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Chapter One -- Gamer in a Suit "You look like a gamer in a suit," Paddy McClintock said to Taylor Averille. "Even your name isn't right. What the fuck is Taylor? It isn't one thing or the other," Paddy sat behind his huge oak desk, one leg resting on the other. He took a long sip of his coffee and looked up at Taylor. "You still here?" he sniffed. "So I take it that's a no to PostPay?" Taylor replied smugly. "And that attitude isn't helping you kid. The code looks fine but you need to get a haircut, lose the earrings, drop the attitude and get a partner who knows something about business." "Don't let the door hit you in the ass on the way out," Paddy said dismissively and picked up his Wall Street Journal. Taylor shut the door behind him and carried his backpack through the maze of desks in the open-plan office making his way to the elevators. He noticed that a disproportionate amount of staff working at Paddy's investment company were women. They weren't all young but most of them were; they were all stylishly dressed: power suits, killer heels, nylons, red lipstick, coiffed hair. Young, old, fat, thin, tall, short, they all had class; they looked like they belonged right here in the offices of McClintock Developments. The men too, although most were down to their shirtsleeves, wore Brooks Brothers, Brioni, or Giorgio Armani, natty ties and crisply ironed shirts. The women leaned over desks chatting and flirting, skirts dangerously high on the thigh. Men stood in groups looking seriously concerned about something. It didn't look like anyone was working but Taylor knew better. The best analytical minds in Chicago worked for Paddy McClintock. Taylor walked down Van Buren Street ripping off his tie. He dumped it in a trash can and crossed South Columbus Drive and entered Grant Park near Buckingham Fountain and turned left towards the gardens. He found an unoccupied bench away from the crowds and sat down feeling dejected. Paddy McClintock had been the fifth investor in a row who had turned him down. At twenty-five, with boyish good looks, shoulder length blonde hair and a slim build he did look like a gamer in a suit or possibly even a skater-boy in a suit. It didn't matter; he couldn't get anyone to take him seriously. He had the goods. His codes were clean slick and bug-free but it was hard trying to get somebody to believe in him, to invest in his startup, to take him seriously. He bet those skinny-ass bitches at McClintock's got taken seriously. For some reason an attractive woman in a power-suit and heels carried more credence than a young man in a cheap suit from Suitsupply. Taylor sat hunched over, staring at the ground, dragging his already scuffed brogues through the gravel like a petulant child. The sun reflected off a chink of metal buried in the sand. He wouldn't have taken any notice but the toe of his shoe swung back through the gravel and partially exposed the object. Taylor recognised it immediately. It was a USB flash drive. Taylor poked at it with his shoe and it broke free of the pebbles. It looked intriguing. He'd seen plenty of novelty USB drives before; in his line of work they were like nails are to a carpenter. He'd seen racing cars, guitars, aliens, teddy bears, hotdogs; one guy even had a penis- shaped USB drive. He leaned down and freed the drive from the sand and rubbed it on the fabric of his pants. It was matte black and metallic and appeared to be set with some kind of red stones around the edge that glowed dully. When he picked it up he would have sworn that the red stones flashed brightly for a second and that it vibrated in his hand sending a little shock through his fingers. He nearly dropped it but he held onto it, in fact it seemed almost glued to his fingers. He examined the USB drive, turning it over in his fingers. It looked expensive, not the cheap, plastic-cased utilitarian jobs you often found discarded in the street. It was likely someone had lost it. As a software coder and programmer Taylor knew the dumbest thing anyone could do was to connect a drive to your device when you had no idea where it came from. It was like playing Russian roulette. It could contain a virus, a hack, a Trojan or malware. It most likely contained porn but it looked too elegant, too opulent, to contain something so prosaic. Taylor knew that he should drop the USB back on the ground or toss it in the nearest bin but he slipped it into his pocket. He picked up his backpack and made his way to Union Station. It was a one mile walk but the walk allowed him to clear his head and he began to write code in his subconscious. By the time he arrived at his one bedroom walk-up he had forgotten all about the USB drive. But it remained in his suit jacket pocket; the little red stones were glowing, pulsing, vacillating. After a microwave dinner Taylor took a shower and changed into jeans and a T-shirt and sat sans shoes and socks in front of his favourite computer and worked on some of the code he had conjured up during the journey home. "It's shit!" He slammed his hands down on the keyboard and then deleted what he had written. He got up to get a beer and noticed that it had gotten dark while he was working, the only light in the room came from the screen of his PC and the twinkling LEDs from the CPUs of his other workstations. On the way back from the refrigerator he thought he noticed a faint glow coming from his coat. He went over to where it was hanging on the back of the door and put his hand in the pocket. His fingers curled around the USB drive. He knew that he was imagining it but the drive seemed to vibrate in his hand. Taylor pulled the drive out of the pocket and was surprised to find that the little red stones were in fact flashing sequentially, almost like a beacon. He found that quite incredible because the USB drive had no power source; none that he could he see anyway. Maybe it had a tiny NiCad battery inside it or something, but that made no sense. Ignoring the warnings that were screaming at him in his mind he took the USB drive over to his least vulnerable personal computer, a standalone Sony Vaio laptop that was at least seven years old. He double checked that the Vaio was not connected to his network by fibre, Wi-Fi or Bluetooth and it wasn't. Taylor scrutinised the USB device once again; it looked almost otherworldly, mystical, magical, like a miniature version of the black monolith from 2001 A Space Odyssey. He felt it vibrate in his hand and emit a minute electric charge. The red stones were now flashing erratically, almost like the device was excited to be near the PC. The computer finally booted up and the Windows logo appeared and Taylor logged on. He looked at the USB drive again anxiously; something deep inside was telling him not to do it but he ignored the warning and slammed the drive into the USB port. Taylor half-expected the PC to halt and catch fire or for some radical virus to execute a program that took control of the laptop or lock him out but at first nothing happened. Then a string of code appeared on the screen but the code was using symbols that Taylor had never seen in his life. They looked almost alien. Then the screen filled with what looked like text but it was illegible, just a series of random symbols and cyphers. The red lights on the USB began to pulse rhythmically. The unintelligible symbols became glyphs and then what Taylor was almost certain were hieroglyphs and then the text seemed to cycle rapidly through a series of archaic languages: Hebrew, Latin, Etruscan, and numerous dialects that he didn't understand, until finally the text became English. Taylor was amazed. Not only with the rapidity of the changes from unintelligible unknown symbols, to ancient languages, glyphs and calligraphy but with the appearance of the symbols and ancient languages themselves, because it was simply not possible for the computer to generate them. Put simply, the programming language embedded in the Sony Vaio CPU did not support them. The screen became stable and it appeared that the program had finally settled on the English language as its means of presenting an interface, the red stones glowed a steady dull ruby-red. Taylor stared at the screen and presumed that whatever software was installed on the USB drive was some kind of elaborate hoax, most likely a spear phishing scam. Whoever had thought up the ruse had gone to extraordinary lengths to build the USB and load the sophisticated program onto it. He was glad that he had plugged the USB into his old standalone laptop; the program looked like it would cause chaos if it was released onto a network. Confident that the program was confined to the old Vaio and could not access his other computers, Taylor thought it might be fun to play along. He read the instructions on the screen. Congratulations. You have been granted the most extraordinary and invaluable privilege. You have been selected to undertake a life changing manifestation that will grant happiness and fortune depending on how you use the gift being offered to you. This is an unprecedented and unique experience but there are precedents and protocols that you must agree to before we proceed. Do you agree to participate? Y/N' Taylor hit the 'Y' key on the keyboard. The screen refreshed itself. We understand that at times you might become confused or have concerns so to that end we have provided you with a Help function. It is visible to you at the bottom right of your screen. Taylor saw the little Help icon at the bottom of the screen and he nodded. Good. You can see it. Feel free to use the function whenever you are unsure. Taylor was taken aback. Could the hoaxers see him? Did they see him nod? Were they accessing the camera on his laptop? The indicator light wasn't glowing to indicate the camera was switched on. Never mind let's see where the hoaxers were going with this. It looked like it might be fun. You have a burning desire to be successful, to fulfil your dreams and wishes and we have a power unimaginable to you that can ensure you achieve these goals. It just won't be in a way that you expect. It will be challenging and difficult at first but if you use the special gift we are about to bestow upon you wisely you will succeed. Even if you are not astute enough to use the gift to fulfil your dreams and desires, you will have taken a unique and daring challenge that we are sure you will enjoy. Do you wish to proceed? Y/N Taylor pressed Y. "This is going to be fun," he said to himself in darkened room. Yes Taylor, this will be fun; but not in the way you are thinking. Taylor was shocked. He was sure that the microphone function on this laptop no longer worked. The scam was very elaborate indeed. He was waiting for the program to direct him to connect to his home network or ask for his bank account details and when it did he would shut it down and wipe the computer clean and restore the factory settings or he might even just ditch it. It was old and outdated anyway. These are the terms and conditions that apply to the gift which is to be bestowed upon you: The gift cannot be returned for ninety revolutions You will not be able to tell anyone else about your gift, as much as you would like to You may use the gift in any way you choose but be warned: you will be held responsible for your actions If you elect not to return the gift after ninety revolutions, the gift will be bestowed on you permanently and can never be returned Do you agree? Y/N "What the fuck?" Taylor stared at the screen. The little Help icon on the bottom of screen suddenly activated itself and a textbox appeared on the screen. Do you have a question Taylor? A concern? Doubts? Why had the Help function activated itself? Never mind. 'Who is bestowing this gift on me,' Taylor typed, feeling a little cynical. The cursor just blinked. There was no answer. 'Why me?' he typed. The... I'm not sure what your kind call it... the rune, the oracle, the device... sensed that you are worthy 'Where did it come from?' he typed and tapped his fingers waiting for a response. Nothing... just the blinking cursor. Obviously the Help function had a selective response feature. It wouldn't answer questions that it did not understand or was prevented from answering by the programmer. 'What will my gift be? The oracle or whatever it is should be able to answer that' he typed. It won't be what you expect but it will be wonderful and astounding. You might be disappointed at first but if you use the gift wisely it will not only bring you good fortune it will bring you great pleasure The Help function was 'all assistance short of actual help' Taylor thought. "Fuck it," Taylor whispered. He closed the Help function and pressed Y. Your journey begins now. Enjoy your gift. Please remember the terms and conditions that apply. The screen on the laptop suddenly went blank and it appeared that the computer had shut down. "I knew it. It was just a scam," Taylor went to rip the USB out of the laptop but when he touched it, it gave him a shock. This was not a little tingle, it was full on zap. Then the ruby lights on the USB drive which had become dull suddenly illuminated to full brilliance; they were so bright they were hard to look at. The fan on the Sony Vaio began to whirl so fast that it sounded like it might disintegrate. The computer actually began to shake. A tiny pinprick of white light appeared in the centre of the screen, pulsing rhythmically and morphing into a series of ever-changing shapes. Taylor leaned forward, his nose almost touching the screen trying to discern the patterns when suddenly the screen exploded into a kaleidoscope of brilliant colours that almost blinded him. Some of the colours were indescribable, he had never seen them before, it was like he was having an out of body experience. A loud thrumming noise filled his head and seemed to get louder as the colours on the screen got brighter and changed faster. He felt like he was undergoing sensory overload and then he blacked out. ***** Taylor knew there was something wrong as soon as he awoke. He was sprawled in front of the laptop with his head on his hands and he woke up feeling like he had been asleep for days but was not rested. The events of the previous night played out across his conscious, but that wasn't the only concern he had. He just didn't feel right. His body felt different somehow. He remembered coming out the anaesthetic after having his appendectomy and he felt very much the same way; like someone had invaded and altered his body. He didn't hurt; he just felt peculiar, like he didn't belong in his own skin. His jeans were too tight around his ass but too loose around his waist and his t-shirt was too tight around his chest. Something was going on between his legs, he hadn't awoken with his usual morning glory, or nocturnal penile tumescence as it was correctly referred. In fact nothing seemed normal down there at all. It didn't seem wrong; it just seemed different. He also sensed things differently; like he'd had some sort of epiphany that had given him clarity of thought from a new perspective. Taylor needed desperately to pee and upon entering the bathroom it became clear why he felt so different. It was because he was not a he; he was a she. Taylor was stunned. It was Taylor's face staring back but it was subtly different. The cheeks were more prominent and were fuller and the chin was a little more pointed and the nose not as prominent. It was still Taylor but a feminine version of Taylor, the neck appeared more slender, likely because the thyroid cartilage seemed to have disappeared. But the most significant change Taylor could see was the set of pert breasts that swelled the front of her t-shirt. The nipples were prominent through the cotton fabric. Taylor ripped off the t-shirt and sure enough a pair of perky breasts, proportionate to her body size adorned her chest. Her stomach was flatter, the waist was small and the hips a little wider and the jeans would have fallen off Taylor's significantly slender frame if not for the plump but firm buttocks holding them up. Taylor was dreaming but still busting for a piss and struggled out of the jeans and underpants. Taylor was amazed to see a curved pubis covered in a sparse patch of pubic hair which warranted further examination, but first, if Taylor didn't piss right now an embarrassing accident was unavoidable. Sitting on the toilet came naturally; but of course it would as there was no penis to point at the porcelain. Finishing her business Taylor dabbed at that place with TP and flushed. This was just bizarre. Taylor was evidently dreaming; likely brought on by that stupid USB program that she had stupidly loaded up on the old Vaio. Taylor went to the bedroom and stripped and stood before the mirror. Sure enough it was Taylor's face... but then again it wasn't. It was feminised and the long blonde hair framing the face only made it more effeminate. It was Taylor's body, the freckles and moles were in the same place, the silvery scar on the calf from the childhood skiing accident, the appendix scar on the lower right side of the abdomen. But the body was more slender, the hips wider, the waist smaller, the skin softer. Turning side on the belly wasn't quite flat, it swelled a little but in a sensual way, the breasts were small, perfectly shaped and proportional to the frame, with pink berry-like nipples. Turning front on again Taylor's eyes were drawn to the pubis, the curve of the flesh beneath the belly leading to the valley between the legs. It was covered in a downy layer of soft hair. Taylor felt the heft of the breasts, softly tweaking the nipples until they engorged and then ran her fingers down the curve of her waist, across the little swelling of the belly and finally into the mesh of fine hair between the legs. The nipples radiated soft ripples of delight, but when her finger touched what lay between the folds of the vulva it radiated a fiery, sensual, almost lecherous ring of pleasure that Taylor found hard to describe. Of course it was a dream. Boys often fantasised about having a female body. He remembered in his teens sitting in the bleachers with his friends watching the cheerleaders practice. He secretly envied the girls their curvy forms, their long legs sheathed in shimmering pantyhose, buttocks clad in tight panties, little skirts flicking around firm thighs, heaving breasts and tousled hair. Pretty faces with blue eyes accentuated by dark eyeliner and mascara, rouged cheeks and plump pouty lipsticked lips. He was sexually aroused, as were the other boys. The boys described in great detail what they would do to those girls if they ever got hold of one, as unlikely as that would ever be. Then one of the boys asked the question that the others were thinking but were too afraid to extrapolate. "What would you do if you were a girl?" Of course they had joked and quibbled about how they would never come out of the bedroom. How they would be the biggest slut ever, enjoying the woman's body to the fullest in an orgy of debauchery. Thinking like a man thinks; unable to think like a woman. "Is that gay?" someone had asked. "Only if she takes up the ass," some bon vivant carped, and the subject matter changed and they moved on. But at some stage, all men and boys have pondered that exact question: What would you do if you were a girl? And now Taylor was. Before the USB Taylor thought of himself as him or he. Since the transformation Taylor had been unable to think in gender terms referring to Taylor only as I, it or they. Now Taylor thought of herself as she or her. As a girl. As a Woman. It was too much; she wanted to wake up from this dream. This wasn't the gift that the USB had promised. Where was the happiness and fortune to be had by changing gender? But the oracle had prophesised that the gift wouldn't be what Taylor expected but it would be wonderful and astounding. That Taylor might at first be disappointed but if the gift was used wisely it would not only bring good fortune, it would bring great pleasure. Well Taylor was disappointed and she wanted to give the gift back and become Taylor again, Taylor the man not Taylor the woman. She suddenly felt very weary and decided that sleep would help. Sleep was the solution. She would wake up from this dream and all would be as it was before she had slammed that USB drive into the old laptop. She fell on the bed and pulled the covers over her new body. It felt weird having the weight of her untethered breasts yank at her torso and to not have to adjust a penis and scrotum into a comfortable position. It didn't matter; when she awoke all would be normal. When Taylor awoke all was normal. It was as normal as it was going to be for ninety revolutions, which she presumed referred to the earth rotating on its axis. It was normal as it was going to be living life as a woman for ninety days. Taylor was still a female. She recalled the time that she sat in the bleachers with her friends hypothesising what they would do if they were suddenly to become a woman; the crudity and vulgarity of what they had said they would do. Something had changed, she wasn't thinking like that anymore. But she was still curious. Taylor went to the bathroom and rummaged in her travelling toiletry bag and found the shaving mirror and brought it back to the bed. She lay down on the bed and put a pillow under the small of her back and opened her legs. She held the shaving mirror between her thighs and explored the intimate parts of her new body. She explored her vulva and outer labia nestled in the thatch of pubic hair. She opened her labia to expose her labia minora, the coral pink inner lips and her clitoral hood. She parted her labia minora and inserted a finger into her vagina but it was occluded and painful so she withdrew it. She manipulated her clitoral hood and a rather pleasant sensation radiated from it. If asked she would compare it to the feelings she had when her fraenulum was manipulated when she had a penis. Taylor opened her clitoral hood and stroked her clitoris directly. She gasped. The little bud was very sensitive; almost too sensitive. She withdrew her finger and then delicately circled it with the pad of her fingertip. That felt nice. Very nice. Her vagina began to lubricate and she gathered a few dewy droplets with her fingertip and softly rubbed the secretions on her clitoris. Her breathing became laboured as the sensations slowly intensified. Taylor imagined she could lie there for hours just gently stroking herself, allowing the delicious responses and excitement to slowly radiate through her pleasure centres. But there was also a deep longing to bring on her climax, she wanted to experience her first female orgasm and she rubbed herself harder and faster. The feeling was hard to describe. It was like lying on the beach and feeling the tide coming in, the warm foam lapping at her toes, then the silken wavelets crept up her legs and then the wave became a flame that began to glow, redder and redder and then melted into white light. Taylor cried out as she lay on the bed writhing, her hand pressed between her legs, the white light became a kaleidoscope of colourful butterflies flying in waves over her body and then morphed into the crescendo of an earth-shattering tsunami of gratification and contentment. It was incredibly wonderful; simultaneously delicate and sublimely intense. Taylor lay panting on the bed as the film of perspiration on her body cooled and the tide of pleasure receded. She sprang to her feet. It was time to stop vacillating and complaining and to start living with her new body, after all it was going to be hers for ninety days. It was time to take it out for a test drive so to speak. Taylor inspected herself once again in the full-length mirror but this time she was critical. The transformation had morphed her anatomy from male to female but had done nothing else. There was still some landscaping to do. She went into the bathroom and ran the hot water tap and filled the sink. She lathered her legs, replaced the blades in her Gillette Fusion razor and carefully shaved them. She looked critically at the thatch of pubic hair and decided that it too needed to go. She very carefully and gently lathered and removed the offending foliage and was very pleased with the result. Finally she shaved her underarms and checked the results in the mirror. There was nothing she could do about her lank blonde hair for now and her eyebrows needed shaping but she would leave that to the experts. She took a long hot shower, luxuriating in the feel of the hot water on her freshly shaved legs and pubis. She washed and conditioned her hair and towelled herself dry. She looked at her face critically in the mirror. She wasn't beautiful but she wasn't unattractive. Undoubtedly the application of makeup and a good hairstyle would help. Now... what to wear? Taylor's jeans no longer fit her and if she wore them she would look like a hobo. She remembered that Taylor had a pair of black compression tights that he wore when working out during the winter months and she dug them out. It was funny how she thought about her male alter ego as another person entirely. She found an oversize t-shirt that looked good on her and was pleased to find that Taylor's Nike sneakers still fit. His underpants were useless to her so she shimmied into the tights sans underwear, pulled on the t- shirt, found some clean socks and put on the Nikes. She didn't look too bad with her hair pulled back in a ponytail. Taylor checked her wallet. She had ninety dollars in cash. She gave a small prayer to the oracle, or whoever was now the master of her destiny, that her name was gender neutral because the name Taylor Averille was on her credit cards, driver's licence and everything else of importance. She got close to the mirror and held her driver's licence up next to her face. The face in the photograph was close enough to her own for her to pass any rudimentary inspection. Driver's licence photos were never meant to be glamour portraits anyway. Everything else was the same except her weight and sex but whoever bothered to look at those? Taylor threw on a denim jacket, grabbed her keys and jammed her wallet into her backpack and went outside. She faced the world with both trepidation and excitement. There was nothing for her to worry about; it wasn't like she was a man going out dressed as a woman and her voice had changed because of her altered physical characteristics. She quite liked the sultry sound of it. Taylor had to admit that she was quite excited to be going shopping. "Let's take this puppy for a spin," she giggled to herself. She supposed that she looked quite plain and dowdy being sans makeup and being dressed down, but that was fine. She didn't want to draw attention to herself, at least not until she had made some significant changes to her appearance and her wardrobe. The issue for Taylor was that she was a twenty-five year old woman who knew nothing about being a female. Taylor, the male Taylor that is, had a very specific type of woman that attracted him and now that he was one, so to speak, that's how she wanted to present herself. She just didn't know how to do it. She knew that people would assume that she knew how to do these things; it would have been part of her growing up. Taylor realised that she should have done some online research before she left home but she was not to be thwarted. She sat in the Passion House Coffee Roasters and sipped a latte and went to work on her tablet. Her friend Google advised her that just one block over on Sawyer Avenue was Penny Lane Studios where it was claimed; a complete makeover could be achieved in two hours. She was lucky. There had been a cancellation and she took the vacated appointment for that afternoon. This would give her a few hours to shop. Male Taylor never thought of shopping as something to be enjoyed, it was a necessity but something had changed. She was excited. She smiled to herself and wondered if her credit cards were going to vibrate like the alien USB when they realised the pasting they were about to take. A ten minute Uber ride got Taylor to the Walmart Supercentre on Wellington Avenue. It would do for a start, Taylor needed a basic wardrobe; she would worry about getting designer labels later. She went straight to the ladies clothing section and browsed the racks knowing that browsing would attract a sales assistant. She dismissed the pretty little thing who looked at Taylor like she had dogshit on her shoe and a few minutes later a warm, matronly woman saleslady approached her to see if she needed assistance. Taylor had had enough time to concoct a story: She had recently come home to find that her boyfriend had thrown her out and her malicious so called best friend had moved in. Her clothes had been thrown in the street and had been picked over before she arrived at the flat to find herself homeless. She had money and had found somewhere to live but she literally had no wardrobe whatsoever. Lilith, the saleslady was only too willing to help, especially when she found out that Taylor intended to buy a complete wardrobe and other necessary accessories from the store. "Let's start with underwear shall we?" Lilith smiled. "Yes; let's." Taylor gave her what she hoped was her best smile. "I see that you are not wearing a brassiere," Lilith said reproachfully. "I know; that bitch tore up all my underwear," Taylor lamented. They were now in the lingerie department and Taylor was excited. Not titillated like a man would be, imagining women wearing sexy lingerie, but excited at the prospect of wearing pretty undergarments. "Bra size?" Lilith asked. 'Ah, the first stumbling block,' Taylor thought. Then she saw the sign: 'Our trained professionals will assist you to find your correct bra size. Please ask for our complementary bra fitting service' "You know, my old bras didn't fit me that well. Why don't we get a complete new sizing?" Taylor smiled and Lilith approved. Lilith took Taylor into one of the fitting rooms and had her remove her jacket. "This will work better if you take off your t-shirt too but I understand if you're shy," Lilith said but halfway through the sentence Taylor had her t-shirt pulled over her head. Lilith took a tape measure and measured around Taylor's torso under her breasts and had Taylor breathe out and took a measurement then she did the same around the fullest part of her bust, then she consulted a sizing chart. "Wait here," Lilith said quite curtly but Taylor appreciated Lilith's assistance. She came back in a few minutes with three plain bras. "I had you pegged as a 34B as soon as I saw you but we'll try these on and she what fits best. Don't worry about style, just the fit, once we have you sized you, you can choose whatever you like from our selection," Lilith said. She helped Taylor try on two of the bras and Taylor took particular notice of how Lilith adjusted bra straps. The second bra, a 34B, fitted perfectly and Taylor immediately felt relief once her breasts were supported. She put on her t-shirt and was pleased with the effect. "While we're here with the tape we might as well do your hips and waist." Lilith put the tape around her hips and waist. Because she was wearing leggings there was no need for her to take off any clothing. "Size six, but you knew that I suppose, unless you've put on or lost any weight," Lilith said. "I did lose some weight very recently as a matter of fact," Taylor said cheekily. "Well I must say I like your figure. I'm not a fan of these little stick-insect fashion models getting around on the TV and social media," Lilith sniffed. "Thank you," Taylor blushed. "You need to fix your hair and makeup though," Lilith brought Taylor back to earth with a crash. "Come see me when you've finished choosing your underwear and we'll look for some clothes," Lilith left Taylor to browse through the lingerie section on her own. Taylor liked the panties, especially the spandex-blend fabric. She toyed with different types: hipster, bootleg and bikini and then she selected half a dozen matching bra and panty sets of various colours; good fitting but unembellished. Then she treated herself to some nice fancy bras and panties. She made herself stop when it dawned on her that she would only need enough underwear for ninety days. She returned half the underwear back to the racks. Next she moved onto the hosiery section and using the sizing chart she selected half a dozen pairs of pantyhose and holdup stockings mainly flesh-toned but a couple of pairs of black nylons too. Her male alter ego did not understand why modern women eschewed hosiery, Taylor admired a well turned leg sheathed in delicate nylon. He thought a woman wearing a suit or dressed to the nines who presented bare-legged to be underdressed; like a man wearing a suit without a tie. Female Taylor was of the same opinion and could hardly wait to try them on but it would wait until later. She went back to the fitting room and put on a pair of panties and a bra, keeping the price tags so she could pay for them. She located Lilith who was waiting patiently for her with a shopping trolley and Taylor put the underwear and hosiery in the trolley. She and Lilith went on a small shopping spree with Taylor having to remind herself constantly that she only needed three months' worth of clothing and not to be too extravagant. "Shoes?" Lilith raised her brows questioningly, looking reproachfully at Taylor's sneakers. Taylor had to suppress an almost uncontrollable urge to buy a disproportionate amount of shoes for her needs. She always thought it was a myth about women wanting more shoes than they needed. She settled on two pairs of high heels: one pair of plain black pumps to go with the business suit she had selected and a pair of red ankle-strap stilettos. A pair of cute but practical flats was thrown in the trolley, along with a pair suede ankle-boots and she was done. She asked Lilith to scan the items that she indented to wear from the store and went back to the fitting room and emerged fifteen minutes later wearing a pair of high-waisted blue skinny-jeans, a white longline tank t-shirt with an ivory waterfall cardigan over, tan suede ankle- boots and a textured blue silk scarf. Taylor's ears were pierced and had remained so after the transition so she was able to wear a pair of simple silver drop earrings, accompanied with a matching necklace and bracelets she had picked up in the accessories section. She also added a large makeup case to her purchases, along with some perfume and deodorant. She had used the perfume and deodorant on herself but the makeup remained a mystery. "Well, that's an improvement." Lilith clapped her hands together lightly, applauding her acumen in transforming Taylor from a dowdy frump to a woman with class. Lilith's advice had been invaluable when Taylor was trying to mix, match and accessorise her outfits. When Lilith scanned her credit card Taylor couldn't help but think that had she come in here yesterday as a male she would have spent a fraction of the money and left with half as many clothes but would still be adequately kitted out for three months. Girls had it so much harder! Except for having a plain face and unkempt hair, Taylor looked quite presentable. Taylor loaded her purchases into the trunk of an Uber and rode it to Penny Lane Studios. She created a stir when she arrived at the salon and began to unload her accoutrements; one of the stylists came out of the Studio to assist her, for which she was grateful. The young woman who assisted her was also to be her stylist and was named Gail. It was obvious that Gail was not impressed with Taylor's lank blonde locks and pale bare-skinned face but was too polite to comment. Once again Taylor had fabricated a story. "I just came back from working as a volunteer in Tuvalu, helping to set up the island's technical infrastructure," she said. "I returned with only the clothes on my back and haven't seen a hairdresser or beauty therapist for over a year. I promised myself a new wardrobe and a full makeover when I returned home." Taylor smiled. "Let's tackle your hair first. Any particular style or colouring you want? How much do you want trimmed?" Gail asked, running her fingers through Taylor's tangled thatch. "Just have at it Gail. You do whatever you think will suit me. Something sassy but still professional looking," Taylor said. After nearly two hours of shampooing, blow-drying, colouring, cutting and styling, Taylor's dirty blonde mane had been transformed into a contemporary style: platinum blonde shoulder-length waves of soft flaxen curls with white highlights. She and Gail were both delighted. "Ok honey I have to attack those eyebrows now that I've finished with your hair. They look like Angelina Jolie on a bad day," Gail scoffed. Fifteen minutes of waxing, tweezing and shaping left Taylor with nicely shaped soft angled arches which Gail defined with an eyebrow pencil. "I think you look lovely Taylor and you have beautiful skin. I'm going to pass you over to Miriam to finish your makeover." Gail led Taylor out of the hair salon and over to the makeup station. "Hi, I'm Miriam, what can I do for you?" the pretty little makeup artist asked. "I'll say the same thing I said to Gail. I haven't worn makeup for over year; I've nearly forgotten how, so just do what you think is best." Taylor smiled. "I'll leave you girls to it. Come say goodbye before you leave Taylor, I'd love to see the final results," Gail squeezed her hand and went back to undertake her last cut and style for the day. "Hey Miriam, do you mind if I film the makeover, it will help me get my makeup right later. As I said, I'm very rusty," Taylor asked. Miriam look around the salon and then back to Taylor. "Shelly... she's the owner, doesn't allow imagery to be taken inside the studio but in your case I'll make an exception. Give me your phone," Miriam held out her hand. Miriam set up Taylor's Galaxy S20 on the cosmetics table and adjusted it so that it faced Taylor who was reclining in the chair wearing a protective smock over her clothing, then she went to work. Taylor was delighted with the results. When she removed the smock and looked at herself in the mirror she looked nothing like the scarecrow who had stepped out of her bedsit earlier that day. All modesty aside she looked amazing; she was not a classic beauty but she was unconventionally alluring. Gail told her she was beautiful on the way out of the salon and gave her an air-kiss so as not to mess up her makeup. It was a short walk down Sawyer Avenue to her walk-up apartment but with all of her purchases she needed an Uber. She apologised to the driver for the short ride but she tipped him handsomely. She noted that the young dark skinned man was very attentive and took a particular interest in her ass when she bent over to pick up the packages. It just showed her how shallow men were in some regards. Not one man had paid her any attention when she left home this morning. A change of clothes, some hairstyling and an application of makeup had turned her from a scarecrow into an enchantress. Every man walking by looked her up and down appreciatively as she made the three trips from the Uber to her flat to unload her purchases. Taylor made space in the wardrobe and cupboard drawers for her new clothes; she pushed her second self's male attire aside to make room. She contemplated packing all of Taylor's male attire away but she would need it again in three months. She still thought of her current condition as temporary. Taylor opened up the makeup case she had purchased at Walmart and gazed upon it with wonder. She had watched Miriam turn her from a plain-faced homely woman to a captivating young lady using the magical notions, powders and concoctions contained in the cosmetics case. Now she needed to learn how to do it herself. She downloaded the video she had taken on her phone in the beauty salon onto her network and brought it up on one of the screens and set the makeup case, bushes and applicators up on a little side table. She took one last selfie and then wiped her face clean using face wipes. Three hours later she was confident that she could apply her own makeup and not end up looking like Ronald McDonald or the bride of Frankenstein. She looked quite attractive actually. She spent some time walking in her new heels to get used to them and practiced sitting with correct posture. Everything about being a woman seemed difficult and convoluted and she became exhausted with it after a while. It was late and she was tired and hadn't eaten but she had no appetite. She drank a beer while she checked her email and messages and then stripped and took a long hot shower ensuring that her hair stayed dry by using a shower cap. She slipped into her recently purchased satin and lace babydoll pyjamas, relishing the luxurious feel of the fabric on her flesh. She decided that her breasts and vulva needed further examination and rubbed out a nice orgasm before she fell asleep. Life as a woman was complicated but she had to admit that she had enjoyed today. There were eighty-nine days to go and she had a lot to do. The next day she woke up still feeling a little uncomfortable in her own skin. Coffee seemed to fix that. She spent some time in front of the mirror examining her body, Gail had done an outstanding job on her hair, it really suited her. Taylor was keen to use the makeup again to try some different shades, colours and techniques but she had work to do. Taylor fired up her network and started working. It wasn't lost on her that women were supposed to be especially good when it came to multitasking. She started to run the code she had recently edited through a debugging program and then pulled up her list of potential investors and put a line through Paddy McClintock, allowing the debugging program to run in the background. Taylor had taken his PostPay app to most of the big software companies and finance houses with little success. He was not interested in any of the places where young kids sat around in plastic chairs and bean bags wearing jeans and shorts and flip-flops. He didn't need software developers; he needed programmers who could adapt the code he'd already written and a market manager to get the retailers to come on board. It was now time for the new improved Taylor to try. It was time to see if the USB oracle or whatever it called itself could deliver on its promise to bring Taylor success and good fortune. She pulled up one of her letters of introduction and redrafted it using the correct pronouns and tidied it up a little. She had taken quite a few selfies last night while she was practicing her makeup techniques and she brought up what she considered to be the best of them and loaded it into her photo editing software. She played with the shade and colour intensity a little to improve it. She didn't feel guilty, why should she? Didn't women alter their appearance using makeup to make themselves look better so what was wrong with a little touch-up? Once again she silently thanked her parents for naming her Taylor. It would have been difficult, almost impossible, to replace Taylor's male identity with her own if he had been named Thaddeus or Arthur or some other masculine sounding name. She cast her eye over the remaining companies on her list and selected three of what she considered to be the best prospects and fired them off letters of introduction ensuring she attached a sample of her code and a copy of her picture. She crossed her fingers and went back to debugging. Around lunchtime she was starting to feel hungry so she showered, brushed her teeth and her hair and fixed her makeup. Last night she had, with help of her friend Google, mastered a few makeup techniques and developed a couple of distinctive 'looks'. She was wearing her 'day look' which made her face look fresh. Taylor slipped into fresh underwear, once again delighting in the feel of the silky garments on her skin. There were some aspects of being a girl she found quite delightful. It was cool out so put on some black spandex leggings having first put on a pair of stocking footlets. She rummaged through her purchases and found a pink long-sleeved t-shirt over which she wore the same ivory waterfall cardigan and a textured blue silk scarf that she had worn yesterday. She slipped her feet into the suede ankle-boots, sprayed herself with perfume and put on some earrings. Stepping outside into the brisk cool autumn weather she felt a sense of achievement and of peace and contentment. The trees lining her street had changed colour and were vibrant red, orange and yellow against the pale blue sky. The streets were busy, especially Milwaukee Avenue, and she noticed that she attracted more than a few appreciative glances from the men who passed her by. She wondered if all women felt that they were being ogled by the men around them. Except for the tight-fitting legging which accentuated her tight ass and long legs she was hardly dressed provocatively. She walked the few blocks to the Passion House Coffee Roasters and ordered a late breakfast and a large batch-brew coffee. While she waited for her order she fiddled with her phone. She checked to see how the technology finance companies were faring on the Nasdaq. Her brunch arrived and she tucked into it and sipped her coffee; she wasn't very ladylike shovelling the food into her mouth but she needed fuel, she couldn't remember the last time she had eaten a proper meal. Her phone pinged and she picked it up and was surprised and delighted to see an email from Bradley Freeman, the CEO of FreeCom, a finance technology company. He stated in his email that he was very interested in Taylor's product and had an opening at five o'clock that afternoon if she would like to come for an interview. Taylor replied that she would indeed like to come into FreeCom for an interview but she tried not to sound too eager. Her food tasted even better now that she'd had one positive response to her proposals but Taylor had been down this road before: excited at the prospect of getting a financial backer and then disappointed when the prospective client turned Taylor down. But this time it wasn't the gamer in a suit who would be attending the interview. It would be a sophisticated attractive young woman... if she could pull it off. Taylor went back to her home and pulled up her financials. She had spent more money than she had intended to yesterday and Taylor's credit card account was already substantially low before yesterday's splurge. If she didn't get someone to option her PostPay app soon she would be struggling to meet her financial commitments. She would have to get a day job. Taylor would be like the other schmucks writing code for some big software developer. Making a decent living but hating the job. She opened the debugging program she had left running while she was out and found a few improvements that she could make to her code so she got busy doing so. Every time she changed a line of code she needed to retest the app for functionality. It was a long and tedious task but to her it was like creating art. After a few hours she needed a break so she fired up the Vaio and inserted the alien USB drive. The red stones around the dull matte-black edge of the flash drive remained dark and unlit and the program window remained blank. "Eighty nine days to go I guess," Taylor snatched the USB out of the Vaio and tossed it into a drawer where she kept a plethora of computer peripherals and accessories. She checked the time and realised that she had better start getting ready if she wanted to make her appointment on time. She wished she had something better than the navy blue suit with chalk stripes that she had bought at Walmart yesterday but her funds were limited. It was nice, in simple sort of way. She fixed her makeup putting on a little more eyeliner and mascara to emphasise her green eyes then she stripped naked. Taylor carefully opened the package of L'eggs Silken Mist ultra-sheer run resistant pantyhose. The male Taylor was turned on by women's legs encased in nylon and her female doppelganger was not disappointed when she slipped the silken garment onto her legs. They felt delightful; the sensuous feel of the sleek fabric against her skin was wonderful. She pulled the gusset tight around her abdomen, they were sheer-to-the-waist and she admired the look of her buttocks and pubic mound sheathed in the delicate garment. She very naughtily rubbed her clitoris through the delicate fabric and the feeling was very enjoyable but she had things to do and couldn't afford to waste time playing with her body. She pulled a pair of white satin panties up her legs and smoothed them around her buttocks, the sensuality intensified by the feel of the pantyhose. She put on a matching satin and lace bra and a long-sleeve navy-blue satin blouse which she struggled to button because it buttoned on the opposite side to what she was used to. She stepped into the skirt and zipped it closed and straightened the hem which came to mid-thigh, a little shorter than when she had hurriedly tried it on in Walmart. Never mind; she hadn't met a man yet who complained that a woman's skirt was too short. She brushed her hair and put in some gold round earrings and put on the matching necklace and bracelet. She misted herself with perfume and then slipped into her plain black pumps with the three inch heels. Taylor had practiced walking in the shoes the previous evening between bouts of makeup practice. It wasn't really that hard; she had found four simple cues to walking in high heels: take smaller steps, put the heel down first, walk so that one foot came down directly in front of the other with her toes pointing straight ahead, and walk upright with improved posture. She couldn't imagine herself running down a cobbled street or skipping down a flight of stairs but with concentration she could get around quite confidently. Taylor summoned an Uber, put on her jacket, picked up a black leather handbag into which she had already tossed her necessities, and stepped outside to wait. She wished she had bought an overcoat and decided it would be her next purchase. While she waited for the car she again considered the encumbrances of living the life of a young woman. It was complicated and required a lot more attention to her appearance than being a man did but there was a certain satisfaction and enjoyment in the little rituals. When the car arrived she opened the rear door and climbed in and realised that she was very unladylike in her efforts. It was her first time in a skirt outside the house and she realised that she would need to pay attention to that aspect of her ensemble. She was sure that the gentleman passing her house enjoyed the panty flash and acres of thigh she presented as she climbed into the SUV so she needed to exercise a little more decorum. She checked her phone while the driver took her down to The Loop to the offices of FreeCom. She took more care alighting from the vehicle and did so with propriety and dignity but she did notice that a couple of men turned her way to watch. She went inside and checked the directory and then entered the elevator to take her to the eighteenth floor to the FreeCom offices. Two men waiting for the elevator stood aside to let her enter the car first. One stood beside her during the ascent and the other went into the back corner and fiddled with his phone but she could feel his eyes on her legs and ass. Men were pigs but she had to admit that male Taylor did exactly that, he ogled women whenever the occasion presented itself. Taylor presented herself to a pretty receptionist in the entrance lobby and the receptionist checked her computer screen and smiled back at Taylor confirming that indeed Mister Freeman did have an appointment with her at five o'clock. She put a phone to her ear and pushed a button and announced that Taylor was present and then she directed Taylor to an office at the end of the corridor. It was one of the few single offices on the floor. Most of the floor space was taken up with open plan workstations where men and women were busy tapping keys and pointing at screens. A small glass-walled conference room was filled with a group of men and women in their shirtsleeves standing around a whiteboard contributing their input while a tall handsome young man wrote code on the whiteboard with a marker. Taylor smoothed her skirt and straightened her jacket before she entered Bradley Freeman's office. He was on the phone but smiled at her and waved her in, pointing to a cluster of chairs arranged around a coffee table in the corner of the office. Taylor tried to sit demurely with her ankles crossed as she had practiced at home, but she was wearing leggings at the time and hadn't had to deal with an inherently delinquent skirt that kept wanting to ride up her thighs. She gathered the material under her legs and was able to stop it but she saw that Bradley was amused by her antics. Taylor blushed; this wasn't how she wanted the interview to proceed. Bradley hung up the phone and came around from behind his desk and beamed at her and offered her his hand. She wasn't sure if she was supposed to stand but she didn't want to have to wrestle with her skirt again so she remained seated, returned the smile and lightly shook his hand. "I'm Bradley Freeman and you're Taylor Averille so that's the introductions out of the way so let's get down to business. I like what you sent me," Bradley took the seat beside her. Taylor blushed and Bradley looked confused but then a smile lit up his face when he realised that she had got the wrong idea. "I meant the code sample you sent me Taylor; although I will admit the picture was nice too but it doesn't do you justice." Bradley grinned. When Bradley smiled he was extremely handsome. He looked to be in his late thirties or early forties, he was fit and tanned and had a full head of hair that was either bleached by the sun or had been professionally highlighted. He had dark eyes and full lips and Taylor was confused by how she felt about him. This was the first time that she had been close to a man in an intimate setting since she had transformed. Male Taylor, despite his interest in nylons and lingerie, had never once considered wearing women's clothes and certainly had never been attracted to another man. But there was no doubt that Taylor was attracted to Bradley Freeman. The monolith or the oracle or whatever the USB called itself had not only changed Taylor's body, it had also changed her perspective. Had it also had changed her sexual preferences? "Well thanks for the compliment Mister Freeman but can you tell me what you liked about my code?" Taylor was here to get commercial backing not to flirt. "Well I've seen similar apps of course but your coding is clean, it's sharp and it's good. Some of the other programs I've seen are boated and clumsy. You've shown me the front end; what can you tell me about the work engine?" Bradley asked. The pretty receptionist entered and placed coffee on the table and Bradley poured for them both. Taylor used the same spiel she had used on Paddy McClintock and other potential investors before him, but this time her quarry seemed engrossed in what she had to say. "PostPay takes a percentage of the profit from the retail sales and collects interest on the loan and collects late fees which is how most of these lending apps work but the interface isn't anywhere nearly as clunky as most of the others. Once the customer makes the purchase the item is immediately routed from the vendor's warehouse and picked up a courier for delivery. The customer gets almost instant gratification," Taylor started to explain. "The software resides on a standalone network but interfaces with the customer through the app, and the vendor, delivery agent, and lender seamlessly through their own network. Everyone makes a small profit and the customer is more likely to pay out the loan quickly and make more purchases with the app. The more purchases made the more money everyone makes and the customer is paying the best interest rate available," Taylor finished her blurb and took a sip of coffee. "What I see as the biggest advantage of my app is that if a customer wants to make a purchase from a vendor that isn't signed up to PostPay, the software will locate the nearest financial institution that supports PostPay and will make the transaction on PostPay's behalf, splitting the profit." "The customer just scans the app on a credit card scanner and the transaction takes effect seamlessly. The vendor is informed that PostPay has sanctioned payment through an accredited third party financial institution. Hopefully the vendor signs up to PostPay to cut out the middleman, bringing more retailers into our fold and increasing profits," Taylor completed her pitch. "Well it looks like a sound financial investment to me, but tell me, why haven't any of the other big players taken up your proposal?" Bradly asked. Taylor balked. She didn't want to use subterfuge but she had no choice. "I was in partnership with my cousin for a while. I did most of the program development and coding with his assistance. He did the legwork, trying to garner support and investment from the finance technology companies. He fell flat and lost interest in the project so I fired him. He currently has no ties or pecuniary interest in PostPay," Taylor explained. "It's kind of embarrassing. He has the same name as me." Taylor blushed. "But I bet he isn't as comely." Bradley smiled. Taylor frowned. "Hey, it was meant as a joke. My family has two Leslie's, both cousins, same as you. One is an oversize truck driver and the other is a yoga instructor and it might surprise you to know that the woman is the truck driver. One should never make assumptions," Bradley thought that he had diffused the situation but Taylor still felt uneasy about the compliment. "Come on, let me show you around the place." Bradley arose and Taylor followed suit. She appreciated Bradley looking away from her as she struggled to stand with some modicum of decorum. The high heels and short skirt were giving her more grief than she had counted on but it looked like they may have done their job. She could just as easily have come to the interview dressed in a pantsuit and flats but there was doubt that wearing the skirt and heels worked in her favour. Bradley took some time to show her around the open plan office where a lot of the workstations were vacated as it was past quitting time. He showed her the conference rooms and coding rooms where, he explained, most of the brainstorming and concept development took place. Next he showed her the management offices and the affiliated company executive offices where Taylor would work if her bid was successful. The fourth cup of coffee she had drunk that day in Bradley's office was demanding release and she spied the ladies restroom and excused herself. She went to a stall and did her business. When she came out an older attractive slim woman was standing at the vanity putting on lipstick. She was wearing a designer short-skirted power-suit and the red sole of the killer heels, visible as she leaned close to the mirror, indicated that they were Christian Louboutin. The woman had defined cheekbones and full pouty lips onto which she was applying blood-red Guerlain Rouge Jewel Lipstick. Her jet-black hair was styled in a severe shoulder- length bob. Taylor washed her hands and fixed her own lipstick while the woman beside her liberally sprayed herself with Clive Christian Number No1 perfume. The woman dropped the perfume into a Hermes handbag and turned to study Taylor. "What are you doing here Kmart?" The woman looked down her nose at Taylor. The woman's accent was European or Slavic, almost exotic. "I'm Taylor Averille and I have a meeting with Bradley Freeman." Taylor smiled and offered her hand. The woman just stared at Taylor's outstretched hand like she held a turd in it. "And they let you in here dressed like that?" The woman sniffed. She turned her back on Taylor and strode out of the restroom, her heels clicking on the tiles. "Bitch!" Taylor whispered under her breath. This was the first time Taylor had encountered animosity from another woman but she had only been a woman for two days now and she knew women could be bitchy. When Taylor came out into the corridor Bradley Taylor was deep in conversation with the bitchy woman. Bradley's eyes lit up with a genuine smile when Taylor came out of the ladies room. "Ah, Taylor Averille meet Veronique Pascal... Veronica meet Taylor," he made the introductions. Veronique put out her hand and Taylor took it and Veronique pulled her close and gave her an air-kiss on both cheeks. "Wonderful to meet you." Veronique's smile was painted on her lips. "Veronique. That's a very exotic name." Taylor returned the smile. "It's French but I am Ukrainian by birth, I left the Ukraine when I was a girl. I abbreviate it to Veronica; some Americans find it difficult. Taylor sounds like it originated in the South. Are you from Arkansas? Tennessee? Alabama perhaps?" Veronique said disparagingly. "Born and bred in Chicago Illinois. Go Bears!" Taylor made a half- hearted air punch. "Hey! A smart, attractive woman who follows football." Bradley gave Taylor a high five. "Real women love football; smart women follow the bears," Taylor recounted a meme she had seen. "Ah, you are referring to the game of fumble-ball, drop-ball, throw-ball played by large men with padded shoulders and small brains, not the beautiful game." Veronique turned down her lips. She looked like the villainess Katinka Ingabogovinanana from the Zoolander movie and Taylor supressed a smile. "If I take up Taylor's proposal you ladies may end up working closely. Veronique is FreeCom's marketing manager," Bradley explained. "Well it was wonderful to meet you Taylor, but I have a dinner engagement so excuse me. See you tomorrow Bradley." Veronique turned and walked away, presenting her curvy figure, tight derriere and long legs sheathed in black fully-fashioned stockings. Bradley tried not to stare but couldn't help it. Bradley noticed that Taylor saw him watching Veronique as she walked away and he blushed. Taylor burst out laughing. "She's something alright. Total bitch but the best marketing manager in the business." Bradley grinned. "Yes. She's something alright." Taylor smiled. Bradley glanced at his watch and looked surprised. "Wow! I didn't realise it was so late. I hope I haven't kept you from something important?" Bradley looked genuinely concerned. "Nope. Just a microwave dinner and an evening refining my code." Taylor smiled meekly. "Hey. Look... I don't want to be forward; we've only just met. But would you like to join me for dinner? Nothing fancy, just a steak and a beer at Gibsons." Bradley gave Taylor that boyish grin. Taylor looked apprehensive. "You can tell me more about PostPay; make it a working dinner and then I'll drop you off home." Bradley's smile widened and Taylor couldn't help but return it. "Great. Let me get my things from my office. Do you mind calling for a reservation while I pack up and get my car brought around front?" Bradley put his hand lightly in the middle of Taylor's back and guided her back to his office. The ride to Gibsons in Bradley Freeman's late model BMW was comfortable despite Taylor having to constantly adjust her skirt. She wished the hem was just two or three inches longer, it's not like she was flashing her panties but the skirt rode high on her thighs whenever she sat down. Bradley Freeman seemed very amused by Taylor's efforts at maintaining her modesty but he was too much of a gentleman to say anything. Taylor had managed to snag a table away from the crowd and she and Bradley each grabbed a glass of Gibsons Gold Helles Lager at the bar before they sat down. They ordered steaks and Bradley splashed out on a bottle of Rutherford Hill Merlot. The alcohol flowed freely as did the conversation. Bradley was very interested in hearing more about PostPay but didn't go so far as committing FreeCom to the startup. They soon exhausted that discourse and moved on to talking about their personal lives as new acquaintances are want to do. Taylor found it easier than she expected to adopt her male alter-ego's identity as her own and just change the gender to fit. She was born in the suburbs of Chicago twenty-five years ago and had no siblings, her mother and father had died in a helicopter crash over the Grand Canyon five years ago. Other than her uncle and aunt, her cousin with the same name, and two other female cousins she has no other family. She had completed her schooling at the Illinois Institute of Technology and worked for a few tech companies but has been working full time developing PostPay for the last six months, living off her parents life insurance (which was nearly exhausted but she didn't tell him that). She lives alone in one a bedroom apartment on North Troy Street and does not have a boyfriend. The story she told was true, except that until two days ago she had been a man not a woman. Bradley Freeman had also graduated from IIT but obviously a lot earlier than Taylor. He too had worked at various tech companies whilst undertaking a business degree. He had started FreeCom as a boutique tech company which diversified into financing tech startups and taking them on as subsidiaries. He was thirty eight and divorced with no children, he didn't say if he had a current girlfriend but Taylor doubted that someone with his good looks and outgoing personality would remain unattached for long. The wine on top of the beer was starting to affect her as was Bradley's smooth talk; he was an engaging and entertaining conversationalist. They spoke about current events and of course they both had a passion for the Bears who were having one of their best seasons in 2018. Taylor was confused by her attraction to the man. She was still coming to grips with being a woman. She had managed the physical changes remarkably well but the changes to her psyche were a different matter. She found herself admiring men as well as women. Was she bisexual? She supposed that at some stage she would find out. She couldn't help but wonder what it would be like to have sex as a woman. The two orgasms she had experienced so far were wonderful; the build-up was far more protracted and the climax itself was intense and prolonged and although her orgasm originated in her clitoris, her whole body seemed enmeshed in the phenomenon. Time flew and Taylor was enjoying herself; really enjoying being a woman possibly for the first time. They finished the evening with two rounds of Jack Daniels and by then Taylor was well and truly inebriated. Bradley seemed to be handling his drink better but he was in no condition to drive. "Look Taylor, I'm sorry. I promised you a ride home but I'm obviously in no fit state to drive. I'll get us a car and drop you off. I'm not blaming you but I've found your company so delightful that the evening has got away from me." Bradley gave her that grin again. "Nonsense Bradley. I'm a big girl and I can find my own way home; I'll get an Uber," Taylor countered. "Don't be like that. You know I don't want anything to happen to you, let me at least see you safely to your door," Bradley said sincerely. Taylor stood up and realised that she was a little tipsier than she thought. "A car might be a good idea. But let me pay for half. You order one while I visit the restroom," Taylor said. She had to concentrate on walking and wished she could take off her heels. She made it back to their table without incident. Bradley gallantly put his overcoat around her before they went outside as it was bitterly cold and windy. The town car was idling at the curb and he got the door for her. Taylor was too cold and tipsy to worry about her dignity as she scrambled into the back of the car, all ass and heels. Thankfully the car was toasty warm. Bradley bundled in after her and slammed the door. Taylor gave the driver her address and began to struggle to get out of the coat. "Here; let me help you with that," he leaned into her and put an arm around her to get hold the far side of the coat while Taylor bent forward slightly and tried to get her arm out of the sleeve. They both started to laugh at the absurdity of it. Taylor's arm sprang free and she fell back, pinning Bradley's arm behind her which elicited another bout of raucous laughter. Bradley tried to pull his arm free causing Taylor to fall against him, her face inches from his. She gazed into his dark eyes and he into her green eyes. She could see the question on his face and she answered it by pressing her lips to his. He kissed her and held her tight against him. Taylor pushed the bunched overcoat out of the way so she could feel his body, her breasts pressed into his chest and she felt her nipples begin to tingle. It felt different but it felt nice, as did Bradley's tongue in her mouth. He was using just the tip, being gentle, sensual. It was different being the submissive acquiescent partner but it felt so right. Taylor returned Bradley's kiss and when his hand went inside her jacket she didn't stop him. He unbuttoned the top of her blouse and his fingers fumbled with the catch on her bra. They were cold against her skin but she didn't want him to stop. When Bradley hefted her breast and stroked her nipple she gasped into his mouth. The feeling was uniquely pleasant, she felt her nipple engorge. The car braked suddenly and the couple were jolted. Bradley abruptly withdrew his hand and broke the kiss. Taylor looked bewildered. "What did I do?" She searched his face. "You? Nothing. It's what I did. I'm not that guy Taylor. This is wrong. You've been drinking, I'm the person in authority and you want me to back your startup," Bradley shook his head apologetically. "So you're the one with the power in this situation, is that right?" Taylor asked him. The time spent in the fresh air and the back seat tussle had sobered her up somewhat. "I'm sorry Taylor," Bradley said humbly. Taylor scooted the overcoat out of the way and clambered over Bradley so that she was straddling him. She put her hands on either side of his head and lowered her face to his. She crushed her lips against his and slipped her tongue into his mouth. "Who has the power now?" She smiled down at him. "You're amazing." Bradley smiled up at her and Taylor lowered her face to his and kissed him passionately. She felt him cup her buttocks in his strong hands and squeeze; she was also pretty sure that she could feel his erection pressing against her. They kissed for a while and then the car slowed down. "North Troy Street you love birds; you wanna give me a house number?" the driver said, the amusement in his voice evident. "Just there." Taylor swivelled in Bradley's lap and pointed to her walk- up. She leaned down to kiss Bradley again and the car stopped. "Are you coming in?" she whispered. "I'm not sure I should," Bradley said bashfully. "Well I figure you're far too much a gentleman to leave a girl half- cooked and I'm not going to do the walk of shame from your place." Taylor smiled at him coquettishly. "Are you sure?" Bradley searched her face. Taylor nodded and untangled herself from him. "Come on up Bradley. No obligation. Just two adults enjoying the perfect end to a lovely evening," Taylor said soberly. "No obligation. This is nothing to do with PostPay?" Bradley restated. "I'm not a hooker Bradley. I'm not for sale," Taylor said solemnly. Bradley looked both anxious and apologetic. "I'm joking you dummy. Come on." Taylor leaned in and kissed him quickly. She took his coat and stepped out of the car and put the coat on for the short trip to her front door while Bradley took care of fare. He got out and pulled Taylor into his arms and kissed her. He started to shiver. "Let's get in out of the cold." She allowed Bradley to put his arm around her and she led him to her front door. She had to disengage to find her keys in her handbag. "Are you sure? Are you positive?" Bradley asked again. Taylor unlocked her door and put out her hand. Bradley took it and she ushered him inside. The alcohol had mostly worked its way out of her system and Taylor was feeling both excitement and trepidation. She felt both licentious and inquisitive. What would it be like? She would soon find out. Taylor's small apartment was lit only by the glowing screensavers on her workstations and she made no effort to turn on any lights. She shucked out of Bradley's overcoat and took his hand and led him to her bedroom. She switched on the bedside lamp and turned around and Bradley pulled her into his arms. They kissed passionately, his hands once again finding their way inside her jacket and blouse and began to caress her breasts. Taylor sighed as her nipples hardened and tingled. The feeling was subtly erotic and it began to spread. She felt herself becoming wet. Bradley eased himself out of the embrace and started to undress and Taylor took off her jacket and hung it over the back of a chair. "Don't take off any more clothes. I want to do it; it's like unwrapping a present." Bradley grinned. He kicked off his shoes and socks and shucked out of his shirt and pants. Taylor was amused. Now that she was in the obverse position she realised that there was no way that a man could undress erotically like a woman could. Bradley was stripped down to his briefs, the bulk of his semi-erect penis bulging the pouch. Taylor wanted to touch it. To reach out and feel the heft and heat of it and the anticipation was making her wet. Bradley kissed her again and then began to undress her. He undid the remaining buttons on her blouse and removed her brassiere. He paid some attention to her bosom using both his hands and mouth. He kissed her soft milky breasts and his lips found her nipples and Taylor moaned when he began to use his tongue and then his teeth. Taylor guided his face from one breast to another in turn, as her nipples became highly sensitive. Bradley continued to use his mouth on her breasts as he unzipped her skirt and let it fall to the floor, pooling around her ankles. Then he kissed her again and held her close; she could feel his erection pressing against her body. It was warm; his body was cold. "Let's get under the covers," Taylor whispered, kicking off her heels. She hooked her fingers in the waistband of her pantyhose, intending to peel them off along with the panties she wore over them. "Leave them on. They'll keep us warm," Bradley whispered in her ear and squeezed her buttocks. "Really? Is that all?" Taylor smiled coyly. "Ok. I like them." Bradley smiled sheepishly. "I get it," Taylor whispered and squeezed his cock through his underpants. She got it. Her male alter-ego also liked women to leave on their nylons during sex and she had to admit that she liked the silky feel of them too when Bradley stroked her buttocks and thighs. She was becoming wetter and he hadn't even touched her there yet. They slipped under the sheets and pulled up the covers and Bradley lay on top of her. He kissed her and she liked feeling his hard body lying on top of hers. He slipped his hand between their bodies and tugged at her panties. Taylor scooted up a little and let him slip them off then she took off his briefs. The feel of his hard cock pressing on her thigh was very erotic. She reached for it, feeling the girth and the heat and the pulse of the powerful appendage. She scooped a bead of pre-ejaculate and coated his glans with the slippery fluid. She began to stroke it and it was Bradley's turn to gasp. Bradley put his hand between Taylor's legs and she opened them wider for him. He massaged the tops of her thighs, lightly stroking her flesh through the gossamer pantyhose. He pressed his lips to hers as his fingers found her sex. She was wet; her secretions had soaked into the crotch of her pantyhose. He opened her labia and pressed his finger on her tender nubbin, circling it through the translucent material. Taylor groaned and lifted her hips up off the bed, encouraging Bradley to press harder on her clitoris whilst she writhed beneath him. She stroked his manhood, feeling it become fully tumescent, the veins pulsing under the sleek delicate dermis. Bradley drove his tongue into her mouth and snagged a nail in the diaphanous pantyhose and tore a hole in the crotch. His finger snaked inside and circled her clitoris. Rings of pleasure spread from between Taylor's legs and she felt a yearning, a need to feel Bradley inside her. Taylor guided Bradley's phallus to her vulva and Bradley pushed it inside the hole he had ripped in her pantyhose and nestled his glans in the folds of her labia. She bit her lip and winced as Bradley pushed the head of his penis inside her vagina. "Am I hurting you?" Bradley said, the concern in his voice evident. Taylor wrapped her nylon-sheathed legs around his waist and lifted up her pelvis, slowly driving Bradley's hard cock inside her. She cried out as Bradley's penis tore her hymen. She hadn't thought about the fact that she was a virgin; it had never entered her mind. The pain was short and sharp and the wonderfulness of his cock filling her vagina and the magnificent sensations that erupted from her clitoris as his pubis pressed on it surmounted the pain which became a dull ache. "Oh, Taylor you are so tight," Bradley groaned as his cock slid in and out of her velvety sheath. The feeling was indescribably sublime and Taylor clung to him with her arms around Bradley's neck and her legs locked around his waist. She encouraged him, deliberately rubbing her nylons on the delicate skin of his flanks. Bradley didn't take long to climax, which Taylor didn't mind one bit. She had been on the edge of extremis since he had entered her. The dull ache from her shredded hymen, the deep sense of fulfilment that came from deep inside her vagina and the scintillating rings of intense pleasure radiating from her clitoris combined to generate an orgasm of tumultuous gratification. She felt Bradley's cock swell and quiver inside her and she knew that he was ejaculating. This spurned her on and amplified her pleasure. She screamed with the intensity of it and clung to Bradley, shaking and quivering as he jackhammered his cock in and out of her sodden cleft. Bradley kissed her hard and she returned it, slipping her tongue into his mouth. They remained clenched together until their climaxes subsided. They kissed and petted for a while but they were both exhausted and it was late. They fell asleep in each other's arms. Taylor awoke the next morning, her vulva sore but in a contented sort of way. She put out her hand but the bed was empty, however she could still feel the warmth of Bradley's body on the bedclothes. She heard a noise and Bradley emerged from the bathroom. He was freshly showered and fully clothed. He came over and sat on the side of the bed and leaned over and kissed her. "Sorry; I bet I have morning-breath." She smiled up at him. "Nonsense. Thank you for a wonderful evening." He kissed her again and mussed her hair playfully. "No, thank you," Taylor stretched. "When you're up to it call me later today and arrange a meet. Let's talk some more about PostPay," he said. "After lunch?" Taylor asked. "Better yet; let's do lunch. I'll text you ok?" Bradley leaned down and softly kissed her hair. Taylor nodded. "By the way; I think you started your period," he whispered in her ear. "I'm sorry," she frowned. "Don't be sorry. You're beautiful." He kissed her again and then got up from the bed and left. To be continued