Photograph Part One free porn video

Photographs. By Trish 2020. "Hiya Mike," Bob Jeffreys said with a friendly grin as he opened his door. "Come on in, thanks for coming round." "I've got nothing else on Dr Jeffreys," Mike said cheerfully commenting. "Wow nice place," as he was shown in. "Yeah, I like it and it will be perfect once I've got properly moved in," Bob said, "it's still a bit of a bomb site just now, but a massive improvement on than that tiny flat I was renting while the builders were knocking the shit out of this place. Tea, coffee or something cold?" "Tea would be good please," Mike replied, "so what's up with your computer?" "Since it crashed yesterday, it's not seeing any of the data in my surveying tools," Bob told him as he guided the him into the kitchen. Even though Bob did not know Mike very well in person, he had learned rather a lot about him since he unexpectedly caught his alter-ego on camera. Given their shared taste Bob had racked his brains for an excuse to speak to him privately without raising suspicions, and his computer problem gave him the perfect opportunity. With the personal nature of the topic he wanted to ask Mike about it was not something he had felt comfortable about bringing up while he lived in such close proximity. "Is it Windows?" Mike asked. "Yes Windows Ten, one of the special versions intended for workstations." "It's probably just the drivers," Mike said in what Bob classed as his nerd mode. "The auto update on Windows 10 regardless of the version is rather heavy handed. Are you using specialised package that needs to download propitiatory software for the driver package?" "Couldn't tell you, but it is a custom built GIS package I had written specifically for the sort of jobs I do," Bob laughed. "It cost a bloody fortune but I made it back on time alone on the first job." "No support?" Mike asked surprised. "With Covid restrictions they can't get anyone out until Monday," Bob said pulling a face. "And I need to compile some data ready for a meeting Monday morning." He shrugged. "I could do it long hand but I really don't want to spend a day plotting on a paper map, and then another couple of hours writing the site report. If you can get my GIS working it will process mapping in half an hour." "I'll have a look chances are its just Windows update over writing the drivers so it can't see the devices." "And if its not?" Bob asked. "Then I'll have to jump over the system," Mike said confidently, "I've written add-ons for GIS so I understand how they work, it might take me a while but I'll be able to fix it." "Any idea how long it will take if you have to get into the nuts and bolts?" Bob asked with a certain amount of fake anxiety in his tone. "How long is a piece of string?" Mike shrugged. "Can't say how long until I've had a look, it depends on how deeply I have to jump into the system," Mike said as Bob waved him to a chair in a comfortable professionally equipped kitchen. "If it's a straight forward driver issue around half an hour, if it's anything more complex a couple of hours or so I guess?" "If you can get it working today, I can analyse the data tonight and write my report tomorrow," Bon said. "You do have all your files and data backed up on an external drive right?" "I have." "Great," Mike said, "In that case if its done a full on Windows number and really messed up the package. Rather than wading through everything, it will probably be quicker if I just uninstalled the corrupt version and do a clean install from a fresh download assuming you have the set up disk or link?" "The disk that came with it?" Bob asked. Mike nodded, "Yep the one you used to set it up in the first place." "Yeah I've got that." "Sweet, I'll know more when I had a look," Mike said. "But one way or another you'll have your data by tea time." "Marvellous, so any plans for the summer?" Bob asked getting out a couple of mugs. If Mike had something planned then it was pointless bringing up such a touchy subject and potentially throwing away the chance of getting what he wanted later in the year. "Not now. I had planned to go travelling for a year, before coming back for my masters, but what with the Covid that's been sunk so I think I'm going to apply to see if I can bring my masters forward to this year." "Makes sense in a depressed jobs market to stay in education and get a higher degree," Bob said. "Thankfully with planning on travelling I've got some savings so I don't need to find a job in the short term because there are no well paid summer jobs around for postgraduate students this year, well other than flipping burgers," Mike shrugged, "Any real companies that are taking on staff aren't interested in someone like me who'll probably be gone by the Autumn." Bob nodded. "Yeah, I saw on the local news the other night that a lot of students are complaining that finding short term work just now is a shit sandwich." Bob was a self employed landscape surveyor who primarily worked for corporate clients assessing sites geographic suitability for development, and business wise he was far enough up the food chain not to have been that badly affected by the virus. "So what have you been up to during the lockdown?" Bob asked. "Other than completing the last couple of theory papers for my degree, and catching up on all the books I wanted to read sweet FA," Mike said. "Thankfully I got my industry placements finished before this started, and with doing a primarily a constant assessment degree, we had or only exam in January, so I've not had the finals issue that has bollocks a lot of students." "What did you get?" "Unofficially a first, but the results aren't officially published until next Monday," Mike said with a deprecating smile. "Which is nice, just wish my dad was here to see it." "Yeah, Mrs Javid in the shop mentioned you lost your father not long after you started at the university," Bob commented as Mike filled in a little of his back ground of his fathers accident. "At least on a motorbike it was was quick which was a blessing after my mother when I was a kid," Mike told him, before changing the subject asking. "What made you buy this place?" "My grandparents parents lived just up the road and when I was a boy I used to play with Mr Thomas the dentists kids when I was staying with them in the summer, and I fell in love with the big garden. When I saw it for sale after my divorce was finalised I thought why the hell not, since it pretty much fitted my needs," Bob told him as Mike finished his tea and asked, "Where's the computer?" "Its in my offices, this way," Bob said feeling pleased that Mike had unwittingly confirmed that he had no family ties. "Other than this kitchen and a large dinning cum reception room for the odd occasion when I need to host clients, I'm using the ground floor primarily as my business premises. This place was originally a dentists practice, so it made sense to use down here for my business rather than having a separate office, especially as the other floors were two flats for Mr Thomas and his family, and a small one for his assistant." Bob led Mike into his office space at the back of the house looking over a large secluded garden. It was a nicely arranged three room suite. One was obviously a store room full of expensive looking equipment, the second was set up as a meeting room, and finally there was a large airy office, with a massive dark wood L shaped desk in front of a leather executive chair. Sat in front of the desk were a pair of comfortable chairs with a low table between them. Other than a huge monitor positioned so it could be viewed from the desk one wall was mainly filling cabinets, while other was mostly framed photographs, certificates and shelves displaying objects from around the globe. Seeing Mike looking at the pictures, Bob chuckled. "I know its a little ostentatious to have an 'I love me wall' but its kind of expected in my line of work as it displays your value without rubbing a clients nose in it." Mike nodded noticing that between the doorways to the meeting room and the one they came in and facing Bob's desk was a secretarial station with a PC, a professional laser printer/scanner, a complex looking phone, and a small filing cabinet. "It's the work station on my desk," Bob said. "Okay let me look," Mike said slipping behind the desk and booting up the computer to display the start up modules and configuration. As it started he saw that it was pretty standard workstation system running on the Windows 10 Pro architecture. After gazing at the screen for ten minutes or so as he flipped through a numerous diagnostics pages, and scanned the documentation that Bob got with the package Mike looked up and said. "Yeah, its a typical bloody Windows issue! You got unlucky Dr Jeffreys, Windows update decided to claim the system while the GIS software was updating the driver packages and conflict between the two has made a right mess of things." He glanced back at the screen clicked yes. "I can fix it easy enough long hand if you have any data in here you can't afford to loose, but if you have it all the backed up off line, the simplest and probably quickest way will be to just uninstall your GIS package completely, and do a clean reinstall from scratch. It's your choice?" "What would you do?" Bob said, mentally rubbing his hands together that everything was going just as he hoped. "It's six of one half a dozen of the other. If it was mine I'd probably do it long hand for fun. Its going to take a couple of hours regardless what route we go but the reinstall will probably be quicker in the long run," Mike said, "and easier. If I debug by hand because I don't know the exact subroutine packages there is always a chance I'll miss something as the documentation you've got from the company appears to have been written by an idiot. Although the uninstall and me cleaning out all the left over files and registry entries will take about an hour, ones its clean slate according to this the reinstall it will do everything automatically." "Do a clean install then," Bob said, remembering how long it took last time he knew he'd have more than enough time push the discussion onto what he wanted to ask Mike about. "Okay, once I run the set up package it will trigger the download and install the latest version of the GIS suite. As the system reinstalls, according to this it will automatically include all your listed peripheral software," He looked at the screen and click a few boxes, and then added as the computer restarted. "I just told windows to hold updates from now on until you tell it to, that way you'll be able to let it do its thing when you're not using it." He looked at Bob. "Last chance to say no?" "Reinstall it." "Great," Mike said with his fingers flying over the keyboard. Bob found it fascinating watching his face and he muttered things like, "Why do it that way?" and, "Moron," at the unknown programmer who wrote the system. After about fifty minutes of intense concentration Mike looked up saying. "There you go its uninstalled, once it restarts, it will automatically download and install the new software. It will probably reboot a couple of times over the next hour or so, but once its done it will shut its self down and then all you'll have to do is just restart it with your data back up plugged into the USB port and it will import everything, and you'll be back in business." Standing up Mike said to Bob's astonishment, "Job done. Like I said all you need to do its plug in the backup when it shuts down for more than five minutes and restart it." "Already?" Bob gasped, adding, "Last time it went haywire like that, I got a tech out to fix the fucking thing, and it took him six hours to do what you've done in under an hour?" "He was probably miking the company, a lot of these mobile technicians are agency staff on zero hours contracts so they take as long as they can," Mike said. "Do you need anything off the camera?" He nodded at the expensive camera on the window-ledge. "I can always pop out the card and import them into the other PC. Sure its not set up for graphics like this one but it will let you look at them?" He grinned and said, "Want your chair back?" "No that my personal camera, I was shooting some birds on the feeder this morning," Bob said switching places and relaxing into his big leather chair waving Mike to one of the other chairs facing him. "And they can wait. Your degree is business IT right?" "Yeah, the degree name is a little misleading though, because I opted for the software design and development for business stream rather than Business and IT," Mike said sitting in the very comfortable chair. "Well having just seen you work, and with what you said about needing a job it occurred to me that if you don't mind doing office type work, I'm looking for a long term secretary cum clerk," Bob offered. "Since Laura my ex traded me in for a newer model and I relocated back here from London I've been using agency staff while I was in a temporary office in town, but now I have a permanent office again I really want someone trustworthy on a longer term basis." "Let me think about it," Mike said, not wanting to sound to eager. "For how long?" Sure office work was not his field but getting even a few hours regular paid work would mean he might not have to dip into his savings after all. "I'm looking for a year or two, but I need someone now. I'm offering ?25 an hour, and I'll need about twenty hours a week," Bob said casually dropping the wage bait in the water before adding. "If that interests you?" "I'm interested but it's not really my field," Mike said. "Sure I had to do office skills for business in first year, so I can type twenty five words a minute and I know what to do, but my degree is in software design for business applications." "It's close enough, and you do need a job right?" Bob said with a smile. "Putting it bluntly yes," Mike admitted, "I'd rather not spend the next four months sat on my arse in the house playing mind numbing computer games." "Can't say I blame you for not wanting to do that. I've been lucky because I managed to keep working through most of lockdown, but that first month when all businesses were closed and couldn't go to my office I was going bonkers in that tiny flat." "Still better than being stuck in a house with two medics discussing gruesome happenings at the hospital, and a wacko art student, who played Bob Marley and smoked pot all day," Mike grumbled. "I'd argue that," Bob said with a chuckle as he added, "I don't need a super secretary, just someone to deal with basic day to day office tasks, filing, typing, writing up my expenses, keeping the diary and phone answering." "I can do that, probably not as quickly as a trained office worker, but I can do it," Mike said mulling it over, and the pay was a good motivator because it was a lot better than he'd get in McDonald's for twice as many hours. Bob enjoyed the play of thoughts on Mikes face until he said, "Okay I'm willing to give it a try, when do you want me?" "As soon as, but hold your horses a moment. If you're going to take the job Mike, I'm going to be trusting you with access to often highly confidential material. It's not uncommon for me to be surveying sites that have not been announced as being assessed for development. I need to be sure you are honest with me, because the companies I deal with make decisions on my site reports that are worth many millions of pounds, and the contents of the summaries that you'll be typing up are sensitive both financial and commercially." "I understand Dr Jeffreys," Mike said. "Actually that element of business is something I am familiar with because we covered confidentiality agreements in great depth as part of my degree. Business IT systems by their nature have to be secure, because they often contain commercially sensitive information." Bob nodded and then decided to take the bull by the horns, and asked quite bluntly. "Okay then Mike, tell me honestly, are you gay? It's just I never once saw you with a girlfriend either at your place, or when I saw you in the town?" Mike was gob smacked by the question, he could not believe that Bob had just asked him that, because his sexuality was hardly relevant to his access to sensitive information. Although he felt he should protest, seeing the prospect of a well paid job in front of him he bit his tongue and said. "No I'm not gay," he shrugged, "I've always been more interested in chasing a good degree than chasing a girlfriend." Bob nodded. "So you're a straight cross dresser then?" The calm manner that Bob said it shocked Mike even more than the last question and said blushing brightly, "No, course not," mentally crossing his fingers. Mike was careful, no one could have found out his dirty secret. "Sure you don't want to change your answer," Bob said with a friendly smile as he pulled four photographs from his desk and slid them one at a time over to Mike. "Michele?" Mike felt like his stomach had fallen out as he looked at the first photograph gasping, "Oh my god how?" Looking at the white faced trembling figure over his desk Bob smiled tapping the first one he took. "This is my favourite one because it was the first. I was working late on a report and happened to look out of the window and the moon was perfectly full and sat between the university clock tower and the Cathedral spire so I grabbed my camera and tripod and set up a few night shots. Next morning I put the images on my big screen, there you were looking all girlie in your window and after that I found myself keeping an eye out for you." Since the photo's showed him wearing the four outfits 'Cheryl' owned the pictures were obviously taken over a period of time, which made him ask just how long had Bob known? "I've found out late April," Bob said answering the question in Mike's eyes. "I've got many more photographs but these are the best ones." He tapped the pictures. "I assume this is the extent of your wardrobe Michele?" Blushing like his skin was on fire Mike nodded. "Well that will have to improve if you are going to be my secretary, because I expect a professional appearance from my office staff," Bob said with a smile on his face. "Look I'm not disgusted with you or have any plans to blackmail you into doing anything you don't want to do with these photographs, but I am curious about you, so tell me when did you discover that you are really a girl Michele?" Bob sounded sincere and scared about what he might do if he did not answer Mike said floundering with embarrassment, "I.. I don't really know... Its just something I've done for as long as I can remember." Until only a minute or so earlier Mike had always believed that he had hidden the 'Cheryl' side of his personality from everyone. He was looking at Bob afraid of what he was going to ask next and knowing that someone else knew about Cheryl made him feel like he was going to explode with shame. "And does that part of you have a name?" Bob asked feeling slightly guilty about how much he was enjoying Mike's fear filled reaction. "Cheryl." "Cheryl, I like that," Bob said with a pleased grin that made Mike feel sick. "Look, don't look like that Cheryl!" Bob said. "Like I said the last thing I want to do blackmail or publicly out you. I just wanted all the cards on the table before we go any further." He produced a bottle of scotch, two glasses from a draw under his desk and said pouring a healthy shot into one before pushing it over the desk, "Here get that down your neck, and calm down will you because I'm not bothered in the least that you're a tranny." Bob chuckled confidently as Mike shakily picked up the glass. "Look Cheryl, like I said I'm not upset or disgusted with your clothing choices or trying to embarrass you. It's just I need someone trustworthy in my office, and after your performance this morning I think you have a lot of potential. You'll be getting well paid to help me out of a tight squeeze in terms of the business, because I can't keep on top of the paperwork, and in return I can give you somewhere you are safe to express your real self to your hearts content." Blushing with shame Mike knocked back the scotch in one, which made Bob wince before he dryly commented. "That was a waste of a twenty five year old Macallan malt whisky." He lifted the bottle. "Another?" Mike nodded red faced as Bob said, "Savour it this time Cheryl, this stuff costs over a fifteen hundred quid a bottle." That jolted Mike from his shame. "Over a a grand and a half for a bottle of joy juice?" "Yep," Bob nodded, pouring himself a measure. "One of my clients in Dubai knows I'm a malt whiskey buff and treated me to a few bottles last Christmas." He took a sip of his drink savouring the deep richly flavoured, sherry barrel matured malt whiskey. "And I only share it with people I like." Seeing that Mike was still shitting himself Bob let him calm down for a few minutes before restating, "Look I'm not going to embarrass you, and I'm certainly not going to be telling anyone else Cheryl, but I did want you to know that I knew, because as I said, I think we might be able to help each other." Feeling the warmth of the fine whisky in his mostly empty stomach Mike took a shuddering breath, and whispered, "How will we do that Dr. Jeffreys?" "I'll explain in a minute, and you can call me Robert if you want, Dr Jeffreys is so formal," Bob said with a smile. "As I said I felt we needed to be honest with each other." Mike sheepishly nodded. Bob looked gave Mike a guilty look and said with a faint blush, "Because you're not the only one with a secret that makes you different." "Different?" Mike asked curiously. "Different in what way Robert?" Mike looked very guilty and said, "My wife traded me in because she found something on my laptop she did not like." "And that was?" Bob felt a shiver of shame course through him as he forced himself to admit, "I spent three years based in Bangkok after I qualified to build enough experience for my PhD. The job was surveying beach side and city sites for hotel developments. Anyway it left me with a rather bisexual taste when it comes the type of women I work best with and porn." He blushed and plunged on. "I got to prefer shemales and transwomen." Mike looked at him shocked. Bob blushed and glanced at Mike before he added, "Before you ask I am not gay, and I don't find men attractive, but I spent three years in Thailand, and for most of those years my secretary cum PA was a Thai ladyboy called Poon. She more than proved to me that the best secretaries on the planet started out as pretty boys, boys who had then been feminised into stunning girls." Mike's brain was going at a hundred miles an hour. Roberts revelation that he was sexually simulated by feminised guys, and preferred a transgender secretary both scared and intrigued him. Taking a breath he nodded, "Okay Robert, and what do you mean by that?" "I... I wanted you to know, um why I'm not bothered that you like dressing up as a girl." Bob felt himself going as red as Mike, "Well its like, you see, when I hired Poon it was not long after she started her transition, and over thirty something months she worked for me I got to see her change from a girlish boy like you, into a stunning girl, and as I watched her change we got be close but strictly platonic friends." Bob shook himself and took another sip of his malt to collect his thoughts before he said. "When I took the moon shots and was editing them on my big screen I saw you at the bottom of the image. At first I just assumed I was seeing the aftermath of cheeky lockdown shag with your girlfriend. It was only when I sectioned the photo on the big screen and blew up the moon shot to frame it between the two buildings that I realised she was you." He blushed brightly again. "Anyway from then on I became a bit of a peeper and kept an eye on your window. I often saw your silhouette dressed behind your curtains but it was rare when you left them open so I did not get lucky again until late one night when I caught you doing a dirty dance too yourself. It must have been after 2am... I knew it was wrong, but I sat there in the dark and watched you get yourself off," He blushed brightly, "And it was the hottest thing I had ever seen in my life, to the point that I was leaking in my pants." Mike went bright red and hung his head in shame. "I tried to get a photograph but the angle and the light were wrong, but my god I wished I had a photo of you doing that, because you looked incredibly sexy, wearing a red basque, stockings and heels!" Bob took a shuddering breath. "Don't worry about anyone else seeing you, my place was the only one with the angle to see into your window, and even with me constantly looking I only saw you on five or six occasions, and every time it was very late at night." Mike felt really embarrassed knowing that Robert had been watching his girl time, and one question burned in his mind. Had Robert got himself off watching him? Mike could not decide if the idea that he had was exciting or revolting.... "Before you ask the question I can see in your face Cheryl," Bob said blushing with shame, "The answer is yes I did have a tug watching you," He gave Mike a very ashamed look, "And to answer the second question, if I employ you no I don't expect you to have sex with me... Well not unless you want to," He shuddered with embarrassment and swallowed the last of his whisky. Mike could see Robert's hand shaking as he reached for the bottle and topped both glasses saying. "Look I don't want to force you into anything, but I will admit to hoping that you'll take the job as Cheryl, not Mike, and dress appropriately as my secretary?" He gave Mike a sheepish smile and added. "Ever since I got back from Thailand I've always dreamed of finding another girl like Poon to be my secretary." "Oh!" Mike blushed. "And you think I could?" "Replace her, yes," Bob said with a hopeful embarrassed look on his face. "But to put your mind at rest in the time she worked for me I never once made a pass at Poon, which I think surprised her. In the almost three years we worked together the only intimate contact we ever had was the night before I left." He half laughed as he spoke. "And then she had to get me a little drunk before I let her give me a good bye blow job, which was amazing by the way, but I don't regret keeping my hands off her. So trust me when I say if you take the job as Cheryl I don't expect to have an office fling with you, well not unless you instigate it. All I ask is at work you do like she did and dress to my taste." It was a lot to take in but Mike felt Bob was being honest with him. "Look I know it can't be much fun being tied to you room Cheryl, and I bet you've dreamed of having a place where you could dress up however you like for as long as you like." Bob blushed again. "I can give you a job where your employer wants you to express yourself as Cheryl, and if you come work for me I'll even throw in a full wardrobe of work clothes that fit you. Until the Covid travel restrictions are lifted I very much doubt I'll need to see any clients here, and if it does happen you don't feel that you look convincing enough to be seen then you can either hide out of the way or take the day off." Mike nodded, and then said, "But what do you get out of it Robert?" "I get loyal secretary who I can trust implicitly, who doesn't object to being." He blushed. "Eye candy wearing the sort of work wear and appearance I want my secretary to have." "And that is?" "Have you ever seen Madmen?" he asked. Mike nodded. "I want a traditional secretary, one who conforms to the appearance and behavioural standards female secretary's followed during in the late 50's and early 1960's before all the women's lib nonsense," Bob said and quickly added, "But you have my promise that I'll not make the kind unwanted advances on your virtue that were prevalent at the time." "It's a lot to think about Robert," Mike said, feeling a fizzle of excitement about having somewhere to indulge Cheryl freely and safely. "Anything else?" Bob wished he'd stop blushing. "Erm yeah if it interests you, I'd like you to see a specialist transgender dressing service for a make over before having some photo's taken with me pretending to be a couple." He shrugged. "You already look pretty convincing and with a professional styling you I think you can help me deflect the women well meaning business colleagues have been trying to set me up with since my divorce. I've just escaped one marriage and I don't want another so I'm hoping that if I have a few photo's of me with a girl they can catch glimpses of on my phone, hopefully they'll quit doing it." Mike nodded gob smacked by the offer and said, "Okay if I can be made to look good enough, I can do that I guess." He blushed as he admitted, "I've wanted to go to one of them for a long time to find out just how convincing I can look." "So long as you let me get some nice photo's of us together you can. Look Cheryl I don't expect you to say yes now, just think about my offer please, and if its something that you'd like to do give me a ring." Riding the bus home perhaps hour later, Mike weighed up Robert's surprising offer. Although he did not know Robert very well, he did like him and felt he was an honest guy before he put the cards on the table. As he mulled over the afternoons revelation he considered Robert from his Cheryl mindset and he had to admit that he was also a very good looking thirty something bloke who was clearly not short of a bob or two. Chillingly as he thought about the conversation Mike realised that even if their relationship was not physical, that Robert termed part of the job specification as being 'eye candy' he knew that his boss would be being using 'Cheryl' as wanking material! As much as it embarrassed him Mike found the concept that Robert was getting off on him as Cheryl was a scarily exciting turn on. As the bus rattled though town his conscience was telling him that if he was a real man he should reject the job offer immediately, but mercenary side of his brain was asking if could he really turn down a 24 grand a year job where he could work as Cheryl for an extended period? All his life he had wished he was a girl, to be free to do girlish things and Robert was willing to let him do just that. When Mike first started cross dressing as a boy he used to get an incredibly sexual rush from it, but as he aged the sexual nature of his dressing had faded. There was still an erotic component, but ninety percent of the time his dressing was driven by a desire to feel comfortable with himself rather than for any heightened masturbatory pleasure. The more he thought about the offer the more it both excited, and frighted him. By the time he was getting back into the 'student ghetto' his heart thumping as he seriously considered the possibilities Robert's offer had opened up. If he said yes he'd never have to worry about getting caught, and he would be free to dress up without being on edge in case one his house mates discovered what he got up to at night. At long last he would be able to find out just how good he could look, and in the process perhaps answer the question that had plagued him since puberty. Mike had struggled throughout his life with his gender identity, would working for Robert finally prove to him that he really should do what he had always wanted and step on to the path which would result in changing his gender? Getting home one of his house mates asked, "What up Micky you look like you've seen a ghost?" "I got letter yesterday morning with a job offer," he said. "And I been thinking about it all day." "Local?" "No," Mike said, hedging his bets. If he was going to be dressing as Cheryl all day every day he would need to find another place to live, because if Robert was serious about paying for a make over and photographs then Mike wanted a real make over. One that would not wash off at the end of the day, where he got his hair done in an undeniably feminine fashion, his eyebrows done, and his nails fitted with real acrylic extensions along with finally getting his ears pierced. "Its business IT and admin, and I need to make up mind whether to take it by Monday, or say no and see if I can start my masters in October." "Take the job I would," his other housemate said belching as Mike made a mug tea. "Wanna come on the piss tonight? We're both off duty tonight, and after a week on the Covid ward I want to get rat arsed while we can, because we're not in until ten tomorrow!" "No thanks, can't afford it and I want to think this through," Mike said before heading up to his room to consider Roberts offer. The more he thought about it the more excited he became about the idea, and it was around ten in the evening when he made his mind up and texted Robert. "Cheryl will take the job!" Just a moment or two later Mikes phone chirped with the Star Trek communicator sound. "It's Robert," Bob said. "I guessed," Mike chuckled apprehensively. "When do you want me to start?" "As soon as you can, and I mean it when I say I promise to respect your boundary's," he said eagerly. "I'm willing to do it Robert, but I want a couple of things," Mike hesitantly said. "Such as?" "When I get the makeover I want a real make over rather than the usual cross dresser wash it off at the end," Mike said in a rush. "I want my hair and brows done properly in an undeniably feminine way, real false nails and my ears piercing, basically the full works so I have to live as Cheryl 24/7." His voice trembled as he added, "In exchange I'll let you pick the style and colour for my hair and nails." "Done," Robert said clearly excitedly. "Two if I'm going for the full fem look I won't be able to live here any more," Mike said committing himself. "No problem I've got loads of room, you can either move in here with me as live in staff, with no strings attached," Robert said feeling his cock engorging. "Or find a flat locally." "Three, if after three months its not working we call it quits," Mike said. "And I can move on." "Agreed," Robert said unzipping his pants and teasing his cock. "Anything else?" "Yes, if we carry on after the first three months I'll want to see a gender specialist." Mike blushed. "Because what I did not tell you earlier is I've struggled with my gender identity all my life and during first year here I seriously considered going to the doctor to find out if I was transgendered." "You already are transgendered Cheryl," Robert said. "The question is whether you are also transsexual, but yes I can arrange that easy enough." "Okay then you got a full time tranny secretary," Mike said. "Do you want to make it formal with an employment contract saying that the job is for a full time transgendered female?" Robert asked his agile mind seeing all kinds of potential opening up if 'Cheryl' was willing to sign a contract saying 'she' was genuinely transgendered. "It's just I have the English translation of the Thai contract that Poon signed," he fibbed. "Where its laid out in black and white that you'd be taking a job where you'll be expected to appear permanently in a feminine role and that all forms of masculine expression by you are contractually forbidden in line with the life test component of a transition program?" Mike felt his small cock shoot up under his nightgown and said with a blush. "Yes. I'd like that." "My god Cheryl, you really are my ideal secretary," Robert said clearly delighted. "I'd love the idea that you'll being contractually obliged to be my trans girl secretary. I'll even get it written so that you have to wear company issued uniform, and I can assure you the uniform policy will forbid the wearing of pants and flat shoes for secretarial staff." "Yes!" Mike blurted out. "I can do that," Robert said. "And more if you wish." "Such as?" Mike asked. "Is your computer on?" Robert asked. "It can be," Mike said. "Good boot it up Cheryl and I'll email you a link," Robert instructed him. Mike shuddered when he saw the chastity cages and heard Robert say, "When I say more, if it appeals to you I'm willing to even as a clause to the contract so you have to do what Poon did, and include the removal of even that demonstration of your genetic gender?" Mike could not help himself when he said, "Which one?" "Take your pick you're wearing it Cheryl," Robert chuckled. "The small one," Mike said blushing. "The nano or the nub Cheryl?" Robert asked enjoying himself as he stroked his cock. "The nub Robert," Mike whispered. "Good girl," he chuckled thinking about having such a key in his possession. "Anything else while I'm here, because I'm going to purchase you the a nub now on express delivery," Mike could hear the excitement in Bobs voice. "Yes lots!" Mike squeaked embarrassed and excited at the same time. "But I can't think straight just now Robert." "Fair enough," Robert said with a laugh, over the sound of his keyboard clicking before he added, "What are you going to tell your house mates?" "I've already told them that I have a short notice job offer which means might I have to move straight away," Mike said feeling like his cock was going to explode. "Perfect. I'll give you my businesses London PO box to divert you mail. You'll need to pop to the post office and do that on Monday morning," Robert said keeping control of the conversation. "I think you should tell your house mates that you're going on a three day company induction this Wednesday and bring your current wardrobe with you so we can decide if any of it other than your leather skirt and LBD is acceptable for your job as my secretarial eye candy. I'll arrange a few outfits for you to wear so we can test the waters for a couple of days and see if we can live and work together, agreed." "Yes," Mike said. "That sounds fine." "Good in that case Miss Brown I shall see you at 7.30 prompt on Wednesday morning at the bus stop at the top of the road." He chuckled delightedly feeling a surge of excitement at the prospect of putting Mike in a chastity cage and keeping him in it. As Bob stroked his cock he was hoping that 'Cheryl' will get so sexually frustrated that 'she'll' become willing to be more than just his secretarial eye candy! Ever since he had sculpted Poon feminine persona he had regretted turning down her often blatant advances, but while he was in Thailand he was wanted his doctorate, and had avoided any long term social ties. One of his biggest regrets was turning down the happy life she would have given him if he had succumbed to her charms, and as he played with his cock he wondered if Cheryl might give him the chance of a second chance at being in a relationship with someone who fitted his vision of a real woman! Bob wished he could have his new 'girl' immediately but he had site visits and meetings with clients Monday and Tuesday, and he did not want to come over as to eager because he knew 'Cheryl' did not have Poon's accepting cultural background when it came to being a ladyboy. Running his thumb teasingly over his precum covered cock head dreaming about how small his 'girl's' cock will become trapped permanently in such a tiny chastity, he said, "You'll need to email me your NI number and bank details for my accountant so I can officially employ you Cheryl. Oh and send your hip, waist and bust measurement at the same time so I can order you a some basic office wear for next week." "I will Robert," Mike said feeling his emotions going from one side to the other. "Great," Bob asked, "I'll pick you up at seven thirty Wednesday, and run you home on Friday evening for 7.30 and the time between you're Cheryl 24/7 agreed?" "Agreed," Mike said with his heart thumping. "Right, anything else?" "Not that I can think of," Mike said. "I'll send you the banking details and my NI number now along with my sizes, which is a twelve by the way." "Good girl, well I think that's covered everything for now I'll see you Wednesday morning then," Bob said with clearly pleased laugh. "I'm so glad you're going to do this Cheryl because I think it will be wonderful for both of us. You'll get to find out if you really are a girl and if you are, I can guarantee your employment throughout your transition however long that might be, and return I get a hundred percent trust worthy secretary who's willing to dress, look and act in line with my tastes. Trust me Cheryl this is going to be brilliant arrangement for both of us." "I hope so," Mike said feeling both apprehensive and excited. "I don't need to hope I know so," Robert said with a grin in his voice as he added. "So for now I'll bid you good night Miss Brown." "Bye Dr Jeffreys," Mike said wondering if Robert had been having a sly wank while they were talking. As that thought occurred he also wondered what his cock looked like, and the idea that Robert had been wanking while they were talking had his own cock twitching on his palm as he stroked himself through his silky panties. Mike felt a shaver of shame when he realised he was curious about Robert's cock. When Robert first admitted that he got off on watching Cheryl, Mike had been largely revolted, but now some twelve hours later the thought of a guy like Robert was getting off watching 'her' thrilled him. It felt like a weirdly perverse vindication of his feminine persona.... Lay in bed a later Mike found it hard to sleep and dozed fitfully as the possibilities of the opportunity Robert was offering excitedly filled his mind. The more he thought about it the more his imagination ran wild filling his mind with images of being contractually obliged to live as Cheryl, and where it could lead! As he dozed fitfully Mike saw himself fully feminised wearing a big white dress on the arm of a tall strong man who lifted his veil, and leaned into kiss him, and in that twilight state of almost sleep it did not feel gay! He felt the man take him in his arms, his strong large hand on his skirted butt and then they were swaying to the music as he whispered sweet nothings in Cheryl's ear. She could almost feel his unshaven chin on 'her' neck as she surrendered in his arms. Then she felt her head tipped up as his lips caressed hers as she looked into Robert's dark eyes. Shocked Mike abruptly woke, and sat up in bed aware of the summer sunlight streaming though his open curtains. His panties and night gown were sticky and clammy, which embarrassed him even more when he realised he had just been having a wet dream about marrying Robert! After a cold shower to calm down, Mike stumbled down to the kitchen still feeling ashamed of waking up in the damp sticky panties and stained nightgown in his bedroom. Feeling disturbed by the conflicting thoughts and emotions that ran through him after such a vivid dream he almost shit himself when his house mate said. "Wotcha! You look like shit man." "I was up half the night thinking about that job offer," Mike said semi honestly making a mug of coffee. "Dude its a real job, take it!" he said sending cornflakes flying from his mouth. "I would for 24 grand a year. So what if you have to move? This place is a fucking shit hole, and other than your masters what you got holding you here? Fuck all that's what, and I'll tell you another thing for sure, you're a fucking mug if you start your masters while this shit is still going on because there's no way in hell we'll have seen the end of Covid by October!" "Think so?" Mike said. "Yeah." His house mate slurped his tea. "Look we had to study epidemiology in my first year and there one subject of discussion at the hospital and its the infection curve. I'm telling you man all the evidence points to this shit being with us for a least another year, because come the winter its going to get bad again." "Sure?" Mike asked. "Yeah, I know so. Maxine off my course wants to go into epidemiology, and has been working with the infectious diseases specialists plotting local data and she said their consensus of opinion based on current levels is we'll be lucky if its over before next summer, and that was only if we get a viable vaccine rolled out faster than one's ever been developed before." "That's not what the news said," Mike commented sitting at the table. "Aye well they have to spout party line bullshit, and politicians don't like listening to the science," he grumbled. "Look Micky if you've been offered a good job take it, because unless they are vaccinating nationally by the new year you might as well as write off next year as well. Hell if I was in your shoes mate with a secure 24K a year job to go to, I'd ask if you could delay your masters until at least autumn 22." He belched and farted loudly. "Ah that's better! Listen you don't want to be anywhere near the university if and when the second and third wave hits. Think about what you were like as a first year man. What were you interested in, birds, booze and shagging right? Next terms fresh undergrads won't be any different, only they'll be way worse than we were because they're going to go fucking crazy after been locked up at home for a couple of months with their parents breathing down their necks! Trust me mate its going to go through the student population like a dose of the shits after a bad curry." Shocked at his brutal assessment Mike nodded. "I hadn't looked it like that, but it results in the same conclusion I came to last night about taking the job. What about my room and rent if I have move in a hurry?" "Your rent is covered until the end of the month, and by then we'll have found someone. I know of a of a couple of medics off my course who're doing their hospital rotations with me looking for places to live that don't have a commute, and are away from first years, I'll mention we have a place going to them." "Okay," Mike said nodding. "Take it as read that I'm going." "Any idea when?" "I'll find out on Wednesday the reason why they need to know on such short notice is they have a three day induction course at the head office and they only hire every two months. If they decide to keep me rather than sending me to Manchester then it could be as soon as Monday week," Mike told him. "You kept this quiet." "Didn't want to count my chickens. Also the interview was online, and I did it while you were at the hospital. When I interviewed they asked if I'd be willing to start straight away if they offered me the post and I said yes, which is the other reason why its a bit of rush, I thought I'd have longer between the offer and induction." "That's fucking sweet Micky. I'll let me mates know your room will be available by the end of the month," he said tossing his bowl in the sink. "Sorry to dash but I'm on duty in casualty on a ten 'til ten." He laughed. "If nout else I'm going to ace my finals in January because I've learned more about being a doctor in the last four months than I have in the last five years." "I don't know why you're worried you've consistently scored a first," Mike said astonished that someone who looked and acted like a Millwall football hooligan was going to have MD after his name in January. After having some breakfast and washing up his house mates dishes, which was something Mike would not miss, he went to do his washing and since he had the house to himself until the evening he did 'Cheryl's' bag as well. Mike did not realise how much work was involved in moving out, because the following days flew past. Telling everyone that he had to be on the 7.55 to London he was waiting at the bus stop a good five minutes before Robert pulled up in his car, and asked as Mike got in. "All sorted Cheryl?" "Yes, thanks," Mike said. "They all think I'm in London until Friday night." "Good because you have a little package waiting at home," Robert said with a delighted grin as he added. "There is a copy of your employment contract in the glove box, I suggest you read it because I want you to sign it straight after as you've changed when we get home," He lightly patted Mike's leg and grinned feeling the suspender tab through his jeans. "Mmm good girl, stockings and suspender belt already." He chuckled. "I think you'll approve of the clauses I have had written in." Mike opened the glove box and removed the envelope. Inside was a photocopy of the contract that said at the top, Employment contract Jeffreys Survey Ltd. Underneath it read, name of employee, Mr Michael James Brown BA, also known as, and hence forth refereed to as Miss Cheryl Jane Brown. Gender. Transgendered female in the process of transition. Position, Personal Secretary to Dr. Robert Jeffrey, CEO and MD of Jeffreys Survey. Reading the document, Mike felt his cock twitching violently when he read Miss Brown understands and undertakes the roll fully aware that the position is for a transitioning female secretary and agrees to abide by the clothing and appearance standards set out for female executive staff in the employee handbook. Mr Jeffreys provides accommodation for his personal secretary located at the place of work, and this accommodation is included as a part of the remuneration package. Outside of the agreed working hours Mr Jeffreys has no call on Miss Browns time unless arranged in advance. The provided housing however is dependent on Miss Brown continuing to maintain her feminine status in line with life test guidelines of her gender transition outside of working hours, including the duration of any national or personal holidays. This contract only becomes binding at the end of a 12 week probationary period by mutual agreement of both parties. Prior to this either party have the right to end Miss Browns employment without explanation or recourse other than those specified in Clause 5. Clause 1. Miss Brown has requested that all items of clothing and behavioural displays that can be considered as masculine be considered as grounds for disciplinary action. Clause 2. Miss Brown undertakes to follow any required programs or treatments arranged by Jeffreys Survey in support of her transition. Clause 3. Mr Jeffreys reserves the right to change any part of the uniform guidelines at his discretion. Clause 4. If full time employment is offered and accepted by mutual consent, before this contract becomes binding, Miss Brown will have changed her legally recognised name and identity to her post transition gender. Miss Brown also consents to the provision that after one year of employment Jeffreys Surveying may extend this contract at their discretion until completion of her gender transition. Clause 5 If Miss Brown decides not to accept any offered position at the end of the probation period she will provide Jeffreys with three weeks notice to arrange for relocation, and will be paid two months salary plus any holiday accrued as severance. The rest of the contract was standard legalise relating to holidays, disciplinary procedure, health cover, payment and benefits, which surprisingly included a pension plan. "Well?" Robert said pulling off the ring road into the area where he lived, "Any changes you wish to make?" "No that looks wonderful Robert," Mike said, in his best Cheryl voice. "Well then if that's settled," he said with a cheerful grin. "We can get the contract signed when we get home and see where things go." "And that is?" Mike asked suddenly realising he was committed. "Well when we get in I'll show you round the house on the way your rooms, where you'll get changed into Cheryl. Once you are dressed and ready we'll sign the employment contract, which will commit you to living as Cheryl for the next three months." Mike nodded. "I'm looking forwards to signing that." "So am I," Bob said to himself as he said out loud. "Also to aid your adoption of a feminine persona and lifestyle I have hired a therapist called Barbara who is herself transgendered. Barbara works with other transgendered women training them in feminine behavioural patterns and advising them on how to look as she is also a trained beautician and hairdresser. Now I've booked and paid for you to have a four hour training session every Monday for the next six weeks with her starting today with a three hour introduction between ten and one." He patted Mike's leg again enjoying the feeling of her girlish underwear. "She believes it's you who made the online booking, and I've asked her for a prosthetic breast fitting, a body wax and a pedicure. After which she will spend the rest of the morning teaching you the basics of using make- up and how to dress in a professional manner." "I don't know what to say," Mike said astonished at how quickly Robert had moved. "Other than thank you." "It's my pleasure, because I'll enjoy the fruits of her teaching. Anyway after she has gone, you'll open your parcel and take care of hopefully the most obvious remaining indication of your gender." He chuckled excitedly. "I will keep one key, and the other will be frozen in a block of ice and kept in the freezer for emergency use only agreed?" "Yes Robert," Mike said feeling his cock stiffening with excitement. "Once that is sorted, I'll take you through my offices filing system, which really needs sorting out and rearranging because its a mess from only getting everything moved from the town last week, and other than usual secretarial tasks, that reorganising that will be your primary task once you start full time. By then it should be mid afternoon when we'll call it a day and spend the rest of the time getting to comfortable with each other while taking a few test shots so we know what works best for after you have had your long term makeover." "The working day will be 9am until 4pm, and your role will be that of a traditional secretary, so looking pretty, typing, filing, dictation, answering the phone, doing your nails and of course fetching my coffee are all part of your job description. How does that sound?" "Wonderful," Mike said fizzing with excitement. "If today, tomorrow and Friday go as well I hope, then I'm kind of hoping you'll be able to move in on Sunday and start on Monday afternoon." He chuckled. "Since you'll be spending the morning with Barbara having your makeover so we can start as we mean to go on, because I am desperately in need of help with all the work I have on." "And you want to goggle me?" Mike said with a sheepish giggle. "Erm yes," Bob said with a blush, "I've been dreaming about having you sat behind the secretarial desk for the last three days." "I don't see that being a problem," Mike said. "If I can arrange a van I could probably move out of the house Saturday?" "That would be even better if you could as it will give us Sunday to get comfortable, and the vans not problem if you can drive?" Robert said. "Because you can borrow my site van, it's not been sign written and is just a plan red transit. How much stuff do you have to move?" "Not much, it's mostly books and my computers. Plus clothing and some family heirlooms," Mike told him as they pulled up outside his house. "Well assuming that," Bob jabbed his thumb towards the back seat. "Is Cheryl's wardrobe, you won't be need any of your other clothing." "Good point," Mike said feeling his heart thumping as he got out of the car. It was happening he was going to be living as Cheryl. "I'll keep it for now. I assume you have somewhere to store it out of the way?" "Sure it can go in the loft or in the garage," Bob said gleefully. "After all once you have signed the contract you'll be contractually forbidden from wearing pants or shoes without heels unless I say so inside and outside of the house." "I'm looking forwards to having to do that," Mike admitted. "So am I!" Bob said with a ripple of excitement in his tone. At last he was going to have his wank fantasy living with him! For a moment they stood there by the front door looking at each other and then Bob unlocked the house and led him in. "I've put you up in the attic rooms. I told you that when I bought this place it had been a dentists?" Mike nodded. "With the practice down here, and then two flats. Although the house is no longer divided the attic is still in effect a small flat with a bedroom, a bathroom and what was the kitchen diner I took out the kitchen and knocked it through to increase the size of the bedroom, but the living area is still there." "We've almost two hours before Barbara is here," Bob said. "I'll show you round and your room, and let you get changed. Then we can have a mug of tea, and sign your contract so you are officially my employee." "Sounds good," Mike said feeling a tremor of apprehension course through him. "When you come down bring your boy clothes with you," Bob said. "And I'll put them in the boot of my car, because from now on you are a the sort of young lady who always wears skirts, dresses, hose and heels Miss Brown." "Yes Dr. Jeffrey," Mike said shivering when he realised this was the moment of truth, could he really dress in front of him knowing that Robert's cock was going to be going wild in his pants when he saw him? "Great!" Bob said holding out his hand. "Welcome to Jeffreys Survey Miss Brown." Mike shook hands and said, "Thank you Dr Jeffreys," feeling very awkward when he noticed that like in his dream Robert had big powerful hands. Hearing Bob going back down the stairs Mike felt a mixture of fearful excitement as he opened his case and removed, a simple calf length 'student girl' skirt, his home made rice filled bra fillers, and a soft pink university girl cut tee shirt. Swallowing dryly he took out his make up and did his face as best he could, before untying his hair and held it back with an Alice band. Slipping his feet into his only pair of three inch heels, Mike gave himself a final spray of Anais-Anais perfume, took a deep breath and slowly walked down the stairs. Feeling scared, embarrassed and turned on Mike found the kitchen and said walking in. "Well?" "Oh my!" Bob gasped. 'She' looked better close up than he could ever have hoped. "You look great Cheryl." 'Cheryl' could not stop her eyes dropping to the front of Bob's pants and saw his reaction from the tell tale tenting of his jeans. Feeling a shiver of shame Mike shocked himself when he found himself again wondering what it looked like? "The contract is on the table," Bob said, dropping two tea bags into the pot. "All it needs is your signature and you're my employee." "As Mike or as Cheryl?" Mike asked, sitting down with his tea. "Both," Bob said trying to contain his excitement as he added. "You smell nice." "Thank you," Mike said with a blush as he signed the contract as Mike Brown on the first page, and then Cheryl Brown twice on the last. "Excellent," Bob said, collecting the documents and slipping them in a folder before he handed them back and said. "Pop them on my desk please Cheryl, while I make us the tea," He chuckled "Although making tea for the boss is your job as my traditional secretary since its your first day I'll treat you this once." "How do you feel?" Bob asked a little later handing Mike a mug of tea when they were sat at the table. "Apprehensive Robert, excited." He blushed. "And more than a little turned on about actually doing this." "Pretty much the same as me then," Bob said. "I've been giving a little thought to your hair and I was thinking a classic structured fringed shoulder length bob. The sort of professional but feminine hairstyle a News reader would wear, and I think I'd like you to be a blond, so if Barbara asks you what you want doing with your hair on Monday you can tell her. I want your nails classic fire engine red, and at least half a centimetre longer, narrow nicely arched eyebrows and double pierced ears, how does that sound?" "Like a fantasy come true," Mike admitted. "You'll have to tell me a few of them sometime," Bob chuckled. "I'll make myself scarce when Barbara arrives. I've got a stack of work to do so don't worry about me, just come to the office with a tea tray when she gone, and I'll show you the filing system. I'll probably still be working but there is already a small stack of work on your desk for my new secretary to be getting on with. If there is anything you don't understand just ask." Bob chatted about his business while trying not to blatantly goggle 'Cheryl.' Sure she did not look anything like as good as Poon did when he employed her, but even with her studentish clothes un-styled hair and rudimentary make up Cheryl would probably pass as one of the hundreds of female undergrads on first glance. Feeling sure that once Barbara worked her magic she would pass more than well enough for a practice photo shoot, and perhaps the experience of seeing herself might even give her the confidence to join him in a short walk down to the post box and back. The thought of her posing for his camera had Bob struggling with his cock. If she looked this good fresh out of the box, how much better was she going to look after Barbara had really gone to town on her the following week... Grinning he thought about the box in his desk draw, and he had to severely restrain himself from having a sly stroke of his cock when he thought about how it would soon be locked on 'Cheryl' as 'she' asked him about his clients. "Internationally, I do a lot of work in the Arab world and they pay the best, but are the most demanding, in the main most of my work in Asia is with the Thai's and Indonesians. In Europe I do a lot of work for the Scandinavians, Dutch and Spanish. Domestically I've worked for pretty much everyone, and I'm well enough known that most of my contracts are arranged on line these days, and in a normal year I'm abroad for a week or so every couple of months, which is why I need a completely trustworthy personal secretary in my office." "Do you think my voice stand up on the phone?" Mike asked. "If you speak like that yes I expect so, why?" Bob said shaking himself out of his fantasy of her under his office desk as he did a deal with the Arabs or having her accompanying him wearing a head scarf if he got another contract in Dubai. "I could always install a modulator through the computer to alter the pitch and use a phone headset," Mike mused. "I'd not bother Cheryl," Bob said. "Your voice is not very deep to begin with and your Welsh border accent works well, I expect once which ever speech therapist Barbara recommends has taught you a few tricks you'll be fine." "I hope so," Mike said sounding worried. "Talking of Barbara, when she arrives you can use the main bathroom, and either of the back bedrooms, one's fitted out and the other is empty just now," Bob wished he could watch her transformation but he knew Cheryl was not ready for that yet and reluctantly changed the subject. "Can you cook?" Bob asked. "It's just I really enjoy cooking, so I was thinking we could just rotate the cooking between us? I usually use the kitchen on the next floor, this one is more for the odd occasions when I have to have clients round for dinner and I get caterers in." "I'm a bit hopeless but I can make something edible," Mike said, "And I would like to get better." He smiled sheepishly. "It's one of those stereotypically feminine things like dressmaking which I've always wanted to learn." "Use Delia Smiths cookery course book," Bob said. "It's how I learned." "I'd like that," Mike said. "As for dressmaking, if it interests you it is a suitably feminine hobby so I've no objection to you learning," Bob said with a smile, as he quietly reinforced her status. "I'd like that as well." As they chatted how thing were going to work Bob could tell that 'Cheryl' was starting to relax and he felt he was starting to get on with this slightly different version of the person he knew. Cheryl was a little more open and seemed more willing to respond to his often patronisingly flirty teasing sense of humour. She had what he felt was a very sexy giggle, and felt a shiver of regret that the conversation had to end when he heard a car pull up outside. "That will be Barbara for you Cheryl," Bob said reluctantly standing. "I'll be in my office if you need anything." Sitting in his office chair, Bob could hear their voices and wished he could watch what was going on but he knew a little discretion at this stage would pay off in the long run and turned his attention to the preliminary site report he had to write. Even with the simmering under current of sexual excitement about having at long last another lady boy in his life, Bob was very disciplined when it came to work and as usual once he started concentrating he forgot about everything else. His concentration was broken after about forty minutes when he heard a yelp of pain and smirked to himself hoping that it was Cheryl discovering the pain of a bikini wax. Bob guessed right, but it was worth it because Mike could not deny how amazing his skin felt as Barbara taught 'her' how to apply her make up. If Bob had not told him he never would have guessed that she was transgendered because on every level she was convincingly feminine. Much to his distress because he felt he was just at the point where he was actually learning something, the three hour session finished with a discussion about his long term make over. "Although its a bit of a T girl stereotype that we all want to be blond, I think you'll actually look great as a blond," Barbara said, when they finalised how he wanted to look after his 'real' makeover the following week. "The eyebrows might be a little tricky but if you're really fixed on having good arches we might have to resort of microblading." "What ever you think is best Barb," Mike said, loving how he looked in the mirror. Much to Mikes surprise the session actually ran over time by about half hour but Barbara did not seem that concerned and after showing her out he finally had time to really take in his reflection, and it transfixed him in front of the hallway mirror for a long few minutes. Barbara had shown him the basics of how to use curlers and setting lotion, when she turned his flat boyish long hair into a mass of curls that bounced as he tip tapped up and down the hall enjoying his reflection wearing a neat grey pencil skirted business suit, a silky pink blouse and matching pink heels. Underneath he was wearing a pink underwear set that looked and felt amazing against his smooth skin as he watched his new silicon false boobs dancing delicately under his blouse supported by the bra around his chest. Being mastectomy prosthetics the breasts were suitable for use with medical grade adhesive, but Barbara advised against it except for special occasions because it was bad for the skin and the breasts. Realising that he was wasting time, Mike walked to the kitchen trying to recall what Barbara had taught him about posture and walking in a feminine manner as he made a tray of tea and carried it into the office. Bob was hunched over his computer typing furiously, and giving 'herself' a smile in the windows reflection 'she' said, "Your tea Doctor Jeffreys." The look on Bob's face was priceless as he gasped, "Fuck me! Wow, Cheryl you look amazing." "I feel it, thank you so much Robert," 'Cheryl' said feeling like 'she' was on top of the world. "What do you think of Cheryl version 1.1?" His jaw went up and down for a moment and then he said, "Stunning!" Mike felt a little embarrassed by the meat market look Bob gave him as he said, "Spin round for me please Cheryl." Unsteadily owing to the extra inch of high heel, Mike slowly turned, and said, "I'm not used to heels this high, but I don't know how to thank you for this." "I do," Bob said with a grin, removing the box from the chastity shop from his desk. "By putting this on and giving me the keys." He smirked and said, "There appears to be something masculine marring the front of your skirt sweetie, and that is grounds for disciplinary action." Mike blushed and said, "It's been doing that since Barb waxed me." "Well it needs to go Cheryl, either you do it or I will," Bob said with a teasing laugh handing over the package. "I locked Poon in one when she had a similar problem, and have no qualms about doing the same to you young lady." Opening the box Mike's hands were shaking as he looked at the small cage, rings and lock. Having measured himself after Robert told him what he had ordered, he removed the correct ring, and set it along with the cage and integral lock on the desk. Feeling like he was no longer in control of his actions he sheepishly blushed and shocked himself by asking Robert. "Do you want to put it on me Robert." He bit his lip knowing that this was well past the boundary he had discussed with himself. "You can if you want?" Bob 's jaw dropped stunned as he looked from the components on his desk into Cheryl's apprehensive eyes. He had made up the comment about Poon, and never expected 'Cheryl' to be willing to let him do that. Collecting his thoughts he said, "I'd love to do that for you Cheryl, if you're very sure you want me to?" Mike bit his lip in an incredibly sexy way to Bob's eyes. "I want you to and-" He blushed brightly, and said, "I... I don't know if I can actually do it to myself. After all you are doing for me... I... I think its right that you should be the one who denies me of the ultimate expression of masculinity?" "Okay Cheryl," Bob said hoping his voice sounded more stable than he felt. "I would be honoured to take away your remaining masculinity." He slowly stood and walked round his desk, saying. "Undo your skirt and lower your panties please." 'Cheryl' was blushing like a traffic light as 'she' obeyed, and Bob loved the play of 'her' bright red nails against the grey of 'her' suit as 'she' reached behind her back and unclipped 'her' skirt and let it slide down 'her' stocking covered legs. Clearly embarrassed she slowly lowered her pink panties revealing her shame shrunken hairless penis, and Bob felt a shiver of self disgust as he wondered what it tasted like.... "Hands behind you back please young lady," he said trying to stifle the surge of excitement that filled him as he picked up the ring and reached for her penis. He risked a glance at her face and saw her eyes clamped shut, which was a relief because his hands were shaking as he slipped the ring round the base of her balls, and aligned the cage with its mounting. As Bob pushed the parts together and slipped the locking mechanism into place he said, "Ask me to lock it please Cheryl." Mike's voice was shaking when he said, "Please lock me Robert... I've never liked the thing." "Good girl, now you do understand that when I turn this key it means you're mine Cheryl, because I won't be taking it off just because you ask me?" "Yes!" Mike gasped, as he felt Robert turn the key and increased tightness over his cock the parts locked into place. Robert almost came in his pants when he felt 'her' jump as he turned the key until it clicked and let him pull it free, relishing the thrill of turning 'her' cock into a small pink resin covered nub. In an unsteady voice Bob said feeling his pants painfully constricting his cock as he hurriedly walked back round his desk before his erection split his zip. "You can get dressed Cheryl it's done." Mike was blushing with embarrassment as he quickly covered himself and said in an unsteady tone, "Thank you Robert." "No thank you doll," Bob said. "That was the hottest thing I have ever done in my life." While Cheryl had been replacing her panties and skirt he had taken the chance to open his fly and release the pressure on his cock, which was now stuck up from his pants like a flag pole. He was itching to give it a sly stroke but kept his hands above his desk as he said in a steadier voice, "Please serve the tea, and take a seat Cheryl." Bob half laughed to cover his excitement and added, "After that I don't think I'll be able to concentrate on work for a while." Mike could feel the alien object on his cock and it felt both wonderful and terrifying as he poured the tea for them both looking for the keys. Other than the box and the three remaining rings the desk was empty, and feeling a shiver of shame he took a seat opposite Robert, who asked, "Is it comfortable?" "Yes," Mike said in a tone that dripped with embarrassment at what he had let another man do to him. "Good. You must tell me if you get any chafing or rubbing," Bob said with a smile. "I have the keys safe, and one will be placed in a half full ice cream tub that I have already frozen when I fill it to the top and put it back in the freezer it secure the key as we agreed. The other will reside with me," He grinned and looked over his desk, "How did it go with Barbara?" Little by little Bob drew 'Cheryl' out and got 'her' talking abut 'her' lesson, which reduced 'her' anxiety and he was able to find out what Barbara thought about his hairstyle suggestion. "She said I'd look good blond, and the style would suit my face Robert." "Good because that is what I want." He chuckled, and after keeping 'her' talking for a good forty minutes he reached for his camera and asked, "Can I take some test shots of you Cheryl?" "If you want," Mike said having at least to a degree relaxed enough to be curious about what sort of photos he wanted. "Go sit at your desk, and start typing up the letters you'll find in your in tray please Cheryl," Bob said standing to reset his camera. "If I call your name look at me and smile." Mike giggled, and said, "I think you better do something up Doctor?" Bob blushed brightly when he remembered his fly was down, thankfully his cock had gone down somewhat, but even so it was a little embarrassing. He hid his embarrassment by getting his David Bailey on, and for the next half hour or so as 'Cheryl' typed up three letters every now and then, Bob would call , "Cheryl," and when he did Mike would look up or round and smile into the lens. At first he felt clumsy and stupid, but as he got used to the camera Mike relaxed and after a couple of dozen shots started to play to the camera. Eventually Robert said, "Do you want to go and change into your leather skirt, and I think I got you a halter neck top, with your black heels, oh and hold your hair with that Alice band again. I think a bit of a casual shot in the garden would be fun and we could both do with some fresh air." Enjoying himself by now Mike went and changed before quickly rejoining Bob who was sat in the garden with a pitcher of Sangria and a small tray of sandwiches. Grinning when 'she' came out of the kitchen Bob said, "You look great Cheryl babe, hold it there," and took a sequence of photographs as she walked to the patio table. "What a great garden," Mike said enjoying the sheltered space. "It was the main reason why I bought the house," Bob said. "I had so many happy times here when I was a boy and later long after the the Thomas's left I'd be visiting grandparents every time I drove by I saw the place getting more and more dilapidated so it seemed like fate when I saw it for sale when my divorce was being finalised." He grinned sheepishly. "Now the borders are over grown it's conveniently private enough that you'll be able to sunbathe in a bikini out here during your transition." "I'll enjoy that," Mike said, "I've always wanted undisguised tan lines." "You just want to be in a situation where you have to be a girl," Bob said snapping photographs, saying things like, "Drop your left shoulder and push your tits out," as he took another adding, "That's it babe, tart for the lens." Oddly because he realised Bob was one lost in the moment treating him like a photo model he really enjoyed the couple of hours in the sun being photographed. When Bob finally put his camera down, and sat beside him at the patio table Mike said with a chuckle. "You've done that before Robert?" "Yeah, don't get me wrong I love my work but photography is my passion," Bob said with a grin. "I even worked semi professionally when I lived in Thailand. Poon set me up photographing Ladyboys who wanted portfolio images for jobs in the entertainment industry," He laughed lightly and added patting Mikes hand, "Sorry I got a little carried away there." "Don't be its was fun," Mike said sipping his sangria. "But I thought you wanted couple photographs?" "I do," Bob said, "and have got a couple since I sat down." He held up a black key-fob, "Its a remote." "Posh camera?" Mike asked. "It was when it was new, but these days you'd pick one up second hand with a good lens for under two hundred quid. I keep thinking about replacing it, but it takes really good images. The last couple of versions have more features in terms of filters and presets which I don't use because you always get a better result if you start with a good quality raw photograph. If I need to manipulate an image I'd rather do it with photo editing software that I can control rather than the camera," He shrugged, "Also as the sensor in it is still pretty much state of the art, I can't see any reason to replace it just yet." "How's your girl cock doing Cheryl?" Bob asked later that evening. "Is it still comfortable locked away in its cage?" "Surprisingly comfortable unless I get turned on," Mike admitted. "Why?" "Just checking," Bob said blushing. Mike giggled, and admitted, "I half hoped you'd take a photograph of it because I've not seen it yet." He blushed as he carried on, "When I've been to the loo because of how it holds me all I see is a small pink dome when my penis used to be, and I love how it makes me have to sit if I have to pee." "Good!" Bob chuckled. "It's doing its job and giving you no indication both visually and behaviourally you have nothing different to what girls have down there. However if you want to see it, and feel like getting a little risqu? I don't mind shooting some glamour model ones of you after your full makeover?" "Oh god yes please," Mike said enthusiastically after three large glasses of wine. Next morning Bob after masturbating himself silly before he fell asleep, found a very pleasant sight when he followed the scent of fresh coffee from his bedroom to the kitchen, Cheryl was already up and dressed. Although her hair and make up were not quite as good as the previous evening, he was not complaining when he found her in his 'living' kitchen with a pot of coffee wearing an apron she must have brought with her. "Morning Robert," Mike said brightly, blushing when he saw something large and hairy through the gap his pyjamas. "Morning," Bob grunted pretending to be still half asleep as he shuffled forwards praying his cock didn't spring out of his pyjama pants before was able to wrap his tatty towelling robe round himself and hide it. "Coffee?" "Please." After a couple of mouthfuls Bob asked, "What time did you get up this morning?" "Not much earlier than usual, just after six," Mike giggled. "I knew I needed to be up as I felt sure it would take me ages to do my hair and face, and I did not want to be late on my first day." "Any discomfort with your girl cock?" Bob asked, he wanted her willing to talk about her sexuality and decided the best route was to just treat it like a normal subject. "Only when I got stimulated and it tried to be masculine," Mike said with a blush. "Which was pretty much the whole time I was dressing and doing my hair and face." "That's what its supposed to do," Bob chuckled. "It supposed to train you not have them, and aid the transference of your erogenous zones to your breasts once you've started on hormones." Mike blushed, and said, "We'll have to talk about that when I start full time Robert." "Why do you want to start them?" he asked. "I've wanted to start them since the girls in my class started growing boobs," Mike said with a half laugh. "What would you like for breakfast?" "Just coffee, banana and toast," Bob said, astonished that 'Cheryl' was willing to make his breakfast, which was something his ex-wife never did even when they were courting. When 'she' finally joined him at the table Bob joked, "Perhaps I should have employed you as my maid not my secretary?" Mike giggled and said. "I've got the uniform, its what this came from." He pulled the string of his apron. "I worked in a posh hotel in the Lakes as general assistant during the summer of my first year and 'borrowed' one of the chamber maids uniforms from stores, and I kind of forgot give it back for some reason." "I'll look forwards to seeing you in that sometime," Bob said feeling his cock pop out of his pants. "The maid's uniform is a very common tranny fantasy," Mike said sipping his coffee. "Not having anything?" Bob asked. "I had some toast and yogurt before you got up." "I knew I made the right choice," Bob said cheerfully when he came into the office a good half hour after Cheryl had started, and found four of the five letters on his desk awaiting his signature. She had also checked his diary because next to the telephone was the file for the project he was due to call a client about at 10.30. "Good morning Dr Jeffreys," Mike said cheerfully. "The information for your ten thirty is on your desk, and," as he spoke the printer spit out the final letter. "This is the final letter you put in my tray sir." "Proper little secretary aren't you." He laughed taking the letter. "Thank you." "I want to be Doctor," Mike said feeling deliriously happy. "You don't need to be so formal you know," Bob said feeling his recently drained cock saying hello again! Mike giggled in a manner that he never would have shown a week earlier. "I want to keep things professional in the office Doctor, that way there is a clear division between what is business between us and what is pleasure, well social." "Oh so you take pleasure from my presence do you young lady?" Bob said with a tease in his tone. "Good, because I'm taking a hell of a lot of pleasure from you already." Mike blushed and nodded, recalling the glimpse in Roberts pants. "Umm. Yes." "Good girl!" Bob said with a laugh, as sat behind his desk and quickly scanned the letters before scribbling his signature on each. "Can you envelope and address these please Cheryl." "Certainly Doctor," Mike said standing and tip tapping to Roberts desk and picking up the letters. Where Mike was dressed professionally in a dark blue skirt suit, and heels with his hair and face done, Bob was wearing at best business casual, a pair of jeans, sandals, and a cotton traders checked shirt with tie loose at the neck. Given the distraction of having his ideal secretarial support Bob was amazed to find out that it was an incredibly productive day, and for the first time in a long time he was able to call time on his working day without increasing the backlog of paperwork and had even managed to catch up on some it. "Well Cheryl," he said when she fetched him a pot of tea, "I know one thing for sure, for someone who did not claim to be a skilled secretary you have turned out to be better at the job than any of the expensive agency staff I was hiring." He sat back in his chair and carried on. "Today is the first time I've managed to catch up on work rather than increasing the backlog since before lockdown started. Carry on like that sugar, and I'll have to give you a pay rise when your probation is over." He waved at the seat in front of his desk. "Have a seat, I think we can call it a day." "Thank you," Mike said, "I know I'm a little slow with finding my way round your filing system, but I think I'm seeing how you organise things now. I did mean to work my way through the cabinets first thing, but I prioritised your correspondence. The I saw how disorganised my computer was, because I could not see any logic in how things like fixed format letters were organised so I tided that up, and also spent a little time redoing the formatting of your letterhead and footers. All the excess tagging and boxes offended my sensibilities so I sorted them out. They don't look any different but they'll print better, use less toner which means they'll be quicker." He smiled sheepishly. "Hope you don't mind?" "Mind lord no, that's precisely why I employed you, but don't break your back over it, because we're not going to get caught up over night," Bob said, asking, "The main thing is did you have fun today?" "Oh god yes Robert," Mike gushed, "It's been like a dream come true to be working as Cheryl, and when you were doing your video conference and asked me to get you that other file in such an off hand way, was a rush," He giggled, "It was painful, but a rush." "Your girl cock trying to be boyish was it," Bob chuckled. "Cheryl?" "Yes," Mike said sheepishly. "Robert." "Robert now is it?" He laughed. "Well you said the working day was over," Mike answered with a tease in his tone. "So I did," Bob said with a nod and asked, "Do you still want me to take some glamour shots of you?" "Oh god yes!" Mike said. "What do you want to wear?" "My red basque, stockings and heels t begin with," Mike said with a blush. "Since you didn't get a photo last time?" Bob looked at Cheryl grinning at him and said feeling his cock pop the zip on his fly. "T.. That would be perfect." She grinned and said cheekily, "Something bothering you Robert?" "Yes, and you bloody well know what sweetlips!" Mike giggled. "Have you any suggestions for the photo's?" "Lot's if the weather is good I want to do a few bikini, and swimsuit shots in the garden. I'd also love to recreate that iconic girl playing tennis poster oh and I love to photograph you in a tight laced corset," Bob said. "That's a bit of an urban legend the whole tight lacing thing," Cheryl said. "I'm reading a book on Victorian fashion history and about the only time you got someone tight laced was very rich women on very special occasions such as debutante balls. If you tight laced someone they could not work and they were a lot more active than we are today because they did not have modern conveniences, like Hoovers and washing machines, or supermarkets." She giggled lightly, "Women prior to the invention of the modern bra wore corsets to support their breasts and give shape and support to their clothes. I love to wear one though." "I'm sure you will Cheryl," Bob said, "once you're transitioning and have something to support." "Oh I hope so!" She laughed. "What do you want to do for dinner?" Cheryl asked sometime later as 'she' collected the tea tray. "I'll knock something together," Bob said, "I'm in the mood to cook. What do you fancy?" "What ever you want to make," Cheryl said carrying the cups into the kitchen. Knowing that he was pushing the boat out Bob picked up the letters and asked, "How brave are you feeling Cheryl?" "To do what?" Mike said resurfacing from Cheryl. "Nothing silly just walking with me to the post box at the top of the road and back?" He chuckled. "You look great and walk really well in your black heels. This time of day most of the neighbours will be still at work, so its an ideal time to take your first walk in public?" "I don't know?" "Trust me Cheryl," Bob said encouragingly. "Isn't it better to jump in feet first, and its probably only 800 yards round trip?" He grinned and added. "Also I really like the idea of it." Bob knew he had won when he saw Mike fade in Cheryl's eyes as she nodded. "If you think I can." "I know you can," he said. "And I want to see you tip tapping along beside me with a handbag over your shoulder." It was strange Bob noted to himself as he walked protectively beside Cheryl to the top of the road and back. He was starting to be able to differentiate between when 'Mike' was driving Cheryl's personality and she when she was letting 'her' more naturally feminine personality dominate. The core personality was the same but there was a massive difference in each side of her expressed herself. The longer the day had gone on the more he had been able to tell when 'Cheryl' rather than 'Mike' had dominated was dominating. Grinning to himself as they walked back to the house he realised that for all Mike would vociferously deny it he felt sure that Cheryl was interested in him, which opened all sorts of possibilities for the future. Warning himself not push to hard, Bob just enjoyed 'Cheryl's' presence, and felt a surge of delight in her reluctance to change back into Mike the following evening. "Well, how did it go?" Mike's housemate said when he got home with his empty Cheryl case. "Great, real good," Mike said feeling uncomfortable as himself after three days of life as Cheryl. "I'm starting on Monday though." "Bugger you won't get a farewell piss up," his other housemate said. "Coz we're both on nights from tonight." "When do you start?" Mike asked. "Tonight, you're luck you caught me as I'm going in about ten minutes, as I'm on 9 'till 9, which is real fucker on casualty." "It's okay, I've sorted out a hire van for weekend so I'll pack this evening, and then get the van first thing and get away early," Mike said. "You don't have to?" "You'll both be fucked up in the morning, and I don't want to be banging round when you're trying to sleep if I pull my finger out tonight I can be on my way before you get back from the hospital tomorrow," Mike said shrugging. "I don't mind as it will give me more time time to settle in and find my feet." "What do you want to do about the bond?" "Its only a hundred quid, call it my share of the bills due," Mike said. "I've already told the estate agent, so you needn't worry. You shouldn't get any post as I stuck a divert on at the post office, and been to the bank and told the college." "Cool! Well look after yourself Micky and we'll see when you back for your masters, because were here for at least another two after we graduate as we've both got our residency at the hospital." Thirty minutes later Mike had the house to himself and pulling out his phone he called Robert. "Any chance of the van tonight?" "Erm yeah I've not had a drink yet," Bob said. "Why?" Explaining that his housemates were working nights and he was packing as they spoke, Robert told him, "Finish getting packed Cheryl, and I'll catch a taxi in to town and pick up the van and be at yours for about 10." Rubbing his hands together with glee Bob, put the wine bottle back in the fridge and called for a taxi. Carrying a bag containing an outfit for Cheryl, and her make up he decided to push the boat out. Wearing a flat cap and overalls, Bob walked Mike house forty minutes early and knocked on the door. "Hi Robert, come in," Mike said. "You're early." "Roads were quiet," he said pleased to note, that when Mike/Cheryl said she did not have much she had been telling the truth because other than five boxes of books, and a mass of computer equipment stacked by the door the rest including his clothes consisted of just a case, a rucksack and a box. "Here, why don't you slip into these and fix your face a little?" He chuckled. "They'll be no one around this time of night, and its pretty androgynous." Mike blushed and nodded. "Okay." "Anything personal in these Cheryl?" Robert asked as he lifted rucksack and case to carry to the van. "Just Mikes clothing." "Do you still want to keep them?" Bob said. "No," Mike said making up his mind. "Can we go via the recycle bin at Sainsburys?" He blushed. "I'm going to be Cheryl from now on." "Sure?" Robert asked as she went to get changed. "Yes." "Good girl." He laughed. The End - Perhaps... Trish 2020.