BDSM Library - Carpeted by The Boss

Carpeted by The Boss

Provided By: BDSM Library
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Synopsis: A young submissive transvestite is put to work by its Master at the Master's company's offices as a Junior Admin Assistant. The sissy's inability to adhere to office standards leads to it receiving a personal disciplinary in Master's office.

Carpeted by the Boss

 

I waited patiently outside Mr. Sharps office, reminding myself that although it was "Master" once I was inside his office, or at home, it was Mr. Sharp out here in the foyer. My new colleagues were beginning to head home. It was 5:30 on Friday afternoon and everybody had plans, except for me. Nowadays, other people had plans for me. I just tried to do as I was told.

I could hear nothing through the thick door. But my Master valued his privacy and I knew from bitter experience that the office was well soundproofed.

I started nervously, remembering that I would imminently be required to present myself for inspection. "Best check that Im tidy" I thought, running through my checklist of .

I looked down to make sure that my sheer, glossy stockings are straight. Yes, they're fine. My skirt does, just cover the lacy tops at the front and back, but I reach down and tighten the four, red suspenders until theyre taut, just to be sure. As long as I don't bend or try to run (fat chance in these 4" heels), Ill look vaguely respectable. My blouse is not, I think, too transparent. Sure my bright red, lacy, half-cup bra is clearly visible, but my budding, hormone-induced nipples are not. My make-up and nails are still tidy and, considering the time, I take some pride in that. All the same, I take out a compact from my clutch bag and apply a touch more "deep crimson" lip varnish and clear, shiny gloss.

My wait is over, as the door opens and my Master instructs me to enter. I walk in and close the thick door behind me, heart pounding and my knees and fingers beginning to tremble with fear. I turn to him, now seated in the large, leather chair behind the wide mahogany desk. I try to smile and drop what I consider to be a neat curtsey, before asking in a reedy, quavering voice

"Master, you summoned me?" and curtseying again.

"I did, slut," he tells me tersely after a pause. "Have you been well behaved today?"

"Yes Master, very well behaved Master" I reply, nervously.

"You say so, slut, but I was at lunch today with a couple of the chaps in sales and they were telling me that the "tarty little bit of student placement fluff" had been giving them the come-on this morning" and you are the only tarty little bit of student placement fluff here at the moment, so what am I to think?" he asks in a calm, friendly voice that fools me for not one second.

"Master," I plead, panicking now. "It couldnt have been me. Ive been really good. Ive not flirted with anybody. I wouldnt dare. Honest!" And now my knees are genuinely quivering, as I know that Im telling the truth, but that this will count for nothing if my Master decides that I must be punished.

"Well, pussy, Marcus and Joel were emphatic that this little slut was stood next to them at the photocopier in the sales office and had deliberately bent forward over the machine to flash them a good shot of her ass and panties." I go white as I see him remove a short leather whip from his desk. "Still sure that youve been a good girl, Pussy?" he asks, more threateningly this time.

"Yes, yes Master. Of Course!" I plead, but doubts are now filtering into my mind, as I remember copying some reports in the sales office during the morning. Had they been there? I couldnt remember. God my memory was turning to shit lately!

"This wanton little slut had on lace-top stockings and a red suspender belt, with four suspenders" he tells me, flexing the little whip.

"Oh shit!" I think to myself, fearing the worst.

"Yes, and red, see-through, mesh panties with tie-up sides. Real whores gear they were saying, and who can blame them, eh? Some little slut flashing those at you over the copier? What are they meant to think?"

"Oh Master no!" I beg, clasping my hands together in front of me in genuine supplication. "Please, Master, I didnt flash. I didnt know. I didnt!"

Im silenced as the little crop lashes down on the desktop and my Master stands up threateningly before me.

"Lift your skirt, slut!" he orders and, picking up the short hem, I comply, biting my lip as I raise the light material the few inches required for my lacy stocking tops, suspenders and finally my crimson "Anne Summers" tie-up panties to peek into view.

"Well, well. What have we here?" he teases, without expecting a reply. "We have a lying little bitch whos been flashing her juicy, cum-hungry ass at my staff!"

I try to protest my innocence, but my mouth is too dry to speak. I cringe as Mr. Sharp approaches and squeal in pain as he seizes me by my mane of blonde hair and throws me forward onto the thick-pile carpet, where I land heavily on my knees. I try to rise, knowing what is in store, but I feel his foot, firm and heavy, pressing down on the back of my neck. I then feel a tight grip on the back of my panties, pulling roughly upwards, forcing the material into my crack, lifting my hips high and exposing my smooth buttocks.

"Theres only one way to teach you not to lie to me, my little whore!" he tells me in the same patronizing, sing-song voice. And then I seize and cramp in pain, my mind blanking and white lights exploding in front of my eyes. I didnt even hear the skinny, heavy, leather whip land. The thick carpet muffles my whinny of animal pain and fear as the whip lands again, this time on my other buttock. I writhe in agony, my legs kicking to try to escape and my back bucking against his tight grip, all to no avail. As the whip bites home, 3, 4, 5 times I hear my Master telling me like a child that Im his slut and that my ass belongs to him. I try to agree, I beg, I plead, I submit, until the sixth lick of the whip hits me and Im dropped, sobbing and moaning onto the carpet, clutching at the hot, pronounced red wheals that mark my pretty ass.

"Im sorry Master" I sob "I wont do it again, Master".

But then I hear him close behind me where I kneel "Im not finished with you yet, my cum-hungry slut!"

I feel him close, his hand again taking a rough grip of my panties but this time shoving them to one side. Your big tool pushes insistently against my pussy and I try to relax in time to let it in with minimal pain. Too slow, I realize as I cry out in pain as it thunders into me; 6 thick inches in one thrust. I bow my back to stretch away but Im seized by my hips and powerfully pulled backwards at the same time as thrusting forward with a grunt that brings about a reciprocal cry of pain from me as this time, all 8 inches violate me. He begins to pump rhythmically into me, his pelvis slapping loud against my butt. My eyes feel like theyll burst out of my head and my mouth is wide and silent as I try to relax. My butt is now warm like Deep Heat, glowing through me. His cock explores and penetrates and invades me and I cant help but respond. I hate myself, but something in there feels undeniably good and the added humiliation of being abused and beaten and down on bruised knees with my ass crammed full of cock lights up the darker side of my psyche.

Soon Im moving with him, my long, painted fingernails gripping deep in the carpet as I push myself against him, head back, whispering encouragement and debasing myself.

I react in pain again as his big hand lands heavily on my tortured rump and he taunts me to be "Louder bitch! Tell me whos your Master!"

I let go and begin to moan as I grind with him, my little cock now hard and escaping from my skimpy pants as I reach down to grip myself and start to pump.

"Oh God, Yes! Master, Yes! Fuck me Master! Pleeeeeeassssse! Im your bitch Master please! YESSSSS!" I exclaim as his pace quickens and the weight of his thrusts increases. Im close to orgasm and get even closer as his big hand slaps my dainty little one away and encloses my tiny, hard cock. I can take no more and as I hear him starting to cum, my slim arms give way and his full, muscular 14 stones slams down into me as I cry out in pain and pleasure, my cock beginning to spurt as he explodes deep and hot inside me, thrusting 4, 5, 6 times before he is done.

"Yes Master! YESSSS" I cry. "Dont stop, please! More!" I beg.

But Im shoved away, complaining, begging and whimpering, as a still-hard cock slithers free of my pussy with a slurp and a "pop" and springs out, sliding against the cheek of my ass and, as I roll around to face my Master, standing proud and grinning in front of me.

Hardly knowing what I am doing, I clamber breathlessly to my knees and grasp the slimy shaft of the tool in my small hand, greedily cramming the head between my shiny, collagen-pumped, crimson lips and sinking the head and half the shaft into my mouth. I frantically bob my head up and down, sucking his cock clean of salty, mushroom-scented cum and the slight, coppery tang of my ass. My pink, pointy tongue slithers up and down and around the shaft, caressing and exploring the outline of every vein and contour as I pump the shaft with my right hand, kneading and cradling his balls with my left. I am spurred on by the sighs and gasps and foul-mouthed exhortations coming from my Masters lips as he encourages me to "fuck that cock with your pretty, little sissy-whores face" and I feel insistent hands, roughly forcing my head up and down and sharp, quick slaps on my face and the side of my head. His cries become louder and deeper in tone, and I begin to feel pride in my ability to bring my Master off so quickly, looking forward to feeling his cock burst in my throat. But as he becomes more vigorous and frantic, thrusting hard into my mouth, his big, greasy tool shoots hard, past my tonsils and deep into my throat. Even breathing deeply through my nose, I begin to gag at the roughness of the invasion, but this contraction just brings about a faster, harder orgasm as he tenses and arches his back, pumping in again as his cock twitches, balls contracting and firing one, two, three power-jets of sizzling-hot cum into my stomach before I wriggle free, coughing as a last ejaculation splashes wet across my lips, chin and onto my chest. At the same time, my choking sends thick, rapidly-cooling cum pumping out of my ass into my skimpy, scarlet panties where it pools momentarily before seeping through the filmy fabric and running down the inside of my thighs, where it is soaks into and runs over my stocking tops.

I gasp, half winded and try to breath through my mouth, knowing that with my nostrils streaming with spunk, Ill only cause myself more discomfort by trying to breath through my nose. I hear my Masters voice, thick, close to my right ear as he caresses the back of my neck in a proprietary way, like Ive been a well behaved dog or something.

"Well done, my eager, cock-loving little slut," he teases triumphantly.

"Only weeks ago you were bitching about how you were a man. How you wouldnt submit and how I couldnt make you" he continues, before he pauses, taking my chin firmly between his fingers and tilting my face upwards to look me straight in the eyes.

" Well, with an appetite for cock like yours, honey, it doesnt look like Ill have to bother making you do anything does it, you little whore?"

I try half-heartedly to deny it as he wipes drops of separating cum from my chin onto his fingers and then into his mouth, laughing at me. I shake my head slightly, mouthing "no" through pouting lips, even as my tongue seeks out his sticky fingers. Knowing that my actions have betrayed my empty gestures, I feel like the cheap, pathetic little faggot that my Master labels me, and then begin to cry silent tears as his laughter becomes louder and more sneering.

"Oh no, bitch," he tells me, "Youve already graduated way past the "make me" stage. You couldnt get enough of me, could you, my cock-hungry little faggot" he taunts, taking a hefty, wet tool and slapping me loudly across the cheek with it. "And now look at you, cum dribbling from your chin, cum streaming from your nostrils, cum running out of your tight, little ass even as its shooting out of your betraying, little cock! You cant get enough of it, slut!"

"I hate you!" I exclaim, angrily.

"Perhaps you do, Pussy," he says in an untroubled voice that oozes confidence " perhaps you do, but not half as much as you hate yourself, and not nearly half so much as you love cock….but dont worry honey, youre going to get plenty of that, so you should be one happy little cum-sponge".

Then my Master stands, pausing only to wipe his wet cock dry in my hair, before tucking his cock back inside his trousers as he walks away from me, leaving me alone, in tears on the floor.

After a few seconds of allowing my indulgence, he tells me casually "shut up crying, you dizzy little bitch".

Then its "stop blubbering, Pussy," in a softer, more conciliatory tone. "Youve come a very long way, my little slut and I can understand that youre a bit confused right now. Weve made fantastic progress together, and Im quite pleased with you. Not only do you look like an available, cock-sucking slut, with your nice, pert titties and your fat, shiny lips, but also youre beginning to act like one, of your own free will! You, slut, just need to start to accept that there are things that you can do nothing to change, and start to manage your situation the best you can".

My tears are now streaming, leaving mascara trails on my cheeks, as I shake my head and try to wipe drying cum from my face.

"Now, seriously honey, stop crying" he says in a more business-like tone.

"Why should I?" I reply in a sulky voice, sniffing.

"Because while you were giving me that very fine blowjob, the clock turned past 6:00 and Im leaving. I dont want to throw you out in the corridor red-eyed, sobbing and half drowned in cum. It might not look good for me in front of the staff, sweetie"

I stand and look in a mirror, humiliated even in the way that he rejects me. I look a mess. I make for the bathroom annexed to his office, only to be told that were in a rush, and that I should do the best I can, as quickly as I can. I take a wet-one from my purse and begin to clean my face of jism and make up. Then, like the little beautician Im fast becoming, I apply translucent foundation, brush on some mascara, dab on a little blusher and stroke on a thick, gleaming coat of crimson lip gloss. I purse my lips to get a good covering, then, seeing you looking at me, and then your watch, I smile, blow a little kiss to me Master with a false smile on my face and turn to join him to leave.

"Forgetting something, my little cock-slut?" he asks in that teasing, half-friendly voice, and I follow his eyes down to the scrap of damp, red mesh on the floor beneath his chair. "I dont mind if you dont want to protect your modesty on the way home, but I do not want you leaving those there for the cleaners" he teases, before heading for the door.

I blush bright red, reaching into my purse for a clean pair.

"No time for that, girl. You should have remembered them in the first place." he tells me, reaching for the handle that leads to the corridor.

"Wait, Master, please!" I squeak in trepidation as I quickly grab my soiled panties and step into them, being sure not to snag them with my sharp, pointy heels before I quickly tie the sides tight around my swelling hips. They are cold and uncomfortable as I pull them up my moist thighs, scooping up some stray cum from my legs and cheeks. As I follow my Master to the now open door, I manage a quick swab of the back of my legs and my butt with another wet-one, throwing it into the bin as I leave. I give him my saucy, coquettish little smile, head on one side as I pass, confidence slightly re-established. My Master immediately knocks it out of me, smiling and patting me proprietarily on my damp ass before pulling his hand away in faux-disgust and giving it to me to lick clean of spunk. I blush again, feeling humiliated and cheap once more as I hear my Master whisper behind me

"Do you think that was yours, or mine, my dirty little slut?"

We walk together down the corridor, my heels clip-clopping on the hard floor, out into the car park. Im hoping for a lift home, knowing that theres a fair amount of leakage still likely to come out of my ass, and these already saturated panties will do nothing to soak up the leak. With a skirt as short as mine, its too much to expect that nobodys going to see that big, dark, damp patch in the ass of my red-flag panties and maybe even see the drying, white stains in rings around the patch. Added to that, I can now feel the throbbing of dark bruises forming around the stinging red welts on my ass. It wont take a genius to work out what Ive been up to, especially as the route Im ordered to take home takes me through the busy mall and up a couple of steep escalators.

As we approach his car, I summon up some courage and, adopting my sweetest voice and most innocent face ask

"Any chance of a lift home, Master, please?"

My heart sinks as I see the sly grin on his face.

"No chance, slut." he answers, giving me a dirty look up and down. "Id never live it down at the gym or the sailing club if anybody saw me with a cheap, seat-wetting, little street-walker like you in the passenger seat". And with that cutting remark, and a snort of derision, he reaches down and opens up his car, stopping only to say

"Ill see you at your place later; around 7:30. Youll find an outfit there that I want you to wear to go out in tonight. Make sure you go home via the mall, slut. I want everybody to see that fine, cum-filled ass of yours. And remember, you never know when youre being watched, so walk nice."

And with that chilling reminder of my position of subservience, he starts the car and drives away, leaving me alone, facing a two-mile walk across town in my 4 inch-heeled, ankle strap stilettos. The heat has built during the afternoon and I know its going to be an unpleasant journey. Even as I take my first steps, remembering to bring each foot around in an arc to land on an imaginary tightrope as Ive been trained, so that my still-sore ass rolls provocatively, I clench my ring to stop more cum leaking into my greasy cleft and sodden panties. Its a battle that I wont be able to win. I know that at some stage, Ill have to relax and it will probably come gushing out. I face a choice; one of the very few that I can take for myself these days and I struggle to focus my brain on making a decision. "Its so hard" I think to myself "now that theyre all made for me".

I know that if I give-up the fight and relax now, letting the cold, wet, shit-flecked cargo out of my pussy before I get to town, theres a good chance that in this heat Ill be dry before I get to the mall, meaning less chance of somebody noticing. On the other hand, that means consciously allowing the cum to run out and pool in my panties. My own decision to surrender, knowing that in these tiny mesh panties, a fair amount will run straight through and down my buttocks, onto my thighs, on public display should anybody get close enough to see. I know that even if I fight, Ill fail anyway, and the same thing will happen, probably as soon as I start up the steps at the mall. The irony of the decision is not lost on me. I recognise the decision as a microcosm of my current lifestyle. Should I submit to and in some small way control and minimize the humiliation and hurt by complying and trying to make the best of things? Or should I put up a futile fight, knowing that my humiliation and suffering will ultimately be much, much worse. Its a fight that I will eventually lose, but I could try to retain the smallest modicum of pride.

My ass is already feeling greasier and Im struggling to hold on, particularly as the way Im made to walk stretches my muscles much further than Id like. My ass is twitching and, with a sinking feeling, I realize that fighting will be more uncomfortable in the short term and much more embarrassing and painful in the long term if I try to hold on. I wait until a couple of guys have passed me by, knowing even before I turn to smile at them that theyll have spun round to check out my ass. Once theyre a distance off, and no longer grinning and whistling, I turn back and, taking a deep breath, relax my pussy. I feel immediate relief as the cum streams from me. Then I feel the cold wetness, hear a new squelching sound with every step, and begin to walk more quickly, hoping that this will increase the airflow and dry me more quickly. I feel cheap, degraded, pathetic and dirty, particularly as Ive been trained not to wipe the stream from the back of my all-to-visible thighs. But I dont feel as bad as I would have done if Id had to do this a week or so back, when I first started at my Masters company. I realize that this is a big moment in my new life. Im finally starting to accept, and live with, my new situation. Does it feel that bad? No. It feels a lot better than the last time I fought and found my tits clamped, my ass whipped and my little clit and balls wired-up to a generator. I now recognise a new fight; the fight to not upset my owner, to avoid having to endure such horrible torture, whatever it takes.

With this resolve to co-operate in mind, I straighten up, focus on my posture and form as I sashay down the pavement, and head for home, ready to be as accommodating as I possibly can when I get there, and wondering what my new outfit is like and what plans Master has in store for me tonight.

 


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