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?"