Dress For Success free porn video

I lost my job and couldn't find another straight away. We realised that we couldn't keep up the mortgage payments and had to put the house up for sale. Fortunately, it sold quickly and we moved into my mother-in- law's house. Did I say FORTUNATELY? I don't think my wife's mother ever really approved of me and was never slow to criticise. However she had a large enough house and had never remarried after my father-in-law died. My wife Helen got a part-time secretarial post, so at least we could contribute something to the household budget. I applied for several jobs, but found nothing suitable. There were a few odd jobs that needed doing in the house and garden, so I sorted these out. The work was well done as far as I could see, but I didn't get much in the way of thanks. My mother-in-law found other things I was expected to do, including cleaning the house. But every so often we would have words. If she couldn't complain about the standard of my work she could have a go at my appearance. "You are developing a paunch. You eat too much and you're not working hard enough to get rid of it. We need to economise and cook smaller meals. I'm going to get you a corset. That will hide your bulging stomach and it will also encourage you to eat less. It will also improve your posture." I didn't think she really would get me a corset, but she must have checked the waist size of my trousers, or else asked my wife about my waist size. Because a few days later she announced that she had acquired a corset for me. "It's second hand - I couldn't afford to have one made specially for you. Helen can help you put it on before she goes off to work tomorrow." I'm not sure that Helen was any keener to share her mother's house than I was. But she knew that it was no use trying to get her mother to change her mind once she had decided upon something. So next morning after my shower she showed me the corset. "Actually, I think it's what they call a waist waspie," she said. It was white, with hook fastenings at the front and lacing at the back. And it had three suspenders each side. "Sometimes the suspenders are removable," said Helen, "but these are sewn on. But it doesn't matter. No one will see them once you've got your trousers on." She loosened the laces and I wrapped the waspie round my waist and engaged the hooks and eyes at the front. Helen started pulling the laces to tighten the fit. "Now breathe in," she said, "Mother tells me that it should be possible to reduce your waist measurement by five inches to start with." By the time she had tightened the laces to her satisfaction and tied them in a bow at the back, the corset was really gripping my waist and stomach. "Well, you certainly look a bit slimmer," laughed Helen. She left me to finish getting dressed as she went off to work. I found that the corset also limited how much I could bend, so putting my socks and pants on was more difficult than usual. I put a shirt on, then a pair of trousers. My waist measurement was certainly several inches smaller with the corset on. I had to tighten my belt to the final hole and my trousers were rather bunched up around my waist. But if I didn't tighten the belt the trousers wouldn't stay up properly. I had a light breakfast. I didn't really feel very hungry with my stomach so tightly constrained. I got on with my chores. My mother-in- law seemed to have a little smirk of satisfaction at the sight of my slimmer outline, but she made no comment. When Helen returned home she commented "Oh dear. Those trousers don't really fit you any more, do they? In fact I think one of my dresses would fit you better." I think she was only teasing, but her mother had heard what she said. "What a good idea," she said. "I'd much rather see him in clothes that fit properly, and we can't afford to go out and buy lots of new things." So Helen and I went up to our bedroom and my wife picked out a dress for me. "I never wear this now as it's a little loose fitting on me, so I think it would fit you OK." I took my shirt and trousers off and Helen helped me into the dress. It was navy blue and had long sleeves. It had a long back zip and the waist was slightly elasticated. When Helen fastened the zip for me I found that the dress fitted quite well at the waist. The skirt was a little short and the bodice was a little loose as I had no boobs to fill it. But actually it felt quite comfortable to wear. It seemed stranger walking downstairs with no trousers on. I had been used to wearing shorts sometimes in the warmer weather, but having a skirt on was rather different. Mother-in-law approved. "Much better than having all that material bunched round your waist," she said. "And it will be quite suitable for wearing around the house." I somehow got the impression that she was exceedingly pleased to see me in a frock. By the end of the evening (after another light meal) I was getting used to smoothing my skirt under my bottom as I sat down, and also remembering to keep my knees together. Once in the bedroom Helen gave me a hug. "How's my little housemaid?" she giggled and kissed me. She unzipped my dress and then untied the laces of my corset. It was such a relief to remove that constraining garment. That night, when we made love, she was on top. The next morning, Helen laced up my corset and helped me on with the dress before going off to work. She phoned mid morning to check something, and then asked me how my housework was going. "OK," I replied. "But I'm not sure about wearing a dress all the time. My legs get cold." "Oh dear," she replied. "On my way home I'll see if I can find anything in the shops." When she returned home she led me upstairs. "I've bought you some stockings," she said. "They'll really make a difference and keep your legs warm. The only thing is though, they look dreadful on hairy legs, so you need to go and shave them. She helped me off with my dress and I went to the bathroom to do as I was told. When I got back to the bedroom she looked at my now hairless legs. "Oh yes. Much better," she approved. "As well as the stockings, I treated you to some pretty knickers as well." She handed me a pair of silky pink knickers. I removed my male underpants and stepped into the pink knickers. As I pulled them up they felt so soft and cool and sensuous... "It's no use pretending you don't like them, "laughed Helen. My stiffening cock was a bit of a giveaway. "I though you might as well make use of the suspenders that were already on your corset," she said. "Thread them down through the leg-holes of your knickers. She took a pair of stockings out of a pack and showed me how to gather one over my thumbs until I could just put my toes in, then carefully deploy the stocking up my leg, finally fastening the three suspenders to my stocking-top. Once I'd put on both stockings, she showed me how to adjust the length of the suspenders. "The front ones need to be nice and taut to avoid wrinkles in your stockings, but the back ones not too taut otherwise you'll have trouble sitting down," she explained. "And always wear your knickers outside your suspenders - it's then much easier to pull them down when you have to go to the little girls' room!" She helped me on with my dress and we went back downstairs. It was certainly true that the stockings felt nice and warm on my legs. I was pretty surprised considering how thin the stocking material was. I was also starting to enjoy the sensation of my suspenders pulling on my stocking-tops with each step I took. And the way my silky knickers caressed my bottom as I walked. In fact, it was only the thought of meeting my mother-in-law that prevented me getting a throbbing hard-on. "Your legs look much nicer in stockings," said my mother-in-law. (I think that this was the most complimentary thing she'd ever said to me). She turned to Helen. "I think you should have a look round the charity shops and see if you can find any shoes for him. Those clumpy shoes he's wearing don't really go with the dress." Helen glanced at me and smiled. "I'll have a look tomorrow." Later, in the bedroom, Helen slipped off her own clothes before helping me out of my dress. She put her arms around me and as we kissed her hands fondled my bottom through my silky knickers. As she rubbed her body against mine my cock got rock-hard. She led me over to the bed. I lay down and she lowered my knickers to mid thigh, then straddled me. On my back, wearing a corset and stockings, with my knickers pulled partly down, I was the one being fucked. And Helen was in control, keeping me on the edge of orgasm until she was ready. When she finally allowed me to explode inside her, her cunt muscles gripped my cock tightly, squeezing and milking me dry. I pulled my knickers up and we lay side by side for a few moments. "Darling," she said, "I can feel the love juices starting to leak out. I don't want to drip all over the carpet." She straddled me again, this time with her cunt over my face. As I licked her warm cunt our combined juices trickled into my mouth. Eventually she climbed off me. "Thank you darling, that was wonderful," she said. "Take your stockings off and I'll help you off with your corset. Keep your knickers on, though. I know you like them. And I like the effect they have on your cock!" The following morning Helen suggested that I try to lace up my corset myself. I thought it would be difficult, but in fact the hardest part was tying the bow behind my back. "OK," she said, "I bought you three pairs of stockings - they're all the same shade, so if you damage one of a pair you can still use the other. And I bought 5 pairs of knickers, all in different colours, so you can choose which you'd like to wear today. I chose a red pair that had a bow at the front and frills around the leg-holes. Helen smiled as I put them on. She could tell I liked them. Knowing that she was watching me put my stockings on made my cock even harder. Helen let me try doing up the zip on my dress. This was much more difficult than I expected. My arms were not used to reaching behind my back and my corset restricted my freedom of movement. "You'll have to practice the zip," she said as she finished fastening it for me. "Now since you don't have as many pairs of knickers as I have, you'll have to wash yours regularly so that you can have a clean pair every day," she instructed. "Hand wash them in the wash basin and hang them up in the bathroom to dry - you'll find they dry very quickly. It's best to wash your stockings every day or two as well." She went off to work and I had my now usual light breakfast - crispbread and coffee - before getting on with my household chores. I seemed to be getting on better with my mother-in-law now. She hardly complained about anything. Helen returned home in the afternoon. She had found a pair of shoes for me. Second-hand, but in good condition, hardly worn, in fact. They were black with two and a half inch heels. "I hope they fit you OK" she said. "It was the only pair I could find in your size." I tried them on. Not only were they a good fit, but I was amazed how it felt to walk in them. My bum seemed to stick out more, and when I looked in a mirror I saw that they changed the shape of my legs too. I now had shapely calves and dainty ankles. "He's got pretty legs," said my mother-n-law to Helen. I found I had to walk more daintily in shoes with heels. My bum seemed to waggle more and I could hear the gentle swishing sound as my nyloned thighs brushed together. And of course there was the sound of my footsteps when I walked on a hard surface. Unmistakeably the sound of walking in heels. The two women watched me walking around. "That dress suits him," said my mother-in-law, "but it's a pity that the bodice is flapping about loosely. We need to get him a bra and pad the cups out with something. Then the dress will fit properly." Helen nodded approvingly when she saw my washed knickers and stockings hanging up in the bathroom. "It's always best to be wearing clean knickers," she remarked. "Just in case anyone sees up your skirt." That night our love-making was as vigorous as it had been the previous night. And it followed the same pattern. I began to feel that I was the wife and that Helen was the husband. The next day followed a similar pattern. I was able to dress myself and even managed the zip on the dress. I was aware that my mother-in-law was watching me more closely as I got on with my household duties, especially when I went up and down stairs. I felt a little thrill when I realised she was trying to look up my skirt. I was a little disappointed to see that Helen did not seem to be carrying any shopping when she returned later. But she reached a small piece of fabric out of her hand bag. "Its a bra extender," she explained. "See, its got hooks and eyes that will link with the hooks and eyes on a bra. This will increase the bra band size by a couple of inches, so one of my bras should fit you." But her mother produced a bra for me. It was white and in a rather old-fashioned style with cups designed to completely enclose the breasts. "Actually, I think this will be better than any of mine," said Helen. "There's no risk of whatever we pad it with falling out." Up in our bedroom Helen unzipped my dress and I took it off. Then I found myself wearing a bra for the first time. We padded the bra cups with a few pairs of my male underpants. "You're not wearing these any more, are you?" she giggled. When I put my dress back on, the bodice fitted my new bust perfectly. The dress felt much nicer to wear as it more or less clung to my upper body. This made me even more aware of how my skirt floated around my thighs and was not in constant contact with my body - a sensation of both freedom and vulnerability. I felt a little tingling in the end of my cock at the reminder that I was relying on my skirt hanging normally in order to prevent my knickers and stocking-tops from being displayed. And, of course, revealing that I had a cock in my knickers. Helen gave me a little hug. "You look very pretty, darling," she said, "but we need to do a little bit with your face too. She led me to the bathroom. "Your eyebrows are too bushy," she explained. She used a comb and scissors to trim them back quite severely. "Now just a hint of lipstick." She opened a new lipstick, a pinker shade than she was wearing herself. "I got this just for you." She showed me how to put on the lipstick. "it looks easy," she said, "but you'll need to practise." We went back downstairs. My mother-in-law approved. "Who's a pretty boy, then?" And she actually smiled at me. Wearing a bra was quite comforting. The straps were not tight, especially compared to the restrictive corset, but they gripped just enough to remind me that I had a bra on. And as I said, the bra made my dress feel so much well-fitting and comfortable. My new clothes were a strange, but rather pleasant mixture of constraint and freedom... The grip of my corset, bra-straps and taut suspenders contrasted with the silky softness of my knickers and the almost imperceptible lightness of wearing a skirt instead of trousers. I also discovered the new sensation, when reaching for something in front of me, of my upper arm coming into contact with my bust. And when sitting at the table to eat, the twin mounds on my chest were in view every time I looked down at my plate. That night I was wearing my bra as well as my other underwear when Helen mounted me. On Friday Helen announced that she had the morning off. "But you need to get up early because you're coming with me to the shops." she explained. "If we go to the mall early there won't be so many people around." I clung to her arm rather nervously as we walked to the shopping mall. It wasn't too far and I was wearing a borrowed coat that was rather longer than my rather short skirt. But I felt as if everyone was watching me. I was rather surprised when we headed straight for a beauty parlour. "A special treat for you," said Helen. "The stylist is an old school friend of mine." It was agreed that my hair was just long enough to "do something with". and while the setting lotion and curlers were doing their "something", my nails were manicured and painted pink and my ears were pierced and studs fitted. A little later we sat side-by-side in a caf?. "I didn't think we had money to splash out on hair stylists and manicures," I said. "Well you have to see it as an investment," replied Helen. "You've got a job interview at 2 pm and I want you to look your best." I froze. "A job interview??? I can't go to a job interview looking like this." "Don't worry, darling," soothed Helen. "They want you for your computer skills, not for your body. Your body is for me." As she said this her finger traced the outline of one of my suspender clasps through my skirt. She went on to explain that the small company she worked for needed some technical help. It was an all-girl establishment and, despite equal opportunity employment legislation, they wanted to keep it that way and could not in any case afford to employ a high flyer. Helen said she'd told them that I wouldn't mind fitting in as one of the girls, and after some discussion they had agreed to consider taking me on for a trial period subject to my attending a short interview. "And when was all this discussed?" I asked. "Well, the need to find someone to help the office has been talked about for a couple of weeks. But when I saw you in a dress for the first time I knew you'd be perfect. And look how much you've progressed in a week. Nobody would realise you were my husband, with your slim waist, pretty legs and shapely bust. And I'm sure you'll be happier working in an office full of girls rather than spending all day at home with my mother. Anyway, please come to the interview. If you really don't want the job you can turn it down." As I walked with Helen to her employer's office, many thoughts streamed through my brain. I realised that there must have been more collaboration than I had thought between my wife and her mother in order to get me feminised so quickly. It would be good to have a job again, and I hadn't found an employer who wanted me as a man. And although I was rather nervous about the whole situation I found the idea of working as an office girl quite stimulating. And in my first week as a sissy husband Helen and I had had the best sex since we met. So it was clear that I'd be wearing women's clothing at home for the foreseeable future in any case. By the time we reached the office I had decided that I really wanted this job. Helen took me to the boss's office and introduced me. "This is Didi," she said, which was a complete surprise to me. But I found the name quite attractive. Helen went off to her desk, leaving me with Miss Andrews, the owner of the business. She asked me first about my previous employment and experience, and explained what was needed to be done in her office. I could understand what was needed and was confident that I could help sort things out. Then she broached the subject of clothing. "It's a rather delicate situation," she said. "Obviously I can't write a job description or an employment contract that specifies that the candidate must be female, or even must dress as a woman. But we are a small company and have worked together very well for a couple of years being all girls. We have discussed it in the office and the general feeling was that having a man around the office could disturb the equilibrium. When Helen suggested that you would be prepared to work here as one of the girls we didn't know at first whether to be shocked or amused. But we quickly realised that it could be a very good solution for us. So you must understand that all the girls in the office will know that you're a man in a dress and Helen's husband, but they are prepared to accept you as someone who is ready to meet them half-way as you might say. I'm willing to offer you the job on a trial basis for four weeks. You'd work the same hours as Helen, which I guess would be convenient for the two of you. But if during the trial period it's clear that things are not working out either for us or for you, we'll terminate the employment. Is that OK?" She went on to explain what wages were on offer. It wasn't a fortune, especially as it was only a part-time job. But it was a lot more than nothing, which was what I was earning right now. I accepted the offer. I was introduced to the other office staff by Miss Andrews. "This is Didi. She'll be working with us from Monday, helping us sort out our computer systems." I smiled nervously and murmured "Hello, everyone." They were all smiling at me in a friendly fashion. I was aware of some glances at my stockinged legs. I remembered that they all knew that I was Helen's husband. And that I had agreed to wear women's clothes in order to fit in with them. I didn't know whether they would treat me as another female colleague, or just regard me as a sissy - less than a man and also less than a woman. I realised that a sissy was exactly what I was. And, strangely perhaps, I felt more at ease with that realisation. No need to pretend I was anything else. I thought that I would be able to fit in to the office group very well. I knew I was a sissy. And they did too. The staff were mostly of a similar age to me (I guessed), with a couple obviously rather younger. It was the younger ones who seemed slightly unsure of the situation. One or two of the others seemed to have a glint of satisfaction in their eyes, though. I was shown my desk and the location of stationery cupboard, where to make hot drinks, etc. And of course, the washroom. It wasn't difficult to understand that this was perhaps the most sensitive area as regards allowing a man into the office. There were a couple of stalls, but no urinal. A dispenser for tampons. Washbasins with dispensers for perfumed soap and large mirrors. Clearly an environment for female staff. And sissies. "I'm so pleased you got the job," said Helen as we walked home. "We'll go shopping tomorrow and get you a few more clothes, so that you don't have to wear the same frock all week." I was once again hyper-aware of each item of female clothing I was wearing. The gently insistent grip of my bra straps and the warmth of the filled bra-cups around my nipples. My silky knickers caressing the cheeks of my bottom and comforting my hairless genitals. My corset firmly gripping and shaping my waist. My suspenders stretching with each step and emphasising the tautness of my stocking-tops. My heeled shoes forcing me to walk in a dainty way, changing the shape of my legs and making my bum stick out more. My dress, or perhaps more significantly the absence of trousers, relying on gravity alone to ensure that my skirt concealed my pretty underwear and in particular the tell-tale male outline of my knickers. Each item of clothing in turn seemed to be reminding me that they had got me the job. Each time we passed a shop window with women's clothes on display I found myself looking for what I'd like to wear. Back home even my mother-in-law seemed pleased that I had been successful at the interview. And later, my naked wife helped me out of my dress. We stood in front of the mirrored doors of the wardrobe. She pressed her body to mine, one of her hands fondling my knicker-clad bottom while the other explored the firmness of my erection straining at the front of my knickers. She spoke softly, as if it were the voice- over on a film. "And this is my sissy husband, Didi. You can see how much he likes wearing pretty things. And just to please me, he is going to stay hard until I am ready for him to release inside me. And them I am going to milk him dry. Then he in turn will clean me with his tongue..." I wondered if she was only speaking to me. Was there a hidden camera? It was with some trepidation that I arrived at the office to start work. I was a little reluctant to release my grip on Helen's arm as we entered the front door. She, on the other hand, seemed happy and confident. I exchanged Hellos and smiles with the other staff already there, and with the others as they arrived later. Most of the first day I spent at my own desk, getting to understand how the IT systems had been set up. One or other of the girls brought me a cup of coffee from time to time. As the week progressed, I spent time with each of the other girls in turn, trying to understand how they used the systems and what problems they encountered. The discussions were all friendly, but business-like - after all, my wife was present in the office. On the odd occasions when she wasn't there, however, the conversations were often rather more personal. There was the time when I was sitting with Barbara. She put her hand on my knee. "Do you enjoy wearing a skirt and stockings?" she asked. "By the way, I did notice you're wearing stockings, not tights. Suspenders are sexier, aren't they?" She laughed as I felt myself blushing. Obviously I had been careless when sitting down and had allowed a view up my skirt. I felt a little tingle in the end of my cock at the thought. I hoped I wouldn't get an erection. On another occasion, Angela remarked that Helen was very lucky to have such a pretty husband. Even when Helen was present there would be "girl talk" about clothes, film or TV actors, personal relationships, and so forth. I would be included in the conversations and asked my opinions. As time went on, some of the subject matter got into more intimate details. I got the impression that some of the references to underwear and sexual activity were intended to try and get me aroused, knowing that an erection under my skirt might be difficult to conceal. For the most part, however, people got on with their jobs, including myself. I proposed a number of changes to working methods and systems. These were mostly accepted and I helped to implement them over the weeks that followed. I could see that the office was operating more efficiently and we were getting more interaction and feedback from customers. Turnover increased and everyone seemed happy. I was more confident in my work, and also more at ease in female clothes. Helen was also even more self-assured. Outside the office environment she was the one who made all the decisions. She chose the clothes I should buy and decided which outfits I should wear each day. It was her decision to purchase some quite expensive silicone breast forms for me, so that my bust moved more realistically (these were much heavier than the padding I used to fill the bra cups with, but I soon got used to the feel of "my" breasts). She now wore trousers most of the time. And she continued to take the lead in the bedroom, always on top and always determining the rhythm. It was my function to hold back my own orgasm until she was ready, and then to clean her with my tongue - recycling, as she described it. She bought a chastity device for me too. "It's not because I don't trust you," she explained, "but you'll be locked into it when I have my periods. It'll help you understand what it's like when your sexual organ isn't available for a few days each month." After I'd been working in the company for about three months, Miss Andrews called me into her office. "I'm extremely grateful for the way you have improved our work systems," she said. "But I guess we both know that it is time for you to think about moving on. You've achieved what we needed, but now I'm giving you four weeks notice. You can leave sooner if you find another post. I'll give you an excellent testimonial for your next employer and a bonus when you leave. In fact, I happen to know that another company is looking for someone with your talents right now. It's a larger organisation and would probably offer you full-time employment. Would you like me to get more details?" I nodded, thanked her, and went back to my desk. Thinking about the situation, I had to agree that my task here had been largely completed. There wasn't a lot more I could offer in terms of further improvements. In fact it was quite generous of Miss Andrews to be prepared to keep me on for another month. Talking it over with Helen, she thought it would be worthwhile to investigate this new opportunity. "It won't be quite so convenient for us if we're not working in the same place with the same working hours, But it would be good to be able to increase our earnings, wouldn't it?" The next day, Miss Andrews handed me a package. "It's the details of what I mentioned earlier," she said. I quickly looked through the first few pages during my lunch hour, but then put it aside to read at home in more detail. I could see that it looked quite promising, but I didn't want to share it with the other girls in the office for the time being. I sat on the settee at home and opened the package. It contained several documents, the first being a profile of the company: what business it was in, where it was located, how many employees it had, and so one. This was clearly not a small all-female office. There was a job description of the vacancy and I could see that I was well qualified for the post. It was really a similar job that I'd been doing for Miss Andrews, but on a somewhat larger scale. I decided that I would definitely apply for the vacancy. I had enjoyed the challenge of the work I'd been doing for the last few weeks and had been glad to get back into the routine of being employed after an unwanted but extended lay-off. I had to admit that I had also enjoyed being dressed to be "one of the girls" in the office. But it would be good to be a normal working man once again. I could still dress up at home, and at weekends as well, perhaps. In fact I thought with a smile that Helen would probably insist. The post carried a decent salary - quite an increase from what I was currently earning. And the office was conveniently located. So YES. This job was just what I wanted. I could resume my former career as a male again after a brief spell as an office girl. There was an application form in the package. A Post-It not had been attached. It read "Interview 11.00am Monday." I quickly looked through the form. It was straightforward enough. Before I started filling it in I looked at the final document. It was a letter from Miss Andrews, her reference to my potential next employer. It was a glowing testimonial, but my pulse started racing as soon as I read the first couple of sentences... "Didi has been working with us for the past fourteen weeks. SHE is an excellent worker and has achieved outstanding results..." Helen sat down beside me and put her hand on my knee. "Isn't it exciting," she said. Her probing fingers moved slowly up my skirt and I compliantly parted my legs. "I've booked an appointment for you with the beautician first thing Monday morning. You'll want to look your best for the interview, won't you?"