Making A Sissy Maid - Chapters 1-4 free porn video

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Chapter 1: Chris and Paige I guess I started withdrawing from my school friends at about the time my mother re-married and when I was about fourteen. My father had left two years before and we'd not heard from since. In that time I'd felt I'd got closer and closer to my mother, and we'd always been pretty close. We'd spend a lot of time together - playing games, talking about things, cooking, cleaning our small house in a less than fashionable suburb. We became like friends, I even started calling her by her name, Paige, and it seemed pretty normal to do that. So it was ok when Paige started going out again. I was fourteen and able to look after myself for a few hours on Friday or Saturday night. It also meant I could sit with her as she got ready. I really loved the intimacy of watching her dress and helping her chose what jewellery to wear. I guess somehow I was too caught up in watching her do her make up when dressed in lovely lingerie to think about the consequences of what she was off to do. I just liked to look at her still quite young body in black lace, in red satin and especially in black stockings. Sometimes I also used to sit up with her when Paige got back from her nights out - she never called them dates - and hear about the fun she had, where she went, who she met. It never sounded serious and she never really talked about any guy in particular. That is until she mentioned Dirk. Then really quickly, maybe over just three or four weeks, he was all she talked about. Suddenly it was just Dirk she went out with and these were dates. She said as much. And before I could get my head round this new man in her live she was enthusing about him and how I really needed to meet him. I really did not. And I really did not like the thought that all this dressing in sexy outfits and beautiful lingerie was for him, not me. But whether I liked it or not I was told loads about him. At first facts - he was older. Paige was actually quite young, still in her thirties, even though she most often dressed and behaved quite maturely. Dirk was however in his early fifties - although Paige insisted in great shape and looked much younger than he really was. He was pretty wealthy it seemed and owned a huge house in country - staying in his swish apartment in town when he dated my mother. He also had a daughter who, unbelievably to me, was almost my mother's age. Then gradually over the weeks and as the dates increased in regularity Paige moved on from facts about Dirk to her feelings for him. She came back quite late and quite tipsy one night. With a real flush on her face and giggling like a school girl gave me an update that I really did not want to hear about. She and Dirk had gone back to his apartment and 'made out'. That was her phrase. But even though she tried at first to keep her giggling update clean for my young ears she kept slipping in details. "Oh god, Chris, he was all over me," she gushed, "I felt so wanted and *giggles* god I wanted him too. I mean it's been at least two years." She sat on my bed as she told me this. I knew what she meant and had very mixed feelings. On one hand the closeness of my still sexy mother, now in a short satin dressing gown over her beautiful underwear, was so nice and it was strangely thrilling to hear what she had been up to with this man. On the other I felt excluded and not part of something huge in her life where before we'd shared everything. She leant forward almost shyly, her gown slipping open slightly to reveal more of a black lace and almost sheer bra and an edge of a nipple within the expensively embroidered cup. I tried not to stare but her breasts looked so lovely in that bra. "He just took me in his arms, oh god Chris, he just wanted me. I couldn't have stopped him - even if I'd wanted to!" Somehow this was exciting. I could feel my cock grow hard under the quilt as I sideways stared at Paige's lovely breast in that so sexy bra, cupped into a perfect mound. And her description of her evening with Dirk was actually exciting - I could not explain how. "He didn't speak, you know? He just kissed me and began to undo my buttons. Oh god Chris I almost jumped him right then," she giggled again, "but just managed to keep it together. Then, he seemed to throw my blouse and skirt off me and the next thing I knew he'd just picked me right up and carried me to his bed. I shouldn't be telling you all this but I really need to tell someone." Paige glanced at me and I nodded my ok, after all this was a hot story. "And then he was right on me. I just lay there and he did everything. I felt so womanly and so wanted." "He just peeled of my underwear. I don't remember undressing him but the next thing was naked on top of me. God he was so big! I just wrapped myself around him and held on while he made love to me. He was so strong and kept going for ages. He must be so fit. I lost track of time I guess but he must have gone on for half an hour or more. I was just so, you know, carried away!" I realised I'd got quite flushed and my erection was stiff as could be. I wanted to hear more and get more details. But my mother seemed to suddenly think about what she was doing with her son. She picked up my hand. "Chris, I think I really like him. I still love you and that's why I came straight back here. I want you to be sure you know that. But I really want to see more Dirk, you're ok with this?" What could I say? Paige had sat back up at that last statement and pulled her gown closed. She kissed my forehead and said goodnight and left. And I was left with a huge erection and a mind full of images of this stranger fucking my mother. This stranger with a huge cock, compared to my own not very large peenie. This stranger as he ploughed his huge cock into my mother's pussy as she moaned and groaned in ecstasy. I came in large thick spurts into my hand and fell asleep. Chapter 2: Paige and Dirk Paige and Dirk were to get married that November. It was to be a pretty quiet event, really just my mother and me and Dirk and his daughter. Eve was a surprise. I first met her just one month before the wedding. In fact, it all happened so quickly that I had really only met Dirk maybe four times before the wedding. Eve was clearly a strong woman. She was almost my mother's age but if anything looked a little older. She was tall and statuesque - strong limbed but not at all over-weight. But it was not so much her build that struck you when you first saw her as her dress and style. I almost choked in surprise when I first met this goddess in satin in Dirk's large west end apartment. She worked in some private school as the head mistress and I guessed she was still in her work clothes. Later I discovered she only wore work clothes. She turned as Paige and I entered the room, smiled briefly at Paige and turned to me and held out her hand. It was a perfectly manicured hand with dark ruby nail varnish and large jewelled rings on two fingers. This perfectly shaped hand rose out from a crisp white satin blouse with a heavy silver bracelet slipping down from her wrist. The blouse had deep cuffs and surprisingly full cut on the sleeves. As I took her hand in a short hand shake my eyes travelled along the sheer white sleeve to her collar, and a black satin choker round her neck, with much up effort up to meet her gaze. "So this is Chris, how lovely," she purred. I mean, really this was a purr. I could not tell if this was the purr of pleasure or a purr like a big cat about to pounce. I immediately blushed furiously and mumbled some sort of hello. "Oh how lovely, you're quite shy." Eve laughed, not at me so much as with everyone else. There was a little slightly awkward laugh from Paige and Dirk. "He's not usually this shy," Paige said, no doubt trying to help me out but in fact establishing the state that these three adults could talk about me, right in front of me, as if I was not here at all. I just stood blushing while they carried on discussing me. "He can be quite quiet though at times. Since his father, you know, passed away." "Oh I think it is really sweet when a boy it a little shy," said Eve, "much better than those rather rowdy boys that seem to be so common these days. No I do prefer the more sensitive ones." As she spoke she looked me up and down. Not that there is much too look at I guess as I'm not the tallest kid and little weedy still. I almost squirmed under her inspection. I sorted of mumbled a thank you, not sure if that was what I was meant to say. Eve just smiled and the adults continued the conversation. I sat in a huge arm chair for the rest of the afternoon, sipping a glass of lemonade, and basically just watching. I watched Paige, who looked very, very smart and sophisticated. She had dressed up as smartly and sexily as she did for every meeting she had with Dirk. By now I knew pretty much all of her outfits and sets of underwear and I knew exactly what she was wearing today as I'd helped her chose the underwear and the dress. This ritual of me helping my mother dress was quickly becoming a favourite time together. I loved it when she held out two or three different bras and looked at me "which one honey?" I'd no idea as I loved the look of all of her bras and just randomly picked one - often the laciest. She looked so sexy in lacy underwear that this seemed the best choice. Then she'd pick up the matching set, Paige almost always wore suspender belt and stockings as well the bra and panties, and slipped into her en suite to change into them. Then she was come out looking so, so sexy and sit on the edge of the bed to slip on her stockings. We would chat about school and stuff but really I was watching her dress with awe and excitement. Earlier today we'd sat there and I'd chosen a particularly sexy pale cream outfit with a slightly long line bra, almost like a bustier, and french knickers that came with suspenders fitted. She wore beige stockings and a full lacy slip. It was so hard not to reach out to stroke the beautiful soft satin and lace. She slipped on a lovely dress over the top and sat down again. "Chris, would you be a dear and help me?" She did not really need to ask as I knew exactly what she now wanted. "Can you just grab those white pumps and slip them onto my feet please? I can't ever seem to get the straps right..." I was only my knees in front of her like a shot. I'd already figured she would want to wear the high heel white pumps and had spotted them by her dresser. I grabbed them and then kneeling in front of her gently raised on foot by her ankle and slipped her foot into the shoe. This was almost like a ritual and done in silence. Just the slight rasp of the shoe leather against her sheer stockings and the almost audible 'swumph' as her heel slid into place in the shoe. I reluctantly let go of her ankle, 'accidentally' stroking the fine fabric of her stocking as I did, and put her foot into my lap. I then buckled the thin strap round her ankle. This was repeated for the other foot. This ritual always caused me to get so very hard. Once both shoes were on I just could not stand up in front of my mother as my cock was now straining in my trousers. So every time Paige would give a smile and stand up to cross over to her dresser, leaving me stuck on the floor. I'd stay there while she did her make up. As I gazed at Paige and recalled the eroticism of today's dressing session with my mother, my eye was caught by Eve. She was staring right at me even though she was carrying on the conversation with Dirk and Paige. She had definitely caught me gazing lovingly at my mother and her lovely outfit. She slightly raised an eyebrow as she looked directly at me. I blushed again. I could tell she just knew, just knew that I had been helping my mother dress and helping my mother chose her lingerie. Her look made me think that she suspected even more. Embarrassed I glanced away and pretended to look round the room. "Chris," she said to me, "Chris, do you want to see the rest of daddy's apartment? You seem a bit bored here. I can show you round and we can see if we can be friends." "Emm, yeah, ok," was all I could think to say. Paige immediately told us that this was a great idea - she was clearly very anxious the Eve and I got on. Eve stood and opened the lounge door and I followed. She kept a running commentary going all round the apartment: the kitchen, the dining room, the games room, the study, the 5 bedrooms, the huge main bathroom, the balcony. This was a seriously expensive place. And it was hard not to be impressed and wish you could live here. At the last room Eve hesitated before opening the door. "And this is just my room, nothing much to see here." She pulled back an inch as if she thought better of opening the door. I really wanted to see her room. As she had led me round the apartment I had watched her as much as look at the rooms and the d?cor. The tight black satin skirt she wore was difficult to ignore - especially with her fine round buttocks. As she sashayed from room to room I followed, my eyes glued to that incredibly sexy rump. And on one occasion the crisp white blouse had become almost transparent with the light from a window behind Eve and the clear outline of a full breast, shaped by expensive lingerie, was revealed as she pointed to some architectural feature. I wanted to see where a goddess like this slept. "We might as well," I said perhaps too quickly, "you know, finish the tour." "It is only my room and I'm afraid probably a little messy." "I'm not bothered by mess," I said surprised that this beautifully presented woman would ever be untidy. "And I'd love to see your room, you know, to get to know you better." Eve stood for a second and looked at me. She smiled. "Why, if you really do want to see my boudoir then you must. I would not want to deprive you of this." Every word she said felt loaded with innuendo and meaning. She held the door open for me and flicked on the lights as the room was surprisingly dark. I almost gasped out loud; I think I might have even let out a little 'oh'. This was a fabulous and sumptuous room. This was definitely a boudoir not just a bedroom. It was dark in colour and the heavily draped curtains and almost opaque nets over the windows meant there seemed to be little natural light. But it was not gloomy. The many low level lights gave it a warm, heady feel. It was sexy but in a rich, decadent way. The furniture was dark and old fashioned and almost every item had some piece of clothing draped over it or hanging out from a drawer or hung carelessly off a half open door. And when I say 'clothing' I mean underwear. Stockings, slips, bras, panties, suspender belts, even a very full looking petticoat lay on the seat of ruby red chair. I was probably drooling. I certainly was silent as I walked dream like into her bedroom and took in all the fabulous lingerie on display - imagining what other beautiful items she had that were still hidden in drawers and wardrobes. I suddenly realised that I had walked right up to that petticoat on the chair, and had half picked it up to feel the lovely satiny texture and stroke the lacy edging. I heard Eve laugh softly. "Do you like my room then?" I dropped the petticoat and blushed crimson. Unable to answer. "I can see you like my undies," she came up to me, "but then I suspected that you might." "They're very lovely." I could not lie or even pretend that I was not fascinated. "I knew you would like them. I love beautiful lingerie too. Please, don't be shy, have a proper look. See, this is one of my favourite bras; its silk and just a lovely shade of blue." Eve held out a sumptuous and sexy bra to me. I took it from her and admired the design and the material - it was sexy and very, very feminine. I stroked the soft silk fabric with my fingers and then on impulse stroked it against my cheek. Again Eve laughed. "Oh, Chris you really do like this sort of lady's underwear, don't you?" I just nodded. "I know you did. I'd heard about you from Paige and seen a picture of you. I just knew you loved lingerie. You like to help Paige dress don't you?" Again I just nodded, stroking the silky bra. "And you like to put on sexy undies as well. I'm not wrong am I?" I began to cry quietly. I'd never told anyone this. It was my one secret from Paige, something I felt was somehow wrong and not something I could tell her. But equally I just could not lie to Eve or even pretend that she was wrong. "Oh little Chris, don't cry like a sissy. I don't think you are bad for wanting to try on lovely lingerie. I am not angry with you. And I won't tell anyone unless you want me to. Do you?" "No, no. Please don't tell Paige or Dirk, please. I'd die of embarrassment. No-one knows, please Eve." I was suddenly quite afraid, what might Eve do? She smiled. "Chris, shh. There is no need to worry. It's just our little secret. I won't tell. You and I can keep this secret together - like very close friends." I looked up at her. She was being so nice and yet the look in her eyes made me think that I should not be too happy about this arrangement. Chapter 3: Eve and Chris I got a surprise call from Eve about a week after I first met her. I knew that Paige was round with Dirk but I had not realised that Eve would be with them. She told me that the next day, it being Friday, our two parents were going to go off for a weekend together. They'd only just decided and that they had asked Eve if she would look after me and keep me company. She didn't say baby-sit but the tone in her voice said as much. "What all weekend?" I asked. I was hugely surprised that Paige had not asked me first; she never even went out for an evening without checking with me. "It seems so, Chris. They just thought a weekend away would be best before they commit to each other. It was just decided at lunch today. So, is this ok with you?" I could almost hear a superior tone in her voice, that it was her and not Paige asking me. "I guess, what, at your apartment?" "Well there's a whole games room and lots more space. It'll be fun." So that was that. Paige came back that evening and was so nice to me. She hugged me and thanked me for being so understanding and willing to help her out. It was almost as if she hadn't been certain that I'd be willing to stay with Eve and let her and Dirk head off for the weekend. But it was already agreed and Paige was clearly excited as she packed for their trip. When she went to her underwear drawers, she turned to me and asked "what do you think I need for this weekend? We're going to a luxury hotel in the city and I'm guessing we'll be eating out in some pretty fancy places." I walked over to her to help. "Paige, this will call for some of your best lingerie. Perhaps the pale blue set and your cream basque." Suddenly I realised that I'd made a big mistake. The basque was new. She'd only bought the previous week and she'd never shown it to me. I only knew about it from one of my many explorations of her underwear drawers. Two days ago when Paige was out with Dirk one afternoon I had opened the bottom drawer to find the basque still in its packaging. This was so annoying because as soon as I saw it I knew I wanted to see it properly and even to try it on. However, any visible sign that the packaging had been opened would be risking too much. Paige gave me a funny look but did not say anything. She took out the basque, still in its pack, and the bra, panties and suspender set in blue plus other items. I noticed that all of the pieces of lingerie she took were her sexiest. I was so jealous but not completely sure if I was jealous of her or of Dirk. The next day Paige drove me to Dirk's apartment where as soon as we got there, she and Dirk headed off. I was left with Eve standing behind me in the doorway of the apartment. "Come in little Chris." Eve walked back into the apartment. "We've so much to do over this weekend." She walked to her bedroom and I followed. Just following her was a dream. She wore a tight black satin skirt, a very fitted white blouse and very high heels in patent leather. Her bottom wiggled seductively as she walked. Once I was inside she turned round. "Strip sissy boy." Her voice was very commanding and I only hesitated for a second. "I said strip, now do it." I immediately pulled all my clothes off. Eve walked round me, checking out my body. "You are a very slight little boy, Chrissie. Yes, a very slender sissy boy. Now all we need is to tidy up some hairy bits on your legs and you'll be perfect." "What do you mean?" I asked, getting nervous. "I mean little Chrissie that if we are to dress you like the sissy boy- girl that you are then we need to shave your legs and trim your pubes. You are very feminine already but even though most of your hairs are fair and fine they need to go. Follow me into my en suite" Once in her bathroom she produced a can of shaving cream and covered my legs and crotch with foam. She then took a lady-shave and deftly shaved my shins of all their hair, not that there was much and I'd no hair on my thighs, apart from a few pubes at the very top. These she quickly removed and set about my pubic thatch proper. I did not have a very hairy bush but Eve trimmed them all shorter and removed all but a little strip in the middle. "There, a perfect little landing strip, you little hussy," Eve laughed as she washed away the foam and the hairs. She then quickly dried my legs with a soft pink towel and led me into the bedroom again. "Now Chrissie, we've not really had a chance to talk about this have we? But I'm sure that you want this as much as I want it. You do know what I'm talking about? Yes, you do. Now let's get started shall we?" Eve led me over to her bed and sat me down. She then went over to one of her many chests of drawers and pulled open a middle drawer. She took out what looked like very lacy, very frilly pink panties and a matching bra. She then opened another drawer and took out what looked like a pale pink basque, rolled up. And then she picked up a packet of stockings from the top of the chest. She turned and stood in front of me. "You dress in your mother's undies, don't you Chrissie?" I blushed deep red and mumbled something about having only done that once or twice. I was stunned when she slapped be brusquely across the face, not hard but sharp enough. "Do not lie to me sissy," she hissed and sounded furious with real threatening edge to her voice, "tell me the truth" "Yes Eve," I said quietly, "I love to wear Paige's lingerie. I love the feel of the silks and satins and I love walking round the house in stockings. I'm sorry" "And you love being a sissy, don't you Chrissie?" "Yes, I love being all girly and sissy" "That's better." Suddenly Eve was calm again. "I think you'll make a lovely little sissy girl. Now let's get you dressed and see what you look like." She dressed me quickly and efficiently. It dawned on me that Eve had done this before - and not just dressed herself. She'd clearly dressed someone else before and knew exactly what to do. She lifted my left leg and rolled a seamed stocking up my leg, and then repeated it on the other leg. These were deliciously fine pale tan stockings with a fully fitted feet and deep lace tops. Them she stood me up and slipped the bra over my arms. She fastened it at the back, quite tightly and straightened the straps. She then fixed the suspender belt round my waist and clipped the six suspenders to the stocking tops. Finally she had me step into the panties and she pulled them up my legs and snugged them in place. She stood back and looked at me. I also checked my lovely new lingerie. The pink lace was just beautiful, especially on the cups of the bra and the front of the panties. The suspender belt was very deep with slight boning. The back of the panties were covered in seven or eight fine layers of frilly lace - these covered my bottom in a particularly sissy way. "This is much better, isn't it?" Eve stroked my thighs and bottom as she walked round me. "But your bust needs to be enhanced, let's pop these little foam breasts into the cups of your bra." She slipped the fake breasts into the cups and I had a lovely full C cup bust. The fake breasts were very realistic with hard little nipples and weighed more than the foam so they felt very real. "Now let's give you a proper girly shape, "she picked up the item I had thought was a basque and unrolled it. It clear to me now this piece of pink satin was a short corset or waist cincher. I'd seen pictures of these and fantasised about what they would be like to wear. Here suddenly I was going to be dressed in one. "I'll just slip this round your waist, oh yes, this is going to fit beautifully. Now if you can fasten those clasps at the front, Chrissie." I felt a little thrill as I did up the clasps - partly due to the feeling of the corset as it pressed all around me and partly from Eve calling me by such a girly name. As soon as the five metal clasps were properly done up Eve started tugging on the laces at the back. "Now we need to pull in from the top and the bottom. Maybe you need to hold onto something as this may take a little pulling first time round." I did not miss the implication of Eve saying first time round - this dressing game was definitely not a one off in Eve's mind. I reached out to the nearest bed post of her sumptuous four poster as Eve started pulling harder on the corset cords. She systematically tugged loops from the top and the bottom of the corset, each time pulling the rigid satin tighter and tighter. Then when she had both lengths pulled out at the middle part of the lacing she told me to hold on as she put a surprising effort into a couple of hard tugs. I gasped at each pull. "God, Eve, that's too tight, that's hurting!" "Don't be silly little sissy. Of course it's tight. Look what a lovely shape this gives you. You'll get used to the tightness and you'll love your new curves so much you will soon forget about any little hurting." Right enough this lovely pink satin corset pulled me in fantastically well. I had a proper waist - goodness knows how much Eve had pulled me in from my normal slender 28 inches. Maybe as much as 5 or 6 inches. I breathed lightly and a little light headedly as I got used to the constant pressure of the corset. "Oh yes, that's much better. We are going to get you all made up now." Eve took my hand and led me over to her dressing table. I sat in front of the mirror and the rows and rows of cosmetics, very aware of how upright the stiff corset made me. "Now you do have a lovely posture with this corset on. Yes, just place your hands on your lap like a little sissy and let me sort out your make up. Something quite light and pink and girly I think..." Eve set to work, smoothing on a light foundation, brushing on a little dark pink blusher and then carefully making up my eyes. I sat as if in a daze - just loving the soft and gentle attention. Lastly Eve took a tube of very pink lip gloss and slowly coated my lips with a sweet smelling and very sensuous looking coating. Looking in the mirror I saw myself as a very girly girl, hardly a sign of maleness to my made up face and oh so sexy little body. "Oh my goodness, Eve, you've made me so lovely. Oh thank you so much." "I'm not quite finished my little Chrissie. I've this lovely long blonde wig and that will finish your look." She pulled a very full looking wig from a box on the floor and pulled it into position on my head. Then she deftly brushed the wig out into a very feminine shape - the long blonde hairs cascading over my shoulders. I was speechless as I admired myself in the mirror. I stood up and Eve led me to a full length mirror across the room. I twirled and preened and admired myself from every angle. The whole look was so pink and feminine - girly on a woman; sissy on me. "Oh thank you Eve. I look to lovely. I've never been able to make myself look so pretty. This is just incredible and my lingerie feels so unbelievable." "Step into these shoes, Chrissie. They are going to be about as high as you can probably cope with - I'd ideally prefer something at about six or more inches on the heel, but these will do." Eve held a pair of high heel white pumps - the heel looked plenty high to me. She knelt down in front of me and slipped each of my feet into the shoes. I had to hold onto the frame of the mirror to stop from losing my balance. "This is the last time I'll be on my knees for you Chrissie. But we need to get these straps done up and with your corset you would not manage to reach." I had not even thought of that as I felt Eve tighten the ankle strap of the left shoe. As she fastened the buckle I heard a faint 'click'. I glanced down as Eve fastened the strap on the right shoe - just too late to see the tiny padlock on that side also click shut. Eve stood up and look me in the eye. I glanced away, suddenly feeling vey vulnerable. "Yes, they locked on Chrissie, so you don't get lazy and try to kick them off. You are locked into your shoes." Eve smiled at me as I simpered in front of her. This was a little bit scary but also a lot exciting. "How does it make you feel? Do you feel trapped, my dear? And do you feel girly?" "Oh, yes, yes Eve," I gushed, letting my voice rise to more feminine level. "And do you feel very sissy, Chrissie?" I twirled around in front of her. "Yes, very sissy. I mean look at how pretty and pink and sissy I look!" Eve smiled and took my hand. "Then you need one final thing. I dressed you up so you could be my sissy maid for the weekend. And you've just agreed you are the most sissy thing ever - so let's get you into a pretty little maids outfit!!" I hesitated and Eve had to pull me towards her huge wardrobe. "You will just love this sissy maid's dress Chrissie. This pretty lacy dress is everything you've dreamed of." Her words took away any doubt in my mind and as she reached into the wardrobe I leaned forward to see what the dress looked like. It did not disappoint and Eve was right. This was a most sissy dress. It was a dream of satin and lace. Layers of frilly lace covered a blush pink satin, with satin bows of bright pink and deep frothing of white lace across every edge - the sleeves, the neck line and the skirt. It was almost a sissy party dress, almost a maid's dress. First she had me slip a frothy crinoline petticoat on. It's satin top billowed out into a mass of pale pink lacing. I could feel the soft lace and satin run softly against my stockings. Its was lovely and it would make the sissy dress so dreamy. Eve carefully pulled the dress down over me. I slipped my arms into the puffy sleeves and stoked the dress into place. Eve zipped it up at the back and the zip came right up to the top of the lacy neck collar. This lace collar closely covered my neck almost to my jaw. I distinctly heard another 'click' and the tug on the neck made me sure Eve had padlocked my dress onto me. Eve sorted the way the dress lay over the petticoat until she was happy with the way it sat. She held me by the shoulders and turned me to face the mirror. I gasped out loud. I was a perfect sissy this lovely frilly dress of pink. As I just stared at my sissy reflection Eve tied a white satin apron round my waist, tying a big satin bow at my back. "You are my sissy maid now, Chrissie," she said in satisfaction. Chapter 4: Eve and her maid "Oh yes I am," I whispered, "I'm your little sissy maid!" I had no idea what I had let myself in for but the thought was just so exciting. "Do you promise, Chrissie? Do you promise to be my sissy maid for this weekend?" Eve watched me admire myself in the mirror. "Oh yes please, Eve." I nodded enthusiastically. I could not believe all this had happened to me. How incredibly lucky it seemed to have met Eve and for her to have turned out to be so lovely and thoughtful. It really was like a dream come true - more than that. In my wildest dreams I would not have thought of ending up dressed and made up so beautifully. Eve smiled. If I'd been watching her rather than staring at my lovely dress from every possible angle I might have noticed a cruel twist to that smile. But instead I was looking at every detail on the dress - the little bows that circled the hem, the lace details over the bodice, the cascading lace from the puff sleeves that covered my elbows. "And as my sissy maid," Eve leaned towards me, still holding my shoulders," you'll do everything I ask of you?" "Of course I will, I'll be the best maid you ever had." "And you do know that if you disappoint me you may need to be corrected?" "Oh Eve, I'll not disappoint you, I'll be the most obedient little sissy maid you ever had!" I was gushing my promises in a lisping voice - feeling every inch a girly sissy. "And you know that if you do not obey me and carry out my orders then I will have to tell Paige about you!" This threat seemed so unnecessary and so unexpected. It made me turn from my reflection and look at Eve. "Why would you do that? I thought we were friends?" "Well then let's make sure there is no need to tell Paige anything. All you need to do is obey my instructions and do as you are told." "But of course I will, Eve. I'm your sissy maid and it's my job to do as you ask." I smiled and hugged myself. "What can I do for you right now?" "Well, you can get me supper. Come, I'll show you where everything is in the kitchen. You'll need to know if you are to be my maid for the weekend!" She led me through the apartment. I struggled to keep up in my high heel shoes. I kept off balancing and almost fell a couple of times. But the feeling of the flouncing petticoats and the rustle of my stockings was just exhilarating. And when we got to the kitchen with its tiled floor and I heard the unmistakable clicking of my heels on the floor I almost swooned. I was the most girly sissy ever. Eve quickly told me what she wanted - a salad and pate with white wine - and told me where everything was. She was impatient when I got confused and exasperated when I did not know which of the white wines to pour. But eventually I got everything together and followed her with her supper on a tray through to the dining room. She sat imperiously as I laid out her meal in front of her. She examined the plate, the cutlery and the napkin - at least I'd remembered that. "Chrissie, that was very poor but I cannot wait any longer. This standard will most certainly improve over the weekend. I will help you by pointing out your mistakes and you had better pay attention. I will also help you by punishing poor work. This punishment is for your good - do you understand?" I nodded, "Yes miss." Eve smiled. "Good girl. That's exactly the attitude I want. We will punish after I have eaten my supper. Please pass me my magazine from the sitting room and then wait in the corner for me." I swished through to the next room, getting a little better in my heels, or at least a bit less unbalanced. I found a copy of Vogue open on a low table and tried to bend to pick it up. Suddenly I realised just how tight and restrictive my corset really was. There was just no bending at the waist. I dipped my knees in a little curtsey like move and reached down to pick up the magazine. "How very feminine!" I thought and smiled to myself. I swished back to Eve in the dining room and carefully held out the magazine for her to take. She did so rather brusquely and stared at me - dashing my happy thoughts. "Chrissie, I told you, get into the corner while I eat. I do not want you gawping at me." I turned to the nearest corner. "That's it, hands clasped behind your back so I can see them, head up straight, back straight, toes straight...and no fidgeting." I stood as still as I could, and kept my eyes fixed onto the corner of the room as I listened to the tinkle of Eve's cutlery and the occasional glossy page being turned. I was very aware of the uncomfortable height of my heels and kept having to shift my weight from one foot to the other. I was also very aware of the lovely softness of my pretty satin dress and its fluffy petticoats and could barely keep my hands from stroking it. On top of all that I was very aware of my tight corset and my new large breasts pushing against my dress and this thrill made me so breathless I was almost panting. I lost track of time and closed my eyes as I let the feelings of femininity take over me. I was in a daze of feeling when out of nowhere Eve came up behind me and grabbed my neck in a painful grip. She was clearly furiously angry, and I was completely taken by surprise. "You useless little sissy slut!" Eve spat, "What did I tell you?" "To stand in the corner, miss, like I did miss." My pleadings were pathetic. "To stand straight and not to move, you little tramp!" Eve leant close to my ear. "But oh no, even a simple instruction like that is too difficult for little sissy Chrissie. So I have to put up with moaning and your simpering and your disgusting self caresses." "I didn't realise, miss," I was almost sobbing, "I'll try harder, please." "Not good enough," Eve stated. "You were already due some punishment and this sort of insolence will mean we can help you out with proper punishment. I had been thinking about a little spanking to introduce you to the pleasures of correction. Your inability to follow even simple directions means we can go further than just a light spanking. Oh yes, much further!" She dragged me by the scruff of the neck through to her bedroom and practically threw me over the ottoman at the base of her bed. I collapsed over the ottoman with my face falling into the deep quilt on her bed and my knees on the floor. Before I could even think or work out what was happening Eve had grabbed one hand and then the other, stretching my arms out to my sides. It was only when I tried to move my arms that I realized that she had tied my wrists to the bed posts. "Right little missy sissy, remember this is all for your own good. This is to make you a better sissy maid." I think I just whimpered in fright at that. My face was still in the silk covered deep quilt on her bed and I could not see what Eve was doing being me. I felt my petticoats and dress being lifted from my bottom and pressed down onto my back. I felt a hand pull my knickers up and tightly pulled between my ass cheeks, exposing my white buttocks. I felt a hand caress my bottom. And then nothing. I was breathing heavily into the quilt, almost sobbing, and this muffled the sounds around me. I could not really here what Eve was doing and she had stopped touching me. I waited for minutes trying to slow my breathing. Whack! My whole body lifted from the bed and fell back. I gasped and cried out "my god, ouch! Eve! Arghh!" Whack again. Eve must have been using a paddle or strap to whip me. The shock was incredible and then through the shock the pain on my buttocks. "Well, Chrissie, count them!" Eve told me and unleashed another loud slap on my poor bottom. "Ow, ow!" I sobbed, "two, no three, please miss! That's enough!" I heard laugh as yet another stroke of the strap cut across my butt cheeks. "Two you think?" "No, three now miss, please." My pathetic pleadings were met by three hard slaps in quick succession. "Four, five, six, miss." Eve now stroked my raw bottom with her hand. "There now, this is not so bad. Is it? Now you know what a little punishment feels like ... what do you say?" "Thank you miss Eve," I said instinctively. "Good girl." Eve pulled my knickers back into place and pulled down my dress and petticoat. "Now stand up, you need to get back to being my maid, remember?" I stood in front of Eve, very aware of my stinging bottom, and tried a little curtsey. Eve smiled. "How very sweet. Now you must do something to please your mistress - do you think you can do this?" I nodded, not sure how much to commit myself. Eve smiled again and I noticed she was gently caressing her legs. She had pulled her tight skirt up quite far and was stroking her thighs. Now she twisted round to unzip the skirt and lifted her bottom to slide the skirt down her legs and off. She sat back in her stocking legs and carelessly kicked the skirt across the room. Her hands went back to her lovely thighs and she ran her finger-tips around the deep lace tops of her black stockings. She looked up at me as she slipped her hands between her thighs and ran them down to her knees as she slowly spread her legs apart. I almost gasped out loud as her perfectly trimmed, beautifully shaped pussy was revealed to me. "I never wear panties. Only sissies wear panties. I like to be free and accessible. Especially when I'm as hot and wet as I am now. Do you like what you see?" I could only nod. This was a vision of heaven for me - the much dreamed of but never seen holy grail. I couldn't even take my eyes off her lovely pussy. "Good. Then you need to worship my pussy, sissy. You need to get down onto your knees and pay the deepest, deepest respect to my womanhood." I did. I almost dived down in front of Eve, my little frilly skirt and petticoat puffing up round my waist as I fell onto my knees. Eve parted her legs further as I leant in to her crotch. I just knew what she wanted me to do - to kiss and lick her pussy. And I was desperate to do just that. I'd read about this and fantasised about this. I just did not know what I was actually going to do. The first thing that struck me was her powerful, deep female smell. The second thing was that her pussy lips, revealed beneath her delicate and expertly trimmed tiny fluff of a bush, were moist - almost dripping. I clumsily planted a full lip kiss on her bush. Hesitated then ran my tongue from the edge of her lips up across her fluff of hair. Above me I heard Eve laugh. "Oh my god, you really have no idea. How perfect. We will have such fun educating you. Now, get your dainty little tongue right down deep into my pussy!" Over the next hour Eve instructed me in exactly how to pleasure her with my mouth and tongue. My neck and tongue ached after barely twenty minutes but she demanded that I kept going. I licked her pussy until my tongue felt raw, I deeply kissed her mound until my face was dripping with her juices, I nibbled and tweaked her clit until my neck got a crick. Then when I felt I could hardly keep going she fell back onto the bed and brought her legs up into the air to present her tight puckered hole. I was made to kiss and tongue and worship her arse hole. And I did, I drove my tongue deep into her anus and felt the deep, deep shame and thrill of knowing I was Eve's arse-licking sissy. Forever.

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Making a Sissy 2

Making a Sissy By Jena Corso Edited by Angela Meyers Chapter Two Justin's legs were like jelly as Lynne dragged him down the stairs by the hand with Janine following right behind her. As they stopped in the foyer, he stood shivering as his girlfriend quickly stripped down to her bra and panties before neatly folding her clothes and taking the suit from the hallway closet. In a second she had changed into her sister's white silk blouse and fitted suit before quickly opening their...

2 years ago
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Making a Sissy 1

Making a Sissy By Jena Corso Edited by Angela Meyers Chapter One "Aunt Lynne, I really have to go," said Tommy, racing over holding himself. "Like really bad." "So can you take him, honey?" Lynne asked. "Really?" Justin replied, leaning back. "I just got comfortable." "Seriously? You are so F--. I mean so lazy," said Lynne, shaking her head. "Now come on, the little guy is just learning and doing really good potty training already, so it's just a swim diaper you need to...

3 years ago
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Making of My Sissy Part 3

One day I was home to see, first hand, how my sissy's day progressed. The day went as I thought it would, well planned and a perfect schedule to keep my little one busy. Then there was a knock at the door. My sissy never went near the door. I watched as the bell rang. Again my sissy never even looked at the door. I asked him if there was something wrong. He said that he doesn't answer the door when dressed as such. I asked "dressed as what?" "This is what you liked and you agreed that you would...

4 years ago
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Making of My Sissy Part Two

It was then that I pursued my own physical satisfaction from a former lover and co-worker of mine. I always had a thing for black men since most of my life I worked around blacks. It was many years prior to my marriage that I was dating a fellow co-worker, who happened to be black. Everyone at work knew we were dating. Then I met my husband and the dating had stopped and I devoted my life towards my new love. Finding out that my hubby enjoyed playing as a gurl has changed my outlook on my own...

3 years ago
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Making a Sissy 5

Making a Sissy By Jena Corso Edited by Angela Meyers Chapter Five Quickly the bib and sheets were off Justina as they pulled him from his feet and hurried him from the room. His legs were stinging as they practically dragged him down the hall and across the house as suddenly he was brought outside. Through some manicured gardens, their shoes clicked on well-placed huge chunks of slate as they rushed under a tunnel like rose trellis. As they came out on the other side, they...

2 years ago
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Making a Sissy 4

Making a Sissy By Jena Corso Edited by Angela Meyers Chapter Four "Oh gawwdd. This is actually happening." Lynne was beginning to sweat a little. "Is she going to freak out when she wakes up?" "It's impossible to tell," Contessa replied. "Normally they can be cranky at this early stage, and her body will be adjusting hormonally for quite some time." "Wow?" said Lynne, thinking about the situation. "I realize that's what we're here for of course, but I'm not so sure I was even...

3 years ago
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Not Maid But Mermaid

We were then staying at Vadodara and had recently come from Mumbai on transfer. For few months we stayed in Makarpura and then shifted to Tarsali. I was then 38 years old and my wife was 35. I had two children one daughter and one son. Since several months my wife was sick due to multiple reasons. It all started with pelvic inflammatory disease. Then severe stomach ache. Many gastroenterologist conducted many tests like endoscopy, colonoscopy etc and treatment was on. after few months she...

3 years ago
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The Maidenly Maids

The Maidenly Maids Belladonna [Author's Note: Based on a caption by Commentator] Rita Lopez hung her head as she looked down at the documents in front of her. She could not believe that Jack had been so reckless. She had known him since he was a young boy. She had watched him grow up in front her eyes. She had never had a child of her own. Watching her business partner raise Jack was the closest she ever came. When Jack got out of college with an accounting degree, Rita...

4 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

3 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
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The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

1 year ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

2 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

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