from imagining what they looked like beneath my black skirt.

''Oh dear, six strokes of my thin cane, your bottom is going to be very sore Jack,'' I giggled. This was too easy. ''I'm insulted that you would think I would wear pink, I'm going to make it eight strokes,'' I announced, my panties getting quite damp.

''That's not fair,'' Jack moaned.

''I'll decide what's fair. Getting dismissed wouldn't be any less fair, would it?''

''No, Miss Pentic'' he agreed. I was going to whip him mercilessly with my cane and there was little he could do about it other than resign, and he had already agreed to accept my punishments and stay. Besides, he had a new apartment and a large mortgage to support. (There was also the small secret he had withheld from his new boss; he had begun to enjoy it!)

''Red,'' he decided sounding desperate.

''Ten strokes,'' I said gleefully, any particular sort of red? I inquired. My nipples were straining beneath my bra and my panties had gone from damp to wet at his fumbling incompetence.

A lead at last he thought. ‘Crimson,’ he offered.

‘Twelve strokes,’ I almost shrieked. ‘You're easily fooled Jack.’ I pushed him away and his hands fell from beneath my skirt. ‘You're hopeless,’ I admonished. My manicured fingers fell to my sides and I clenched the hem of my skirt, with hips writhing from side to side I hitched it up to my waist. ‘Now tell me.’

‘Purple,’ Jack said staring at the cute tiny little panties he had played his hands over, they were a deep purple of smooth satin with a lace front panel, another favorite from Victoria’s Secret! He had at least correctly identified my sheer black nylon stay-ups high up my legs; then the show was over as I wriggled my skirt back down and smoothed it into shape.

‘Stand up,’ I commanded.

He rose to his feet before me, his smart blue pinstriped business suit wrinkled at the knees and a huge bulge at his groin as his cock continued straining against his trousers. Jack couldn't’t resist dancing his eyes all over me, first to the open neck of my blouse, my buttoned up jacket serving my breasts up towards him, then he was at my waist and skirt and then my legs. His stare fixed on my shoes, the dagger thin killer heels mesmerizing him.

I was his mistress now, in total control over him, but up to a fortnight ago it was a very different story. He had joined the firm only a few months back after having impressed an all female Board with his charming personality and his skills which looked great on paper. I was his secretary. A situation I was very unhappy with having been with the firm since my graduation and knew the business inside out. I thought I stood a very good chance of getting the editors job when it became vacant. The Board had all but offered it me and then along came Jack and snatched it away, with the added insult that I would be working for him as his secretary. A role I felt I had risen above.

Jack obviously was unaware of the behind the scenes wrangling over his appointment with some members of the board still in favor of me and he came with a cocky highhanded attitude. On his very first day he had lectured me on my place and what he expected from me and with hindsight he should have seen what was to come by the look of total anger on my face. Then as I turned for the door he had swiped his hand across my bottom, 'Be a good girl and bring me some coffee,' he hissed, the look I gave him then should have told him to watch his back. 'Revenge will be sweet’, I had thought as I scuttled out of the room, the feel of his hand on my derrière enraged me beyond anything he could have known. 'No man smacks my bottom and gets away with it,' I had seethed as I slid behind my desk.

It took over three months to extract my revenge. Three months of patience and silence as Jack’s overconfidence led him to make costly mistakes, his ineptitude continuing to evade the eye of the Board, still in awe of his charming ‘little boy’ looks. I couldn't’t believe how stupid they were and I wanted to alert them to the building disaster but then, why should I? They had appointed him and they would pay for it.

Then one day the perfect opportunity came along and when it did I acted quickly and seized the moment, leaving a paper trail from Jack’s mistakes directly to his desk. The company lost thousands and when the balloon went up there was no way he could wriggle out of it and was duly suspended pending a full inquiry. That was always going to be a foregone conclusion, even Jack knew that, painfully aware that he'd been out of his depth and completely powerless to avoid the consequences. His dismissal was inevitable and his mortgaged flat almost certainly lost when he was called back to face the Board.

At first he seemed surprised that I was in the room to hear his disciplinary findings. I sat passively in a dark business suit; my long legs crossed and brightly polished fingers in my lap, my short skirt giving him a flash of stocking top as he waited for the inevitable. The Board was itself smarting over the obvious lack of management and Sarah Johnson the director responsible for hiring him and the main player in preventing me getting the job, was busy clearing her desk. The blond witch whom everyone walked in fear of had shed tears like a freshly spanked girl as the rest of the Board dismissed her without hesitation, eager to distance themselves from the mess Jack had caused.

‘Your actions were unacceptable for someone in such a high managerial position,’ the Chairwoman was saying. ‘Therefore appropriate steps have been taken to replace you with immediate effect. As you are still on probation we are not obliged to give you anything other than your normal notice period which will begin as of now.’

'So that was it,' he thought; out of the door and unemployed, possibly even unemployable. He cast a glimpse towards me wearing a satisfied smile.

‘However,’ the Chairwoman continued. ‘Your replacement has requested a secretary and we are able to offer you that role. This will mean a large demotion and reduction in salary but the choice is there.’

Jack was suddenly brought back to life, his mind in a whirl and not even thinking about the long-term situation. It was a job; and he desperately needed that! ‘Thank you Madam,’ he said deferentially. The other members of the Board, all female, looked embarrassed by his pathetic toadying.

The Chairwoman looked over her spectacles at him. ‘I have to say that we as a Board took some convincing by the new manager that you were worth keeping. Since the Board have accepted some responsibility in taking you on we feel you should have this option but you owe this opportunity entirely to her, young man. Let me be understood, if she so wishes you will be dismissed without any further inquiry?’

‘Yes Madam,’ Jack uttered quickly. ‘Thank you Madam. I won't let you down.’

‘We'll see about that,’ she remarked dismissively. ‘Your personal belongings have been removed from your old office and placed in the outer office. Miss Pentic will be your new manager and you will take your directions from her in the future. Understood?’

‘Yes Madam,’ he stammered, still reeling from her last words. Miss Pentic, Nikki! She was his new manager!

We had officially swapped jobs and I spoke for the first time. ‘Wait for me in my office,’ I barked.

Jack turned on his heel and left.

Unknown to the rest of them in that room, I had almost climaxed watching Jack squirming in front of his female superiors, a lone man with nowhere to go except to my office to await whatever fate I decided for him. Even as the Chairwoman was speaking I had already decided what that fate would be and my panties were damp in anticipation. It was late, well past the time when the office staff had left and the executives would soon leave the building, leaving me and Jack together, alone in MY office, with him at my beck and call!

I had dreamed of this moment for a long time; he would regret having given me that silly slap on my bottom!

When I finally entered the office, Jack was standing in the middle of it, casting his gaze around what was his office up until a few days ago. He didn't know whether to be angry or contrite. ‘You really stitched me up,’ he hissed as I entered.

‘I don't know what you're suggesting,’ I said squaring up to him. ‘You weren't up to the job. Simple!’ I stepped up closer, ‘You heard the Chairwoman. One word from me and you are out of the door. You will do as I tell you but if you can’t agree to that then you are free to leave, is that understood?’

Jack knew he was defeated. ‘Yes, Nikki,’ he said resignedly.

‘Miss Pentic,’ I reminded him. ‘You will address me as Miss Pentic at all times.’ I brushed past him and sat behind the large desk. ‘Come here,’ I ordered pointing at the space by my side.

Jack rounded the desk and stood where I had indicated.

‘How much do you want to keep your job, Jack?’ I said playfully, pushing back my chair and crossing my legs provocatively. My underskirt rustled against my stockings and I was having fun, my pussy tingled.

‘You know I need it, Nik… Miss Pentic,’ he answered dutifully.

‘Enough to take down your trousers and bend over my knee?’ I said looking directly at him.

Jack wasn't sure if he had heard me correctly. ‘What … What did you say?’

‘Either you go over my knee right now or you're finished here.’

His mouth gaped open. He looked hard at me and he could see I was deadly serious, he glanced into my lap, knee raised over the other one, a stiletto confidently balanced on the end of my toes, the other firmly planted on the floor.

‘Come on. I haven't got all night. Take down your trousers and pants and get over my knee.’ I said raising my voice. Sliding open the drawer in front of me I pulled out a flat-backed hairbrush. ‘This should establish who the boss is now,’ I said, my long slender fingers encircling its handle before smacking it against my other open palm.

‘You’re serious about this aren’t you?’ he said finally getting the message.

‘Of course,’ I said engaging his eyes with mine. ‘But obviously you are free to leave if you wish.’ I slapped the hairbrush against my palm again to illustrate what he would be signing up to. ‘The choice is yours, Jack.’

‘If I accept will I get to keep my job?’

‘Even if you don’t accept you will keep your job, Jack. I’m not that much of a bitch. Let’s just say I would appreciate it if you would play along, role-play if you like.’

‘I could think of worse things than going over your knee Miss Pentic,’ Jack said with a wry smile. His fingers played with the buckle on his belt and unleashed it, unzipping his flies before letting the trousers of his best suit fall to his knees.

I was amazed at how readily he had risen to my suggestion. I studied the huge bulge in the front of his shorts. ‘Take them down,’ I mused.

Jack surrendered and dug his fingers into the waistband of his underpants and pulled them down over his manhood to the middle of his thighs. His cock was semi hard and hung inertly between his legs but I was impressed by its great length even in its current state.

Satisfied with his cooperation I gently tapped my knee. ‘Bend over.’

Jack bent forward and steadied himself on my thigh which was surprisingly solid beneath his weight and lowered his body over my knee and reached to the floor, his bared bottom stared up at me as both his trousers and underpants slid almost to his ankles.

I was taken aback by how tight and small and white his bottom was I hadn’t known what to expect not having had a man over my knee before. I put an arm around his waist and tapped the cold wooden back of the hairbrush against his bottom before swinging it high and delivering it on his left cheek. Jack moaned lightly but didn't’t react so I gave him another, then two more and soon he was bucking against the rough material of my skirt. I unleashed the strength in my arms and spanked him rapidly several times.

I stopped briefly to pull up the sleeve of my blouse before beginning another tirade, the harsh sound of my hairbrush echoing around the office as it bounced quickly from cheek to cheek and back again. Jack’s legs were kicking up as the heat in his backside soared and turned crimson; my crossed knee beneath him was rock steady and my aim perfect as I spanked him with a ferocity he could never have imagined.

‘Get up,’ I said at last and Jack heaved himself up using my legs and thigh to get off, pushing my skirt up over my stocking tops.

Both his hands were employed urgently behind him to requite the flames I had lit in his bottom and he failed to notice me eying up his cock, now erect and lunging towards me.

When he did notice he tried to cover himself but received a smack on the hand from the hairbrush. ‘Hands behind your back,’ I demanded continuing to admire his erection. ‘Seems to me you actually enjoyed me spanking you,’ I husked. His face told me he had without saying a word or even giving a nod. Reaching into my desk drawer I retrieved a small packet, which he recognized as a condom, and popped it from its wrapper and in one move slid it over his massive cock.

Jack could only stand mesmerized as my long fingers encircled his shaft and massaged him back and forth his eyes taking in my stockings and bare milky white thighs. I pulled my skirt up further still until my panties came into view then he jerked wildly and filled the teat in the condom.

I stopped massaging him immediately. ‘Pull up your pants,’ then sarcastically. ‘Be a good boy and fetch me a coffee,’ and waved him away.


The click-clack of my stiletto heels brought me back from my reminiscences of his fall from power and that first over-the-knee spanking I had given him. A spanking that had blistered his backside and brought countless smirks from me as I witnessed him gingerly sitting in the new, hard chair I had arranged for him. I crossed the hardwood floor of the office to the cupboard from which I produced a long thin whip cane and promptly swished it through the air.

Spinning on my ultra high heels to face him I bent the cane into an arc between my slender fingers. I licked my lips, they were moist and pouting in bright red lipstick and if he could have seen through my buttoned jacket my nipples were erect and hard. Beneath my skirt my pussy was dampening my panties with the thought of what I was about to do to him.

‘When will men learn that we are not only the fairer sex, we're also the smartest; a lesson you will learn by the time I'm finished with you.’ I whispered. ‘Now take down your trousers and bend over my desk.’

Jack eyed the cane nervously. I had caned him once before but only six strokes and then on the seat of his trousers. He had enjoyed that, his cock told me he had, I had stroked him off afterwards and he had cum in seconds.

‘Bare yourself and present your bottom to me,’ I husked. ‘Call yourself a man! Twelve strokes for not guessing the color of my panties,’ I laughed loudly. ‘I thought a man could guess the color of a woman's panties just by looking at her.’

Jack’s fingers trembled as he unbuckled his belt and dropped his trousers to his knees, my look told him his shorts were to follow and he quickly pulled them down; almost embarrassed at the huge erection he sported.

‘Well hello big boy,’ I cooed. ‘I guess you will need some hand relief after I've whipped you. Bend over.’ His hard on jerked at my remark then shuffled up to what was once his desk and bent forward, his cock jammed firmly between it and his stomach, cold and hard to the touch.

My Louboutin heels click-clacked as I took my position behind him and moments later a stripe of pure heat followed a whistling sound as the cane snaked across both his cheeks. He let out a yelp, which he stifled as the next stroke arrived almost in the same groove. I wasted no time in swishing the cane back and whipping it across his bared backside, the power of my strokes belying the strength concealed within my feminine curves. Jack was howling like a baby as stroke after stroke creased his seat until he jumped up from the desk and pummeled his rear end in search of some antidote to the heat I had planted there.

‘Did I give you permission to get up?’

‘No Miss,’ he said bending back into position quickly.

‘Four more strokes to go,’ I informed him, ‘and then something extra for your disobedience.’

My heels clicked again, the cane cutting across his proffered cheeks like a sword, then again, his bottom at melting point when another and then the last stroke cut him down to size. He was whimpering like a baby when I finally allowed him to stand.

I placed the cane on the desk and sat on its corner, one foot firmly on the ground the other hooked onto its protective rail about eighteen inches from the floor, my spiked heel locking my foot onto it providing a convenient platform. ‘Bend over my knee,’ I beckoned. ‘I'll teach you not to get up before I tell you to.’ I patted my skirt and he shuffled over to me and bent over it.

At first the flat of my open hand seemed insignificant in comparison with the cane but the swiftness of my spanks soon made an impact on his already hot bottom. Jack gyrated wildly on my knee, his erection trapped between my skirt and his stomach, each smack of my hand thrusting him forward. His head was suspended just above the floor with a birds-eye view of my legs inches from his face, my sheer black nylons hugging every curve as they descended into my stilettos.

His cock jerked beneath him from the massaging effect of my spanking him, the heat in his rear end and no doubt the sight of my legs. My perfume and warm female essence mingled in my nostrils together with my power over him and I climaxed in my panties; I felt Jack as he came yet again, his liquid pumping into the tiny void between him and my skirt.

His face was almost as red as his behind as I released him and allowed him to scramble off my knee, leaving his cum smeared across the front of my business skirt.

‘You naughty boy,’ I said huskily. ‘You need your bottom spanking more often; I hope you have saved some for later!’

Jack spluttered with both embarrassment and in amazement at how turned on he had become by my dominance over him. ‘I… I'm sorry Miss Pentic,’ he groveled. ‘Would you like me to clean it for you?’

‘You will be sorry Jack. I can promise you that,’ I breathed sexily standing up from the desk. I unbuttoned my tailored jacket and slipped it from my shoulders, hanging it across the back of the padded leather chair. ‘You can take my skirt to the cleaners later.’

Jack's eyes fixed on my very ample breasts bursting for release against the white blouse, nipples hard and obviously erect. My long manicured fingers played with the wide belt lashed tightly around my waist and I quickly unleashed its buckle sliding it from the loops of my skirt. His eyes followed my every move as I folded the thick leather, his hands instinctively returning to his still throbbing backside. ‘Don’t worry Jack,’ I smiled. ‘Maybe next time I’ll use it across you.’ His cock suddenly stiffened at the prospect and appeared to nod its agreement!

I fingered the waist button and zip of the tight pinstriped skirt and it slumped from my middle and slid to the floor, stepping out of it I placed the soiled skirt flat on the desk.

I stood before him with my legs slightly apart, hands on hips and his eyes bulged at the sight of my figure. My mother had been a professional dancer and I had inherited her legs and I knew they looked good in stockings and high-heels, my sex throbbed between them.

‘Come here!’ I ordered pointing to the spot in front of me; he shuffled over still with his trousers and pants around his ankles. ‘Down on your knees, Jack.’ He obeyed instantly. ‘Now take down my panties.’

Jack’s fingers fumbled around the waistband then drew them down over my stocking tops letting them swish down my nylons to my feet. His face was directly in line with my pussy ‘vee’ and I put my hand on the back of his head and drew him to the little ‘runway strip’ of dark fur. He licked it obediently.

Sitting back into my chair I spread my legs and signaled for him to continue. As my boss, Jack had a very sharp tongue, now it was being put to a better use! I grabbed his soft curly hair as he licked against my pussy lips, darting in and out, tempting my sex, finding my clit and encircling my little sex button with his wet tongue. I arched my back as he entered me, snaking around my shallow depths as far as his mouth muscle would allow then I came again!

I stood up and he followed, directing him to face my desk. His cock was an angry purple and I wrapped my hand around it and massaged him gently using my other hand to cup his ball sac now fully recharged. I felt him tremble then shake as his cream left his balls like magma from its chamber, surging through the volcano of his cock and erupting across almost the full length of my skirt. The jerks came urgently as he expelled his pent up man-juice, streaking the black material like some modernist painting.


The security guard in the office foyer eyed me suspiciously as I click-clacked across the mezzanine towards the doors, dressed in a short raincoat on a warm dry summers evening! Little did he know I was naked beneath it from my waist down.

Thankfully the taxi pulled up as I left the building and I jumped into the front seat and told the guy my address. I was horny and regretting not allowing Jack to fuck me. The driver was a black guy about thirty and built like a weightlifter his big eyes surveying my strange evening wear.

‘Would you like to come up for a coffee,’ I asked as we pulled in front of my apartment block.

‘Don’t drink coffee,’ he said dismissively.

‘How about ten minutes for a fuck!’ I offered.

‘You serious lady?’ He flashed a row of spotless white teeth.

I opened my raincoat and his large eyes popped forward; within thirty seconds he was opening my door like the perfect gentleman.

I could feel the heat from his eyes as he followed me up the one flight of stairs, the seams of my stockings attracting him like a puppy, no doubt craning his neck to see the lacy tops as I ascended the steps. I unlocked my door and without any ceremony swept the raincoat from my shoulders and stood before him in my kitchen in just stockings, heels and my lacy bra. I reached behind me and unhooked the bra and discarded it, my breasts dancing with the movement and leaned backwards over my table. I spread my legs inviting him in and heard the fall of his zip as he approached me, grabbing my ankles and hoisting them up over his broad shoulders.

‘Aaaahhh!’ I sort of semi shrieked and cooed as his throbbing cock entered me without any preamble, no nuzzling or fumbling, straight in; impaling me to its hilt. His shaft felt good and hard and so thick I didn't’t have the muscles in my tunnel to tighten on him any harder than he already was. His massive hands were gripping my legs wrinkling my stockings as his buttocks drove him back and forth into me, my boobs jiggled in tune, nipples wobbling as if on jelly. I had not’t had sight of his cock as he entered me but I knew it was big and he knew how to use it!

I groaned and then he groaned and being a gentleman he eased himself from me and shot his hot liquid across my midriff. His cock went limp and I saw it for the first time as I reared up from the table, he tucked his huge member into his pants and zipped up.

‘I make that a round twenty,’ he said matter-of-factly.

‘What?’ I said stupidly, still getting off the table, my high heels struggling to get a purchase on the floor.

‘For the ride,’ he explained, ‘twenty, for the taxi.’

I paid him and he left. Shouldn't’t that be the other way round? I swore to myself for not getting his name. A satisfying cock for the price of a taxi ride seemed really good value!

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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