A New Secretary- A Change In Robbie's Status. free porn video

A New Secretary A Change In Robbie's Status. By Trish Edited by Robyn Hoode When I met Alan through my mum I was just getting over splitting up with Alex. He was offered a post-graduate course at University College London and we split on good terms. I had known from the moment we started seeing each other that he wanted to pursue an academic career, and would be moving away once he graduated. It was annoying but I sure as hell had no claim on him and I guess with hindsight we were really more like friends with benefits than a couple with a future. I helped him perfect Sandra, his feminine alter ego, and he introduced me to Manchester's amazing transgender nightlife. I've always liked transvestites. I guess being a girl who never felt completely comfortable about being a female, it is not surprising that I gravitated towards men who felt the same. When I was younger I thought I might be a lesbian because I was attracted to how girls looked, but after going out with a girl I quickly realised that for all I find the feminine form attractive, sexually they do nothing for me. For a lot of my teens I thought I was just weird, and then not long after I left school I read a magazine interview with a cross-dresser and so much of what he/she said chimed with me. The idea that some men actually felt like I did hit me like a bombshell. Only a few weeks after reading that eye-opening interview I was offered my first job in the admin department of a car rental agency based in Manchester. The job was not the one wanted as I had actually applied for a one of the mechanics apprenticeships on offer, but once again my gender kicked me in the face when they offered me an office job! I was tempted to turn it down because I wanted to be a mechanic, I liked tinkering with engines and had been messing around on motorbikes up on the moors since I was about eleven. However jobs in the north were scarce, and I wanted to get away from home because I knew there was no future for me if I stayed in the decaying former milling and mining town where I was born. There were lots of good reasons for me taking the job, but even so the thought of moving to a huge metropolis like Manchester as an eighteen year old was more than a bit scary. I might come over as bossy and self- confident but being honest that was all just a front, and the day I left home I was more than a bit apprehensive about what I was getting myself into. My fears were somewhat alleviated, by anticipation because the magazine interview mentioned an active tranny scene in the gay village. I think it was excitement about discovering that scene which more than anything else that quelled my anxiety enough to actually make the move. At first Manchester was just incomprehensible, but my job was fairly easy and after a few weeks I started to settle and find my feet. I had been there for perhaps a month before I ventured into the Canal Street area at the heart of the Gay village, and that was where I met Alex, a cross dressing first year student at the University. He was my first real boyfriend and within months of meeting we started living together. The two years we spent together were some of the happiest of my life, in Alex I had someone who was all man where it mattered in the bedroom while also being the kind of girlfriend who liked to dress up for me. He was the best of both worlds, I had all the advantages of a female partner without any of the bitchy moodiness that came with being in a relationship with a genetic girl. Unfortunately our relationship was never destined to last because Alex was very ambitious when it came to his dream of becoming an Astronomer, and right from the start he never hid from me that his academic career came first. I was getting over Alex moving down to London when my mum introduced me to Alan. Alan was working in the same place she was, and one lunch break she mentioned that I was into motorcycle racing. We met a couple of weeks later when one of my motorcyclist friends had to drop out of a trip to the Manx GP, and he offered to take the ferry ticket. I thought he was nice bloke, who was just as bike obsessed as I was, and we kind of fell into a relationship, which made my mum very happy. Alan was a nice enough bloke, but he was a bloke. There was no feminine side to Alan, and I missed the girlfriend aspects of my relationship with Alex. I guess I was to a degree on the rebound and wanted something different in my life which is perhaps why I started seeing him in the first place. Mostly we got on and the only thing we really did not see eye to eye on was some of his bike club mates. I've never been a fan of the biker lifestyle thing, I loved riding bikes but being in a motorcycle club and the getting drunk in a field at a rally side of motorcycling was never my thing. I was into watching racing, doing track days on my super sports bike and endurance navigation events on my road bike, while Alan was very much into the whole biker lifestyle scene. I guess Alan and I had been kicking along together for about six months when my mum was diagnosed with incurable cancer, and more for her than my own wishes, Alan and I decided to get married. I knew it was a mistake, but with the way my mum was going down hill I felt like I had to give her the thing she had always wanted, which was seeing me walk up the aisle. At first things were great between Alan and me, but after a couple of years two of his mates started prospecting for a local outlaw club and little by little over the following year or two they started to draw him into that circle. At first what with us always having had slightly different motorcycling tastes, I did not realise just how close Alan was getting to the club, and only started to get really uncomfortable about it when they he started to regularly attend club parties and runs. Now I did not like the club to begin with, but for Alan's sake I went to one of their parties with him, and quickly left when someone started snorting coke in front of me. Alan however was completely bewitched by the whole thing and when they asked him to 'prospect' for the club it resulted in me giving him an ultimatum, me or them, and he choose the club! Unknown to me Alan had taken a loan out on our house to pay for his new bike, and a rather large amount of cocaine. I knew about the bike but did not know about the drugs and wondered why he made no claim on the house when we got divorced. It was not a nice divorce. The house aside Alan challenged everything, and basically tried to hang the failure of our six-year marriage on me. Lots of harsh words were spoken and because of the people he was hanging round with there were more than a few threats made. Eventually though I won the divorce but it resulted in me being over a 100k in debt when it was finally settled. The house covered most of it but I was forced to sell my track bike and my camper van to pay everything off. After getting financially straight, I needed to get away from the north-west, and through an old school friend got offered an admin job at a chandeliers yard in Dorset. Emotionally I was a mess at this point. My confidence was shot from what Alan had said about me, and I had very little trust in people or myself. After working for almost fifteen years I had next to nothing, but at least I had a job. Sure it was not very well paid, but it was far enough away from Alan and the world he was in to start putting my life back together. Over the years I had become a little more feminine at least in terms of my work appearance, and the first thing I changed after the divorce was my hair as I got it seriously cut, and basically rejected anything that could be considered as stereotypically feminine. I had been down in Dorset for a couple of a years when I saw an advert for an admin-secretary with IT experience from a local IT company. At that point in early 2000 the internet and 'IT' was just starting to become mainstream in business and I knew it was the future, but beyond the office packages I used at work I knew nothing about it. Although I lacked any knowledge of the computer contracting business the advert requested, I knew I was a good business administrator, so I sent off my CV and an application letter without much hope of getting a look in. Less that forty-eight hours later the owner Mr Riley phoned me at home and invited me for an interview that afternoon. I had spent all morning working on my bike and said I was not really dressed for an interview, which made him laugh. He had a nice laugh I noticed as he said, "Neither am I," and told me to come anyway. I'll admit from the reputation of Riley's I was expecting some high-tech offices and instead the address took me to an old farm complex, where I found that Riley's E-Tech was a one man band. Simon as Mr Riley asked me to call him reminded me instantly of Alex, there was something about him which reminded me of my first lover. The interview went well but I did not think I was what he was looking for until he surprisingly offered me the job. I did not know what to make of Simon. He clearly had no clue about running a business and yet seemed to somehow keep a lid on everything. He was one of those frighteningly intelligent people who seemed to thrive under pressure, and I was not sure if I was doing the right thing when I accepted, but it turned out to be the best decision of my life. I liked Simon. He was a genuinely nice guy who like me had been shafted by his spouse, and as we got used to working together I think we did each other good. I was able to take the day-to-day paperwork off his hands, and as I found my feet and built up an understanding of the IT business he seemed more than happy to hand over more of the actual management side to me. In the years since I left school I had worked for many bosses and Simon was by far the best I ever had, probably because he never really saw himself as my boss. From the day I started he gave me carte blanch when it came to the day-to-day business administration and once I had the 'office' side of things working like clock work, he would ask if I knew anything about such and such? If I didn't he would explain it, and then let me go. If I made a cock-up he did not scream or shout like many of my former employers, instead he would show me where I went wrong and let me have another go. For the first time in a long time I felt valued, and respected at work. I liked Simon. We were chalk and cheese, but we meshed really well together as a team. God knows why we got on so well, because we should not have done, after all I was a common as muck a mill town brat, and he was public school and Cambridge educated toff. Even so I still never quite knew how he felt about me until I had been with him for about six months. He had been to see his accountant and when he got back he gave me an instant 50% pay rise! He had said if the numbers were good he'd give me a pay rise, but I never in a million years expected him to do that! Simons attitude was I worked just as hard as he did, and deserved a fair cut of the profits. Even though I knew that he really did think I was doing a good job with him, and we had developed a friendly working relationship, it was still a clearly work based friendship. To be honest I think I intimidated him a little, but as we got used to each other during my first year or so things started to change. It was not any one single thing, but it was lots of little things, like in the past I would make the boss coffee when he arrived, Simon made his own and always brought me one. If he felt like a day off then he'd say, "Bugger work tomorrow Robbie, let's have a day off," and I'd still be paid. For me the biggest turning point came at the start of my first winter with him, when one evening just before he gave me my pay rise and it was absolutely pissing down. As I only had my bike at the time he told me I was daft riding home in the wet weather and said, tossing me the keys to his Aston Martin, "Take the car." At the time he knew the only car I had ever driven in my life was my old VW camper van back when I used to go on track days, and he just threw me the keys to his seventy grand Aston without a blink of an eye. Over the next year or so I found myself to all intents and purposes managing the business. There were times when it was almost like Simon worked for me not vice versa, and the only 'management' he was doing was the actual face to face dealings with clients and contractors when negotiating contracts. That changed when he took me with him to a big computer industry show and conference, since I had nothing formal to wear, he gave me the company credit card and his car keys the week before the event and told me, "You'll need something professional to look the part Rob, take the car into town and find a couple of outfits you like, something that will do for the show, conference and formal." "I'm not buying a bloody dress!" I said. "I'm not asking you to, just get yourself a couple of business suits for the show and something formal for the industry dinner." He laughed. "Get what you feel comfortable with." I looked in the women's wear places and could not find anything I liked that both fitted and did not make me look like a bad tranny, so I bought a couple of men's suits that fit me, which was not hard since I'm not really particularly femininely shaped, and a dinner suit. Simons only comment was, "You look better dressed like than I do." By this point we had become close enough to tease each other, and a few months later he made a crack about getting me a skirt suit, and I said only if you want to end up wearing it. For a moment there was a very odd look on his face but, then he laughed, and made a mocking sexist remark, which I turned round and gave him back. Our relationship had changed a lot since I started because we were no longer really employer and employee, and more like friends who worked together. A good example is during the TT when I insisted he put an internet capable telly in 'my' office so I could listen to the races, and have it there for the World Cup in Japan and Korea later in summer. He got me the telly and then spent the summer taking the piss about the futility of 22 men chasing a pigs bladder. Simon was a very strange bloke. Pretty much every supposed masculine pursuit bored him senseless, and his idea of taking exercise was a long walk with his binoculars and a book of British birds. The show and conference, was a success and we picked up a lot business. By this point I had a good theoretical handle on how the industry worked and after seeing how Simon dealt with potential clients I realised it was just a matter of understanding the language, and I now knew the language. By the end of the week in Birmingham I found myself doing a lot of the talking to clients, while Simon took care of the potential contractors and over the next six or eight months I came to really enjoy becoming the management face of the business. A year later, I was doing most of the contract negotiations both for the staffing agency and the systems programming business, freeing up Simon to do what he really loved, which was programming and developing systems that fitted the criteria of the specs I negotiated. Now Simon might be a genius with a computer but he can not drive for a toffee. If he could reverse into or bump into something he did, so his Aston was regularly in the dealers getting repaired. It was mid December during my second winter working for him and the weather was foul, unfortunately his car, which by now I often borrowed when the weather was bad was once again in the dealers getting its rear lights and bumper replaced. Looking at the horizontal rain he suggested that with the wet weather rather than riding home if might be best if I stayed over. We had spent evenings together in the past but they had been at computer shows and conferences. Staying over at his house was very different, but I had come to trust him so I stayed over. Much to my amazement, he made in the space of about forty-five minutes one of the best meals I've ever eaten and then complained that he was sorry he could not offer me anything better but he had nothing in the fridge! "If that's what you consider a bad meal," I said after I cleared my plate, "Then I can't wait to try something you consider a good meal because that was bloody lovely." He was like a dog with tails when I said that, and chuckled, "If that impresses you Robbie, then you're very easily pleased, but thank you for the compliment." He was not lying about that first meal being a poor one by his standards, because the next time the weather caught me out, he made a beef casserole that blew my mind. I'd never tasted anything like it, and joked, "One day you'll make someone a smashing wife Simon." I was not quite joking, because over the twenty odd months I had worked for him I had started to suspect that Simon was just like Alex. Just weeks after I started I had noticed a pair of tights in his washing basket, and then last year when I was covered in dust from putting up some extra shelves I was cleaning my hands in the kitchen and noticed a bra in the washing machine. I never said anything about my suspicions but it did play on my mind. I guess that night was the turning point, because from then on our relationship shifted from being just work colleagues to being friends, and I often stayed over whenever the weather was horrendous. The first major client I hooked on my own was at that the next computer show we attended, or rather I did since Simon was at home full of the flu with his mobile on hand if I needed to ask anything. At the previous show Simon had been the main name in the business but this time it was me, and I met Lady Hamilton and her PA Diane from the Wilton Estate who wanted an integrated retail system that worked across all the estate outlets. I demonstrated one of Simon's basic retail systems and explained how it was easy to customise for both commercial and retail, and they liked what they saw, or rather Diane did, since she was clearly the IT brain. Lady Hamilton, or Lady Maud as she told me to call her, took a shine to me, and arranged for me to visit Wilton Hall so Diane could show me what they had, and explain what they wanted. Simon was delighted. He had been trying to get a contract out of the Wilton Estate for ages and told me to go and see them. Running through the notes I had taken at the show, he sneezed and coughed his way though reams of advice and pointers, and from his sick-bed took the basis specifications from my notes and whipped up a demonstration package that I could show them. The following week I drove over to Wilton Hall in the Aston, and came home with a contract. I liked Lady Maud even though she was almost the stereotypical aristocrat. I guess I felt an immediate kinship with her because she was also a woman who was built like a brick shit house. There was one big difference between us though, because for all her body was similar in size to mine, Lady Maud was clearly not afraid of her femininity because she was pregnant. Practically her first words to me when Diane let me into her office were, "I say, Roberta, I meant to ask at that show. Were you an oars woman when you were a young gal?" I did not understand the question, but said I was not. "You surprise me dear, you've fine a pair of shoulders, not much on the chest and your physique is perfect, I'm surprised no one spotted your astounding potential, because today I'm sure that any university sports club would have pushed you into the arms of the rowing club." I decided not to mention that I'd never set foot inside a university, and chuckled, "Unfortunately not Lady Maud, my thing was always racing motorcycles." "I say that's rather jolly always wanted to ride one myself but never quite got round to it. Diane's just fetching the tea and then we can get down to business." She smiled at me and added, "I don't suppose you ride out do you? Although it's not as much fun as the old days when we hunted foxes, we moved over to a drag hunt last year, and we're always looking for new riders to join the Sunday hunt." "I would not know one end of a horse from another Milady." I laughed. "I just know enough that if I see one on the bike, I slow down and go past keeping as far from the animal as I can." It was the start of a very profitable relationship with the Estate, and I got very comfortable with both Lady Maud and her PA, Diane. A girl who I seriously suspected might well have been trans, but that could just been me reading into a girl that I found attractive what I wanted to see. She knew her onions as well, because when I was discussing the hardware upgrades, she was asking me questions I did not understand and had to resort to phoning Simon and getting him to speak to her. "I'm from an office admin-secretary background," I joked to Lady Maud. "Who fell into the IT business by accident, so I take care of the business management, and leave the technology to Simon, who I serious think dreams in computer code." She laughed, and looked at Diane saying, "I know the feeling dear." If Lady Maud and her husband Sir Gregory had not been such a well know couple. Who were often cited as having an unusually good marriage for people of their background I might have suspected that there some something going on between Lady Maud and her PA. I felt sure from the way her Ladyship looked at me that she had a liking for her own sex, but again that could have been me colouring her with my own experiences. Over the next few months once the beta version of the package Simon created for them was running in parallel with their old system I went up to Wilton Hall every couple of weeks. I probably could have done most of it on the phone, but given the size of the contract, and its value I felt it important always to meet face to face. I had been up at the hall the weekend of my birthday for the final sign off the system. In reality I could have sorted it out in half an hour with Diane, but I was there most of the morning because Lady Maud wanted to show off her two-week old twins. I liked Lady Maud and enjoyed her company so I did not mind spending the time with her, but I did want to get back to the office as I knew Simon was up to something for my birthday, and not knowing what it was, was driving me a little daft because he had been giving me these silly grins of anticipation all week. When I got back I found out and he shocked me speechless as he handed me some paperwork and told me, "You need to sign them Rob." "Yeah," I said looking at the phone messages, adding, "put the kettle on," as I pulled out my pen. Just before my pen touched the paper he told me that signing them made me a partner in the business. He had a really goofy grin on his face when he flicked me a business card, which said, "Ms. Robbie Willows. Partner & CEO, Riley & Willows E-Tech." "Oh my god!" I gasped, reading the card. "You're serious!" Simon nodded and held out his hand saying. "Yep, 50/50, partner!" I spluttered gobsmacked that he would do such a thing. "Simon you have got a deal." And shook his hand. "Oh yeah and while I remember?" he said with an even bigger grin as he turned towards the kitchen. "There was a delivery for you. I told them to dump it in the garage." "Yeah," I said still looking at the card. "It's probably the stationary I ordered, I'll go and sort it now." Tossing my suit jacket over the back of my desk chair, I loosened my tie and turned towards the garage calling, "Make mine a coffee will you?" Walking down the hallway that led to the garage I wondered how I got from a raggedy arsed lass messing about on motorbikes in the Pennines, to a partner in a business with a seven-figure turn over. Pushing open the door, I hit the light and stopped. Sat in the middle of the floor was a black and chrome Harley Davidson Fat Boy, with the touring pack identical to the one I used as a desktop image on my PC! "OH MY GOD!" I shouted. "SIMON YOU BASTARD!" He had got me my dream bike! Ever since I saw Arnie in Terminator 2 riding one I had dreamed of owning one. I did not hear Simon come in behind me until he said. "Happy Birthday Partner," holding a small birthday cake with the keys between a couple of candles. For a moment I just stood there probably looking like a moron as I saw written on the delivery note 'Ms. R Willows -Partner, Riley & Willows E- tech' and then at Simon in astonishment. "Surprise!" he said giggling with mirth as he held the cake under my nose saying, "Make a wish!" I did not manage to blow the candles out first time and then I did it properly and said giving him a kiss on the cheek. "Bastard... Thank you, how?" Simon was chortling like a loony at my astonishment and said, "Well I wanted to get you a company car for a while, and personal thank you from me, and if I bought you a designer dress you'd have hit me." He grinned and told me to try the saddle, adding, "Since I did not want to get punched, and we don't really need another car, I thought I'd get you your dream bike instead, and I hope you like it?" "Like it?" I gasped settling behind the tank and grasping the bars. "I don't know what to say?" "Well the thank you was a good start?" Simon said looking at me with a delighted grin going from ear to ear as he added, "Why don't you take it for a spin?" "In this?" I laughed, pointing at the roof to the sound of the rain drumming on the slates. "And anyway I'm not exactly dressed for it just now am I?" For a moment I communed my new Harley, and then decided to ask the question that had bugged me since I saw that bra. "Simon, can I ask you a personal question?" "Sure," he said. I'm sure I blushed when I said with a knowing smile, "When are you going to show me what you look like in one of your pretty outfits Simon? Coz I'm sure you're going to look cute!" His face went through every colour before he croaked, "What?" There was a look of disbelief on his face as he stammered, "You know?" "That you are a tranny?" I said with a smile. "Yes." "How?" "Well when I was younger, before I met the wanker my first real boyfriend was a tranny. He was a student," I told him with a grin. "We lived together for about two-years before he left Manchester for UCL." "Oh!" "Anyway I suspected that you might also be a dresser not long after I started. I noticed that there would occasionally be a pair of tights in your washing basket. Then about a year or so back I saw a bra in your washing machine," I said with a calm relaxed smile. "Which is not good for them by the way. Now I might not be Sherlock Holmes, but even I can put that together, especially combined with the fact that for all you're a successful businessman you've actually got a very submissive personality." He was looking at me in shock. "And when I first met you, you really reminded me of Alex, and after I'd worked for you for a few months I realised you were like the boy side of a lot of the T-girls I knew in Manchester." "Oh!" He looked at me in shock and said in a tone thick with embarrassment, "Why didn't you say anything?" "It's not a big deal!" I chortled unable to stop myself giving him a leering look. "I've been wanting to ask you for ages, but never dared?" "And you want me to?" "Wear one of your outfits, yes and-" I said, grinning as I looked in his wide slightly glazed eyes. "I've still not forgotten that comment about ordering a short skirted office suit, and you know it's not a bad idea. But," I said feeling a rush of excitement as I realised the potential of our sudden openness. "It will be you wearing it for me doll!" The look on his face warmed the cockles of my heart as I told him, "However for now anything with a skirt will do. Please? I find the thought of you in a dress really appealing." "You do?" "Oh yeah!" I said wondering if I looked like a grinning moron, as I added temptingly, "Oh, go on?" I got a huge almost drug like rush of delight when I read the capitulation in his eyes as he hesitantly said, "Okay? But don't you think I'm a bit...?" "Sick?" I teased, telling him, "No, not in the least sugar lips. I adore T-girls. For me they are the best of both worlds, as much fun to look at and spend time with as a genetic girl but without the bitchy side, and the added benefit of them being a male between their legs in the bedroom, and lets face it. I'm probably as much, if not more of a tranny than you are!" "Oh!" He had a wonderfully deer in the headlamps look on his face as he tried to come to terms with what I said, and I loved his expression when I added. "And the thought of you decorating the bitch seat of this beauty in tight girlie leathers in the future is a one hell of a turn on!" "Turn on?" "Yeah! A turn on babe!" I said giving him a suggestive look. "You clinging on to me looking like my hot tranny biker bird!" All of a sudden I realised that I had completely disengaged my brain before speaking, and had just told him a little fantasy I had about a transgendered version of him riding on the back of my bike as my bird! I was more than a bit worried that I had perhaps taken things to far, and hid my confusion by jumping behind my 'bossy' self-confident front as I said, "Weren't you making me another coffee... Sweetheart." Simon looked at me with what I can only describe as delighted terror as he said more than a little hesitantly, "So you don't think I'm a perv?" "No more than me babe!" I laughed delightedly, and gave his arse a pat, "Which isn't saying much!And I really like the idea of having you spend a day or two as my sexy little tranny secretary taking my dictation on demand!" Oh god I did it again, and let my tongue run wild, but this time there was no hiding the delighted excitement on his face and I gave his arse another pat and a good fondling, as I said, "Now run along like a good girl, and do as you're told." I half wished I was not almost gurgling with glee at the thought of Simon in a short skirted office uniform, "Oh and I don't want to hear any complaint's about me being a sexist pig either sweetheart!" When I finally pulled myself away from my new bike I came into the kitchen exclaiming, "God sweetheart! I don't know what I'm more excited about. The Harley or getting you to admit you enjoy being a babe?" He looked delightfully confused so I added, "Because you've just fulfilled two of my dreams together..." "I have?" "Yeah!" I said feeling myself blushing. "Well I knew you'd dreamed of a Harley Davidson, but me dressing?" he said sounding amazed. "Mmm!" I giggled, seeing the mental image of him looking like a one of the hot biker girls I'd seen at the TT and the Manx. "You my tranny business partner dressing girlie, looking all pretty for me." "But why?" He said. His question tripped me up, and it was a struggle to explain why as I admitted, "Well you see I've always had a thing for cross-dressers. I guess it started when I was a kid. I was never very happy about how girls are expected to wear skirts and look nice to begin with, and that only got worse when puberty arrived. Almost immediately all my friends started obsessing about boys and wanting to look pretty for them and that just turned my stomach." It was not easy for me to admit this, but taking my time I told him about my troubled childhood in terms of my social gender issues. How I hated having to wear a girls school uniform and because I did not find the male form or men in general sexually appealing I thought for a long time that I was a lesbian. It was kind of surreal because as I tried to explain, Simon kept butting in with similar comments but from the other side of the gender divide. Over the pot of coffee I told him all about Alex, and then how Alan got involved with the club and the end of my marriage. It was weird. Normally I really struggle to talk about that time in my life, but now both of us could be truly honest with each other it was like the barrier that concealed my fears and insecurities had evaporated. "I love bikes and being with bikers," I told him. "But its a bloody sexist world. Women fall into two categories. If you're like me with my own bike and a willingness to plant a bloke on the snotter if he gets a little funny then to 99% of bikers you're classed as a bull dyke. The only other choice even if you ride yourself is to be a dolly bird, in which case you're very much a second class citizen, expected to look good and be there to tart it up for your bloke." "Oh, I would have thought you'd liked that though," he said clearly missing my point. "I mean the bull dyke thing..." "I do," I said, "but for all I enjoy looking at a dolly bird, I don't want to go to bed with one unless she got something under her skirt I want to fuck!" I semi chuckled, "I guess that's why the idea of you dressing up girlie for me is such a great prospect." I copped another grope of his arse and added. "So trust me sweetheart, when I tell you that I'd prefer it if you dressed as a girl for me I mean it, and I promise I won't laugh, because you're bound to look better than I ever did in a dress." He looked delicious when I saw in his eyes a willingness to do what I wanted as he said in a strange hopeful tone. "If you want?" "Oh I do!" I exclaimed as my bloody desk phone rang. It was the cue for us to get back to work, and in between my phone calls and doing the expenses sheets I took loads of pleasure from teasing him about how much fun I'll have once he's properly uniformed as my sexy, short skirted secretary! Unusually Simon finished what he was doing a good hour before I had got caught up with my paperwork. I spent far too much time thinking about my new bike and Simon getting pretty for me to really concentrate on work. Seeing him shutting down his computers over the half wall that separated my orderly office from his cluttered computer area I felt giddy with excitement. "Hope you don't mind but I'm staying over after dinner?" I got a real thrill from giving his arse a bosses pat as I added with a chortle in my tone. "I'll finish up in here, go get my dinner on and then dress girlie for me, babe. Please?" Giving me a weird look Simon nodded and said in an embarrassed cum excited tone, "Okay." "Great!" I laughed. "Now shoo, there's a good girl!" I could hear him in the kitchen behind my 'office' as he put what ever he had prepared in the oven, and he was upstairs by the time I got myself a beer from his fridge. I giggled to myself when I saw he guessed I choose to stay over, because there were a dozen tins of Fosters in the fridge, and called as I popped open a can, "Don't be all day, honey!" After finishing my beer I got changed out my monkey suit, got him a glass of wine and another Fosters for me before I made myself comfortable in the lounge. With my feet on the coffee table and a beer in my hand I felt about as comfortable as I could be given I was fizzing with excitement at the idea of having dinner with him en-fem! As I considered the possibilities, I saw the chance to experience with him something I had always dreamed of, the full role reversal, where I could be Robert rather than Roberta... For years I had dreamed of finding another Alex, who had loved calling me Bob, and his husband when we were living together. Would Simon do the same if I asked him, and unlike with Alex, we worked together, so could we maintain the switch both professionally and personally? Simon looked incredibly embarrassed when he came into the lounge perhaps five minutes later, wearing a rather nice blue skirt, rose-coloured blouse and heels. He did not look bad by any means, but he had a worried smile on his painted lips as he whispered, "Well?" I had been looking forward to seeing him dressed since I confirmed my suspicion. Now that he was dressed in front of me, I was suddenly as apprehensive about this evening as he was, and I hoped he could not see how tightly I was grasping my can as I said with a grin, "Not too bad," I gave him a mock stern smile as I added. "But not that good either." "Erm thanks," he stammered looking a little down hearted as I handed him a glass of wine. "I think." "Now don't look like that?" I chuckled. "Because you do show loads of promise." God it was a thrill to feast my eyes on a tranny again as I examined him carefully and said. "Give me a twirl love?" His face changed as he said in a hopeful tone, "Promise?" "Yeah." I laughed, spinning my finger. "Promise." I could see he was still really worried as he slowly turned round and rather smoothly given he was wearing heels, adding as he faced me again, "This feels really weird," and almost tossed back his glass of wine in one gulp. I could tell he was nervous as hell, and said with a glee filled giggle as I patted the sofa beside me, "I wouldn't say weird honey. I say it feels about right, and you do look pretty good already." "I do?" he said sitting like a sack of spuds beside me. I got a whiff of his perfume as he sat, and could not resist having a sniff at his neck as I told him, "Mmm, you smell nice!" I really wanted to kiss him but I restrained myself and told him, "Yeah, you do, you've a nice slim figure to start with. All it needs is just a little girly care and attention. You've head full of thick hair under that crappy wig, which also just needs some girlie TLC and with your face properly made up. I'd bet you'd look smashing." "I would?" "Yeah!" I laughed, letting my tongue run away from me again said, "Once we've got you looking right, and a few months instruction and I'd put money on you passing in public." "Instruction?" He said. "Yeah." I chortled delightedly. "To train you." "Train me?" He looked deliciously confused. "Let's face it," I told him, "you've not really thought much about how much movement is part of appearing feminine have you?" "No," he said throwing back the other half of his glass of wine with a weird look in his face. "Not like that!" I laughed, slapping his skirted thigh. "Looking at you I guess six months or so should be enough to teach you the basics." "That long?" he said with a blush. "Yeah, but for now," I said not really noticing that there was a hint of bossiness in my voice until I was speaking, "I'd settle for seeing you taking nice girlie sips of your wine, and please avoid sitting down like a docker! What you should be doing is smoothing your skirt behind you and sliding gracefully into the seat, not collapsing down like a sack of spuds!" "What like this?" He stood and did as I asked. "Nearly!" I laughed. "But you're not sitting quite right. May I?" God I loved touching him as I repositioned his body into a really girlie sitting position and I was again reminded of Alex as I recalled telling him the same as I briefly sketched out the main differences between male and female body language. I could tell he was relaxing a little when he quipped, "You've thought about this then?" "Just a bit! I had to teach Alex these same things, but outside my fantasies I never in a million years thought I'd be doing it to you." "Oh?" he gasped in an elated tone. "Well are you interested?" I teased. "In what?" "In letting me turn you into my lass," I said buzzing with pleasure. "Now let me see what can I call my girl, Simone? Naw don't like that?" I pulled on my nose as I considered feminine names for him. "It's not girlie enough for someone as pretty as you." I mused about it over a mouthful of beer and said, "Si, Simon? Si Riley?" And then it came to me. "Sarah? Yeah I like that, I'll call you Sarah from now on. What do you think?" "Okay..." he said blushing again. "Cool!" I chortled adding as my tongue again took over, "So you like the idea of becoming Miss Sarah Jane Riley?" I felt sure I had that grinning moronic look on my face again as I said expectantly. "I expect a response please Sarah?" He had a gorgeous looking in his eyes when he said, "Yes Robbie I am interested." "Great!" I laughed rubbing my hands together. "When do you want to start?" I was feeling rather turned on by how the feminine qualities I had seen in him had come out a lot more as he began to get used to being dressed in front of me. "You know I've always dreamed of finding someone who would swap roles!" "How about now?" he said with a sudden look of excitement on his face. I felt ecstatic when he said that, and my tongue ran away with me again as I told him, "One thing though, if you mean it, for the next six months or so I'm the boss and calling the shots." "Okay Robbie," Simon said excitedly. "And at work you'll appear and behave, as if you were my secretary?" I asked hopefully. His grin went from ear to ear as he enthusiastically nodded. "And I think Sarah," I said feeling giddy with excitement, "that you're the sort of girl who dresses to impress her boss." "If that's what you want, I'm game," he said looking at me with undisguised compliance in his face. "Oh I do and more." I laughed giving him a lewd wink. "Because I see a steamy office affair on the cards!" "Affair?" he said, and blushed again. "Yeah, why do think I like copping a feel of your bum doll?" I felt almost high with delight as I added, "I've already said I think you're hot!" "I am?" "Yeah!" I said, pulling him close for a good snogging! "Mmm!" I whispered pleased as I lifted my lips from him. "I love kissing my lass when she's wearing lipstick!" For a moment we sat there in silence. I guess we were both lost in thought about this sudden change in our relationship and for a moment I felt really embarrassed, because I wanted to tell him everything and I was not sure how he was going to react. He obviously sensed something because he looked me in the eyes and said in a very loving tone. "What?" I felt suddenly embarrassed and grinned apprehensively as I decided to jump in feet first and just tell him. "Erm Sarah, you know I mentioned I want to swap roles?" "Yes?" "How far do you want it to go?" I asked in what I hoped was a confident tone. Working for Simon had given me back my self-confidence and a lot more besides, but deep down I was still that girl who got teased as a hulking teen by the cliquey set for being a 'throwback.' "As far as you want?" he said with wide smile. "You're the boss for the next six months?" "I am?" I said feeling a rush of blood to my cheeks and suddenly it all came out. "Will you call me as Mr. Willows or Sir at work and either Bob or Robert after hours? Please?" "Sure...." Simon giggled, with a really pretty blush on his face as he said, "Bob?" I felt a surge of confidence as I said with a laugh, "Well then! What are you making for my tea then Sarah?" "Erm, your favourite lamb neck chops and mash," he said radiating delight at being my girl! "Chops are always fine by me." I laughed, and added, "And I'll have another beer while I'm waiting darling." Simon's embarrassment had fled as he said in a deliriously happy tone of voice, "Oh yes Bob!" 'Bob' it sounded so natural to hear him call me it, and I could not resist scolding him as he jumped to his feet. "Glide not stride, please Sarah!" I really enjoyed the next hour or so as I bossily told 'my' Sarah how to move and serve me, and the more masculine I acted the more Simon loved it. As usual when Simon cooked, my birthday dinner was delicious, and he really loved playing the little woman for me. We both probably had a little bit too much to drink, but that actually helped because I was able to push my reticence to one side, and even got him to strip in front of me, so I could see just what 'we' had to work with and he had a lot. In terms of his basic shape he was actually starting from a better place than Alex, because Simon was within female norms height wise, and his nerd life meant he was very slender with very little in the way of muscle. He needed his hair, and eyebrows sorting, but he looked pretty good, and I really liked the idea of him with a few earrings and maybe more. Thankfully I managed to get my tongue back under control before I blabbed about pierced tongues and how I loved how the Asian lasses at home had a stud in the side of their noses. I don't know why I felt that was attractive but I got Alex to get one and I really liked the idea of seeing Simon with one as well. "Next timeh" I teased as he redressed, "you'll have practised, because I'm going to get you a couple of lap dancing DVD's so you can really tart it for me when you're losing your clothes for me love." I clearly hit a nerve there because he gasped, "Would you? I'd love to be able to dirty dance like that." Redressed 'Sarah' cuddled up beside me and it felt great as he nestled in under my arm, which prompted me to ask how long Simon had been dressing, which led us into talking about our life histories. It was strange because even more than with Alex so much of what Simon told me echoed my experiences, only he wanted all the girlie shit I loathed. Yet when he was talking about what he hated about school, and having to be a boy, it was pretty much everything I wanted at the same age. Sipping my beer and feeling very mellow, I told him, "I hated being female from the moment I found out that I was one, and thought I should have been born a boy. It's been with me for as long as I can remember, but I didn't really understand what I was feeling until I started school. Even as a five-year old I can recall not understanding why I could not wear trousers like the other lads, and having to wear a school uniform skirt felt humiliating." "Then as I got older and my body started to sexually mature I saw how much better the boys had it. They did not have to put up the side effects of periods, or with cattiness of school girl comments like I got because I had no tits and was physically bigger than most of the lads, and most of all I envied their freedom from all the feminine shit which was imposed on me." "Somehow Bob," Simon said with a light laugh. "I don't think you bothered too much with the feminine shit?" "Ha!" I chuckled. "You never met my mother!" "Still it's not like a woman in men's clothing is anything unusual," Simon said. "Or likely to trigger the same reactions that I'd get if I went out like this?" "Well true yeah, I guess?" I said. "But it depends on where you go. In Manchester round Canal Street no one would blink an eye." As we chatted he admitted to the sense of shame he always felt about his desire to dress up, and I told him in no uncertain terms to forget that, because I wanted him to be feminine, to have pretty hair and dress super girlie for me. I laughed when I got to the end of my mini rant and added, "Because then I can be equally masculine in return." I guess the beer had got to me a bit because I admitted that I'd love to work out and really masculinise my body, which gave Simon the confidence to admit that he had a similar desire to be feminised. "You help me?" I chuckled. "And I'll see that you do?" "Alright Robert," Simon said with a kiss. "You've got a deal." "God I'm kicking myself Sarah," I admitted. "Why the hell didn't I bring my suspicions about this up ages ago when I first started to suspect you might be a T?" I'll freely admit that I was a bit pissed from eight cans of lager as I gave his lips a long kiss and told him. "I think we're going to have a lot of fun with this new phase in our relationship Sarah." "Me too Bob." Simon grinned at me with his eyes begging for another kiss. I don't recall falling into bed when we finally called it a night, but I awoke at about half seven with the sun light streaming through the window. Rolling out of bed I padded to the loo and then took a peek in Simons bedroom. He looked so cute sound asleep that I crept downstairs and made us a pot of coffee, before returning to his bedroom and enjoyed watching him wake up. "Morning Sarah." I laughed giving him a kiss as he sleepily looked at me. "Wh... what time is it?" Simon sleepily mumbled as he woke up. "Half eight, and time to get up!" I chuckled buzzing with anticipation about getting my new bike out and coming home to see him dressed as Sarah. "You've got a lot to do while I give my new bike a test ride!" After handing him a coffee I had a root though his wardrobe and selected some clothes for him to wear, happily telling him how wonderful it was going to be with him as Sarah. I cheerfully expounded on my dreams of being the 'man' as I chivvied him up. "I'd love to get home to find my dinner waiting, or doing DIY jobs while my missus did her housework..." Simon clearly had a very traditional view of the feminine role, and encouraged by his response we realised that what we both wanted was the kind of relationship that existed between the sexes in the 1950's and early 60's. ?How does that sound?? I asked, after we had been chatting for a while. Simon looked at me with a strange smile on his face as he told me. ?You're a chauvinist Robert, but if that?s what you want me to be for you, a traditional girl,? he said with a lovely expression on his face, ?Then I have to accept your decision.? I could not believe he would say it like that and said breathlessly, ?Oh I do babe. I do!? I saw my ear to ear smile in the dresser mirror as I said, ?Now then while I?m out Sarah I want you to lose the body hair, chest, arms, legs, armpits the lot.? ?Okay Rob..? ?From you Rob?s fine babe,? I said mock sternly. ?But you know I prefer Bob, Sarah.? I really enjoyed telling 'her' what to do before I grabbed my leathers and lid, and walked out to my waiting Harley. Just looking at it gave me a thrill. I could not believe it was actually mine as I got into the saddle. I felt a real buzz of excitement as I put the key in the ignition and pressed the starter. God, it sounded good, and clicking it into first, I called, ?I'll be back around fourish love,? and set out on the ride of my dreams. I did not go that far just a couple of hundred miles, round trip. The first stop was the Harley dealers to book it in for a first service the following weekend, a few accessories, and a few things for 'Sarah.' I might not have been a fan of the biker lifestyle world but I did like the girls fashions, if of course I did not have to wear them. In quick succession I bought him a couple of girlie shirts and a leather mini skirt, before riding into town for a few general items for both of us. I went a little mad buying lingerie and nightwear, and even madder when I splashed out on makeup and a textbook on how to use it for Sarah. Finally I got myself some male clothes before I headed into the closest city for some specialist items. After Simon had gone to get changed the previous afternoon I had looked on the internet for specialist suppliers to the transgender market and found two. It was pretty embarrassing when the girl in the first shop thought I was a male to female trans when I was buying Sarah some breasts, and beard cover foundation. Simon did not suffer from a lot of beard shadow but I felt it was still a good idea to get him some good foundation. Later as I rode to the next place, I took the girls assumption that I was a male transitioning to female as a complement. This time there were no such problems because I was being somewhat embarrassingly fitted with a very fancy cock designed for female to male transsexuals. My god it felt good when I pulled my jeans over my now filled boxers, and had to restrain my desire to swagger out knowing that my jeans contained the lump in the groin area I always felt should be there. I half wondered if 'Sarah' felt the same way the first time she saw herself with her breasts padded out? I was still thinking about that as I rode to my final stop of the day at an alternative lifestyle store where I bought 'Sarah' a 'slave' bangle for his ankle, which I got engraved. The Fatboy's saddlebags were packed when I pointed her front wheel homewards and enjoyed a swift, but not super fast ride home. The Harley was not designed for speed, but comfort and she effortless soaked up the miles as I rode back to 'Sarah's' with a huge grin on my face. My grin only got wider when I got back and found Simon looking pretty as a picture in a cotton sundress that fitted him really well. ?Hey Sarah!? I called walking into the kitchen dropping the Harley?s bag liners on the table and grabbing him into a hug laughing. ?You look pretty enough to eat, and I still cannot believe that you are willing to be my girl.? ?Well I am.? Simon giggled before telling me, ?Now put me down you big oaf before I burn the onions!? ?Okay.? I laughed putting him back down before I flopped into the kitchen chair and said, ?Make us a coffee there's a good girl!? Opening one of the bags I removed a small box, I had bought during my blitzkrieg shopping expedition in town and a packet I had got from Boots the chemists on my way back. Putting them on the table I waited until he finished what ever he was doing with onions on the stove before telling him, ?Since you got me such a lovely and fitting present, the least I could do was get you some pretty things in return. But first?? I could not stop my chuckle of delight as I spoke, revealing the four sleeper earrings in sterile packaging and the sterile needles. ?Well do you want me to begin making you beautiful Sarah babe?? He looked at the needles and earrings apprehensively, as I chuckled. ?I'm going to do your ears just like my mother did mine, with a needle and ice cubes.? I crooked my finger at him and pointed to a spot at my knees saying, ?Come kneel here my girlie. I think I mentioned last night that you were getting your ears pierced?? For a moment I thought he was going to refuse and then he giggled and knelt down. It did not take long, and when the four rings were in his lobes I could see his penis making a lump in his skirt as he said. ?I thought it would hurt.? I chortled and gave his stiffy a stroke saying as I pulled him into a kiss. ?Well I wonder how we?re going to stop that happening Sarah?? Behind Simon/Sarah I could see the clock and giving him a pat on his skirted arse I said, ?I?m going to watch the footie results, the season started today, bring us another coffee in babe?? Simon nodded looking at his ears in the mirror and said, ?Sure Bob.? I was not really watching the results as final score played on the telly, instead I was emptying the saddlebag liners. Simon was not long with my coffee, and when he came in I held up a short-cropped camisole top with, ?Harley girl,? emblazoned on the chest and a little leather miniskirt chuckling. ?Can you see yourself in this Sarah babe?? He had a look of pure glee on his face as he gasped, ?Oh god yes, but I?ll need a little help to get away with that top,? and used his hands to indicate his boobs. ?Give it time babes,? I chuckled. ?But anyway I got you another one with a higher neck line.? I gave his bum a gentle spank. ?For the time being!? ?Now how about this?? I chortled, holding up some of the naughty lingerie I had got him, ?God I don?t think I?ve ever enjoyed shopping as much in my life as I have today. Oh and along with these very sexy undies, some homework.? As I showed him the makeup and the book on makeup techniques. ?I know I went a little mad on the makeup, but you got me my second favourite thing in the world, so I bought you a few little things to improve your appearance.? ?What?? Simon asked looking at me in amazement. ?A pretty ankle bangle and a couple of bracelets, a girls watch and a necklace,? I said with a grin as I showed him a necklace with ?Sarah? cast in silver as the pendant. ?Come here and let me put this on you.? I loved how Simon purred with pleasure I kissed his neck before I fastened the necklace and spun him into my arms for a serious kiss. ?What else?? he asked excitedly when I let him go. ?Not much really, a few bits and bobs for me, and, oh yeah, these!? I laughed opening a box to display the fancy mastectomy prosthetic breasts telling him, ?It was embarrassing as hell when the woman in the shop assumed they were for me. She thought I was a male to female trans and advised me 36c were to small for my frame, but they are top of the range attachable mastectomy breasts and will do just dandy for now.? ?Wow!? Simon whispered. ?You must have spent a fortune!? ?Not really.? I laughed. ?And nowhere near what you spent on me, so shut up and say thank you Sarah.? ?Erm thank you...? I gazed at her in delight. ?Bob.? ?Want to try them?? I teasingly laughed. ?I?ve got the adhesive in here somewhere?? ?Adhesive?? ?Yeah, 48 hour waterproof stuff.? I chuckled as I rotted round in the bag the boobs came from, telling Simon, ?Slip your dress and bra off love, I want to see my bird flashing her tits for me!? Ten minutes later he was wearing them and they looked fantastic as the bobbed about his chest. God they looked good, and I could not resist getting him to stripper walk up and down wearing nothing but his panties, tights, and heels! ?Mmm,? I laughed delightedly. ?You're turning into a hot sexy biker bitch for me Sarah,? as I slipped the gold ankle bangle on him. ?There!? I said happily clicking it shut. ?Now you?re really mine.? ?Thought I already was?? Simon laughed. ?Yeah,? I chortled, ?but that says so.? ?Sorry?? He looked at me very strangely as I told him in a very gleeful tone. ?They are called slave bangles love, and I had that one engraved.? ?What does it say?? Simon asked trying to look at it. ?Bob Willow's Girl!? I told him. ?And best of all... I?ve got they key!? ?KEY!? Simon gasped going red.. ?Yeah!? I told him with a pleased grin. ?It shuts with a lock so you can?t lose it sweetheart!? ?Locked, on me?? he whispered. ?Yup!? I told him. ?And from the look of this?? I gave his decidedly unfeminine panties another sensual caress. ?You like the idea of being marked as mine?? ?Sometimes Robert Willows, you are a kinky bugger!? Simon said, throwing himself in my arms for a kiss. ?Me?? I laughed pulling Simon onto my lap. ?Well I did warn you.? ?Yeah you did,? he said happily cuddled in my arms. Unceremoniously dumping him off my lap with a final kiss, I started to put everything back in the bag liners telling him. ?Get dressed love, because you?re awfully distracting with your tits out like that, and kick-off?s in five minutes?? ?You?d rather watch football than me?? Simon teased as he slipped on one of the new bras, and his original dress. ?Yeah.? I laughed. ?You?ve dinner to finish, and all your new things to put away, here,? I handed him the bags adding. ?Anything that?s obliviously for me Sarah, you can pop in the spare room?? ?Spare room?? Simon said with a silly giggle. ?How about the chest of draws in our bedroom?? ?EH!? For a moment I thought I had misheard him and then he said with a very naughty giggle in his words. ?You don?t think I?m going to let you sleep in the spare room again do you Robert?? ?Erm no?? I said, probably looking at her like a moron with surprised delight on my face. ?Good, because I want my man where he belongs in my bed!? Simon giggled as he carried the bags out. He was gone just under an hour and when he walked back in my eyes almost popped out. He looked amazing. ?Wow! You look... Wow!? I was stunned by just how good he looked with his face made up wearing the leather mini skirt and high-necked Harley top. More to cover my shock and watch his arse under the skirt, I said ?Grab us a beer babes.? I could not believe just how much Simon enjoyed being my girlfriend. Sure we had been work colleagues who had grown into real friends over the last two years, but in the last 30 odd hours everything had changed. Later that evening when Simon was cuddled up on my lap distracting me from watching match of the day he asked. ?Bob?? ?What love?? I said enjoying seeing United getting spanked by newly promoted Sunderland. ?Do you want to move in with me? I know you teased me about being the boss but if you want I'd like make this role swap a permanent thing both here and at work?? That distracted me from the football, and I gasped, ?Seriously?? ?Yeah. I want to be your girl, and have you make me to become the kind of girl you want?? ?Make?? I said trying to get my tongue to work. ?Yes. Make,? Simon said blushing like crazy. ?I want you to be the masculine head of the house in our relationship, and take that traditional gender role.? ?For real?? I gasped. ?Yes, for real,? he said grinning at me. ?Good,? I chuckled, ?because I have another surprise for you, assuming you want to be on the receiving end of it?? I took his hand and pressed it on my groin where I was still wearing my new FtM false cock! The look in Simon's eyes was breathtaking and an hour or so later when I came out his en-suite bathroom, Simons eyes followed the bouncing of my proudly displayed realistic 8? flesh coloured cock! Laughing, ?Surprise,? I crudely mock masturbated my new phallus and then felt myself blushing as I admitted, ?Why should you have all the fun and after all, I do want to be a bloke?? The look on Simons face was indecipherable and I was more than a bit hesitant when I asked, ?Well then wench, how do you like your new boyfriend?? Simon was speechless looked at 'my' cock wide-eyed with astonishment. I could not resist it, I had heard the boys telling me about how great it felt when your girl knelt down before you and said to him, ?Why don?t you come and give him a nice introductory kiss Sarah?? He did too, and I discovered the reason why the things were rated as being the best because as he sucked it, the cock transmitted the sensation onto my clit and it felt bloody brilliant! After we made love for the first time, we were cuddled in a comfortable haze, when 'Sarah' said, ?You weren't the only one shopping 'stud' because I ordered myself one of those work uniforms, you liked.? ?Yes!? thought to myself as I felt 'Sarah' cuddled sleepily beside me. ?This will do me.? The End. Trish 2019.