With sincere apologies to all those who have been hanging out for the latest instalment of this kinky tale, welcome to the sixth chapter. if you have any comments or reactions, PLEASE don't hesitate to email me, as I adore hearing from anyone who shares my love of crossdressing, writing or both. And do think about donating to help support this wonderful site.
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MY NEW CAREER - PART 6
Tap, tap, tap, tap ... Irritated, I looked around to find the source of the sound that had broken into my thoughts. Glancing down, I realised I was drumming my fingers on the wooden arm of the chair in which I was sitting. Rolling my eyes, I inspected my bright red nails to ensure there was no damage - another new aspect of my life I could never have imagined - then reached forward to take a calming sip of the orange juice Grace had given me after she'd shown me into the waiting room.
In the graceful way that had been drummed into me by my trainers, I uncrossed and then recrossed my legs, enjoying as always the frisson of nylon against nylon and pulling down the top of my short, satin skirt so that it at least partially covered the tops of my fishnet stockings
Today I was dressed as a French maid. The look was a classic one - the black bodice trimmed with white lace, the skirt likewise and sitting on top of a frothy white petticoat, the white pinafore, a black choker (again with a white lace trim) ... and to top it off, a white lace headpiece attached to a headband. When I'd checked out the reflection in the dressing room mirror, it was impossible not to laugh with delight, I looked so fucking hot ...
The smile that this recollection had prompted quickly faded, however, as my thoughts returned to the previous night's events. I simply could not figure out how I felt about what had happened with Grace ... or how I ought to feel.
On the one hand, the exhilarating glow of our lovemaking still lingered, as did the sheer wonder of finding myself in bed with someone as beautiful and sexy as the Ceder College's receptionist. But neither could I banish the thought of the small but functioning cock she carried between her exquisite legs, an organ that I had fondled and stroked and crammed into my mouth. Nor the taste and feel of the creamy load she had deposited down my throat ... and not just once.
As we had stumbled out of bed, threw our clothes on and began the walk into the city, I had tried to talk to Grace about my feelings. But she was having none of it, playfully deflecting every attempt to discuss the significance of what we had just done. The Cheshire Cat grin that seemed to have permanently affixed itself to her pretty face since we woke up suggested she saw no complications at all with the way our relationship had changed.
Even when I reminded her that we should probably not be seen arriving together at the College, her expression was still happy as she unlinked her arm from mine, gave me a peck on the cheek and scurried away to head around the block, pausing only to call back, "We'll talk after work, okay?"
By the time I saw her later at the College, she was all cool efficiency again. And yet her eyes seemed to sparkle at me, sending the message that whatever we might need to do while at work to conceal our feelings, she was mine ...
If only it were that simple, I thought. I was painfully aware that my life was not my own to control. It had been plucked from me on the day I had first come here, when I had been drugged, tricked and then blackmailed into the bizarre transformation that had seen the ineffective and unsuccessful Martin Riley become the sexy stripper Katy.
Oh, there were chains before all right, those of poverty and mediocrity and lack of assertion. But I could dream of throwing them off. Now, for all the perverse pride I could take in the way I looked, for all the increasing ease I felt and displayed in my female guise, I was under no illusion about who determined my future ...
Right on cue, the voice cut through my reverie. "Katy - in here. Now." The disembodied summons, amplified by the wall,speaker from which it issued, had me quickly and obediently on my feet. I crossed the room, tapped respectfully on the door, then entered the room beyond.
Mr Everett watched me walk carefully across his office, taking care not to snag my heels in the plush pile of the luxurious carpet. His handsome gaze ranged up and down my body, an inspection that a few weeks ago would have made me blush furiously, but now was second nature after all the ogling I got at Club Angel.
"Mmmm", he said appreciatively, "you move now almost as sexily as you look. Almost ..." As I came to a halt in front of his desk, hands clasped demurely in front of me, he gestured at a file he seemed to have been reading.
"We're very happy with your progress, you know. Especially, your, ah, latest exploits ..." A smile twitched the corner of his lips and I felt a pit open up in my stomach. "Who'd have thought you'd be quite so willing to open that pretty mouth of yours? And with our lovely receptionist, no less ..."
As I opened my mouth to speak, his curt gesture cut me off. "We don't mind what you get up to in your time off. Or rather", he amended, "we do - but we were happy to let you off the leash a little bit. So long as we're clear it's not going to happen again. Because I'm sure you wouldn't want me to ask my sister to take you and Grace to task, would you?"
The thought of the domineering Kristen Everett administering her sadistic brand of punishment was enough to bring beads of sweat to my brow. "No sir", I answered, head bowed.
"Good", he responded, "if you want any fun, you'll have to find it with that sugar daddy landlord of yours." He grinned at my obvious discomfort and I reflected, not for the first time since coming to the College, that I should never underestimate my captors' power to know and control everything about my new life. So they were aware of my live-in arrangement with Mr Stokes as well ...
"Not", the principal continued in his well-modulated voice, "that you can't have fun here as well. In fact i just know you're going to enjoy your next assignment. Come with me."
I followed him as he led me out of a second door in his office and into the corridor outside. Waiting for us was a petite and attractive redhead, dressed in a costume identical to mine. She fell into step beside me as I set off behind Mr Everett.
"This is Scarlett", he said, not looking round but jerking his head briefly at my companion. "You'll be helping her to attend to some of our most valuable clients at a special function. Think of it as the next stage in your, ah, education ..."
I shook my head, still reeling from the revelation that my night of passion with Grace had been ... what, observed? Recorded? Or had Grace just told them ...?
Somehow, I found my voice. "Sir", I began, fighting to control the tremor, "what sort of 'attending' will we be doing, exactly?"
Mr Everett laughed. "You'll find out soon enough. Just take your lead from Scarlett. But be aware, you'll need to beat her."
"Beat her?" I replied. "Beat her with what?" I glanced sideways at the other maid, but rather than the look of alarm I was expecting to find, saw only a smirk on her face.
This time the principal stopped and turned around. Smiling, he stroked me softly under the chin, as I fought the urge to flinch. "Oh Katy, you're priceless, you know that? Beat her with what! You're obviously spending too much time with my sister - though I'm sure she wouldn't see it that way. I mean, you'll need to do better than her - if you want to move on, that is."
Something in his tone deterred me from asking any more questions, much as I wanted to. Wordlessly, he turned and set off again, leading us into another of the long tunnels that seemed to link the office tower in the bowels of which the College was located with several buildings around it.
But this time it was not Club Angel that was our destination - or at least, not a part of it I'd ever seen before. An anteroom led us into a long, well furnished room, dominated by a table that had evidently been set for lunch. "Right", said Mr Everett, "I'll leave you here. The guests should be along shortly. Be sure to take good care of them!"
With that he left by the way he had led us in. I turned nervously to Scarlett, who,was eyeing me appreciatively. Before I could say anything, she reached up and put a well manicured finger on my lips. "Best not to, okay?" She patted me on the rump. "You're gorgeous, you know that? I can see I'm going to have my work cut out ... Now, come and help me get the drinks tray ready."
She caressed my bottom lightly, sliding her hand down to the bare flesh at the back of my thigh. I shivered at the contact and felt my imprisoned manhood stir in its satin sheath. But before I could react further she was striding away to what turned out to be a well stocked drinks cabinet.
We had just finished pouring out a selection of wines and beer when a door opened at the far end of the dining room and a dozen or so men sauntered into the room. They were all well dressed, of varying ages. One or two seemed a little nervous, glancing furtively at Scarlett and me, but then looking away rather than make eye contact. But most appeared confident and relaxed, talking easily and laughing as we moved among them to offer drinks.
After a few minutes a gong sounded and they sat down at the table. Two more maids, once again dressed in the same outfit, appeared and began to serve food. But where they just as quickly disappeared again, Scarlett and I remained in the room, topping up drinks and moving around the table to chat with the guests.
As I had been trained, I spoke lightly and coquettishly, asking no personal questions but keeping the conversation light and airy. One or two of the diners invited me to sit on their laps. Noting that Scarlett had already done exactly that with some of the other guests I complied, perching lightly on their thighs and allowing their hands to roam over my torso and legs.
I had endured a lot of this treatment over the preceding weeks and had occasionally found myself responding. But this time was different. Every caress seemed to heighten my arousal and I felt a strange heat, which only grew when I looked over at my beautiful co-worker and received a smile and a wink in return.
When a powerfully built man pulled me right into his lap, and ground his groin against my pantied bottom, the large bulge I could feel beneath me made my cock grow and strain against the fabric that concealed it, so much so that I feared it would tear free. Not wanting to reveal my little (or now not-so-little) secret, I squirmed to get away, but was held fast in place. My legs were prised open and a hand crept under my skirt and began to work its way up my thigh, kneading and caressing as it went.
A deep, sardonic voice behind me murmured, "Now, fair maid, what do we have here?" The man to his right gave a laugh and said "Careful Antony, you know what this place is like, there could be anything inside those panties! Besides, main course is here ..."
For a second or two the hand probed a little further, then with little apparent effort the powerful man lifted me off his lap, set me down on the ground and turned me round to face him. I looked down into a dark, saturnine face, striking rather than handsome, but with a compelling gaze from his deep-set eyes. It was hard to place his age.
He lifted an eyebrow. "What's your name, maid?" My cock seemed to stiffen even more as I answered: "Sir, it's Katy." He stared up at me intently, then said: "Katy, eh? Well, you be sure to come to me first, Katy, you understand?" I didn't, but I nodded anyway, throwing in a curtsey for good measure, which elicited another chuckle from the man's companion. I moved away as one of the serving maids brought Antony his meal - was that his first or last name, I wondered? - and resumed my circuit around the table.
For the next half an hour or so I was mostly confined to topping up drinks while the diners ate. But then came a change in the music, which had been piped into the room by hidden speakers. Cool jazz gave way to a techno beat and the volume increased appreciably.
I looked over at Scarlett. She grinned back at me. "Time for their dessert!" She positioned herself between two of the guests and, with their willing assistance, clambered up on to the table. As the diners applauded, she beckoned me to join her - which I did, as gracefully as I could.
The music level increased another few notches as, following my co-worker's lead, I began to dance. Even with all my recent training, the combination of high heels and a shifting tablecloth made it hard to move my feet. So I concentrated on bumping, grinding and writhing, running my hands over my body as I made eye contact with the hungry faces staring up at me.
Suddenly, I felt Scarlett press up against me from behind. As I slowed my gyrations she maintained the contact, so that our bodies moved together. I thrilled to her touch as I felt her hands roam over my torso before settling between my legs, pressing and rubbing the carefully concealed mound. Her breath was hot on my neck as she nuzzled and kissed it. The semi-erection I had been carrying right through the meal burst once more into full bloom under the pressure of her attention, reviving my fear that it would escape its confinement.
Turning me round, she pulled me into an embrace, her lips crushing mine, her tongue wickedly probing. I should have been surprised, might have resisted ... but I didn't. I was so horny it hurt and the response was purely automatic. Moaning, I returned her kisses, reaching both hands round to grab her behind and pull her hard against me.
With her lips still locked together I felt Scarlett grab my hands and pull them up to her breasts, which I groped and fondled through the satin that covered them. Then, barely conscious of what I was doing, I was yanking the bodice down to free them and lowering my mouth to feast. Her boobs were nothing like as big as Grace's, indeed they barely warranted the term ... but the nipples were long and rock hard under my tongue, and Scarlett's gasps of pleasure were all the encouragement I needed.
Once again, she grabbed one of my hands, this time guiding it down under her skirt and into her panties, Part of me wondered what I would find there ... but after last night, it didn't really seem to matter. It was with interest rather than surprise or disappointment that my fingers slid into the cleft of what was unmistakeably a woman's pussy ... and one that was dripping wet. I was rewarded with more gasps as I probed it and found the sweet bud of her clitoris.
Breaking the embrace, Scarlett bent down and tugged her panties to her ankles, then knelt on the table between my legs. Before I could say a word she had reached under my skirt and, with practised ease, liberated my straining member. The protest died on my lips as she plunged it into her mouth and began to fellate me. Trembling with lust, I reached down and caressed the auburn curls on her head as it bobbed back and forth between my splayed, fishnet-covered legs.
It was only then that I remembered where we were. The music was still pounding, but there was no hint of the cheering or applause I might have expected from previous sessions at the Club. A glance down and around me quickly showed why. Each of the dinner guests were leaning back in their chairs, entranced at the show we were putting on for them. And every single one of them had their cock out, masturbating ...
Some were gently stroking, others tugging more urgently. I should have been shocked, repelled even. But for no reason I could explain the sight made me even hornier. Boldly, I caught the eye of those closest to me and licked my lips suggestively, prompting lustful moans in response that I could hear even over the music.
Releasing my cock from her mouth, Scarlett surged upright, kissed me again and then whispered an urgent command in my ear. Before waiting for a response she turned round, bent forward and thrust her rump in the air. I didn't need a second invitation. Of course I was going to fuck her! Shuffling forward and grabbing her hips, I positioned my rigid shaft against her wet and willing gash and slid inside.
There was nothing subtle or tender about the next few minutes, just plain and brutal thrusting. As I pounded her from behind she stuffed a hand between her legs and frantically rubbed her clit. Her screaming orgasm came just seconds before my own. She was still shuddering when I spurted deep inside of her.
For a moment I held that position, then with a deep sigh slid out. Legs trembling from the effort, and the aftershocks of my climax, I slumped down to my knees. I took a few deep breaths, then looked up to find Scarlett sliding herself off the table, my cum dripping unheeded out of her pussy to splatter the tablecloth. She caught my eye and grinned. "Fun's over babe, time for the competition!"
Kneeling down, she bent her head into the lap of one of the guests and began greedily sucking on his exposed cock. With her free hand she beckoned to the man beside him, who shuffled his chair closer to her in response. As her questing palm found his appendage, she began to pump it, all the while maintaining her oral ministrations to the first diner.
Genuinely shocked now, I looked around. Every other man at the table was calling to me, beckoning to come over. All except one. The man called Antony was simply staring at me, eyebrows arched quizzically. As if in a daze I crawled over to him and half-fell, half-slid off the table. I looked down at his lap to see a massive cock, every bit as thick as Mr Stokes', but considerably longer, which he was gently massaging.
"What do you think Katy, reckon you can fit that inside your pretty mouth?" His tone was amused, but the look was cool and brooked no objection. Once again, I felt an improbable surge of lust. It was with desire, not resignation, that I knelt between his legs and lowered my head to his groin.
Oh my god, it was huge! Yet I'd had even bigger dildos stuffed in my mouth, courtesy of Miss Everett's twisted imagination and large toy collection. Taking a deep breath I opened my jaw as wide as I could, then carefully slid the shaft into my mouth and down my throat. I couldn't reach the bottom, the base was too thick, but I held it for as long as I could, then carefully withdrew, leaving it coated in my saliva.
Looking up, I smiled. "Is that what you wanted, sir?" I was rewarded with a wolffish smile. "That and more, Katy, that and more ..." A firm hand guided my head back to his cock and I began to suck for all I was worth, not going too deep but working hard on the engorged glans.
As I pushed my head up and down, holding my lips as firmly as I could to maintain maximum suction, I could sense the building tension in the man I was servicing. The pressure of his hand on the top of my head began to grow, and he started to thrust up in time with my downward plunges.
I was just starting to struggle for breath, wondering if I could possibly keep up the tempo I had set, when a kind of growl began deep in his belly. The sound escalated into a moan and the thrusting became more frantic.
I was on the verge of choking when, with a roar, Antony came. But not, as I had anticipated, into my mouth. At the last second, he yanked his cock back and aimed it at me, like a massive cannon waiting to be fired. My head was held irresistibly in place as he shot jet after jet of spunk into my face. I closed my eyes reflexively as he coated me in his pleasure, feeling the hot splashes on my forehead, cheeks, nose, eyelids ... just about everywhere, it seemed.
Only my mouth was spared, and then only for a few seconds. I felt his weapon press insistently against my lips, which like my eyes had clamped shut of their own volition. His voice seemed to come from a long way off. "Clean it."
There was no thought of resistance. My lips parted as I accepted the enormous head back into my compliant mouth, sucking and licking to free the last drops of cum. For some reason I did not swallow the residue, but collected it on my tongue, as I had seen porn actresses do. When I was finished I opened my mouth, drew back and then held out my tongue for inspection, before gulping down what I had collected. As the salty fluid slipped down my throat I was rewarded with a chuckle and an approving "Good girl!"
It was only then that I straightened up and attempted to open my eyes, blinking them repeatedly to clear the viscous fluid that clogged my eyelashes. As my vision cleared my first sight was of Antony leaning back in his chair, his huge cock still standing proud from his unzipped pants, a broad smile on his face. He looked every bit the cat who had got the cream - or in this case, given it.
As awareness returned, I became conscious of several things, more or less simultaneously. I was gasping for breath, cum was dripping from my chin, my own cock was once more rock hard ... and on each side of me stood men with raging erections, waiting to be serviced.
A loud cheer caused me to swivel my head and look over to the other side of the table, where a guest had evidently just finished emptying his balls all over Scarlett. As if aware of my gaze, she turned to look at me. Her face and hair were plastered with cum, but they could not hide her triumphant smile. She briefly held up her left hand, extending three fingers, then quickly transferred her attention to the cock that was firmly grasped in her right, pulling its owner forward until she could cover it with her mouth.
The penny dropped. So that's what the competition was ...
Heedless of the jizm that still coated my face and fell slowly onto my costume, I shuffled backwards away from Antony to make some room and then beckoned the other men. A little voice in my head was wailing with shame and revulsion, but I had no time for it. Positioning one man either side of me where I knelt, I began wanking their cocks, alternately jamming them into my mouth. They were nothing like as big as Antony's and slid easily between my cum-coated lips.
After a few minutes of this I was interrupted by a soft touch on my chest. I focused my eyes on the figure kneeling in front of me, though my hands continued their work. It was one of the nervous-looking guests I'd noticed earlier. "Yes, sir", I said, trying to still my heavy breathing, "what is it?"
He looked abashed, but then seemed to reach a decision. "Um, miss, do you mind if I, er ...?" He glanced down, then back up at me. My incomprehension must have been obvious, because he reached down and took hold of my erect shaft, which he gently began to stroke. Then he looked at me again, lifting his eyebrows.
Utterly taken aback, I stared at him and shook my head in sheer disbelief. His face seemed to crumple and he pulled his hand away. "No, wait", I said hurriedly, "I didn't mean ... Look, knock yourself out, okay?"
I turned back to the cock to my left and engulfed it with my mouth, all the while jerking the one in my right. And as I felt my own boner first caressed and then licked, I heard another cheer from behind me ...
Much later that day, I completed the slow walk home from the train station. It had not been a pleasant ride. Try as I might, I could not rid my mind of the image that had greeted me when I returned to my dressing room after the lunch. Where the guests had been brought warm towels to clean up, Scarlett had made it clear that we were expected to parade around to show off the fruits of our labour.
It was she who got the bulk of the acclaim, of course, having comfortably outpaced me in milking the clients - though I was congratulated for doing as well as five (or six, counting the second load that Antony had dumped onto the top of my head just before the gong went to end the festivities). As Mr Everett put it, I had done "wonderfully well for a novice".
That was some comfort, I suppose, and even more so the broad hint that I had once again been drugged - or as the principal put it, "given a little chemical encouragement". I could tell myself that whatever had been slipped into my orange juice was responsible for my undeniably slutty behaviour, for my eagerness to suck and wank a group of strange men - or indeed any men at all.
But that didn't alter the implications of the cum-splattered visage staring back at me from the mirror, or the sticky, crusted uniform that I had peeled off before getting in the shower, or the taste of semen in my mouth - some of it licked off Scarlett and then swapped between our mouths as we performed one more perverted act to farewell our admiring customers ...
I had not just been feminised, but utterly degraded ... and I couldn't be sure that I was an entirely unwilling participant in either process. I had become accustomed not merely to dressing as a girl, but to using the new looks I had been given to tease and seduce members of my own sex - or of what used to be my sex ...
And if I had thought it was bad enough to do that simply by dancing and posing, that had been taken to a whole new level today - with the promise of more to come. Literally, no doubt, as well as figuratively ...
And then to top all that off, there was Grace. We had made such a connection last night - and not just a physical one, I was sure of it. Yet now I had not only been warned off seeing her again, but left wondering how much she really knew about what the College was doing to me. It was she who had given me the only drink I had consumed today - apart, I reflected bitterly, from the accumulated fluids of several men. Had she known there was something in it? Did she tell Mr Everett about our ... affair? Was her approach to me all a pretence in the first place?
I found it hard to believe this last was true, especially after seeing the hurt expression on her face when I had hurried out of the College without making any attempt to talk to her. She couldn't be that good an actress ... could she?
The fact was though that, regardless of the truth of her role, I had just lost the one friend I had developed at the College, the only person I could talk to about what went on there. And someone who, if my supposition was right, must have gone through a similar transformation to the one I was experiencing.
It was with these dark thoughts swirling in my head that I turned the key and entered the ground floor apartment that had become my home. As I entered the hall I heard the creak of leather and wood as Mr Stokes levered his heavy body off the sofa. He came rushing out to meet me, his face a mask of anxiety.
"Oh Katy, thank goodness you're here", he babbled, placing his hands lightly on my shoulders. "Where have you been? I was so worried! I kept thinking I should try to call you, only I don't know where you work, and ..." He trailed off, noticing my stricken expression. "What is it, dear?"
Oh my god, I had totally forgotten that I hadn't come home last night! While I was pleasuring myself with Grace, my landlord must have been lying awake wondering where I was and whether something had happened to me. And I hadn't thought to call, even this morning, when it would have been so easy to borrow Grace's phone ... He had been so good to me, in his way, and this was how I repaid him!
It was the last straw - and I burst into tears. In a flash he had gathered me into his strong arms, cushioning my head against his broad chest as he stroked my face, making soothing noises.
"I am s-s-so s-sorry", I managed to get out between sobs, "I've been ... so silly and selfish ..."
"There, there", he said, gently patting my head, "don't worry about it, you're home safe and sound, that's the main thing, alright sweetie?" As my weeping subsided, he held me out in front of him and looked down into my tear-streaked face. Even in my heels, I was still a good few inches shorter than him.
"I don't suppose there's anything you can tell me about what happened?" I shook my head mutely. The wry smile on his lined face was so understanding that it prompted a further flood of tears. Once again, I was pulled into a hug. This time he made no attempt to talk, just rocked me gently as I cried myself out.
After a few minutes of silence he said softly: "I'll go and make you a nice hot drink, okay? And then perhaps a little bit of dinner - if you're hungry?" I nodded gratefully, but made no move to break the embrace, just stood there with my head comfortably nestled on his shoulder. He understood, and for a while longer we maintained that position as I savoured the feeling, no matter how transitory, of being safe from all my troubles ...
Later that night, as we lay together in bed, two thoughts were uppermost in my mind. One was that I did not normally weep in the way I had done earlier in the evening - or at least not since I was much younger and my pet cat had died. True, I had been under extraordinary stress. But I wondered whether the "vitamins" I had been taking might have had something to do with it - and speculated darkly about any other changes the College might be making, without my knowledge or consent.
But the dominant feeling was one of relief - that for all the terrible things going on, and for all my self-disgust at not just failing to resist, but actually seeming to enjoy much of what was being done to me, I at least had one person who seemed to care.
Impulsively, I rolled over and kissed Graeme on the mouth, softly and tenderly. Even in the dim light, I could see his surprise. It was not like me to initiate any kind of physical contact, let alone a kiss. "What was that for?"
I answered his murmured question with another kiss. "For looking after me" I said in a husky voice, running my free hand over his naked torso and then snaking down to find the lump in the loose boxer shorts he habitually slept in. It stirred under my touch.
For a minute I paused, then smiled to myself. It was not as if I didn't know what to do ... Sweeping the sheets back I shimmied down the bed until I found his groin. Unfurling the stiffening cock, and freeing it from the silky material that covered it, I slowly slid it into my mouth ...
(To be continued)