Auntie's Servile Sissy free porn video

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Auntie's Servile Sissy by Throne First Jerry's dad had one of his 'nervous episodes' and was packed off by his second wife to Fairhaven Fields, a lovely place in the country where he was watched over by the staff. Then his stepmother decided to take an extended vacation with the most recent of her lovers. Though Jerry Collins had just turned 18 and should have been capable of living by himself, that wasn't what happened. Not that the family couldn't afford it. They had money to spare. But his birth mother had always sheltered him, as he was rather a delicate boy, short and slender and pale, with skin that many girls would envy, and a face that was a bit too pretty for a guy. So, it was decided he would live with his Aunt Lavinia, who he had never met. There was certainly room for one more in her palatial country home, far from any neighbors. Plans were made and he was sent off in a sleek car with a professional driver. Jerry had been deemed 'too uncertain' to even take driving lessons. He arrived at the impressive, gothic-styled home, shortly after dark. The car followed the long circular drive to the columned front entrance. When the driver opened Jerry's door, the teen got out hesitantly. He brushed back his collar-length blond hair with one slim hand. The driver took his plaid overnight bag from the trunk and accompanied him up the steps, and even worked the heavy brass doorknocker for him. When Alfred, who ran the household for Lavinia, answered, the bag was handed to him. He was tall and dignified and had a dark mustache. He wore a three-piece suit. Jerry glanced back at the departing car, which was his only link to his old life. Alfred gave him a thin smile, introduced himself, and invited him inside. "Your Aunt is waiting for you in the library, through that door on the right," he said. "I'll take this bag to your room." Jerry clasped his hands at waist level and took small reluctant steps to the indicated doorway. When he entered, he saw built-in book shelves, glass-fronted cases that contained decorative antique figures, plenty of dark ornate furniture, and exquisite decorated carpets. Across from him, in a throne-like armchair, sat a full- figured, middle-aged woman. Her dark hair was up in a tight bun at the back of her aristocratic head. She had on a white blouse with puffed sleeves and a high lace collar. There was an ivory cameo at her throat. She wore a long skirt. Her legs were encased in dark stockings and on her feet were shoes with two-inch block heels and square toes. She had a wide face, with high cheekbones and a hint of a second chin. He stood six feet from her, shifting his weight from foot to foot, as she examined him up and down. At last, she said, "I am your Aunt Lavinia. Welcome to my home. I'm sure you will be very happy here." "Thank you, Ma'am." "You came all this way in that shirt and those slacks. Why don't you change into something fresh?" "Well..." He separated is hands, to rub his sweaty palms on his thighs. "...mother had the housekeeper pack for me but she only filled one small bag." "Oh my." Lavinia stood up. She was tall and buxom. "Your room was previously occupied by Clarence, the son of a friend of mine. There are some clothes that he didn't take with him. And he was short, with a small frame, like you, so I'm sure whatever you find will fit. Alfred should be back any moment to... ah... here he is now. Alfred, would you show Jerry to his room? And pick out something for him to wear?" "Of course." He gave a nod that was like an abbreviated bow. Alfred turned away and left, with Jerry automatically following him. They went up a staircase and along a landing. When the two of them entered the room at the end, Jerry was surprised to find that the decor was awfully girlish. The dresser and a chair with a scrollwork back were both white. The narrow bed had a canopy, with ruffles around its edges. Even the framed pictures on the walls were less than appropriate for a boy in his late teens. They were images of fairytale castles and unicorns. On the other hand, Jerry's mother had never included anything overly masculine in his room at home. On the bed was his lone bag, now opened. He saw that it contained almost nothing. Short-sleeved pajamas, slippers, several pairs of jockey shorts in pastel colors, and a brand-new bottle of cologne, along with his tortoise-shell comb and brush set. In a small voice, he said, "Aunt Lavinia said you would find me something to change into." Instead of giving him a nod, Alfred merely raised and lowered his eyebrows. He went to the closet and then the dresser. What he laid out next to Jerry's bag were a sleeveless undershirt, except that it was pale green, and a belted, yellow, dressing gown, except that there were embroidered flowers down both lapels and around the bottom. And the belt had fringe on its ends. Alfred selected a pair of Jerry's underpants that matched the top. He took the plain slippers from the bag and held them at arm's length, as if they were something unacceptable. Then he went back to the closet and, from its floor took a pair of slippers that were the same color as the robe and featured similar decorations. "There you are," he said. Then he left with the rejected slippers. Jerry undressed slowly. He put on the selected items. In the adjoining bathroom he found a hamper for his discarded underpants. There was a full-length mirror on the back of the door, in which the new arrival examined his appearance. At least the colors went together, though the combined effect was less than masculine. He fetched his brush to maintain his hair, which he had been taught to give a hundred strokes, at least once a day. When he opened the cologne, to dab a drop behind each ear, and another at the hollow of his neck, he was disappointed to smell that it was more flowery than what he was accustomed to. Jerry told himself that these were just details, which could be worked on later. He was going to be living here for an indeterminate length of time, so he wanted to get off to a good start. Alfred came and gave him a quick onceover, appearing to approve. Then he ushered him back to the library, where Lavinia had a lamp next to her chair turned on and was reading a small volume. She looked up from the book and tilted her head slightly as she observed him. "You look comfortable," she said. "Well, I suppose so. It's just that..." He gestured toward his clothes. "What?" "I'm just saying... What I have on isn't exactly manly." "Clarence never complained about them. He was quite pleased... eventually." "Okay," he responded, with just a trace of sullenness. "Fine. Now Alfred will show you to the kitchen, where Cookie has prepared something for you to eat before bed." "Bed? But it's not that late." "You've had a stressful day. I think the time will be appropriate." He made a petulant face. "All right." She told him, "Wouldn't it sound better, if you were to say, 'Thank you, Aunt Lavinia'?" "I..." He exhaled and his narrow shoulders sagged. "I'm sorry. Thank you, Aunt Lavinia." "Much better." She waved her hand dismissively. "Now run along." Jerry followed Alfred to the kitchen. Cookie turned out to be a corpulent woman with short blond hair, wearing a voluminous apron and short chef's hat. She had a faint accent that he couldn't place. After she motioned him to a small round table and he sat, she set a large bowl before him. It contained some kind of visually unappealing mush. The smell wasn't bad, but it wasn't good, either. The handle of a large spoon protruded from the bowl. "Eat up," Cookie advised. "It's good for you. Lots of fiber." With her and Alfred looking on, he didn't have the nerve to question what he was being fed. Instead, he took the spoon and scooped up a heaping mouthful. As he pushed it between his lips, he found the taste was bland. And it wasn't much warmer than room temperature. Alfred crossed his arms. Cookie put her hands on her wide hips. They kept staring as she shoveled more of the unappetizing glop into his mouth, smooshed it around, and swallowed, over and over. Not until the entire bowl was empty, and his stomach felt distended, did Cookie busy herself with other tasks. Alfred gave Jerry an inscrutable look and motioned for him to follow. The servant led the guest back to his room and allowed him time to brush his teeth and wash his face. Then he went to the dresser and, from the bottom drawer, took a short nightshirt. Jerry was even less pleased with this than he had been with the robe. It was pale pink and of some thin material. Instead of having a round cut-out for his head to pass through, it featured two narrow straps that went over his shoulders. There was a folding screen in one corner. Because Alfred hadn't left the room, Jerry stepped behind it to change. He was uncomfortable being naked with that man present, even though there was a barrier between them. When Jerry was in the sleepwear, with everything else neatly folded and set on a chair, he reemerged. Alfred gave him a curt nod and departed, closing the door. Jerry slipped under the covers. His pillowcase was edged with ruffles. There was a faint scent of perfume on it. He pulled the sheet and blanket up protectively under his chin. As he wriggled around to get more comfortable, he spotted something behind the nightstand, against the wall. Reaching into the narrow space, he was just able to touch whatever it was with his fingertips. After some picking at it, he moved it closer and was able to pinch it with thumb and forefinger, to get it out. Oh my. It was an adult magazine, presumably hidden there by Clarence, the room's previous occupant. Jerry stared at the glossy cover. It featured a busty woman in only bra and panties. Next to her was a man in nothing but a posing strap, which emphasized that he was considerably well endowed between his legs. Jerry thought about his own, much smaller member. He let one hand drift under the covers to touch what he had there, and made a soft purring sound. There was a certain habit that Jerry had practiced in very private moments. Usually, he could control himself as needed, but the presence of that magazine charged up his inner lust. His attention flickered back and forth between the woman and the man. He was having a physical reaction to the visual stimulation. His tool grew hard. He gave it a squeeze, closed his eyes, and savored the experience. Then he released his hold so he could have two hands on the magazine as he dared to open it. Inside, there were pictures of the man and woman with their clothes off, joined by another naked couple. The men were stunningly erect. Jerry licked his lips. Familiar tingles erupted all over his body. He squirmed his hips, folded back the pages, and got a one-handed grip on the periodical. He put a different single-hand grip on himself and gave a few tentative strokes. It had been a while, with all the chaos in his life at home, since he'd had a chance to do this. The covers were too heavy, so he used his feet to work them down, over his chest and pelvis, along his legs, to end up bunched up below his feet. He had nothing on under that brief nightshirt, so it was simple to yank it up in front and gain full access to not only his groin, but also his smooth hairless chest. He switched between pumping his stick and toying with his nipples, the alternating technique guaranteed to prolong his pleasure. Jerry held the magazine close to his face, shutting out any distraction from the rest of the room. His breathing accelerated. That unmuscular chest rose and fell faster. He broke away long enough to turn another page. This time he found himself staring at a photo of the two male participants, facing him and reaching across to each grip the other's rampant cocks. He was so surprised that he didn't try to move on. Also, he was far enough into his solo ritual that he couldn't stop. Jerry mewled loudly, arched his back, and moved his hand faster. Half a minute later he was rewarded with the ecstasy of an ejaculation, and the accompanying thrill it provided. Warm semen landed all over his soft tummy. His breathing decelerated, he blew out through pursed lips, and swung the arm holding the magazine out to the side. As he did, he was met by the heart-clenching sight of Alfred, framed in the open doorway. He was holding a small tray, on which sat a glass of milk. "Young man," he said sternly, "I will need to take you to see your Aunt." "NO!" Jerry blurted. He realized his tone was too strident and modified it. "I mean, please don't. This is just... um... something I almost never do." "No matter," the man said officiously. "Please get out of bed. And hold your nightshirt up in front, so you don't get that mess all over it." Close to tears, Jerry kept the garment high and away from his body as he sat up, swiveled around, and hung his feet over the side of the mattress. He stood up. His face was hot from shame. Alfred summoned him with a few twitches of his bent finger. Jerry followed miserably, wishing he could run away and hide. Ejaculate ran very slowly down his abdomen and into his fine, pale pubic hair. When they got to the library, Aunt Lavinia had set her book aside and was resting her eyes. Alfred made a throat-clearing sound and she opened them. They grew wide, though her expression remained set. As Jerry came closer, she frowned. "This is inexcusable," the full-figured woman said. "I was entrusted with your care, and this is how you respond? I will be very unhappy to have to inform your mother. I hope she doesn't have to cancel her trip, to come and get you." "What? No. You can't tell her. Please. I'll do whatever you say. Just don't tell Mommy." Lavinia considered that. She decided, "Well, there was a device we acquired, because Clarence had a similar problem. He left here wearing it but, if I remember correctly, we bought two of them, and the other one is still available. It was too small for him but might suit you perfectly," she concluded, eyeing his small flaccid penis. Jerry pressed his knees together. "Can I see whatever it is, first?" "If you are going to make demands," she cautioned, "I will absolutely be obligated to call your mother." "Okay. I'm sorry. Anything you want is all right." "I'll give you two weeks. If you don't show the correct behavior, I will still make that call. Between the device and certain changes in your wardrobe I can -- I hope -- adjust your attitude as much as is needed." "I'll cooperate. No backtalk. No anything. Okay?" "We shall see." She said to Alfred, "Will you go and get that item?" He gave one of his nods and left the room. Jerry was on display, more nude than covered, while they waited. Alfred returned, holding a short metal tube, along with a ring that was less than two inches wide. Lavinia said, "This will fit over the offending organ and prevent a repetition of that disgusting act you committed. Alfred can put it on you." "Hey," Jerry objected. "I can't have a man touch me down there." "Already you are protesting, breaking your promise to be amenable. But I am willing to be lenient in this one matter. Alfred, would you ring for Cookie?" Jerry cringed. He pressed his thighs together and drew in his elbows. "Please. I mean..." He ran out of words. At the same time, Alfred went to a narrow alcove in the paneled wall and yanked on a bell pull. His action was echoed, from another part of the house, by a ringing sound. A minute later, Cookie came bustling in. Her hat and apron were gone. Seen without them, she was attractive in an overly curvy way, her generous bust stretching the front of her blouse. She had on a billowing skirt, supported by a wide belt. Draped over the belt was a hand towel, presumably for drying her hands after she touched anything wet. "Cookie," Aunt Lavinia said, "young Jerry has forced us to put him into chastity. The boy is too squeamish to let Alfred put the device on him. Would you mind doing it?" The cook's eyes lit with a devilish gleam. "Not at all, Ma'am. 'T would be fine." She came forward and took the hand towel from her belt, using it to wipe Jerry's front, down to and including his genitals. Then she draped the towel over his shoulder, so close to his face that he could smell his own semen. Cookie accepted the chastity from Alfred. She squatted down and fitted the ring over Jerry's three-piece set, passing his testicles through it one at a time. The process was excruciatingly shameful for him. Next she stretched out his penis and let it snap back. He was so upset, that it didn't stiffen. The big woman deftly fitted a metal sheath over his organ, compressing the soft tissue until it fit into the short tube. Turning his eyes down, he saw that his organ was now a mere nubbin. She fitted the tube to the ring and turned the key that was already in an attached barrel lock. When she rose and handed the key to Lavinia, a shudder of helplessness ran through Jerry. As Cookie retrieved her towel, she smirked at him. The Mistress of the house thanked and excused her. When the cook turned to leave, Jerry saw that her bottom was as impressively large as her bust. "Now," Jerry's aunt said with only a suggestion of reproof, "that will keep you from any more self abuse." He was still holding up his nightshirt. She told him he could lower it. When he did, it made him feel only slightly better. Not knowing what else to say, he said, "Thank you." She chortled. "You're welcome. I imagine you want to find out if the device is as effective as I say. Go on, then. Try to arouse yourself." "Oh, I couldn't." "I insist." Alfred narrowed his eyes. Jerry bit his lip. The young man lifted the sleepwear up just enough to expose his locked cock. He experimentally tugged on the metal encasing it. Though his member wanted to erect, it was frustrated by its cage. At his aunt's suggestion, he got his other hand under his nightshirt and played with his nipple. That made him want to get stiff even more, but again his body's effort to do so was futile. Jerry whimpered from both embarrassment and the fact that he would be able to gain no sexual release unless she deigned to give him the key or let someone else, like Cookie, use it. "So," she declared, "we can all see that it works. But preventing your filthy habit isn't enough. We must also deal with the motivation behind it. I'm afraid you suffer from delusions of masculinity, Jerry. You think you're one of those young roughnecks who has an excess of testosterone and must relieve the pressure which it causes to build up. Yet simple observation of your appearance and manner makes it clear that you are quite the opposite. Therefore, I will begin a program of dressing therapy. Once the outer you has matched the inner you for a period of time, perhaps a month, you should be convinced of who you really are." "Do you mean you're going to dress me in girly clothes?" "I mean precisely that." "But I'm not a sissy." "If I may interject," Alfred offered. "When I found him deep in the throes of onanism, the lewd magazine he was using as an aid, was turned to a page featuring two men, in a compromising pose." "And your mother expressed concerns about your ability to function in the real world, Jerry, because of your lack of maleness. So this will be the best thing for you, all around." "But I don't want to be a girl," he protested weakly. "You won't be one," she pointed out. "You will be a sissy. Please try to understand the difference." He whimpered and hugged himself. What else could he do? He had almost no male clothes, and no means to go anywhere if he left. He didn't even have anything on under that less-than-masculine garment. Jerry lowered his eyes in defeat. He whispered, "I'll try to cooperate. But if it doesn't work, I can go back to dressing like myself, can't I?" She conceded, sounding perfectly reasonable, "Most certainly. And I like that way you sounded, just now. Please speak just as softly while you're undergoing your therapy. Understood?" Still using the wispy voice, he agreed, "Yes, Ma'am." "Very good. Now let's get you properly attired." She asked Alfred, "When your niece worked here a while back, I believe she left some clothes, because she intends to return. Jerry is about the same size as her. Do you think she'd mind if he wore her things?" "Not at all. In fact, I'm confident that she would be honored to help in any way with his rehabilitation." "Excellent. Please begin transferring her clothes from the room she occupied, to Jerry's dresser and closets. Choose something for him to change into. And leave only those of Clarence's clothes that you deem appropriate." "At once." Jerry thought he spotted a malicious glint in the man's eye before he turned away. As soon as Alfred was gone, Lavinia went on, "We also have to deal with the possibility of you expressing any male aggression. There are two ways to diminish that risk. One is to humble you. The other is to drain some excess energy with physical tasks. Both of those goals can be achieved simultaneously by having you do some housework, while wearing appropriate attire. The woman who usually takes care of those chores has been off for a week, so there is a backlog of jobs to be done. She is due to return early tomorrow, at which time I will have her direct you and make sure you know what you're doing." Jerry was feeling worse and worse. At the same time, surrendering power and letting others make decisions for him had a strange appeal. Even the idea of being feminized played into that attraction. It would be so nice to not have to run his own life. Still, the thought of being dressed in a girly fashion unsettled him. And very soon that concern would become a reality. Before he could think much more, Alfred reappeared. He announced that there were enough of his niece's clothes now in Jerry's room, along with a few items from the previous occupant, that the boy could get changed. Alfred turned on his heel and walked away, with his charge trailing obediently behind him. Alfred glanced back and halted. He said, "That flatfooted walk is unattractive, and doesn't fit into your new image. Please take small steps. Put one foot in front of the other. And relax your body, so that your hips take on a natural sway." He crossed his arms over his chest and eyed Jerry from his superior height. "Let me see you do that." The young man pushed back his blond hair, put his hands at his sides, and began to move in the way that had been described. Alfred advised him to hold his arms out slightly and let his wrists go limp. "Chin up. Shoulders back. Good enough for now. Make sure you maintain that gait. It's an important part of the help your aunt is giving you." Alfred offered a few more suggestions for how Jerry should climb the stairs, and even advised him on opening the door to his room. As they went in, he saw several pieces of clothing spread out on his bed, as before. But this time they didn't merely suggest feminine wear. They were unquestionably a girl's clothes. And they were out-of-style, from the full-cut, pink panties and short, shimmery slip, to the retro party dress, green with yellow cabbage roses all over it, and capped sleeves, that made him think of mid-century fashions. There was even a red pillbox hat. Had Alfred's niece really worn these things? "Would you like help getting dressed?" Lavinia's employee wanted to know. "No, thank you," Jerry said abruptly and too loudly. He resumed his modified way of speaking and went on, "I'll be fine. Maybe you can just make sure I'm doing everything right." "Naturally. Whatever you need." Was there condescension in the words? Alfred moved back, as if to assure Jerry that he wouldn't step in unless asked. The folding screen was gone. Alfred must have removed it. The reluctant visitor pulled the nightshirt over his head, with the man watching. When he picked up the panties, he found they were made of some satiny material. Quickly stepping into them and getting them all the way up, he was relieved to be at least partly covered. Next came the slip. Jerry got it over his head and let it slither down his body, caressing his skin as it went. The dress was easy to get into but he couldn't button it up the back. He had to ask Alfred to finish the job for him, which the man did dexterously, without a word. Then Jerry perched the round hat atop his head. He checked himself in the mirror and decided that, as much as he didn't like having to dress that way, it was much better then being mostly naked. Alfred informed him, "I put some of my niece's make-up on your dresser, if you'd like to apply a little. As part of your therapy, you understand." Jerry said, "I'm not sure how to do that." "Just try, and I'll give you some tips if you need them." With minimal input from Alfred, Jerry gave himself smoky eyes and a bright magenta mouth. He decided it was too much, but the man who had brought him was acting impatient to go. Alfred pointed to the floor under the bed, where a pair of girl's shoes were peeking out. Jerry put them on. They were shiny red and had pointy toes, as well as narrow, two-inch heels. The young man found he could walk in them if he took even smaller steps than previously. He followed Alfred to where Lavinia had relocated, on the sofa in the living room. He used another bell pull and Cookie showed up, pushing a tea cart. "Now," Jerry's relative said, "let's get you acquainted with proper manners for drinking tea. Sit on that chair across from me." When he went and plumped himself down on the padded seat, Lavinia frowned. She had him get up and sit again, several times. He had to lower himself gently and then cross his ankles. Next she had him get up and pour her a cup of tea. He overfilled the cup and, when he picked it up to give to her, some sloshed out onto the saucer. She shook her head disapprovingly. "No, no, Jerry. You have to move more slowly and gracefully. And never put so much tea into a cup. Now put that one back on the cart and try another." He did better on the second try. When he passed it over, she accepted his effort. Then she told him to pour one for himself. He did and missed the cup with only a few drops, at the end. She had him take it to his seat and sit again. He had to extend his pinky when he raised the cup to his lips. She taught him how to take the tiniest of sips. "You're learning, albeit slowly," she allowed. "Now that we've given you a proper appearance, you'll need the right name to go with it. Instead of Jerry, how about... Jenny? Yes, I like that. Are you enjoying your tea, Jenny?" "Yes, Ma'am," he replied in the girly way that he had been instructed to. "Very good. I'd offer you some of these delicious cookies I'm enjoying, but right now you're on a strict diet. So just relax and let me admire you. Tomorrow morning, as soon as Ellen gets here, she can get you started on your housecleaning." He wanted to object but by then his willpower had ebbed to almost nothing. So he merely smiled and nodded, as if he was enjoying a civilized tea party for two and didn't have a care in the world. By the time his second cup of tea was gone, he felt his bladder making demands to be emptied. As difficult as it was for him, he told his aunt he had to use the lavatory. She explained, "You must ask for permission to relieve yourself. And do it with utmost politeness. Now please make your request, Jenny." "Ma'am," he began in his girly voice. "I'm sorry to bother you. I have to use the lavatory. May I have permission to do so, please?" "That was good enough. Now let me have you wait a bit, to help you learn some physical self control." She sipped her tea and gazed at him over the rim of the cup. A part of Jerry wanted to yell, perhaps to throw a tantrum. This was maddening. But even as flustered as he was, he still had to maintain a calm outward demeanor if he expected to get through this. As he sat there feeling uncomfortable, thoughts of everything that had happened so far ran through his mind. The suggestions which had been made, that he might not be very manly to begin with, kept repeating themselves to him. He smoothed out his dress over his lap and maintained his prim posture. What if that was true? Were his efforts to internally hold onto his maleness going to prove futile? After ten more minutes, Lavinia informed him where the nearest bathroom was, and cautioned him that he should sit on the commode, as a girl would. Wearing the chastity, he realized, would mean doing it that way all the time. He gave her a smile of thanks and left the room, aware of how easily he fell into moving in a feminine way. Having to deal with a dress and panties before he could relieve himself was certainly a new experience. He managed to get through it with no major problems, though there was plenty of shame. When he returned to Lavinia, she told him that he was now allowed to go back to his room to change, and could sleep in his slip and panties. Going from the less-than-masculine nightshirt to those definitely feminine garments had been a step further into his new sissy status, he knew, but he was too focused on walking correctly to think much about it. Alfred accompanied him again, and reminded him to remove his make-up, giving him pointers on how to do it. He also unbuttoned the dress. Once again, Jerry had to change in front of him. Alfred glanced at his watch, reminding Jerry that he was now up later than had been planned. "Goodnight, Miss," Alfred said after Jerry was back in bed. "Goodnight, Alfred," Jerry answered. His soft voice was starting to sound natural to him. The young man tried to sort out everything that had happened since his arrival, and to project ahead to what else might occur. His earlier feelings, about the pleasures of surrender, were now in conflict with his need to not be turned into a sissy. He silently berated himself for masturbating and, worse, getting caught. If only that magazine hadn't been there. And Alfred hadn't brought that glass of milk. How could Jerry's luck be so bad? He reached down and touched the chastity device, barely able to believe that it had been locked onto him. As stressful as everything had been, he wanted to play with his dick again, to relieve the tension. That option was no longer available to him. He would have to work hard to please his aunt, so he could get unlocked. After that, he would only touch himself in that special way when he was safely alone in the lavatory. Alfred came and woke him up the next morning. The tall figure's arms were behind him. Jerry was shocked that the man was accompanied by a woman who was not much older than Jerry himself. Dressed in a white, high-collared blouse and charcoal pencil skirt, she was tall, with angular features, and a trim figure. Her reddish-blond hair was worn short. "I am Ellen," she said, by way of introduction. "The maid. Your Aunt has informed me that you will be taking over the bulk of my duties until further notice, and that I am to assist you in getting dressed for it, as well as accompanying you to make sure you do a proper job. Are we clear on that?" Jerry decided that he had better keep this woman happy, rather than risk her giving a bad report to Aunt Lavinia. He nodded. "Yes, Ma'am." He was still using his wispy voice. "Thank you." His shows of gratitude, whether sincerely felt or not, were coming automatically. "Very well," she said. "Alfred has something appropriate for you to wear." From behind his back, the tall man brought a dress on a hanger. It was a very short maid's outfit. In his other hand were a tiny apron and fishnet stockings, as well as a pair of shoes. That latter were black, with two-inch block heels. Ellen excused Alfred but stayed herself, to supervise Jerry dressing. He blushed as he began to get out of his sleepwear. It struck him that there were no panties being offered. He meekly inquired, "Should I keep on the panties I'm wearing? Or...?" She shook her head. "You will not wear anything under your dress today. Lavinia feels it will help you learn modest behavior, if you have to be extra careful not to expose yourself." He swallowed drily. "Yes. Thank you, Ma'am. I understand." Taking the dress off its hanger, he unbuttoned it down the back, then stepped into the skirt portion. Next he got his arms through the short sleeves, which were trimmed with lace. He looked helplessly toward Ellen and gestured to the unreachable buttons. "Could you, please...?" "Of course." Jerry saw that he would also need assistance to get out of the dress. Did everything button up the back that way? He sat on the side of the bed and she instructed him on how to roll the stockings up his smooth, hairless legs. Then she had him put on the shoes. Ellen got down on one knee to fasten the buckles, as if not trusting him to manage the small task himself. Then she had him stand, so she could put the apron on him and tie a big flouncy bow in the back. She had Jerry sashay around the room. After that he was told to apply make-up. Under her guidance, he gave himself a more conservative look than the night before. Ellen brushed his hair, parted it in the middle, added some volumizing product, and left it fuller and more feminine. Producing a tiny starched cap, she pinned it atop his locks. Then she took him to the dining nook, where his aunt was just finishing a modest morning meal. Lavinia did not offer him anything to eat. Instead, Ellen gave him a feather duster and ordered him to start by using it on the baseboards of the room. He almost forget himself and pointed out that the job was unnecessary. Stifling any words at the last moment, he kept his mouth shut and went to the corner to begin. It struck Jerry that, if he bent forward from the waist, his skirt would rise in the back. He certainly didn't want to expose his uncovered bottom. So he dipped at the knees and reached out to begin his chore. That made it necessary to straighten up and move to the side, each time he finished a section, which was frequently. If they had allowed him to wear panties, the awkward posture and difficult movements wouldn't be needed. It was frustrating to have to do his job in such an inconvenient way. As he worked himself around the room, his aunt enjoyed a cup of tea. Jerry's tummy grumbled. He salivated. Finally completing his task, he turned to Ellen, who waited expectantly. "Yes," the usual maid said to her replacement. "Now let's get you started on the lavatory. One of them, anyway." Jerry had to wonder how many there might be in such a large place. He followed meekly, to a supply closet. At Ellen's instruction, he hung the duster on a hook. Then she pointed out the tools he would need to use. He was surprised to find that the bucket was small, the scrub brush miniature, and his sponge half-size. Everything was going to take at least twice as long as it should. He suppressed a sigh and gathered what he needed, along with a large plastic bottle of liquid cleanser. Ellen walked him to a large bathroom, much more spacious than the lavatories he had visited earlier. With a few tips from her, he filled the bucket with hot soapy water and set to work, starting higher up and working down. When it was time to do the toilet and floor, with special emphasis on hard-to-reach spots, his muscles, unaccustomed to such exertions, began to protest. On all fours, he couldn't avoid his skirt lifting enough to show more than a peek of cheeks. It was hard for him to care about that any more, as he labored unhappily, shamefully aware that he was dressed like a traditional maid. When he heard Alfred behind him, telling Ellen that Madame wished to see her, Jerry stiffened. He reached back to pull down his skirt, but that didn't work. Alfred made no move to leave. The mortified young man had to keep going, with the motion of his scrubbing arm causing his backside to wiggle side-to-side. He could feel Alfred's eyes on him. Strange tingles ran up and down his spine. At last, Ellen reappeared. She said that, when he was done this room, his aunt would see him in the kitchen. Jerry eventually finished and was permitted to wash his hands and put away the supplies. When he got to the kitchen, Cookie had another bowl full of gruel waiting for him. He sat primly and confronted the food. Taking his first big spoonful, he found it was cold. His aunt was watching him critically, so he didn't allow his distaste for the mush or its temperature to show. The cook gave him a tall glass, brimming with lukewarm water. He alternated drinking and eating. The food seemed to absorb all that water, and by the end his stomach felt overly full. Ellen had him do some more housework, which was unpleasant after such a filling meal. He had to polish silver and wipe down furniture. In a home that size, once everything was done, it would be past time to begin over, especially if Ellen gave him less-than-ideal equipment, as she had done for the bathroom. Feeling more and more put upon, he was then taken back to the kitchen, where Cookie presented him with a sink full of dirty dishes and cookware, a long apron, and big rubber gloves. By the time he had everything washed and in the drying rack, he was exhausted. "Now," Ellen said, "your aunt is ready for you to continue your dressing therapy." Jerry was relieved to be done the chores. His relief was not long- lived. Ellen walked him to his pink and white bedroom. Alfred was waiting. Jerry's eyes went from the tall man to the bed, where there was another change of clothes waiting. All he saw atop the bedspread were a corset, a pair of bloomers, and high-button shoes. The youth stood there with his mouth open. Alfred clapped his hands, snapping Jerry out of that shocked reaction. Ellen told him to strip. He got himself naked - except for the cock-lock, of course. First they put the corset on him. Alfred held it while Ellen snugged up the laces. She kept tightening them, compressing his waist more and more. Then Alfred took her place, bracing his knee against Jerry while he made the garment painfully snug. After he tied it off, he stepped away and gave the youth's bottom a firm swat. Jerry yelped and stumbled forward, into Ellen's arms. His bare chest was pressed against her modest bust. Inside its penis prison, his dick tried to stiffen. It pulsed and demanded to be touched, but couldn't grow at all. Ellen had him sit on the edge of the mattress. The corset hurt his midsection and kept his back straight. She held the bloomers, so he was able to get his feet into them. Then she made him stretch out his arms until he could grip them and pull them up. He got clumsily to his feet and pulled them the rest of the way. They reached to just below the corset. "Walk around the room," Ellen urged him. "Don't forget how you're supposed to move," Alfred reminded. Jerry did what they wanted, but it wasn't easy. At least the room was small. Then they had him sit on the white chair, so each of them could each put one of the shoes onto his feet. They were too narrow and not long enough. There was a buttonhook for each of the dressers, enabling them to finish the job in a relatively short time. He doubted that he could get himself out of either the corset or that crushingly tight footwear. When they helped him to stand, he whimpered. Alfred gave him another hard swat to the fanny, starting him walking toward the door. Soon he was out in the hallway, moving slowly, each step costing him discomfort. His bottom stung. His waist protested. And his feet sent angry messages to the pain center in his brain. They were moving through the house when Ellen decided, "Our Jenny needs more motivation. Please fetch me a crop, Alfred." He hurried off and returned, all too soon, with not only a riding crop for her, but also a swagger stick for himself. As Jerry moved forward, with a sort of feminine hobble, they took turns swatting his bottom. He let out a high-pitched cry each time they struck his vulnerable backside. The thin material of the bloomers was almost no protection. He whimpered as the pain penetrated and spread, until he was fighting back tears. Before he realized what they were doing, his two tormentors had steered him into the library, where Lavinia was waiting, again ensconced in the familiar chair. "Please make them stop," Jerry wailed. "It hurts so bad." "I would prefer," she responded, "that you address me properly. You may call me Aunt Lavinia, or Auntie, or even Auntie Dearest. Let's try all of those." Alfred gave him a slash across both buttocks with his rattan instrument. It was less than two feet long, so the force was well concentrated. It's solid core made it especially effective for leaving marks and creating lasting pain. Jerry sobbed, "Please, Aunt Lavinia, don't let them hit me any more." She told him, "Now try the next way." He hesitated. What did she want? A smack of the crop triggered his mind. Jerry said, "Please make them stop, Auntie." Ellen landed another, across the vulnerable tops of his thighs, where there is less protective padding. He shrieked. "P... p... please, Auntie Dearest. Tell them not to do that." "Well," Lavinia said thoughtfully, "I've tasked them with helping you to learn. If I stop them from doing what they feel is necessary, how will they ever be able to accomplish their goals? So, no. I will not order them to cease and desist. Not at all." To the two who were hurting him, she calmly said, "Carry on." The blows resumed. He was driven out of that room and all through the spacious first floor. When they reached the kitchen, Cookie saw what they were doing. She took a narrow cutting board, one that was shaped to accommodate a loaf of bread, pulled down his bloomers in back, made him bend forward and grip the counter, and gave him half a dozen hard ones on his already striped and bruised rump. His knees started to buckle, but Alfred caught him. He supported the victim with one arm around his torso from behind. With his free hand, Alfred teased Jerry's exposed nipples. The well-dressed man said, "Let's see if this takes your mind off the hurt." Jerry shivered all over. Alfred's expert touch sent currents of pleasure through him. Again, the young man's dick tried futilely to erect. His balls were beginning to throb. His bottom blazed. His middle was pinched so tightly by the terrible corset. And his feet hurt more with every step. "Correcting Jenny is hard work," Ellen commented. Cookie offered, "Would each of you like a bit of brandy?" "That would be lovely," said Alfred, now toying with Jerry's other nipple, wetting his fingers to intensify the effect. Jerry moaned and squirmed, in the throes of sexual arousal. Pain and pleasure became confused in his mind. Alfred got him standing straight. With both hands free, the man touched Jerry's ears, neck and shoulders, the contact teasingly light, but oh so powerful. Jerry's eyelids fluttered. His cheeks were flushed. He kept licking his lips. "Well," observed Ellen, "this one sure perks up when a man touches him." Cookie chimed in with, "Jenny has the makings of a true sissy." Alfred chuckled. "I barely got started before he simply melted. I'll bet he's been hoping some strong man would do that to him for quite a while." Jerry moaned, "Nooooo," but he had to ask himself if Alfred might be correct. The big man ran one finger playfully between Jerry's uncovered buttocks, lingering on the most receptive spot. The corseted boy gasped and pushed back against the questing digit. "Oh, yes," the man touching him concluded. "We have ourselves a hungry sissy, just waiting to have his appetites satisfied. I'd wager that he'll want to pay me back in kind before long, if you know what I mean." The women laughed. Jerry tried to make a disapproving face, but Alfred began kneading his sore buttocks, translating pain into an unfamiliar type of sexual turn-on. Jerry pawed at the waist of his bloomers, trying to yank them up, but his captor simply slapped his hands away. "Bad boy," admonished Alfred. "That could earn you some time across my lap. Of course, it might be less like punishment to you, and more like foreplay." His fingers never stopped moving. "Isn't that right, Jenny?" "No," Jerry whispered. "I mean, maybe. Yes. No. I'm not sure." Alfred chuckled, chucked him under the chin, and gently backed him up to a wooden chair. He sat the young man down on his bare butt. Cookie produced three small glasses and a bottle of brandy. She poured for all of Jerry's handlers and they raised their drinks, to clink them together. "To our girl Jenny," Alfred toasted. "To helping her get in touch with her feminine side," added Ellen. "And spanking those cute buns, every chance we get," cheered Cookie. As the trio enjoyed their drinks, their prey could only sit there, on his tender rear, and try unsuccessfully to sort out everything that was being done to him, including the new feelings Alfred had so effortlessly awakened. In the days that followed, there was more of what he had already been subjected to. He had to wear the maid outfit and spend hours cleaning. The gruel remained a staple in his diet, along with fruits and vegetables, plus some dairy products. Frequently, Jerry found himself over Alfred's firm thighs. The spankings were prolonged, as the spanker traded off administering discipline with elevating arousal levels, until Jerry could no longer separate the two entwined streams of sensations. Wearing male clothing became only a memory. His body language kept evolving, as did his speech, both becoming exaggeratedly feminine. He unconsciously primped and preened. He learned more about applying cosmetics and fixing his hair. Jerry even came to take pride in crafting his appearance in ways that won Lavinia's approval. The smallest compliment from her became the center of an entire day for him. Alfred continued to escalate his handling of Jerry, even massaging his testicles and teasing him about possibly unlocking his chastity. The captive came to feel increasingly dependent on his captors. Jerry lost weight on his diet, becoming positively svelte, which further inflamed Alfred's steadily swelling lust. Often, the older man would rub himself suggestively against Jerry, letting the nephew feel a hard cock through the man's trousers. All three women became erotic touchpoints for the sissified male. But it was Alfred to who his interest was always turned in the end. He tried to resist, to tell himself that he was still straight, to prove that while he was outwardly so girly, inside he remained his old self. Despite all his efforts, it was a losing battle. Jerry's bottled up sexual energy expressed itself in unwanted ways. While he was over Alfred's lap, having his rear end reddened, his thoughts shifted to how the man had touched him immediately before the spanking. When Jerry was given that dirty magazine again, he went straight to the pages that showed the two oversexed guys together. He didn't want to let himself see those photos, but couldn't keep from sneaking another look, and then one more. Other periodicals followed. He was always disappointed when the images were male on female, or girl on girl, but delighted to find fresh ones of homoerotic couplings. He came to a complete standstill when he turned a page and saw two effeminate youths, lying on their sides, facing each other, in the classic 69 position, each with the other's cock in his eager mouth. Thoughts of such scenes filled his mind and disturbed his sleep. He hugged his pillow. Jerry even acquired the habit of fingering his own nipples, taking himself to the heights of auto-arousal, even though he knew that fulfillment was impossible while in chastity. Alfred's hints about freeing him preyed on his mind. He told himself that, if he did something to please the older man, there would be reciprocation, which he needed so badly. Jerry rationalized at a furious pace, with some denial added into the mix, and lots of twisted logic to tie up any loose ends. He saw Alfred with new eyes. When Alfred personally gifted Jerry with a pink, baby doll nightie, the well sissified youth was thrilled. He put it on and modelled it for his benefactor. Alfred stroked the wearer's nipples through the filmy material, until Jerry was nearly weeping from need. When the tall man placed his hands gently on bare shoulders, youthful legs bent and Jerry sank willingly to his knees. He rubbed the front of the man's pants, undid his belt, unhooked the catch, and lowered the zipper. Moments later, Alfred had slipped off his loafers and Jerry helped him to step out of his pants. All that was between Jerry's unnatural appetite and his goal was a pair of boxer shorts. He had felt Alfred's cock often enough to know that it was large, like those in the magazines. Out of his mind with lust, Jerry inched down the final barrier to his target. He was tickled to see that what the man possessed was not only the size he had anticipated, but well made, with thick veins and a full head. Jerry wrapped his arms around muscular thighs and pressed his cheek to the now half-tumescent organ. He turned his face toward it and gave an experimental several licks to the impressive shaft. Soon, with some help from his hands, he had it standing tall, hard and with a slight upward curve. Tingling all over, still not fully understanding what he wanted, Jerry capped the knob with his wide-opened mouth. He closed his lips and sucked. Alfred's answering sigh meant the world to Jerry. He slid his lips along the thickness, taking as much as he could, and cursing his gag reflex when it halted his progress. He gripped the root, unable to stretch his fingers all the way around its girth. Then he simultaneously sucked and stroked. The standing man's hips jerked. He groaned. Jerry pumped and suctioned. All at once, Alfred tensed and shot his load, flooding the sissy's mouth. Jerry swallowed. Just as he was at the apex of his self-celebration, it abruptly hit Jerry what he had just done. His old masculine personality reasserted itself, all at once. He was stricken by guilt and remorse. He had just sucked a man's cock and gulped down his semen. Alfred said, "That let off the pressure. Now let's get in bed and you can really take your time to coax the rest of the spunk out of my balls." Jerry was sickened. He didn't want to do it. He said, "I'm not sure about..." That was as far as he got before Alfred cut him off with, "Or would you rather play some spanking games? I know you much you like those. And I could try pinching your nipples, instead of just touching them. Pinching hard." His words refocused Jerry's mind. The youth still didn't want to do more cock sucking, but the alternative was even less appealing. He also was convinced that, if he endured the punishments Alfred had mentioned, it would still lead to that big rod between his lips again. Either path had the same destination, yet one was shorter and less difficult. The latter was what he chose. Jerry reminded himself that, as much as he didn't want to, it was safer if he convinced Alfred that he honestly desired to give him a second, more leisurely blowjob. "Oh, yes," Jerry purred. "I can't wait to have your magnificent tool tickling my tonsils again." He even made himself giggle like a silly girl. Except that he wasn't that. He was a silly sissy. The follow-up knob polishing and sword swallowing took so much longer. There were kissing and licking of that impressive length. Alfred wanted his balls lapped, so Jerry did that too. Better for him to slurp Alfred's scrotum, than to have Alfred squeeze or slap Jerry's. It went on and on, until the hinges of Jerry's jaws hurt. In the end, Alfred made him pump the rod, while his lips capped the head. When the reclining man spurted, every drop of his spunk went against the roof of Jerry's mouth and onto his tongue, rather than any of it rolling straight down his throat. He forced himself to glug it all down, thinking about how it would be inside him for hours to come. After he had thoroughly cleaned Alfred's enviable cock, the big man pulled him close. He rolled his reluctant partner over, so Jerry's bottom was against the man's groin, and stayed that way as he, Alfred, drifted off to peaceful sleep. Jerry could only lie there, on his side, the flaccid member pressed to the cleft of his ass, worrying about what might come later. That oral encounters were repeated frequently over the next several weeks. Then Lavinia announced that Jerry's mother was coming for a visit. The sissy's reactions were mixed. Mainly, he saw it as a way to escape. Surely she wouldn't leave him here, in this terrible situation. Still, he had become so emotionally needy, with only the other three people in that house able to supply what he required, that it was close to impossible to imagine going back to his former life. He struggled with the conflict, telling himself that, once Mother got there, all would become clear, and he would be free of his tangled urges. Mrs. Collins arrived, swathed in fur, wearing a matching hat, and bedecked with expensive jewelry. Jerry didn't want to be seen in his girly clothes, but they were all he had. At least he was allowed to shed his maid's outfit. Lavinia herself had selected a juvenile-type dress, in pink, with capped sleeves, a ruffled front, and very short skirt. It was accompanied by appropriately juvenile shoes with oversized decorative buckles. He stood in front of his mother with his knees together and toes turned in, hands clasped at his waist. She eyed him coolly. Jerry's mother spoke not to him, but to his Aunt. "I can see that what you said was true, Lavinia. If anything, Jerry - or I should say Jenny - is even more effeminate than you suggested. I suppose you were trying to be kind to me, by playing down just how much of a sissy he turned out to be." "It's true," Lavinia said with a sigh. "In fact, he has started a relationship with my steward, Alfred. At least this way, Jenny has some stabilizing influence in her life." The young man couldn't believe what he was hearing. He tried to speak, but his words came out as high-pitched syllables. "Moth-er, you can't lis-ten to her." He stamped his foot like a petulant child. Jerry hadn't realized just how girly they had made him. Now, as the reality of it hit him all at once, his words became very soft. "I mean, if you would just let me explain..." His mother fixed him with an imperious gaze. "Yes, Jenny?" She used his feminine name as if it was perfectly natural to do. "What is it, girl?" Jerry fell apart. His lips quivered and his eyes blinked. All at once he was sobbing. Impulsively, he turned and tried to run away, but unintentionally went straight into the arms of Alfred. The dress- wearing young man squealed. In a tizzy, he clung to the older man for protection, and buried his face against Alfred's lapel. "This certainly is extreme," Jerry's mother concluded. "So I'll go along with what you suggested, Lavinia. Jerry needs to be married to Alfred. I'm so glad everyone involved is agreeable to that." The intended bride hadn't even been told about this possibility, which had just become a reality. Before he could retreat, Alfred wrapped a protecting arm around him to keep him where he was. Jerry trembled all over. "If I may say something..." Alfred began. "Please," Jerry's stepmother said, "speak freely. After all, you're practically family now." "Well," Alfred went on, "I believe that once Jenny has experienced the physical relationship that comes with being married, she will calm down considerably." Unable to contain himself, Jerry turned his eyes up to Alfred and said meekly, "What do you mean?" "I'm referring to consummating our marriage, dear," Alfred hold him. "Once I take your maidenhead, it will most likely settle your nerves. After all, it's what you've been silently wanting for a long time, even if you didn't admit it to yourself." "My... maidenhead?" Alfred lowered his hand behind Jerry and, unseen by the others, jabbed a stiff finger between the youth's soft buttocks. "Yes, Jenny. Your sissy cherry, if I may speak in the vernacular." Jerry was too stunned to say anything else. After they were wed, Alfred would expect more than those frequent oral attentions. He wanted them to... go all the way. Mrs. Collins said, "I'd like to see Jenny eating her special diet and, I'm afraid, I'll need to witness at least one of her discipline sessions. It's my motherly instinct to be aware of every aspect of the care you're giving her, though I'm sure it's all what's best for the girl." "Of course," Lavinia said. "In fact, he's overdue for a bare-bottom spanking from me personally. I'll be using a hairbrush that I had to purchase especially for that purpose, once we found out how difficult your daughter can be." The youth wished they would stop referring to him as a girl. And he didn't want his Mom to see him having his backside tanned. In fact, it must still be pink from the hand spanking Alfred had given him earlier, after Ellen declared that he had shirked on his maid duties. This was all happening too quickly. His hope for rescue had been replaced by an almost absolute certainty that his situation would not only get worse, but also go on and on. He was wrenched away from his private concerns when his aunt snapped, "Jenny. Come over here this minute. I can see that you're beginning to ignore us again. Obviously, the best thing for you is to have that spanking right now." To Alfred she said, "Would you be a dear and bring me that hairbrush?" "Certainly," he said with a smirking smile. While he was gone, the women chatted about Jerry's dressing therapy. His stepmother declared that she would have some new items sent to the house, ones that would be especially chosen to deny whatever reserves of masculinity he might still be harboring. She even had the inspiration to insist on having a custom maid's outfit produced for him, all in shades of pink. He pictured himself wearing it and cringed inwardly. Alfred returned with the recently acquired hairbrush. Made of dark wood, it was larger than average. Lavinia moved to a wooden chair and sat there, patting the flat of the brush against the palm of one hand. "Well, Jenny?" She gave her nephew a coldly resolved look. "Are you going to come here, or do I have to ask Alfred to drag you by the hair of your head?" "No, Ma'am," he said wanly. "I'm sorry. I wasn't thinking clearly... Auntie Dearest." "Indeed, you weren't." She nodded toward her broad lap. He came over and performed the increasingly familiar act of draping himself across someone's thighs so his bottom could be soundly beaten. Jerry was aware of the difference between how it felt when he was lying on Alfred's legs, or Ellen's, as compared to Lavinia's or Cookie's. His mental musings were interrupted when the woman surprised him with a hard whack to one buttock and then the same to the other. He cried out and gripped the legs of the chair. She paused to let the pain sink in. It was something he had not gotten used to, and believed he never would. When she sensed his muscles relaxing, she laid on another half dozen measured swats, which left him moaning and close to tears. He hated how easy it had become for them to make him cry. It was like an added proof of his lack of maleness. He sniffled. Once his breathing slowed back to normal, she raised the hairbrush again. His nether cheeks had gone from white to pink. Now she delivered a harsh dozen blows that changed them to bright red. His legs kicked as she colored both ovals equally. His stepmother looked on with obvious approval. Alfred smiled to himself, knowing that soon he would be administering the majority of Jerry's discipline. Finally, Lavinia gave her victim a rapid-fire score of blows, that darkened the discoloration further and caused some swelling. He broke down and shed copious tears. When she put her hand on his bottom, it was hot to the touch. She invited Mrs. Collins to feel the heat, which the delighted woman was happy to do. "What do you say, Jenny?" his aunt wanted to know. "Th... thank you, Auntie Dearest. I'm sure I deserved that." "Now up you get. Let's have Ellen put you back into your maid attire. And no panties, of course. It will do you good to know everyone can see your rosy red bottom." "Yes, Auntie. You're absolutely correct. I need lessons like that." He was becoming quite accomplished at saying what she wanted to hear. At times he was beginning to believe what he said. "Your stepmother and I will be discussing your upcoming nuptials. We can take care of the paperwork and such later. Right now, to be fair to Alfred, we want to move you ahead to your wedding night, as soon as possible." He hated to hear that. At the same time, he was strangely stimulated by her words. The idea of being so deeply under the older man's control was strangely reassuring. Surrender, it seemed to Jerry, would make his life so much simpler and easier. He didn't want to give in, and accept everything that came with that, but he was so terribly tired of trying to resist the inevitable, even if only in his mind. Days later it was time for the informal wedding ceremony. Jerry knew they had something special for him to wear, but hadn't been allowed to see the new outfit. They were going to exchange their vows in a large party room that he had spent three arduous days cleaning. Now he was taken to a small anteroom to be dressed. Ellen and Cookie were waiting. They surprised him by removing his chastity. Did this mean it would stay off? When he saw what he was expected to wear, Jerry almost fainted. Hanging up was a sort of dress in white leather, that would bind him securely and leave portions of his body uncovered, including his bottom. He was too defeated by that point to put up more than a token resistance. "Please," he squeaked. "Don't put me in that. I'll behave. I won't cause any trouble." The women chuckled at his feeble attempt to stand up for himself. Cookie wrapped her arms around Jerry and held him against her generous bust. All he had on was what he had slept in, which was a short filmy negligee. It offered no protection as Ellen took a paddle, which she had had the foresight to bring, and landed a half dozen hard smacks on his bottom, raising it from pale white to rosy red. He squirmed and whimpered but couldn't break free from the cook's firm hold. When she did release him, his tiny penis was erect. Because he no longer had any pubic hair - permanently removed, along with all his other body hair - his male member appeared especially immature. As he stood there sniffling, Ellen said, "Are you going to give us any more trouble, young lady?" "No," he sobbed. "I'm so sorry. I didn't mean to be naughty." He was sounding more and more like the person they were treating him as, a young frivolous girl who needed to be directed all the time. The household staff had gotten him well softened up for his marriage to Alfred. Jerry stood there on legs that threatened to buckle, as the bizarre article of clothing was taken off its hanger, so its high collar could be fastened around his neck, and they got his arms into the long sleeves. In front it appeared like a fitted dress that reached almost to his knees, except that there were openings for his nipples and genitals. In back, it covered him down to the waist, but left his rear and the backs of his smooth hairless legs exposed. That meant his freshly tinted backside was on display. The sleeves ended in narrow mittens, with D-rings on their ends. His arms were pulled behind his back and the rings fastened together with a clip. Straps at his elbows were wrapped around and buckled, so that it was as if he were wearing an arm binder. They sat him down on a backless chair and fitted high boots over his feet. They had three inch stiletto heels, which he had learned to walk in, though they still required him to measure his steps. While he was seated, they fussed with his hair, giving it lots of volume and let it rest softly on his shoulders. Then came the cosmetics, which they applied in a way that gave him a pale, doll-like face, complete with long eyelashes, vividly rouged cheeks, and cupid-bow lips. When they stood him up and walked him - one tiny step at a time - to a long mirror, he was unsettled by what he saw. This was a new look for Jerry, and one that suggested the totally subservient relationship he would have with Alfred, even more submissive than his current one. The strangely erotic looking bride was led from that space to the back of the party room. There were chairs set up in rows on either side of a central aisle. At the front waited Alfred, straight-backed and dignified in a tuxedo that suggested an earlier period. Also waiting for Jerry was the officiator. She was a tall Black woman, with stupendous curves, dressed in a red body-stocking, with a matching pillbox hat. Her hair was shaved almost to her scalp and she wore earrings like big crescent moons. As the male bride moved forward, with Ellen holding his bound arms and walking him, he glanced to the sides. The guests were a curious lot, in fashions that favored leather and rubber. He spotted his stepmother, seated next to a handsome man who had his arm around her shoulders. Further over was, to his surprise, his father. Mr. Collins was wearing a straightjacket. Next to him was a young man in a white smock, apparently an attendant from Fairhaven Fields, who was absently stroking his charge's hair, which had been allowed to grow long. As Jerry took a closer look, he saw his dad had make-up on his face and appeared distressed at the attention being paid to him by his companion. The faux bride could only imagine, after seeing that, what sort of treatment his father was receiving at that facility to which he had been sent. The woman who was waiting to conduct their ceremony eyed Jerry. Her gaze flicked over to Alfred, who she gave a conspiratorial wink. Ellen released Jerry's arms and Alfred was quick to take hold of them. He gave the young man's slim bicep a squeeze. Jerry looked up at him with nervous anticipation. The Black woman began, "We are gathered here today to join this man and this sissy in a very one-sided marriage." A ripple of soft laughter ran through the room. She went on with a short speech about how a man must rule the home and a wife needed to obey him absolutely. Then she proceeded to the vows. "Do you, Alfred, promise to dominate, regulate and discipline this pansy?" After he answered in the affirmative, she asked, "And do you, Jenny, promise to submit, obey and gratefully receive correction from this man?" In his smallest voice, Jerry said, "I do." His stomach felt as if he had swallowed a dozen butterflies. To Alfred, the woman said, "You may put the ring on her." From his pocket he took a ring that was plainly too wide for Jerry's finger. When he opened it, his spouse saw that it was hinged and the ends were points. Jerry tugged at his arm bondage as Alfred fitted the ring into his nose and closed it, so the points dug painfully into his septum. Alfred said, "With a ring at the end of her nose, her nose. With a ring at the end of her nose." The overseeing woman said, "You may kiss your servile bride." Bringing his lips to Jerry's, and his hand to his exposed male parts, Alfred simultaneously kissed him and gave his small penis a few squeezes. When he stepped away and turned him toward the watchers, everyone saw that the bride had sprouted an embarrassing erection. There was warm applause as they started to walk down the aisle, Jerry mortified at how his unwanted stiffness bobbed up and down. They were joined at the back of the room by Lavinia, Ellen and Cookie, as a receiving line formed. Alfred eased Jerry down onto his knees, a position the helpless newlywed knew he would be assuming frequently. As everyone passed by, Jerry had to look up at them. His dress's tall stiff collar made him keep his chin raised. It was so shameful, to be seen by everyone, the way he looked. After that, the happy couple - well, the happy groom and his frightened bride - moved to the reception, in the dining hall. There was plenty of food and drink. Lavinia and Mrs. Collins sat with the wedding party. Mr. Collins was at the far end of the table, in Jerry's direct line of sight, so he couldn't avoid seeing him, and all the unwelcome attention he was getting from his companion. Guests came up to the head of the main table to leave gifts with the groom. Mostly they were envelopes, but also some boxes. Alfred opened the latter, to reveal sex toys, punishment instruments, and several chastity devices, in various sizes. He made a joke about the smallest cock-lock being most appropriate for Jerry's undersize penis. The intended wearer wanted to point out that, even for him, it was too tiny. Of course, by then he knew better than to speak up. Several hours later the gathering broke up and the guests departed. Now came the time Jerry had dreaded most. The consummation. They went to a guest bedroom that had been fancied up as their bridal suite. Alfred scooped Jerry up in his arms and carried him across the threshold, taking the opportunity to grope his bare bottom. There was champagne in an ice bucket. Cookie reminded Alfred that she would be happy to prepare anything he wanted to snack on. The plump mistress of the kitchen joked, "You may need some protein to keep up your strength." "But not Jenny," he shot back. "She'll be getting plenty of protein by direct injection." He told everyone he would see them in the morning. As Lavinia, last to depart, closed the door, Jerry's final hope vanished. Alfred helped him onto the bed, arms still bound, and got him on his knees, with several pillows under his chest, to raise his mouth to a convenient height. He had Jerry turned sideways, so his head protruded slightly over the edge of the mattress. Alfred undressed slowly, savoring the anxiety on his bride's face. When he freed his impressive cock, Jerry whimpered. The naked man stepped close enough for Jerry to reach the naked organ with his lips and tongue. In no time he had it standing up and leaking clear drops. "So nice of you to get me hard for what comes next," Alfred told him. "And to make yourself so available. I'm sure you'll be ready, willing and able to do the same, any time I want it. After all, it's an essential part of your wifely duties. Don't you agree?" "Yes, Sir," Jerry whispered. "Do show some enthusiasm. Wouldn't want to spoil the mood on our wedding night. Now, are you enjoying yourself?" "Yes," Jerry lied. "Very much." He wrapped his lips around the head of the wet cock and gave a few hard sucks. As much as he hated to say it, he went on, "And I can't wait for what comes next." "I'm sure you can't, you little slut. The way you've been mouthing my tool all these weeks, I can tell you're eager to get to the main act. Now let me turn you, and move those pillows to the head of the bed, so you can be comfortable while I make us truly husband and wife." Jerry quivered all over. He told himself it was from stress, but when Alfred ran his hands all over him, ending up with his fingers between the arm-bound sacrifice's bottom cheeks, he had to admit that the older man was always proficient enough to include a dimension of excitement when he used his prey, even now. Jerry didn't want to respond positively, but his dick again, as it had after the kiss that sealed the marriage, rose against his wishes. From the nightside table, Alfred took a tube of lubricant. "Do you want me to use plenty of lube?" he asked mischievously. "Yes. Please." Jerry took a breath. "I want this to be as good as possible for you." Moments later, the tube went back where it had come from. Alfred's slicked fingers parted Jerry's nether cheeks. There was pressure against the helpless target's pucker. Jerry mewled. Alfred leaned forward, letting his weight push the knob of his cock through that too-tight opening. Jerry groaned as the head entered him. Alfred paused for a few seconds, before slowly driving the rest of his considerable length inside. Jerry felt the man's large balls press against his own much smaller ones. As the anal invader began a slow in and out movement, Jerry sighed in spite of himself. It hurt, but his erection was not softening. His testicles throbbed. He bleated sadly, but that was followed by panting, as he was deflowered with accelerating energy. "This is good," Alfred said, more in control of his breathing than the sissy. "Very good. You know I'm going to want more, on a regular basis." "Noooo," Jerry whined. "Yessss," Alfred assured him. The man on top worked his hips faster. He made a growling sound, deep in his throat. Then he tensed and was suddenly spurting his load into Jerry. As much as the bride tried to keep from doing it, he ejaculated at the same time. Alfred gradually slowed down, enjoyed the sensations of staying inside a bit longer, and then pulled out. The recipient of his attention was crying softly. Alfred tipped him onto his side and saw what he suspected he would, the telltale splotch of white cream. "Well, well," said the husband. "Looks like somebody besides me enjoyed that cherry-popping. But I can't have you making messes on the sheets all the time. Even though you're the one who will be doing the laundry. Wriggle back until you can get your mouth down there and lick up that sissy sauce." He watched gleefully as Jerry performed the demeaning task, gagging and choking. Then Alfred took the smallest of the chastity devices, wiped his bride's penis clean, slipped a sturdy ring over his genitals, and fitted a pink plastic cover over Jerry's flaccid cock. When he locked the two parts together, there was no way for the wearer to achieve another erection. Alfred gave him some of his expert stroking, especially on his nipples, and made Jerry see how effective the device was. Jerry had been out of chastity for such a short time. "It could be a long time before you get to empty your baby balls again, Jenny. Be extra nice to me, if you want to have a better chance of being allowed to do that." "Yes, Sir," he cooed, his tone calculated to plead his new spouse. "Now, let me get cleaned up and have a glass of champagne to celebrate. In a short while I'll be ready for some more fun. I'm thinking I'd like a tongue bath from your talented mouth. How does that sound?" Jerry had to swallow the words he wanted to say. Instead of those, he bubbled, "That would be wonderful, Alfred. I like it when you think of things like that for me to do." He was rewarded with a smile. It was obvious that acting like the sexually permissive, eagerly enthusiastic wife would be good for him. He didn't want to receive another spanking or more bondage on his wedding night. Alfred released Jerry's arms. The bride moved them around to work out the soreness from being so heartlessly strapped. After Alfred had enjoyed his glass of champagne, he poured one for his spouse, but insisted on feeding it to him, a sip at a time. Jerry was coming to feel even more dependent on his husband. He believed the rest of the night would be difficult, starting with that tongue bath. He was right. The next morning, Jerry was given another wedding gift, this one from his stepmother. It was the maid outfit she had rush-ordered, and had express delivered. The abbreviated outfit was completely in pink. There was even a matching feather duster. He had to model it for her and her lover. The man found the sight hilariously funny. Then Mrs. Collins departed with her bedmate. Jerry had to sear his shameful new outfit while he cleaned up after his own reception, which was an all- day job. Then it was another night of connubial bliss, though more for Alfred than for him. But Jerry's libido was aroused again. The difference this time was that he had no way to release his mounting need. In the nights that followed, there was more of the same, until he was distractingly horny, yet unable to gain relief. Alfred rerouted all that sexual energy into reshaping Jerry as his sexual plaything, anxious to please, willingly doing more and more to satisfy his husband. The chilling probability was that he would be reduced to a simpering sex toy who was incapable of regaining his old personality. Worse, he had to experience it happening in stages, day by day, while being impotent to do anything about it. His balls hurt so much from being made to wait and wait. There were more maid outfits, in a variety of colors. He liked the canary yellow and mint green ones less than the lavender and chartreuse ones. His life was coming to revolve around minor situations like that, which were the only times he was able to have an opinion about anything. Spankings were common and bondage was applied with imagination. Sometimes he had to do his housework while strapped into a deep crouch. At other times he was encased in a rubber sack that forced him to crawl around like an inchworm. There was a cut-out for his bottom, which made it convenient to administer corporeal punishments. Eventually, his entire life was a never-ending series of painful and pleasurable experiences, deftly handled by Alfred, with cheerful help from Aunt Lavinia, Ellen and Cookie. Sissy Jenny, as he was sometimes addressed, had to accept it all. There were perverse scenes he was made to play, and all of them he came to crave reenacting. The old Jerry was gone, replaced by a pretty pansy, who was devoted to her firm-handed husband. The made- over maid knew that his future held much more of the same. He accepted it all. What else could he do? (If someone else had written this, I would have told them to split it into two parts. What can I say? It kind of got away from me.)

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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

2 years ago
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AUNTIES SURPRISE

My first sexual experience happened many years ago when I went to spend two weeks with my cousin and my Auntie Mairi. To build the scene Aunt Mairi lives alone in a small 2 bed cottage beside a glorious beach in a remote area of Scotland. My cousin Catherine is my other aunties daughter and a lively 13 year old girl just starting to develop into a beautiful young woman and a year older than me. Both mine and Catherines parents had travelled abroad for a holiday and had decided Aunt Mairi was...

4 years ago
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aunties pee problem

Look after your auntie my mum had requested as I left the house. I picked her up and took her on the shopping trip that she had arranged with my mum for me to do. As she came out of the house I noticed that she had got noticeably bigger in the month since I’d last seen her. She was 8 months pregnant and as she walked down the drive she walked as if she’d shit herself. Her big fat round belly and huge pendulous tits made her dress look skin tight. Her legs had put on weight and I could hear...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

4 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

2 years ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

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