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Bossy Boots

By: FootjobLover



My heart thudded ominously when I read the subject line of the email:

"Re: Misuse of company internet. EVERYONE READ!"

Shit, I thought to myself. This isn't the way I want my Monday to start, with an anxiety attack.

Perhaps this just a bizarre coincidence, I tried to reassure myself. I attempted to muster the courage to read the content of the email.

Did senior management know that I had been frequently surfing porn websites while I was in the office, I asked myself. Not only had I been visiting the sites, but I had been masturbating to the images while I was sitting at my desk.

I wasn't proud of that. Not in the slightest. Playing with myself at my place of work, for fuck's sake!? How did I end up like this? I could only comprehend with dread the kind of zero tolerance corporate disciplinary action I was condemning myself to when, not if, I got caught.

To make my situation worse, wallowing in the particular caliber of internet filth that I craved was most definitely out of the question at home. My wife's abhorrence of anything remotely resembling pornography, coupled with her disturbing and uncanny aptitude for stealth - suddenly appearing in the room and catching me off-guard at any given moment - would quite probably bring down some kind of unnecessary psychotherapy or sex-addiction counselling on me, if not an outright divorce.

My habit was getting worse too. It was spiralling. I found myself looking at hardcore sites whenever I had the ground-floor office to myself, even for just a few minutes.

I'm probably just being overly paranoid, but I'm pretty sure Jill caught me last Thursday. I share an office with her and two other guys; Peter the desktop support manager and Don the senior telecoms technician. 

I had started at 8am with the genuine intention of completing my weekly server maintenance routine before I started prioritising the various company work orders which had been assigned to me on our online system.

I'd had the room to myself. Peter usually starts at 8am, but hadn't arrived yet. Jill doesn't normally arrive until 8.45am, and Don was away, visiting another of our sites on this particular occasion.

My desk is situated at the top right corner of the room, so anyone opening the door to the office can quite clearly see the display on my PC monitor at any time.

Like I said, I hadn't really intended to look at porn on the morning in question. I'm in the habit of firmly closing the secure keypad-entry door behind me at night when I leave and, for some reason, I likewise closed it behind me that morning too before I sat down at my desk. As soon as the lock clicked into place, I realised the opportunity I had inadvertently created.

Working in I.T. has advantages which aren't necessarily available to other sectors of the business; unlimited internet access being, by far, my favourite.

I unlocked my screen by typing my password and opened my web browser. 

Just ten minutes, I thought to myself, my heartbeat already elevated with excitement. I'll get it out of my system for the day so I can focus on work.

I typed the address: www.xxxhotthumbs.com and hit return.

Momentarily, my screen was redecorated with thrilling and explicit hardcore sex thumbnails, each one an example of whichever particular enthralling niche it represented.

I scanned over the many tantalising genre galleries available; MILF, Pornstars, Big Cocks, Female Ejaculation, Toys, Cumshots... 

I was already getting hard as I scrolled down the available galleries.

'Morning, Andrew!' a female voice from behind me suddenly said. The urgency with which I minimised my internet browser could not have failed to give away the fact that I was looking at something deeply inappropriate for the workplace.

It was Jill. She had also arrived into work early, quietly pass-coding her way into the room while I was hypnotised by the many possible pornography sub-genres a mere mouse-click away.

'H..Hi, Jill!' I stammered in response to her silent and unexpected arrival.

I realised I was sweating. In the next few moments, I tried to figure out if she was suddenly acting weird around me. I was almost certain I had been caught. Did she have an embarrassed or offended blush on her face, I asked myself. I glanced around at her once more just as she was removing her coat. She quietly sat down at her desk, which is back to back with mine.

The next few hours were excruciating. I was convinced Jill wasn't talking to me as much as usual, although, I reassured myself again and again, it was probably just my paranoia.

At 5pm, I figured I'd dodged a bullet, as I didn't appear to be fired and hadn't been escorted from the building by vice officers. Friday, too, passed without incident, and I enjoyed a relatively guilt and porn-free weekend.

This email, however, gave me the fear. I took a deep breath and started reading.

"Management would like to take this opportunity to remind all members of staff that misuse of company internet, including emails, will not be tolerated and may result in instant dismissal for gross misconduct...".

Fuck.

Before I could further terrorise myself by reading on, my desk phone rang.

'Andrew?' a woman's voice said. 'It's Isobel. Sylvia wants to see you in her office immediately.'

Isobel is Sylvia's personal assistant. Sylvia is the company director.

My heart slammed in my chest. 'Thank you,' I replied, my throat dry.

Fuck.

I stood up, walked past Jill as she sat at her machine, and left the room. I ascended the wide staircase leading up to the first floor of the building and Sylvia's office. 

Isobel, whose desk is right outside Sylvia's door, saw me approaching. She raised a disapproving eyebrow at me as she stood up to knock her boss's door, informing her that I was here.

My mind raced. Was this about the porn, I wondered, panicking slightly. Or something completely innocent?! Would I accidentally incriminate myself by acting so guilty?!

Isobel held Sylvia's door open for me as I entered her office.

'Andrew,' the attractive female director said dryly. 'Sit down, please.'

I did as instructed, sitting opposite at her lavish desk. I heard Isobel closing the door behind me.

'I have recently been made aware of an extremely serious matter concerning you and,' she paused, inhaling gravely, 'I'm afraid, I have no choice but to fire you for it.'

My stomach leapt up into my throat. 

'What...?!' I said, struggling to accept her words. 'No, please! Wait... Fire me? For what?'

Sylvia opened a leather-bound A4 notebook in front of her. There was a single printed sheet just inside the front cover.

'I have here a comprehensive list of every website you've visited for the last ninety days,' she said, glancing up and down the loose sheet. 'Each one of these sites has been electronically stamped with your workstation I.P. address, meaning they were all visited by you.'

My heart felt like it was being dragged down into quicksand.

'Do you want me to read some of these out?'

Before I could reply with an ashamed 'no', Sylvia started reading from the sheet.

'Hardcore double penetration deep dicking,' she read, lifting the page up off the notebook. A tiny part of me wanted to laugh when she read that out, which was incredible under the circumstances. She continued to read out the filth website descriptions.

'Pussy on pussy all-girl dildo orgy gallery'... Let's see...Oh yes, 'Barefeet on big cocks footfucking cum eruptions...'

She finally looked up at me.

'Do you have any idea how much trouble you're in?' she asked.

Flashes of my immediate future - futilely attempting to explain to my disgusted wife the reasons for my dismissal as she packed her bags to leave me - raced through my mind. I just couldn't face that.

'Please, Sylvia,' I said, my voice sounding pathetic as I begged for some kind of leniency. 'Please don't fire me. Please give me another chance. It was a mistake...'

The ridiculousness of the last sentence as it left my mouth made me cringe inwardly.

Sylvia sat, quietly reading the remainder of the print-out and shaking her head. After what felt like half an hour, her eyes reached the bottom of the page.

'You know,' she said, looking at me and sighing. 'I ought to call the police right now, Andrew.'

I felt like crying.

'You're married, aren't you?' she asked.

'Yes,' I replied, looking down at the floor in shame.

'Your wife,' she continued, 'does she know you're into all this perverted internet sex too?'

'No,' I replied. 'She detests it.'

'I see,' she said, replacing the sheet again on the opened notebook page.

'I'm also married, Andrew,' she said, 'and I know how difficult it can be when one of you has different.. how shall I say this... requirements... from the other.'

I looked up from the spot on the floor on which I'd been focussing my despair.

'You see, my husband has a somewhat limited sexual repertoire,' she remarked, sitting back in her leather swivel chair.

For a moment, I wasn't sure I had heard her correctly.

'Your husband..?' I said, confused.

'My husband...' she continued, but tailed off, evidently reconsidering her next words.

'I'm curious,' she said, 'have you also been masturbating to these porn sites while you've been in the office?'

My shame could hardly have been any greater at that moment. I offered a brief nod instead of a spoken response.

'I see,' she said, looking at me intently.

Then, something happened. The expression on her face seemed to change. I noticed she seemed to be breathing more heavily too.

I watched as a wicked half-smile slowly came to life on her red-lipsticked mouth.

'I bet the carpet under your desk is all stained with your sticky cum now, hmm?' she said.

'I'm sorry?' I replied. My head seemed to be spinning. Did she really just ask me about my cum?!

'You heard me,' she said, reading the look on my face. She tutted. 'Stroking your cock while you're supposed to be working.'

I was at a loss. Sylvia sat forward, clasping her hands on the desk.

'I'm going to offer you a deal which will help both of us out of this situation,' she said calmly. 'But you'll have to accept it before I give you the details. Those are my terms.'

'A deal?' I replied. 'What sort of a deal?'

'Let's just say for now that if you turn it down, I'm calling the police and your contract of employment here will be terminated, effective immediately.'

So far not a great option, I thought to myself. I would be a complete idiot to refuse any opportunity to avoid being sacked, losing my career, my wife, and my future. What had I to lose besides everything?

'So?' Sylvia probed. 'What's it to be?'

I exhaled, vainly attempting to calm my jangling nerves.

'Yes,' I said, 'yes, I would like to make a deal.'

The wicked grin swelled again on her lips.

'Good answer,' she said, sitting back in her seat. 'Now, do you want to hear the deal I have in mind which just might save you from unemployment and a shame-filled divorce from your poor wife?'

I nodded. 

'Good,' Sylvia said. 'In that case, take off your clothes.'

I froze. Did she just tell me to...

'I said take off your clothes,' she repeated sternly. 'Do not make me ask you again, Andrew, or the deal is null and void, understand?'

What could I do?! 

I slowly stood up. My hands were trembling as I pulled my tie undone and started unbuttoning my white shirt. Sylvia scrutinised my every movement as I pulled my shirt from the waistband of my dark grey suit trousers and dropped it to the floor.

I looked at her. Sensing the impatience in her stare, and not wanting to jeopardise this so-called 'deal', I unfastened my brown leather belt and undid the clasp of my trousers, unzipping my fly. I dropped my trousers to my ankles, revealing my red cotton underwear.

She was now studying my thighs and crotch. I kicked off my slip-on black leather shoes.

'Socks,' she said, demandingly. I stooped to remove each black cotton sock, leaving me barefoot on her office carpet, surrounded by my discarded work clothes.

'Underwear too,' she said, gesturing at my shorts.

I hesitated for a moment, however this was difficult to do given my detestable lack of options. I was indeed the proverbial cornered rat.

I slipped my thumbs inside the elastic waistband of my underwear and reluctantly pulled them down. I kicked the shorts off my ankles.

Sylvia didn't speak a word. She inspected every naked inch of me from my neck to my nipples, down my biceps and forearms to my waist and, of course, to my exposed genitals.

'Very good,' she finally said. 'I can see that you exercise a lot, don't you?'

'Yes,' I replied nervously.

'You like to take care of your body', she continued. 'It's refreshing to see a man such as yourself with his business attire removed, displaying his naked body in what is usually his place of work.'

I watched her as she eagerly studied my cock. She seemed to be examining every vein and contour from across the desk where she sat.

'Demonstrate your wanking technique for me,' Sylvia ordered. 'How do you pleasure that dick of yours while you're enjoying this...' she glanced again at the sheet of paper, '...bare feet on big cocks footfucking cum eruptions site.'

I shuffled nervously on the spot. Doing as she instructed, I wrapped my hand around my flaccid cock and started to stroke myself while she watched.

'That's it,' she directed, 'get it nice and hard. Let's see that foreskin rolling back.'

I continued to jerk myself for the boss, pulling back my foreskin and exposing my hardening glans. I looked up as I played with myself, and noticed her eyes locked on my stiffening prick.

She had a look which suggested she might devour me before the day was over.

'Come closer,' Sylvia suddenly demanded. 'Stand there.'

She pointed to a spot on the floor on her side of the desk directly in front of her seat. I went and stood exactly where she had indicated.

'Closer to me,' she directed. I stepped forward, standing right in front of her.

She looked up and down my bare legs and feet, studying my toes, then gazed straight at my erect penis.

'You know, Andrew,' she said, 'I absolutely adore sex. My husband doesn't fuck the way I want to be fucked.'

I looked down at her, still staring at my dick. I found myself longing for her to touch me.

'Besides using my dildo,' Sylvia continued, 'I haven't had a beautiful, big, hard cock inside me for almost a year. Wouldn't you say that was unacceptable?'

I imagined her using a dildo on herself while hubby was away golfing, bringing herself to a juddering, wet climax on her marital bed. Despite the conflict of my mostly happily married home life with Alison, I suddenly found myself wanting to fuck this athletic, mature, sex-starved, professional brunette right then and there in her office. 

Sylvia began to slowly pull up her smart, black skirt. I looked down at the black high-heeled, calf-length leather boots she wore on her feet. My cock throbbed with lust at the sight of the sleek, silk stockings which tightly caressed her long legs, followed by the sexy black suspenders at the top of her beautiful thighs.

She slid herself further down her director's chair as she pulled her black skirt all the way up to reveal her lack of underwear.

What a beautiful pussy Sylvia has! She was shaved with the exception of a single exclamation mark of dark brown hair just north of her pink lips. She spread those silky thighs of hers as wide as she could, granting me full access to that sexy, married pussy.

'Get on your knees,' she ordered. I knelt down as instructed between her smooth, stockinged thighs. I inhaled the aroma of her glistening sex as it mingled with the warm scent of the leather from her kinky stiletto boots. 

'Now,' she said, 'time for you to fulfil the first part of our deal.'

My erect cock seemed to be doing the thinking for me, but I tried to focus on what Sylvia was about to say.

'If you can make me come, first with your tongue then with your cock,' she explained, 'and both times had better be good...!' I swallowed hard, listening.

'...I won't call the police and you'll be one step closer to keeping your job.'

'You want me to...?' I started.

'That's right,' she interrupted. 'Eat my pussy. Make me come hard!'

I had gone down on Alison on a handful of occasions, but, for whatever reason, she had never been able to relax enough to climax.

I began to lower my face between her thighs.

'Wait!,' Sylvia said, 'put your tie back on.'

I looked up at her.

'My tie?' I said, puzzled.

There was that look again; the one where you don't want to make her repeat herself.

I reached over and grabbed my silk tie from among the pile of my discarded office wear. Sylvia watched intently as I carefully replaced it around my bare neck in a neat Windsor knot, sliding it into place underneath my chin.

'Mmm,' she purred, clearly more aroused by the presence of the tie, 'that's much smarter.'

She tapped a single button on her desk phone. I recognised Isobel's voice on the other end.

'Yes, Sylvia?' the P.A. said.

'Please make sure I'm not disturbed for the next hour,' Sylvia spoke into the hands-free receiver on her phone. 'I'm in the middle of disciplinary proceedings.'

'Of course, Sylvia.' Isobel replied.

Sylvia grinned at me as she lay back in her seat.

'Now,' she said softly, 'lick my pussy. Kiss it like you're kissing your wife's lips on your wedding day.'

Again I felt that painful pang of guilt as I thought about kissing Alison when I arrived home this afternoon. 

I had to do what was required of me to make amends for my porn indiscretions.

On my knees, I leaned forward. Sylvia's hands were either side of my head, her fingers ruffling my hair as she pulled me down between her thighs. My nose sank into that sculpted, dark bush of hers as I inhaled the rich, musky aroma of her pussy.

She sighed with pleasure, tightly holding my head in place.

'Isn't that the most beautiful cunt you've ever seen, Andrew?' she asked, tightening her grip on my head.

I tried to answer, but found myself unable to.

I opened my mouth. My tongue encircled and flicked the hood of her engorged clit. I sucked it into my mouth, grinding my lips against hers as she moaned in approval above me. 

'Oh.. Fuck, that's it!' she sighed with delight, those leather boots now in the air either side of me. 

I traced out a steady and consistent figure-of-eight pattern against her saliva-drenched clit, tonguing it firmly and decisively with each upward and downward stroke. She writhed on the seat as I slipped my tongue inside her, momentarily breaking from the steady pulsing and kneading of her sweet clitoris. I noticed her hips bucked the most and she inhaled more sharply when I flicked her excited little pink bud in a downwards diagonal fashion.

'Mmm...' she sighed, squirming with pleasure, 'you like the taste of that fucking wet pussy in your mouth, hmm?'

I chose to answer by concentrating the diagonal approach even more acutely on what I felt was the sweetest part of her sweet spot.

'Fuuuuck!' she moaned, now holding the back of my head in place with one hand. Her other, I noted, was now above her head, gripping onto the headrest of her leather seat.

I licked and flicked and sucked that beautiful fleshy nub like my job depended on it.

'Fuck yes! Fuck yes! Fuck yes!...' she swore, grinding herself rhythmically against my cramped, aching tongue. 'I'm going to.... Oh, my fucking...!.... Mmmm....I'm going to come...!'

Sylvia clamped her stockinged thighs tightly around my neck as she began to orgasm. The sharp heels of her leather boots dug into my bare back while she did her utmost to stifle her loud yelps of satisfaction. I drew her volatile clit into my mouth and sucked for all I was worth.


Bossy Boots



I was scarcely able to breathe during the peak of her climax; her thighs like an airtight vice around my neck. 

Finally, her grip loosened as she sat panting, her eyes closed. My face was drenched with her juices, as was the dark green leather of her swivel chair.

'Oh my...!' she said finally, looking down at me as she slowly uncrossed her legs from around my neck. 'You made my pussy squirt, Andrew!'

My entire being seemed to be permeated with the taste of her. I knew there was no way that Alison wouldn't smell another woman's pussy on me when I arrived home tonight.

Sylvia sat forward, her legs still spread wide either side of me.

'Is that cock still hard?' she asked, looking down to see.

I leaned back slightly to show her the erection between my legs.

She touched herself with her right hand, slipping two fingers inside her drenched, glistening pussy. She slid them noisily in and out, sighing, for several beautiful moments. She withdrew her fingers and leaned forward to me, wrapping the same hand around the shaft of my hard dick.

I watched as she smeared her juices back and forth along my veiny, hard cock. Her touch was gentle but firm as she stroked me from my balls to the tip of my glans, the underside of which she firmly and adeptly kneaded with her thumb.

'Such a beautiful, hard dick,' she purred, making a tight ring at the base of my swollen glans with her fist.

'Fuck my hand,' she commanded. 'Fuck it slowly, but DO NOT come until I tell you, understand?'

I nodded, my breathing fast and excited as I slowly thrust my erect cock back and forth into her lubricated hand.

'Mmm,' she purred. 'Does your wife like to do this to your hard cock?'

Alison was strictly a missionary position girl, and not incredibly enthusiastic about experimenting with new methods of intimacy.

I nodded, watching her wet thumb glide back and forth with each slow thrust of my painfully erect penis.

'Liar!' she said, squeezing hard then releasing, making me gasp.

'I bet she doesn't even suck this cock anymore,' Sylvia continued. 'Am I right?'

I nodded, this time telling the truth.

Sylvia leaned further forward, pursed her lips and spat on the fat glans of my penis. She smeared her warm spit all the way down to the base of my dick and all around its girth, further lubricating her hand as she continued to wank me.

'Does she like being fucked by this hard cock?' she asked. Her filthy questions were seriously testing my self control. I desperately wanted to come.

I nodded.

'Really?' she probed. 'Does she have a nice, tight cunt like mine?'

I shook my head.

Sylvia laughed. 'How about her asshole then?' she continued. 'Does she let you fuck her in the arse?'

I had to stop thrusting for a moment as I felt my cum surge towards my urethra.

'I DIDN'T TELL YOU TO STOP!!' Sylvia chided angrily.

I slowly resumed fucking her warm, wet hand.

'From your response,' she continued, her tone settling again, 'I'd say that no, your wife doesn't let you fuck her arse, but you'd very much like to do that to her, am I correct?'

I nodded, trying desperately to pace the thrusting of my cock into her teasing, squeezing, stroking hand.

'I'd love to feel a man's cock in my asshole,' she said. 'That's also something my husband has no interest in, despite my many requests.'

I glanced down, reveling in the sight of the tight, pink orifice just beneath her pussy.

'Get closer,' she ordered, 'I want to feel the heat from your cock against my arse.'

Obediently, I shuffled even closer to her on my knees, her hand firmly around my swollen dick as she pulled me towards her. She lifted my cock, tightly pressing the tip of my glans against her arsehole as she continued to stroke me.

She moaned, delighting in the warm, moist sensation against her unexplored anus. 

'Oh, that feels so good!' she said, sighing. I couldn't remember a time when my dick had been as unbearably hard as it was at that moment.

Sylvia reached out her free hand and grabbed my tie, pulling me even closer still.

I felt the tip of my cock suddenly penetrate her tight asshole. She yelped as my rock-hard glans suddenly slid up inside her.

'Oh FUCK..!' she swore, loudly. She was practically choking me with my tie as she pulled it, inching me further and further inside her tight arse.

'Mmm..' she sighed, her hips bucking back and forth. 'Your cock is inside me! Oh, your fat fucking cock is in my ass!' I started to slowly fuck Sylvia's asshole; sliding my hard dick back and forth to the sound of her delighted yelps. I started to find it impossible not to come. I could feel the first trickles of my semen escaping into her ass as I slowly inserted and withdrew my cock.

She was frantically masturbating with her free hand, grinding and stroking her well-sucked clit as I fucked her on my knees.

'Aaaaahhh!!' she suddenly moaned. 'Mmmm... Fucking coming...!'

Sylvia started to orgasm for the second time. Her hand went into overdrive against her pussy as she again climaxed, this time with my hard cock deep in her tight arse. 

That was it for me. My dick went into meltdown and I finally lost control.

Sylvia suddenly pulled me from her arsehole. She must have felt the spasms of my prick as I started to come inside of her.

She brought her left leg higher and aimed the tip of my cock midway up her leather boot, fiercely wanking the first spurts of my cum all over her footwear.

I moaned with abject delight while my sperm rained down onto my employer's beautiful high-heeled leather boot. There were great wet splodges on her black stockings where it had splashed messily.

Sylvia grinned above me, expertly milking each and every drop of my cum onto her leather boot.

'My, my, my!' she exclaimed. 'That's a lot of spunk, don't you think?'

I gasped and nodded, still kneeling before her.

'Fetch your shirt,' she said sternly, letting my spent cock flop from her hand.

I shuffled over to the pile of my clothes and grabbed my crumpled shirt as commanded.

She extended the cum-smeared leather boot so that its spiked heel dug into my chest painfully.

'Clean it,' she commanded. 'High gloss sheen, nothing less.'

Aw fuck, I thought. Not only do I stink of pussy but my shirt will be stained with my own cum!

Reluctantly, I wrapped my cotton shirt around her boot halfway up her calf. I wiped each droplet of my sperm from the leather, removing each white rivulet as I buffed as hard as I could.

'That's it,' she said, watching. 'Break a sweat!'

I was sweating alright! I sat back, aching, to inspect the boot. My shirt was now a damp, wrinkled disgrace.

Sylvia raised her leg to likewise inspect my efforts.

'That will do, I suppose,' she said.

She suddenly adjusted her position forward and stood up, covering herself once again with her black office skirt.

'Get dressed and get back to work!' she said.

'S..so..' I stammered, hesitantly, 'I...I'm not fired?'

She grinned.

'Not quite yet,' she said. 'But that all depends on you now, doesn't it?'

She turned away, smartening herself up.

I suddenly became excruciatingly aware of my nakedness, not to mention the adulterous acts I had just committed upon my knees. I hurriedly pulled on my damp, bedraggled shirt and yanked on my trousers. I couldn't even wait to put my socks on before I donned my shoes and left Sylvia's office in silence.

On one hand, I felt relieved that I was still employed. On the other, I felt sick with guilt; guilt because I, a married man, had just been sucking and fucking a married woman who wasn't my wife.

Jill glanced up at me as I arrived back in my office. I saw her quickly inspect my crinkled shirt before looking away without speaking. Did she somehow know?, I asked myself.

There was an email waiting for me. It was from Sylvia. My heart almost stopped when I started reading:

"Andrew. Your assistance is required at a two-day conference in Stratford this Thursday & Friday with me."

I swallowed hard.

"I'm adding this part to the deal, which is as yet unfulfilled as far as I can see. See you Thursday : )"

My heart sank. There was no way out.

I opened my desk drawer and retrieved my mobile. I selected a name from my phonebook and hit the green 'dial' key.

'Hello?' Alison answered.

'Hey,' I said.

'Andrew,' she replied. 'What's up? You sound unhappy about something.'

'Alison,' I said, feeling tears well in my eyes. 'We need to talk....'