I couldn't believe my luck! For me, it was a fantasy come true. Miss Taylor, my attractive young boss, had discovered my secret crossdressing and submissive tendencies. Furthermore, she had decided I should wear a chastity device, a long held dream of mine. It was on order, and we were awaiting delivery.
oooOOooo
Two days later, I was summoned into her office. “Please lock the door, Mr Blakely,” she advised, in a sultry voice. “Then stand in front of me.”
I did so, and she peered up at me from behind her desk, wearing her usual office attire of a crisp white shirt, her hair looking somewhat wild, as it so often did.
“Are you correctly attired, Mr Blakely?” she enquired.
I knew what she meant—an underwear inspection was coming—but I was finding it difficult to speak, so I gave a nervous nod.
“This is very embarrassing for me, but I must ask you to pull your trousers down and lift your shirt up so I may check,” she politely demanded. Embarrassing for her?
With my face flushed, I undid my belt, top button and zip, and I let my trousers slip down, revealing that I was wearing a pair of pink bikini panties beneath light black tights. She gave me a faint smile of encouragement, and I pulled up my shirt to show I had on a white silky camisole.
“Good boy,” she concluded. “I wouldn't think many men would look good in lingerie but you... well... er... hmm...” Her voice trailed off, as she sensually ran her tongue over her top lip. Then appeared that faint smile and that glint in her eyes that I'd seen before. There was an element in seeing me humiliating myself in female undies that triggered something deep inside her psyche.
“Er... thank you,” I replied, red-faced, for want of something better to say.
For a few seconds, she seemed to be miles away before snapping out of a daydream. “Erm... I won't inspect you every day, Mr Blakely, but I will be most disappointed if I were to discover you were disobeying my rules—most disappointed.” She paused to let that sink in before adding, “You don't want me to be disappointed, do you, Mr Blakely?”
“No, Miss Taylor,” I agreed.
“And what's with the hairy legs? We could weave a large rug using that fur. I expect my staff to take a pride in their appearance, Mr Blakely, like Miss Lawson and Miss Fevers do. They don't have hairy legs.”
The message was clear. I was to start shaving my legs. I nodded my agreement, whilst becoming aware that I was also becoming stiff. Standing there, in female underwear, in front of a fully dressed, alluring young lady, was proving too much.
She glanced down at my growing erection and rolled her eyes. “You'd better get dressed, Mr Blakely. That doesn't impress me. It's totally out of place, but luckily we have a cure.”
I pulled my shirt down and my trousers up. Meanwhile, she fished a small box from a desk drawer and pushed it in my direction. It held the chastity cage she wanted me to wear. Attached to it was a small but robust looking padlock—it was open, although the key was missing.
“Take this home with you, Mr Blakely, and do whatever it is you need to do, remembering that it'll be a week, at the earliest, before you can do it again. When you're done, put the device on, snapping the lock shut. I'll inspect it tomorrow to ensure it's securely in place. Any questions, Mr Blakely?” Her voice was cracking up a little, and I sensed she was becoming aroused at the thought of me being denied sexual release for a week. She provocatively fingered the topmost fastened button of her shirt but stopped short of undoing it.
“Er... no, Miss Taylor. I'll do what you ask.” Even as I said those words, I felt my penis tumesce in anticipation of being denied the privilege of tumescing—the irony did not escape me.
oooOOooo
That evening, I masturbated not once, but twice. To be frank, the second attempt was a struggle, so soon after the first, but I felt I needed to drain myself of every drop of semen if I was to survive a week locked up.
I slept restlessly that night, my brain being unable to put my fate to one side. I woke early, with a solid erection, making me wonder how on earth I would cope with a week of denial.
After breakfast, I used ice to cool my ardour. Subdued, I slipped on the chastity device, and, after just a brief moment of doubt, I snapped the lock shut. My stomach turned a somersault as reality set in—for the next week, at least, Miss Taylor had assumed control of my sex life, such as it was.
oooOOooo
I arrived early in the office that morning. Miss Taylor was already there and had a wily smile on her face when she saw me.
“Well, let's see,” she remarked. “Lock the door and then strip down to your undies.” She said it so matter-of-factly, as if it was the most common thing imaginable for a subordinate to undress in front of their boss.
“Remember, this is as uncomfortable for me as it is for you,” she added. Really? “But it has to be done if our plan to improve your performance at work is to be successful.”
Gingerly, I stripped off, until I was standing in front of her wearing my panties, pantyhose and camisole. My face was scarlet, and hers was pink.
She maintained a stern expression, appearing dispassionate, while she peered down at my crotch, staring at my pale blue satin underwear. “I can see the outline of your chastity device, Mr Blakely, but we do need to confirm that it's locked on.”
She looked up at me, and it was obvious what I had to do. I lowered my tights and knickers, giving her free access to my cage.
She stood up from her desk and moved closer to me. I could smell her fragrance but there was something else, something underlying that delightful perfume. It was, I was sure, the scent of arousal pheromones that I could detect.
I looked at her. Her breathing rate had increased a little and her pupils were widening.
“What?” she sharply asked. “Why are you... staring?” Her voice was raspy.
“Er... sorry, Miss Taylor. I didn't mean to stare.” I dropped my eyes as she fell to her knees in front of me, peering closely at my imprisoned penis.
Had someone somehow burst into the office at that moment, they would have thought she was about to give me a blowjob, but that was impossible. But the thought made my dick try to expand.
Cautiously, she took the padlock between two fingers and gave it a wiggle, exhaling heavily as she did so. Then she stood up again, looking flushed.
Being several inches shorter than me, she gazed up at me. Speaking breathlessly, she remarked, “I hope it's... not proving too... uncomfortable, Mr Blakely, but, as I've explained, we're... working as a team to protect your job.”
“I understand, Miss Taylor. I'm determined to work with you to keep my job.”
“Good boy, Mr Blakely,” she concluded, strangely adding, “I'm sure Miss Smith would have been proud of you. Now get dressed.” She paused to watch me pull up my tights and knickers and then gave me a satisfied smile. “I do so hope that you show improvement in the way you work, Mr Blakely. Maybe, if you put in enough effort, you may even exceed my expectations. Hmm?”
My penis gave a massive jolt, causing me to wince. “Exceeding her expectations” was code for her allowing me to have oral sex with her.
“I will do everything I can to exceed your expectations, Miss Taylor.”
She grinned at me, concluding, “I'm sure you will, Mr Blakely, now you may finish getting dressed and get on with your work. I'm not to be disturbed for the next half-an-hour.”
I returned to the annex where my desk was, and she locked her door behind me. As I tried to concentrate on a spreadsheet, I could hear a faint buzzing noise from her office accompanied by some gasps and yelps.
oooOOooo
Wearing the cage was strange. I had to tell myself not to think of Miss Taylor—or of Miss Smith, for that matter. Perhaps the device was too small—it seemed unable to accommodate even the smallest of swellings, causing me much discomfort. I did wonder whether to say something to Miss Taylor, suggesting that the cage should be exchanged for something a tad larger, but then I quickly realised that being denied attempted erections was a price I must pay to serve her. And, after all, being restrained in this way was something I could once only dream about, but I was now experiencing. I was honoured to be able to suffer.
Nights were the worst, or rather the early hours of the morning when my penis chose to wake up ahead of me, only to discover it couldn't. I was having to spray cold water onto myself to dampen my dick's enthusiasm. And then came the weekend, which was also challenging, not only because my frustration was growing, but I was denied sight or sound of Miss Taylor. I was on my own, with no input from her to keep me motivated.
Nonetheless, come Monday I was back in the office, knowing this was the fifth day of my being locked up. On Wednesday, I was expecting to be released for the night, and I had no intention of committing any major faux pas that might cause that date to be put back. To that end, I diligently checked and double-checked everything that I, Miss Lawson and Miss Fevers did. If either of these two women was curious as to my newfound zeal for reducing mistakes, then neither made any mention, and neither had any reason to suspect my strange relationship with our boss.
oooOOooo
As the days passed, my sexual frustration grew, almost exponentially. One part of me wanted to be punished by Miss Taylor for some misdemeanour, but another part of me knew that I also needed to release the build-up of semen. I had never gone so long without masturbating, so it was essential I did not blot my copybook, causing her annoyance.
I avoided making major mistakes, and Miss Taylor seemed pleased with me, occasionally telling me off over some minor issue, but also now and then flashing me one of her sweet smiles—smiles that made my knees go weak and my penis to spasm inside its cage. Once or twice, she even touched my arm!
Eventually, Wednesday arrived, the day when I expected to be unlocked for a night of masturbatory frenzy. With just a couple of hours to go, the end was in sight when she called me into her office. She was sat behind her imposing desk, a distinctly unhappy expression across her face. I knew instantly that I had blown it—there would be no release for me that night.
In front of her, was her open laptop, which she swivelled around so I could see the screen.
I could see an email I had been sent a few days earlier by the foreman on the shopfloor. It was a request that I order in more of a vital component, supplies of which were running short.
“Did you order these widgets, Mr Blakely?” my inquisitor asked, speaking softly but menacingly.
“Yes, I did, Miss Taylor. I clearly remember the order being put in. They should have arrived this morning.”
“What arrived this morning, Mr Blakely, was a tonne of widgets labelled XVW456.” She paused, almost for dramatic effect. “What was needed was a tonne of widgets identified as XVW466!”
“Er...” My God, I'd screwed up again. I felt my penis twitching inside its small cage. “I'm sorry... Miss Taylor. I don't know what happened.”
“I know exactly what happened, Mr Blakely. You ordered the wrong blasted widgets!”
It was actually Miss Fevers who had placed the order, but past experience told me that Miss Taylor held me responsible for anything and everything that went wrong.
“Lock my office door, Mr Blakely, and then go and face the wall while I decide how you should be punished.”
I felt my face go crimson as I recalled Miss Smith, my former teacher, using those exact words two decades earlier. Meekly, I did what Miss Taylor ordered, my penis throbbing inside its small cage as I tried to work out what my punishment might be.
As I stood there, I heard Miss Taylor phone the foreman.
“Hello, Mr Arkwright, this is Miss Taylor again. I can't apologise enough for what has happened—”
...
“Yes, Mr Arkwright. I do appreciate that production has had to completely stop and—”
...
“Yes, I know it's costing us a lot of money but—”
...
“Yes, I do understand the seriousness of—”
...
“Please! Mr Arkwright!! Please let me finish a sentence, for God's sake! I'm taking measures to ensure this never happens again. I can assure you that the person responsible for this calamity won't be sitting down for a week and—”
...
“No, I won't name the person responsible for this debacle, Mr Arkwright, but I will admit that this person has the brain power of a dandelion.”
...
“Yes, I totally agree with you, Mr Arkwright. It is a great shame that capital punishment has been abolished, especially in the form of hanging, drawing and quartering, but we are where we are, and—.”
...
“No, I am not being sarcastic, Mr Arkwright. Look! Leave it with me! I must go, Mr Arkwright, and get this blasted mess sorted. Bye!”
Before the foreman could say anything else, she hastily closed the call and let out an enormous primordial scream. “You see the problems your stupidity has caused me, Mr Blakely!!” she screeched. “All you had to do was correctly copy a six-digit code. A long-sighted pigeon with dyslexia and broken spectacles could have done a better job than you, Mr Blakely!”
“Sorry, Miss Taylor,” I quietly but inadequately replied.
“Arghhh!” she screamed in frustration, banging her desk with her hand. “Saying sorry is not good enough! When you screw up it reflects on me, and my record becomes stained with your incompetence. Come over here, now!”
There was no mistaking her anger. Nervously, I made my way over to her. She was sitting in one of the low-down comfy chairs.
“Sorry, Miss Taylor,” I ventured to say. “Thank you for not naming me.”
“If I'd named you, you'd have got the sack, Mr Blakely, and I'm doing my damnedest to make sure that doesn't happen. I hope you appreciate the efforts I'm making to keep you here, Mr Blakely?”
I did appreciate it. No way did I want to be fired from this job. But, equally, I knew that neither did Miss Taylor want me gone. We were a team, as she kept reminding me, but certainly not a team that Human Resources or the Board would approve of.
“Thank you, I'm very grateful, Miss Taylor.”
“You should be!” she hissed. “I thought you were improving and then this!”
“Yes, it shouldn't have happened. It was stupid of me.”
“Did you deliberately do this, so you'd be punished?” she asked, her voice now a little calmer.
“No!! No, I didn't! Because I know you now won't unlock me today, and I was desperately looking forward to being free for the night.”
“Hmm...” she thoughtfully remarked. “Well, you're right that you won't be unlocked, Mr Blakely. But you still need to be punished, don't you?”
“Yes, Miss Taylor.”
“You're a submissive, Mr Blakely, but are you also a masochist?”
“No! I don't like pain. I'm not a masochist.”
“So, you wouldn't enjoy being spanked over my knees, then?”
The thought of going over her knees—a hope come true—caused a dribble of precum to emerge from my penis, and I felt it wetting my panties. True, I'd never been spanked (regrettably, Miss Smith wasn't allowed to use corporal punishment on miscreants like me) but surely it can't hurt that much. “No, Miss Taylor, I don't want to be spanked,” I replied, trying to disguise my true desire.
“Well, you need to be. You need to be taught a lesson, Mr Blakely. It's humiliating for me to have to spank you, but it's in your own interests, and the interests of the business, so I will steel myself to punishing you in that way.”
I nodded and tried to agree, but no sound came out—I was too jittery to speak.
“Come on,” she urged, “Everything off below the waist.”
I stripped as quickly as possible, revealing my chastity cage, which she glanced down at. “I'll be incensed, Mr Blakely, if your cage rubs against my tights and causes a ladder.”
“Yes, I understand, Miss Taylor... Er... how about removing them, Miss Taylor, so they don't get damaged.”
“What? Are you getting some perverted pleasure from this, Mr Blakely?”
“No, Miss Taylor!”
“Hmm? But I think you're right. Turn your back on me, Mr Blakely. I don't want you seeing things you shouldn't be seeing.”
I did what she said, and I heard her kicking off her shoes. Then there was a rustling sound. In my mind, I pictured her raising her skirt a little and then reaching up, pulling down her tights.
“Right, Mr Blakely, get yourself over my lap. You're going to receive the spanking of your life.”
She pulled up her skirt a little, but not high enough to reveal her panties. Cautiously, I lowered myself down, feet and hands on the floor, and my cage resting on her legs. I could feel the warmth of her body against mine, causing me to become aroused—or at least as aroused as I could be, locked in my cage.
Slowly and rhythmically, she began tapping my bottom, her left hand striking my left buttock and her right my right. The sensation was a pleasant one, and it was further exciting me. I was aware of precum drooling from my penis and acting as a lubricant between my cage and her legs. I was enjoying the experience—good grief, it was hardly a punishment.
But then, after a few minutes, she increased the pace and the intensity of the blows. Her attack was frenetic, and very soon I was wriggling as the fury of the strokes intensified. I very soon realised that I had misjudged the playful taps at the outset, and the arousal I had initially felt quickly vaporised.
How this couldn't be hurting her hands, goodness knows, because it was most definitely hurting my buttocks. And, surely, this was not the first time she'd administered a punishment spanking.
I resisted crying out for as long as possible but eventually had to let out some howls. Yet the beating still continued. She was now down to using only her left hand, her right one pinning my back in place.
Eventually, she stopped, which is when I became aware of her heavy breathing. Was it from exertion, or was she turned on? She then tenderly ran her fingers over my bottom in a way that I could only describe as sensual. Nothing was said, but she continued her soothing actions for several minutes.
“Right! Up... you get, Mr Blakely!” she suddenly gasped. I stood up and looked down at her thighs. Precum was visible from where I'd leaked. She looked down as well. “Ugh! What's that?” she asked, acting surprised.
“Er... sorry, Miss Taylor.”
“It's disgusting, Mr Blakely! What is it?”
“It's... it's precum, Miss. I leaked... sorry.”
“Ugh! Do you honestly think that's acceptable?”
“No... it shouldn't have happened.”
“Then you'd best get rid of it.” I glanced around for something to wipe it off with. “No!!” she screeched, “I don't want you touching my thighs with your hands. What sort of girl do you think I am, allowing you to grope me?”
“Er...”
“Use your tongue, Mr Blakely. Consider it to be a punishment for leaking. Get down on your knees.”
I dropped down and carefully used my tongue to lick off the precum, my penis once again growing and then throbbing in pain at what she was expecting me to do. She pulled her skirt up a further couple of inches. Surely, she must have been less than an inch from revealing her panties to me.
“And there's a bit there,” she pointed out, speaking in what was becoming an increasingly husky voice.
I looked, but there was nothing to be seen! How could there be as it was on skin that had been hidden by her skirt. But I wasn't going to argue. I bent down again and licked all around the spot she had pointed to, imagining she could see something that was invisible to me. As I did so, I edged further up her thigh, getting nearer to her pussy, which, along with her panties, was still obscured from view. As I got closer, I could smell her sexual arousal. She must have been sopping wet.
I prolonged my bout of cleaning, moving from one thigh to the other, sensing that was what she wanted. “Keep going, Mr Blakely, I... I don't want a single molecule of your... nasty biological fluids to remain.”
Finally, she instructed me to stop. “Get dressed, Mr Blakely. Have you learnt a lesson?” she enquired.
“Yes, Miss Taylor,” I meekly replied.
“Don't you dare rub your bum!” she exclaimed, as she saw my hands about to do just that. “If you can avoid any more fiascos over the next couple of days, then I'll unlock you on Monday, Mr Blakely. I don't bear grudges, so tomorrow will be a new day with a fresh start.”
“Thank you, Miss Taylor.”
“But you need to stay behind after work to sort out Mr Arkwright's widget problem. I wish I had the time to say behind with you to make sure you do it. Understood?”
I gulped and nodded. Once again, she was putting me in what I imagined to be detention, just as Miss Smith used to do, but, regrettably, she wasn't going to stay to supervise me.
