My New Career

Welcome to the seventh chapter of this story of a job application gone disastrously wrong (or as I prefer to see it, right). if you have any comments or reactions, please feel free to email me. And do think about donating to help support this wonderful site.

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MY NEW CAREER - PART 7

"So if you could choose any of the girls here, who would it be?"

"Any of them? And I can do whatever I like with them?"

"Total freedom, whatever floats your boat. Put 'em in any uniform you like, fr'instance."

"And no time limit?"

"No time limit - well, you know, within reason. But could be all day, if your stamina held out."

"Hmmm, tough choice ... Ivanka, maybe? Miranda? Or perhaps Scarlett - no wait, she's gone, hasn't she? Left last month. Soooo ... I'm going to say - Taylor!"

"Taylor ... hey, great choice. The blonde bombshell, looks great in anything - and even better in nothing at all ... But listen, you wouldn't think about picking Katy?"

"Katy? You're kidding, aren't you?"

"What's wrong with Katy?"

"What's wrong? Where do you want me to start? No boobs, for a start. I mean, what's the point of having a face and body that good if you don't have a rack to match? And her cock is far too small. Plus she's so insecure, she thinks people are talking about her all the time ..."

I opened my eyes. "You do realise I'm awake, right?"

Lily chuckled. "Oh my god, you mean you heard all that? What will you think of us?" She resumed work on my nails. "We're just having a laugh, babe. Give me the choice of any girl in the College to dress and make up, you're top of my list. And you know it ..."

"Hmmm, I'm not so sure", said Daniel from behind me. I felt rather than saw him lift some of the strands of my long, raven tresses and examine them critically. "I mean, look at the state of this hair. I don't know what you've been doing it with, darling ... or rather I do. It's all that creamy 'conditioner' the men have been giving you at the Club, isn't it?"

He gave a dirty laugh and resumed his work with the brush. I blushed furiously and protested my case.

"No fair - it's not as if I ask them to shoot their load all over me. Except maybe I lend a hand here or there. And like, you know, the odd blowjob ..."

"Yes", said Lily drily, "I've heard your blowjobs are pretty odd ..."

This time I joined in the laughter. Not much about working and training at Ceder College was comfortable, but I never felt more at ease than when I was in the company of the beauticians. Apart from the fabulous looks they gave me, they seemed to be able to make light of even the most challenging aspects of what went on here. They knew that I was virtually a captive, being forced to assume a different gender and perform sex acts for money. But that didn't mean they couldn't brighten up my day.

And the fact was that if I didn't think too hard about my situation, it could have been a lot worse. I had come to love the clothes they dressed me in, the wonderful things they did to my hair, the femininity of my appearance.

And as for the dancing at the strip club, and the three times now I'd been required to give handjobs and blowjobs to a group of "special" clients ... well, that too could be endured, especially with the chemical cocktail that helped heighten my arousal and lessen my inhibitions. On the first occasion the drugs had been slipped into my drink. The second and third times, I had been given the choice by the principal, Mr Everett. I'd opted to take them because ... well, if nothing else, it helped me excuse my own behaviour. I really didn't want to think about doing all those things voluntarily ...

Not that it was just the lunches. Since my "initiation" I'd been given the option of offering "hand relief" (though nothing more) as part of the services available to customers at Club Angel who paid for a private dance. I was told it was up to me whether I did this, though the extra money earned would go into the account that was - or so I was assured - set aside for my future use.

I had been wary of whether there was a real choice here or not, given the constant threat that if I didn't do as I was told, compromising photos of me (in the male guise I could barely now remember) appearing to have sex with an underaged schoolboy would be released on the Internet. Not to mention the control I'd signed away over my finances ...

But in any case, I'd pretty much got used to the idea of wanking off men by now. Besides, many of the clients who wanted to buy some private time with me had become regulars, who I'd grown to know and - in a strange way - trust. There were a couple of older guys in particular that I positively enjoyed seeing, they were so sweet in the way they complimented my appearance, so grateful for the chance to fondle my body, so awed by my willingness to handle their scrawny members and tug them to release.

And speaking of old guys ... My live-in relationship with Mr Stokes had blossomed even further since the night I'd first sucked him off. Our sex life had certainly gone to a new level. I couldn't believe how horny he was, or how much staying power he had when I used my newfound skills with hand and mouth and tongue on his thick cock. But the real revelation was his willingness to give me pleasure as well.

He insisted that it wasn't fair that he was the only one that got to come, especially when I confessed that playing with his cock often made me hard. There was no suggestion of him putting his mouth anywhere near my groin. He loved ladyboys, but not that much, or at least not in that way. He was entirely active and dominant in his desires. But he was more than happy to put his big hand into my panties and toss me off. And when I insisted on licking my own cream off his fingers and palm, that just aroused him even more.

There were times when I even fantasised about being fucked by him, though always with a tinge of shame and guilt that I should even contemplate such an act - not to say astonishment, for someone still so firmly attracted to women. But even if he had asked to do that, something that would now seem so out of character with his gentle and courteous treatment of me, I would have said no. It was the College that decided what I could and couldn't do ...

And there was the biggest barrier that remained between us. I had thought so many times about telling Graeme the story of how his pathetic male tenant had been transformed into the sexy girlfriend who now lived with him. But there were two impenetrable obstacles. The fear of what the College would do to me if my indiscretion was uncovered. And the even greater worry that he would want nothing further to do with me if he knew how I was spending my time here - and just how many other cocks I was arousing, fondling and servicing ...

"All done Katy", called Daniel in a singsong voice that cur through my reverie. I stood up, balancing without conscious effort on the six-inch heels I now routinely wore, and inspected myself in the mirror. My hair fell in long wavy curls to my bare shoulders, topped off by the wispy white lace cap. I looked at each of the beauticians in turn. We could all guess what my assignment was today, given the maid's uniform and the instruction to report to the principal's office just before lunchtime.

"Wish me luck, okay?" I said. Lily straightened and leant in to give me a peck on the cheek. "You don't need it, sweetie", she responded, smiling. "They'll love you, I know they will."

"Well yeah", said Daniel, "but that's what I'm worried about - them loving her all over this hair I've just spent half an hour on ..." He gave me a brief hug and then gestured to the clock on the wall. "Go on, you don't want to be late."

I was still a little early when I reported to the principal's office, to be greeted by the new receptionist, Nikki. I had not seen Grace since the day after what had turned out to be my one-night stand with her. My attempts to elcit any information about her whereabouts had, as usual, failed miserably. I had been worrying about what might have happened to her - though my concern was tempered by a lingering doubt as to whether she had been acting on the College's instructions, or had at least told her bosses about us.

Nikki, a willowy blonde who had been dancing in the Club before being brought in to replace Grace, handed me the now customary glass of organs juice. She winked as I took it and I smiled in return, but didn't say anything. The rule at the College was simple - don't speak unless you're spoken to.

When the summons came, I was surprised to find Kristin Everett in the principal's office, rather than her brother Gordon. Although they shared the role, I had seen little of Miss Everett recently. Our weekly "play" sessions seemed to have disappeared from my regular schedule, something I was not sorry about. Aside from the other forms of punishment or humiliation I had been compelled either to experience or to watch being visited on other students, I was especially glad for a respite from the heroically sized butt plugs she had often insisted on drilling into my rear.

"Katy", she said in a brittle voice, pointing to a spot in front of her desk at which I duly stood, "I assume you know what you're in for today?" I nodded obediently. "Yes, ma'am."

Her face twisted into an unsettling smile. "Jolly good - though there'll be at least one thing different. Up to now, you've been working with - and competing against - some of our more, ah, experienced young ladies. And doing very well, I hear. But today, you're the veteran. You'll be up against someone who's a newbie to these sessions - well, kind of, at any rate."

She lowered her head slightly and peered up at me intently over her gold-framed spectacles. "Which means, you'll need to lead the way. It's the usual thing - serve drinks, some chit-chat with the guests, then a performance on the table that will include you fucking her - but you both have to come, right?"

At my dutiful nod, she continued. "And then it's time for you both to play with the guests - and let them play with you. If you can make more of them come than the other girl, you win - and it will be the last time you have to appear at one of these shows, okay?"

"Yes ma'am", I answered crisply. I was relieved to get confirmation of something that I had previously only suspected - that if I could only reap more orgasms than my rival, I would not have to go through this demeaning experience again. As I followed Miss Everett out of the office, I was already pumping myself up. The men at today's lunch wouldn't know what had hit them, I vowed.

But all my positive thinking came to a shuddering halt when I saw who was waiting for us outside, dressed in exactly the same French maid's costume. It was Grace.

She glanced briefly at me, her lovely eyes widening with evident surprise, then quickly looked down again. As Miss Everett headed off down the corridor, we scurried to catch up. The principal's voice dripped with amusement as she spoke over her shoulder.

"Bet you've been wondering where your playmate had got to, eh Katy? Well, she's been undergoing a little ... re-education. This'll be her last day here in fact, before we send her off to one of our other facilities. But we couldn't resist getting the two of you back for one last reunion. Not after seeing how hot you were together. That video's been on high rotation in the Everett household, I can tell you!"

At the mention of a video, I couldn't help but look sideways at Grace - to find her doing the same to me. The barely controlled shock on her face exactly mirrored my own, I was sure. I opened my mouth to protest, but fortunately for me, perhaps, Miss Everett was still talking.

"Now Grace, I do hope that you're still going to be able to open your legs for the lovely Katy. I mean, just because she cost you your cushy job doesn't mean that you should hold it against her ... although I'm sure our guests today will be wanting you to do just that, ha, ha!"

Tightening my lips, I resolved not to respond - it would only make things worse. I did not look at Grace again until we had been left alone in the dining room. When I did, I saw her frown and give a barely perceptible shake of the head. There seemed zero chance of having any conversation in here that would not be overheard - or at least not right now. Sighing inwardly, I said out loud: "Cmon, lets gets some drinks out", and busied myself loading up a tray.

When the guests arrived, there were two surprises. One was Miss Everett leading them in. But it was the other that really stopped me in my tracks.

All the guests today were women.

There were both similarities and differences to the groups I'd seen at the earlier lunches. Like their male counterparts, the diners were crisply dressed in business clothes, with the occasional skirt, high heels or crimson lipstick the only obvious concessions to femininity. They projected confidence and power, in the way they carried themselves and spoke. Their ages ranged from perhaps thirty all the way up to sixty or seventy year olds.

But there was none of the bluster or boisterous humour I'd come to associate with the "special clients" who attended these functions. These women didn't seem to feel the need to attract attention or show off to one another. And when Grace and I did the rounds and chatted to them, there was nothing like the amount of fondling or crude innuendo to which I'd become accustomed.

Which is not to say that they weren't interested in us - quite the contrary. Their eyes roamed over our satin and lace-clad bodies and their smiles hinted at pleasures to come.

One of them, an older woman with close-cropped iron grey hair, invited me to sit on her lap; but where I might have expected to be to grabbed or mauled, she simply stroked my cheek and then ran her hands lightly over my exposed arms and shoulders. I shivered under her touch and my cock stiffened, but if she noticed the reaction she made no comment.

Her hands came to rest on the top of my bodice. Gently, she traced the outline of my nipples under the soft fabric, her touch stiffening them and sending a further quiver through my loins. I'd noticed lately that my nipples were becoming noticeably more sensitive, something I assumed was a by-product of whatever hormone treatment I was getting at the College.

"No falsies, I see", she murmured. "No ma'am", I answered. She seemed to be waiting for me to go on, so I continued. "I, er, don't really see the point of them. Or at least not in the kind of outfits we have to wear here, anyway."

She laughed. "I suppose not. Anyway, I'm glad - can't stand them, on girls or boys. Give me the real thing any day ... Have you said no to those as well?" The question was asked in a teasing tone. I blushed. "No ma'am - or at least, I haven't been given the choice."

"And if you were given the choice?" she asked, her fingers still gently stroking me. Fighting to concentrate in the face of the effect her attention was having on me, I managed to reply: "I, um, haven't given it any thought, ma'am - I'm not sure, to be honest."

That was a lie - or at least the first part. I'd often found myself wondering what real breasts would feel like ... But the arrival of my questioner's main course spared me any further grilling on the subject.

Soon enough, it came time for Grace and I to put on our performance. In other circumstances I would have been anxious to get my hands on her lithe body - indeed I'd lain awake fantasising about just that more than once since our last encounter. But now the awkwardness of our situation was uppermost in my mind. It was with more than a little trepidation that I danced over to her, wondering whether I had it in me to perform as required.

Two things overcame my hesitation. One was a glance at Miss Everett, whose steely gaze told me all I needed to know about the consequences of failure. The other was the reassuring smile that Grace gave me as I spun her round to face me. When I pulled her into my arms and began to kiss her, all my doubts were quickly forgotten. I swiftly grew hard ... and so did she.

As I pulled down Grace's panties and took her stiff rod into my mouth, I could see another difference playing out with our all-female audience. Where the male guests had done no more than unzip their flies, the women watching us chose to disrobe, shedding their clothes and replacing them, if at all, with loose, diaphanous gowns handed out by the serving maids.

Grace must have been turned on - had she too been given some sort of aphrodisiac, I wondered? - because it took only a couple of minutes' work to bring her to the point of orgasm. Her legs jerked convulsively as she came, sending wave after wave of spunk into my mouth. I resisted swallowing it, but held every drop until I had finished cleaning her cock. Standing up, I opened my mouth and held out my cream-covered tongue for the audience to see, before ostentatiously gulping it down.

As I pulled Grace into an embrace, she brought her mouth close to my ear and whispered over the sound of the music that was providing the soundtrack to our act: "God, I needed that ... they've had my cock locked up in some awful device since we slept together, it's been horrible ..."

Before I could respond, she added quickly: "I'm okay now though, all right? But you'd better go ahead and fuck me before that bitch Everett notices ... Besides, I really want to feel your cock inside me again. Cos, you know, we may not get the chance again ..."

I didn't need a second invitation. Just as she had done the first time I had taken her, she lay down on her back with her legs in the air and invited me to impale her from above, giving me the opportunity to rain kisses on her lips and her delicious breasts as I drove into her tight rear passage. It also allowed me to surreptitiously ask her the question that had been preying on me.

"Did you know? About them recording us, I mean?" Her answer was to give me a resounding whack on the buttocks, an action that brought an admiring cheer from a couple of the guests. Startled, I looked down to see her giving a brief glare, before relaxing her features as I continued to plow into her. I grinned. "I'll take that as a no", I whispered.

Grace brought her head up to kiss me, then reached round to nibble my ear. "I didn't know about any of it, you idiot. Would I be on this table if I had?"

It was, I had to admit, a pretty good argument. A weight I had not even realised was there seemed to slip from my shoulders. I leaned down to kiss her again, this time more deeply. I still felt guilty - bit at least there wasn't the spectre of betrayal as well.

Lifting my tempo, I pounded her butt and was rewarded with several gasps. And then I was coming, the sweet release making me gasp and moan as I flooded her depths with my sperm. Groaning, I collapsed on her, my head resting on her sweat-streaked boobs, her arms and legs clinging to me. For a moment, I was lost to my surroundings, spent and at peace.

But quickly enough, reality came surging back. As I slid my shrinking member out of Grace's cum-filled passage, I heard her ask, this time in a normal voice, "Now what?" As she sat up, a stream of lsticky residue dripped onto the tablecloth. Scooping some of it up with her fingers she tasted it appreciatively, smacking her lips. "Yum!"

I grinned back at her. "Competition time. We, ah, see to the guests - though not, I assume, with these." With a gesture I indicated our cocks - though hers, I noticed, had noticeably recovered some of its hardness. "The winner is whoever can get more of them off. But don't ask me if there's a prize, beyond getting out of doing any more of these lunches- I've never had the chance to find out."

I looked around to see the diners watching us expectantly - though there were none of the raucous requests I was used to receiving at this point, and a few had evidently decided to start on one another, rather than waiting for us. Slipping off the table and picking my way past a pair of women who had pulled their chairs together and begun fingering each other's pussies, I made my way over to Miss Everett. Apart from anything else, she was the one person in the room to whom I'd previously given cunnilingus. I'd thought it might be useful to start somewhere familiar.

However, the principal was having nothing of it. "Nice try Katy, but much as I enjoy that wicked tongue of yours, guests do come first - literally, you understand. You can, ah, suck up to the boss later." As the guests around her laughed, she waved a hand at the gray-haired woman who'd previously had me on her lap. "Try Angela there, she's clearly hanging out to get a piece of you."

Doing as I was bid, I sashayed over to my target, whose eyes were glowing as she watched me approach. "Hello Miss Angela", I said coquettishly, "what is your pleasure?" She smiled voraciously, leant back in her chair and opened her legs, her gown slipping open as she did so. Where Miss Everett typically kept her quim hairless, her muff was covered by a tangle of hair, which unlike that on her head was still predominantly black. "Thank you my dear, I seem to have a very dirty crack. Perhaps you could clean it out for me?"

As I knelt down and pushed my nose into her bush, I did my best to ignore the pungent odour, concentrating instead on finding her clitoris with my tongue. As I brought it to life, I was rewarded with a shudder and a rush of fluid. "Lick it", came the gasped command, as her thighs clamped me in place ...

They would not be released until I had made her come three times (I did hope someone was keeping count), by which time my tongue was beginning to go numb. Even then it took two other guests to pull me away. The older of the two commanded me to lie on the floor and promptly squatted on my face, pushing down hard and nearly smothering me as she mashed her pussy into my mouth.

At the same time, I felt her younger companion massaging my flaccid cock back to life. When it was hard enough, there was a pause, then a sensation of warmth and wetness as she lowered herself onto me. Waste not want not, I supposed. Clearly I had been wrong about what we could use to satisfy our clients.

Which reminded me ... Still fighting for breath and struggling to keep my tongue lapping against the woman who seemed to me intent on grinding me into the carpet, I held out two hands either side of me, palms up and fingers wiggling. For a moment nothing happened and I was about to retract them when I felt my left hand seized and guided upwards to yet another pussy. Then the same thing happened on the right.

When, a short while later, I succeeded in bringing four women to orgasm in quick succession (though in truth two of them idid most of the work), I was beginning to think that I might be able to win one of these contests after all ...

Three days later, as I was ushered into the principal's office, my tongue still felt like cardboard ... and my lips remained tender from the relentless pubic assault they had endured. But it had been worth it, I guess. I had no idea of how she could possibly have known, given all those multiple orgasms, but Miss Everett had declared me a narrow victor. I had not personally attended to the principal, but from her flushed expression I assumed Grace had done so - and probably more than once.

As for my erstwhile lover, there had been no fond farewell. She had been whisked away at the end of the lunch, with no opportunity to say goodbye. Still, there were doubtless worse ways to part than after shooting one last load into each other ...

The prize for winning, I'd been promised, was no more of these functions. But what I hadn't yet discovered was what I would be expected to do instead. Given my experiences to date at the College, I wasn't sure I wanted to find out - but I had a sneaking suspicion I was about to be told.

My first indication that something had changed was that both Everetts were waiting to see me - and the second that I was asked to sit down, rather than stand to attention. I lowered myself into the chair that had been indicated and daintily crossed my legs, which today were garbed in white stockings. Vainly, I tied to tug the short, pleated skirt down to conceal the white cotton panties I was wearing, but there simply wasn't enough material. The red plaid mini-skirt and see-through short-sleeved white blouse were without doubt the skimpiest and sluttiest schoolgirl outfit I had ever worn at the College - even counting some of the costumes I had put on to dance at the Club.

"Well now Katy", said Miss Everett admiringly, "you're looking very ... fuckable". The glint in her eye suggested that she would love nothing more than to put that statement to the test.

"Indeed", said her brother with a crooked smile, "but before we get to that, we just wanted to congratulate you on, ah, coming so far so quickly. I'm not sure we've ever had anyone get to the final stage of our program this fast. And to cap it off you managed to pass the penultimate test without any of our, ah, chemical additives to help you along!"

I stared at him as the implications of his last statement sank in. "You mean, the orange juice ..."

"... was just orange juice, yes", he confirmed, his smile broadening. "At least after the first time. You really are quite the slut, Katy. Which of course is why we chose you to do those special sessions in the first place. And why we're about to send you off on one last assignment before you graduate from the College."

My mind was reeling from the thought of all those men (and women) I'd willingly serviced, all it appeared entirely off my own bat (or hand, or mouth, or cock). But a couple of the words Mr Everett had spoken penetrated my mental fog.

"Assignment?" I managed to say. "Um, graduate ...?"

He laughed. "You never seem this lost for words when you're flirting with the clients, young lady ... Your assignment is a simple one. One of our most important clients has been successful in a blind auction that we recently held. His bid has won him the pleasure of your company for the rest of the day ... and tonight."

Could this get any worse? Don't bet against it Katy, I told myself. Aloud, I asked: "Um, my company, sir?"

He leaned forward and looked at me intently, his face now deadly serious. "He can ask for whatever he wants, Katy. And you" - he stabbed a finger at me - "can say yes and no, as you see fit. You go to his house, you have dinner, you make conversation, you sleep in his bed. Anything else is your choice. He knows that, it's part of the auction rules."

He leaned back. "But be very aware. The choices you make will define what happens to you after you've graduated. Or, should I say, what we choose to have you do. Is that understood?" I nodded meekly.

Kristin cut in. "As for what some of the options might be for your future, we'll talk to you in more detail about that when you get back. There's a car waiting for you outside as we speak. But before you go, there is one other choice we're going to tell you about - so you can think it over before making a decision."

The smiles were back on both their faces now and I braced myself, as Miss Everett continued.

"As you may possibly have noticed, we have been transitioning you to what we think of as your correct gender. Because you weren't much of a man, were you ... Martin?"

It was the first time I'd heard that name in what seemed like months. It seemed strange and unfamiliar. "No ma'am", I replied dully. I could hardly deny it.

"No indeed. So, Martin is gone and Katy has taken his place. But there's still something missing - or several somethings, to be precise." Her brother chuckled, but a little dutifully, and I had the impression she'd given this speech before. Wait though, she couldn't mean ... She wasn't talking about ... was she?

Miss Everett's grin stretched a little wider as she watched the play of thoughts as if ithey were written across my face. "You're thinking - they're going to give me breasts and a vagina .. Aren't you?" This last was said sharply and I reacted as if was back in the classroom, being admonished by a teacher. "Ma'am, yes ma'am", I responded miserably.

"Well, let me put your mind at rest", she said in a kinder tone. "We may, ah, push the boundaries a little here, but we're not monsters. We're not going to put you through those two operations, unless you really want to have them both done."

I was starting to exhale with relief, when her next words hit me like a hammer. "But you are going to have at least one of the procedures. That's your choice, see?"

As I stared at her, feeling the colour drain from my face, Mr Everett spoke up. "That's right Katy, it's your call. If you want, we can make you all woman. Or you can just get a boob job - and the size is entirely up to you, by the way. Or, if you like, no breasts - but then no cock either. So if I were you" - he stood up and gestured me to do the same - "I would think very carefully before making a decision." He shrugged. "Because if you don't choose one or the other, you'll get both."

I was barely conscious of leaving the room with him and walking to the lift well. All I could think was - what the hell was I going to do?

(To be continued ... Feel free to email the author with any advice for poor Katy!)