My New Career

Welcome to the tenth chapter of this story of a feminised and increasingly cock-hungry young man whose life has been transformed by what he thought would be a simple job interview. if you have any comments or reactions, I would love you to email me. And do think about donating to help support this wonderful site.

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MY NEW CAREER - PART 10

As I hobbled to the waiting car outside Antony's mansion, clad once again in the school uniform in which I had arrived, my gait was stiffer and noticeably more bow-legged than it had been some 18 hours earlier. But if the driver noticed, he didn't make any comment - for which I was grateful.

Sore, tired and not a little ashamed of myself, I sank gratefully into the plush leather that lined the limousine's interior. As the car pulled away I realised I was shaking my head.

In truth, I could hardly believe what had happened since I last sat in this vehicle. I had been welcomed, dressed in a beautiful gown and treated to a wonderful dinner. After which I had been brutally used by the master of the house and his youthful, good-looking servants. And not just once. They had spent half the night fucking me, time and again emptying their seed into my now tender rear end, or into my mouth, or over my face.

And I had not just agreed to this, but loved it, begged for it even. I had come three times myself, not once with anyone touching my cock. On each occasion the orgasm had come simply from my ass being pounded, from my nipples being licked and pinched and stroked, from the sheer erotic thrill of being fucked by a group of men. I mean, I didn't even like men ... or so I had thought.

But what I still found hardest to believe was that I had been free to say no to all of this. When Antony purchased a night of my time from the Ceder College, the organisation that held me in thrall, we both knew the conditions of the deal. I could have refused anything more than dinner and an unmolested sleep in his bed.

As far as I was aware, our only previous contact had been an admittedly very close encounter at Club Angel, where he had been just one of several customers I had sucked off. Yet he had paid out a very large sum of money to get me, somehow knowing that I would give him what he wanted. He had worked out that I would not just be prepared to let him deflower me, to allow him to stuff his monstrous organ in the place that no flesh had previously been. He had understood that I would implore him to fuck me. Clearly, he knew me better than I did myself ...

So what was I? Well, a slut, clearly. At least - and this was the most worrying thing - when it came to men. I had wantonly had sex with three members of what I still thought of as my own gender, all appearances to the contrary. And not because I needed to earn money, not in response to any threats, but simply because I was excited at the chance to feel their cocks inside of me. I shuddered to think what Mr Stokes would say if he knew ...

Oh god - Mr Stokes! I'd done it again ... For the second time since I'd moved in with my very sweet and generous (if somewhat lecherous) landlord, I'd stayed out all night without letting him know. And both times for the same reason - because I was too busy getting my rocks off to think about getting him a message. And of course I had no way of contacting him myself - the College had never allowed me to have any kind of mobile device since I'd been compelled to dress and live as a woman.

I leaned forward and said to the driver. "Listen, can you get a message to the College for me? I know we'll be back there soon, but it's kind of urgent ..." As usual, my voice was pitched softer and higher than it had previously been. After all the training I'd received it had become second nature to speak this way, and I couldn't remember the last time I'd used my old baritone.

"Sure", answered the driver. "Oh thank you!" I said gratefully. "Could you ask them to give my landlord a call and tell him I'm fine, and I'll be home as usual tonight?"

The driver craned his neck round to look at me for an instant, before returning his eyes to the road. "Your landlord?" His tone had just a hint of amusement. I didn't want to explain my curious arrangement, so I lied. "Look, he's my uncle, okay, but I pay him rent ... Would you mind making the call? He's a bit of a worrying type ..." Well, that last bit was true, at any rate.

To my relief the driver made the call and I settled back again in my seat. Try as I might though, I could not stop thinking about what the immediate future might hold - and the big decision I'd been told I had to make.

I knew that I was going to "graduate" - but what I'd be doing next, I had no idea. The one certainty was that it would be the Everetts, the brother and sister who ran Ceder College, who would decide my fate, not me. Except that I had to choose whether to get breasts, or to have my cock removed and a pussy added in its place - or both. The one option not on the menu was "none of the above" ...

If truth be told, I still had no clue what I would decide. My mind tended to shy away from the awful prospect of having to make this terrible call. Yet I was under no illusion about what would happen if I failed to indicate a preference - I would get to have both procedures.

The rest of the trip back to the College passed with all these thoughts swirling around in my head. It was actually something of a relief to arrive ... but that feeling lasted only as long as it took to notice Kristin Everett waiting for me at reception.

"Ah, Katy - our lovely schoolgirl returns! And by the way you're walking, I'd say you had quite the night as well ... Come on." Beckoning me to follow, she strode off to her office. She was wearing thigh-high boots and a figure-hugging black dress that clung to her curves. I could not help but notice the attractive way her bottom swayed as she moved.

Her voice reached me over her shoulder. "As it happens, we've already heard from our client. It seems he was very satisfied indeed with your efforts ... Though he did warn us not to let you anywhere near any good-looking delivery boys. Why would he say that, I wonder?"

I was glad she couldn't see my face. "I can't say ma'am", I said, trying hard to wipe away the mental image of Ryan and Alex, the two young servants I'd been so keen to flirt with and then seduce.

Miss Everett laughed. "Can't or won't?" But she seemed content to leave it at that. When we reached her office, she told me to sit down and then asked if I wanted some tea or coffee. "Um ... yes, thank you ma'am, some coffee would be great - flat white if you have it."

I felt somewhat flustered by this uncharacteristic display of hospitality. Nevertheless, within a few minutes lNikki, the receptionist, was bringing in our drinks, complete with a plate of chocolate chip cookies. As I nibbled on one of these, I wondered darkly if they contained some sort of drug. But Miss Everett ate one too, and I was soon engrossed in a very different conversation to what I had become accustomed with the College's co-principal.

We chatted quite amiably about nothing in particular, although she gradually and rather deftly steered the discussion round to my night with Antony. Without quite intending to, I ended up telling her about most of what had happened - although I left out the worst of the details and contrived not to mention either Alex or Ryan.

When we had finished, she patted me gently and almost affectionately on the head and sent me off to shower and change. She told me to return and see her late in the day, as there were "one or two other things" we needed to sort out.

By the time of the appointment, I was feeling much better about life. Among other things, I had cleaned off the detritus from last night's activities, enjoyed some yoga, and been primped and pampered by Daniel and Lily. I had also changed out of my schoolgirl uniform into a smart, tailored jacket and skirt, over a red silk blouse. My legs were encased in flesh-coloured stockings, with elegant patent leather pumps.

I took a close look at myself in the dressing room mirror. I could still just about see the nervous young man who had arrived at the College all those months ago for what he thought was a job interview - but only just. I was healthier and fitter, for one thing, my body trim and toned. My skin was smooth, my stubble and chest hair long gone, the locks on my head now grown out and tumbling to my shoulders. My blue eyes, always my most striking feature, were accentuated by makeup and shone out from what was - if I said so myself - a stunningly pretty face. I couldn't help but smile, my naturally full and crimson-painted lips parting to reveal newly whitened teeth.

As Nikki escorted me back into the principal's office, however, the smile had well and truly faded. Miss Everett was going to make me give her a decision about the medical procedures, I was sure of it. And I simply did not know what to do ...

My nervousness increased when I found Gordon Everett waiting for me, along with his sister. Sharply dressed in his customary dark suit, and reclining comfortably on a couch, he looked every inch the successful businessman. He flashed me an expansive smile. "Katy - do have a seat. You look simply ravishing, you know."

"Thank you sir", I replied politely, taking a seat opposite him and looking warily over to Kristin, who was sitting behind the desk, looking through a file. With an audible sigh, she put it down and fixed her gaze on me.

"Now, Katy", she said, "there are some decisions to be made. We want -"

I couldn't help myself. "Oh please ma'am", I burst out, "I can't ... I haven't .. I mean, I don't know what ... Please, don't make me -"

My babbling was cut off by the slap of her hand of the desktop. "That is quite enough, young lady", she said sharply. "One more outburst like that and I'll put you over my knee and spank you, do you understand?"

I nodded miserably, ignoring Mr Everett's quiet chuckle. His sister stared at me hard for a few seconds and then her expression softened a little. "I'm not talking about your body parts. We already know what you'll decide, but we'll let you work it out yourself. The question we need to discuss today is what your immediate future will be."

She steepled her lingers and regarded me thoughtfully for a minute, then continued. "See, here's the thing. All our testing suggests that you're ideally suited to a particular career, one that can make both you and us a lot of money. And I don't mean being a stripper, splendid as you are at showing off that lovely face and body we've given you." She smiled. "You can do so much more ..."

A yawning pit had opened in my stomach. "You can't mean ..."

Mr Everett cut in, his grin as wide as his sibling's. "Oh, but we can. You'll make the perfect escort - or call girl, if you prefer. Catering to the most exclusive of clientele. Rich men - and indeed some rich women - are going to pay through the nose to sample your exquisite charms." He laughed at my expression. "And you won't have to pretend to enjoy it, either. You'll just do that naturally."

"But ..." Once again I was cut off, this time by Miss Everett. "But what, Katy? We can't make you do this? Well, we can and we will. Unless you want those lovely photos of you with an underage boy going viral, that is. You don't want to make a living selling your body? You've been doing that the last few weeks ... with very little persuasion, I might add."

I slumped back in my seat. They had me all right. And as for enjoying all that sex - well, I could hardly deny the truth of my own reactions, could I?

Miss Everett smirked as she watched the play of emotions on my face. "So, that's decided then. You'll work for us as an escort, we'll look after you and pay you well. You can decide how many new body parts you want. And we'll cut you loose after three years. You can keep working for us if you like after that, but as a regular employee, no constraints. Win win, don't you think?"

I was too stunned to respond. I sat silently, contemplating the reality of working as a prostitute for three whole years. How on earth could this have happened? How could I go from being an unemployed male teacher to a high priced call girl? And what if I actually liked it?

"Unless ..." The single word from Mr Everett hung heavy in the air inside the office. I looked at him sharply, daring to think there might be some way out for me.

"There is an alternative", he said, his eyes boring into mine. "Ordinarily, we wouldn't give up the chance of, ah, renting out your services - not with the fees you'll be able to command. But we do have a number of clients who are willing to pay a quite extraordinary amount to have you to themselves ..."

Kristin chimed in. "That's right. You seem to have quite besotted them ... Anyway, here's the deal. We put you up on the auction block. If you're happy with the winning bidder, you agree to live with them for at least a year. They get to own you completely, do whatever they want during that time - except they can't rent you out."

"And if you don't like whoever's willing to buy you," said Gordon, "then it's back to the escort business - only for five years, not three." He leaned forward. "So Katy, are you happy to take your chances with the auction? Or would you prefer to spread your affections around?"

My mind was still reeling at the prospect of making a living from being fucked by strangers. So the idea of committing twelve months of my life to serve one rich man (or woman) as a sex slave,was almost like a lifeline, crazy as that might seem - especially as I could always veto anyone who looked too scary. So, without any real thought, I grabbed it with both hands.

"I'll take the auction, thank you sir", I said. The Everetts exchanged a meaningful look, although I couldn't tell from their expressions whether my decision had at all surprised them.

Kristin clapped her hands together. "Right, that's settled. We have some preparations to make, but before we do that, there's one very important matter we need to attend to ... something we've been putting off for quite a while now." She stood up from behind the desk. "Katy, on your feet ... and lose the clothes, please."

I knew better than to argue. Standing up, I slipped off my jacket, then unzipped my skirt and let it fall to the floor. I stepped out of it, then picked it up, and laid both it and the jacket on the chair. As I started to unbutton my blouse, Miss Everett walked round behind me. I felt her hands roaming over my lace-covered behind, and then she was tugging down my panties. Obediently I lifted first one foot, then the other, and allowed her to remove them.

As she straightened up she ran her fingers up the back of my stockinged legs. I shivered at the caress and felt my cock stir. I removed my blouse and heard another rustle of fabric behind me. And then she was pressing up against me, the swell of her breasts unmistakeable against the bare flesh of my back. Her hands reached round, one going to my groin and the other to my chest. I moaned involuntarily as she teased both my member and my sensitive nipples, which stiffened under her touch.

From behind, I heard her call out to her brother, who was watching us intently. "Gordon, do you want to do the honours?" He responded by reaching into his pocket and pulling out a coin, which he flipped into the air. Deftly catching it, he inspected the side that lay face up and announced in a sonorous voice: "Heads."

"Hah", said Kristin, in a tone of obvious satisfaction, though I had no idea what she was happy about. She pushed me forward and then pressed down on my shoulders, guiding me to the floor so that I was kneeling in front of her brother, who was unbuckling the belt on his pants. I was under no illusion about what I was expected to do. The only surprise was that it had taken so long to be in this position ...

Mr Everett unzipped his pants and reached inside to pull out his cock, which was already semi-erect. With his other hand he pulled my head down to his shaft, which to my surprise was not much bigger than my own modest appendage. After the much larger specimens I had recently had in my mouth, this one slipped in very easily indeed.

"Mmmm", I heard him say as I sucked him to full hardness and then began to work my tongue around the swollen head, "I've been wanting to fuck that pretty mouth of yours since I first saw you in lipstick." He gently stroked my cheek as I fellated him and he let out a deep sigh of contentment. "It seems our clients were telling the truth, you really are quite the slut. What are you, Katy?"

I lifted my mouth off him for a moment and looked up at him. "A slut, sir", I answered dutifully, as saliva dripped from my lower lip and ran down my chin. He grinned. "And what do you love to do, slut?" I flushed, but gave him the response he wanted. "I love sucking cock, sir." He laughed and gestured for me to resume my work.

As I complied, I realised that what stung was not what he was forcing me to say - but how true it was. Well, not entirely true. I didn't really love giving men blowjobs ... but I didn't mind it either. Not when I actually had them in my mouth. And there was a certain satisfaction in bringing them to orgasm, even if it meant having to swallow their cum.

Of course what it seemed I did love, based on my experiences last night, was getting fucked. And as if on cue, I felt what could only be Miss Everett's fingers slipping between my buttocks and lathering my asshole with some kind of lube.

"Stick your butt in the air", I heard her command. Obediently, I shuffled back towards her a little, flattening my back and tilting my pelvis up, all the while continuing to work on Mr Everett's shaft. There was a pause and then I felt something cool pressing against my exposed anus. My ring briefly resisted and then opened to admit the intruder. I gasped as it slid inside me, penetrating deep into my innards.

I recognised the feel of a dildo, but either it wasn't quite as big as some of the ones Miss Everett had previously used on me, or my pounding last night had widened my passage. Even so, while it moved easily in and out, I winced a little as it caught spots still tender from the fucking I'd received last night, especially from Antony's enormous cock. As the dildo reached its deepest point, something hard and leathery slapped against my buttocks and the base of my balls, causing my rock hard penis to sway beneath me. And with each jolt, despite the discomfort, I also felt a pulse of pleasure.

Briefly lifting my mouth off the cock on which I was working, I craned my head round to look behind me. I was rewarded with a brief glimpse of Kristin Everett, naked except for her boots and some kind of harness around her waist, kneeling on the floor and driving herself into me. Her face, usually so composed and businesslike, was twisted with lust and exertion.

A glance was all I got, because her brother grabbed my head and drew it back down to his throbbing member. "Pay attention", he demanded. "My sister may have got lucky with the right to your tail, but I still want my consolation prize. Now, eyes up, slut."

Pulling his cock towards me, I crammed it in my mouth and began alternately sucking it and jerking it with my hand. All the while I tried as best I could to look up into his face, as I had been ordered. He kept flicking his gaze between me and his sister, obviously enjoying the spectacle of her impaling me with her strapon. From time to time he urged her to fuck me harder.

Kristin too now was calling out. "Do you like this, slut? Do you like me fucking you? Shall I go deeper, is that what you want?" She was ramming into me harder and faster now, panting with exertion. And with each thrust of her weapon, I felt the pressure build inside me.

Gordon was the first to come, his cock jumping and jerking as he pumped his jism into my mouth, his eyes rolling back and then returning to meet mine, his face a mask of savage glee as he looked down at me. I was still gulping down his cum as I felt my own orgasm hit, the organ between my legs pulsing and spitting my seed onto the floor. And then it was Kristin's turn, her wild yells filling the office as she pressed hard against the strapon harness, grinding against my rear end, the shaft buried deep in my ass.

For a moment I held my position. The cock in my mouth shrank, still leaking fluid onto my tongue, while the one between my legs also dribbled its way to detumescence. But there was no corresponding movement from the plastic version in my bottom, its length still full and firm within me. I savoured the sensation of being satisfied, and of having brought satisfaction. Perhaps I really could work as a call girl ...

And then reality returned. Mr Everett pulled his organ from my mouth and wiped it, slowly and deliberately, on my lips and cheeks. "Good girl", he said, breathing heavily. Behind me there was a slurping sound as his sister pulled her strapon out of me, the muscles in my ass clenching reflexively as the invader was expelled. I glanced around and was astonished at how long the dildo looked. Had I really taken all that?

Miss Everett caught my look and laughed. She was still sweat-streaked and panting from her efforts, but found the breath to say: "As I think my brother said, it seems our clients know a thing or two. You really are quite the performer ... But don't think I'm finished with you yet. Not when my pussy is as wet as it is right now ..."

Unbuckling the harness of the dildo, she tossed it to one side and then walked heavily over to the couch, where she sat down next to her brother. Leaning back, she opened her legs, slipped two fingers into her crack and then held them up. They glistened in the artificial light. Jerking her head over towards the desk, she looked at me and said: "There are some tissues on there. Get your face cleaned up and then get back here. And do it quickly."

I did as I was instructed, wiping away the goo around my mouth and then returning to kneel before her legs. She gestured imperiously and I leant forward to apply my tongue to her hot and sweaty gash. As promised, her juices flowed freely as I probed her labia and lapped at her clit. She moaned in response and thrust hard up against my mouth, at the same time grabbing my head with two hands to hold it in place.

Beside her, I heard her brother get to his feet and then zip himself up. "I'll, ah, leave you to your seconds, Kristin", he said. "Do you want me to send Nikki in?"

"Please", came the reply, between gasps, "she knows what to do. And you, don't you dare stop!" This last was obviously to me, and I redoubled my efforts. Behind me, i heard a door click open and then, perhaps thirty seconds later, close again. Was the rceptionist going to join in, I wondered?

For a moment I was sure she was, as I felt a hand on my deflated cock. But I quickly realised she was just cleaning me up, using a wet wipe. "Hold still, Katy", I heard Nikki whisper, and the next thing I knew she was fastening some kind of device around my waist and between my legs, the metal (or perhaps plastic) cold against my skin. It was all I could do not to twist round and see what she was doing - but I was well aware of how Miss Everett would take it if I interrupted my cunnilingus.

As I licked away at the increasingly aroused principal, I felt my shrunken member drawn back underneath me and encased in some kind of cage. There was a click as a clasp was fastened, and then another as a strip was drawn down between my buttocks and connected to the cage, which also now firmly held my balls in place.

Any immediate curiosity was deterred by Miss Everett, who clamped her thighs around my head and proceeded to come, not once, but several times. Fighting for breath as she smothered my face, it occurred to me that maybe there might be worse things than having female genitals ...

It was only when she had let me go that I had the chance to inspect what had been done to me. My groin was now encased in some kind of device that precluded any access either to my cock or my anus, which was covered by a plate with a small hole in the middle. Although flexible enough that I could move without discomfort, there was no way to dislodge it. The material, which i still couldn't identify, was light but very tough.

"It's a chastity belt", said Miss Everett, her voice heavy and her face still flushed from the force of her multiple orgasms. She smiled at my expression. "To protect our investment, you understand. You can take it off for brief periods here at the College, while you're under supervision. But otherwise it stays on round the clock. No sex for you, young lady, until you're ready to start work for us, or go into service with whoever buys you."

Unsteadily, she rose to her feet and went to find her clothes. As she dressed she continued her explanation. "You'll find that it's perfectly comfortable ... with a couple of exceptions. I would definitely recommend not getting aroused - that will prove very painful. And going to the toilet will, I'm afraid, be a bit ... messy. But you'll get used to it. You'll have to, because you certainly won't have a key."

She adjusted her dress and went to sit down behind her desk, from which she picked up a mug of what must have been lukewarm tea, draining it in a single gulp. "Ahhh, I needed that", she said. "Getting eaten out always makes me thirsty." She nodded at me. "You can put your clothes on now, Katy."

As I slowly moved to comply, still dazed by the revelation that I had been locked in a chastity belt, of all things, Miss Everett turned to Nikki. "It's time for Katy's medicine", she said. The blonde receptionist, who had been dutifully standing by, slipped out of the room. She returned a minute later with a glass of water, handing it to me along with two small white tablets.

I shot a quizzical look at the principal. "They'll help suppress your libido, just temporarily while you're locked away. Trust me, you'll be glad of it. You do not want to get a hard-on right now, I can assure you." As I took the tablets, she smiled thinly, then continued. "It does also have one other effect ..."

I found my voice. "Um, what's that, ma'am?" I wasn't sure I wanted to know the answer, a feeling which only grew as her smile grew broader. "Well", she said brightly, "let me show you. Now, let's see, where is it ... oh yes. Nikki, if you take a look on the floor just in front of the couch ... no, the left side ... that's it ... you'll find a nice little puddle of cum that naughty Katy produced. The last one for a while, that's for sure."

The receptionist was kneeling by the spot where I had shot my load, a confused expression on her face. "Did you want me to clean it up, ma'am?", she asked. Kristin laughed. "In a manner of speaking, yes ... Get down and lick some of it up, but don't swallow any."

The young blonde lowered her face to the carpet and did as she was told, "Now", instructed the principal, "go and giive Katy a nice wet kiss." Nikki straightened up and walked toward me, her face registering her obvious distaste at what she had been asked to do. But we both knew better than to argue. Tentatively, she leaned in to deliver an open-mouthed kiss.

As out tongues entwined, my mouth was filled with an unspeakably vile taste. Reeling back, I coughed and spat, trying without success to rid myself of the horrible flavour. It was only when I grabbed the remains of the water I'd been given that I was able to wash some of it away, though the residue still made me curl up my face in disgust. It was all I could do not to retch.

Miss Everett chuckled. "I'm sorry Katy", she said, though she sounded nothing of the sort. "I thought a little demonstration was in order. While you're taking those tablets, that's what will happen if you get even the smallest drop of semen in your mouth. I'm told the chemical reaction is most unpleasant ... and judging by your reaction, I'd say that was spot on!"

She looked at me coolly. "That's it, I think. You can go home now. Be sure you get here on time tomorrow. You won't be doing any more work at the Club, but you'll still be keeping up your other lessons - at least for the time being. Plus taking your medicine, of course ..."

She held up a warning finger. "Just so we're clear ... No sex of any kind. And that includes giving your landlord those blowjobs he so enjoys. Not unless you want to throw up over him, that is ..."

It was not until I was on the train home, my bladder bursting from all the water I'd drunk, that the horrible taste began to fade. But the physical discomfort was nothing compared to the mental anguish. And of all the thoughts swirling around my head, about surgical procedures and auctions, of working as an escort, or the strange belt and cage I could feel inside my panties, one was uppermost. The most immediate problem - what on earth was I going to tell Mr Stokes?

(To be continued)