How To Build A Better Sissy, Part Deux free porn video

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How to Build a Better Sissy Part Deux by: Missy Satinpanties I spent the rest of the night sleeping like a rock in my diapers. Maybe sleeping like a baby? My new master came in to the room several times to check my diaper, and changed me once. Finally, around seven thirty in the morning, he came in, and gently pulled the curtains back, and opened the mini blinds over the window. I was told to get a shower, and to put something pretty on, while he ran out to get us some breakfast. As I showered, I reached behind me to soap and wash my bum hole, and realized it was very, very sore. Taking a dump was surely going to hurt today! While I was patting myself dry, I saw that there were two things on the sink that I had not left there. One was my floral scented dusting powder, and the other was a small white plastic bottle of something, with one of those yellow sticky notes on the back. I picked that up first, and read the label. 10% solution Lidocaine. I read the note, and it told me to use the cream liberally on my bottom, two or three times today, as it would help with the pain. I rubbed a bit of the cream on the surface, and then gritted my teeth, and ran my finger inside my back passage. "Damn! That hurts!" But, in a few minutes, the pain went away, so the Lidocaine must be working. I also noticed my finger was a bit numb! Looking at the label, it did say to wear rubber gloves! Since I was dressed like a baby when I got up, I thought maybe that "something pretty" might mean more of the same. I thought about it for a bit, and figured that whatever I put on, if Mr Jenkins didn't like it, I could always change. I went from the bathroom, back to the pink bedroom, and started going through the drawers. I finally remembered what I had done with what I was looking for. A while ago, I had contemplated buying diapers and plastic panties, but had decided that I had no use for them. But, day after day, the thought had nagged at me. I knew there was nothing more helpless and vulnerable than a baby, and finally ended up buying a dozen cloth diapers with thick soaker pads, and 4 pair of plastic panties from a shop on EBay that had them on sale. Yeah, I had spent nearly $350.00 that day. I had placed all the diapers and plastic panties in a box in the closet. Not hidden, mind you, but on the floor, and out of my thoughts. My Master must have found them after I passed out last night. I pulled the thick cloth diaper around me, using a set of directions that had been thoughtfully included in the shipment, and pinned them tight. I then selected a pair of plastic panties that were covered in baby blue satin with 4 rows of lace on the bum, and a big bow in front. Next came the short, ankle length nylon socks with a cloud of baby blue lace at the top. Black, patent leather Mary Janes were buckled on, and then it was on the the dress and accessories. A short satin dress, in baby blue, of course was added. Big, puffy short sleeves, lots of white lace, and a set of frothy petticoats that made the short skirt stand almost straight out. A baby blue choker trimmed in lace went on next, followed by a matching satin baby bonnet. Now came the indecision. Short white satin gloves, or the fingerless baby mittens? They both were cute, but the mittens were so much more submissive. Hmmm. I finally went with the gloves, knowing that my choices may not be HIS choices! A quick spritz of perfume, a bit of pink lipstick, and then I pinned the ribbon of a pacifier to the bodice of my dress, and popped the paci into my mouth. A quick look in the mirror, and I knew that something was wrong. The gloves and the baby look just didn't go together. I quickly slipped them off, and pulled on the baby blue restraint mittens, but before I pulled them on, I tied the ribbons into loose bows, so at least they would look as though they were tied on. I had to use my teeth to pull the second mitten on, squeezing my hand through the elastic cuff, but when I looked into the mirror again, I knew it looked right, and more to the point, it felt right. I was a vulnerable, helpless, little sissy baby. When Master returned, I was sitting on the floor of the living room, waiting in my baby finery. He made me stand up, although I had to stand a bit bow-legged due to the very thick diaper, so he could see my outfit. He was very pleased with my choice! We ate breakfast together, with the only difference being that I was not given any coffee, and only allowed to drink apple juice from a baby bottle he purchased at the market. Humiliating, but that in itself was satisfying to me! After breakfast, he told me what was going to happen on Monday. "Tomorrow," he said, after I was back sitting on the floor, pacifier back in my mouth, "you will be re-assigned. Your new job will be to function as my secretary. You will always wear at least panties, garter belt, stockings, and either a bra or camisole to work, and every morning, you will report to my office to demonstrate that you are in compliance. As you will be moving from an analyst's post to a secretarial, your pay will naturally be much lower. Therefore, you will have to move out of this apartment, and into my house. The only furniture you will bring will be the contents of your sissy bedroom, and also all of your sissy clothing and accessories. You will NOT be allowed to bring any male undergarments with you. You will bring enough male clothing to cover yourself at work, and will bring no casual male clothing with you. We will either sell or donate everything I don't want you to have. In a few weeks, I will decide whether or not you will continue working as a man, or even if you will continue to work. At home, you will be my sissy slave, and will serve me in any capacity I choose, and will serve any man or woman I decide you will serve. If these instructions are clear to you, nod your head. If you do not wish to comply, then the pictures I have taken of you, dressed a baby, and those of you bent over with a plug up you sissy ass, may be placed on the company server for all to see." I was trapped! I wanted to comply because in a very, very short time, I had come to terms with the fact that I loved the humiliation and degradation that I had been subjected to, and wanted more. I had been dancing on the fringe of this for so long with the clothes, the furniture, the self bondage, and all, that it seemed like the natural progression of things to become a man's slave. On the other hand, I had a reasonably nice life here, and wanted that, too! But I thought about that for a bit. Sure I had a good job, but I had no friends, my apartment wasn't really mine, it was rented. My furniture was mostly flat-pack crap from an overpriced store. Plus, he claimed to have photos of me, even though I don't remember him taking any. Could I take that chance? I had to think. I sat on the floor for a long time, and realized that I didn't even need to choose. I had made my choice early the day before, when I invited my boss back to my place...no, I made that choice when I dressed up to go to the book store. No, I really made that choice a long time ago when I started to wear my mother's lingerie. I was really nothing but a pathetic sissy, and it made me sad somehow. Slowly, and with tears running down my face, I silently nodded my head, placing myself at the total mercy, or lack thereof, of Mr. Jenkins. I was told to take the week off, and to take care of moving my things to Mr. Jenkins house. I was also told, in no uncertain terms, that if he caught me with any male underwear, at any time, he would bind me, put me over his knee, and spend at least an hour with a paddle. The rest of the day was spent with me in diapers and satin, and Master lounging in what used to be my black silk kimono. I was only allowed to drink from the baby bottle, while Master drank a few of my beers while we watched some movies from Netscape. The only time I was allowed to take the pacifier out of my mouth was to suck on my bottle. Finally, about two in the afternoon, Master made me suck him off, and then he took my bottle and went to get dressed. He returned about 20 minutes later, with my bottle. He told me to start sucking while he talked. I noticed the bottle was warm, and when I put it to my lips it was...Piss! He actually wanted me to drink his piss! I looked up him to protest, just as he finished taking a cell phone picture of me, and I knew that I had no choice in the matter! He told me what he wanted me to do over the week while I was off work. I was to list my furniture on Craigslist, with prices low enough to guarantee a sale. Anything left next Sunday would be donated. He also told me to have all my male underwear and casual clothing packed up into trash bags by five on Monday, and he would come by and pick them up. I was to be waiting for him at 6:00, with the door unlocked, and standing in the middle of the room, wearing a sissy dress with my hands cuffed behind my back, and my penis gag in my mouth. Shit! Monday, I was up very early, and started to clean my crap off of the furniture I was going to sell. By nine, I had all the pictures taken, and by ten thirty all my postings to Craigslist were complete. An example would be the two leather Poang chairs from Ikea. Both had footstools. I had paid about $160.00 for each chair, and I don't remember what I paid for the footstools. I listed them at $50.00 each, or both for $90.00. "Must move fast, letting darn-near new stuff go cheap." I then spent the rest of the day gathering clothing. Sweats male underwear, bathing suit, jeans, and T-shirts all went into big black garbage bags. I kept a few shirts that I sometimes wore to work, but were really casual. I then went through my clothing again. Yep, I grabbed my polo shirts and those casual shirts, and out they went. By the time I was done, there were five garbage bags on the living room floor. I had been working all morning in just bra and panties, but when the phone rang, and the man who called told me he wanted to buy all the stuff I listed, and wanted to come by this evening, I had to think fast. Master wanted a cuffed sissy in the living room, and this man would NOT want to see that! Of at least, I didn't think so... I told the man that I had an appointment this evening, and I would leave the ads up, but tell any callers that I had a tenative buyer. If he wanted to come by Tuesday evening with cash, I would not sell to anyone else. If he did not come, the hold would be off. Turns out, he wanted to buy it all for his daughter who was just getting started in the world, and the price was more than right. I ate a bit of late lunch, and thought long and hard about my future. Mr. Jenkins was not just our department manager, he was over the whole division, and worked out of the main office, which was on the fifth floor. In fact, my old cubicle was actually in the basement, so for the most part, I would not see my old coworkers who came in and went down a half-flight of stairs to get to work, where I would take an elevator up. I think I would also be coming in a bit earlier than the analysts, so with any luck, I would rarely see anyone I knew. This sort of thing was trivial, I knew, but it kept me from contemplating the enormity of what I had done. In one day, hell, less than 18 hours, I had outed myself to my boss, revealed my innermost fantasies, and agreed to become his sex slave. What in the Hell was I thinking? It was now about three thirty, so I began to think about what I was supposed to wear. Master had told me to wear a sissy dress, but wasn't specific as to which dress, underthings, etc. I guess I was supposed to try and make him happy. With the thought rambling around in my head, I went to the bathroom to get ready. Shaving was a thing of the past, thanks to many thousands of dollars worth of laser treatments, so I didn't need to worry about that. I took a bath with perfumed bath oil, washed my hair in the sink. I had been letting my hair grow out, and usually wore it in a low pony tail, unless I was playing dress-up. I would have loved to go to a hairdresser and have it styled, really girly, but of course never got the nerve. After dusting myself with powder that had the same perfume as the bath oil, I went to the pink room to decide. After much rummaging around, I decided that I had better go "all in." First to go on was a thick cloth diaper. After a moment, I let it fall back to the bed, and grabbed one of the thick doubler pads, and then pinned the whole, ultra-thick package tightly around my waist. I grabbed a pair of plastic rumba panties that were covered with yellow satin, and the "mandatory" rows of white lace over the bum, and a huge white bow in front. After tucking the diaper in, I grabbed a pair of white, thigh-high stockings with silicone hold-up strips, and rolled them up my legs. White baby doll pumps with 5 inch heels came next, and I have to say, that even today, buckling the ankle strap on a pair of heels sends a little electric shiver up my spine! I took the yellow party dress out of my closet, and just looked at it. I had spent almost three hundred dollars on this one, and it was the prissiest, sissiest, and most beautiful dress in the world. Thick beautiful satin, balloon short sleeves with cuffs of white satin. A white satin peter pan collar, white bows over both sleeves, and lots of white, glass silk trimming. There was a choice of a white satin pinafore, or a white satin sash that came with the dress. I chose the sash. I put on the stiff petticoats, then slid that heavenly creation over my head. Having already hooked the paper clip and string to the zipper, I easily pulled it up, and hooked the little hook at the top. I grabbed the sash, put it around my waist, and tied a big bow, then spun it around to the rear. Looking at the time, I realized that with all my prep and my daydreaming, it was almost five thirty! I quickly stuck my penis gag into my mouth, and buckled it behind my head. I put a white lace choker collar around my neck, and a yellow satin baby bonnet was quickly tied under my chin. I grabbed my cuffs and went into the living room, where I, with shaking hands, unlocked the door. Moving to the center of the room, I started to put the cuffs on, and then darted back to the pink room. I grabbed the spreader bar and a pair of white satin gloves. I would have worn mittens, except I didn't have any in yellow, and had no idea how I could cuff myself with them on. I slipped the silky gloves over my hands, and bent down to attach the spreader bar to my ankles. (At least I had the presence of mind to adjust it down so that it wasn't at it's widest!) With a bit of difficulty, I cuffed my wrists behind my back, and stood there, waiting. As I stood there, I looked up, horrified! During the day, I had opened up the mini blinds on the door, and the two front windows to let in the light. I mean, if anyone had actually walked up and looked in, they would have seen a guy in a bra and panties, but you really couldn't see from the sidewalk. But, now it was getting dark, the room was lit, and I was bound in little girl frillies! I was standing in the middle of the room, bound, gagged, dressed like a simpering little sissy baby! My skirt and petticoats made certain that my panties were on view, and the penis gag in my mouth made sure that I was drooling on my little Winnie- The-Pooh bib that I was wearing for that reason! Anyone walking by on the sidewalk could just glance over, and clearly see me! Shit! Shit! Shit!!! I kept staring at the minute hand on the clock, watching it creep every so slowly from eight minutes to six, then seven, then six, and finally it was six, and then five after, and finally, after an agonizing wait, the door opened at about nine minutes after the hour. I truly hoped it was Master, because in the last five minutes or so, I had become convinced he wasn't coming, and I had been frantically trying to get out of the cuffs, with no luck whatsoever! As the door opened, I could see, with great relief, that it was indeed my boss and master. However, he just stood there, just inside of the door, and off to the side a bit. Anyone could look right in at me! I frantically tried to tell him to close the door and mini-blinds, but all that came out was a mumbled mess of sound. He finally closed the door, and then after a moment, the window blinds, much to my relief. He then started to walk around me, reaching out to touch a bit of the crinolines, then my shoulder, running his hand over my stocking, and caressing my bottom through the layers of cotton, plastic, and satin. All I could do was moan in anticipation. Master told me that he was happy that I was following his orders, so far. He then told me that he was going to inspect my apartment, to make sure that I had gathered up all the male clothing that I was required to gather. All I could do was stand there on feet and legs that were beginning to hurt a bit from the high heels. After about ten minutes or so, he was back, standing in front of me, with an armload of clothes. "Well, Sissy," he began sternly, "I see that you cannot fully comply with a simple set of instructions! You thought, maybe, I wouldn't check the washing machine or dryer for a hidden stash of boy clothing?" With that, he grabbed the only upholstered chair in the room, and swung it around until I was standing behind it. Then, he grabbed my plastic panties, and jerked them down, and quickly unpinned my diaper. Grabbing my cuffed wrists in one hand, he pulled up, forcing me to bend over the back of the chair, while he pulled off his belt with the other hand. Before I knew what was happening, he was whipping my bare ass with his belt! "Sissy bitch!," he grunted between swings, "You are going to learn that when I tell you to do something, you will do it! I found a pair of jeans, three pair of underwear, and two pairs of socks in the dryer, and you are going to get 3 licks for each!" By the time he was finished, my ass was on fire, and I was crying, screaming, and begging through my gag, drool and tears falling fast. He left me standing there, while he replaced his belt, and then put the chair back where it belonged. I suddenly saw, for the first time, that serving a master was more than a game, more than sexual pleasure. I had just received a real eye-opener, and wasn't sure I liked it! There was no sex, no release, no tenderness that night. I was sent to bed in a diaper and nightgown about eight, after being told to use the Lidocaine cream on my backside so that I could sleep. The rest of the week was a sort of series of stops and starts. Tuesday night came, and the gentleman came by to look at the furniture from the Craigslist ad. He ended up offering me a good price on everything, including my "man bedroom" suite. An hour later, he was back with his two sons, and all my things were quickly loaded into a large rental truck. I offered to help them carry things to the truck, but was told that I shouldn't strain myself. I didn't know why he said that, but... After they were gone, I was left with the contents of my pink room, one folding chair, and my TV. I told the man that new furniture was being delivered on Thursday or Friday, and that was why I was selling so cheap and quick. I awoke on Wednesday sort of lost. I had no work to go to, no furniture to lounge around on, and no idea of what to do. I finally got up, took a bath, and put on a full set of lingerie. Lavender sissy panties with a huge amount of lace, matching camisole and garter belt, with white thigh high stockings to finish the outfit. I went into the now empty man bedroom, and took a pair of gray dress slacks, a dark blue oxford shirt, along with a pair of patterned gray socks, black shoes and belt. I carried these into the pink room, where I got dressed, making sure that the camisole didn't print through the shirt. I took the check for my furnishings, and headed for the bank. I cashed the check and then drove about 45 minutes to a large mall, where I figured I could spend the day wandering about, doing some window shopping, and have some lunch. I had a decent day, browsing in the specialty stores, and of course, just before leaving, had to go into Victoria's Secret. I was holding a beautiful peach silk camisole up to look at it, when the sales girl, a beautiful young thing in a very short skirt came up to me. "VS lingerie tends to run a bit small," She began, "I think you might need a size large. Also, let me show you the matching panties and garter belt for that, they are simply to die for!" I looked at her as though there were horns growing out of her head. "How did you know they were for me?" I was so startled, I wasn't able to conjure up a good story. She put one dainty hand on my shoulder, rubbing it back and forth over the strap of the camisole, and whispered in my ear, "Well, Sweetie, I don't see many men in the store with pink nails, gold teddy bear earrings, smelling of pretty perfume, and already wearing lingerie. At least, those that do come in like that, are rarely buying things for an imaginary girlfriend! And besides, she whispered, your slacks are a bit tight, and when you bend over, I can see your garter straps!" Oh My GOD! I had forgotten all about the perfume, earrings and nail polish! No wonder that man and his sons treated me like a wimpy pansy, I made sure they knew I WAS a wimpy pansy! I had been walking around this mall for over 5 hours! I has shopped, eaten lunch, and everywhere I went, I was advertising that I was an effeminate sissy. I wanted to die, right then and there. "Look," my pretty little truth-teller said, "Don't freak out! The earrings are small, and since lots of guys wear earrings, no one really looks at them, unless they are some kind of huge, gaudy skull or something! And your nails are light pink. Sure, they're shaped and painted, but when you walked in, both of your hands were in your pockets. I don't think anyone else in this whole rat maze of a mall even noticed. I noticed, because I look for things like that. A man buying for himself will most likely get the wrong sizes, and I like to help. When a customer gets good service, they buy more, and come back, which means my commission is bigger. So don't worry, little one, no one noticed, and I'm not telling!" I really didn't believe her, but my psyche desperately needed to believe her. I ended up buying the whole set, along with two pair of white stockings. Sarah, the clerk's name, actually led me back to the dressing area, and then past it, on the back store room. She led me behind a curtain, telling me that this was where they fit some of the customers who couldn't really go into the changing booths. She made me remove my shirt, oohing and awing over my pretty camisole, and then made me take it off and try on the peach silk one. It floated down over my body, and fit just perfectly. Just loose enough to flutter a bit, but no so loose as it looked over sized. I took the silk cami off, and replaced it with my own. But, before I could get my shirt back on, Sarah demanded to see what else I was wearing. Here was a beautiful girl wanted to see my lingerie! I was embarrassed, and hard as a rock! With a blushing face, I undid my belt, and lowered my trousers. She just looked at me, and smiled, telling me how pretty I was. Then she asked if I dressed for a boyfriend or a girlfriend. I mumbled that it was a male. She just giggled and asked me if he was the dominate, and then corrected herself, saying that, "Of course he was the dominate!" Giggling, she told me to get dressed, and she would ring up my purchases. I left the store, and the mall, certain that I was so red in the face that if the power had gone out, everyone would be able to see their way by the glow! I slunk out to my car, and drove off, stopping only at a drive-thru to pick up a couple of chicken sandwiches and a side salad. When I got to my apartment, there was a small box on the doorstep, left by UPS, and a note stuck in the door jamb. I unlocked the door and went in, opening the note as I did. It read: Mr. White: Your employer called today to let us know that you were being transferred on very short notice. While we do not usually let a tenant leave in the middle of a lease, in this case, there will be no problem. Please leave your keys inside the door when you move on Saturday, and we will come in the following week to assess any damages, and will forward the appropriate portion of your security deposit to your boss, Mr. Jenkins, to forward on to you. Thank You, William Bills, Manager I was moving on Saturday! Well, I knew it was coming, but everything seemed to be moving so fast! I had just made the decision to go to the adult book store the previous Saturday morning, and already I was committed to moving into the house of my employer, and to being his sissy slave bitch! What would mother say about all this? I went into my bedroom, head spinning, and absently began to open the small box that UPS had delivered. OH SHIT! It was the chastity thingie! I read the box, then the directions, learning that this was a CB-3000, and that I had the choice of a padlock or a numbered little zip tie. Remembering my instructions, I called Master, and left a message on his phone that the "device" had arrived. I got an immediate text message to strip to my lingerie,put the thing on, and lock it, take a picture with my phone and send it to him. I was also told to put the keys in an envelope and mail to him the next morning. A text a few seconds later told me to put a butt plug in, and leave it in for an hour, as I needed the practice! It took a bit of struggle to get the thing on, and once my penis was trapped in the pink plastic tube, I was less and less sure that I liked it. Almost as soon as I got it on, I felt the need to masturbate. So, I locked the little lock, took and sent the picture, and took it back off. With that, I lay down on the bed, and got into the fetal position. I took the smallest butt plug and popped it into my backside, expecting great pain, but getting only a bit of mild discomfort, and a sort of, "full" feeling. With that done, I fired up my laptop, and began surfing for stories about sissies on Fictionmania, one of my favorite web sites. I found one that fit my fantasy, and scrolled with one hand, while I played with myself with the other. It was a very long story, and I brought myself to the brink of orgasm several times, but each time held off. When I finally erupted into my hand, my heart was madly pumping, as though I had just run a mile. I relaxed back into my pillow, absently licking the copious amount of cum from my hand, and allowing my breathing and heart rate to return to normal. I eventually got up, washed my hands, wiped my penis clean, and re attached the chastity device. I had no sooner clicked the lock and pulled up my panties when my phone rang. It was Master. "Sissy," he barked, "You have ten seconds to take a picture of your pathetic cock and send it to me, and it had damn well better be locked in your device!" With that, he hung up. I quickly grabbed a selfie stick that I had received from a "Secret Santa" gift exchange at work, attached my phone, and took the required picture. As I pushed the share icon, it occurred to me that the picture not only plainly showed me wearing lavender lingerie, showed my penis locked into a pink plastic chastity device, showed my face, but also my pink room, in all its glory. Whatever pictures Master may have taken, I had just snapped a picture that, all by its little self, could sink me if released to the public. I watched a bit of TV, and around nine, went to bed. I slept fitfully, though. I had gone to bed too early, and the plastic cage around my cock was a constant reminder that I had willingly given up my life to serve someone else. The smooth satin sheets and my long pink nightgown no longer felt liberating, they felt like a ball and chain, weighing me down, pinning me to the mattress. I finally got up, drank two healthy shots of brandy, and dropped back into bed. Morpheus eventually overtook me, and I slept without dreams. I woke up about eight on Thursday, slipped into a white satin dressing gown and white mules with three inch heels, and made my way to the bathroom, where I discovered that part of my discomfort the previous night was the fact that I had never removed the butt plug! I was terrified! I had allowed this thing to be in my bottom for over 12 hours, and I just knew that the pain of removal would be horrendous! I sat down on the toilet to pee, and tried to decide what to do. Without thinking about it, I started to "break wind," and the plug simply popped out of my bottom, and splashed into the toilet! There was no pain, and other than my having to reach into a toilet to recover the plug, and then wash it and my hands, no discomfort. Amazing! I decided to take a long, hot bath, and at the last moment, grabbed the three dildos to take into the tub as "bath toys." As I relaxed into the hot, scented bath, I began to gently probe my bottom with my fingers. I found that the liberal use of the bath oil acted almost as a lubricant, and my finger slid up inside, easily. I grabbed the small pink gel dildo, and began to slide it in and out of my back door, loving the feeling it gave me. After a few minutes, I grabbed what I thought of as "Mama Bear." You know, Baby Bear (My small pink dildo), Mama Bear, (the middle size), and Papa Bear (The large, black, lifelike penis that so far, had only been in my mouth, and even that was almost too big! "Mama" was about the size of a man's 7 inch cock.) I started to force Mama Bear up my behind, and found that force really wasn't needed. It didn't slip in as easily as the small one, but did so without much effort, and with no pain. After my bath, I lubed myself, and worked "Mama" inside me. Then, since this dildo didn't have that thin neck a butt plug has to hold it in, I put on a thong bathing suit bottom, using the heavy spandex and Lycra suit to hold the dildo inside me. I could have used one of the bigger butt plugs, but for some reason, they didn't feel as good. Maybe is was in my mind, since the dildos looked like cocks? I decided that today was going to be rest and relaxation day, and even though it was only just before eleven, I removed the dildo, and cleaned myself up. I threw on some boy clothes (Dress slacks, white shirt, oxford shoes, not much else left!) over a pair of panties and camisole, and went to the liquor store. I picked up a bottle of dark rum, some Pina Colada mix, and then headed for the local Panera Bread, where I picked up something for lunch. On the way home, I passed a discount furniture store, and saw a huge mound of bean bag chairs on sale outside the door. I stopped, and payed the $29.99, figuring that a folding chair in front of the TV wasn't going to do it, and I didn't want to buy anything expensive that I would only use for a day or two. Soon, I was shucking my boy clothes. Then I moved into the pink room to dress. Grabbing another clean diaper, I folded it, slipped in the doubler pad, and pinned it on, tightly. Yellow plastic pants with the obligatory satin outer shell went on next. White nylon and lace ankle socks, white patent Mary Jane shoes, yellow satin training bra, and yellow satin frock just about finished the process. I thought about it a moment, and decided that today was my day, and I would wear as much, or as little as I wanted. I did slip on a matching satin bonnet, although this one was sort of a cross between a hair band and a bonnet. Instead of completely covering my head, this one was only about 4 inches wide, very lacy, but still tied under the chin like a bonnet that completely covered the head. Dressed for the day, I made a pitcher of Pina Coladas, without using a blender and crushed ice. I just popped the pitcher in the freezer to get cold. Then, I grabbed a cup of coffee, and plopped down with my take out lunch, and fired up a movie. An hour or so later, I went back to the kitchen, transferred some of the Pina Colada to my baby bottle, moved the pitcher to the fridge, put on a pair of white satin baby mittens, and went back to finish my movie. By two that afternoon, I had watched two movies, and several TV shows, had consumed far more of the rum drink than I had planned on, and was sound asleep on my bean bag, with a bottle clutched in my mittened fists, and a soggy wet diaper. I was awakened sometime after six by my phone. It was Master, telling me to be ready at eight the next morning. I was to wear my lingerie, and heels, but nothing else. "Be ready to pack up and move," he said, and hung up. Looking around, I decided to throw the dirty diapers into the wash, and then do any other laundry that needed doing. By nine, I had all my clothing folded and ready to go, needing only some boxes. I slipped between the sheets, wearing my long, ivory satin with baby blue ribbon trim nightgown, and fell asleep. My alarm went off at a little after six, and I jumped into the shower, giving myself a quick enema there. Clean, inside and out, I put on the lingerie I had laid out for the day. Of course, it was the new peach set from Victoria's Secret, white thigh-high stockings hooked snugly to the garter straps, white nylon ankle socks with white lace and a cute satin bow in the back, along with my white high heeled pumps. A pair of white satin gloves with lacy cuffs, white lacy choker, and a sheer white peignoir over all, and I was done. I put on some perfume, pink lipstick, and touched up the pink polish on my nails, and then sat down with a cup of coffee. I looked around at my almost empty apartment, and realized that this would be my last day of living here, my last day, at least for a long time, of living by myself, and my last day of being a free man. Starting in just over thirty minutes, I would go from free man to kept sissy slave. I loved the idea, even though I was having a lot of second thoughts, and a whole slew of "What ifs?" were running through my head. The doorbell rang, and almost at the same instant, I heard a key in the door, as Master let himself in. I had jumped to my feet, from the only piece of furniture left, my folding chair. Without a word, he strode over to me, and grabbed at my crotch. Smiling as he felt the chastity device, he looked me in the eyes, and then grabbed and kissed me like there was no tomorrow. I melted into his arms. When we finally came up for air, he told me that I had to be a very good girl for him today. I told him I would be, of course! "Now, Amanda," he began, "I have hired a moving company to come to clear away your clothing and bedroom furniture. You now have two choices. You can walk out the door with me, right now, dressed as you are, and allow me to drive you to your new home..." 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A sissy called Jezebel Part VII - Jezebel has finished hir tour with the Head Mistress into the secretive dungeon/reform school below the fair walls of the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. But is the Head Mistress entirely done with Jezebel? Additionally, what ever does one learn in a 'sissy life skills' class? I require the gurls in my harem to crawl on the floor at home and in private at the office. So get on...

3 years ago
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Sissy Prudence Part 3

Sissy Prudence (Part 3) (by Sissy Caroline) Section 1 "That's our Sissy Prudence in the garden. Isn't he a delight?" Bridget looked out the window and, despite the fact that boys were not really her interest, she found the sight presented to her was quite exciting. She had never thought that a boy in a dress could be such an erotic fantasy. Prue was working in the garden, which was something he now really enjoyed as a break from his duties inside the house. Not that he was...

3 years ago
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Americas Next Top Sissy part 3

After waking up, Jim finds himself in a feminine bedroom with the 11 other naked men. When the Nurse from the previous night enters the room dressed in a leather cat suit and introduces herself as Ms J, she wakes the men wake up and they soon learn to behaviour or implants in their bodies will make them. Now forced to wear ultra feminine clothes and wait holding each others hand for the looming elimination! Part 3 Jim is standing in the middle of the bedroom waiting for Ms J...

3 years ago
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Throwing a Halloween PartyChapter 4 The Party Part Deux

After breakfast the next morning, we all sat and talked. "Daddy, thank you for making love to me, but I want to be true to Caleb, I hope you understand," Katy said. "I had been thinking of you that way since our last Halloween Party. That Supergirl outfit really fit you ... well," dad said. "Mom, I need to say to you that at that same party, I realized how beautiful my mother was. Katy even told that me to call her Louise a few times when we were making love. It was wonderful, but I...

2 years ago
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A sissy called Jezebel Part VI

A sissy called Jezebel Part VI - Jezebel's inspection has been completed at the Head Mistress's office of the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. Jezebel is taken by the Head Mistress into the secretive dungeon/reform school below the fair walls of Templeton. All sorts of secrets and surprises are revealed. Headmistress Saxon looks at me. "What class did you just miss?" "Deportment, Headmistress." Forty five minutes...

2 years ago
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Sharons Mistress Throws a Sissy Party

Sharon’s Mistress throws a Sissy Party(Prior chapter is Sharon’s Sissy Saturday)The next morning Mistress was kind enough to let me sleep in, but an alarm above the door to my little cell went off at 6:30, rousing me from a delicious dream of being naked and fucked in the woods by a handsome, dark-haired man who kept me as his personal sissy slave slut. I woke with the sensation of his hard cock filling my dripping pussy, and I realized I was still leaking cum from my day in the booth. I...

3 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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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."...

3 years ago
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Cometh the Sissy Part 1

Cometh the Sissy (Part 1) Stevie "No. No fucking way." "Ahh, c'mon honey. It'll be so much fun! It's about me not you. I just need you there as, well, sort of a training aid. I promise you that you'll love it." "It's gross, seriously, some fat old man, what the fuck are you thinking about?" "It's about power. Control. Desire. I want to see if I can do it. You'll out all day and I'm doing my online classes and shit, there's only so many dildos and vibrators. I want to...

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...

2 years ago
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Americas Next Top Sissy Part 2

Waking on a TV set, Jim finds himself volunteered to be a contestant on a strange show... 'America's Next Top Sissy'. Having been pierced and photographed Jim is left in a dimly lit room with 11 other men all humiliated in the same way. Part 2 Waking with a start, Jim sat up and instinctively covered his naked body as best he could with his hands. After a few seconds Jim realised that he was no longer bound to the gurney but in a bed. With the memories of yesterday fresh in his...

4 years ago
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Becoming a Sissy Part 3

Third instalment. Apologies it has been slow until now, but things progress a lot. In part three. We start with Tom, getting some of his background and thoughts on Peter and then back to Peter's voice.Tom's story.Myself and Peter had been friends since we were in school together were we had an interest in supporting common which really kept us as friends for years and years. We finished school, went to college got our first jobs and settled down all the time being in touch with each other,...

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