A Transvestite Maid, Who Just Wants To Please free porn video

Preface: I've only started writing recently and am keen to develop. For me the thrill of transvestism and the fantasies that surround it, is driven by what takes place in the mind. I'm hoping that my readers will appreciate Penny's journey as being something more than a sexual experience and will identify with that desire for someone else to always be in control. Penny can always justify her experiences by claiming that she was coerced unwillingly. A Transvestite Maid, Who Just Wants to Please... By Penny Maid How it started... Everything in my life has changed so much since my wife Liz took control. Now I exist to serve both her and her friend Mistress Grace to whom I am sent for training. It all started when Liz found out my little secret (she came home unexpectedly one day and caught me trying on her underwear) she reacted in a surpassingly calm way. "Of course I've always suspected that there was something different about you," she said, "I married you because I like the way you treat me and you are easy to be around, but in truth I have never felt you were manly enough for me... now we know why." She continued "I wish you had told me about this earlier, it really didn't have to be a secret, everyone should have the opportunity to express themselves and to be who they really want to be." I was left completely speechless (not least because I was still standing in our bedroom in front of her wearing one of her basques with seamed stockings an embarrassed smile and a barely concealed erection). "And before you try to make any silly excuses about why you are wearing my clothes we can both see that you appear to have a huge erection trying to burst through my panties. I haven't seen you as hard as that in a long time." It seemed pointless to protest, the truth was that our sex life had evaporated into fairly brief encounters and I had found it increasingly difficult to satisfy her. Whilst making love with her I would often fantasize about "forced feninization" scenarios and by doing that I had been able to get hard enough to appear enthusiastic. Now my secret was out but rather than shout she was calm and looked at me with a loving smile. "You know I can't believe I'm saying it, but I think you may even look better in that stuff than I do! You really have great legs, with a little bit of work I bet you could pass as a woman, hah! Whatever shall we do with you?" As she spoke I could feel myself getting even more excited and my arousal was very obvious as my cock bulged through my panties. She looked at me with a sly smile, "you know it would be such a pity to waste that... " and with that she walked towards me still smiling, she put her hand inside my panties and grabbed my erect cock and as she did so she turned and led me to the bed with her hand firmly wrapped around me. "Come along now, there's a good girl, I'm in charge now." She pushed me back on to the bed and immediately climbed on top of me. She hitched up her skirt and with my cock in one hand she used her other hand to pull aside her own panties and guided my cock to her glistening wet pussy. She didn't give me any say in the matter, she was totally in control and she knew it. As she put my cock inside her and pushed down hard on me she said, "from now on we do everything my way, if you want to be a girl, then you have to play by my rules is that clear?" I was in a frenzy of excitement and would have agreed to anything. "Yes of course," I said, "I'll do anything you want." "Good, the first thing is that you are NEVER to reach orgasm without my permission, is that clear?" "Yes," I replied, "Good girl." She continued to ride me and my excitement was increasing with every moment, just by her referring to me as a "girl" sent shudders of excitement through me. "Now that we have found out your secret, things will have to change. You cannot reasonably expect me to regard you as my husband. You can continue as my 'partner', in fact it will be fun to have a female friend to confide in, we can still live together but not as husband and wife. That's non negotiable I'm afraid." "But..." I protested She pushed down hard on me and pinned me to the bed by my shoulders. "No 'buts', darling, it's simple, you want to play at being a girl and I am happy to help you. We have passed the point of no return. If you refuse to do things my way I will simply tell everyone that I know about your secret. You see, what you hadn't realized when you started to play 'dress up' with my clothes was that you were giving me a wonderful opportunity to take complete control of both of our lives. It's an opportunity that I fully intend to take. Oh - and by the way - I probably ought to let you know that I have actually known about your secret for a while, I suspected that something was going on so I discreetly set up a spy webcam in our bedroom a little while ago. Imagine my surprise when I saw the film of you putting on my underwear! Mind you I was even more surprised when I saw how enthusiastic you were about playing with my vibrator! Bad Girl, you really should get your own! Anyway everything is recorded but I wouldn't dream of showing your family and friends anything as long as you do everything I say, understood?!" "I understand," I replied meekly, although I was secretly thrilled at the way she was taking control. I thought I had better show some kind of resistance, "but this is such an extreme way of dealing with things." "Well, that's your problem not mine, I'm afraid. And by the way I think it would be easier if we changed your name, you need something that will suit your new life. From now on you are to be known as Penny, its such a nice feminine name." "Of course you will need training. I'm too busy at work and I think it would be better if you were in the hands of an expert. You may remember an old friend of mine, Grace, well we got a little drunk a few weeks ago and she told me that she has an interesting sideline as a dominatrix." "I told her about what I had seen on the webcam and it was she who encouraged me to see this as an opportunity. She has volunteered to take you in hand and you are to report to her house for your feminization training first thing tomorrow. Isn't it exciting?" It was at this point that I lost control, my excitement had been building as she dominated me so completely and I felt an electrifying surge go through my cock as it spasmed into orgasm. Her response was immediate, she slapped me across the face with stinging force. "You are never to do that again, my pussy is now reserved for the cum of real men, not girly wannabees like you." With that she placed her knees on my shoulders, pinning me down and lowered her pussy onto my face. "Lick me until I am clean," she said, "it's a taste that you will have to get used to...." Letter from my Mistress "Your new name will be Penny, Let me tell you a little about who and what you will be." "Eventually Penny will be employed by one of our wealthy female clients. I can't tell you just exactly who she will be, but suffice it to say that in your eyes she will be the most beautiful woman you have ever known." "You will dedicate every waking moment to ensuring that she is happy, healthy and content. You will have no sexual feeling for her, of course, or for any woman for that matter; this would only compromise your role as a servant. You will admire her, though. In your heart of hearts, you will wish that you could be her. Everything that she touches - her clothes, her undergarments, her makeup, her shoes, and her jewellery. You will be nothing. She will be everything, all that is good and beautiful and worthy of being loved. Your existence would have no meaning if it were not for Her. You will work very very hard, Penny. Your days will be filled with cleaning, washing, ironing,, seven days a week, three hundred and sixty five days a year. What little time you have for yourself will be spent improving your appearance. Your undergarments and uniforms will always be immaculate. Your makeup will always be fresh and perfectly applied." "And sometimes, Penny, when it is late at night and you are not too exhausted from your long day of service, you will pleasure yourself in a manner consistent with the feminine consciousness we have created for you. You will find yourself fantasizing exclusively about men: strong and powerful men who are as strong as you are weak, who are as hard and forceful as you are soft and submissive, men alone or men in groups who see you only as a sexual object, men who want to possess your body in every conceivable way again and again and again." "As time passes you will naturally want to make your fantasies real. Perhaps your mistress will give you a night off now and then. Perhaps she will have given you some of her precious, castaway clothing. Perhaps you will put on a tight dress and high heels and spend an evening looking for male companionship at a local bar. All will be possible once you are a woman." "I know this is very hard for you to imagine, and it might be more than a little frightening as well, but I assure you that we do this for very good reasons. You will simply be much happier if you learn to do as you are told." "Being a maid will be the most important and treasured thing in your life, next to your mistress's happiness." "So there it is Penny. I would ask you if you still wanted to go through with it, but we both know that it is too late for second thoughts. You have not been happy as a man, but now I am here to make things better. I look forward to seeing you next week. Please be sure to have your affairs in order, as there is no turning back." Mistress continues with Penny's training... "You are such a good girl" You take me by the hand and lead me to the bed room. You have positioned a chair directly in front of the mirror. "Now" you begin, "here's how its going to work. I want you looking straight into the mirror, I want you watching me fuck you with my strap on dildo. I'm going to train you to love it like the little whore you are. I know that you are a virgin, but if you are going to be a good maid you will have to accept this without resistance or question. I am going to make it easier for you. My hands will be wrapped around your cock. BUT, you only get stroked if you push back against the dildo when it is inside you. When you go down on your dildo cock, you will feel my hands going up your sweet cock. When you come up off that dildo cock, you will feel my hands stroking you down on your cock. You see, my hands, although they will be wrapped around your cock WILL NOT MOVE, you will only feel the pleasure of the stroking if you fuck my hands, as you ride the dildo cock. From now on you will learn that you can only ever cum when you have a cock inside you. You will learn to crave it. "Now, my sweet little slut... ride!" It is hard for me, I really don't want anything to violate me, but the sensation of your hands is too much and I start my rhythm. Shallow dips at first, craving the feel of your hands, I so want to fuck you hands. "Oohh, I start to cry... please, stroke me, it feels so good," I say. "Good girl, that's the way, ride the cock! Look!, look, sweet little girl, look how good you can ride a cock," pointing my face toward the mirror. "Let's see if we can take it a little deeper," you urge me on. I follow your command and start taking slow deep thrust loving your hands, and being deeply probed by your dildo cock... I begin to enter my orgasm... "oooh"... I cry. "Come on... come on, little girl... come for me. Ride it, ride that cock!" "OOOOhhhh!!" I cry. "That's it, good girl, cum for me, cum for your Mistress!!" "AAAHHH", I fall back on to the bed orgasming... for you... you taking one hand to finish me off, stroking me firmly, and with the other hand fucking me with the dildo. I am laying back on the bed, legs spread, like a good little slut... the journey continues. Friday As usual I arrived at my Mistress' house on time on Friday, and as usual she looked immaculate resting on her chaise longue, issuing commands in such a confident effortless way. I had learned at an early stage that her word is law, and anyway I had been forced by my wife Liz to sign a contract agreeing that I would accept without question that both Liz and Mistress Grace had complete control over my life and all decisions. I knew that they found it amusing that it was so easy to control me and whilst Liz kept telling me how much she loved me, I always thought that Mistress Grace just saw me as a plaything. They had photographs though, and the threat of public exposure meant that I had no choice but to do as they said, even if they seemed to be leading me down one way path. As soon as I arrived at Mistress' house the routine was that I would immediately go upstairs and change into my maids uniform. Mistress told me that it was important to wear a uniform so that everyone would be able to clearly understand my place in the pecking order. Although my Monday to Thursday existence still involved working in a busy office as I had always done, Mistress insisted that Fridays should be entirely feminine days. My legs had long since been waxed and although I wouldn't admit it I had come to love the feeling of pulling silky stockings over my perfectly smooth skin. I stepped into the uniform, put an Alice band in my hair, applied my red lipstick in the way that I had been taught, and went downstairs to report for duty. My working day on Fridays had become fairly routine. Mistress had given me a schedule which included the laundry, dusting and hoovering the house and of course doing the ironing. She said that it was extremely important for me to show my value to my Mistress at all times and she certainly had no intention of doing any household chores herself. It was only after I had completed my chores that she would start with other aspects of my training or "attitude adjustment" as she called it, but I will tell you more about that on another occasion. Anyway on this occasion I was busying myself with some ironing when Mistress walked into the room and told me that she was going out for a while and would be back later. "Oh by the way, I'm expecting a delivery of some garden furniture later," she said, "if they turn up while I am out you must make sure that they take it through to the back of the house and assemble it before they leave." I panicked and protested, "but I can't answer the door dressed like this!" "Penny, if you fail to do as I ask, then you will have to be responsible for the consequences. This is not a joke, and its not a game. You are my maid now and if I want you to take a delivery for me then you will do it without question. Do I make myself clear?" "Yes Mistress." "Good girl, it would be such a shame for your work colleagues to see some of the photos we have of you now. If the door bell rings I expect you to answer it without hesitation. In the meantime you have ironing to finish." And with that she turned and left the room, left the house, and left me in a state of near blind panic. I continued with the ironing, it was a sunny day and with the windows open a gentle breeze fluttered through the room. I figured that delivery firms are notoriously unreliable and anyway I calmed myself with the thought that Mistress was probably just having a joke at my expense and that no one would show up at the door. I turned the radio on and soon became lost in another world, listening to old songs and indulging in absent minded daydreams. As I stood there with the soft satin of my dress brushing gently against my thighs every time I moved , I began to think about what it would have been like if a delivery man had turned up. What if he was big and powerful, and mistaking me for a real girl had taken me against my will? I was shocked by how turned on I became, and I remembered the hypnotic conditioning that my Mistress had imposed on me early in my training. She had told me that I would start to fantasise about men. I had dismissed it as silly and pointless, just part of a game, but here I stood, only a few weeks later, my pulse quickening at the thought of what might have been. Suddenly I was snapped out of my day dream by a loud knock at the door. I froze. Mistress had a set of keys so I knew that it couldn't be her. There was another loud knock at the door and as I cowered in the hallway I could see through an open window that there was a delivery truck parked on the drive. My heart rate went through the roof. Mistress had left me in no doubt that I had no choice but to open the door. If I failed she would tell everyone my secret and the photographic evidence was excruciatingly embarrassing. My career would be ruined and any humiliation would be far greater even than what I would suffer in opening the door. At least the delivery man wouldn't know who I really was. I decided that the worst thing that could happen would be that he would laugh at me, perhaps make a joke and then get the hell out of here! I took a deep breath and opened the door. He was gorgeous. 6ft 4 ins tall, maybe mid 30s, very muscular, wearing a tight shirt with cut off sleeves and blue jeans. He smiled at me, "Hi!" he said, "I have a delivery for you, where do you want it?" "Oh, can you take it through to the back of the house please," I stuttered as quietly and softly as possible, "My Mistress has also asked me to remind you that she would like the furniture assembled." "Your Mistress?" he smiled again, " So you aren't the lady of the house then? Is she not here to sign for the goods?" " No I'm afraid not," I replied, "I'm not sure when she'll be back." "That's fine by me, you'll do nicely!, I'll get the things from the truck." I couldn't believe it, he had reacted to me in a perfectly normal way, seemed like a really nice guy and was just going about his business. Maybe I was going to get away with it! It didn't take long for him to unload the garden furniture from the truck. I watched from the kitchen as he started the job of assembling the pieces. He was a seriously fit looking guy and it wasn't difficult to just stand there admiring him. I could see that it was quite physical work and it was a gloriously sunny day. I suppose I should have been prepared for the moment when he took his shirt off to stop himself getting too hot. He had muscles to die for and as I gasped and muttered a barely concealed "wow" under my breath, he looked over to me and smiled. "Hey sorry about stripping off my shirt like this, I hope you don't mind but its hot work out here." "Oh no, that's fine, I understand," I replied. "Can I get you something cold to drink?" "Yeah, that would be great, thanks, what do you have?" I had absolutely no idea what Mistress kept in her fridge. " Err, not sure, I'll take a look." I smiled back at him and went to the fridge and stared blankly at its contents. I couldn't believe the situation I had found myself in. I hoped that no one would ever find out. Mistress wouldn't be back for a while, and if she didn't find out that I had been flirting with the delivery man then Sue would never know. No need to panic. Everything would be fine. Just give him a drink, let him finish the job and then he can be on his way. No harm done. I guess he must have become impatient whilst I looked through the fridge trying to find something he might like. "Not having much luck?" he said as he breezed through the back door into the kitchen, "let's take a look at what you have hidden away in there shall we?" He flashed me that smile yet again and came over to the fridge. He positioned himself right behind me, peering over my shoulder into the fridge. He was very close to me and my pulse was quickening again. I was out of my depth. He deftly slipped his arm around my waist, gently holding me from behind, gently but firmly pulling me towards him. "I'm sorry," he said, "but I think that these maids uniforms are such a turn on. You don't see many women wearing them nowadays and the silk stockings as well, its all too much for me I'm afraid, I'm as horny as hell and I need a woman!" Now I was worried. The fantasy moment had been replaced by the fear that I was about to be exposed for what I really was. He was twice my size and could easily beat me to a pulp if he wanted to. "Please don't" I said as his other hand reached around me, locking me in his grasp. "I'm not that kind of girl, really, I'm not what you want" "I know exactly what kind of girl you are Penny, and right now you are what I want." He knew my name. How the hell did he know my name. I hadn't told him. He spun me round so that I was facing him, I was pressed up against his naked torso and could feel his immense strength. On the one hand I was terrified and on the other I was thrilled by his power and the certainty with which he handled me. He looked at me, smiled again and said "I've known your Mistress for years, I used to be her personal trainer before I got into the delivery business. She's told me all about you. I'm here as part of your training program!" I tried to pull away but his grip was to strong for me. "Penny, if you want to be a maid then you have to learn how to look after your men as well as your Mistress," he said. And then he scooped me off my feet and simply said, "I think its time that we went upstairs." I was powerless to resist. As he carried me in his arms he kissed me. A deep lingering kiss, his tongue pushed firmly into my mouth. I couldn't help myself, I found myself putting my arms around his neck and kissing him back, kissing him with passion wanting him to take me. As he carried me to the stairs I suddenly caught sight of my Mistress, she had returned without me noticing. In her hand she held a video camera which she was pointing at us. She had recorded everything. She smiled at me, smiled at him. She walked over to us. She kissed the delivery man on the cheek. "Be gentle with her" she said. And then she turned to me, she whispered in my ear. "Go on Penny, you know you want to..." Day dreams... I curled my fingers around his cock and felt it throb as his tongue traced lightly along my jaw to my earlobe. I couldn't believe that I was actually touching his cock, or rather trying to pull it through the leg hole of his shorts. My free hand reached up to the snap and he kissed his way from my ear to my neck with little bites and sucks to burrow under the collar of my uniform to my shoulder. I pulled his trousers down just far enough to expose his member. He stood up straight and took a step around the chair so that his cock was level with my mouth. With my right hand slowly moving up and down his shaft and my left hand squeezing his sack, I pulled my first real cock within inches of my mouth. "Oh God Penny," he groaned, "You make me so hot, I'm going to lose it way too fast." I looked up at him, smiled, licked the head of his penis and squeezed his balls. He came immediately, his first volley of cum hit my nose before I could open my mouth. I managed to catch the next spurt and felt four or five more throbs and eruptions before he fell back to the couch. I leaned forward with him, keeping his cock inside my mouth and sucked the last few drops of his cum. As I felt his member soften between my lips, listening as his laboured breathing slowed and became more even. I savoured the bittersweet flavour of his semen. One thing I realized was how much making him cum excited me. I really enjoyed it and I would have been happy to feed on his cock all afternoon. Barcelona I got home in the early evening of that eventful Friday expecting to see Liz, but all I found was a note on the kitchen table saying, "I'm out with the girls tonight, don't wait up! x." After everything that had happened it seemed unreasonable for me to complain, but I was disappointed because I felt the need to talk with her. So much had happened so quickly and I was confused and feeling totally out of my depth. The next day we were due to go away together for a few days so I figured that would give us both an opportunity to draw breath and get some normality back into our lives. To be honest I was looking forward to leaving my new alter ego of Penny behind for a few days. The next morning involved the usual pre-travel blur of activity, packing suitcases, checking tickets, confirming taxi rides to the airport etc. The plan was to fly to Barcelona for a long weekend. Liz had arranged it and had booked us into a lovely hotel le Meridien near the busy Las Ramblas district. Her planning was always meticulous, our driver turned up on time, we got to the airport on time and it was only when the driver unloaded our bags that I realized that my bag wasn't there. Liz was quick to reassure me, "Don't worry, I decided to take one big bag rather than two smaller ones, I put all of your things in for you." "Oh, ok, thanks," I replied, thinking nothing more of it. The rest of the journey went very smoothly and we were soon at our hotel. It was early afternoon and our plan was simple: shower, get changed and head out for a glass of something fizzy in a nearby bar so that we could work out our plans for the next few days. Liz showered before me, and as I undressed in readiness to use the shower after her I put my discarded clothes into a laundry bag. I'd worn cream chinos during the journey and they looked decidedly grubby. I figured that hotel laundries usually do a pretty good job so I made the call to housekeeping and put the bag by the door. I went into the bathroom whilst Liz was still in the shower. She has a fabulous body and looked irresistible as she massaged herself with soapy lather. Taken by the moment I stepped into the shower to join her, my cock already semi erect in anticipation. "What are you doing baby?" she said in a quizzical way. "Well I thought..." I replied, but she quickly interrupted me, "Penny, you need to understand that we have agreed how things will be between us, this isn't a game that you can play by your rules whenever it takes your fancy. You have admitted that you like being a female, so as far as I am concerned you are one. Now stop being silly and let me finish my shower." What she had said shocked me because despite the intensity of the previous few weeks I had seen it as an extended fantasy game. I really hadn't considered the possibility that this was something that was destined to change our life together in any kind of extreme way. I still thought that Mistress hadn't yet told Liz about the events of Friday with the delivery guy. We'd left for Barcelona so soon afterwards I assumed that they hadn't had time to speak, and anyway Liz hadn't mentioned it. God if Liz did find out there really would be no going back. Suddenly the enormity of the situation was beginning to hit home. I decided not to push the point with Liz and just to go with the flow a little. The plan had always been to use the time in Barcelona to relax and enjoy some time together. With that in mind I waited my turn for the shower and then spent the next 15 min or so with the water on icy full blast and emerged cleansed and invigorated. Liz was dressed, made up and ready to go out as I stumbled around the room searching through the cupboards looking for my things. "What's up baby?" she smiled, "Just looking for my things" "I unpacked for you," she said, "it's already in the wardrobe and your underwear is in the second drawer down in the chest of drawers." "Thanks," I replied but as I opened the second drawer I immediately realized that she had made a mistake. "Liz this is all your stuff..." "I don't think so baby," she replied as she came over to peer into the drawer. "No, those are definitely your things Penny, mine are all in the top drawer." The drawer was full of ultra feminine underwear that I had never seen before. Looking at the labels most of it seemed to be from Myla's boudoir collection. I went to the wardrobe and again there was no sign of any of my clothes. All I could see were Liz's clothes, a mixture of dresses, tops and skirts, some of which I'd not seen before. "Liz, what's going on?" "Oh Penny, relax," said Liz smiling at me, "we are in Barcelona, miles from home, nobody here knows you. The only male clothes that made the trip were the ones that you were wearing and they are in the hotel laundry now. You should be grateful that I went to a lot of trouble to buy some lovely new clothes for you. I'm so looking forward to having a long girls' weekend with you!" "But this is crazy, I can't do this, I didn't mean for things to go this far, for God's sake Liz you can't be serious..." Suddenly she wasn't smiling any more, "I'm very serious Penny, I have said this before but your desire to play at being a girl has given me an opportunity to take charge of my life. That is an opportunity I fully intend to take. You will submit to me, and you will do everything that I tell you. Your role is to be my companion and not my husband. Real men don't wear dresses do they Penny?" "Well no, I suppose they don't," I replied "And men don't wear bras and panties, or stockings and high heels do they Penny?" "No Liz," I wasn't comfortable with the direction this was heading in.. "Oh, and of course men don't dress as maids to seduce the delivery guy - do they Penny?" She knew! Dammit she knew. "Men don't do any of those things do they Penny? Isn't it women who do those kind of things Penny?" I was finding it hard to disagree with her, she was using words to make me agree that I wasn't a man and I was so confused. It was at the moment that she reached out and took my little cock in her hand. She started gently stroking and it felt so good. "Stop resisting me Penny, you know how you want this. You love it when you dress up don't you Penny?" I wanted to say no but I could feel my little cock getting harder and harder as she caressed it. "And you want to wear a dress for me now don't you Penny, and you want to wear your highest heels so that we can go out and tease some sexy Spanish guys don't you Penny?" she continued to stroke me and I could feel myself building to a crescendo.. I knew that I shouldn't be letting this happen but I couldn't stop it, she was completely in control.. "Your Mistress told me what happened on Friday Penny, she told me how you allowed the delivery guy to sweep you off your feet and take you upstairs, did you know that she had filmed it all? She showed it to me on Friday night. I saw how you let him carry you to the bed Penny, I saw how you wrapped your legs around him as he climbed on top of you, I saw how passionately you kissed him, how you slipped down the bed and took him in your mouth. I saw how you made him come so quickly and how you took every last drop of cum from him Penny. I saw what a good girl you were Penny, you enjoyed pleasing him didn't you and you want to do it again don't you Penny, because you like being a girl don't you Penny?" She was stroking faster now and at that moment my little cock erupted in orgasmic convulsions. "Hah, I think we have our answer," Liz said triumphantly, "Penny, after all of this can you see how I would find it difficult to see you as a man," she said, "but I think it's wonderful that we seem to have similar taste in men, in fact I have to admit I was quite jealous watching you on that tape as the delivery guy had his way with you. Lucky girl!" "Now come on, that's enough talking for one night, Barcelona is a party town and I think that Penny and Liz should find a party!" "I'll help you with your make up..." she said as I realized that for tonight at least resistance was pointless. Liz seemed to be revelling in her new role as Queen of our little world. In all the time we had been together I had never seen her so energized and so obviously excited and amused by the power that she had over me. Confidence oozed through her. It didn't take long to get ready. Liz handed me some beautiful white underwear and a white linen dress, saying to me, "let's keep it simple tonight, it's your first time in public and it's probably best for you to wear something that doesn't draw too much attention." I was excited yet terrified as I pulled the stockings over my recently waxed legs. I stepped into a pair of summer sandals, brushed my hair and put on my now customary Alice band and stood back from the mirror, taking in the image before me. "Have you decided where we are going tonight?" I asked, "Do you really think that I can get away with this? Surely people will look at me and know?" Liz stepped towards me and put her hands on my shoulders, looking me in the eye as she said "Penny, you'll be fine. You haven't perfected the look yet but in this town there are different and interesting people in every bar in every street, you'll blend in just fine. As for tonight I thought we could start by having a drink in the bar and see how the mood takes us. Now come on, don't forget your lipstick, its time to go." We left the room and headed into the great unknown. As we stood waiting for the lift I was struck by how beautiful Liz was. She had an effortless elegance, wearing a pale green cashmere top and white cotton trousers she barely needed make up, and carried herself in a way that only seemed to highlight my clumsiness. "Don't worry," she said, obviously sensing my anxiety "you look great, just relax and allow the woman in you to come out... you know you want to." Another knowing smile, "and of course let's not forget that I have some very interesting tapes and photographs, it would be a shame if you refused to do as I say and I had to make them public wouldn't it Penny?!" There it was, the reminder that this was all non negotiable. We walked together, arm in arm to the bar on the ground floor of the hotel. Liz found us a table tucked away in the corner, and I sat with my back to the room as Liz ordered a bottle of champagne. "Oh waiter, would you bring three glasses please, we are expecting one more person to join us?" she said "What?!" I blurted, "what do you mean? You didn't say anything about us seeing anyone else, who is joining us?" "Oh, I'm sorry, I must have forgotten to tell you," she replied, "my sister Sally is in Barcelona this weekend with a group of girlfriends, she's going to have a drink with us before joining her friends for dinner later." "You must be joking! I can't see Sally, not dressed like this! I'll be humiliated. Please tell me that you are making this up!" At that precise moment Liz's sister, the beautiful blonde who I had always secretly fancied but never really got along with, arrived at our table and greeting Liz with a hug and a kiss turned to me and simply said "WOW". There was a brief pause, it seemed like an eternity as my heart rate went through the roof and I was convinced that I was a heartbeat away from fainting on the spot. "Oh my God, Liz you were telling the truth! I would never have believed it if I hadn't seen this with my own eyes. Of all the people in the world... I would never have guessed. I need a drink!" She was smiling as she spoke, in fact Liz was smiling too, suddenly I felt like I had again walked into a trap and hadn't seen it coming. "Sally meet Penny, Penny meet Sally," said Liz with a triumphant air. "Penny you have no idea how good it is to meet you," said Sally with an unmistakable smirk, "Liz told me that she found out that you like to dress up, but I didn't believe her when she said that you were so keen that you'd go out in public. Oh my God, you have even plucked your eyebrows, ooh and you've waxed your legs, Penny is well and truly out of the closet! Liz I really would never have guessed that your husband was gay, how do you cope with that!" "But I'm not gay." I'd barely got the words out when Liz interjected "To be honest Sally I was shocked and angry when I first found out, but after I'd thought about it for a while, I realized that it was a situation that I could turn to my advantage, and to be honest I have to admit that I've quite enjoyed seeing just how much control I have. You see once you understand that you are dealing with someone who might protest a little but in truth just adores being a woman and will do anything to be allowed to be a woman then the rest is plain sailing. Its only been a few weeks but the house has been signed over to me, the bank accounts are all in my name. Penny has agreed that I no longer have a husband and in order to stay in my house she accepts that she is my companion and housemaid." "Housemaid!" Sally could barely conceal her amusement, "Ooh please tell me that you've bought her a uniform." "But of course darling," Liz replied. They were giggling like schoolgirls and I was looking on in stunned silence. "But what about the day job? Surely even you wouldn't make 'Penny' go to the office." "Well I had thought about it, and it is tempting, but I have decided to speak with Penny's boss to see if she can work from home on a full time basis. I'm having lunch with him next week to discuss it." I couldn't believe my ears, my wife had arranged to meet my boss to persuade him to let me become a home worker and she had done this without telling me. They were talking about me as if I wasn't there. "So you are pretty serious about pushing on with Penny becoming a full time woman then?" "Well you know me, I see things in black and white, Penny loves being Penny and is actually a nicer person to be around than my ex husband so it seems to make sense for it to become 24/7. It also puts me in a position where I can get on with my life and do things that suit me, as and when I want to. It's a win win situation. I also have a friend who is a Dominatrix, she is whipping Penny into shape for me and is being very pushy about seeing just how far we can take the transformation." "Really , what does that mean?" Sally asked "It means that you should never mess with a dominatrix!" said Liz. "She wants to go the whole way with Penny and give her hormones, boobs, the works!" "Bloody hell, you can't do that can you, surely... can you?" Sally had a look of delight and sheer amazement on her face. "We'll see, to be honest I've been quite surprised by how Penny seems to have embraced all of this. She may claim not be gay but I can tell you that she likes her men to be big and strong, and is desperately keen to please." "You're kidding me!" "Its all on tape Sally, poor Penny didn't realize that she was being filmed. I've promised not to show the tape to anyone as long as she does as she is told." "How wonderful!" Sally was loving every second of this, "You must let me know how you get on, I hate to say it, but I have to leave now or I will be late to meet my girlfriends for dinner. I can't wait to tell them. I think a couple of them knew your husband before he/she became Penny, we'll have to see if we can arrange for us all to get together for a girls night out before we leave Barcelona! "Sounds like a great idea," said Liz, that triumphal air returning, "and of course I'm thinking that when Penny has completed her maid training she might have some spare time that can be utilized by hiring her out to work for friends or family. Do you think that might interest you?" "Ooh Liz, you read my mind!" Sally replied, "that would be such fun!" Maid training Liz has sent Penny on a residential maid training course in order to speed up her conditioning. She will be back to tell all soon. She's going to meet my boss. Liz wore a contented smile for several days after our return from Barcelona. It seemed that she hugely enjoyed exerting her control over me and every time that she tested me and came out on top it reinforced her enthusiasm for taking us both down this path. It had been only moments before we were due to leave our Barcelona hotel to go to the airport that she finally relented and gave me back my chinos so that I could make the journey in some male clothing. Even then I was forced to compromise as she gave me a tailored red silk top to wear as well. It was extremely feminine and I felt incredibly self conscious. Liz also seemed to find it highly entertaining to insist that I wore some fake pearls and a set of bra and panties underneath the top. "Liz I can't wear this, I'll look ridiculous, this top is obviously made for a woman and anyone who gets close to me will be able to see that I'm wearing a bra," I had protested. "Oh don't make such a fuss darling," Liz had replied, "It looks fine, and anyway given that you have been wandering around Barcelona wearing a collection of my summer dresses for the past few days you'll forgive me if I don't take your protests too seriously!" We arrived back in London in one piece although throughout the journey I felt the stares of strangers and heard whispered conversations and muffled laughter. On the plane the hostesses had taken it in turns to attend to us and were clearly amusing themselves by trying to work out whether I really was wearing a bra. I sat quietly, dazed and confused. Utterly humiliated at my plight yet incredibly excited as I cast my mind back to the memory of how it felt to spend three days as Penny. On Monday I returned to work, dressed in my male clothes and restored to my male persona. The day went as normal until late morning when my boss, Steve, called me into his office. "Your wife has called me and has asked to meet me for lunch later this week," he said, "what's it about?" "Err, I'm not sure," I replied rather hesitantly, "I think she wants to speak with you about the possibility of me working from home on a more regular basis." "So why do you need your wife to have that conversation with me?" was Steve's abrupt reply, "Who wears the trousers in your house?" I was trying to think of a way to answer that particular question when he continued, "I guess she probably just wants to meet me! All the women do in the end, they can't help themselves!" God he was so arrogant. He had an easy charm, which on occasion was quite attractive but he had incredible self confidence. I remembered having a drunken argument with him several months earlier, when he had insisted he could get any woman into bed if he put his mind to it. I'd told him that he was being ridiculous and was living in a fantasy world but he had just laughed at me. "Any woman is beddable my friend, you just have to work out what they want and then give it to them. I bet I could have your wife if I wanted to." I told him very forcefully that Liz wasn't that kind of girl and that she was far too choosy anyway. He just laughed at me, "Sure thing buddy, believe what you want to believe" That had been several months ago and now here we were in his office facing the prospect of him having lunch with my wife. I could tell what he was thinking and blurted out to him, "Steve there's no way that she'd ever be interested in you, she seeing you because she wants to see more of me!" "Oh so you remember our little conversation and you think that I'm not good enough for her do you?" "That's not what I meant, I just think that if you try it on with her you'll get nowhere." Steve's reply was instant, "You know I wasn't going to try it on with her, but now I feel compelled to. Shall we have a bet on it?" I replied saying that I thought that wasn't a good idea but Steve was rising to the challenge now and reminded me that I thought that he had no chance of success so what was there to lose in me agreeing to a bet? His logic was simple and straightforward. "I'll make it easy for you," he said, "shall we say Winner takes all! and if you agree to the bet then I will be much more likely to agree to Liz's request for you to do more homeworking when I see her." He went to his desk and began typing on the keyboard. He pressed the print key and passed the resulting sheet of paper over to me with a pen. It said in bold letters "I challenge you to sleep with my wife. If you are successful, I will pay you I probably should have paid more attention to the wording, but I signed the paper where he told me to. I thought it was all a macho charade and he would never follow through and if he did that he wouldn't succeed. Steve locked the paper in his office safe. "In case you are wondering I'm locking this away just in case I need it in the future, you see I fully intend to seduce your wife, I will take her to the point where she is begging me to fuck her, and when you complain or try to stop me I will be able to use this against you. In fact I may need your help and now that I have this piece of paper I will expect you to help me or face the consequence of having the document made public. I was stunned into silence, I'd allowed him to manipulate the situation so that it would appear that the whole thing was my idea. Steve then stood up as if to close our meeting and as he showed me to the door he said to me. "I've had another thought... just to make things interesting I'll call you when I've seen her. Don't answer your mobile. When I call I will allow the phone to ring once if she has agreed to see me again, twice if she has agreed to come to my apartment, three times when I kiss her passionately for the first time, and if it rings four times it's because I have just given her an orgasm." He was smiling but had a fiery look of determination in his eyes, I could see that he wanted to demonstrate his masculinity and his superiority to me. I left his office unsure of what I had started but certain that once again I had no control over what was going to happen. I got home from work that evening and found that the house was empty. Liz had left a note saying that she was meeting Sally for drinks and would be back later. I liked having the house to myself, it gave me an opportunity to relax and not have to worry too much about showing resistance to Liz about becoming Penny. I went upstairs to the bedroom and took off my suit and stepped into the shower. When I came out I sensed the emptiness of the house and as I was alone couldn't resist the temptation to become Penny again. She was becoming ever present in my life and gave me a feeling of relaxation and contentment that I couldn't find elsewhere.. A plain white silk blouse, a grey skirt, some very sheer stockings, black high heels and some lipstick and once again Penny stood before me in the mirror. I spent the next hour or so watching TV and drinking chilled white wine. I dozed off and was only woken by the sound of Liz's key in the front door. "Hi honey I'm home," Liz called as she came through the door, "and Sally has come back to pick up a book that I'm lending her." I sat bolt upright in shock, not again! At that moment they both walked into the room, only to stop in their tracks when they saw me. Liz was the first to speak, "Hah, do you see how things are Sally? As soon as she gets home she can't wait to get out of her work things and get dressed. I'm seriously thinking about throwing out the male clothes, they aren't being worn and they are just taking up space. So much for having a husband!" Sally was smiling as she said, "I know Liz, but she's so cute and once she's trained just think of all the household chores that she'll do for you. I think we need to find you a real man though, you have to start thinking about yourself." "Oh I'm not ready for that yet." replied Liz (did I hear correctly, did she use the word 'yet'?). At the moment I'm just trying to get used to having another woman in my house. And for all her faults I still love her, I'm beginning to see a side of her that I really like, a side that I never saw in my husband, life may be different, but now that I'm in control I think it will be better." Sally left and I went into the kitchen to fix Liz a drink. Liz followed me and as I was pouring her a glass of wine she moved closer to me and standing behind me put her hands around my waist gently holding me. "I love what you are wearing darling, and you are really beginning to develop a look that works for you. Look at us , you look gorgeous in that skirt and you have legs to die for! You look so glamorous and sexy and here I am wearing a pair of jeans and a sweater, this really is a role reversal! " It was a nice compliment and I thanked her because despite still feeling quite awkward in women's clothes, I did think I was becoming more convincing everyday and I was desperate to look good. She was running her hands over my skirt and feeling my stocking tops, "I think that you should always be Penny at home now darling... always..." my heart skipped a beat. "We both know that it's what you want." She was pulling me closer to her and I could feel she was becoming aroused.. "I'm feeling horny baby, do you think we should fuck?" Wow what a question! I hadn't been inside Liz for an age and was very definitely ready to make love with her. "Ooh yes, I'd love that," I replied breathlessly, "Good," she said, "I'll be back in a moment." Liz was gone for a moment or two and came back into the room with a large double ended dildo, and a tube of lubricant. She saw the look of surprise on my face. "Oh baby did you think that you were going to do the fucking? That's so silly, you know that only a real man could ever have me in that way. I made a purchase today and I think it may be fun. It's called a Feeldoe, it's actually made for lesbians to use on their lovers because they both get pleasure from it, it should be just fine for us. Mistress Grace is adamant that you should only have an orgasm when you have been penetrated, its all part of your conditioning, its all in your best interests, trust me!" She had her hands on me again, caressing me, kissing me, her touch felt so good, she slid her hands down the back of my skirt, pressing herself against me, "Turn round baby," she whispered into my ear. I didn't resist, I turned and with my back turned to her she ran her hands across the front of my body, feeling my bra through the silk blouse, "Bend over the desk baby," another whispered command. I leant forward, resting my hands on the desk. I could hear her unzipping her jeans and heard her sigh as she placed the bulbous end of the dildo inside her, "Oh baby I want you so much," she said to me as her hands gently lifted my skirt, exposing my stocking tops and my white panties, I felt the coldness of the gel on her finger as she prepared me to take her manhood and I gasped as she guided it into me, sliding it gently in and out, deeper and deeper, rhythmically stroking us both as she held me with her hands on my hips pulling me back onto her cock. I felt her shudder as she climaxed so quickly and she reached around me to feel the hardness of my own little cock. "You love it baby don't you? You love it when you have my cock inside you don't you? This is how girls like to come. You want to come don't you?" I came, and I came hard. It was the first time I had come in a long while and I could barely stand. Once more Liz had her now familiar air of triumph. I knew what she was doing. For her it wasn't just about me dressing as a woman, she was going to make me become one, and make me want everything that women want. Not only was I powerless to stop it, I secretly loved it. "By the way, I'm seeing your boss for lunch tomorrow, Steve is his name isn't it? What's he like?" Liz meets Steve I was sitting at my desk replying to some emails when my phone rang, it was Steve, my boss. "Your wife is in reception, go and get her and bring her to my office." It was a command that didn't invite discussion so I did as I was asked and went down to reception to meet Liz. I took her straight up to his office and after I had made the introductions he said "Look, I know we were supposed to have lunch today, but something has come up and I am tight for time, do you mind if we have the meeting in here?" Before I could say a word Liz smiled and said "Sure, I won't keep you too long, but if we are going to do this in the office do you mind if Penny sits in our meeting?" "Penny?" was Steve's immediate and slightly confused reply, "who's Penny?" Liz grimaced as she cast me a glance, mouthing the word "sorry" to me as she turned back to face Steve. "Sorry that was a slip of the tongue, but given that Penny is the reason we are having this meeting, it's probably for the best that you know sooner rather than later." "Know what?" Steve replied wearing an increasingly perplexed expression. He looked towards me hoping that I might help, but I just stood there in horrified, dumbstruck silence. Liz sat down before continuing, "Well it all started a little while ago when I got home one day earlier than expected only to find my husband wearing my clothes." "Wearing your clothes??" Steve edged forward on his chair as he spoke, suddenly very focussed on what Liz was saying. "Yes my clothes, a dress, my underwear, stockings, make up, the whole lot. I'm sure you can imagine that it was a massive shock to me. Steve's eyebrows seemed to have moved at least an in inch further up his forehead and he appeared to by finding it hard to suppress a smirk of delight. "Yes, that must have been terrible for you, but why are you telling me?" "Well after I had calmed down we had a long talk and it appears that my husband has a very strong desire to live as a woman. He asked me if I would refer to him as "she" at all times and has also changed his name to Penny. Penny never wears male clothing at home now, in fact she persuaded me to take her on a girls trip to Barcelona to do some shopping and spent the whole trip dressed as Penny. I found it very difficult, but am doing my best to be as understanding as possible. Penny has made it clear that she wants people to know about this, she insisted on surprising my sister by meeting her in public when fully dressed, its all been very difficult and very embarrassing for me, but I am trying to be as supportive as possible." I couldn't believe my ears, Liz was manipulating the truth in such a way as to make it seem that this was all my doing. Yes she had caught me trying on her clothes in a moment of boredom at home, but ever since that moment she had blackmailed me into dressing more regularly, it was she who had surprised me with meeting her sister, and it was she who had insisted that I work from home so that I could be Penny on a permanent basis, all so that she could be in total control! She continued to speak, "The one thing that Penny has been worried about - by the way I hope you don't mind if we all call her Penny from now on - was how you and your colleagues at the office would react. I said that I would come in and have a chat with you in order to persuade you to offer your support" "What kind of support do you have in mind?" said Steve, clearly revelling in this moment of revelation. "Well as Penny goes through her transition to becoming a full time woman I wondered if you would allow her to work from home on a more regular basis. Once she has adjusted and adapted to the course of hormone treatment that she will soon be starting I'm hopeful that you will allow her to return to a normal working environment" Transition! Hormones! This was all news to me... Steve adopted a very serious air, " We are an equal opportunities employer, Liz, and we are proud of our record of supporting minority groups..Penny will have all the support that she needs." As he turned towards me he smiled, it was a patronising smile of victory. He continued to speak, "I have to say Liz that I am very impressed by how supportive you are being. Not many women would be able to stand by their husbands in the face of such shocking revelations." "Thank you Steve, but in truth Penny has always been very loyal to me, and I feel it is the right thing to do." Steve frowned, he got up from his desk and went over to his office safe. Unlocking it he removed a piece of paper. What was he doing?! He spoke in a soft, measured tone, "Liz, I think that you should know that when I came in to work this morning I found this note on my desk, I'm sorry." He handed it to her. Oh my God... it was the note that Steve had typed up and had persuaded me to sign "I challenge you to sleep with my wife. If you are successful I will pay you Steve stepped over towards Liz and put a consoling hand on her shoulder "Liz, I'm sorry that I had to show you this but you have been so supportive and I think that it's important that you know what 'Penny' is up to. I hope that you can appreciate that I am not the kind of person, who could ever find this kind of macho game playing appropriate, but it's pretty clear that Penny is very confused and needs help." "is that all I'm worth to you?" Liz looked hurt and upset. "I didn't mean it like that," I was making a pathetic and utterly useless attempt to defend myself. Steve interrupted once more "Liz, I'm guessing that Penny (he couldn't say my new name without emphasizing the P) simply feels very guilty about the way you have been treated and what you have been put through. I suspect that this note was just a very clumsy way of encouraging me to show interest in you so that you could enjoy the company of a real man. Penny knows that I am 100% heterosexual and proud of that fact. Obviously she is very misguided in trying to make me force myself on you, that's not the kind of person that I am." He was manipulating her, I could see it but she couldn't! He was sowing seeds, telling her he was a 'real man' '100% heterosexual' and on top of that a caring thoughtful person. "Thanks Steve, I think you are being very generous to Penny in saying that, it's such a shock to see that note, I need to think about it and what effect it will have on my relationship with Penny in the future." She stood up to leave, I stood up at the same time but Steve told me to sit down and wait in his office. He escorted Liz back out to the reception area and came back 5 minutes later and resumed his position behind his desk. "Well Penny, what an interesting meeting that was!" he said in triumph, "all these years, I had no idea that you were a closet gay! How amusing." "Steve, it's really not like that..." He cut me short. "To be honest I don't really care. I find it quite amusing that you like to play at being a girl. However Liz may think that you are her sissy, but the reality is going to be quite different. From now on you will be MY little sissy fag. If you want to keep your job, you will do everything I say at all times, is that clear? If you fail I will do everything in my power to ensure that you never work in this industry again. You will be ruined. Have I made myself clear?" "Yes Steve," was my meek reply, I could sense that I was beaten and in no position to argue with him. "And never call me Steve again, from now on when you speak to me you will call me Master, is that understood?!" "Yes Master." I knew that Steve was a confident alpha male but I'd never seen this side of him before. He continued speaking, "It's no secret that I have always fancied your wife, and thanks to your complete stupidity I'm going to have her." "She doesn't know it yet, but I'm going to take my time and gently reel her in. Whilst you are prancing around dressing like a sissy I'm going to fuck her. I'm going to fuck her like she has never been fucked before and I'm going to do it in my office, in your house, in your bed, in the back of your car, I'm going to make her beg me to fuck her and I'm going to make sure that you know about every second of pleasure that I give her. Every time that I have fucked her I'm going to ring you so that you can thank me for giving her something that you never could. Just make sure that you leave your phone switched on. I'd hate for you to miss any updates." Later that day I arrived home, still trying to come to terms with how my world had changed so utterly in such a short time. It didn't seem so long ago that I was just a regular guy with an ordinary life, but how dramatically had everything changed when I'd made the fateful mistake of trying on my wife's clothes and getting caught. My wife had forced me to become more feminized and seemed to have no qualms about blackmailing me to accept more and more female conditioning. My boss now knew and had told the entire workforce that I was to be treated as a woman at all times. Worst of all it turned out that he was a lecherous bully and he was planning to take my place in the marital bed. I walked through the door to find Liz sitting in the kitchen drinking a glass of chilled white wine. she looked gorgeous and I found her as attractive in that moment as I always had. I knew that I owed her an apology for the note and immediately told her how sorry I was. She was surprisingly clam and just said to me. "Penny I've given it some thought and I think that Steve is probably right. You've been confused and given that you clearly can't offer me the things that only a real man can you got it into your head that you should persuade someone else that they should. Penny, you are a silly girl and you have made a mistake and I forgive you. I can appreciate that you see Steve as a very attractive and desirable man, but he has made it clear that he is not the kind of man, who pursues other peoples wives. He's too nice for that. For my part I still love you and am not the kind of woman, who would sleep with someone just because they are very good looking. Let's just regard the matter as closed." I knew that the matter wasn't closed but had no choice but to agree with her. "Oh and by the way we had a delivery today, I'd ordered some lingerie and sleepwear for you from Victoria's Secret. Look at this isn't it lovely? " She showed me a black babydoll, some sheer stockings, and some lace panties. "Be a good girl and try them on for me?" she said. I didn't want to, the reality of being a girl, the total lack of control that I had in my life and the realization that this wasn't a game, was sinking in very fast. I wanted to be Liz's husband again and to do things that men do for their wives but Liz had taken the opportunity to move on and it was all too late for me. Liz joined me in the bedroom as I tried on the new clothes. She beamed as she looked at me, "Oh Penny you really look such a temptress! If I ever let you out, the guys will just be queuing up for you!" I began to protest but she laughed and stepping closer to me slid her hand inside my panties. "Oh I can feel that someone is pleased with how today has gone!" Dressing up We had a quiet summer, carrying on in the pattern that had been established by Liz. She insisted that I spent large amounts of time as Penny and she was increasingly negative towards me whenever I returned to what had now become my male alter ego. A few weeks ago she came home early from work one day. She seemed to be in good spirits and carried with her various shopping bags. "Hey baby I decided to take the afternoon off and I went shopping with a girlfriend. I got a bit carried away in the lingerie department at Selfridges, I've got lots of things for us to try!" I wasn't sure that I wanted this, I was increasingly feeling a need to reassert my maleness and so I tried to dissuade her "Liz, I'm a bit tired today," I said, "do you mind if I take a look at some of this tomorrow?" She looked at me with a flash of defiance, "Hey I've gone to a lot of trouble for you today, now I suggest you pour a couple of glasses of wine and come upstairs with me... now!" I'd learnt that there wasn't much point in arguing with her when she was in this mood so yet again I did as I was told. Liz threw the bags on to the bed and started to rummage through her p