My New Career - Chapter 8 free porn video

MY NEW CAREER - PART 8 As the wheels of the limousine crunched on the gravel of the long, curving driveway, I peered out through the darkened glass at our destination. Set back a long way from the road in one of the city's leafiest suburbs, in what seemed to be some kind of private park, the mock Tudor mansion was huge. Its gables and chimneys cast long shadows in the late afternoon sun as the vehicle came to rest outside an ornate front door. The driver, a taciturn young man in a dark suit, got out of the car and scurried around to open the rear door for me. "There you go Miss. I'll be back at 10am tomorrow to pick you up, okay?" It was as much as he'd said on the entire journey. "Thank you," I replied, clambering out and looking around. There was nobody in sight, no hint of a reception party. There were a lot of things on my mind as I carefully picked my way towards the entrance, doing my best not to get my heels trapped in the loose stones. The uniform I was wearing, for one thing. I might as well have been holding a sign with Slutty Schoolgirl printed in fluorescent pink. There was the short skirt that not only failed to cover the tops of my white stockings, but revealed my cotton knickers with every movement. The flimsy blouse that did nothing to conceal the bare flesh underneath and finished a good few inches above the waistline, exposing my bare midriff. The tie loosely knotted around my neck, almost begging to be torn off. And, to cap it off, platform heels in patent black leather, trimmed with the same red tartan that appeared on my skirt and tie. This was somebody's idea of a fantasy, no doubt about it. Funny to think that only a few months ago - though in truth, it felt like years - it might have been my own fantasy, given my predilection for girls in uniform. Not, I reflected, that I could have afforded to purchase a night with any girl looking as hot as I did right now ... And there was another thing. I'd been bought, in a blind auction of all things, by some mystery bidder. If any proof was needed of the complete control the Ceder College had over me, there it was in a nutshell. It hadn't even occurred to me to protest, let alone to refuse to make the trip. There had been times during the car ride when we'd been stopped at busy intersections, and it would have been so easy to open the door and escape ... But where would I go, without any money or documents? The College already knew where I lived - indeed they trusted me to go back there on nights and weekends. And it was not as if I was doing anything at home to escape from the feminisation that had been forced on me at the College. Quite the contrary. Out of desperation (at least initially), I had fallen into a bizarre relationship with the much older man who had previously been my landlord, but who was now keeping me in a certain amount of style as his girlfriend. Perhaps, I mused, it would be better if I told the whole story to Mr Stokes. Although his lifestyle was far from ostentatious, he seemed to have a fair bit of money. Maybe he could take me away somewhere ... But I was scared of the Everetts, the brother and sister who ran the College, and wary of the influence that their obviously rich and powerful clientele could bring to bear. And I didn't want to see Graeme hurt in any way. Not when he had been so good to me ... All the same, I would have to tell him something soon. Because there was the biggest worry of all, the one that had kept me awake for most of last night as I lay curled up beside him in the baby doll nightie he so adored on me. The choice that, according to the Everetts, I would soon have to make. Between losing my cock and gaining a pair of tits. Or, if I really wanted to complete the transformation, going into surgery to add both breasts AND a pussy. How could I even begin to make that decision? If I opted to have boobs, even smallish ones, that would put an end to any hope of ever passing as male again - unless I strapped them down (which I guessed would be uncomfortable) and never ever took off my top. But the alternative would mean losing ... well, my manhood. There was no doubt at all that I'd grown to love dressing as a woman over the past few months. And judging by my ability to travel to and from the College without being stared at (as opposed to ogled), I could clearly pass as one too - at least superficially. But I was far from sure that I could keep up the pretence if I had to interact closely - say at a job - with a bunch of people who were not in on the secret. There was also the continuing worry of running into someone from my past. I had no living family (my parents had both died when I was young and I had been an only child), nor any close friends - but there were plenty of people with whom I'd gone to school or Uni who might recognise me. I could tell something like the truth and say I was "transitioning" ... but that would bring its own complications, even in these relatively enlightened times. Besides, the fact was that I had been born a man, and I still thought as one, pissed as one and - when given the chance - fucked as one. If I was going to give that up, maybe it would be better to go all the way? Yet that prospect scared me even more than the other two options ... It was a mark of just how distracted I was that I didn't even realised that I had reached the front porch of the mansion and rung the doorbell until the door swung open. A good looking young man greeted me with a quiet "Hello miss, please come in". I was halfway across the threshold before I did a double take. The youth who had greeted me was wearing exactly the same uniform as I was - plaid skirt, stay up stockings, high heels and all. But where I cut a thoroughly feminine figure, with my makeup and high ponytail, he had nothing of the sort. He was simply a boy in a schoolgirl uniform. Where I looked sexy (even if I said so myself), he simply looked ... ridiculous. His face tightened as he took in my reaction, but he merely said "This way" and set off down the corridor. His gait was awkward and unconvincing - didn't he know how to sway his hips? - and I was seriously worried he was going to topple off his platforms. But he showed me without incident into a drawing room, where I was invited to take a seat on a plush sofa. "I'll let the master know you're here," he said, and left the room. He had been gone only thirty seconds when the door opened again. For a moment I thought the same servant had returned, until I realised it was a different young man, dressed in the same outfit. He looked a little older, but there was a clear facial resemblance - a bother, I guessed. "Would you like a drink, miss?" he inquired, again in a soft voice. "Wine, spirits ... or a soft drink?" I was on the verge of asking for a lemonade when I thought, what the hell, I could do with something stronger. "Vodka and lime, if you've got it," I said brightly, flashing him a smile. "I ... I think so - I'll go and look, okay?" I wasn't entirely sure if it was the request or the smile that had unnerved him, but he almost ran out of the room - or would have done, if his heels had let him. In a small way, his reaction made me feel better. Having spent so much of my teenage years (and indeed early twenties) being awkward and tongue-tied around pretty girls, it was nice to have things the other way round ... Soon enough, he was back, bearing a silver tray and glass tumbler. "Um, I didn't add any ice. Is ... is that all right for you, miss?" he asked in a nervous voice as he handed me the glass. I took a sip, only narrowly resisting the temptation to down what was a pretty generous amount in one gulp. "Mmmm, that is just perfect thank you ... ?" He swallowed. "Um, Ryan .. it's Ryan, miss." "Well thank you kindly Ryan, it was very good of you, really ..." As I said this I reached up and rested my hand on his arm, just very lightly, my eyes wide as I held his gaze. He drew his arm back as if shocked. His face coloured and his mouth moved as if he was going to speak ... but he thought better of it and beat a hasty retreat. As the door closed, I took another sip of the vodka and chuckled quietly to myself. I really shouldn't flirt like that with impressionable young men ... but he was pretty cute, after all. For a boy, I added hastily to myself ... The smile disappeared, however, as I remembered why I was here. I had been sent to spend a night with one of the College's clients, who had "won" me as a prize in an auction. That was humiliating in itself - but what really disturbed me had been the freedom I had been given to say yes or no to anything that the man involved might propose. The implication was that I would be judged by my choices - but in what way, I had no idea. Clearly, it wouldn't do to refuse any kind of sexual activity - I couldn't imagine a client being happy with paying what I assumed to be a large sum of money just for someone pretty to wake up next to in bed. I had no problem with offering oral sex or a hand job - I'd gotten well past the point of being squeamish about that. But would I be expected to go further? "No way," I said aloud. There had to be some limits on what they could make me do, and I resolved then and there that it was time to draw a line in the sand. After all - "No way what, Katy?" asked a deep voice, from immediately above and behind me. Startled, I tried to twist around. The empty tumbler I had been cradling slipped from my hand and fell to the floor, breaking with a crash on the polished floorboards. Splinters of glass went everywhere. As I got to my feet, I babbled an apology. "I am so, so sorry, I didn't hear you -" The words broke off as I recognised the tall figure standing behind me, his face wreathed in a crooked smile. It was the man called Antony. I had last seen him some weeks back at my first ever lunch session, when he had commanded me to serve him first. "Serve," that is, in the sense of giving him the first blowjob. As indeed I had done ... and also given him the last too, if I remembered correctly. He had also been notable for having by far the largest cock I had ever tried to put in my mouth. It was only with a supreme effort of self- control that I didn't look straight down at his crotch ... "Entirely my fault," he was saying, "I really shouldn't sneak up on young women like that. It's a serial failing, I'm afraid. Now, just you sit yourself down and we'll get this mess cleaned up." He held his hand up and clicked his fingers together twice in quick succession. Seconds later, Ryan appeared. "Yes master?" His tone was no more assured than it had been with me. "Bring a dustpan and brush and clear up this mess. And while you're at it, you can get the young lady another vodka - and I'll have a G and T." Having issued these crisp commands, Antony walked around the sofa and, picking his way carefully between the fragments of glass, lowered himself onto the couch next to me. My eyes followed Ryan out of the room and then flicked back to my host. There must have been a question in them, because he smiled again: "You want to know about my curious taste in servants, is that it? Or were you wondering about how I summon them?" I smiled back, despite the butterflies in my stomach that his arrival had prompted. "Well, both, actually ..." He laughed. "There's no mystery to the summons. I have all the main rooms wired up with microphones, and a program that recognises specific sounds as signals. That sends an alert - or actually a mild electric shock - to whichever servant I want to see ... and a screen in their waiting room tells them where I am." "Um, very practical," I commented. He gave an amiable shake of his head. "Not really! It's more done for my amusement ... which is also the explanation for the servants." He paused as Ryan re-entered with our drinks, and waited a little further while the broken glass was cleaned up. When the servant had left the room, he reached over and clinked his glass against mine. "Cheers. Now, where were we? Oh yes, the servants. Well you see, a competitor decided to start a price war with one of my businesses. Not a smart move. So I made the people behind this company an offer they couldn't refuse. I paid them each a very handsome sum to buy out their business. On condition that both they and their children came to work for me." His mouth creased again, but this time the smile didn't reach his eyes as he stared thoughtfully across the room. "They should," he said pensively, "have read the fine print. But they didn't. Which is why the parents are now considerably richer, but working in some of our, ah, less attractive locations overseas. And the children get a daily reminder of the folly of testing my authority." He turned back to me. "You've seen how I get Ryan and his brother to dress up - or at least one example, anyway. It amuses me to humiliate them that way, without letting them look even vaguely feminine. And indeed to show them" - he waved a hand in my direction - "what the real thing looks like. I have some others in the kitchen and the gardens who get a similar treatment." I had no idea what made me so bold - perhaps the vodka? - but I asked the first question that sprang to my mind. "Do they share your bed as well?" He guffawed. "Them? Absolutely not ... Though I do keep threatening to lend them to some of my business associates that are more, ah, that way inclined ..." He shifted position to sit a little closer to me. "But enough of the hired help," he said genially, "let's talk about what we're going to do with you, Katy ..." His moved his hand over and rested it on my stockinged thigh. I felt a little shiver. "Sir?" I managed, fighting to keep my voice level. "Master," he gently corrected. "I am of course fully aware of the terms of my transaction with the College. But I would not have invested so much without being confident that you could be, ah, persuaded to give me what I am looking for. So tell me Katy, is my confidence misplaced? Are you ... persuadable?" I smiled with an assurance that I definitely didn't feel. "Sir - I mean, master - I'm sure that you'll be very happy with what I can do for you." "Oh indeed," said Antony. "But there is nonetheless an important choice as to how we spend our evening. So I will ask you this: Will it be the dungeon - or the romantic dinner?" "Dungeon?," I exclaimed, my voice cracking slightly. "You have a dungeon?" He laughed. "Oh yes - and a very well equipped one it is too. Would you like to go and see it? I may have one of the parlourmaids in chains at present ... But I'm sure she won't mind if we look in." "Uh, n-no thank you, s- ... er, master," I stammered. I was almost certain he was joking about the parlourmaid. But having had a taste from Miss Everett of what a dominating person could get up to with some bondage toys and equipment, I wasn't anxious to test that theory out. "If it's okay, I'll take the romantic dinner." To my relief, he didn't seem at all perturbed by my choice. "Thought as much - which is why I've organised some proper clothes for you." He chuckled at my expression. "What, you thought you were going to spend the whole evening in that outfit? Now, don't get me wrong. It is one of my favourites - and you do look utterly delectable in it. But as I've said, it was aimed more at the servants. So you'll change into something more appropriate for dinner." He hauled his powerful frame upright. "I have some business to attend to, and we still have a little time before dinner. You can wait here and finish your drink - and if you get bored there are some books over there." He indicated a floor to ceiling bookshelf that contained a collection of beautifully bound tomes. "I'll have one of the boys take you upstairs to get changed, when it's time." I spent the next hour alternately looking out of the window as dusk fell over the well-kept gardens that surrounded the house, and idly leafing through some of the books, most of them classics that I hadn't seen since high school. I was trying very hard not to think too much about the evening that lay ahead of me. Even so, it was with a feeling of expectancy that I greeted Ryan's brother - the one who had originally greeted me - when he came to collect me. I followed him up a grand staircase, before setting off down a long corridor. I was halfway along it when I finally ran out of patience. Stopping, I called out to the servant who was walking - or tottering - ahead me. "Wait! Just hang on for a minute. Look ... sorry, what's your name?" He looked at me uncertainly. "Um, it's Alexander - or Alex. Sorry miss, but why-" I cut him off. "Alex. Okay, well, the way you're trying to walk in those heels is doing my head in. I keep thinking you're going to come a cropper any minute!" He blushed, looked down and mumbled something. "Sorry, what was that?" I asked. "I said, that does sometimes happen," he repeated in a louder voice. "But what-" Again, I spoke over him. "Look, just watch me, okay?" I moved confidently down the corridor, pivoted smartly and walked back towards him, talking as I went. "See the way I swivel my hips, and put one foot right in front of the other, not off to the side, but like you're keeping every step on a single line. Heel always comes down first, understand? And you take small steps, right? Okay, now let's see you give it a go ..." It took him a few attempts, but before long he was at least moving a little more smoothly - even though he still looked distinctly ill at ease. I patted him on the arm. "Look, just try and remember all that, if you can - and make sure you practice! Now, where's this changing room?" He showed me into a bedroom. There was some lingerie on the bed and a pair of shoes next to it, but no sign of a dress. After some searching, I found one hanging up in a wardrobe. I drew it out and gave a low whistle. It was a long black dinner dress, with a high neck (perfect for my lack of a bust), a long slit down one side, and a curving lace panel that ran from the neckline down to one hip. It was utterly gorgeous. Closing the door and then the curtains, I quickly changed, swapping my white knickers and stockings for black lacy panties, a matching garter belt and sheer black stockings, together with simple but elegant black pumps. The panties, I was unsurprised to find, had the usual pouch to enclose and conceal my member. Finally, I put on the dress. It fitted me perfectly. Opening the bedroom door again, I summoned Alex, who was waiting outside. "Be a dear and zip me up, will you?" It was hard to keep the smile off my face as I felt his fumbling fingers struggle to work the zipper. When it was done, I turned around, stepped back and gave him a twirl. "So, how do I look?" His face flushed bright red as he looked at me and then down at the floor. "You're beautiful miss," he breathed. "Why thank you kind sir," I said brightly. "But you do realise I'm a mister ... not a miss?" I had no idea what possessed me to say this, but the shocked look on his face was something to behold. Stepping close to him, I brought my mouth close to his ear and whispered, mischievously: "But you can still call me miss, okay?" I gave him a quick peck on the cheek and then walked over to the mirror on the wardrobe, resisting the urge to giggle at his discomfort. The reflection was all I could have hoped for. I had never, I thought, looked so glamorous. Looking over at Alex, who was still gaping at me, I said: "So, time for dinner, I assume?" He escorted me downstairs to a dining room with an enormously long table at its centre. Two places were set at one end. Antony was already seated, but rose to greet me. He was wearing a formal dinner suit, with a black bow tie. He looked ... not handsome exactly, but attractive, in a rugged way. The touch of grey at his temples lent him a distinguished look and, as on every previous occasion on which I had seen him, he looked utterly at ease. ?Katy,? he greeted me, ?you look ravishing. I do hope you have an appetite ...? Indeed I did, which was just as well. We were served a series of small courses, each with their own matching wines, and all of them utterly delicious. As the meal progressed, and the more I drank, the conversation turned from the kind of light and frivolous chit-chat with which I had become accustomed in entertaining men at the Club, and became more personal. Perhaps I was becoming more relaxed, or maybe it was just the strangely compelling manner of my host. Whatever the reason, I began to talk about the way I had been trapped into working at the College, and how I had adjusted to the challenge of being forced to take on a new persona. It was only later that I realised I had not had this conversation with anyone else, or just how much it meant to me to reveal my feelings. There were still some details that I held back, including my brief fling with Grace, but I was entirely explicit about the sexual acts I had been induced to perform. Since Antony himself had been a beneficiary of my work and had seen me drenched in the cum of a group of strange men, I figured there wasn?t too much to hide. But I also spoke about my relationship with Mr Stokes, which plainly intrigued Antony. ?So you sleep with him, and jerk him off ? but he?s not paying you?? he asked at one point. I took a sip of my wine and thought for a moment. ?We-ell, originally he kind of was paying me for all those handjobs, because he was giving me free board and lodging ? although you could just as well say the handjobs were my rent ... Anyway, it was definitely a commercial arrangement. But now ... well, it kind of feels more like we just live together. He definitely thinks of me as his girlfriend.? Antony was looking at me intently. ?So how do you feel about that?? I shrugged. ?I suppose I kinda like it. He?s a sweet old man and I don?t mind making him happy ... Anyway, enough about me, tell me more about this amazing house. Have you had it for long?? It was not until some time later, as we were relaxing on a couch in a well-appointed living room, sipping fine brandy from gigantic glasses, that Antony returned to the topic. ?You really do make a beautiful woman, you know. Though I think you are fully aware of that ... You could hardly miss the effect you?re having on my servants, for instance.? I giggled. ?Those two are so sweet, even though you make them wear those ridiculous outfits. At least Alex seems to be walking a little better now, hopefully he can pass on some tips to his brother ... But yes, I think I scrub up pretty well.? He smiled. ?But do you enjoy being a woman, Katy? Is this what you want?? He extended a hand to gently stroke my cheek. ?Yes,? I answered softly, ?I think so.? ?And this?? Reaching across with his other arm, he pulled my head towards him and brought his lips down on mine. I had been waiting for this all evening. So when the kiss came, it was not a surprise ? but my response was. As our mouths locked together and I savoured the sensation of submitting to his passion, of opening my mouth to receive his probing tongue, I knew I was not just willing to be his ? I wanted him. When he finally released me I stared wonderingly into his eyes. At that moment I had no thought of being with him to fulfil an assignment, no concern for what my submission might mean ... just a desire to be his, to be taken by this strong man, to give him everything I had. His final question did not need to be asked, I could read it in his gaze. And I knew the answer to give. Without breaking eye contact I reached down and across, my questing hand moving to his groin. He parted his legs slightly and I cupped his manhood. As it stiffened and expanded under my touch I brought my mouth up to his once more. Where the previous kiss had been sweet and sensuous, this one was urgent and lustful. He was not the first man I had kissed ... but this was the first time I had really wanted it to happen. Far from being the turnoff I might have imagined, his intoxicating maleness excited me more than I could possibly have believed. As Antony enfolded me in his arms, and I surrendered entirely to his embrace, I felt myself harden ... After a while I felt him disengage and stand up. His hand found mine and he pulled me easily to my feet. ?Come with me, Katy.? His softly voiced command brooked no disobedience ? not that I would have even considered it. As he led me out of the room, there was only one possible response. My voice was husky with lust and desire as I told him what he wanted to hear. ?Yes master.? He led me upstairs, to a richly appointed chamber with a classic four- poster bed. The bedroom might have been straight out of a magazine ? and probably was, as I reflected later. But it was not to the bed he took me, but to a tall, ornate mirror on a wooden stand. He stood behind me and I watched him kiss and nuzzle my neck, then ease down the zipper on my dress and slip it from my shoulders. I slid down my panties and stepped out of them. Freed from its confinement my stiff dick sprang erect. It was so hard that it hurt, but when I reached down to touch it his arm snaked out and caught me by the wrist. I looked at him questioningly in the mirror and saw him gave a small shake of the head. Releasing me, he began undressing, all the while holding my reflected gaze as I stood there in my stockings and heels. When he had completely disrobed, he turned sideways and bade me do the same, so we faced each other, still in front of the mirror. His large body was muscular and covered in fine dark hair, with only a hint of a belly. My eyes widened at the sight of his monstrous appendage, which was even larger than I had remembered. At a gesture from him I went down on my knees. He was so tall that the top of my head barely reached his groin. When I tilted my neck back his erection rose above me like a skyscraper. With no hesitation, I brought my lips up to his large balls and began to lick them, then slowly worked my tongue up his magnificent shaft, straining to reach the top. He helped me by bending his legs slightly, lowering himself so that I could complete the journey. As my tongue reached the tip, I worked it around the glans, savouring the sweet and salty taste of the first drop of pre-cum. And then I was pulling down on his organ like a massive lever and cramming the head into my mouth ? or as much of it as I could fit. Slowly, and trying not to either choke or catch him with my teeth, I began to fellate him, my jaw held so far open that it hurt. With my free hand I reached down to grab my own cock ... but stopped as I remembered his earlier injunction. And now his own hands had come down to grasp my head, and I was no longer doing any work, but simply letting him thrust. As I glanced sideways at the mirror it presented an incredible sight, this hulk of a man pushing his gigantic dick ? or part of it at least ? into the painted mouth of the beautiful, flat-chested girl that I had become. And yet, erotic as it was, there was something missing ... I was beginning to prepare myself to have my mouth blasted with cum, when all of a sudden Antony stopped. Stepping back slightly, he let out a long breath and then tilted my head up. His gaze bored into me and, as if from a great distance, I heard him speak. ?Katy ? tell me what you want.? It was not a question, because he already knew the answer. And so, suddenly, did I. ?I want you to fuck me, master.? Antony smiled then, and drew me to my feet, taking me over to the bed. I would have lain down on it, but he had other plans. He had me climb up onto it and then settle down on my knees and forearms, my head towards the middle of the bed, and my butt in the air, hanging out over the edge. There was a brief pause and then I felt my ass cheeks parted and some sort of lube smeared around and into the rim of my exposed anus. I moaned softly as first one finger was worked inside me, and then a second, and finally a third. It was all I could do not to reach under me and wank my throbbing cock. The fingers were abruptly withdrawn ... and now something else was pushing to get inside my gaping hole. It was far too big to do so, however much the rim stretched and strained to admit it ? and then suddenly, with one last tremendous push, it wasn?t. I gasped aloud as my defences were penetrated. The pain and the pressure were horrifying and they only grew as Antony steadily pushed himself further inside me. I was sure that I was going to rupture. Gasping for breath, I pleaded for him to stop. ?Relax,? he said, ?just relax Katy?. His tone was reassuring, but firm. Trying not to panic, I fought to loosen my muscles, to stop fighting the intruder. As I did so, the pressure eased only slightly, but at least the pain started to recede. He waited for a moment , then pulled himself out. The relief was overwhelming, but the respite was brief. I felt more lube being applied, then he was back inside me. It still took considerable force to get past the rim, but once inside, he could now start to push in and out. The pressure was still tremendous, and I was still gasping at every thrust. But as the pace of his penetration began to pick up, as he started to force his way further inside me, as my panting started to synchronise with his grunts of exertion, I began to experience a sensation that, once known, can never be forgotten. The feeling of being fucked. It was not just the physical sensation. It was the sense of submitting to the most intimate form of dominion. And as a few of the deeper thrusts started to hit the sensitive spot on my prostate, pleasure started to flood my lower body. Between my legs my cock, pathetically small by comparison with the weapon that was spearing me, throbbed with every stab. Antony was becoming more urgent, his grunts louder and his strokes deeper. He had been grasping my hips to steady him, but now he released a hand to seize hold of my ponytail. I felt my head pulled back towards him, and I arched my back, at the same time trying to push back into him. ?Fuck me! Fuck me master!? I cried out as he rode me hard, rode me in a way I could not possibly have imagined ... And then with a roar he was coming deep inside me, spurting again and again, shuddering as he emptied his balls into my willing hole. And I cried out too ? not with orgasm, but with ... I don?t know, some kind of vicarious joy. Because he had given me exactly what I wanted, and what I needed. And I knew I would never be the same again ?