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Sexy Secretary Intro My penname comes from a character I used to play in LockedInLace.com interactive fiction. One of the stories was based on the enigmatic M&R Corporation and I loved the idea of hapless males being transformed by a faceless corporation. I also loved the idea that the victims of M&R Corporation were forced to choose (or were allocated one by their "sponsor') from one of four feminine roles: schoolgirl, secretary, maid or sex-slave. I plan to write a story for each of these roles, although not in the M&R Corp context and this is the second (after Sweet Schoolgirl). I used the character, Stacie Swallows, in the M&R game for a couple of years and this story is dedicated to everyone that played with me, especially Siaera and Monica Goodhead. As always, love to hear feedback and reviews on this or any of my other stories if you read them. Helps make the next one better. Sexy Secretary Tragedy struck me just after my seventeenth birthday when my parents were killed in a car accident. I spent a few terrible months grieving, placed in a miserable care home which I utterly detested. After those months, I was collected by my Mother's sister, my Aunt Lynnette, to go and live with her. I had never met my Aunt Lynnette before, she wasn't close to my Mother, and it seemed she had not been overly enthusiastic about taking on her sister's teenage son. That impression was reinforced when she collected me and seemed very cool and indifferent towards me. Aunt Lynnette was much younger than my Mother, only just over ten years older than I was. She ran her own very successful business and was already a multi-millionaire and I was extremely impressed by her very expensive car and the large house that she took me back to. Aunt Lynnette was also a stunningly attractive woman, with long black hair, porcelain skin and blue eyes, a classically beautiful face and an astonishingly sexy body with large breasts and curvy hips. She was always very well dressed, either in business attire or casual clothes, her make-up and hair immaculate at all times. Men went absolutely nuts for her but to no avail - Aunt Lynnette, it turned out, was a cheerful lesbian. Living with Aunt Lynnette was very comfortable but she herself was obviously disinterested in me to the point of being cold, although never overtly hostile. She did make it clear to me, though, that she expected me to leave her house and make my own way in the world once I had finished school. My school grades were borderline and there was a distinct possibility that I might not make it into college. I broached the possibility of taking a job at her business with her. There was nearly always a vacancy for an administrator there (she had a habit of sleeping with the young women she hired and discarding them when she grew bored of them) and I was sure I could do that easily enough. Her answer took me by surprise. "The only vacancies I have at my office are for administrators and receptionists, Steve. I am not hiring a scruffy boy to do either job so, unless you're prepared to wear a short skirt and heels to work, you can forget that idea," she told me in a voice dripping with condescension. I dropped the idea, as I knew I must, but it was as if that short conversation had planted a seed in my mind that started to grow and take over my thoughts. What would it be like to wear pretty clothes and be treated like a girl? I could only think it would be better than my current life and my thoughts turned to being a girl more and more. My first chance to experiment with this new idea came around less than a week later when Aunt Lynnette announced that she would be spending the evening out with some girlfriends. I waited nervously while she got ready and when she finally left, I waited five minutes before sneaking up to her room. Opening the door, I entered, taking in the distinctly feminine d?cor. I'd seldom been in her room before and it seemed strange and very different to mine, although extremely enticing. I stepped over to her chest of drawers and, trembling slightly with nerves and excitement, gently pulled the top drawer open. Inside was several neat piles of Aunt Lynnette's lingerie, neatly stacked as panties, bras, bodies and slips, all in delicate satin and lace in a pleasing variety of feminine colours. I was surprised, but very pleased, that Aunt Lynnette's taste in lingerie was quite so girly and feminine. Like I was picking up something slightly dangerous or explosive, I gingerly pulled out a pair of pale peach, satin, full-backed panties with white lace detailing on the front and ruffles round the leg holes and waistband. A small voice in my head suggested that I should just put them back and leave, that nothing good would come of this. I ignored it and draped he panties over the edge of the drawer. Staring fixedly at them, almost mesmerised, my hands automatically stripped my male clothes off and dropped them on the floor. Picking up the panties I stretched them out and stepped in them, all possible resistance I could have put up now vanishing. I delighted in the sensation as I pulled the flimsy garment up my legs and over my hips. They felt so clingy and sensuous as I smoothed the soft fabric over my ass and hips. I caught sight of myself in the mirror and admired the sight, surprised at just how the panties transformed my ass and made it look so much more feminine. I stroked my stiff cock gingerly through the soft, shiny fabric but stopped quickly. I was so turned on that I knew a few swift strokes would have me coming and I didn't want that. I wanted to enjoy and explore these new feelings and sensations, breaking the taboo of wearing women's clothes in such a delightful way. I pushed the top drawer shut and opened the next one down. Inside was rows of stockings and pantyhose, again in a variety of colours and styles. I ran my fingers over the piles of nylon and lace trim, feeling a sensation akin to picking up static electricity and inflaming my arousal further. From the top I picked up a pair of dark brown, semi- opaque pantyhose with an enticing glossy sheen and carried them over to the bed. I had seen enough TV and film footage of women putting on hosiery to have an idea what to do. I sat down and put my hand in one leg and gathered the material over it, marvelling at the way the nylon fabric gripped so strongly but at the same time felt so soft and insubstantial. I bent and put my foot into the toe of one leg before repeating the process for the other leg. It felt so sexy and sensual pulling the pantyhose up my nearly hairless legs, smoothing the material over them so they were seamlessly encased in clinging nylon. Once I was in the pantyhose and had them pulled over my hips, encasing my hips, groin and throbbing cock in a wonderfully slippery double layer of silky materials, I briefly considered what to do next. I thought of adding a bra or a slip or even a dress, but I found I couldn't. My breath was coming in short pants of arousal and my heart was racing. I sat back down and scuttled my butt back, resting my feet, legs open, on the edge of the bed with my feet pointed. I moaned softly in sheer pleasure as I ran my hands up my smooth thighs and placed the flat of my fingers over the bulge in the front of the panties. Slowly, delicately, I began to gently massage my stiff cock, smiling with delight as it occurred to me that I was masturbating just like a girl. I was so utterly transported by the situation and the sensation that I failed to hear my Aunt's car draw up outside the front door. I was startled when I heard the front door open and it took me several seconds for the clouds of pleasure to leave my head and for me to realise what was happening. I panicked as I heard my Aunt's heels clicking across the marble hallway floor. Instead of throwing on my discarded clothes and trying to hide, my startled brain decided I should remove the incriminating articles of clothing. I was torn by the need for urgency, as I heard my Aunt begin to ascend the stairs leading to the bedroom, and the need to not tear the delicate pantyhose. I had only got as far as pulling the pantyhose down my legs, the feet still caught on mine at my ankles, when the bedroom door opened. My Aunt stood there, eyes wide and mouth gaping at the sight of me on the edge of her bed. The pantyhose were still caught round my ankles and my hard cock tented the front of the satin panties, leaving no doubt about what I'd been doing. Aunt Lynnette only managed a stunned "What the actual fuck?" as I squealed like a startled animal and bolted for the door. I pushed past her and headed down the hallway for my room, the pantyhose still wrapped around my feet dragging behind me like the part-shed skin of a snake. It seemed to take forever for me to shuffle to my bedroom and open the door, my Aunt's eyes boring into my back as I went. Shutting the door behind me, I threw myself face down on the bed before finally removing my Aunt's clothes and tossing them into the corner. I sobbed into my pillow. What had I done? What would Aunt Lynnette do now? Would I be thrown out of her house? Even if I weren't, how could I ever pretend to be a man, with her catching me as she had? All these thoughts tumbled round my head as I lay there crying my heart out. I could hear my Aunt talking on her telephone. She had called one of her friends to share what she'd found and ask some advice. Her friend had suggested a minor punishment to deter this sort of behaviour in future, but they'd then gone on to dial-in several other friends. The women laughed and schemed, the minor punishment growing in scale and scope till it became totally life-changing for me. I lost track of time but, after an hour or so, my bedroom door opened and my Aunt entered without waiting for permission. She had a bundle of clothes over one arm and a pair of brown leather strappy sandals in the other hand. Standing by the bed, she spoke to me in harsh, disdainful tones. "I never want to catch you in my bedroom again, Steve, let me make that clear. I also don't want to see you naked again. Put these on," she commanded as she tossed a bra and a pair of panties on the bed beside me. They were made of a light blue cotton trimmed with light pink lace and ribbons, the sort of thing a teenage girl might wear, and an hour ago I would have eagerly put them on. Now, I was utterly terrified, unable to muster any defiance or resistance to my Aunt and slowly pulled on the unmistakeably feminine garments as if they would scald me. Once they were on, my Aunt told me to stand up and I complied, slouching in the middle of the floor, my shoulders bowed and my hands in front of my crotch trying to hide my shame. Aunt Lynnette told me to straighten up and I reluctantly did so. Once I was standing stiffly upright, she whipped out her phone and quickly shot a couple of pictures. "Now. Unless you want these pictures all over your school social media, you'll do exactly as I tell you. Clear?" she barked. On the verge of tears, I could only nod in compliance. She had me turn and adopt a number of coquettish poses as she took more incriminating pictures, even making me smile, pout and blow kisses for the camera. She handed me a pair of shiny white pantyhose and told me to put them on. I sat on the edge of the bed and repeated what I had done earlier with my Aunt's pantyhose. "You do that so well, it's almost like you've had a lot of practice," Aunt Lynnette sneered as she snapped a few more pictures of me pulling the pantyhose up my slim legs. More pictures were taken of me in the pantyhose before I was finally put into a blue cotton, sleeveless summer dress with a short, pleated skirt and a white floral pattern. I stepped into the brown leather sandals and posed a few more times for the camera. My Aunt had me sit down and took a few items from her pocket. Working quickly, and accepting no protest, she applied a sheen of glossy light- pink lipstick and some eyeliner and mascara. As I stood for my final photo session, I caught site of myself in the mirror. I could easily have been mistaken for a slightly younger teenage girl going to church on Sunday or a similar formal occasion. After a few more humiliating pictures, Aunt Lynnette spoke, "Well. Since you've kind of spoiled my evening out, you might as well keep me company for a night in," she smiled. "Come on, Stacie, let's go watch a movie." I flushed with embarrassment as I realised that she meant me. It seemed a very large step to have been given a new, girl's name too. I followed her out my bedroom and down the stairs and into the lounge. Aunt Lynnette stepped out to the kitchen and poured herself a glass of white wine and a white wine spritzer for me. She handed it to me with a smile and sat down on the sofa, patting the space next to her for me to sit. We spent the evening watching a period drama, not my normal taste in action movies, and Aunt Lynnette chatted amiably with me, explain the plot and characters as well as branching off into some other subjects. It seemed that, while she seemed to resent a male presence in her house, she was quite comfortable with the company of "Stacie." For myself, I felt happier and more relaxed than I had since I'd arrived, my shame and terror at the evening's earlier events gradually dissipating. Shortly after the end of the film, Aunt Lynnette excused herself and went upstairs for a few minutes. When she returned, she held out a hand and gently pulled me to my feet before speaking, "Well, Stacie. I've had an unexpectedly pleasant evening and I hope you have too. But it's time for an early night for you. We have an early start and a busy day tomorrow; we simply have to take you shopping and sort out your wardrobe. Now, I've put some makeup remover pads in your room, don't forget to clean that off eye liner, and I've laid out some new pyjamas for you. Goodnight princess," she said softly, giving me a quick peck on the cheek. A little flustered by her description of me as "princess" and wondering what she meant by "sort out my wardrobe" I bid her goodnight in return and headed upstairs. Once in my room I could see, laid out carefully on the bed, a candy pink babydoll nightie with a matching pair of skimpy panties. Now in private again, the thought of dressing in such a totally feminine garment began to excite me. I took off my dress and pantyhose and carefully laid them over the back of a chair rather than simply throwing them on the floor as I had normally done with all my male clothes. I took off the bra and panties and placed them in the laundry basket before eagerly dressing in the nightie and panties. Remembering my Aunt's advice, I stepped over to the dressing table and picked up the makeup removal pads. I took a last look at "Stacie's" prettily made-up face in the mirror before using a pad to wipe my face clean. The situation was all too much for me. I'd just taken off makeup and was now dressed in the most delicate, feminine nightwear. My cock was stiff and throbbing in the panties and could no longer be ignored. Carefully, I pulled the panties down, grasped my cock and, after a few swift tugs found myself coming longer and harder than I ever had before in my life. I cleaned my mess off the floor with some tissues. I now felt guilty and ashamed and wanted to remove the girly nightie and go to bed but I was scared my Aunt might come in to check on me. I remembered the incriminating pictures she had of me and realised I could not now step out of line in any way. I crawled into bed and fell into an exhausted sleep. I was woken in the morning by Aunt Lynnette coming into my bedroom with a tray of breakfast for us to share - coffee, croissants and fruit. While we ate, she chatted happily about her plans for the day, all the shops we would need to visit and things we'd need to buy. Of course, with the pictures taken the previous day there was no real way for me to object. I was also more than a little tongue tied as the situation and the caress of the pretty pink panties I was wearing had given me an erection. I was glad of the thick duvet I was under that hid my shame. As well as breakfast, my Aunt had brought in a change of underwear for me - a bra and panty set in light lavender lace with little purple flowers embroidered over them. She placed them on the bed and suggested I take a shower before getting dressed in the underwear with the dress, pantyhose and shoes I'd worn the day before. I did so and met her in the hallway before we headed into town. The shopping trip went more or less as Aunt Lynnette had planned. Her credit card took a heavy pounding as she happily purchased everything a teenage girl would need. We bought skirts, dresses, tops and blouses, girl's jeans, shoes, accessories and make-up. My Aunt encouraged me to choose items myself, advising me when she thought something wouldn't suit and suggesting items that she thought would look cute before sending me to the changing room to try them on. The shop assistants mostly knew my Aunt and were invariably helpful. Some of them clearly noted I wasn't what I appeared to be, although they cheerfully played along, while others gave no indication that they thought I was anything other than a pretty teenage girl being treated to some retail therapy. To be honest, I wasn't sure which made me feel more uncomfortable. Most of our purchases were held back for delivery to the house the following week, with us carrying home just enough items for me to use over the rest of the weekend. I had a moment of panic on the Sunday evening that Aunt Lynnette would send me off to school as a girl the following morning. However, that was not to be. I returned to school on Monday morning dressed in my normal boy clothes, although I couldn't help noticing how rough and uncomfortable they now felt in contrast to the light, feminine garments I'd been wearing over the weekend. When I returned home that evening, I found a change of clothes laid out on the bed by Aunt Lynnette and I eagerly stripped off and put them on, slightly surprised at just how eager I was to become "Stacie" again. From then on, this pattern became a routine. Monday to Friday I would go to school as Steve but in the evening and at weekends I was Stacie. At first it was embarrassing, even humiliating, being introduced, or re- introduced, to my Aunt's friends (both male and female) as Stacie when they came round to the house. However, after a while it became natural and nobody ever treated me as anything other than a teenage girl, most assuming that it was entirely my own choice to become a girl. An upside was that my relationship with my Aunt blossomed. I was quite happy helping her round the house, sitting chatting or watching a movie on the sofa together. We'd go out shopping or out for meals or to the cinema or theatre together. My Aunt seemed much happier with a niece in her home than she had with a nephew and was always ready with help or advice on clothes, make-up or my hair (which I had started to let grow out). On the downside, school became a real trial. I spent most of my time distracted, uncomfortable and waiting impatiently for when I could be Stacie again. It quickly began to feel like Stacie was the real me and Steve was an act I put on to go to school. I alienated myself from the few friends I'd made, deliberately avoiding and ignoring them. How could I meet them out of school or have them round the house where they'd see me as Stacie? I spent a lot of time looking at the girls at school, but it was no longer out of any real attraction to them. Instead, I watched how they dressed, moved and spoke so that I could better dress, move and speak as Stacie. As a result, I quickly got a reputation as a creep and a lecher making me even more of an outsider. This all, of course, made my school grades suffer. In turn, my hopes of going to a good college, or even going to college at all, began to recede. I started to stress about that. What would my Aunt do when I finished school for good? Would she hold to her promise and throw me out of the house, college place or not? If so, what would I do? How would I live? As it turned out, these were not issues that I really needed to worry my pretty little head about. A few weeks before the end of my final term, Aunt Lynnette announced that she'd had to let another of her assistants go. After my Aunt had seduced her, the poor girl had become intensely clingy" demanding a deeper relationship with her. Aunt Lynnette had not been prepared to give her that and the lovesick assistant had been summarily dismissed. Aunt Lynnette told me that she thought I would be ideal for the role, now that I was more than comfortable in a short skirt and heels, and that I would start on the Monday after the end of term. Of course, I could probably have protested, pushed the issue of college or simply left her house as her threats of "outing" me at school were no longer useful. However, I found the thought of being a sexy secretary, doing my Aunt's bidding around the office and helping her clients while dressed in woman's office attire and high heels, to be immensely arousing. I meekly acquiesced to her suggestion. The weekend following the end of school, I was taken on another shopping trip with Aunt Lynnette's credit card taking a beating once again. I'm happy to report, though, that this time none of the shop assistants thought I was anything other than a young lady buying a new wardrobe to start her first job. My girly lingerie was now supplemented with more sexy, adult styles. Bras, corselettes, camisoles, slips, teddies, garter belts and panties were purchased in silk, satin and lace and mainly black or bold red in colour. We bought pantyhose and stockings, again mainly in black, grey or nude, ranging from sheer to opaque. My Aunt helped me pick several new pairs of shoes and boots with much higher heels than I was used to, again mainly in black leather or shiny patent leather, but with a few red pairs too. To wear over this exquisite, sensual underwear, we bought a few women's business suits. Aunt Lynette complemented me on my long, slender legs and tight butt and insisted that most of these suits had short, tight skirts to help show them off. To go with these, we bought a number of blouses, mainly in satin or semi-transparent silk or lace. We did also buy a couple of pantsuits and two coats, one red, one black, for the colder weather. I was taken to a jeweller's and had my ears pierced and a couple of large hoop earrings fitted. Finally, my Aunt purchased a new pair of breast forms for me. I'd grown used to wearing a B-cup pair but these were now a D-Cup matching the new lingerie I'd been bought. Monday morning, Aunt Lynnette drove us to the office but dropped me a couple of blocks away at a caf? to collect our morning coffees and lunch order. In my tight skirt and towering heels I could only make small, dainty steps and I was acutely aware of how this must make my butt wiggle as I walked. I blushed profusely and shyly averted my gaze whenever I caught the eye of any of the smartly dressed guys in their suits looking at me. They were appraising me like a pack of hungry wolves with an injured prey animal and there seemed to be so many of them. On reaching the office, I discovered my Aunt had played a couple of "pranks" on me. Firstly, the stairs to the office led straight up to a pair of glass doors with my desk directly behind them. Unfortunately, my new desk was a modern design with a clear Perspex top and no modesty board. It didn't take me long to realize that every man coming to the office was pausing near the top of the stairs because they were taking in the view of my red panties and garter belt as this set up allowed them to look directly up my short skirt on their way in. The second prank was the name plaque Aunt Lynnette had made for me. It bore the company logo and the title "Receptionist" above the name "Stacie Swallows" that she claimed had been a mistake at the manufacturers and she would have rectified (but never did). Again, I quickly realised that the smirks from all visitors to the office were produced by them wondering if I lived up to that name. Apart from that, however, I soon settled into the role. It was just stimulating enough that I didn't get bored, but nothing was so challenging I could get stressed about it. For a few weeks, life continued in this vein and I was genuinely happy for the first time since the loss of my parents. I was Stacie now, sexy secretary in my Aunt's office, and barely remembered that I had ever been anything else. However, as things do, change came around after those few weeks. Mid- morning, on an otherwise normal midweek day, a new client arrived at the office. I didn't look up as he climbed the stairs but shifted a little uncomfortably as he took longer than most to admire the view of my long legs and stocking tops. I'd worn a bright red satin bra, garter belt and pantie set that day and my opaque black stockings had a wide lace top. I looked up and smiled shyly as he stood in front of the desk. He was of slightly above average height with an incredibly fit physique - broad shoulders, deep chest and narrow waist with strong, muscular thighs visible even through his expensive business suit. He had short black hair, a neatly trimmed black beard and dark, olive skin with penetrating dark eyes. "What a dish," I caught myself thinking before he spoke. He looked at the name plaque on my desk and smiled, "What a pretty name you have. Like the bird, da?" he asked in a strong Russian accent. "Something like that," I replied, blushing even deeper. Checking the office diary, I saw his name was Mr Oleg Stoyakovitch and he was scheduled to meet with my Aunt for the rest of the day. I stood and demurely smoothed my short skirt back down to cover the tops of my stockings before asking him to follow me to Aunt Lynnette's office. As we walked down the corridor, I could feel his gaze focussing intently on my ass and, I have to confess, it didn't feel at all unpleasant. My Aunt welcomed him and asked me to bring tea and, later on, lunch. They would be in negotiations for the rest of the day on a major new contract. At about half past four, my Aunt came out and told me to book a room in the Grand Hotel as their discussions were continuing but it was now too late for Mr Stoyakovitch to travel. At six thirty, they emerged from the office and shook hands formally. Aunt Lynnette asked me to call a cab to take him to his hotel. It seemed that their negotiations had not quite concluded successfully and that he would think it over overnight. He turned to me as we waited and asked, "As I am staying alone tonight, why don't you join me for dinner? Your boss has other engagements and has already seen enough of me for today, I think." I desperately tried to think of an excuse not to go while simultaneously thinking about how much I did want to go for dinner with this charming, handsome man. Aunt Lynnette chimed in, "Yes. That sounds like an excellent idea. Stacie didn't have any plans for this evening anyway," she told him, making me blush awkwardly. "Good. I will see you in reception in one hour." He smiled broadly and, without waiting for an answer headed out the door to get his cab. I turned, slightly stunned by what had just happened to my Aunt. "Well Stacie, looks like you've made a fan there," she smirked. "You know, if you treat him well you could probably swing this deal we're discussing. If you can get him to sign, I'll pay you a nice little bonus." Still shocked, I could only stammer, "Wh...what do you mean?" Aunt Lynnette gave me a mocking frown and said, "Come now Stacie. It's pretty clear he's keen on you. I fully expect you'll be invited back to his room after dinner. That's sure to leave him looking favourably at our firm afterwards if you go and entertain him." Again, I spluttered, "But...but...I'm...I'm not a..." "Don't worry, cupcake. Oleg knows exactly what kind of girl you are. That doesn't put him off at all. In fact, it probably makes him keener. You don't have to do anything you don't want to, but I'm pretty sure you'll enjoy yourself if you do and it will help our business to get this deal. Now, run along and fix your make-up, you don't have much time." Still stunned that I'd basically just been pimped out by my Aunt, I headed to the bathroom to reapply my lipstick. I headed down to the cab, still extremely nervous and unsure what I was going to do but I couldn't think of any reasonable excuse to not at least go to dinner as I'd agreed. Oleg met me at the reception of the Grand and escorted me to the bar for a pre-dinner drink before we went through to the restaurant. The drink help settled my nerves somewhat but mostly I was captivated by the charming man I was with. We chatted through dinner and I hung on his every word. At the end of the meal, he did indeed invite me to his room and I happily agreed to go. Once inside, Oleg removed his suit jacket and sat in one of the plush armchairs. "Why don't you slip off your jacket and make yourself more comfortable, angel?" he asked in his sexy accent. I did as he asked and put my jacket over the back of the other chair. I was suddenly overwhelmed by an irresistible impulse and I unbuttoned my blouse and took it off and added it to my jacket. Reaching behind me I unbuttoned and then unzipped my skirt before pulling it over my hips and letting it fall to the floor. Standing in front of him, I was glad I'd chosen such a sexy set of red satin underwear that day and I whispered hoarsely, "I think I'd feel more comfortable like this. If that's OK?" The wide smile and burning desire in his eyes told me that it was more than OK. During my time as Stacie, I'd steadily lost interest in girls, at least in a sexual way, and gradually become more interested in boys and their reaction to me. I hadn't really considered taking that any further though, I was too much enjoying discovering myself and my newfound femininity. Now, however, looking at Oleg drinking me in with his eyes, I knew exactly what I wanted. Slowly, seductively, I walked towards him and stood in front of him. Lowering myself to my knees, I gently parted his knees and ran my hands up his muscular thighs. It was like watching someone else at work as I looked at my hands unbuckling his belt, unbuttoning and then unzipping his trousers before drawing his stiff cock from his crisp cotton boxer shorts. I gasped in delight as I saw his cock was longer, and only a little thicker, than average and perfectly straight and well proportioned. Licking my lips, I raised myself a little and lowered my mouth on to his cock. I savoured the smell, the taste and the feel of it as I took it into my hungry mouth. What I lacked in experience, I think I made up for in enthusiasm. I sucked, licked, kissed and caressed his organ, exploring every inch with my tongue and fingers and didn't forget to give his balls some attention too. Judging by Oleg's reaction, moaning and thrusting his hips towards me, he was extremely pleased with my first attempts at oral sex. After several minutes, he gently pushed me back and smiled, telling me, "You are so wonderful, angel. But I would very much like to fuck you. If that's OK with you?" Of course, there was only really one reply I could give to that, "Yes. Yes that's OK with me. Would you like me on my back or on all fours?" I asked teasingly, eager to please him. "On your back, angel. I want you to see who's fucking you," he replied, his accent and dirty talk driving me wild. I stood and turned and dropped my panties, displaying my peachy ass for him. I wiggled it over to the bed and sat down, spreading my legs and pulling my knees back to point my eager asshole at him. He wasted little time in ripping off his clothes and walking towards me with his stiff cock bobbing intently for me. Taking some lube from a drawer next to the bed, he lathered it on his cock and gently applied some to my quivering ring before taking up a position raised above me, his straight arms supporting him as he looked down with undisguised lust. "Are you sure you want this, my darling?" he asked softly. "Yes. Yes. More than anything. Fuck me. Please fuck me," I panted, biting my bottom lip, He didn't need telling twice and, with a firm but gentle thrust he penetrated me. It was a little uncomfortable at first, I'd never been stretched like that before. However, with skilful slow thrusts of his cock and his gentle words of encouragement, I soon relaxed and was transported to a realm of pleasure I'd never known existed. After what seemed a long time, his thrusts sped up and his breathing increased in pace. "Oh, I'm so close, angel," he panted before taking his weight on one arm and using the other hand to reach down and stroke my cock. This unexpected increase in pleasure sent me over the edge and I came like never before, my own much smaller cock pumping out my orgasm and my tight anus contracting rhythmically around his hard cock. That, in turn, sent him over the edge and his cock stiffened further before twitching and jerking as it plastered my insides with his hot load. Afterwards, we lay together on the bed, Oleg on his back with an arm wrapped round me and me on my side with one stocking-clad leg across his strong thighs while my free hand gently caressed his broad, manly chest. He turned and kissed me gently but passionately. "Did you enjoy, my angel? Was it first time for you?" he asked softly. I felt a thrill that he was now calling me "my angel" and answered bashfully, "Yes, very much. And, yes, it was my first time." "Good. I'm glad I was first for you and make it nice. I hope it will not be our last time," he smiled. My hand moved down and gingerly stroked his soft dick, delighting me as it twitched and began to swell again. "Oh no. It definitely won't be our last. Not even our last time today." I grinned as I moved in to kiss him again. The next day, I turned up at the office late as I'd gone home to shower and change. I was not going to do the walk of shame into the office still wearing yesterday's clothes, that was just too much. Aunt Lynnette, however, knew exactly what had gone on and couldn't help herself from asking questions and making comments like "Did you have a good night last night, Stacie?" and "You look tired, honey. Not getting enough sleep?" I blushed and accepted the jibes, feeling quite deliciously slutty at the thought that she knew what I'd been up to. Mid-morning, though, she came out of her office and, smiling happily, informed me that Oleg had agreed to the contract and that it looked like I'd had a very successful "dinner date." When I checked my bank account at lunch, I saw a $5000 "bonus" payment had been made. I suppose I should have felt a little ashamed that I was now basically my Aunt's whore and had been pimped out to provide sex for money. However, I barely felt any embarrassment, and, in fact, the very idea made me extemely horny. After that, I totally embraced the "sexy secretary" aesthetic. Hems became higher along with heels, while the neckline on my blouses plunged lower. Make-up became bolder, eyeshadow smokier and perfume muskier and my nails became longer and redder, matching my full glossy lips. I often wore my hair up in a high ponytail or a smart bun, purely for the pleasure of taking it out and shaking it loose when an opportunity arose to tease someone I caught looking at me. Naturally, with a look that screamed "available" I did attract lots of male attention. I was asked out for dates lots of times, by the hot barista at the coffee shop, by the hunky bicycle courier and by many of the smartly dressed men in their business suits from the neighbouring offices. I turned them all down, politely, deciding a random date had to remain a pleasant fantasy with men who had not been briefed by Aunt Lynnette on the "type of girl" that I was. It became a regular event for me, maybe once, sometimes twice a week, to accompany one of my Aunt's clients out to dinner to help celebrate a deal that had been struck or to "persuade" them of the merits of doing business with the firm. I was fortunate that most of my Aunt's clients were handsome young or middle-aged men. Of course, there were a few that were older or heavily overweight or otherwise unattractive. However, that didn't deter me, and I went out with them all and never refused an invitation back to their room afterwards. I found that everyone had something. Something that made sex with them special and unique and enjoyable. I loved finding out who liked to give and who liked to receive; who was dominant and who was submissive; who liked a slow, sensual girlfriend experience and who liked to fuck like an animal; who was interested in bondage and discipline and who mainly wanted a cuddle and some shared intimacy they didn't get elsewhere. I even slept with a couple of my Aunt's female clients. While I enjoyed the experience immensely it made me realise that women were no longer really my thing, if they ever really had been. No, what I really liked was a strong, handsome, assertive man that would pin me down and make me his little fuck-bunny but that was also confident and caring enough to attend to my pleasure. In fact, if I had to name my ideal man, I would have instantly said Oleg Stoyakovitch. I was fortunate, then, that my Aunt's business with Oleg was highly successful and grew and expanded. This necessitated an increasing frequency of business meetings and my heart fluttered and butterflies formed in my stomach when I saw his name appear in the meetings diary. Soon he was visiting almost weekly. He also confessed to planning his meetings on Mondays or Fridays so that he could spend time with me over the preceding or following weekend. As well as spending a lot of those evenings and weekends in bed, he relished taking me out and showing me off and it was a great opportunity for me to wear sexy clothes that weren't women's business attire. We went out to bars and nightclubs, restaurants for dinner dates, movies and plays, even to museums and art exhibits and out for picnics. I loved every moment of pretending I was his wife or girlfriend. After about eighteen months of this very satisfactory lifestyle, I returned to the office after lunch and was surprised to see Oleg in a meeting room with Aunt Lynnette. No meeting had been scheduled and I became slightly concerned that something was amiss. After an hour or so, Aunt Lynnette came out and approached me and said, "Can you come in and join us, Stacie. There's something you need to be told," in a slightly curt way. I followed obediently, wondering if I had done something wrong and was about to be berated by my Aunt or, worse, by Oleg. I felt even more worried on entering the meeting room where I sensed that the normally calm and confident Oleg appeared rather nervous and unsettled. My Aunt cleared the uncomfortable silence. "Stacie, we have something to tell you. Oleg here has asked me for your hand in marriage and I have agreed to the match," she told me in a tone of voice as matter-of-fact as if she was reading a stationery order. I was momentarily stunned. It sounded like I had just been given away like a medieval princess to secure a marriage or a surplus Victorian daughter given away with her dowry. Oleg obviously sensed my discomfort and spoke, "That's...that's if you agree, of course, Stacie?" he said in a slightly hesitant voice. I thought for a moment more. I could probably have refused and walked out. It would have meant the end of my relationship with Oleg and, more than likely, my job with my Aunt but I now had enough money and work experience that I could deal with that. But did I want to? Would being married to a wealthy, handsome man, that was completely sexually compatible with me, really be a bad thing at all? "Yes. Yes, I agree. Of course, I agree," I answered, not needing to pursue my thoughts any further. Oleg visibly relaxed and his mouth split into a wide grin as he advanced towards me. He embraced me strongly before kissing me passionately and telling me, "I am going to make you the happiest girl in the world, my angel. The wedding will be in six weeks" time, at my mansion in Florida," he told me, before going on, "As well as my wife, I want you to be my assistant. We'll travel everywhere together, stay in the best hotels and eat in the finest restaurants. When we're not working, we can stay in one of my luxury villas or go on exciting adventure holidays, whatever you want," he almost gushed at me. Of course, as well as all that, I knew a big part of my life would be to provide Oleg with sex on call. I can't say I had any problem with that at all. After he released me from his warm embrace, Aunt Lynnette came over and wrapped her arms around me, kissing me on both cheeks - something she almost never did. She turned and did the same to Oleg before telling me, "Congratulations, Stacie, my girl. Looks like you've landed a keeper there," she winked. "Now, I think you should take the rest of the day off. I'm sure you two lovebirds will want to "celebrate" your engagement, I'll see you this evening for dinner and drinks." She turned and addressed me, "Stacie. The day after tomorrow I've booked you into a clinic for a set of breast implants, lip plumping and a few other cosmetic procedures. It's my wedding present to you both, I want you to just be the most perfect wife and secretary you can be. You can stay as a D-cup if, if you wish, but I think you'd be perfect with a set of double-Ds. I'll buy you some replacement lingerie to fit too, of course." It seemed this had already been decided too, without my input, but I barely even thought to protest. If this was what my Aunt and husband-to- be had decided, then I was happy to go along with it. As Oleg took my arm and led me to the door and on to his hotel to "celebrate," Aunt Lynnette had one last instruction. "Just before you leave, Stacie honey, there's just one more little job I have for you. Can you ring the recruitment consultant and let her know I'll need a replacement assistant? Please tell her to make sure she's cute, too," she smiled at us. So it was, that six weeks later, I took Aunt Lynnette's arm and she led me down the aisle between the rows of seats in the garden of Oleg's sumptuous villa in Florida. I was wearing a figure-hugging, long dress of purest ivory silk to show off my new curves. The front was cut low to show off my, now substantial, cleavage and a slit from the ground to mid- thigh revealed my white stockings and ivory silk covered shoes. My make- up was immaculate and my long hair had been styled up with a white veil half-covering my face. As we walked, I briefly considered that, even though this life would be far better than anything he could really have imagined, Steve probably wouldn't have chosen this path if he'd been offered it. However, that didn't really matter. Steve was gone, lost. Lost the moment he'd pulled on that first pair of satin panties, really. I had no regrets, though. I was Stacie, soon to be Mrs Stoyakovitch, and I was very much looking forward to everything my future held.

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Part 18 Sex with lactating secretary

Sajitha was a departmental secretary in our company. Upon my transfer or deputation to Mumbai as one might want to call it, she was assigned to me for some time in addition to her usual roles. While she did not belong to my department, half her time was to be with me. I was on an important mission to this office and I had clear directives as to what was expected of me. To work better I had requested for a helping hand to take care of the mundane matters like getting tea/coffee, taking meeting...

1 year ago
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Wizards Day Off The Secretary

The wizard sat on the park bench reading his paper. He was very much enjoying his day off. A man sat down next to him on the bench and forcefully dialed a number on his cell phone. He did not look happy but the wizard continued reading the paper, this was his day off after all. The wizard heard a squeaky voice on the other end answer and the man cut her off. "Britney, I am almost finished with my lunch break. Have you completed my report for corporate yet?" "What do you mean you are...

1 year ago
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Sissy Secretary

I guided them down the back staircase into the media room with its plush movie theater seats and a wall sized digital screen. My pride and joy, "And that," I said with a grand sweeping gesture and deep bow worthy of a carnival ringmaster, "is the tour of my humble abode." "Yes 'humble'," Maria Sanchez said elbowing her husband playfully in the ribs, "we should be able to afford so 'humble'. And here we thought living right off the golf course was nice." Her husband Ben defensively...

1 year ago
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application for secretary

Heather showed up at Margaret's office at nine sharp the next morning for her interview. I was in Margaret's office sipping at a cup of french vanilla cappuccino and Margaret was having a cup of coffee. Heather came in and introduced herself to us. She was wearing a very curly blonde wig that fell to the middle of her back, and she also had on a loose fitting white blouse, a knee length black skirt, white stockings and black five inch heels. Margaret directed Heather to sit in the chair by...

3 years ago
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Daddys Little Secretary

I recently was asked to become a partner at my law firm. Now, it’s not a very large firm maybe fifty or so attorney’s each of us have assistants and there’s about fifteen or so paralegals. We’re a pretty well knit family the majority of us have been working together for about a decade. As a matter fact my career started here before passing the bar. Before starting law school I was working as a paralegal for the firm. So, to go from a paralegal to a partner in just a decade is pretty...

3 years ago
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Georges secretary

My sweet girlfriend Laura looked upset during lunch time…I asked what problem she had and Laura leaned on the table, looked at me with her very nice green eyes and hissed:“George is cheating on me with that stupid bimbo secretary…”I insisted, asking her if she was sure or just she suspected the whole matter. But Laura then got even angrier and furious…“The bitch is the new girl in the office; I met her two weeks ago…”“A little slut bimbo in her early twenties; a sensual brunette, some killer...

2 years ago
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Rita my New Secretary

I'll start by telling you that this isn't a true story and began by telling you that I'm a small business owner and my name is Dave and I 'm the owner of a reality business and right in the middle of our busiest time of the year my secretary Lisa comes into my office one morning and tells me she's giving her two weeks notice as she's accepted another job offer that Offers more money and is closer to home!! So the next day I place an add in the classified's section of our local paper advertising...

3 years ago
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Black Politician Breeds Married White Press Secretary

Race relations in the United States have improved markedly since the 1960s, although some blacks and whites still have lingering prejudices, especially in the South. I’ll admit that even being born in Alabama in 1988, and raised in the 1990s and early 2000s, many of my family and neighbors still held resentments from the racial strife in the 1960s. I tried to rise above those influences, but it was difficult.My name is Avery, and after high school I attended a moderately-liberal college in...

Interracial
1 year ago
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Stripper to Special Secretary

I really need a job. It has been two months since I was fired from my last job as a stripper and I am running low on money. I was let go because the place I worked at, Dancing Dames, was not doing well and they needed to let half of their workers go. I have looked at other strip clubs, but I want to try something new. Work though, has been hard to find, considering most of my experience is in taking off my clothes and giving lap dances. So over the weeks I have become more and more desperate...

Office Sex
1 year ago
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Banging My Horny Secretary

Hello ISS readers. This is my third story on ISS and in this story i am going to tell you about the experience about how i got to fuck my extremely hot and mature secretary. We had shifted to Singapore two years ago and after joining the office, i first met her. My boss introduced her and told that she was to be my personal secretary. She was a beautiful woman, about 38 years of age, not so fat. Her assets were beautiful. She had a nice pair of round breasts and a firm tight ass. She was...

2 years ago
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The New Secretary

The New Secretary (inspired by Masked Scribe's The Secretary from the yahoo maskingwriter group) Eric Lindsey got up, struggling to get open his eyes. But when he saw the time-1120am, he got real quick. Oh crap, I am nearly late for my next interview this afternoon. He leapt out of bed and after taking off his sleepwear, he gathered his materials for the interview. Sure, the last job he had was fun and all, but he yearned for more excitement. There existed a thrill to becoming a female...

1 year ago
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Secretary

Secretary1        It was Friday near quitting time when the E-mail showed up from my boss.         Kelly,        I think this would be a good time for you to invest in some job security, come into my office and be prepared to learn all of the tricks to being an exemplary subordinate.         Mr. Blalock had been hinting since he had hired me that I should be doing him in order to keep my job.  Unfortunately, just as with the E-mail I had just received his hints were just vague enough that...

3 years ago
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From Salesman to Secretary

Chapter 1: Reunion "Hey James, you ready to interview this new secretary?" James looked up from his laptop and saw Dave, his boss. "I'm a bit swamped right now, would you be up for doing it solo?" he said to him. He had been working full on all day but was ever so slightly behind. "Sure, thing no problem, you keep doing what you do best!" And off he went. Dave was a tall handsome man that made a good boss. He wasn't too tough and he had a very friendly attitude, it made the...

1 year ago
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My hot Secretary

Miller and sons. The 3rd largest law firm on the west coast. I've worked for the firm the past eighteen years. Started out in the mailroom at seventeen years old. Why might someone get into law you ask? Because my father did it. And so did my grandfather. I was holding court in my living room at age ten. Didn't really have much chance of being anything else. I wanted to be a rock star. But there is the problem of needing musician talent. Which I didn't have. There's always a catch. By...

2 years ago
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Julie the secretary

A fantasy inspired by amateur_julie containing office related frolics...My job sees me travelling around the country on a freelance basis going to various companies fixing IT problems as and when they arise. I'm never in any one place longer than a week. It's not the sort of working life that everyone would take to - hardly ever seeing the same faces, but it suits me as I can choose to work when and where I need to. A few months ago my agency sent me to a company not far outside of London for a...

4 years ago
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Kelly Woods The Young Secretary

Kelly Woods needed this job desperately. Her husband, Todd, becameanother victim of the worst economy since the Great Depression. With onlyher income now, the newly married couple barely made their rent and carpayments. If she lost her job too, eviction from their apartment andrepossession of their car threatened to leave them destitute. Fortunately,John Simpson, the owner of Franks and Simpson Marketing where she worked,was a kindly old gentleman who liked her. Although others...

3 years ago
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Master Johns Sissy Secretary

Master John's Sissy Secretary by Melissa FCD The intercom buzzes and my boss's voice booms out loud and clear. "Melissa I want you in here in ten minutes to take dictation. And bring me some coffee." "Yes sir Mr. Thomas, I'll be in there in ten minutes with your coffee sir" I reply. I get up to make a fresh pot of coffee. As I walk to the coffee maker my suntan colored nylons rub against each other at my thighs making a soft whispering sound. My four inch navy pumps...

1 year ago
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A Special Secretary

I look up as the suave middle-aged man waltzes into the office, suit immaculate and just enough stubble to appear roguish, but not unkempt. "Rogers. Harrison Rogers," he says to me, frowning slightly. He is surprised - they always are. Why on earth would a successful businessman like Gerald Hammersmith have a male secretary, after all? I watch as Rogers's eyes narrow, then he gives the usual slight shake of his head, and then a shrug. They all go through the same thought process: is...

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