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.