Although my job had become stale and repetitive, I saw a glimmer of hope when my boss announced that she was pregnant; I knew I could do her job and that promotion would mean more money for the same effort. Even if I didn't get her job I'd be free of the bitchy control-freak for a few months and could slack off. At my yearly appraisal, with Leah five months pregnant I thought I knew what was coming and how I could best position myself to take her place in three months; how wrong I was.
"Chris, do you enjoy the work here?" Leah asked, running one hand absent-mindedly over her pregnant bump.
"Oh yes, its something I'm pretty good at and the people I work with are all great" I lied. There were more than a few managemerial egos on the floor, cocky salesmen, catty PAs, the office whore, the slackers who would never be promoted, the grads who didn't know there were better companies to work for. I didn't think anyone was bad, just not motivated or enthused, like me, and really just focusing on the paycheque.
"See, I think you're bored, and you need a change to make the job more interesting" she stopped rubbing her belly long enough to swipe some imaginary crumbs off her ample bosom which had only ballooned up and out during her pregnancy. "In fact, having discussed it with senior management, we're going to set you a task that will need completed in time for my maternity leave."
"I have some feedback from your peers that I'd like to share with you." Leah singled out a sheet from the pile she'd walked in with and began to read; "Chris is efficient and polite, however he frequently daydreams and browses ebay for clothes" she looked up for a second, then continued; "More than once I have felt that he was paying more attention to my breasts than what I was telling him. He once corrected me on the pronunciation of Manoloh Blahnik and seems to know more about women's fashion than the average woman. And what's with the ponytail anyway?"
I gave a quizical expression and was about to protest that this didn't have anything to do with anything but before my stammering could abate Leah read from another comment further down the page.
"I remember when Chris and I got a bit drunk in the pub once and he went for a piss, he came back with his flies down and I could see pink satin through the gap. I already know he shaves his legs and I'm also convinced I've seen the outline of a bra strap through his shirt; I was this close to snapping the strap to give it away. Not sure how he'd react though, he's a bit docile most of the time and mostly harmless."
That changed my expression noticeably, and I squirmed in the chair opposite my boss, conscious of the thin silk panties I had on there and then.
"The rest of the feedback is pretty samey, good at the job, but easilly distracted by boobs and pretty clothes. Your colleagues think you wear women's underwear and its getting in the way of your performance."
I didn't know how to respond. My mind flip-flopped between wanting to deny everything and cause a fuss, bluster and stall to buy some time and make a quick exit. But part of me also wanted to admit it, finally cave in and just get the secret out into the open, confess that I loved wearing women's clothing, whiled away my spare time at work shopping for dresses and skirts online and secretly envied my female workmates.
"Chris, we all appreciate the work you do; you're very good at it, but you're making your female co-workers uncomfortable and suppressing something that you don't need to feel so ashamed about. Now, what would you say if I told you that its been discussed internally and management has agreed to allow you to indulge in this fetishistic behaviour to see if it can actually improve your work?"
That sounded too good to be true, and I was keenly aware that so far I still hadn't admitted to anything. In fact I hadn't said anything for so long I was wondering what my voice would sound like when I did speak; would I be able to control myself, avoid stuttering, dismiss all of this as some deliberate attempt to discredit me. But the weak-willed little boy inside of me who had always adored silky, swishy, brightly-colored clothes with zippers and fasteners and cinching won out.
"That would be... nice" I managed in a meak and diffident tone. "I mean... if nobody objects..."
"Wonderful!" she clicked a ball-point pen into life and started to scribble down some notes. "I'll prepare an e-mail to the company so that everyone is aware of the situation and you don't feel self-conscious. Following that we'll start to put into action the handover process so that you're fully trained in my role and able to assist in the transition when I leave." She seemed genuinely happy and for the first time ever she gave me a smile instead of a scowl. I think that surprised me more than anything else.
I was still shell-shocked when I got home that night and showed a print-out of the company-wide e-mail to my girlfriend.
"This seems pretty straight-forward" she had read it through twice already "no different to how companies are expected to treat sex-change requests. In fact, its pretty clever from a business perspective too, if they can make you happier in the job and more productive then everyone wins right?"
I was still finding it difficult to get too excited, there would be a lot of obstacles, a lot of challenges, and while I might have dreamed of a chance to wear what I wanted and be who I had always felt I was inside, I didn't imagine everyone would be so accomodating.
"Oh for pity's sake Chris, cheer up! This is the best thing that could happen to you! You're miserable at work, and only ever seem to cheer up when I doll you up or we go shopping for clothes. You're at your happiest when Mr Dong pays a visit."
Somewhat taken aback that I might be so transparent and one-dimensional I had to remember that Clare had been my girlfriend for over three years now and was well adjusted to my cross-dressing tendancies, even if I wasn't. She had taken to strap-on play with gusto and seemed to really enjoy taking charge and fucking me hard. Those truly were the times I felt most overcome with feelings of serenity and happiness. I got off on admitting to her that I was her cock-loving whore but had always seperated that side of my personality from everything else. People say all sorts of things in the bedroom they'd never repeat elsewhere.
"She asked me to give you this too" I said and handed over an envelope from my boss.
"What is it?"
"It's sealed, I don't know." I felt like I was handing over a note from the head mistress to my mother telling her I'd done a bad thing at school.
"Give it here" she took it and tore it open. Before she started to read the printed pages though she looked me straight in the eyes "Did you try and open it to see what she wanted? Did you try and read it through the envelope?"
I couldn't break away and look elsewhere and after a pause I nodded yes. She pointed to the space in front of her on the couch.
"Kneel there" she commanded and undid the buttons and slid her jeans down to her ankles.
I positioned myself on the floor, between her legs and she took my head and held it from the back, pressing my face down towards her crotch. Clare pulled aside the strip of her thong and began to read. Her hand kept me clasped close to her pussy and as she read on she whispered "Gently" and I began to lick with short, soft strokes of my tongue.
"Oh my, yes" she was already wet when I started and pretty quickly my mouth was coated in her juices. "Oh yes, thats very good" I didn't know if she was referring to Leah's plans or to my ministrations. "We like that" her hand was guiding my head to where she wanted the most attention and pulling my hair when I was getting too enthusiastic. By controlling the pace she was building herself up to orgasm, using me like she would a sex toy.
Her body had slouched down so that her legs were wide apart either side of me, her pussy thrust upwards and so my face could be angled any way she wanted it. Her grip had tightened in my long hair and she had me lapping the length of her cunt lips and paying most attention to her clit before having me back off and start at the bottom again.
"Make a hard tongue" she breathed. I stuck my tongue out and tried to hold it rigid as she pulled me in close in repeated thrusts, fucking her with my tongue.
"Oh this is too good. I'm going to enjoy the next three months" her expression was a combination of lust and mischievous foreknowledge. I could tell that she was getting off on the control of the immediate situation as well as the long-term plans she now knew. Even as I took her to orgasm and her thighs clamped around my head, her fingers squeezing my scalp as if trying to pull me inside her, her body arching and slumping in violent oscillations with each crest of pleasure, she had the letter safely folded away and out of sight. I would just have to wait and see.
The e-mail had gone out late in the day and I had managed to slink out quietly without anyone seeing me but I knew that the next day at work would be difficult. Clare was upbeat though and got involved in helping me dress that morning.
"If everybody knows then you don't need to worry about things showing" she picked out a matching set of simple black satin soft cup bra and shorties. I put them on as I had many times before, only this time I would be wearing them to work under a white shirt.
"And this" she said, and the white shirt turned out to be the white silk blouse I owned instead. "Come on, come on, or you'll be late and everyone will think you turned chicken and quit."
There was no hiding the very obvious black shape through the sheer white material. At least I was wearing opaque trousers. If the object of the exercise had been to make me more comfortable and productive at work then the very opposite was true that first morning; I got nothing done. I didn't take my jacket off for the first hour, and anyone who approached my desk with a work question was dealt with quickly and with a minimum of interaction. Then Abby came over.
Abby had always been a conundrum, in that she was in her late thirties, well-paid, unattached, but had a reputation as the office slut. It was like she didn't care what other people thought and just wanted to enjoy her life; I knew I needed to be more like Abby.
"Hey Chrissy" she had always called me Chrissy, but not until now did it seem more appropriate to the situation. "I'm taking you to lunch. Leah's request."
At the time it didn't seem strange, only later after we were heading out did it occur to me that Abby had nothing to do with Leah's position and would have nothing to teach me about the role. Even then I had to fight through feelings of arousal, watching her stalk ahead of me in her tight pencil skirt and close-cut jacket, and self-awareness, trying to keep my own jacket closed over my chest.
Lunch was relaxed and informal, Abby joked and treated me like an old friend, a polar opposite to the way she'd treated me before. I had to wonder if the feedback about always being stared at had come from her. Whereas previously I would have spent any conversation with my eyes gliding down to her tits, desperately willing the top button of her blouse to pop open, she put me at ease over lunch and I started to open up to her. Pretty soon I was telling her about my collection of underwear, the dresses I'd found, the shoes I owned, I even came close to telling her about what Clare and I got up to in the bedroom.
Over too soon we headed back to the office and Abby held my arm, all smiles. My confidence was soaring and anyone watching would have thought we were lovers from the way she pressed against me. At the office she held me back and let a half-full elevator go, saying we'd get the next one. Once alone inside the next car she flicked the stop button and the elevetaor held where it was.
"Jacket, trousers off. Blouse open" her demeanor had gone strangely frosty, her expression definitely wasn't joking. For the second day now I didn't know if I should protest or not. Still buzzing from our lunch, I let instinct take over and quickly had my jacket and trousers crumpled in a corner of the elevator. As I nervously fumbled with the buttons of the blouse Abby took two determined steps closer and moved in behind me. In her heels she could see over my shoulder and I looked up to catch her glare in the reflection of the wall mirror covering the back of the elevator.
With my underwear on show and the thin gossamer blouse slipping over my skin, her hands wrapped around me from behind, her eyes peeking out. One hand ran over my stomach and down to my panties, where I realised I'd been fully erect for an unknown length of time. Her other hand snaked up and inside the open blouse, over the soft satin of one bra cup, then the other, teasing my nipples through them.
"This is how it goes. When you do good, you get rewarded." Her hand was warm as it slipped over the front of my panties and cupped my cock. I could feel her tight body pressed against my back, the swell of her bulging breasts, the taut material of her pencil skirt. "Today, you did good. I have Clare's permission to reward you."
In the reflection I watched wide-eyed as her hand started to wank my cock through the material of my panties. Her sharp fingernails began to tease and tug on first one nipple, then the other. The visual stimulation enhanced the physical and very quickly I felt close to bursting, lost in sensations of silky lingerie and expert manipulations.
"The better you do, the better the rewards." Abby had perfect control and was able to read my reactions like it was second-nature, she knew I wouldn't last much longer. "There will be all kinds of training still to come. Not just from me, but from some of the salesmen too." She put on a burst of speed before telling me "Pretty soon I think you'll rival my reputation as the office slut."
With that I shuddered and came into the panties, my eyes closing over and my knees trembling, suddenly awash in the warmth and glow of a glorious orgasm. I stood like that, oblivious to Abby for a minute, as awareness crept back in I realised we were moving upwards. I looked round in a panic and she was grinning ear to ear.
"Better be quick Chrissy, only a few floors to go. You won't have time for the jacket, better just pull the trousers on"
I did so, faster than ever, and had half of the buttons closed on my blouse when we arrived at our floor. I had to carry the jacket over one arm, hiding the damp spot that was starting to soak through the front of my trousers. Abby held my arm and pulled me towards the ladies room. Although nobody was watching I felt that all eyes must be on me. My sudden panic was subsiding, but I still hadn't mastered my insecurity.
Once inside the ladies she joined me in a cubicle, pushing me down to sit on the closed toilet while she hitched up her skirt and tugged a pair of red see-through lace panties down her legs, stepping out of them with practiced ease.
"Here, trade you. They might be damp, but not as damp as yours are right now."
Utterly bewitched by what I'd just witnessed I slipped off my loafers once more and was relieved to remove the soaked shorties and trousers. Abby's panties were on the small side and clung tightly to my ass and shrinking cock and balls as I pulled my trousers on again and belted them up before finishing the last of the blouse buttons.
"Lunch again next week?"
It was a date I didn't intend to miss.
The next few days continued to reinforce Clare's theory that in general my co-workers didn't care too much what I wore, or certainly didn't plan to comment openly about it. I had shown her I was wearing Abby's panties when I got home and she suggested I keep them as a trophy, before showing me that she'd bought me some slacks with a side-zipper to replace my work trousers. My attire for the rest of the week was less overt than it had been on that first day and I began to feel more and more comfortable dressing for work.
On the Friday I didn't need any assistance picking out a leopard print set of lingerie. The panties had a panel of satin leopard print at the front that covered my cock nicely and the remainder was sheer black see-thru. The bra was half cup of the same satin print and then sheer for the tops of the cups and surround. Over the top I wore skinny jeans and a tight girly-tee that I'd never worn out of the house before but Clare assured me that dress-down Friday meant no button shirts.
At work I went about my business, and mid-morning one of the trainee grads came over, Oliver. He looked down at my top before saying "Dude, they're awesome!" It took me a second to remember that I didn't have any breast forms in and he was likely referring to the band on the girly-tee.
"Yeah, I got this on their summer tour. What do you need?"
Ollie was temping with one of our European managers who was in town for a few months and didn't have any local staff working for him.
"Thierry wants you in on this meet while I take a letter. He says Leah okayed it."
That immediately got my interest. Thierry wasn't even part of this office and shouldn't have known who I was. Was Leah talking about me to everyone? So far I'd only had to interact with people from my immediate surroundings and workspace, what was Thierry going to teach me?
Ollie and I chatted about various bands and festivals, favorite albums and singles on the way to Thierry's temporary office out of the way around the back of a floor mostly given over to storage. Once there, Ollie knocked and waited for the response before going in. I waited at the door, wondering if I should go in and watched as Ollie put down notepad and pen before crawling underneath the spacious desk.
"Well, in or out, but close ze door" said Thierry with laconic gallic disdain. I stepped in and closed the door behind me. Thierry was an over-weight Frenchman with ratty hair and too many chins. Oliver was only visible as a shape under the desk. He appeared to be waiting for me.
"I heer eet eez dress down Friday. Take zose sings off and show me."
The way he looked at me didn't just make me feel uncomfortable because I was wearing lingerie, he made me uncomfortable as a human. I had to remember that this was another test, another obstacle to overcome, and that good behaviour would be rewarded, as Abby had shown. I pulled the girly-tee off over my head and the skinny jeans off my legs. Whereas at home I would gladly parade up and down showing off my lithe body in silky lingerie to Clare, in this environment I wanted to huddle in a corner and cover myself with my hands.
"Down zere" said Thierry before taking his lecherous gaze off me and going back to his laptop. On hands and knees and in a set of leopard print lingerie I felt like a pussy cat crawling towards a saucer as I joined Ollie under the desk. He had Thierry's cock out and was working it slowly with both hands as it started to pulse and engorge. Even at this point I was amazed at its girth, something akin to a horse cock. As it grew more erect, Ollie started dipping the head into his mouth, wettening the tip and stroking the length with both hands.
"You try," he said, "try and keep your teeth covered with your lips so you don't catch anything." He kept one hand on the monstrous cock, guiding it towards my tentative mouth. The other was placed on my naked, hairless leg casually. Having seen him suck it in and out like he was enjoying an ice cream I tried to imagine the same, instead of this thick foot-long cock glistening with saliva and pre-come. After the first few tastes though I had to gag silently.
Oliver's hand stroked my inner thigh and he soothingly said "It's okay, it gets better" before he took it again into his mouth and started to suck in his cheeks. Thierry made an audible sigh from above the desk as Ollie stopped stroking my thigh and took one of my hands up to cup the heavy, hairy balls sitting below the shaft before returning to stroking my leg.
Together we started to work on Thierry's cock and balls, rubbing and squeezing the balls, stroking the shaft, sucking the head. Ollie would draw the cock out of his mouth and tickle the tip with a flick of his tongue before passing it across to me like a fragile antique to continue sucking on. Ollie's hand had crept up my inner thigh and was touching me through my satin panties, encouraging me to grow, although I would never rival Thierry's cock.
Pretty soon I was doing all the work on Thierry's cock, bobbing back and forth on the enormous head, sucking his juices out off it, pumping with both hands along the length, and squeezing and teasing on the sweaty, hairy ballsack that was pulsing like a heart. Oliver meanwhile had freed me from my panties and was delivering the same expert attention to my cock he'd shown with Thierry's. My mind was giddy with excitement; here I was, sucking off an over-weight Frenchman and being played with by a graduate.
Before I could come though there was a cough from above the desk, Ollie knew what to do and kept stroking me but with his other hand pushed me back slightly so that the throbbing fat cock in my mouth popped free. My hands continued to work the shaft and in three enormous spurts I was coated, face and chest with warm sticky semen. In my surprise I didn't even notice that Ollie had stopped playing with my own cock and moved back out from under the desk to collect his notepad and pen.
"Sank you boyz" said Thierry "You may go now"
Dismissed, I slid back out, looking up towards Ollie who shrugged with a blissfully innocent smile on his face. Gathering my jeans and tee I was about to put them back on when Thierry coughed again.
"Do zat outside, I'm busy" Ollie opened the door and I slunk past him. "Oh, and I shall be sure to tell your boss zat from now on Chrissy, Fridays for you are to be dress up Fridays."
With the door closed, and coated still in his stinking come I pulled on my jeans and top, trying to avoid it sticking to me. I looked accusingly at Ollie and said "I didn't get my reward that time" but he just wiped one finger through a splash of come on my face and said "What do you call this?"
That weekend I told Clare about my encounter with Thierry and Ollie several times and without fail she would get worked up and excited hearing me tell it. She had me hug her close on the couch and finger her through her skirt slowly as I told it the first time. The second time she pressed up naked against me in bed and had me tell her again as she ground her pelvis against my hip. The third time I had to sit naked at her feet as she called Leah and repeated it all to her over the phone, all the while her feet kicked and slapped at my exposed cock and balls. By Sunday afternoon she could have repeated the whole tale word for word and she sent me to the bedroom, telling me to put on a short satin slip and wait for her.
As Clare entered the room, something about her tone of voice scared me.
"It's been quite a week for you, hasn't it Chrissy." I nodded without looking round. "Not only have you embraced this opportunity to display the real girl inside, but you've been tutored in handjobs and blowjobs and taken the spunk of a dirty, fat, Frenchman, all over your face." With each of the last four words she flicked at my nose with her fingers, causing me to flinch away.
"I hear from Leah that Abby is thinking of inviting some of the salesmen she knows to lunch with you both next week. I've told her that if you're going to be on your knees in an elevator desperately trying to bring them off before it reaches your floor then I want pictures." With the last three words she slapped me lightly across my face.
"Leah also tells me that your visibly happier and getting more done, she's overjoyed that your attitude has turned around so quickly. She also says that next Friday you can go in wearing a dress for your one-on-one with Thierry." At the mention of Thierry I felt a shudder thinking of the way he'd looked me up and down.
Clare opened a drawer and started to strap on her black rubber cock.
"One more time, but this time you're going to show me what you did." she sat on the edge of the bed and I kneeled down in front of her starting off with making the head of her phallus slick with my saliva. I mimicked stroking the cock and tickling the balls as I spoke about being confined under the desk with Ollie and his fingers stroking up and down my thigh, wrapping delicately around my own cock. At this Clare said "show me" and I took my cock out from under the satin slip and began to stroke.
When we got to the culmination Clare stood up but held me in place with her hands on my shoulders. "It needn't have stopped there though." she intoned and pushed me forward to bend over the edge of the bed where she had been sitting. Still slick from my saliva she started to slide her unyielding black rubber cock into my ass.
"Wouldn't you have liked to have been bent over that desk? Having that enormous cock slid up inside of you, spreading your cheeks wide open, as that grad watched you, being taken like some sort of office slut. I'll bet Abby respects herself enough not to let herself be used as some fat, hairy, French piece of ass. What does that make you? Hmm?" her thrusts were persistent and steady, her grip firmly on my hips. She knew perfectly well how to gyrate to generate the best effect on her own clit and elicit pleasurable moans from me.
"I said what does that make you?" she repeated.
"The new office slut" I responded, swaying my ass to meet her thrusts and arching my spine to improve her angle of entry.
"You're going to work this week in bright, colourful, patterned satin blouses and your slacks. At lunch with Abby you're going to offer to wank off anyone she introduces you to. You're going to pick out a sweet summer dress for Friday. I want you wearing your hair down and styled for your piggy Frenchman and I'll help you with some light foundation and make-up for him." With each demand she had picked up the pace so that by the time she had laid out the week ahead she was franticly humping me with abandon. I was pushing back onto her cock when she grabbed and held my hips tighter than before and shuddered with delight.
After four weeks of gradually increasing the extent of my transformation from Chris into Chrissy I had enjoyed several lunches with Abby who now treated me like her best girlfriend, had several cupboard or secluded meeting room encounters with men from the sales team who were more than glad to be wanked or sucked off and now spent the entirety of my Friday afternoon dolled up as a pretty girl sucking on Thierry's massive cock until he invariably showered me in his smelly come.
The next monday I was taken aside by Leah.
"Chris, we're all very happy with the increase in performance, and I've no doubt that you're happier too, however I think you need to exercise a little more discretion. With the exception of Friday afternoons when you're working under Thierry" she gave me a wry smile upon saying this "I'm going to require that you seek permission from me first before leaving your desk for anything. One on ones, meetings, bathroom breaks, etc"
This seemed draconian, borderline dictatorial, and I knew that even the old Chris, while bored and mild mannered, wouldn't have stood for it. But there I was, sat across from my boss in tight black slacks that enhanced the curves of my ass and flower print silk pussy-bow blouse, over fuschia pink satin spotty bra and thong. I couldn't muster the indignation required to put up a fight.
"We've used some expenses money to assist your transition too, and there should be a delivery waiting for you when you get home tonight. I'll be looking forward to seeing you bright and early tomorrow."
Meeting over I headed home, dreading what might be awaiting me.
From an unassuming cardboard box I pulled out a steel chastity tube and another, thicker tube which I couldn't work out. Immediately I began to protest to Clare that this was going too far, no job could make me wear a chastity device and I resented the invasion into my privacy. Clare didn't take long to remind me that this was being proposed to improve on my privacy and curtail further indiscretions, furthermore she supported the idea and did I want to start all over again at another job being repressed and miserable all the time in nothing but boy clothes?
Begrudgingly I said I would try it for the week, then turned my attentions to the other tube. Examining it, it looked to me like a salt cellar that someone had hollowed through the middle and left open at each end. Clare knew exactly what it was, either from Leah's original letter or from one of their weekly conversations.
"This" she held up the metal tube "combines with this" she held up an inflatable butt plug we owned "to keep you stretched open. Once the tube is in place inside you, you're held open, and the plug fills the void. Any time you need to go to the bathroom you deflate the plug, do your business, then reinsert and reinflate. But you're effectively handing over control of your sphincter." The look on her face was that same look of mischievous lust. The look on mine was likely one of horror.
Bright and early the next morning, with my penis slid into the metal tube and locked up tightly, its clasps firmly secured around my balls and going nowhere, and my ass feeling held open and extremely vulnerable, I arrived at work in a high collared blouse that buttoned up the back. Beneath the seamless material covering my chest my smallest breast forms were held in place inside a boned basque of white lace that matched the high-cut panties I wore underneath the same women's slacks I'd been wearing for the last month.
"Lovely" said Leah upon seeing me. "Lets get you secured for work then" I didn't much like the word 'secured'.
Sitting at my desk I found that my chair had a thin chain padlocked to the central pillar and the two trailing ends were long enough to wrap around my ankles. Leah asked me to do this as she wasn't able to bend over, she laughed and patted her huge pregnant bulge, then passed me two tiny suitcase padlocks to prevent me from going anywhere.
"If you need anything, send me an e-mail and I'll come over and free you" just as she turned to leave she stopped again "oh, and I almost forgot, speaking of keys, don't you have something for me?"
I had been hoping she would have forgotten, but dutifully handed over the spare key to my chastity tube that Clare had instructed me to leave in my bosses safe keeping, in case for any reason I had to be urgently released. As other people started arriving for work I hunched down and got to it, hoping that I wouldn't need any bathroom breaks.
Hours later I sent Leah a request to be set free so I could fetch some lunch. Instead she sent Ollie over with a salad. He stood next to me with one hand on my shoulder, stroking the satin and feeling the outline of the bra beneath as he prattled on about how he was going to miss Thierry, soon to return to France. I wasn't sure I would miss him that much; I invariably felt pleasurable guilt combined with physical revulsion at any of our encounters. He had started to require that I call him "Papa" and beg to suck his cock before he would start to feed it past my lips.
Each week I would pick out a demure dress and Clare would replace it with ones that were becoming more and more scandalously short and revealing. Although my afternoons were spent sequestered away sucking Thierry's cock, my mornings were still spent with my colleagues, more than a few of whom would make private requests for some face time or future lunch invites. Hopefully this new phase of chastity and discretion would mean my attire could be more formal on Fridays.
I spent the rest of the week chained to my chair, occasionally sending pleading e-mail after pleading e-mail to Leah to allow me to go to the bathroom. The plug didn't help at all as it left me feeling constantly exposed and it was only after I willed myself to consciously relax my sphincter that I started to feel better about it. The chastity tube stayed on as well and each morning I would awake earlier than usual, dressed in a long silky nighty or slip, rolling in pain, clutching at my trapped and engorged cock as it tried to bust through the metal unsuccesfully. Clare found this amusing each time, and would suggest I spend the extra time awake getting ready for work.
That Friday I was surprised to see a very nicely tailored skirt suit hanging for me to try. I leapt at the chance to combine a waist cincher and stockings with it and with the exception of the visible bulge of the chastity tube against the tight material of the skirt I could have passed myself off as a corporate lawyer on her way to a high profile case. Clare also suggested I wear heels that day so I put on low, sensible shoes and went to work, early again.
Eager to see Thierry's reaction I even showed up to his office earlier than usual, no longer apprehensive at the thought of playing at baby girl and sugar daddy. At his call I strutted into his office and stood before him feeling powerful and confident, determined and perhaps even a touch defiant. He looked me up and down and gave a whistle before opening a desk drawer and placing a small cardboard box on his desk.
"A geeft, for ze pretty lady before me, please try eet on."
The box contained the next size up of anal stretching tube.
By the end of the second month I had transformed from bored office drone hiding away a shameful lingerie fetish to openly bisexual office slut willing and available for anyone to take their pleasure from to serious and efficient hard working girl in constant chastity. Thierry had gone back to Paris but had left me with what he referred to as the last necessary size of stretching tube; I could no longer feel any muscle resistance and depended entirely on the plug to keep me from spoiling my skirt suits. Clare had become over-sexed at home and was loving that I was no longer two different people depending on the situation but always Chrissy and always available for immediate gratification; hers.
Abby had taken to only seeing me every so often to share catty comments about the underacheivers in the office and would forego our lunches with one exception. In the second week of the new month we stole away an hour's release from my desk chains and went to Thierry's old office. Once there she had me slip off my shoulder-padded jacket, pinstripe skirt, undo my blouse and remove the breast forms which were now in almost permanently and gave me an ample C cup. These days I barely noticed other women's breasts at all.
I stood in front of her as she leaned against Thierry's old desk, wearing my corset, with eight thick garter straps leading down to lace-top stockings. Over the top I wore a pair of red see-through lace panties identical to those she had bequeathed to me on that first day, and from this she motioned for me to pull them aside and show her the chastity tube she had yet to see in place.
"How does it feel?" she asked, staring at it the way I had once stared at her cleavage.
"I'm fine with it now. The first two weeks were the worst; I was constantly horny, horniness led to attempts at erection and erection led to crushing pain. After a few weeks I managed to get the horniness under control and now I can pretty much stop it before it becomes an issue."
Abby's eyes stayed on the tube, "Does that mean you can't get erect anymore?"
"It's more like I have control over it and it doesn't happen spontaneously. I'm pretty sure if you had a key I could get erect immediately for you."
"We don't have permission for that" she sighed. Then her eyes narrowed and she reached out for me. I approached her tentatively but relaxed as she took my head down to her chest, stroking my head.
"I can't believe the progress you've made. Leah was right that one nudge would break you and then in no time at all you could be remolded. You barely had any resistance at all. Doesn't this feel much better than being a repressed little pervert stealing glances down women's tops?"
I was starting to enjoy the proximity to her and the soothing stroke of her hands through my hair.
"Better that you're a motivated and productive whore like me, using your body as a tool to get the job done and never having to feel ashamed for any of it."
I had grown to appreciate Abby as my best friend by now but suddenly my mind couldn't stop replaying how expertly she had made me come in my panties in the elevator all those weeks ago. There was a stirring sensation within the chastity tube and I fought hard to suppress it. Her hands were no longer stroking my head, they were running across my naked back and undoing the clasp of my empty red lace half-cup bra.
"Tell me, how wide is your asshole now?"
I didn't know how best to describe it for her. Clare could no longer touch the sides if she used her strap-on, it would slip in and practically rattle around uselessly. She had taken to fisting me instead to acheive the same result, but in the chastity tube all that came would be dribbles of pre-come and feelings of frustration on my part. Clare now wantonly used me for her own pleasure first and just as Abby had said, I would use my body, my tongue, my fingers, whatever it took to ensure she enjoyed herself. I no longer focused on my own selfish pleasure first and that made it easier to avoid erections.
I was having to work hard to ignore one now as Abby's hands started stroking my chest and her fingers pinched and pulled at my nipples which had become centers for extreme sensation at the expense of all others. With a sudden twist and push she had me on my knees in front of her, both nipples in a vice-like grip. My cock was trying to break through steel and my hands flailed, catching her wrists eventually. She stood over me like some alpha female, looking down into my eyes.
"Listen carefully you fucking fuckwhore" her voice was a low growl "I might love you like a sister, and you may have been fast-tracked for promotion ahead of everyone else because someone on high has a fancy for sissy fuck toys but if you ever forget how you got here and let any of this go to your head because you think you're special..." she left the thought hanging in the air for a second and I knew there and then that I couldn't and never would.
"Don't forget I have video of you taking three cocks in your hands and mouth, dressed in nothing but satin bloomers and camisole, squealing with glee as they all spurt in unison on you. Don't forget who helped wash three loads of Thierry's spunk out of your hair so you could go home looking half decent. I know right now you'd give anything to come even if you think you have it under control and that its going to take someone with a cock the width of a Coke can to fill your fuck hole. You're lucky you work with people who recognised you for what you were and groomed you especially."
Her voice softened and although my nipples no longer had any sensation in them her grip loosened and moved to stroking and teasing instead, my erection hadn't abated through her tirade and I was utterly focused on her still.
"In a few weeks Leah will leave to give birth. Her husband is just lucky that the kid won't come out speaking French" I was slightly astonished at this. "That's right, the kid isn't his, its Thierry's, she's been his foreign affair for years now and he pumped her full of his smelly love seed right here over this desk. I was there to lick up what didn't impregnate her. Then what to do? Thierry's needs must be met. He visits at least once a month and needs... shall we say, a capacious recepticle. Ollie was a temporary fix but wasn't willing to go far enough to meet the company's needs so Leah picked you. You were more than capable of taking over her professional responsibilities but when we discovered that you were a malleable sissy behind closed doors well, in good business fashion we sent a proposal to your girlfriend and started the process for a seamless handover."
Even with the plan exposed before me and seeing each step in the transformation being undertaken I didn't feel manipulated, in truth this was equally something I wanted too. Now realising that I had been herded and forced into my darkest fantasy I had to admire Leah. Abby had raised her skirt and been delicately fingering herself as she exposed the devious plan they'd undertaken and now drew my willing lips closer to her cunt.
"What went for Leah goes for you too. I'll indulge Thierry in his sick love games, guide his fucking enormous cock into your hole and wipe away your tears as he ruins you inside and out. I'll suck the come that dribbles from your hole and down your legs and get you home safely when you can barely walk. After all, we're best girlfriends now and you're my new boss."
Kneeling between her legs, eating her out passionately, cinched painfully tight in my corset, legs bedecked in silk stockings and heels, my nipples numb, my cock imprisonned and straining against the unyielding chastity tube, my asshole stretched and throbbing at the thought of taking a foot of cock until it blasted my insides with copious spurts of the same semen that had impregnanted my evil boss, all I could do was nod.
written by Deedee Van Uber