11 comments/ 172255 views/ 48 favorites SEXretary By: sexy_jessie Sam Nichols had a comfortable, reasonably well paid job in a computing firm called Stewart Computing. He was twenty two and had recently graduated college and had been lucky to find such a good job in the firm on the edge of San Diego, just a couple of hours drive away from where his parents still lived with his younger sister Lizzie in the small town of River Falls. When he was growing up Sam's parents had known Henry Stewart, the owner of Stewart Computing who had lived in River Falls until he had been divorced by his wife and had moved out when Sam was about sixteen. That had been the last Sam had seen of Henry Stewart as his parents were better friends with Henry's wife, Sadie, who stayed on in River Falls with Henry's three sons, the eldest of whom. Brad, had been at high school with Sam. Although he hadn't seen Henry Stewart in six years, Sam had the impression that this family connection was what had secured him such a comfortably lucrative job. Sam was a quiet, introverted person who hadn't had a girlfriend since Britney Walker in High School and lived alone in a sparse little apartment on the outskirts of San Diego not far from the offices of Stewart Computing. Sam was a small and quiet person, barely noticed by his colleagues among whom he hadn't made any close friends. His life followed a dull, regular routine of long days at work then an evening alone in the apartment, watching TV with a cheap take-out meal. Every Sunday he drove the two hours to River Falls to have dinner with his family. Sam thought himself satisfied with this routine if not greatly happy. However, one quiet, dull Thursday afternoon at the office his life was completely turned upside down. There was a knock on the wall of his cubicle, Sam felt his little, enclosed cubicle to be his own personal space where he could be safe against the world outside and he wasn't entirely happy about it being invaded. He looked up to see his boss, Jemma, who smiled at him: "Can you come into my office a moment, Sam?" she said. Sam felt a sudden rush of nervousness run through his body, what could he have done to cause Jemma to be angry? Or maybe she was going to offer him a raise or a promotion? Thus it was with a mixture of anticipation and worry that Sam followed Jemma through the outer office where her PA would normally be but which was now empty and into Jemma's own plush, large office. Jemma motioned for Sam to sit down in one of the large comfortable chairs in front of her sturdy wood desk on which glistened a silver name label reading "Jemma Stevens" as she sat in her high leather chair on the other side of her computer and started to talk to him. "As you may or may not know Sam," Jemma began, "We've been doing a routine de-bugging of all the company's computers and discovered a huge bulk of memory taken up on yours," Sam gulped, he felt now that he knew what this was all about and he wasn't liking that thought, "I decided to give it a closer investigation and can you guess what I found?" Sam was stunned silent, he didn't know what to say or how to react under his boss' glare, it felt like an age as Sam, already not the tallest of people, shrank back into his chair as Jemma stared, seemingly calm and serene, over the top of her stylish, small, titanium rimmed glasses. After what was probably only a couple of seconds, Jemma decided to answer her own question by turning the screen towards him. Flashing up on the screen were a selection of the photo and video files that had been taking up the large amounts of memory space on his computer, but Sam didn't think that using company time and company computers was the biggest issue here. The images that were flashing up in front of Sam were the images of his slowly and carefully accumulated stash of internet pornography. Timid and shy, Sam found the only release for his pent up sexual urges to come from using his time when nobody else was around in downloading masses of pornographic material and then retiring to the men's room to jerk off over it. Deep down, Sam must have realised that eventually this habit would catch up with him and he would get caught but he couldn't stop himself. "Imagine my surprise when I found what it was that was taking up all your computer space," Jemma continued, "Who would have thought that quiet, retiring Sam would be the one to get caught for this." The images, initially mostly made up of naked women and scenes of men and women fucking, gradually evolved into more and more lesbian pictures and then went further into pictures of crossdressers and shemales, stripping off to reveal the secret hanging between their legs, fucking women and fucking and being flicked by men. As the screen showed deeper into Sam's internet explorations and deeper into his growing perversions and fantasies, he felt himself shrinking even farther back and becoming ever more red with the embarrassment of the situation. "Obviously, Sam," Jemma said to him with a seriousness that worried Sam very much as she turned off the slideshow of porno images, "There's no way that you can continue working for Stewart Computing in your current position. Normally in this sort of situation, the company policy is simply to fire the person involved, but you're in luck. My PA has just quit and I need someone to fill her shoes fairly immediately. It's not a taxing or difficult job and the pay is a fair amount less than you're used to, but let's face it, it's the best offer you've got. Besides, there are plenty of ways of picking up a few bonuses with the job," at this Sam was sure that he saw Jemma wink seductively at him. Sam felt a slightly worrying stirring in his groin at this thought, the, albeit very brief, sight of some of the sexy images from his computer didn't help this feeling either, nor did the fact that Sam had, once or twice before, fantasised about situations where he was dominated by his boss. Jemma was only about six or seven years older than Sam but had rapidly risen to become the company's chief executive, despite founding the company Henry Stewart was never seen there any more and just reaped the financial benefits. Jemma was generally quite commanding and stem but was definitely a good boss and, despite her generally hard attitude, could be understanding as well. Although not absolutely gorgeous, Jemma was quite attractive, with a slender, well proportioned body and blonde hair cut in an expensive, short style. She carried herself in such a confident way as to seem especially sexy and her firm, uncompromising style was something that attracted her to Sam in his dreams and fantasies. The thought of a woman who was generally rather asexual in the workplace and kept her personal and work lives separate flirting with Sam was quite a shock and especially after she had essentially fired him. Even though he saw that seductive wink, he wasn't sure he believed it. Still, agreeing with her assessment that he couldn't do any better, Sam humbly agreed to take up the job as Jemma's PA. Jemma gave a big smile. "Excellent," she said in a slightly seductive voice he had never heard her use before, "Come over to my place around eight this evening and I'll help prepare you for your new job," here Sam was absolutely certain there was another seductive wink and he agreed readily to her proposition, thinking eagerly of what she could be after from him. Jemma handed him the address of a swanky apartment in San Diego and said, "Now, clear your desk, I want you gone 'from your old job by three, and don't tell anyone about this." *** That evening, Sam made his way to the luxury apartment address that Jemma had given him, not exactly knowing what to expect from the evening but definitely excited by the prospect of what Jemma could be wanting from him. At five minutes to eight he rang the bell of the apartment block and Jemma let him in, he knew that his being early would show his eagerness but there was nothing that he could do about that. The apartment block had an elevator up to the high floor where Jemma's apartment was but Sam decided to take the stairs to calm his nerves. Jemma answered the door dressed in a blouse and knee length skirt, she smiled briefly and ushered him into the living room which was designed in a sumptuous, feminine decor that Sam felt was a little incongruous with Jemma's hard edged personality. There were a number of soft, plush sofas in shades of pink and red and one wall was almost entirely made up with full length mirrors that made the opulence of the room look even grander. Sam had assumed that for whatever he and Jemma were going to do they would have the apartment to themselves, however now he heard the sounds of somebody moving around in the next room. He began to realise how little he knew about his boss outside a work environment, for some reason he had assumed that Jemma lived alone and the discovery that she didn't was quite a surprise. The door to the next room opened and in came the apartment's other inhabitant. "Sam, this is my roommate Helena," Jemma introduced them. "So," Helena said in a sensual purr, seeming to size him up, "You're the new secretary," she smiled at him, licking her lips. Compared with the hard edged Jemma, Helena was far more overtly feminine and sexy and Sam guessed that the apartment's decor was her responsibility. Although she seemed about ten years older than Jemma, Helena was certainly the more naturally sexy of the two, tall with long smooth sensual legs, feminine curves and large breasts, Helena also dressed in a way that enhanced her sexiness rather than covering herself with the business like exterior which Jemma did. Helena was wearing a pink sweater with a very low-cut v-shaped neckline that showed off her cleavage and clung to the curve of her breasts while her legs were equally well revealed by a very short blue denim mini-skirt. She had stylish, long blonde hair and large, scarlet lips that she had a habit of licking seductively and eyes that had a naughty twinkle as if she was always thinking about something kinky. She sat down on one of the sofas and stretched her long legs out, lounging seductively so Sam saw a glimpse of the pink panties she was wearing beneath her denim skirt. Jemma ushered Sam to sit down as well and then brought all three of them glasses that contained a colourful red cocktail that tasted sweet and fruity and slipped down very easily so that in just half an hour Sam was already feeling a little less in control of his actions. Conversation was flowing as freely as the alcohol, but Sam was feeling a little uncomfortable and a little unsure of himself, he didn't really know quite what was going on here, his boss had invited him to her apartment, surely something was going to happen. Jemma seemed to remember that there was a reason for him being here. "Oh, yes," she said, "Sam, we need to get you 'trained' for your new position," here Helena giggled but Sam wasn't sure why, "I think we'd better start with the dress code," here she winked at Helena, "Come with me." She took Sam by the hand and took him into a bedroom, by his furnishings slightly less luxuriant than the living room Sam guessed it was Jemma's own and he began to become a little excited and aroused. This situation wasn't exactly helped by the fact that on the double bed some very sexy lingerie and clothing that Sam knew Jemma wouldn't normally wear was laid out. Sam turned expectantly towards Jemma and Jemma smiled at him and nodded her head towards the clothes laid out on the bed as Sam felt his cock twitch in anticipation. "While you're working as my PA, Sam," she said, "I'd like you to dress like that." Sam felt his mouth dropping open in surprise and was for some time slumped completely for what to say, not for the first time that day. He laughed nervously: "You're joking right," he said in a way that tried to sound confident but actually felt a little desperate. "This isn't the sort of thing I joke about, Sam," Jemma said seriously and sternly, "I need to have a female PA, our investors demand it, besides, we can't very well have you seen around the office after you've been fired now can we? What would people think?" Sam didn't know what to say to this either or how to answer her, she was right of course about him not being able to return to work as his current self after being fired, and he knew that she'd seen the contents of his computer which meant she'd seen his large numbers of photos and movies of transsexuals and shemales and knew he must be curious about that sort of thing. Still Sam held back a little longer, the situation was so strange and uncomfortable he really didn't know what to do at all. "It's not like you have any other work options, particularly after the sort of reference I could give you," Jemma continued sternly, "You have to pay the rent somehow." Maybe it was Jemma's stern, commanding but reasonable arguments that came out almost like commands. Maybe it was Sam's own curiosity and sexual urges from the frankly arousing situation. Maybe it was Helena's sexy, suggestive and encouraging smiles. Maybe it was the amount of cocktails he had drank earlier. Sam didn't entirely know the reason why or how it had happened, but half an hour later he found himself totally stripped naked by the two women who were shaving off all of his body hair. It was certainly an odd and unusual situation to find himself in but Sam couldn't help, in amongst slight feelings of shame, but be a little turned on by it. Jemma was, as always, controlling, serious and business like as she directed both him and Helena with what they were doing while Helena was light and giggly, seeming to see the whole thing as a big joke. With the help of the two women, neither of whom was reacting like the situation was as strange as Sam was thinking it was, Sam slipped into the sexy lingerie and Helena filled the cups of his bra with some very convincing prosthetic breasts. Having dressed fully in the sexy girlie outfit that Jemma had laid out, Sam oddly began to feel more comfortable. There was something about the new-found smoothness of his skin and the silky soft sexy underwear that was both arousing and strangely natural. He felt oddly as if this was somehow the right thing for him to be doing and he began to relax a little and enjoy the feminine feel of being totally fussed over and pampered by the dedicated attentions of these two women as they tried to make him look his best. When they had applied a liberal amount of make-up and a blonde, feminine wig, Sam could really see how successful their efforts had been. In the tall, full length mirrors he could see himself, or at least he had to assure himself that it was really him because what he really saw was a sexy, girlish woman at least a match for Jemma. *** The next morning was Saturday and Sam awoke feeling groggy and hungover from all the cocktails of the night before. He had an uncomfortable feeling that the previous night he had done something that he wouldn't be proud of now, in the cold light of day. He also had no idea how he had managed to get home. Desperately he tried to piece together the events of the night before to remember what he had done. There was a stain of lipstick and mascara smudged across the pillow and Sam briefly wondered if he had finally managed to bring a woman home to his less than luxurious apartment. A moment's consideration and remembrance banished that thought from his mind as he felt that he certainly wasn't dressed in his usual night-clothes. Throwing the duvet off his bed, Sam looked down at himself and some of the memories of last night came flooding back to his mind. He was still dressed in the tight, sexy woman's clothes of the night before, his legs, smooth and shaven, tingled with pleasure and his cock, encased in its satin lingerie panties was feeling better than ever. His panties were slightly hard and stained as was part of the skirt with his cum, he still couldn't remember when he had done that, whether it was at Jemma's apartment or here, and how he had got back here anyway. The last thing he could remember was looking at his reflection in one of the full length mirrors in Jemma's apartment, he remembered thinking, even through his blurred, hazy, drunk vision, that the woman looking back at him was pretty hot, and then Jemma's sexy room-mate Helena had offered Sam another drink and he couldn't, for the life of him, remember anything that had happened afterwards. Sam got up and went into the bathroom to examine his reflection. His cock twitched for a moment at the sight before he reminded himself that it was just his own reflection. If anything, in the cold light of day Sam's sexy girlish look was even more convincing and enticing now no longer blurred through an alcoholic haze. Sure his make-up and lipstick was smudged and his well styled blonde wig was now a mess, but Sam felt that this dishevelled look simply gave the sexy young woman looking back at him a touch of naughtiness, like she had just been interrupted in the middle of seducing a man. After a moment's thought, Sam decided that before he even began to think of a way to get himself out of this situation and to sort things out with Jemma he would have to wash the cum stained clothes she had dressed him in. He felt that he could take a decision about where to go from here and what to do as the clothes washed. Sam felt a moment of disappointment and regret at taking off the tight skirt and slipping the soft lingerie from his cock and legs. His old, masculine clothes seemed distinctly unappealing right then and, instinctively, he turned from putting them on, thinking them ugly and uncomfortable, and, instead, wrapped his smooth, hairless, feminine body in a bath towel that allowed the full length of his shaved legs to be on show. In taking off the bra that Jemma had given him, Sam discovered something else that he couldn't quite remember from the night before. He had expected that the convincing false breasts that Jemma had stuffed the bra with would simply slip off along with the bra, and he was certainly surprised to say the least when he found them still attached to his chest. Somehow, at some point of the night that Sam could not remember, Jemma and Helena must have stuck the silicone breasts to his chest. He tried in vain to pull them away for a few minutes but they were well attached. Before he knew it, instead of trying to pull the breasts free he was stroking and caressing them and he noticed his erect cock poking out from the towel he was wrapped in, excited by the thoughts that were running through his head. Sam had to admit, looking down at his whole smooth naked body, with the towel dropped to the floor, that the curve of the largish breasts against his chest was not only convincingly real but also quite a turn on. For a few minutes, Sam's thoughts didn't rest at all on the need to remove them or the complications this added to his desire to get rid of this whole incident. Instead he sat down on top of his washing machine as Jemma's sexy, feminine clothes spun round inside, and began to jerk off his erect cock, enjoying the pleasure of the machine's vibrations and very quickly blowing his load across his chest and up towards the false breasts. It didn't take Sam long after that to have resolved in his mind the complete opposite of his earlier desire to return the clothes and return to his old life. He knew that he really did need a job, his rent money was due in three days and he couldn't stand to lose his job now, he also knew that Jemma could make it hard for him to get one somewhere else; she had told him as much the night before. She was also right when she had said that they couldn't just fire him and then have him appear once again as her PA so he would have to assume a new identity. Besides, for now at least, he was enjoying exploring, at least in private, the new avenues that his feminine looks and attributes could bring him. Thus, Sam decided, at least for now, that not only would he take up the job of Jemma's PA, one far less important than the one he had before, but that he would also do the job, not as himself, but as a sexy woman. SEXretary This decision made, Sam felt as if a load that had been hanging over him had gone and he could now get on with thinking in greater detail about the specifics of the matter. Taking a shower to rinse his cum from his body, he washed the make-up off his face and brushed his wispy blonde wig back into some sort of style. Even without the make-up, Sam was surprised by how easily convinced he was of his own femininity. The elegant and sexy blonde wig, as opposed to his normal short dark hair, framed his soft features in such a way as to bring out their girlishness and the image as a whole was helped by the obvious protruding breasts that Sam was becoming increasingly comfortable with. If he was going to go through with this transformation and go to work as a woman then he would have to go all the way with it, he knew that right from the beginning. There was no use making a half-assed job of it and the deception being obvious. His true identity if discovered would be far more embarrassing than having to work as a woman and only him and Jemma knowing the truth. As a result of this thought, Sam spent all day Saturday in working on every aspect of his femininity so as to be fully able to convince when he started his new job on Monday. When the cum stains were washed from the clothes that Jemma had given him and the clothes were dry, Sam put them back on and wore them for the rest of the day. He was quite surprised at how immediately satisfied and at home he felt in putting them back on and his old masculine wardrobe seemed even more unattractive now. All day Sam practised learning to walk, to move, to sit and stand like a woman would. Everything he did from eating his meals to brushing his teeth he tried extra hard to do exactly as he felt a woman should. He sat for a long time in front of the mirror, simply practising and perfecting his womanly voice and mannerisms, both of which he, almost subconsciously, based on Jemma's room-mate Helena, one of the most sensually feminine and womanly people Sam had ever met. He slept that night naked, the sheets on his bed feeling soft against his shaved, hairless skin, not wanting to damage his only outfit of womanly clothing. The following day, Sunday, Sam decided, although he was very nervous about it, to leave the apartment and go to the mall. He knew that he had to try out his new feminine persona around real people to finally perfect it, both to see whether they all bought him as a sexy woman and to observe real women dad hope to be able to act more like them. More than this though, Sam knew that, if he really was going to dedicate himself to this and to working the job for the foreseeable future, then he would have to get himself more than just the one set of female clothing, not to mention accessories like make-up and jewellery that were vital to him convincing as a normal woman. He put on the black lingerie bra and panties that Jemma had given him along with the knee length skirt and white blouse. Brushing his hair in front of the bathroom mirror, Sam noticed that there was a lipstick that had presumably been left there by his sister Lizzie when she had stayed with him one weekend, she didn't wear make-up much so probably wouldn't miss it. Knowing that any help with making him more feminine would be a bonus, Sam carefully applied the pale red colour across his lips and smiled at his reflection, pleased with how effective the lipstick was in further feminising his features. Lizzie's lipstick also served to remind him that he was supposed to be having lunch with his family back in the small town of River Falls that day. He knew that he couldn't go like this; in fact he knew that while he was trying to live and work as a woman he probably would have to find excuses not to go there, he didn't know how his family would react to the news. Sam resolved not to think any more about the worries that aspects of his new job could bring and set out from his apartment to go to the mall. Nervous at first about whether he would be spotted a mile off for the fraud that he was, Sam gradually became increasingly confident in his femininity as he walked through the mall and became used to walking and acting in a ladylike way around people. In fact, although occasionally Sam noticed people staring at him as he felt momentarily self-conscious, he quickly noticed that the stares weren't accusational but were rather stares of guys who looked on with ill disguised admiration at the woman walking by. As he began to realise this, Sam allowed himself a little smile, both pleased at how able he was to pass himself off as a woman and, even though he struggled to admit it even to himself, a little flattered at the rapt attention of these guys. Without even realising it, Sam added a little bit of a sway to his step and thrust his pert little ass out farther. The shopping itself was also quite a success, despite Sam's initial confusion at women's clothing sizes and his embarrassed difficulty at trying to choose what clothing he thought would look and feel good on him. In fact, it wasn't long before Sam had assembled quite a wardrobe of various new outfits of skirts and dresses, tops and blouses and, once again, he felt an increasing confidence as he went farther in with it. After his initial difficulty with sizes, Sam was pleased to note that, because of his small, effeminate size and stature, there wasn't any problem in finding clothes that fit him, although he tended not to want to try them on as he felt a little afraid of the look and feel of the clothes provoking an arousal in him right there in the shop. Laden with various bags of clothes in his hands, Sam turned into a shoe shop in a less busy corner of the mall. Sam was not a rich person and he had already spent more on women's clothes that day than he had on men's clothes in years, yet he felt that he absolutely had to have at least one pair of sexy, feminine shoes as Jemma hadn't provided him with any and he was now just wearing a pair of sneakers that were a little incongruous with his sexy new wardrobe. In his previous shopping experience, shopping for guy's things, Sam had never enjoyed shopping, he had always hurried to the shop, grabbed anything vaguely suitable and gone home. Now, however, he was feeling a new joy to everything as if shopping had become a whole new experience now he was doing it in the form of a woman. Certainly shoe shops had never held any interest to him before, but now, looking in the window at the huge array of different sizes, materials and colours that Despite this fact, he wandered into the store, knowing he needed sexy shoes and hoping for a slightly cheaper pair. He scanned along the seemingly endless rows of various kinds of shoes and saw two more that were, if not quite as suitable as the knee-high PVC boots, at least pretty sexy. The first was a pair of scarlet coloured pumps that Sam knew would be just perfect for the sensual, sexy side of his new feminine persona. The others were strappy black sandals with a silver buckle and six inch heels, Sam had never worn heels before, until a couple of days earlier he had never worn any kinds of women's clothing before, but they called out to him. He had heard women say that wearing heels would enhance the length and curve of their legs and make them walk in an enticing swaying way. He also knew that the part of him that was still masculine really liked to see a woman in tall heels. He looked around for a sales assistant to get to try the shoes on and his nerves came flooding back for a moment as he realised this would be the first time that he would have to use his new feminine voice to speak any more than thanking people in earlier stores. He saw a guy come over in one of the store's name tags and he flashed the guy a flirty smile of his red lips and white teeth to try and put both himself and the guy at ease. "I'll try both of these," he said in his best imitation of Helena's throaty purr. The sales assistant didn't bat an eyelid at this, not finding anything unusual in an attractive young woman wanting to try on a sexy pair of shoes, and walked into the storeroom at the back of the store to get the two pairs that Sam wanted to try. Meanwhile, Sam went and sat down on one of the store's chairs to wait for him, crossing his legs in a ladylike way so one of his smooth legs dangled in front of him and removing his un-feminine sneakers. Putting the sneakers aside, he looked back up to see the sales assistant walking back over. Now he was feeling a little more at ease, Sam felt able to have a look at the guy, to size him up. If Sam were the petite, sexy young woman that he was pretending to be then he would surely have felt attracted to this hunky guy. He looked pretty young but already was around six feet tall and his tight shirt failed to hide the rippling muscles across his chest and arms. As he came up to Sam, Sam suddenly realised there was something familiar about his perfectly chiselled square jawbone and attractive face. For a moment Sam couldn't think where he knew this muscular hunky guy from, but then he realised. It was Brock Stewart, the youngest son of Henry Stewart the owner of the company that Sam worked for. Sam's mother had been friends with Brock's when they were much younger and Sam had been at high school with Brad, Brock's older and much less athletic and sporty brother. He remembered Brock as being the leading jock in his sister's year at River Falls High School. Now eighteen and in his senior year, with Sam's sister Lizzie, Brock was the captain of the football team but was working weekends at the shoe store in order to earn some extra cash since he lived with just his mother. "Here you are," he said, smiling at Sam in a way that suggested he was feeling a little bit attracted to this good looking young woman he had to serve, "What did you say your name was?" Was he trying to flirt with Sam? Sam felt butterflies of nerves in his stomach but a rush of excitement and pleasure that such a good looking guy would pay him such attention. "Sam. . . .antha," he said, with a sort of stutter, "Samantha Nichols, I think you go to school with my sister," he said to try and change the subject. "I do?" Brock's face went blank for a moment as he tried to think of the sister. "Lizzie Nichols?" he said, "I didn't think she had a sister." Sam was tongue tied as he suddenly realised that he could have just revealed his secret in such a clumsy way, "Sh. . she's my half sister," Sam stuttered an explanation, "I. . I don't live with her parents." Fortunately for Sam, Brock wasn't too bright and he seemed happy to accept his explanation without going into too much questioning of it, or maybe the alternative was something he couldn't really comprehend. Anyway, Brock accepted this as the truth and smiled again at Sam. "Well Samantha, I must say you looks certainly do stand out somewhat more than hers do," he said as he slipped Sam's dainty feet into the red pumps, "If you don't mind my saying so." Involuntarily, Sam felt his cheeks flush as red as the shoes with this compliment. He tilted his head to one side, batted his eyelids and smiled back down at him. "It's very sweet of you to say so," he said, bringing his voice back under control and back to the sexy, throaty voice he had perfected just the day before. Sam initially felt that he had begun to be friendly with, and even to flirt with, Brock because he felt that it would allow his secret not to be discovered, but increasingly he found himself enjoying flirting with him. Almost involuntarily, Sam found himself giggling and smiling at everything he said and leaning forward to let him see the curve of her breasts. As a guy, Sam was serious and thoughtful, but as Samantha he felt he could break free from that and be giggly and light and fun. As he walked across the store, to try out the scarlet pumps he deliberately added an extra sway in his hips and was rewarded by a momentary silence from Brock as he stared at Sam's ass as Sam walked away from him. "I really don't know which of these shoes would suit me best," he found himself asking in an increasingly fluttery voice, "What do you think. Brock?" "I think anything would look good on you," he said, smiling at his slightly laboured compliment. Brock wasn't the cleverest or wittiest flirt in the world but Sam wasn't very experienced at flirting with guys anyway so he didn't mind that, he was having fun. As Brock helped slip Sam's right foot into the strappy sandals and clasped the silver buckle, Sam noticed a slight bulge in Brock's pants, obviously Brock was enjoying this close contact and flirty conversation with a sexy woman. When Brock wasn't looking Sam allowed himself a smile at the effect that he was having and, when he put the other foot forward for Brock to slip the shoe onto, he deliberately uncrossed his legs in such a way as to allow Brock to peek up his skirt and get the briefest of glimpses of the black panties beneath. Sam allowed himself another slightly smug smile as Brock stopped mid sentence and simply gawped at him. However it was Sam's turn to be embarrassed just a few moments later when he stood up to try to walk in the new shoes. Having never walked in heels before, Sam didn't really know what to expect and, as he tottered forward on the tiny six-inch spikes, he completely lost his balance and his legs flew out from under him. Sam fell flying backwards and may well have ended sprawled out on the floor with his head cracked open, how would he explain his outfit then?, had Brock not caught him as he fell backwards. With his petite, frail, feminised body held, cradled, in Brock's masculine, muscular arms, Sam felt safe and re-assured. He felt at that moment totally in Brock's control and he was enjoying that sensation. He gazed up at Brock's strong, masculine features and could almost feel himself understand what it might be to be a woman and to give herself up for such a man. "Careful Samantha," Brock said, breaking the spell Sam was under, "The floor's quite slippery here." Sam smiled in gratification at him and then, and later he couldn't remember why he had done this, he leant up and pressed his lips against Brock's lips, planting a kiss against them and leaving a smudge of red lipstick. "Thanks," he smiled. On leaving the store, having bought both pairs of shoes unable to choose between them, Sam noticed the bulge in Brock's trousers had grown conspicuously more obvious and he farther noticed Brock quickly hurry off into the store room as soon as Sam had paid for his shoes. Sam was flushed with a moment's pride and pleasure at the thought that he, in his feminine form, could be something that guys could jerk themselves off to. And not just any guys either, but someone as hunky as Brock. Sam was further filled with emotions of embarrassment of his own as he discovered Brock wasn't the only one to have been more than a little excited by their flirtation and close contact. All these sexual thoughts had caused Sam to become a little aroused and erect himself and there was a slight bulge in his skirt which, if he didn't stop it, could grow to become obvious enough for him to be discovered. Quickly, he sat down at a table outside a cafe next to Brock's shoe store, hiding his embarrassment beneath the table, and ordered a cold drink which he drank slowly and tried to think about other things to get his mind off the recent encounter. About a half hour later, Sam was ready to move on. He had left the most daunting thing of the day until the last in the hope that the day's experience as a woman would make things easier for him. So it was that the last store that Sam went into in the mall that day was Naomi's, a store that specialised in sexy lingerie of all types and colours as well as other feminine accessories like make-up and jewellery. Fortunately the store was empty when Sam went in, all except for the smiling, busty redhead behind the desk who grinned at him in a friendly way, that was nevertheless nerve inducing for Sam, as he walked in. Sam spent some time wandering around the racks of all kinds of underwear, completely lost as to what he should do or buy. If he thought that choosing all the other clothes had been difficult, then it was all nothing compared to this. After a while he looked up to find the busty sales assistant standing beside him, he flushed red with embarrassment, although what at he didn't know, and was momentarily tongue tied. "Hi, I'm Lucille," she introduced herself in a friendly way that put Sam at ease a little, "Is there anything I could help you with miss?" she asked. Sam forced to control his voice for a moment before coming out with his fluttery, airy, girlie voice, "I'm just looking." "Is there anything particular you were looking for?" Lucille asked, still a little pushy but both friendly and re-assuring, "Is it for you or. . someone else?" she asked. Sam didn't reply immediately, he was admiring a purple lace bra and panty set with matching suspender belt, he itched to try it on, to feel it against his skin but was beginning to clam up under Lucille's attention. She spotted what he was looking at. "That's a good choice, I think that would look great on you," she said, "If you want to try it on then our fitting rooms are just there," she indicated an area at the back of the store where there were a number of cubicles with curtains drawn across them. As a result of this, Sam found himself almost herded towards the fitting room with the sexy purple lace bra and panties. Inside the fitting room, Sam stripped from his skirt and blouse, placing them over a chair in the corner, and the black lingerie from Jemma. His smooth naked body looked really hot in the full length mirror, every inch a petite, sexy woman with large round breasts except for the cock hanging between his legs that was worryingly becoming a little aroused again at the sight of his sexy, naked, womanly body in the mirror. Matters were not helped at all when he encased his false breasts in the purple lace bra which pushed them up and together creating a very sexy cleavage and then stepped into the purple lace panties, sliding them up his smooth, shaved legs and over his pert small ass and his cock. The sensual feel of the lace lingerie against his skin, and his cock in particular, as well as the sight of the sexy blonde in purple lingerie that confronted him from the mirror was making him ever more aroused and erect. Before he knew it, his cock was rock solid, jutting straight out in front of him and creating a huge tent in the skimpy purple panties. Sam panicked, there was nothing he could do, he was trapped in the fitting room, naked except for the skimpy purple lingerie, with Lucille waiting outside, if he came out now his secret would be very obvious but he couldn't get rid of his rock solid erection. "Is everything ok in there, miss?" he heard Lucille's voice from outside the fitting room curtain. Before he could say anything that might stop her, Lucille had poked her head around the curtain to see what the problem was. Sam couldn't hide his secret from her anymore, he just stood before her, in purple lingerie looking like a sexy woman but with a very hard erection. Lucille squeezed around the curtain and came into the fitting room. She smiled at him, it was still the friendly, welcoming, reassuring smile of earlier on. "You know, I thought that you might be one from the way you were so nervy and didn't know what to do, we always can tell," she smiled at him, "This your first time out?" she asked and Sam, feeling himself unable to speak just nodded his agreement, "Don't worry about it, we get plenty in here, we're pretty used to it. What's your name?" SEXretary "Sam," he said in a squeaky, nervous voice. She laughed, but not insultingly, "No, I mean your real name, your woman's name." "Samantha," Sam said, beginning to feel oddly comfortable and reassured despite the situation. "Well Samantha," Lucille continued, "Here at Naomi's we like to make sure all our customers are comfortable and happy and it looks like you've got a problem that's making you just a touch uncomfortable." She indicated his erection which, if anything, was getting stronger by this conversation, "And we wouldn't be the caring people that we are if we didn't offer to help you out with that." With that, totally unexpectedly, Lucille dropped to her knees and pulled the tiny purple panties from his cock and dropped them to round his ankles. Then she proceeded to open up her lips and take the throbbing head of his cock into her waiting mouth. Sam opened his mouth to protest but the situation was so strange that he had nothing to say and instead heard himself let out a decidedly feminine moan of pleasure. Sam had never been given a blowjob before and Lucille certainly seemed to know what she was doing, she sucked and licked his cock and balls while jerking him off in such a way as to make Sam's knees almost buckle beneath him and Sam begin to swoon with pleasure. It didn't take long of Lucille's skilled and expert attentions before Sam felt his balls tighten, his cock twitch and explode and his cum shoot in a stream into Lucille's mouth. Anxious not to get any of Sam's cum on the underwear, Lucille managed to take mouthful after mouthful of his warm sticky juices as Sam's orgasm seemed to continue for ages. Finally, with Sam feeling just a little light- headed at the extreme pleasure of his orgasm, Lucille stood back up again and drew his face towards hers, planting a long, wet kiss on his lips. Using her tongue she pushed the cum that was still in her mouth into his. For a moment Sam resisted, but as his tongue began to savour the taste of the warm, salty, sticky liquid he lapped it up eagerly and was a little disappointed when the kiss was over. Lucille's smile was even wider now. "You really will make a great woman Samantha," she said, "With such a love of the taste of cum. Now get dressed, we've got some shopping to do." Sam spent the remainder of his time at the mall in Naomi's with Lucille's expert advice guiding him in his purchases of a great array of various types and colours of lingerie as well as all sorts of make-up, accessories and jewellery. She even pierced his ears for him, although all he wore now were little studs, in time he would be able to wear all kinds of sexy ear-rings. Sam decided to get a taxi home, with his vast numbers of shopping bags to excessive to take on the bus. Besides, after his heavy day of spending he felt a little extra expense wouldn't do any damage. As he sat back on the back seat of the taxi, surrounded by his bags of clothes, shoes and lingerie, with the driver clearly pleased at the sight of such an attractive woman in his taxi, Sam felt tired but deeply satisfied and happy with his first ever day of girlie shopping and his first ever weekend of trying to live like a woman. I could get used to this, he thought. *** Sam settled into his new job and his new life remarkably easily. The Monday when he had come into start work dressed in some of his new clothing Jemma had smiled a little, almost to herself, but said nothing. Although later that week she generously offered to pay for any expenses that he might experience in equipping himself with a wardrobe for his new job. The job itself consisted of easy secretarial work and Sam found that he was soon able to master every element of it and be of good use to Jemma around the office. In all he was probably more satisfied and happy with this simple, untaxing job than he had been with the one he had before. By April, after a month in the job, Sam felt perfectly at home and comfortable as if being a secretary was just the right job for him, he enjoyed the lack of responsibility and the need to take orders and direction from Jemma. However the biggest development and change came in the enthusiasm in which Sam adopted the life to accompany his new job. That first weekend, Sam had resolved to go to work as a woman but to live at home, apart from the stuck on breasts which he was sure the glue from would run out eventually, as a man to maintain some hold on his masculinity. That first Monday night, Sam had stripped from his feminine clothes and laid out some more masculine ones but couldn't bring himself to put them on. Since that moment he had discarded any thought of living with his old masculine identity and had begun a new life. He now lived night and day as a woman and, indeed, no longer thought of himself as quiet, repressed Sam at all, but as giggly, flirty Samantha. Samantha hadn't been back to the mall again in the month or, indeed, been out in the evenings, but she had dedicated all her time at home to totally perfecting her new feminine persona. The only regret she had was in having to concoct some reason to quarrel with her family, or Sam's family as it really was, and so leave her old life totally behind and make a clean break for it. It was early April when Jemma called Samantha into her office wanting to speak to Samantha on an important matter. Samantha thought back to the day that had started this all off, when Jemma had called Sam into her office for just such a chat. This time Samantha's conscience was perfectly clear but she was equally curious to discover just what it was that her boss wanted of her now. Jemma ushered her into the office and Samantha sat in a chair on one side of the desk, just as she had, as Sam, that fateful day a month before. "You may remember Samantha that when we first discussed your dress code for this job I told you that one of the reasons for it was that our investors demanded it," actually Samantha had forgotten all about Jemma having said that, the reasons for her transformation into Samantha seemed so long ago now, "Well, whether you remember it or not, it's true. This afternoon I have a very important meeting with David Stiller who, as you may or may not know, is this company's principle investor. We need to make a good impression on him if he is to continue his investment here. That's where you come in, Mr. Stiller has a bit of a weakness for attractive blonde women like you Samantha. I need you to flirt with Mr. Stiller and, if he likes you, to agree to have him take you out to dinner. Remember Samantha, the very future of the company could rest on this and they'll be a very big bonus for you if you help out." Samantha didn't really know how she should react to this news. Somewhere at the back of her mind over the past month there must have lingered the thought that there must have been a reason for her new dress code beyond simply not being recognised as Sam, and that at some point she would be called on to do something more than simple secretarial work. Although Samantha had now been living entirely as a woman for the past month, one thing she had not yet explored was any womanly sexuality. She had stayed at home every weekend and evening and, although she still recalled her flirty shoe shopping incident with Brock, the hunky sales assistant, that was a single isolated incident. That was not to say that Samantha hadn't given this sort of thing any thought since then. Her new lifestyle, her sexy clothes and the sight of her sexy body all meant that she was often quite aroused and horny at home and she found herself jerking her dick off far more often now than she had when she was Sam. While she did this, the thoughts going through her mind were no longer just limited to women, every so often images of naked men would pop into her head and she found herself quite turned on by it. Still, despite this, it was a big difference between fantasies and reality and Samantha didn't know how she would react in being called on to flirt with a guy. However she was going to react would be something she would soon find out as Samantha knew that, even if she was totally repulsed by the idea, it was something she had to do. She knew she needed to keep on Jemma's good side and this seemed pretty important to her. At around 2:30 that afternoon, Samantha was sitting at her desk just outside Jemma's office. She had no work to do so she was simply looking at her fingers, admiring the shiny scarlet nail polish she had used that morning. Samantha was dressed in a tight white blouse with short frilly sleeves that clung to the curve of her chest, the top few buttons were undone to give a tantalising glimpse of her false, but convincing breasts. With this she was wearing a very short black velvet mini-skirt which barely covered her ass and thighs and black shear silk stockings with a seam running up the back. Samantha was aware that among some of the women of the office she had a reputation as being a bit of a slut given the sexy, revealing clothes that she wore, but Samantha knew that much of this was just jealousy that they couldn't maintain such a sexy, petite figure as she could. Her blonde wispy hair, although it was a wig this and not the short dark hair underneath was. what Samantha thought of as her hair, was swept back from her face and held in place with some hair clips. Her lips were given an extra touch of sensuality with scarlet lipstick that matched her nail polish and her hazel eyes were caressed by very long false eyelashes that Samantha was particularly proud of. Samantha had just picked up a pen and began idly doodling on a sheet of paper when she heard a closing door and a quiet cough to attract her attention. Samantha looked up to see a man of about forty, he was not very tall or well built like Brock but he did carry himself with a certain authority that someone of Brock's age could never manage. He was dressed in an immaculately tailored and perfectly fitting designer suit and carried a briefcase. His gingery brown hair was cut very short and the flecks of grey to it only gave him a more distinguished look. He flashed Samantha a smile and Samantha coyly sucked on the end of her pen with her scarlet lips and lowered her long eyelashes. "Hi, I'm David Stiller," he introduced himself; "I've got a meeting with Jemma, but I think I'd much rather spend the afternoon here with you." Samantha flushed red at this compliment in an unintentional way, but in a way that brought an attractive colour to her cheekbones. Samantha fluttered her eyelashes and said, in her giggly and fluttery voice: "It's nice to meet you Mr. Stiller, I'm Samantha." "Please Samantha, call me David," he said, leaning in closer to her in a way that made her flush with excitement. To hide her excitement and embarrassment, Samantha quickly got up from her chair and went over to open the door to Jemma's office in order to usher David in. On her way over to the door, however, Samantha made sure to give David a good look at her swaying ass in the very short velvet skirt. She still wasn't entirely sure whether she was doing this because Jemma had told her to flirt with David or because she herself wanted David to admire her feminine body. "You can go in now, Mr. Stiller," she said to him, holding the door to Jemma's office open for him. As David Stiller went over into Jemma's office he had to walk close to Samantha as she held the door open for him. For a moment her large, protruding breasts brushed against him and, as he walked passed, he brushed one hand over the curve of her ass. As he did this their eyes met for just a second and he smiled at her. She blushed once again and quickly closed the door behind him, returning to her own desk and her own thoughts. After a couple of minutes, Samantha realised that she was still smiling, although she thought David's advances to be a little forward she couldn't deny she had enjoyed them and certainly had he stayed much longer he might have been surprised to notice a strange bulge outlined in her short skirt. Samantha lost herself in thought about all of this for quite some time, she didn't know how long, until her reveries were interrupted by the sound of Jemma's voice. Jemma had opened the door of the office and was looking over at her. "Samantha," she said for a second time, "Stop staring into space and bring us some coffee." Samantha hurried to the office kitchen to make some coffee, she was nervy and agitated and so it all ended up taking a lot longer than it would normally do. Still, about ten minutes later Samantha, carrying a tray with a pot of coffee, milk, sugar and two coffee cups, pushed open the door to Jemma's office and came in. Jemma wasn't sat behind her desk, she wasn't in the office at all having gone to retrieve some files. There was just Samantha and David, who was sat back in a chair on the near side of the desk. David-looked round and smiled at her as Samantha came in with the coffee and walked over to put it down on the desk. Again, she deliberately added an extra sway to her hips as she walked across the room on her six-inch heeled sandals and, when she had to set the coffee tray down on the desk, she deliberately and slowly bent over to do so, so that her ass stuck out right at David who could now see the curve of her smooth legs and the seam of her sheer stockings and her enticing little ass in its tiny black velvet skirt. She turned and flashed him a brief, flirty little smile as she walked back passed him to leave the room. Quickly, so quickly that Samantha didn't really realise what was happening, David reached across to her slender waist as she walked passed him and, with a slight pull, caused her to lose her balance and fall, tumbling, into his lap. Samantha lay sideways across David's lap, with her stockinged legs dangling over one arm of the chair and David's arm supporting her back and head on the other arm of the chair. The hand of this arm was stretched round her back so it was cupping one of her breasts, while his other hand rested, for the moment, across her waist, stopping her from getting up, but, as David talked to her, this hand strayed down to her thigh were some bare, exposed, smooth skin had been revealed between her stocking tops and where her skirt had rid up her thigh a little bit. Samantha's own hands rested on her lap, keen to cover up any tell-tale signs that all was not as it should be beneath her skirt. Samantha had tried to convince herself that, underneath all the clothes and make-up, she was still Sam, a man, and that she couldn't and shouldn't be having feelings for another man. But another part of her was saying that she had left that old life behind and David's closeness was certainly causing Samantha's heart to flutter and Samantha to tremble with excitement. "I have to say Samantha," David was saying to her, "That of all of the gorgeous secretaries that have worked in this office, you are the most beautiful I have ever seen." Samantha giggled in a girlie way at this compliment, she was certainly very pleased at the effect she continued to be able to have on people. For a moment, her mind was on this and she didn't notice how David's hand was beginning to stray up her bare thigh and under her skirt. His flirting and his touch, the feel of his hand on her bare thigh, crawling towards her sexy purple panties had all contributed to Samantha feeling ever more aroused and her cock becoming ever harder and more erect beneath her skirt. These feelings were combined with Samantha's increasing nervous worries as she felt how David could easily discover her secret and not only would she be horribly embarrassed but it could also jeopardise the future of both the company and her job. Fortunately, just at that moment Jemma came back into the room carrying the files she had gone to fetch and David withdrew his hand from inside Samantha's skirt. "Samantha and me were just getting better acquainted," David smiled at Jemma, "She's quite a girl." Through the material of David's suit and her own skirt, Samantha could feel, pressed against her ass, the feel of David's hard erection. As she got up and hurried from the room, Samantha made sure to hold her hands in such a way that David couldn't see from the bulge in her skirt the similarity of their arousal. After David left about half an hour later, with just a brief smile and wink at Samantha where she sat at her desk with her erection finally lost, Jemma called Samantha back into her office. Jemma smiled at her, the meeting had gone well. "Well done Samantha," she said, "You obviously made a pretty good impression on David. He wants to have dinner with you on Friday night," Samantha knew that Jemma noticed here the wide grin on h» face but Jemma didn't pause, "Remember, we need his investment so make sure you continue to make a good impression and do whatever David wants of you." *** On that Friday night, Samantha turned up at eight o'clock at the very glamorous and very exclusive restaurant at one of the most expensive hotels in San Diego where David was staying during his visit. Tonight she had made an extra special effort with her appearance and it had really paid off. If, normally, Samantha was able to convince as an ordinary, good looking girl, tonight she was absolutely stunning, she turned a lot of heads as the Maitre d' ushered her to the table David had booked for the evening where he was sat waiting. In thanks for Samantha's effort with David, Jemma had been particularly generous with Samantha and had bought her a very expensive, gorgeous designer dress that Samantha was now wearing. It was an aquamarine colour with a halter-neck and a plunging neckline that barely contained Samantha's breasts and a frilly skirt that just brushed her knees. The length of her legs were extended by wearing her six-inch heeled strappy black sandals and her legs themselves were encased in black silk stockings that were attached to a dark blue suspender belt while she wore matching dark blue silk panties under her skirt. Her nails had been professionally manicured and extra long blue-green false nails had been attached to all her fingers to give them an extra slender femininity. Jemma had also bought her a new wig, this one was still an ash blonde colour but it was longer and more extravagantly styled into curls and then tied up with two individual dangling wisps of hair hanging over her soft, feminine cheekbones. She wore her longest false eyelashes and had painted her eyes with a soft, glittery blue-green eye shadow and her lips with a glittery pink lipgloss. The final touches to her outfit were added with Jemma's final present. Jemma had given her a parcel on sending her home early from work that afternoon to get ready. When Samantha had opened it she had found the most gorgeous matching diamond bracelet and choker which now clasped around her neck, enhancing its elegance, and some extravagant diamond ear-rings which dangled down from her ears to tier shoulders, exposed for everyone to see with her hair tied up as it was. The restaurant and the hotel were certainly used to beautiful and glamorous people but even they turned and stared at the image of sexy glamour that Samantha presented tonight. David, sat waiting for her in an elegant dark blue suit, also gasped in amazement at how great she looked. "I don't know how you managed it Samantha," he said, pulling out her chair for her to sit down in, "But you actually look even more gorgeous today than usual." The dinner itself was perfect in almost every way. The food was of an extravagant luxury and taste that Samantha could only have dreamed about before, the dark, sensual red wine slipped down with ease and the candle-lit elegance of the restaurant was one of the most romantic places Samantha had ever been. She could really see herself living like this, she thought as she leaned in towards the table to catch what David was saying. David himself was absolutely perfect company to match the perfect meal. He was charming and witty in a way that made Samantha constantly giggle or even laugh out loud and he was considerate to her every need and desire. As the evening went on Samantha could feel her oppositions to the idea of being with a man begin to ebb away as David's company made her feel so relaxed and happy. When, after paying for the meal, David took Samantha by the hand and offered to take her up to his room, Samantha offered little objection.