My Demanding New Boss – Part 2

"I put into effect my plan of wearing panties and pantyhose to work, hoping my attractive boss doesn't find out."

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After a disturbing nightmare, where I was visited by a hybrid of my boss, Miss Taylor, and my former teacher, Miss Smith, I had resolved to wear panties and tights to work, pretending to myself that I was being directed to do so.

Wasting no time, I’d ordered what I needed and, two days later, I arrived back home to find there had been a delivery. Frantically, I tore the package open, and seven pairs of white cotton panties tumbled out, along with an equal number of pairs of tights. Each pair of panties bore a couple of entwined pink hearts across the front, and these were complemented by a small pink bow at the waistband.

For a few minutes, I fondled the garments, feeling the thinness and softness of the cotton, thinking how different it was to the thick, coarser cotton of my own underwear. And I admired the exquisite elastic in the waists and legs, with its fine looped edges. These garments were unmistakably feminine—there was nothing about them that spoke of masculinity. No real man would dream of wearing them, unless they had been instructed to do so by a dominant woman, such as Miss Taylor.

By now, I was erect and I tore off my trousers and underwear, pulling up a pair of the knickers. The smooth sensation of the fabric against my skin contrasted with the drag of the elastic, tugging against the hairs on my legs. Evidently, the panties were a size too small but that only served to emphasise the feelings I had.

I stretched them over my waist and they clamped into position. The waistband was lower than I was expecting and my erection poked obscenely over the top, further stiffening it. However, I was soon to discover that the tights rose higher, fully imprisoning and restraining my manhood. I was in seventh heaven!

oooOOooo

The next day, I wore a pair of panties along with tights to the office for the first time. As I pulled them up in my bedroom, I again experienced an erection, but I knew it could not be sustained, so it had no need to be dealt with. Sure enough, by the time I reached work my penis was almost limp, certainly shrunk enough for no one to notice.

It was a strange feeling working in knickers and tights. Every moment, I was reminded of their presence—the tight elastic when I was sitting at my desk, and the gentle rubbing of the soft cotton against my member as I was moving around. And all the time I was imagining that Miss Taylor had ordered me to wear them. Several times, the imagery was so strong that my penis swelled.

Twice, Miss Taylor called me through to her office but not to berate me for some major failure—only for trifling matters. Nonetheless, each time I stood in front of her desk my penis would give a twitch. I actually wanted her to tell me off, but I had no intention of deliberately sabotaging my work to create problems. Miss Taylor was adept at finding enough faults in what I did without me manufacturing more.

She, for her part, now seemed to be dressing a little more conservatively, and behaving more decorously, having no doubt deduced I was a lecherous second-in-command. Sure, she still wore her trademark short skirt and white shirt, but she was very attentive to how she positioned her legs when seated. And she was equally careful to ensure that only one button of her shirt was undone, lest she revealed the edge of her bra. Moreover, I could tell that she had taken to wearing a plain white camisole over her bra for extra modesty and, whilst I wasn’t able to confirm it, I assumed she was now wearing pantyhose on a daily basis, after the wardrobe mishap with her stockings. It was all rather disappointing, but I couldn’t blame her for taking precautions.

oooOOooo

Over the following days, I always wore panties and tights into the office, willing that Miss Taylor would take me to task for some mistake.

But it seemed that having made it clear who was in charge, she was calming down a little. Sure, every day, she would criticise me for something that she—using her knowledge of logistics, accumulated in the space of a week—was sure could have been done better. “There’s a lot you still need to learn,” she confidently opined on one occasion, “but we’ll work together, as a team. We will prove the Board wrong about your incompetence, Mr Blakely.”

Occasionally, she would flash me a sweet smile, which appeared to be one of genuine affection, causing butterflies to flutter in my stomach. I could remember Miss Smith giving me similarly sweet smiles on the days when she wasn’t chastising me.

But then, after another week in the office, something more serious arose. “Mr Blakely, I need to see you now,” Miss Taylor called.

I went through from the annex to where she was seated behind her large desk, an irate expression across her face. “I’ve been seeing a modest improvement in your behaviour recently, Mr Blakely, but now you’ve screwed up big time. The foreman tells me that the shopfloor is running out of some… er… widgets. They’ve barely any left! Production will have to stop! This is a crisis!”

Despite my attempts at tuition, Miss Taylor still referred to every single component as a widget, and she was incapable of distinguishing one from another. She passed me a notelet on which she had jotted down a part number.

“Er… yes, they’re CX55 bearings to fit twenty-two-millimetre shafts. I’m sure Rach—I mean Miss Fevers—ordered those in last week, Miss Taylor.”

“You’re blaming Miss Fevers?! It’s your responsibility to ensure the shopfloor has all the widgets it needs. Do not blame others for your own failures, Mr Blakely!”

“No… I’m sorry,” I muttered, wondering why the buck stopped with me and not Miss Taylor, before remembering she had put me in charge of running day-to-day operations while she looked at the “big picture”, the big picture apparently being pointing out my mistakes.

“Ordering widgets so they arrive on time is not rocket science! I’m beginning to think you have the cerebral capabilities of frogspawn, Mr Blakely. You’ll have to stay back after work and sort this mess out! I’ve a good mind to make you write out ‘I must remember to order widgets’ a hundred times, Mr Blakely, so it’s drummed into your dense skull. I expect those widgets to be on the shopfloor by first thing tomorrow morning.”

My brain flashed back to when I was sixteen or more and Miss Smith would put me in detention, making me write out lines, such as “I must not snigger in class”. I was usually the only student there, and Miss Smith would sit on a high stool, reading a novel, just a few feet in front of me. Her long legs would be crossed, pulling up her miniskirt to reveal acres of toned thigh covered in the flimsiest of almost colourless nylon. Occasionally, she would get up, and move behind me, peering over my shoulder at my writing efforts, her warm breath bearing down on my neck. On a couple of occasions, her breasts had even rubbed against the back of my head, causing me to become erect. How I longed for those detentions, supervised by Miss Smith.

“Are you listening to me, Mr Blakely?” Miss Taylor screeched, pulling me out of my daydream. “Your brain seems to be able to retain no more information than a bowl of blancmange.”

“Er… sorry, Miss Taylor,” I replied. “I’ll get it sorted.”

The thought of Miss Taylor putting me in “detention” was causing my penis to swell inside my panties, and I automatically placed my hands in front of my crotch.

Miss Taylor stared, a curious and puzzled expression on her face. Meanwhile, I was going red. She obviously knew something was amiss, and she opened her mouth to speak, but then she thought better of it and waved me away with a look of exasperation.

I returned to my desk and placed a hand down my trousers, fondling my semi-erection through the soft cotton. I had had a near escape from embarrassing myself in front of my boss.

oooOOooo

That night, on getting back home, I was still on a high from being rebuked by Miss Taylor, so I took a bold decision. I imagined that Miss Taylor, as well as ordering me to wear panties and pantyhose, had now told me to destroy all my male underwear. “That way, you won’t be tempted to disobey me,” she had roared.

I did just that! I went up to my bedroom and collected all my underpants in a plastic bag which I dumped into my wheelie bin, knowing that it would be emptied the following morning.

A bridge had been burnt! Unless I was to go to work commando style—unthinkable—I had left myself no option but to wear knickers. I was so turned on by the thought that I browsed online for more pairs to join my small collection of white cotton bikini-style panties. The choice was unbelievably vast and, before I knew it, the shopping basket held dozens of pairs in various pastel shades and in assorted styles and fabrics. Perhaps I would come to own more pairs than Miss Taylor did?

And then I had a further moment of madness. I thought if Miss Taylor is wearing a camisole, surely, she’d expect me to do the same? My penis gave a jolt as I pictured her insisting I did so. Very soon, a few white satiny camisoles were also in the basket. I had to hope that they wouldn’t be detectable under my shirts, but I calmed myself thinking they can’t look too different to a man’s vest from a distance, especially if I wore dark shirts.

After a final look at the shopping basket I pressed “Pay Now”. The deed was done.

I had, for a brief moment, contemplated buying some bras but sanity stepped in, and I decided that Miss Taylor would not expect me to wear a bra to work.

oooOOooo

Over the next couple of weeks, I always wore panties, tights and a camisole under my business suit and no one appeared any the wiser, least of all Miss Taylor. Everything was going swimmingly and I could continue to fantasise that she had ordered me to dress that way.

I continued to crave that Miss Taylor would either give me one of her sweet smiles or would admonish me for some reason or other, hopefully for something that wasn’t directly my fault. Most days, it was one or the other, sometimes both.

Staying in after hours to sort out some supply problem happened a couple more times. I relished the way she was controlling me. Most evenings, returning from work, I would jack off thinking of her—and Miss Smith.

Yet, it also concerned me that she might discover my secret attire or—worse—that I should experience a full-blown erection in front of her.

oooOOooo

Matters came to a head about a month after Miss Taylor had joined the company. A box of what she called widgets had mistakenly been dropped off in her office.

“Mr Blakely,” she called. “For goodness sake! What’s this huge box doing here? It should be on the shopfloor. Are you still incapable of getting an address right?”

“Er… I don’t know why it’s here, Miss Taylor. I’ll take it to the foreman,” I assured her.

“Please see that you do and make sure it doesn’t happen again. I can’t emphasise enough how the Board is losing patience with your mistakes, Mr Blakely.”

I bent down to pick up the box. My back was facing her and, as it happened, my shirt slipped out of my trousers. Instantly, I felt a draught, and panic set in when I realised that my high-waisted pantyhose would be visible above my trousers.

I shot up, and tried to tuck my shirt back in, but it was too late—she’d seen. I turned around to look at her, my cheeks now scarlet.

“It’s not really any of my business, but what on earth are you wearing, Mr Blakely?” she asked, a bewildered expression on her face.

There was no company rule preventing men from wearing tights, so, as she’d implied, I would have been within my rights to have agreed with her that it was none of her business. But I couldn’t bring myself to say that. And, at the same time, my penis was becoming erect. As I was becoming accustomed to doing, I placed my hands over my groin.

“Why do you keep doing that?” she asked.

“Sorry, what?” I replied, knowing full well what she was talking about.

“Putting your hands down there? And you’ve not told me what you’re wearing. I’m curious, Mr Blakely.” She gave me one of her sweet smiles by way of encouragement.

It melted me! “Oh, God, Miss Taylor… if you must know, I’m… I’m… I’m wearing ladies’ tights,” I blurted out.

Her look of puzzlement returned, and she wrinkled her forehead, trying to work out what was going on.

Before she could say anything else, I found myself unnecessarily adding, “And… and I’m wearing panties… and… and a camisole!”

Open-mouthed, she shook her head in disbelief. “But why?” she asked, in a quiet voice. I could tell she was genuinely curious to learn more.

“Hmmm… I don’t know,” I replied, already regretting my forthrightness.

“You must know, so tell me.” She was astonishingly calm, disquietingly so. Another sweet smile crossed her face. I was putty in her hands.

“It’s… it’s because I’m not normal, Miss.”

“Sorry? What do you mean?”

I was now in too deep not to explain further. “You’ve awoken submissive tendencies, Miss. When I was sixteen, and at school, I had a physics teacher who looked exactly like you do now. She was exceedingly strict and punished us boys for even minor demeanours. It used to turn me on and, working with you, Miss, has reminded me of those days and reawakened my desires.”

“Oh! How weird,” she calmly remarked. “What was her name?”

“Miss Elaine Smith. She was the age you are now, Miss Taylor.”

Oh! Right… Where… where was this?”

“I went to school in Oxford, Miss Taylor.”

“Really?” She was silent for a few seconds, mulling over what I’d said. “Okay, but what’s with the underwear?”

“Er… in my imagination, I picture you forcing me to wear it, Miss.” I paused to let her absorb what I was saying, then added, “I’m sorry… it was wrong of me.”

Her eyes shot up. “So, you’re fantasising about me? Do you go home at night and… er… abuse yourself, thinking about me?” She spoke a little louder and more confidently but was still surprisingly well composed.

By now, I was sweating. “Er… yes… sorry. I’m… I’m going to resign, Miss. I’ll write you a letter of resignation right—”

You’ll do no such thing! I told the Board I would sort you out, and I don’t give up easily, so sort you out I will.” She screwed up her eyes and stared hard at me, unblinking, for what seemed like an age. Then a subtle smile broke across her lips—a smile somewhat different to the sweet ones she sometimes blessed me with. This smile had a sparkle, as if something had awoken in her.

“Well,” she announced, with a satisfied nod of her head, “I think I’ve stumbled on a way to improve your job performance, Mr Blakely.”

“Sorry?” I asked, unable to comprehend what she was saying.

“Be quiet, Mr Blakely, and go and stand facing that wall with your hands on your head while I work out exactly what to do.” She had regained her self-assurance and was resuming control.

I couldn’t believe what she’d said. Telling me to face the wall brought flashbacks of Miss Smith giving me the same instruction—nose to the wall and my hands flat on the top of my head.

My penis was swelling at the thought, and Miss Taylor peered down at my crotch. It was pointless for me to attempt another cover up. She could clearly see a tent pole struggling to rise, but her facial expression gave no reaction other than to maintain a slightly eager smile.

She merely repeated her command, “Go and face the wall, Mr Blakely. I won’t tell you again.” Then, almost as an afterthought, she added, “And drop your trousers to your ankles.”

oooOOooo

I lost track of time. Being made to stand still, closely facing a blank wall, was utterly humiliating, but also arousing. My penis was pushing against the constraints imposed on it by panties and tights. I had no idea what she was up to, but, at one point, I heard her turn the latch on her office door, which would prevent anyone disturbing us.

Eventually, she called my name. “Mr Blakely, come over here.”

I hoisted my trousers partly up my legs and wobbled over to her. She was sitting in one of her comfy chairs, her legs crossed, but what attracted my attention was that alongside her, on the floor, was a crumpled pair of tights.

“On your knees, Mr Blakely,” she commanded, thrusting a foot towards me. “Let’s see how submissive you really are, and whether my idea might work.”

I stared at the foot, and at her perfect pedicure, each nail neatly trimmed and painted a vivid scarlet. Despite having no practical experience, I’d read enough femdom literature to know what was expected of me. Bending down, I took her big toe into my mouth and gently sucked on it before rolling my tongue over and around it.

Casting my eyes upwards, I saw her face was expressionless, giving no indication of whether she approved or disapproved of my technique. I began to move along the toes, giving each one attention. “And the gaps between the toes, Mr Blakely,” she quietly instructed.

For five or more minutes, I tended to her toes, caressing each one. Meanwhile, I was also aware that I was again fully stiff, my solid shaft poking out over the top of my panties but still contained within the pantyhose.

“Now lick the soles, Mr Blakely,” she ordered, so I did so, causing her foot to jerk around as my tongue tickled her.

“That’s enough, Mr Blakely,” she announced. “Stand up and face me, with your hands on your head.”

My face must have been crimson as I stood, silently, awaiting her next pronouncement.

“I hope you don’t think I gained any enjoyment from that, Mr Blakely?” she remarked, posing it as a question. Her voice had become more sultry, her face was flushed, and her pupils were dilated. And, from the corner of my eye, I could detect erect nipples, pushing against her shirt. So, yes, I did think she had taken pleasure in that. Yet, that was not the answer she was looking for.

“No, Miss Taylor, I’m sure you didn’t,” I lied.

“It had to be done, Mr Blakely, but I think we can conclude that you’re genuinely submissive towards women. The Board insisted I find a way of improving your competence, and I was told to do whatever it takes. And it seems we’ve found a way of doing it, so your submissiveness may well have saved your job, Mr Blakely.”

“Er…”

“This is not a game, Mr Blakely, but it’s a way of us addressing your workplace inadequacies.”

“Er… yes, I see, Miss Taylor.”

“But I strongly disapprove of you becoming… er… like that,” she indignantly declared, pointing at my erection. “That’s completely inappropriate in the office.”

“Hmm… yes… I’m sorry. I’ll try to not let it happen again.”

“Uhh!” she snorted, “I think we both know that’s outside your control, Mr Blakely. But there’s something I once… er… heard mentioned that will provide a solution.” She stared hard at me, adding in an almost raunchy whisper, “Have you heard of chastity cages, Mr Blakely?”

Yes, of course I’d heard of them, and I’d read stories about them. Wearing one, and being denied erections and orgasms, was a fantasy of mine. “No, I haven’t. What are they?” I asked, as naively as possible.

“They lock onto your… you know… and stop you doing… you know. Yes?”

“I see, Miss Taylor. And you think I should wear one?”

She paused to watch me swallow hard. “Yes, I do, Mr Blakely. I think wearing one would incentivise you to make fewer mistakes at work. If your performance improved, you would have something to… to look forward to.”

“Look forward to? Sorry?”

“Obviously, I would have to look after the key, but if I saw improvements in your work, then I would allow you to spend one night a week without it on to do whatever it is you have to do.”

“Er… yes, Miss Taylor. I do think that would prove to be a big incentive for me to work smarter. Thank you, Miss Taylor.”

“I will order you a good quality cage, made of steel, and you can pay me after it arrives. Okay, Mr Blakely?”

“Thank you, Miss Taylor.”

“From now on, you’ll be punished for any shortcomings in your work, but, if I suspect you are deliberately misbehaving so as to seek punishment, you will find I’ve misplaced the key to your cage,” she declared, a sly smile on her face. “And, you will continue wearing panties, tights and camisoles to work, Mr Blakely, and I will be checking that you do.”

I nodded my agreement, barely able to contain my excitement. “I believe in a carrot and stick approach, Mr Blakely. If, in the unlikely event you exceed my expectations, working harder, more diligently and making fewer mistakes, I may reward you by allowing you to stimulate a part of my anatomy that is more… er… private than my feet. Would you like that, Mr Blakely?”

“Yes, I would… Miss Tay… lor,” I spluttered, struggling to believe what I was hearing.

“Despite the unpleasantness I’d have to suffer, I’m willing to make that sacrifice if it means addressing the Board’s concerns, but it’s a bonus that needs to be earnt, Mr Blakely. Do you think you could up your game to procure the bonus?”

“Yes! Yes, I’m sure I can, Miss Taylor.”

My nightmare, my fantasy, was coming true. Miss Taylor was going to lock me in a chastity cage, was threatening to punish me when I slipped up in my job, was making me wear female underwear and, to top it all, was offering me oral sex if I showed improvement that exceeded her expectations.

Published 3 hours ago

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