Sandy's Sissy Maid free porn video

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Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I was smooth. Mistress hated hairy sissies. And I had used lotion on my skin after the shower to ensure my skin was conditioned and soft. So, I was ready Monday when I woke. Woke rather early I must add. Normally I got up around 8 in the morning, that day however I woke before 7 and got up shortly after. I knew I needed to get dressed as told, in the maid uniform, right away. But it was early. And what if Mistress was not going to be on, had changed Her plans or did just not want to deal with Her sissy? So, instead of getting dressed, I stayed nude, made coffee then sat down at my computer. I connected to the internet, checked mail, then nervously opened Yahoo Messenger. I expected Mistress would not be on yet, thinking She would be busy getting ready to take Her daughter ready to school. But.... The message came instantly. "Are you dressed sissy?" My nervous reply being, "i am nude Mistress Sandy." I almost had started the sentence with, "No, Mistress" but quickly remembered the relatively new rule that I never use the word "no" in any form to my Mistress. I felt a little pride in remembering the rule so early, but Mistress seemed not to notice. She then gave a straightforward reply of, "Well then get off your computer and into your maid uniform!" Adding "Let me know when you are properly dressed." My heart sank as I realized I was going to have to dress, and likely had agitated Mistress Sandy by not obeying to begin with. Not wanting to further rouse Her, I typed, "Yes Mistress" and got off the computer immediately, not even waiting for a response. It was in a rather docile state I then went to the bathroom and began my transformation into Wendy, Mistress Sandy's sissy maid. Everything was laid out. I had known I was going to have to dress. Why had I risked disobeying Her? No need to question that now, what was needed now was to dress. Dress properly and fast. There was some comfort in only being told to dress. I had not been told I would be reporting to Her, I had not been told She would be coming over to my home. There was a very high possibility that I would just have to show Her I was dressed, maybe stay dressed a while as I cleaned my home or some other task and then be allowed to get on with my day, as a male. But first I needed to be a proper sissy, and I had already started the day off inappropriately. That in mind I began my transformation. First thing that had to be done was to put in my anal plug. Not something most maids wear but it seemed appropriate for sissy ones, like me. It was also one of the first things Mistress might check if She were to inspect me. I shuttered at that thought, not truly knowing. The unknown is always a dreaded thrill for an owned sissy. What might happen always on the tip of your mind. It is a unique feeling, placing yourself in a position where you know you will be humiliated, yet the excitement in not knowing how or how much leaves you a in a state of compulsion. For me, I become unable to resist the orders which lead to that humiliation. The slight pain as the plug settled in also added another dimension to it all. The first garment to go on was the gaff. Had I been wearing the chastity device this would not have been needed. There was a fear the device would be going on if Mistress had any plans to correct my disobedience for not being dressed when I first got on the computer, but for now it was off. Once I was tucked securely in the gaff with my "silly clitty" as She called it, between my legs, I put on panty hose. The stretchy fabric of these insured my genitals were firmly encased in the gaff and going nowhere. Mistress allowed pantyhose when I wore domestic uniforms in part because of the tight fit. It helped keep me focused on working. Then came a pair of frilly pink panties. Possibly unnecessary as I was wearing pantyhose, but I had been taught sissies always wear panties. Frilly ones. I took a moment to look at myself in the full length mirror. Standing there with my nails painted pink, my smooth hairless body, my legs covered by silky hose and my genitals well trapped under a cover of elastic and lace, I had no doubt what I was. Nor any resistance to what Mistress wanted me to be. I decided to go ahead and do my make-up before putting on the body shaper. As a domestic maid I was required to have make-up on, but just enough to make me recognizable as a sissy. Light foundation, blush, simple eyeliner and lipstick to match my nails. Once my face was done I put on the body cinching top with its breast cups and pads. I almost avoided looking at myself as I knew it would only excite me. But of course I did. And it did. I then took my pink domestic maid uniform off the hanger and dropped it over my head. That done I wasted no time in tying the frilly apron around my waist and slipped into the Mary Jane style shoes. I adjusted the wig on my head and crowned it with the humble maid's cap that matched the apron. A quick look in the mirror assured me I was dressed. I looked like what I was, a sissy maid. I almost felt a bit of disappointment in that Mistress would likely only inspect me over the computer and dismiss me. I wasted no time in getting back on line and messaged Mistress that I was dressed. This time there was a wait of at least 15 minutes before She answered. I knew as I waited She probably was sitting at Her computer, but it was Her way of letting me know She was in charge. When She answered me I was requested to show Her I was dressed on camera. There was a slight bit of scolding for not being dressed when I first got on. I again apologized to Her and promised I would be a "good gurl" for Her. That said I got a reply I had not expected. She simply said, "Good, you have 15 minutes to be at my door." I had to read it twice. I had not expected to have to serve in Her home. I had nothing ready to report to Her. The bag with my male clothing was not packed, my make-up and sissy things were scattered all over the bath room. The normal drive over to Her home took about 10 minutes. I instantly knew it was a waste of time to give any thought to this, so I typed "Yes, Mistress" and got off the computer. I grabbed my bag and tossed in a pair of jeans and shirt, added my tennis shoes, went to the bathroom and hurriedly crammed my sissy things back into the bags, keeping out my purse. I put my lipstick and blush in the purse, then quickly went to the kitchen and grabbed my wallet which also went into the purse. I picked up my car keys, looked down at myself, accepted I was a sissy and had to do as told, then walked to my car. The first block driving away from my home dressed as a sissy is always the hardest. The fear of being seen by my neighbors is so strong. After that it gets easier but is still terrifying. After about 5 minutes driving time all I can think about is the safety of being in Mistress' home. This time I also kept an eye on the time, anxiously hoping I would not be late. I knew better than to cover myself or remove anything as I drove. All I could do was to hold my head up high and act like any maid would act. A casual glance my way would only show a properly dressed maid, not a sissy maid. I arrived at Mistress' home on time and was let in quickly. She gave me an inspection and asked about my ear rings. I almost panicked! I had failed to put any on. I knew She would require me to return home, get them and drive back to Her. It was going to make me not only fail the inspection but also severely late. Just out of pure desperation l looked in a side pocket of my purse. I had a pair! I quickly put these on and profusely apologized, telling Her how nervous I had been when told to report unexpectedly. She responded that I had been told in advance I was to dress when I got up, and if I had done that I would have had plenty of time to check myself, adding that if I had done that I most likely would not be standing where I was anyway. She took my purse which now held my wallet and keys and tucked it under Her computer desk. Then with a laugh She said, "Well sissy, you are here, and you are dressed, so you might as well do your housework." With a flick of Her wrist I was then sent off to clean Her home. After a proper curtsy of course. I spent the next 3 hours or so cleaning, doing wash, making beds and waiting on a demanding Mistress. A Mistress who sat comfortably in Her living room watching TV, chatting on the phone and playing on Her computer. When things were straight She said I could dress in my "boy" clothes and had me sit in front of Her. She scolded me for my disobedience in not dressing when I got out of bed. She further scolded me for the ear rings and a few minor infractions occurred while serving and cleaning. She then asked me what I felt should be done in the way of correction. I felt relieved at being dress while punishment was discussed since a spanking was doubtful at that point. I began my defense by stammering how I had been good most of the day. I mentioned not protesting I report dressed, I had done my housework and served without any complaining and that I felt I had learned my lesson. She then asked if might not feel I should lose some privileges for a while, at which I just hug my head and gave a slight whimper. I knew She was referring to having to wear the chastity device. All I could say was I was sorry and would be good. She returned my plea by telling me to show I could be good and put the device on when I got home. There was nothing left to say but "Yes Mistress Sandy." She handed me my purse back while telling me to remember I was a sissy, Her sissy. Then reaffirmed that I was to put the device on when I got home, before doing anything else. I was not to wash my face, remove my fingernail polish or even remove the plug. With that I was out the door and on my way home. I wanted badly to wipe the pink lipstick off my lips when I got in the car. The foundation and blush were not as noticeable without bright pink lips. Driving wearing make-up is not the most comfortable feeling a 50 some odd year old male can do. It is a breeze compared to being a fully dressed sissy maid though. As soon as I got in the door at home I undressed and went to the back bedroom to retrieve the chastity device from the drawer where it is kept. The back bedroom in my home is a guest bedroom, but also Mistress Sandy's room in my home. Other than when vanilla guests are visiting, I am not allowed to enter it wearing any male clothes. One drawer in the dresser is for Mistress Sandy's use. Most of the things in it are used for my disciplining, paddles, whips, cuffs, a collar and leash.... It is also where Mistress uses these things for the most part but that is another story. After getting the device I went to the den and connected to the internet. Mistress wasted no time in having me turn on the camera. There was no foreplay, no teasing, no discussion, just an order to put the device on. I used a plastic numbered lock so that there would be no worry of my picking the lock and playing with myself. It was just a quick no nonsense lock up. I knew She was laughing as I closed the lock sealing my little sissy clitty away from myself. I felt so foolish, so helpless, doing such a ridicules thing. I was also highly turned on. Once the device was secure, the feelings of foolishness and helplessness seemed gone, replaced by relief and as amazing as it may seem, pride. I was not just a sissy, I was Mistress Sandy's sissy! With that thought I typed a quick "Thank You Mistress" in the messenger window. Almost immediately my phone rang. It was Mistress Sandy. Her first words were "your welcome wendy." The next thing She said was that since I had problems following orders I needed practice. Therefore, I would be dressing first thing in the morning for the next four days. She told me to wash and iron the pink uniform I had been wearing and dress into it as soon as I got up on Tuesday. She also informed me that any failure to obey fully would be punished without mercy. I knew She meant it, and uttered a rather frail but serious "Yes Mistress, i will be a good gurl." As soon as She hung up I went to wash my face and remove the fingernail polish. Knowing I would be dressing the next morning made removing the polish seem a bit absurd, but wearing pink polish on my fingers was not a good idea even if I did not expect to go anywhere. I was soon dressed as a male, on the outside at least. I did have the chastity device secured on me as a reminder that all was not as it seemed and was wearing a pair of panties as was required whenever I was in the device. I did do a load of laundry which include a pink cotton maids dress, frilly pink panties, a feminine body shaper and a few other items used to transform myself into sissy maid wendy. Other than that however I just went about the rest of my day as a man. Well maybe not man, but male at least. That evening I ironed the maid dress and started the process of painting my fingers again. During the three intervals between coats I played on line. Constantly looking at sissy sights, reading sissy stories and dreaming sissy dreams. Mistress only rarely popping up with a message asking what I was doing, was I getting prepared for my morning and reminding me my need to be Her "good gurl." Around 9:15, after the last coat of nail polish was on I went back to the computer and Mistress asked what I was doing. I told Her I was waiting for the polish to dry, to which She said, "Why don't you wait standing in the sissy corner. Set a timer for 1 hour. I will not be able to supervise you, I am tired and going to bed." I had anticipated there was going to be corner time when I was at Her home. It seemed silly She would simply tell me to administer the corner time to myself and not even have me turn on my camera as was normal for corner time when I was in my home and She in Hers. But that was what She had said, so I said "Yes Mistress" went and got a timer and stood in the corner for an hour. Nude other than the chastity device, wearing pink polish on my toe and finger nails. I knew Mistress would not be checking, in fact I figured She really did go to bed. I was all alone, standing in the sissy corner of Her bedroom in my home, waiting for the timer to go off. It was silly, but She had told me to do it. I had told Her I would do it. I know She wanted me to think of how much easier my life would have been had I only gotten dressed as told. And I did think about that, but I also thought about how if I wanted Mistress to be my Mistress, then I had to be Mistress' sissy. I had had a fantasy sissy life for a long time, Mistress was making it real. If I wanted to keep it real then I needed to do as She said. I needed to do things how She said and I needed to do things when She said. I jumped when the timer went off. It had caught me deep in thought. I got out of the corner and sat with a glass of wine, with the reality of what I had learned in the corner still going on my mind. That night when I went to bed I was ready, physically and mentally. I had again shaved what stubble there was, used lotion, readied my uniform, painted my nails and set my mind on total obedience. As I lay in bed the chastity device added a new layer of acceptance to my fate, as well as a tingle, keeping me not only willing but eager to obey. The next morning I again woke early. This time without any hesitation I got out of bed. I did go to the kitchen and start the coffee before dressing but was dressed before getting a cup. By 8:00 I was online and waiting for Mistress Sandy to acknowledge me. I waited for a good 45 minutes before She came on and told me I would be cleaning my home, dressed as I was, and should be ready for an inspection at any time. I spent the morning and a bit of the afternoon cleaning my home, watching anxiously for Her car to pull up out front. Just before 1:00 She called and asked how things were going. I replied the house was clean, beds changed and laundry done. She asked about the trash to which I had to say was gathered and taken to the garage. Naturally She wanted me to take it to the dumpster in the alley. It was only a teasing request though, but She did insist that after dark I would redress and take it then. I asked if I might be allowed to not have my nails polished since I had an appointment that evening and would have to remove it before going. She said I could remove it, but needed to repaint my nails anyway as I would be putting on the black domestic uniform first thing in the morning. I had almost forgotten I had three more mornings to dress as part of my "dress when you're told to dress lesson." It pleased Her to remind me. So later that evening, I repainted my nails, got dressed in the pink uniform again and took the trash to the dumpster. Sleep that night was much like the first night where the chastity device was concerned. Possible even a little improved. Resignation to one's state may have something to do with it. I did sleep better and longer. The next morning I again made coffee, got dressed and went online. Mistress was there quickly and wanted to see me dressed. The black domestic uniform is much like the pink one, though somewhat more formal. Where the pink one has a zipper, this one has large white buttons running the full length in front. Its lace is daintier and there is more of it. The maid's cap is made of the same lace. This dress also has a longer skirt. Mistress had me turn and bend and show various areas before telling me I was a good gurl. Then She told me I was to write a paper on "Why a sissy should report to her Mistress dressed like a sissy", send it to Her then I could get undressed and do as I wished. As I began writing the paper I felt it would have been easier if I had been requested to report. I knew the paper was going to cause problems in the future. As much as I disliked the thought, the requirement of being dressed to report began to make more and more sense as I wrote. Some of my thoughts from the corner on Monday even worked their way into the paper. To be honest, the more I thought and wrote the further I slipped into submissive sissy mode. By the time the paper was finished I had myself so worked up I was breathing fast. Reading it over I decided to keep this paper to myself and make a new one to send. One that was toned down a bit, gave less insight to my sissy realizations and might have less impact on my sissy reality. When it was written I went online and let Mistress know I was finished. She asked if I had learned anything. I said I had. She asked if I now understood the reason She often had me report to Her dressed. I said I did. She asked if I had been honest in the paper and felt it showed my true need to obey and server Her. I assured Her it did. She gave me a stern warning that if I had to rewrite the paper it would not be a pleasant experience. Then She told me to send it to Her. I gave a sigh to myself, typed "Yes Mistress" and sent the original paper, knowing I was trapping myself deeper in Her web. As soon as She received it She told me I could get undressed with a reminder not to play with my sissy clitty. Adding a "ROTFL" after the message. I knew as I got undressed Her hold on me was way more than just physical. All I could think about was Her reading the paper and learning not only the depth my submission went but also some new ideas on how to better control me. All willingly given Her. With this thought I got dressed, putting a pair of the frilliest sissy panties I owned over my chastity device. Later that evening I received a message telling me the next morning I was to dress in my black serving maid uniform. It is an English maid uniform, made of a silky material, with high neck, long sleeves, short puffy skirt and lots of lace. When wearing it I was required to look like the proverbial sissy maid. A total undeniable sissy. With more detail in my make-up, shoes with higher heals and shear stockings with a garter belt. I spent the rest of the night dreading having to dress that way first thing in the morning. After having me send Her the paper about reporting to Her dressed, I had huge concerns as to Her intentions. My mind became a mass of conflicting thoughts. I wanted to obey, I wanted Her to be proud of me, I wanted to be a sissy, Her sissy. I also knew the whole process would leave me at Her mercy. Open to any humiliation She might devise. And the thought that I would be dressed that way because She had deemed it necessary I learn a lesson in obedience was not a comforting one. Sleep that evening was a little less easy to come by, and the device was beginning to do its job of reminding me someone else had control of my erotic pleasure. Pleasure I was beginning to long for. Thursday morning I woke very early, with my sissy clitty trying to grow. After getting out of bed to urinate I went back to bed and slept until almost 8:00. As was becoming normal I made coffee and started dressing. The make-up took close to 45 minutes, and by the time I got online it was just after 9:00. Mistress wanted to see me and asked why I had taken so long to get on. I asked if I might be allowed to call Her as I showed myself on camera and She agreed. I explained my sleep problem, the extra time it had taken to look like a proper sissy and promised that I had been obeying but was just a little later than usual. She seemed to understand and was pleased as to how I was dressed. To my great relief She told me to stay at my home, but remain dressed until 1:00. Adding She would get back with me and check that I was obeying. I gladly agreed trying not to show just how relieved I was. She suggested I make sure the house was straight and clean but not to get my pretty uniform or make-up messed up. Before She hung up She told me my paper had passed. She said that both She and Her Husband had enjoyed it a great deal. I often wondered about Mr. Robert, Her Husband. What he thought of me, of the relationship I had with his Wife. He knew we were not having sex, but he also knew the effect I had on Mistress Sandy. The times he had seen me dressed he always seemed more amused than anything. And the one time he had seen the chastity device on me he had simply said, "It looks good. On you at least." I often wondered if he might have a few sissy tendencies. There was also some concern he had dominant tendencies. I just did not know. I did know however, that when Mistress got all worked up She shared Her relief with him. And from what She had said about the paper They must have had a fun night. After hanging up the phone I spent the next hour and a half fidgeting about in the uniform. The heels constantly reminding me to walk like a sissy and the short flared skirt reminding me I was a sissy. When I heard a car pull up outside I was quickly reminded just whose sissy I was. Looking out the window I saw Mistress Sandy's car pull up and park. My heart raced as I watched Her get out and come to the door. I answered without Her having to ring the bell. She looked me over, gave a smile and turned back to Her car and motioned with Her hand. Her car has heavily tinted windows so I had not noticed there were passengers. I tried to watch as the doors opened but Mistress marched me away from the door and to the living room. There was an evil grin on Her face as She gave me a firm order that I not forget to curtsy. I tried to keep from shaking as two Women entered my home and gasp at me. I curtsied to each but was unable to speak. I wanted to cry so badly. The three Women just laughed at my plight. My fright settled into acceptance somewhat quickly and I was able to regain some composure. Mistress suggested I make coffee and then led the Women to my den. I gave a deep curtsy and went to kitchen. With the coffee made, I got a tray, three cups, cream and sugar and went to the den to serve. Mistress was so proud! I felt like such a sissy. One of the Women had seem me before, one had not. Mistress was in a mood, and wanted to show me off. She pointed out the details of how I was dressed, exposed my panties and garter, then even the chastity device and anal plug. She had me curtsy and walk for the women. After a refill of the cups She sent me to a corner as They talked and watched TV. This time I was unable to think, I just stood there humiliated and exposed for what I was. Around 12:30 Mistress called me and had me remove the cups. When I returned She said They needed to go and I could change after They left. As I opened the door and started my curtsy for the two Women, Mistress firmly stated "Be fully dressed in the pink serving uniform by 8:30 in the morning. DO NOT BE LATE!" One of the Women stated She bet I looked adorable in pink. I was in a deep curtsy to Mistress Sandy as She replied, "Yes she does, maybe you'll get a chance to see." They left laughing as I was left shaking. I changed with a most intense longing to play with myself. Again, crying seemed a good idea. After removing the nail polish and make-up I decided to continue wearing the same frilly panties Mistress had exposed me in, as my panties for the day. After I got dressed in my male things I went to the back yard and began doing some yard work just to get my mind off things. It did not work though, I still wanted desperately to play with myself. That evening was the hardest. I was so worked up. I knew the pink formal uniform might be bad news, besides it was my last day of sissy dressing lessons. I took extra time to shave and do my nails. I made sure all was ready so that I would not be late in the morning, even setting my alarm to wake me at 7:00. It seemed such a ridiculous idea setting an alarm to wake me early, so I could get dressed like a maid and submit to a Woman who I knew was just using me for Her entertainment. Rubbing the chastity device I realized I was getting what I wanted, and questioned just who was using who. I woke at the alarm eager for the day to be over. Without bothering for coffee I went to the bathroom and dressed. I was quite delighted at how my face tuned out. I used all my frilliest pink underthings and my finest hose. Once I was in the dress I fluffed my wig, added my laciest maid's cap, ear rings and stood back to admire myself. This uniform was similar to the black serving uniform, with even more lace, a puffer skirt and a pink color that only a young girl or a sissy would wear. I did not look like a Female in it, but I was not a Female. I looked like a very sissy sissy. Which is what I was. I felt sure Mistress Sandy would be pleased, but looking how I was dressed grew somewhat concerned as to Her plans for Her sissy. Whatever happened was inevitable though, so I stepped into the white, 4 inch heels, minced to the computer and signed on. It was just 8:20, and She immediately asked to see me. She seemed very pleased indeed. She told me I was to stay dressed until She advised me I could change, then dismissed me. It was both a shock and a relief. Was it really going to be that easy? I made a pot of coffee and turned on the TV. It was amazing how after a week of dressing I was now able to feel comfortable dressed this way. I was so able to relax and enjoy the feeling that I forgot about my chastity device. I almost even forgot the possibility Mistress Sandy might have plans for me. When the phone rang a little after 9:00 my comfort came crashing down however, as I heard Mistress Sandy say, "My door, 15 minutes. Bring your purse but leave your boy things at home. Is that clear sissy?" It was, so I stammered a simple "Yes Mistress" and hung up. I will not say it was unexpected. This time the bathroom was in order, all my things put away. My purse was out and packed with make-up and a few items I might need. There was even a packed bag of male things that would unfortunately go unneeded. All I had to do was get my car keys, wallet and walk out the door. Well, that and gather the greatest amount of sissy nerves I had ever gathered. All the way to the car I was telling myself, out loud no less, "Please, please don't make me do this." I knew I was talking to myself as Mistress was nowhere near, which was why I went ahead and used a form of the word "no." Still, I knew it was wrong and quickly told myself that I was not to use that word. Nonetheless, it was what I meant. I did not want to get in the car, I almost had an urge to stand up and be a man. What I did however, was accept I was a sissy who had been given an order, which I had to obey. So I got in my car and backed out of the garage. The drive was again initially terrifying. Why my car did not have tinted windows I did not know. I was at least grateful my garage was in back of the house and the first part of my drive was in the alley. I headed in the opposite direction I normally drove out, in order to avoid any chance of being seen by my closest neighbors. It also meant I was going to have to drive in the alley a block longer than normal. Anyone in back of their home would unquestionably see me. I got to the street and with some relief was on the way, unseen. But now I was driving on a major street, wearing a fully adorned pink maid uniform. Sissy pink maid uniform. I thought about the paper I had written. It had truly been honest. Doing what I was doing was an act that took me deeper into submission and at the end of the drive I would be eager to stand before Mistress Sandy. I would feel safe in Her home, safe with Her. At least I would be safe as long as I was obedient, and enduring this drive had a large effect on my willingness to obey. I pulled up to Her home grateful to seemingly have gone unnoticed on the drive. I got out, walked to the porch and knocked on the closed door, then waited. I knew better than to knock again, She knew I was coming. It was only about three minutes but seemed much longer as I stood there exposed in my pink frilly uniform. When She opened the door She said She had been dressing. After entering I gave a deep curtsy and was inspected, closely. Though it was not my place to inspect Her I did notice She was dressed more formally than normal in Her home. In fact She frequently wore only a robe when I was there. Having a sissy serve Her often got Her in a "mood" and the robe allowed easy access for personal enhancement of that "mood." But today She was fully dressed and made up. It gave me a somewhat uneasy feeling. I felt a bit safer when She sent me to straighten the dinning and kitchen areas. As I was putting things away in the dining room Mistress came in with a box and placed it on the table. She opened it and began pulling out a collection of adult toys, all new and in their wrappers and boxes. Most were for use by Women, vibrates, insertables and such. They were toys Mistress showed and sold at Her erotic toy parties. I had served at a few of these, small ones, held for Her close friends. But I had never known Her to have any of the parties during the day. They were always at night. Still, it did not take a rocket scientist to make the connection. I was in my prettiest, frilliest, sissy serving uniform. Mistress had brought out the collection of toys She showed at Her erotic toy parties. I knew what it meant, but still ask, "Are You having a party, Mistress." Her reply being, "Yes wendy, we are having a party." "When Mistress" was all I could utter. I am sure She was pleased to be able to tell me, "The guests should start arriving in about 45 minutes". I dreaded asking but could not help myself, "How many guests will there be, Mistress?" This time the grin on Her face left no doubt as to Her pleasure as She said, "There will be about 20, so we had best get busy sissy." It was the ball I had been waiting to drop and She knew it. I stood there breathing heavily, the tight girdle I wore adding to my torment. Mistress was headed to Her bedroom but gave a resounding laugh and said, "God sissy, I need to use one of those vibrates sooooo bad!" She returned with a smaller box of toys and told me to arrange them all on the table. I could tell She was flustered. It gave me a slight giddy feeling knowing She was going to have to wait to pleasure Herself. It seemed somewhat fair considering my own plight. I began arranging the toys as She went about taking the dining chairs to Her living room. In fact, She went all over the house gathering chairs. There was a mirror in the dining area in which I noticed my reflection. In about 30 minutes I was going to be exposed as a total sissy to some twenty women. Somehow my state seemed even more pronounced as it was day time. The few times I had been exposed to groups at night there was at least the illusion that I was only a part time sissy. Man by day, sissy by night type thing. But now there would be no doubt. Not to the Women, not to me. I had spent the week waking up and dressing like a sissy, Mistress was getting me in a frame of mind. A frame of mind which now matched my image in the mirror. With the toys arranged I reported to my Mistress in the living room. She looked wonderful, and the light perfume She wore added an air of firm femininity. As I curtsied She asked if I was OK. I know She was asking if I felt I could handle what She was about to do to me. I gave another curtsy and said, "Yes Mistress, I am going to make You proud." She gave a tender smile and said "Good gurl" then turned to the window and exclaimed with some relief, "Thank heavens, the food is here." I almost died as I watched a man caring a tray approach the door. I did not know who he was, I still do not know who he was. Mistress simply opened the door, asked him in, said "Sissy, take the tray to the kitchen", then turned and reached for an envelope. He showed no sign of shock, but made no effort to spare me from my humiliation. As he handed me the tray he chuckled and said "here you go sissy." Mistress gave him the envelope, they exchanged pleasantries and he went out the door. When I returned I noticed he looked back at the house, smiled and then got into a small truck. Mistress laughed and said "I think he liked your dress dear, or maybe he liked you in the dress" then headed for the kitchen. I hesitated for a moment as I watched the truck drive off, my mind a mass of confusing thoughts. Mistress had me set the tray and arrange plates and forks with it on the kitchen counter. She told me to make some sweet mint tea and put out some plastic glasses and napkins that were in a bag on the floor. She added "The girls can serve themselves in here first and then you can take over the serving duties when we go to the other rooms." She left me to arrange the counter and make the tea. Just as it was ready and put on ice I heard the doorbell ring. There were voices and greetings, giggles and laughter. Suddenly there were a mass of women in the house. When Mistress called to me I gave only a slight hesitation then entered the living room. The most realistic way to depict my entrance is shock and awe. Followed by uproarious laughter. Hands went to cover mouths, some mouths gasp open, eyes widened and a loud "Oh my God" could be heard even above the noise. But what I noticed most was that while all the women were nicely dressed none wore dresses. And there I stood in my frilly pink overly effeminately flared maid's dress with apron and lacey maid's cap. I was an obvious male wearing make-up and decked out like a movie prop maid. Mistress took control and loudly announced, "Ladies, this is my sissy, wendy." There were a mass of questions, some aimed at Mistress and some aimed at me. I did my best to answer, as did Mistress, and it soon became clear that I was not a prop, I was a sissy maid. Things settled after that and Mistress had me lead the group into the kitchen where I helped them fill their plates and get their drinks. By the time everyone had been served the crowd had moved into the dining area and was ogling the toys there. I stood quietly against a wall but will not suggest I blended in. More than one of the Women inquired if I was for sale also. The group then moved into the living room to discuss the toys, their experience with them and a vast array of things few males ever hear Women discuss. Even sissy males. I was kept busy filling drinks, taking plates and avoiding the occasional pinch and grasp. I did my best to curtsy as needed and be an ever proper maid. Mistress did seem pleased. Time actually seemed to fly and before I knew it the party was over. Cleanup was simple. I helped Mistress put the few toys left in the small box, dispose of the food tray and bag all the trash. The chairs were returned to their places and the living room put back in order. Then Mistress had me follow Her to the bedroom and help Her undress. It was one of the few times other than when allowed to bath Her that I saw Her totally nude. She told me to stand in the corner, then proceeded to lie back on the bed and go at Herself with several of Her most prized toys. Close to 3:15 She let out a sigh and said She needed to be calmed down when Her daughter got home from school. I had been seen by the high school aged daughter in the basic domestic uniforms but not dressed as a full-fledged sissy. Mistress gleefully announced that after Cindy saw me dressed as I was, I could leave. It was not an experience I was looking forward to, but I had little say in the matter. We returned to the living room, Mistress had me redo my make-up and adjust my dress and apron. Then we proceeded to talk. She did care, She wanted to know how I felt. She assured me I was safe with Her saying "you're my sissy, I'm not going to let you get hurt." Then adding, "But you need to always remember you are my sissy. I am your mistress. I make the rules, you follow the rules, so when I tell you to dress first thing in the morning, you dress first thing in the morning. Understand?" I did, it had been made clear. I gave a curtsy and said "Yes Mistress." With that I was sent to the corner in the living room to wait for Ms. Cindy's arrival. The TV was on, but the sound at a low level. So when the door opened I could hear that more than one person entered the room, even over the "shush" sound Ms. Cindy gave. There were also two distinct though quite giggles as I heard someone sit on the sofa. Mistress said, "Wendy, you may come out of the corner" so I turned and faced Ms. Cindy and a friend, both obviously amused. Mistress asked if there was any sweet tea left from "lunch" to which I answered "Yes Mistress." I was then sent off to get the girls tea and packaged cookies. I took my time as Mistress and Ms. Cindy were explaining what I was to Her friend. It was evident the girl had been told about me but had been unconvinced. Returning to the living room with their afternoon snack I felt sure Ms. Cindy's claim had now been validated. I gave one of my deepest and best curtsies to eliminate all doubt. Mistress gave a big smile, handed me my purse and told me I was dismissed. I wanted badly to run out the door but tried to keep my composure. At the door I turned and did my best to ask Mistress if I might remove the chastity devise, without actually asking of course. That was something Ms. Cindy did not know about (at least I did not think so) and not something I wanted known. Mistress said we could talk about that after I got home and stated She wanted to see me dressed when I got there. I knew that was so that I would not remove anything in the car. So I drove home the way I had reported. Fully dressed, fully made up, with the lacy cap atop my wig. There was more traffic, more cars and more people, but I made it home safely. I immediately went online and reported. Mistress was so proud of me. She said I was such a good gurl. She said all Her friends were now jealous of Her. After a few moments of this praise I got the nerve to ask if I might be allowed to remove the chastity device. She again asked all the questions about had I learned to do as told. When? Where? How? I wanted to scream YES YES YES! I pledged Her my obedience. Then She said there was one more thing She wanted me to do. I waited in horror to hear what it might be. She then told me that after I got up in the morning, She wanted me to remove my chastity device, then asked "Can you do that sissy. Can you be a good gurl for me?" She made it sound like I would be doing Her a favor. I typed "Yes Yes Mistress, i can be a good gurl Mistress, Thank You Mistress". She then dismissed me and said we would talk again soon and I should have a nice day tomorrow. I got undressed, washed, took off the fingernail polish and sat down. I was wearing an old pair of jeans and still wearing my old friend the chastity device. I was certain Mistress would not be checking on me. I could take the device off and She would never know. I could play like a wild man all night long. And I wanted to, but.... But I was not a man, I was a sissy. And I did not want to be a man, I wanted to be Mistress' sissy. I have to admit, that night in bed I did cry a little. I think it was because I was so happy, though it might have been because I wanted to play with myself so bad. The next morning when I woke I was eager to do exactly as I had been told, oddly however I did not want to rush things. I made coffee and sat for a few moments thinking about the week. But I did not think long. I was truly proud of myself for being such a good gurl as I did just as I had been told. I broke the plastic lock off the chastity device and I did have a good day!

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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

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. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

1 year ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 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. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

3 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

1 year ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

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