The Bettor Maid free porn video

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The Bettor Maid Belladonna [Based on an idea by Tondelaya] Trystan Pretto stared at the large brown box containing the only clothing that he was going to be permitted to wear that month. He peered up at his wife, Natalie, with a smile as he wondered what ridiculous costume she was going to make him wear given their ever escalating series of bets. They started making bets with each other a few months after they won an interstate lottery. The sum of money they had received ensured that neither would ever have to work again. Being a young couple, only in their late twenties, neither was particularly attached to their jobs. Consequently, they had no problem quitting their jobs shortly after the check cleared. With no employment or children to tie them down, Trystan and Natalie began to travel the world. They spent several months abroad before they returned home after growing weary of their constant travels. Despite their enjoyment of each other's company, the two began to grow bored as they faced many hours filled with nothing to do. Shortly after the constant boredom set-in, Trystan and Natalie started to make bets with one another to help make their lives more interesting. They began by making bets based on random things such as sports, the timing of deliveries to the home and what neighbor's car would arrive home first. The terms of the bets started out mild, but they progressed rapidly to where they were at that moment. For the four prior months, they only made one bet with each other each month. The loser was, now, required to comply with the terms of the bet for a full month. Trystan won the first such bet and made Natalie dress in nothing but the fetish costumes he bought for her for a full month. Natalie was further required to stay in character the entire time she was dressed in the various outfits he left out for her each morning. While Natalie was uncomfortable in some of the outfits, she had to admit that role- playing with Trystan as a nurse, librarian, school girl, cop, prisoner and other roles helped to make breakup the malaise that had overtaken their lives. When Natalie won the second month's bet, Trystan found himself following her around Europe as her man servant and forced to carry her purse everywhere they went. Even as he saw men walking by with their man purses or 'murses' as Trystan liked to derisively call them, Trystan knew that everyone that bothered to notice him was aware that he was carrying what was unambiguously purse as Natalie's cycled through three leather bags in different colors during the trip. Trystan was certain that he looked even more ridiculous given his 6'2" height and slight build. Trystan felt that his height drew further attention to him as he walked around the city streets beside Natalie with her bag clutched between his hands in the manliest way he could think of carrying it. On the last night of the month, they made a bet for the following month. Natalie exclaimed as she won it and told Trystan that she could not wait to get back home. Trystan was relieved to be back in his own home, even if it was as Natalie's slave. Natalie made him spend his evenings between her thighs after he spent the day helping her lose the weight that she had gained during their month long vacation. Trystan was happy to do it even as the crash diet she put them both on tired him. Trystan was a bit concerned, however, to drop the 20 pounds, which was five pounds more than he gained abroad. Given that his frame was already lean, Trystan did not feel that he had many pounds to spare. Natalie, meanwhile, dropped back to her former weight as she last weight a slower clip than he did. As his month as her slave neared its end, they made another bet. This time, Trystan prevailed. Natalie smiled at him as she waited to hear what she would have to do for the following month. She was not all that surprised when Trystan advised her that she would be his maid for a month. Once the uniforms arrived, Natalie was a bit surprised, however, to see that they were formal maid's uniforms and not the fetish ones that she was expecting. She was relieved to see that. Trystan had thought about getting her fetish uniforms for the months, but he figured that she might react negatively to having dress in the same type of fetish uniform for the whole month as opposed to rotating through different roles as she had the first month. Trystan took full advantage of having a maid, however, as he ordered Natalie about the home and even had her go to local supermarket and stores to shop for him in uniform. Natalie was a bit excited at how dismissively people treated her as she walked amongst them in her simple, unadorned uniform. She realized that everyone believed that she was of lower class and a powerless woman, and they treated her accordingly. As the month reached its end, they made another bet. Natalie did not exclaim when she realized she won the bet. She merely looked over at Trystan for a moment as she pulled at the hem of her grey, pinstriped maid's dress. Trystan looked at her with growing unease as he waited for her to finally tell him what she expected out of him for the month. She remained silent as she continued to gaze at him, trying to make him sweat it out further. "All right, what is it?" Trystan asked, growing weary of waiting. "Well, Trystan, since I served you for the month, I figure that you should be my servant for the month." "Oh, your slave again?" Trystan asked with a laugh. "No. My servant. There's a difference." "So what am I going to be doing the male version of this stuff, gardening and that all shit we pay the landscaper for?" Trystan asked. "Oh, no, that's much too rough and tumble for a boy with your hands. You're not strong enough for that type of work with your physique, plus putting those slender legs in pants would just be a sin," Natalie replied with a smirk and a wink. "What's that supposed to mean?" "I was your domestic, now you're mine," Natalie answered. "You already said, but what do you mean? What am I going to be, your butler?" "You'll see," was the extent of Natalie's response as she left him to place an order for rush delivery. ----------------------------------------------------------------------- As Trystan began to be ordered around by Natalie the next morning, Trystan began to realize that she expected him to do the same work that she had done for him around the home. That fact made Trystan increasingly worried about what she had purchased for him to wear for the remainder of the month. The box arrived the second day of the month, and Trystan signed for it. Natalie came to watch Trystan open the box. "What are you waiting for?" Natalie asked with a smile as Trystan stared at the brown box in silence. Trystan sighed as he began to pull off the tape that was sealing the box closed. The sight of the clothing in the box caught Trystan's eyes while he pulled the flaps of the box open. "What the hell?" Trystan exclaimed. "Do you like it?" Trystan shook his head before Natalie added, "Well, I was your maid, so now you're my lady's maid. I think that's fair." "It's not fair. You're a girl," Trystan retorted as he picked the first outfit up. Natalie grinned as she watched Trystan's mouth open and his eyes grow wider as he noticed that the frilly dress was unlike the one that he purchased for her to clean in. The clear fetish nature of the dress caused Trystan to turn towards his wife and shout, "This is too far!" "I don't see it that way," Natalie responded before she sipped on the wine in her hand. "You at least got to wear a normal maid's dress, this is..." "Oh, wait to you see the shoes that go with it," Natalie interjected. Trystan pulled out the six other dresses before he reached the bras, panties and stockings that Natalie purchased for him, which rested upon the four shoe boxes at the bottom of the shipping container. Trystan carefully removed his feminine undergarments from the box before he took hold of the first box and looked over the large fetish heels inside the box. He turned his head and glared at his beaming wife. "This is totally unfair," Trystan said. "Why's that?" Natalie asked as she smirked at her husband's teen like objections. "You had to wear..." "Yes, but I had to wear it everywhere. You're only a maid inside this house. Unless you really want to push this, then I could see making you do the shopping in that pretty prink dress," Natalie said as she pointed to one of the fetish uniforms. Trystan swallowed hard and stared at the dress before he turned towards his wife. From the look on her face, Trystan could tell that she was completely serious about making him spend the rest in the month inside the home catering to her every need in fetish heels. Natalie noticed Trystan's continued unease and said, "Don't be so prudish. You've got to be more adventurous, dear." "Adventurous?" "Yes. Don't take this as an affront to your manhood. Take it as a challenge. You liked my role-playing for that month. This is just one role for you. You're going to be my slutty lady's maid, and I expect you to do a good job in every job your given." "These shoes are going to kill me." "I'm afraid you're right. Those are going to hurt like hell when you're on them. Fortunately, for you, you'll be spending a lot of the month on your knees." Trystan felt a surge of arousal as he remembered serving Natalie for an entire month as her slave and knew that he would be doing a modified version of it. Still, the uniforms were a turn off for him, but, given that neither one of them had backed down from a bet yet, Trystan decided that he would have to solider through the month in heels and petticoats. Natalie could sense Trystan's acceptance of the situation. As Trystan began to look at the clothing that he had taken out of the box, Natalie said, "Trystan, just put those clothes back into the box and follow me." Trystan complied with her order and carried the box behind her as she led him into their bedroom. Natalie then directed Trystan to hang up each dress in his closet. As he obeyed Natalie's orders, Trystan looked over the seven maid's uniforms that he hung up in the closet. They were all different, even as they were only in four colors, white, pink, black and baby blue. While six of the dresses were satin or sateen, one of the black dresses was PVC. Once Trystan finished hanging up his dresses, Natalie made him clear out his underwear drawer of his dresser and replace his undershirts, boxers and socks with the bras, stockings and garters she had purchased for him. Trystan stared at the undergarments in his dresser drawer with a perplexed look before he asked his wife, "Are you making me go commando all month?" Natalie laughed and said, "Oh, no, darling. I've got a surprise for you." "What is it?" Trystan asked as he nervously crossed his arms while he began to dread whatever else Natalie had planned for him. "I picked them up yesterday, but they're going to help you fit into those pretty dresses so much better. After all, I can't have a manly maid, can I?" "I don't think you have the option not to," Trystan countered. "We'll see about that," Natalie retorted as she opened her closet door and picked up a bag. She took out seven pairs of waist cincher brief panties with a high leg cut and garters and placed them in Trystan's hands. Trystan felt aroused by the nylon spandex fabric in his hands as he looked over the hook eye front closure of the cincher. Four pairs of the waist cincher brief panties were in black, while Trystan had one pair each in ivory, crimson and nude. Trystan gently placed them into his underwear drawer before Natalie said, "And that's not all." "There's more," Trystan asked before groaning a little as he felt conflicted by his arousal from the feeling of the clothing, even as he was certain that he should be disgusted by the thought of wearing it. Natalie nodded as she pulled out two clear, jiggling molds. Trystan stared at them and asked, "What the hell is that?" "These are called butt pads. They're supposed to enhance your rear." "Oh, goodie," Trystan replied in a wry tone. Natalie smirked at his response before she said, "And, of course, you're going to need something to fill the cups of those lacey bras I bought." "Oh, yes, of course," Trystan replied as he failed to even attempt to hide his sarcasm. Natalie removed the two breast forms from the bag and placed them down besides the adhesive she had purchased for Trystan as well. Trystan stared at the four forms and the glue with an uneasy feeling in his stomach. Natalie headed towards the door, expecting Trystan to follow. As he continued to gaze vacantly at the forms, she snapped, "Hey, maid. I'm not paying you to stand around here. Let's go!" "You're not paying me at all," Trystan countered. "True, but I won you fair and square, so follow me." Trystan nodded as he followed his wife into the bathroom. As they entered it, Trystan smelt the familiar scent of Natalie's bath oil. Trystan saw that the shower curtain was drawn back. He looked down and saw the filled bathtub. Natalie looked at Trystan and said, "Strip." Trystan complied with her one word order as he disrobed. Trystan then waited for Natalie to tell him to get into the tub. Trystan stepped into the warm water and lowered his body down into it. Trystan felt strange to be surrounded by the flowerily smelling bathwater. Trystan had not taken a bath in decades and the source of the smell was something he had never been so close to. As Trystan acclimated himself to the waters, Natalie readied her pink razor. She told Trystan to place one leg out of the water. Trystan did so and felt a cold chill upon it before Natalie put the shaving foam onto his leg and began to draw the razor down it. The sensation felt odd to Trystan, but no odder than the bare patch of leg looked before Natalie ran the blades of the safety razor across his skin for a second time. Natalie removed every strand of hair from Trystan's leg before she made him remove the other leg from the water. While Natalie removed the hair from his second leg, Trystan tried to think about anything besides the foam and leg hairs that were floating around his body that were giving him further reminders of his feminization. With his legs finished, Natalie told Trystan to sit up. He did so, Natalie bent over him to apply the foam to his chest. Trystan stared down Natalie's halter top as she did so. Her large breasts were at his eye level as she began to draw the razor down his chest. As he did not have much chest hair, Natalie did not have to linger long in front of him to Trystan's disappointment. She then made him lift his armpits as she turned her attention to removing his underarm hair. Trystan complied with her orders as more hair surrounded his body as she plunged the razor into the waters around him after each stroke to help clear off the matted hair. Once she finished with Trystan's armpits, Natalie pulled the stopper out of the bathtub drain. Trystan watched as the water was sucked the drain, carrying with it the various strands of masculine hair that had been attached to his body when he stepped into the tub. Natalie handed Trystan a towel as she told him to get out of the tub. Trystan took the towel from her and dried himself off as Natalie fumbled through her makeup bag. Natalie turned towards the door and stepped out of it as Trystan wrapped the towel around his waist. Trystan sighed as he looked down at his hairless body. He peered over to his wife and noticed that she was beckoning him towards her. "Now what? Are we going to the salon so you can make my hair all pretty too?" Natalie stared at her husband. She was upset by his slightly peeved tone while she replied, "I wasn't planning on that. I was planning to just let you wear a wig since you were going to be doing your shopping as a guy. If you want though, I'll certainly make arrangements..." "No, that's not necessary," Trystan interjected. "It would really be no trouble. I'm sure the girls at the salon would love to give you some extensions for your hair and nails..." "No. Really, the wig is just fine," Trystan interjected once more. Natalie stared at him for a second before she nodded as she replied, "Okay. I'll make this one accommodation for you." Trystan nodded as Natalie agreed to do what she had been planning to do all along. Natalie then motioned for Trystan to follow her back into their bedroom. Once they entered, Natalie removed Trystan's towel and told him to place on a black waist cincher with a panty brief. Trystan nodded before he opened his dresser drawer and removed the garment and placed his legs through it before he began to draw it up his legs. Before he reached his crotch, Natalie shouted, "Freeze. I'll take it from here." Interested to see what Natalie was planning to do, Trystan stopped moving. Natalie walked over to him and hurried behind him with the butt pads in her hands. She slightly moved the waist cincher up over them to help hold them in place. Trystan then felt her warm, smooth arms drag down across his sides before she clutched his enlarged member. Trystan blushed and felt more aroused than he had all day before Natalie yanked his member between his legs and pulled the panty brief into place over his crotch. Trystan blushed while he gazed down to marvel at how smooth the front of his body looked with his member tucked away while Natalie straightened his butt forms in his panty brief. While it was what Natalie intended, Trystan was embarrassed to be seen by his wife with a smooth, feminine front as she walked in front of his body to hook the cincher into place. Trystan felt a sudden pulling on his sides as the feminine traits of his slightly girlish figure were embellished the cincher. Natalie took a step back from him and smiled. She covered her smile with her hands before she told Trystan, "Get a pair of black stockings." As Trystan sensed the compressed feeling of his abdomen while he moved towards his dresser, Natalie's eyes gazed at how feminine the middle section of his body looked with his waist cinched, tucked away member and padded rear. Trystan opened a package of black, sheer stockings before he was told to sit upon the bed. Natalie rolled the first stocking down and placed Trystan's toes to the seam before she began to bring the stockings up his legs. Trystan felt aroused as the silky soft feeling ascended his legs. Trystan smiled at the feeling as Natalie brought them up his thighs before she hooked the stocking to his garters. Natalie then repeated what she did with the other stocking and stood him up. After checking that the stockings were firmly attached to the garters of Trystan's waist cincher/panties, Natalie smiled as she moved him towards her dressing mirror. She pulled at his wrist as Trystan sauntered behind her in no rush to see what she was so eager to show him. Natalie positioned Trystan so that he could see his side profile in the mirror. She pointed to Trystan's mid section and said, "Now, that's lady like." Trystan cringed as he saw his smooth front on one side and his enlarged, feminine rear on the other before Natalie turned him to see his almost hourglass figure. Natalie smiled as she said, "And that's just for starters. Just wait until you see the rest of it. You'll be my pretty maid yet." Trystan gave Natalie a vacant look before he gave his reflection an uneasy glance. Natalie smiled as she walked over to the dresser and took hold of his breast forms and told him to come over to her. Trystan walked over to his wife and felt the coolness of the adhesive as it was applied to his hairless chest before the breast forms were attached. While Trystan held his breast forms in place while the glue dried, Natalie took hold of a black bra. She placed it around Trystan's waist and moved his hands away from his chest as she drew it over his fake breasts. She hooked the bra behind his back and said with a wink, "Good luck taking that off." Trystan gave her a suspicious look as she began to straighten out his bra over his false bust. After she was satisfied that his breasts were sufficiently straight, she began to adjust his bra straps. Once she finished adjusting the bra straps over Trystan's shoulders, Natalie pulled him back towards his closet. She then removed the black satin maid's dress from the hanger and handed it to Trystan. After gawking at it for a moment as he realized that his wife was really expecting him to wear it, Trystan stepped into the dress and brought it up his body. Natalie walked behind him and pulled up the rear zipper before she took out one of the shoe boxes and placed a pair of black shoes with two inch block heels in front of Trystan. Trystan realized that Natalie expected him to put them on, so his slipped his feet into them and secured the straps. Natalie then turned and went back into her closet and returned with a brunette wig, with long, curly strands of a hair and a wig cap. She had Trystan take a seat on the bed again. She then secured the wig cap to his head before she fastened the wig to it with bobby pins. "One last touch," Natalie then said with a smile as she minced away from him in a hurry with her hand out to the side. Trystan fought the fact that he was turned on by the way she was walking as the erection tucked between his legs was uncomfortable. Natalie walked back over to him with the maids cap in her hand and had him bow his head towards her so that she could secure it. With his clothing and hair done, Natalie turned her attention to doing his makeup. Trystan was a bit concerned about what she was doing with the lip-gloss, eyeliner and mascara, but he knew that he did not have any say in his appearance at that moment. Given the fact that he was sitting before her in a maid's dress, stockings and heels, he did not see the point in contesting anything she was going to do with the makeup either. After spending a few minutes applying his makeup, Natalie smiled as she said, "All finished." Natalie then helped Trystan to his feet. Trystan stared down at his wife. The perch of his heels made him seem even larger than he was. Trystan noticed that he was towering over his 5'6" wife, even more so than he was used to as he was so much larger than Natalie to begin with. Natalie guided Trystan back towards the mirror as she told him to take short and straight steps. Trystan followed her directions as he did not want to twist his ankle. As they approached the mirror, Trystan gazed at his reflection. Natalie put her arm around his waist and said, "See, I don't have a manly looking maid." Trystan unconsciously found himself nodding along with her assessment even though a part of him cried out to counter her words. While Trystan did not think that he was as pretty as his wife indicated that he was, Trystan felt that if it were not for his height, he would be unambiguously feminine. Together with his slender physique, Trystan's height, however, was also giving him a statuesque appearance. Trystan found himself marveling at how much more feminine his thin legs looked in hosiery. As Natalie hugged him, Trystan thought, 'I really need to hit the weights more.' "Natalie...," Trystan began to ask his wife who promptly cut him off. "Tsk, tsk, maid. A good maid never calls her mistress by her first name," Natalie replied as she released him from her embrace. "What do you want me to call you then?" Trystan asked. "How about Miss Driver?" "Your maiden name?" Trystan asked with evident surprise in his tone. "Well, I think a nice little separation from our two places in life is in order. I can't be sharing the same last name as my maid after all." Trystan looked at her uneasily. Natalie could sense his unease about the potential ramifications on their relationship. She relented as she added, "You know what? Maybe that's too informal. I think you should call me Mademoiselle instead." "Seriously?" Trystan asked. "Yes, I think the French version is just so much prettier to hear." Trystan nodded even as he felt that calling her Mademoiselle instead of Madame was somehow more emasculating. Natalie smiled at her husband as she watched him nod and pull at the hem of his black, satin, maid's dress. She stared up at his face as she walked beside him and said, "Now, there's just the matter of what I will call you?" "Excuse me?" Trystan asked for clarification. "Well, Trystan just doesn't fit for this lovely lady's maid standing before me. No. It's just not right for a girl of your status." "It can be a girls name too," Trystan countered even as he was oddly excited by Natalie's reference to his new stature. "Yes, but that's like the type of name of hipster gives her daughter, not a person who gives birth to a domestic." "So what are you thinking?" Natalie smiled as she replied, "Minnie." "Oh come on," Trystan retorted as her heard the name that struck him as an incredibly emasculating. "Oh, don't be that way. We both know it's not a descriptive name in anyway," Natalie responded as she stared up at her towering husband and brushed her hand across his flattened crotch. Trystan felt turned on by her touch as she touched the place where his manhood should have been. She pulled at his dress as she stared up at him with a smile. Trystan bent down and placed a kiss on her lips. As their lips parted, Natalie playfully pushed Trystan away and said, "Enough that. I think I've consorted with the help long enough. It's time to put you back to work." "Okay, Natalie." "What was that maid?" Natalie replied with mock indignation. "Sorry, Mademoiselle." "That's better. Now, go prepare me a salad for lunch." "Yes, Mademoiselle," Trystan replied, as he struggled to keep his mindset in line with the domestic he was supposed to be. Trystan walked out of their bedroom and gingerly headed down the staircase, clasping the banister as he did so. He walked into the kitchen and began the time consuming task of chopping up the vegetables for his wife's Greek salad before he cut up the feta cheese Natalie liked. After finishing tossing the salad and adding the dressings that his wife liked, Trystan presented the bowl of salad to her. Natalie shook her head at him and said, "You served the meal before you set the table, silly girl." "Sorry, Mademoiselle," Trystan replied as he hurried to get his wife a napkin and a salad fork. "I'll let it slide this time," Natalie said as she smiled as she watched her husband's hasty, clumsy steps in his heels as the sound of his heels clicking on the marble floor reverberated through the room. Trystan hurried back to the table and placed the napkin and fork next to Natalie's salad bowl. Natalie took a bite before she said, "Minnie, be a dear and fetch me a drink." Trystan realized that his wife had been unspecific to force him to ask, "What would you like, Mademoiselle?" "Bring me a glass of Pinot Grigio." "You're going to start drinking this early?" Trystan asked, surprised. "Maid's do not question their mistresses, Minnie. Is that understood?" Natalie replied with a stern look on her face. "Yes, Mademoiselle," Trystan replied. "Good, girl. Now, I will be having a glass of Pinot Grigio with my lunch everyday from now on. It'll be my new thing. Understood?" Trystan nodded before Natalie asked again, "Understood." Trystan could tell that his wife was demanding an oral answer to hear him speak the word that indicated that she was in a higher station of life. Trystan nodded as he replied, "Yes, Mademoiselle." After answering his wife, Trystan went and selected a bottle of wine for his wife. He popped the cork and poured it into a glass before he added two ice cubes as he knew that his wife preferred her wine chilled. Trystan carried the glass over towards his wife and placed it on the table before her. She smiled as she took it and took a sip. She then ordered Trystan to stand to the side as she ate her meal. Trystan complied with her orders and stood to the side of the table with his hands clasped before him as he waited for her next order. Upon her request, Trystan refreshened her drink with some trepidation. While Natalie was a social drinker, Trystan knew that alcohol freed his wife of her inhibitions more than it did most people. Trystan wondered what she would make him do as the wine began to affect her. Part of Trystan was eager to see what she would do, but another part of him feared how far she would take certain things. After Natalie finished eating, she took her drink into the great room to watch television. Trystan took to cleaning up his wife's lunch before he ate what was left of her salad as he did not want to go through the trouble of making one of the three other lunches that she approved for him. Trystan finished his lunch and cleaned the bowl before he walked towards Natalie as his feet began to ache from the unnatural positioning and weight distribution. Natalie turned towards her husband and smirked as he asked if she needed anything. Natalie replied with a list of chores for him to attend to before dinner. Trystan made a mental note of each of them before she dismissed him. Trystan took to each of the chores that Natalie had ordered him to do in turn. Trystan started by pressing a dress for Natalie. After searching through her closet to retrieve it, Trystan began to press the dress. Trystan did not know why she wanted him to iron the dress. It was his favorite dresses. He loved seeing her in it, and she was well aware of that fact. Once he finished pressing the dress, Trystan hung it up for her before he turned his attention to cleaning the master bathroom. Trystan wiped down the sink basin before he scrubbed the tub and toilet. Trystan then hand scrubbed the floor of the bathroom. While Trystan's arms quickly grew tired of the repetitive motion of scrubbing the floors with the scrub brush, he actually felt relieved to get off his heeled feet. When Trystan finished cleaning the bathroom, he clasped the vanity and the molding around the bathroom door to help get back onto his feet. The familiar stinging in his feet greeted him as he stood erect once more. Trystan sighed at the pain before he headed down the stairs to begin making the time consuming dinner his wife requested. Trystan saut?ed the meat before he placed it in the oven and returned to his other household duties. As Trystan began to clean the downstairs bathroom, Natalie noticed that he was doing so with a scowl on his face. Natalie berated Trystan and said, "Minnie, I expect you to have a cheery demeanor when you go about your labors. I will not have a dour looking maid bringing me down. Am I understood, missy?" "Yes, Mademoiselle," Trystan replied with a forced smile that prompted a genuine grin to come to Natalie's face. Trystan could tell how much his wife was enjoying her control over him. Her enjoyment seemed to be even greater than the first two times she won and began to direct his every movement. As Natalie continued to watch him work, he began to hum Walking on Sunshine to his wife's sincere amusement. "Now, that's what I'm talking about, girl," Natalie said with a laugh before she turned and walked away from him. Trystan stopped humming as she walked away, but he found himself unable to get the annoyingly catchy song out of his head as he continued to clean. Trystan laughed to himself as he thought about how ridiculous it was for him to be humming the tune given that he felt as if he was walking on thumbtacks with each step. As Trystan finished in the bathroom, he returned to the kitchen to check on dinner before he walked back up the staircase to make the bed in the master bedroom. Trystan straightened the covers and sheet over the king size mattress. When he finished, Trystan began to tidy up the room by picking up the various items on the floor and carrying them to the hamper. Once Trystan finished cleaning up the master bedroom, he carried the hamper to the laundry room and emptied the contents into three baskets, one for dark wash, one for white wash and the other for intimates reserved for hand washing. Trystan then placed the hamper back into the hallway and returned to the kitchen. He checked the meat again before he began to prepare the side dishes his wife requested. As he waited for the food to cook, Trystan scurried around the kitchen in painful, but increasingly less awkward steps. The longer he spent in heels, the more natural walking in them became for Trystan, although he still found himself struggling to avoid the occasional stumble. The pain in his feet was not dissipating, however. It was also not increasing to Trystan's general relief. While Trystan felt extremely pained by the shoes, he was able to carry on through it much like when he played through injuries during his high school and collegiate football career as a wide receiver. Trystan set the table before he finished preparing the dinner. He placed the various dishes upon the table before he went over to his wife and said, "Mademoiselle, dinner is served." "Oh, thank you, Minnie," Natalie slurred as she got up. She paused before Trystan and ran her ran hand down the sides of his dress. Trystan stared at her with a confused smile before she turned away from him, and he carried her fourth glass of wine over to the table. 'Someone's going to have hangover tomorrow,' Trystan thought to himself as he shook his head as he followed behind her. Natalie veered away from the table and told Trystan that she would be back down in a minute. Trystan wondered what she was doing until his wife came back down the staircase in the dress he had pressed for her. Natalie smiled at him and explained, "The lady of the house must always look prettier than her maid at dinner." Trystan nodded at her, unable to deny how good his wife looked at that moment. He wished that he would be joining for dinner, but he knew that that was an impossibility. Natalie took her seat before Trystan went to get her another glass of wine. As he turned away from, Natalie said with a grin, "Bring the bottle and bring it on a silver platter." Trystan nodded as he went and took out the silver serving tray they had and placed the bottle of wine upon it before he slowly carried it towards the table. Natalie laughed at her husband's slow steps as he tried to keep the bottle upright as he was not used to balancing a bottle on a tray. Trystan placed the tray upon the table as his wife continued to eat before he leaned over her and poured more wine into her glass. After Trystan placed the bottle back down, he stood to the side and waited for his wife's further instruction. She made him serve her various times, careful to never ask for two things at once so that he would go back into his waiting position for a second before she would ask for something else. Trystan could tell that she was trying to fluster him. Trystan complied with her orders and sneaked occasional leers at her body beneath the dress he so loved to see her wear. Despite her efforts to agitate him, Trystan was actually turned on by her behavior for reasons that confused him. While he had no doubts about his physical attraction to his wife, his responses to her condescending tone and orders troubled him. Trystan wondered why he was so turned on by feeling as if his much smaller wife had all the power in their relationship, but he knew that he did. Once his wife finished eating dinner, Trystan cleaned the table and ate the leftovers while he cleaned up the pots, pans and dishes. After Trystan placed them away, he tidy upped the kitchen and joined his wife in the great room. As he walked into the room, his wife called out for him to get her the magazine that was resting on the table in front of her. Trystan walked towards it and bent from the knees to pick it up, but Natalie stopped him by saying, "No. Bend from your waist to pick it up." "Isn't that a little mannish in a skirt?" Trystan asked. "I'll be the judge of that," Natalie replied with a smile. Trystan bent down and picked up the magazine. Before he could stand up straight, he felt the pinch of his wife's fingers upon his rear. Trystan's head jerked towards his randy wife who smiled and said, "The lady of the home always gets what she wants." Trystan felt turned on by his wife's words and touch as she motioned for him to join her on the couch. Trystan sat beside her, instinctively placing his arm around her as he always did as a man. Natalie smiled as his actions as she pulled at his stocking covered legs and pulled them over her own legs. Trystan complied with her repositioning of his body before she placed a kiss upon his lips and pressed his head towards her shoulder. "There, that's the position a girl in your position should have, total submission," Natalie whispered into his ear with a smile upon her face. Natalie words prompted Trystan's member to stir. Natalie could sense his arousal immediately. Natalie whispered, "You like being my maid, don't you?" Trystan nodded as his head continued to rest on her shoulder. "I like it," Natalie responded before she brushed his face and motioned for him to move his legs off of her. Trystan wondered what his wife was doing as he reached under his dress and began to remove his waist cincher. Trystan felt the panty briefs of his cincher moving down his leg as his erection sprung to attention as it was released from its prison between the cheeks of his rear. "So nice," Natalie said as she hiked up the skirt of her dress, revealing to Trystan that his wife was not wearing any panties. As she began to straddle Trystan and work herself up and down his shaft at her own pace, Trystan realized that he had never been happier in his life than he was at that moment as wife illustrated once more that she was firmly in command of their relationship. ----------------------------------------------------------------------- Trystan continued working as he did the first day for the rest of the week. Natalie continued to order him about, but Trystan found that her demanding nature was a turn on, especially given their dalliances each night and the playful way she teased him and groped him as she helped him adapt to the trappings of his domestic femininity. As the second week began, Natalie called over to him, "Minnie, I need to speak to you." "Yes, Mademoiselle," Trystan replied almost instinctively. "When are you planning to go to the store?" "What store?" Trystan asked. "The grocery store. There's no way that you didn't notice that we're running low on a lot of things." "I noticed, Mademoiselle. I just didn't think..." "You certainly don't think I'm doing it, do you? What do I have a maid for?" "How can I go out like..." "Okay, Minnie, I'll give you that," Natalie interjected before she added, "You can wear my husband's clothes out. Of course they'll be over your body." "Pardon," Trystan asked for clarification as he was confused by Natalie's separation of 'Minnie's' body from his own. "You can go in with your short hair, and cover those boobs with one of his shirts and his coat. In fact I'll pick out the outfit for you." "I don't want to trouble you, Mademoiselle," Trystan replied, desiring to select his own clothing as opposed to being at his wife's mercy. "It's no trouble at all," Natalie replied with a smirk as she hurried towards their bedroom with Trystan in toe. Trystan watched as his wife placed a short-sleeved, button down shirt and a t-shirt on his bed as well as a pair of skinny leg jeans and his red converse sneakers. With the clothing selected, Trystan removed his maid's dress and wig. He went to remove his stockings, but Natalie stopped him and said, "No, you're going to wear the rest of that underneath your clothes to help remind you that you're still my maid." Trystan blushed as he understood what his wife previously told him about how 'Minnie' would look in his clothes. Trystan wondered how he would look with his feminine underwear and shapewear beneath his male clothing. The thought made him cringe. As Trystan stared blankly at the male clothing on his bed while he remained in thought, Natalie began to tap her arm impatiently. "Would you just get it over with already," Natalie shouted at Trystan as her patience ran out. Trystan blushed as he nodded and grabbed the t-shirt first. Trystan realized immediately that his breast forms would stretch the shirt out so he put it to the side and asked his wife if he could just wear the button down shirt as his top. Natalie smiled as she replied, "Of course." Trystan put his hairless arms through the short-sleeved button down shirt and began to button it, starting from the bottom. Trystan realized that the shapewear on his hips was keeping the shirt loser than normal in his midsection as he made his way towards buttoning the shirt over his bust. As he buttoned the first button over his fake breasts, Trystan realized that his shirt was pulling away from his body. He turned towards Natalie as she tried her best not to laugh at how feminine her husband looked in a man's shirt before he realized that he could not button the top two buttons of the shirt, leaving his fake cleavage exposed. "That's the trouble with being stacked," Natalie replied in a serious tone before she began to laugh, unable to control herself any longer. Trystan blushed at the thought of going out in the shirt, but he knew that he could cover it up with a jacket. Trystan reached down and picked up the jeans next. He slid his legs through the jeans without issue, but Trystan noticed that it was harder to pull up the zipper despite the additional weight he had lost the prior week. As Trystan struggled with the zipper, he realized that his butt pads were the likely source of his difficulty. Natalie smiled at his trouble pulling up his zipper as she remembered the strange looks he gave her when she struggled with her zippers while bloated. After contorting his body in different ways for over five minutes, Trystan was able to finish pulling up the zipper and buttoned his jeans. Trystan felt uncomfortable in the too tight jeans as he reached for the sneakers and struggled to put them on his feet. Trystan was relieved to see that between the jeans and the tops of his sneakers, his stockings were fully covered. As Trystan breathed that sigh of relief, he caught his reflection in his wife's mirror. Natalie smiled as he made his way towards it and shook his head. He looked at his body and saw how feminine his rear looked in the tight jeans. The exposed false bust that emerged from beneath from the shirt he could not close made him feel as if he looked like a bimbo from the neck down. Trystan then noticed that in his haste to get dressed as his wife instructed, he had not taken off his makeup. "Were you going to tell me about this?" Trystan asked his wife as he pointed to his face. "I wanted to see if you'd remember on your own," Natalie replied honestly. Trystan shook his head at his appearance before he went into the bathroom and removed his makeup. He styled his short hair that had been rendered a mess by the wig that had been compressing it. Once he finished, Trystan emerged from the bathroom. He headed down the stairs and grabbed the black wool coat that his wife left out for him to wear. Trystan closed the jacket and realized that the manner in which his false bust pushed the jacket away from his body still looked strange, but he knew that it was the best he could manage under the circumstances. Trystan took his keys and walked out the door towards his car for the first time in over a week and a half. Trystan started the vehicle and drove down to the local supermarket before he parked and went inside. As Trystan walked through the store, pushing the cart around the store while he picked up the items Natalie told him to, he felt as if the eyes of every person were upon. While the majority of the shoppers and employees did not notice him, some of them did. Trystan's large feminine rear in his jeans prompted more than a few stares. Some of the women who noticed were actually jealous of it. Trystan was able to use to the cart and coat to largely keep the impact of his breast forms from being noticed by anyone. As an attractive girl passed by him, Trystan caught himself leering at her. The woman's suggestive dressing was turning him on, causing his member to enlarge in his panties and poke at the back of his jeans. Trystan realized this and tried to get his erection to cease, but a teenage clerk noticed his tucked away erection and began to laugh. Trystan jerked his head towards the boy and two other employees as the clerk pretended that his wrist was limp. Trystan realized that the boy was making fun of him so hurried out of the lane with his cheeks bright red. Trystan felt foolish as he continued to shop and tried to avoid those that were aware that his member was tucked away between his legs. When Trystan picked up the last item, he hurried towards the checkout counter and waited on line. Trystan realized that the bizarrely not masculine way his coat was held away from his body by the breast forms was obvious as he was bending down to put the groceries onto the conveyer belt. The clerk noticed to, but she could not figure out why the coat was hanging off Trystan's body the way it was as she processed his purchases. Trystan paid for the groceries and headed out of the store as quickly as he could. Trystan tried to angle his body away from others as he loaded up his trunk and placed the cart the shopping cart return. Trystan then hurried to his car and drove back to his home. Trystan felt relieved to be back in his home after the shopping trip. After he put away the perishables, Trystan changed back into his maid's dress and heels. He then put on his makeup before he put away the remainder of the groceries and turned his attention to making Natalie's lunch. Trystan felt that it was strange to feel more at ease in a maid's uniform than his own clothing, but he knew that the situation he found himself in resulted in that being the case. The rest of the day and his month continued on much like the previous week. Trystan fell back into the routine his wife had increasingly turned into a formal regime for him. As the month continued, Trystan found himself going through the same motions each day. He would wake up at six each morning to get the house ready for his wife. He would have coffee ready for her whenever she got out of bed. Trystan would get fully dressed in that day's uniform and put on his makeup before he set the table as he waited to cook her breakfast. Trystan was careful about how he put on his uniform as his stockings always had to be straight for his wife's morning inspection. It was one of three inspections she worked into the day. Before each meal, she inspected his appearance from head to toe. If he was not immaculate looking at any time, Trystan knew that he would spending a fair amount of time during the meal beneath the table while she ate. As the situation turned him on, Trystan found himself increasingly making sure that his appearance was always a little disheveled in order to earn his 'punishment.' After breakfast and his 'punishment,' Trystan cleaned up the kitchen before he would head up the stairs to the master bedroom. Trystan then made the bed and brought whatever clothing was strewn about the room into the proper bin for washing. While in the laundry room, Trystan would press the outfit Natalie selected for dinner before he would return down the stairs to see if she needed anything special before he turned to his chores. Usually, Natalie would find some odd thing in the home to make him bring her before she let him get to his daily labors. Trystan would then begin to clean the home. He rotated which rooms he cleaned by the day, but the rooms that were constantly used, such as the master bedroom, bathrooms, dining room, great room and the kitchen were r cleaned each day. Trystan took to cleaning one basket of laundry a day, doing white wash on Mondays and Thursdays, dark wash Tuesdays and Fridays and hand washing the intimates on Wednesdays and Saturdays. After his morning chores, Trystan returned to the kitchen and began to make his wife's salads. Once he finished, Trystan served her lunch in the dinning room. Natalie enjoyed taking her time to savor her wine and salad as Trystan waited hungrily for his own lunch beside the table or between her legs. Natalie knew how much Trystan enjoyed being beneath her, and she was not shy about making him feel his position, especially once she started drinking. Once Natalie's lunch was finished, Trystan ate her leftovers in the kitchen before he cleaned up the kitchen and dinning room again. Trystan took to setting the table for the dinner right after he cleaned up after lunch as the month went on. After lunch, Trystan returned to his cleaning while he simultaneously began to prepare for the nights' dinner. It was during the afternoons that Trystan also went shopping in his male clothing when the need arose as well. As dinner time neared each night, Natalie made Trystan assist her as she dressed for dinner. Trystan enjoyed serving as his wife's lady's maid and helped her into her dresses each night as he also accessorized her with jewelry at his wife's insistence. When they finished, they headed back down the stairs. Trystan would finish preparing the dinner and serve her in his maid's dress while she sat at the table in her expensive designer finery. After Trystan placed the food upon his wife's plate, she would inevitably point out, with mock disdain, the flaws she noted in his appearance before he was ordered beneath the table until she needed to be served something else. As the month continued, Natalie's wine consumption ended with dinner. She began to require him to immediately fix her an Irish coffee after dinner. Once he finished preparing it, he was required to serve it to her in the great room before he was permitted to eat her leftovers and clean up the kitchen and dinning room. Once Trystan finished cleaning up and eating, he joined his wife in the great room where she rewarded his service with sexual pleasures that frequently involved things that he never imagined. When they finished around 9 pm, Trystan was sent to bed to get a good nights rest before they repeated the routine again the next morning. Trystan frequently found himself exhausted by his bedtime and felt relieved to take off his shoes. Still, as he drifted to sleep each night, Trystan could never remember feeling more fulfilled than he was. Trystan could not believe that the simple pleasures he felt being his wife's uniformed servant. ----------------------------------------------------------------------- As the month was drawing to a close, Natalie heard a knock upon the front door and figured that it was the deliveryman there to deliver the special uniform she had purchased for Trystan's last day as her maid. She drew the door open and stared with a slack jaw at the woman standing before her. "Natalie," the short haired, heavyset woman exclaimed. "Nina, oh, my God," Natalie replied as she stepped out the door and absent mindedly asked her friend from college to enter her home. Trystan did not recognize Nina's voice even though they had gone to college together, and he had spent sometime with her when she visited the area on business over the years. Trystan figured that the box that Natalie had been hinting about had arrived. Trystan turned the corner towards the hallway leading to the front door and paused as he saw Nina. He scurried out of view, but Nina caught sight of him and asked, "Who was that?" "That was just, Trystan," Natalie replied. "I can swear that I just heard high heels clicking on the floor though." "Maybe it was just water in the pipes," Natalie replied. "That's not the sound of water in the pipes," Nina responded. "Well, can I get you anything?" Natalie asked. "No. I don't want to be a bother." "It's not a bother. It's not everyday that an old friend stops by unannounced." "Is this a bad time?" Nina asked. "No. It's fine. Everything's just fine," Natalie said with a forced smile. "You were never any good at lying," Nina replied. "I know," Natalie said as she rubbed her forehead as Trystan tried to hide himself in the kitchen where he was trapped. Trystan realized that it was Nina as he did his best to hide himself. He remembered how Natalie and her other friends used Nina to help make them look more attractive. She was easily the least feminine and heaviest of the girls that his wife associated with. Nina stared down at her friend who was several inches shorter than her as she tried to figure out what was wrong. Remembering the many pretty boy jokes she made at Trystan's expense over the years, Nina asked, "What's wrong? Did Trystan leave you for some pretty boy or did he make himself too pretty that you couldn't take it anymore." "Nothing like that," Natalie replied as she rubbed her forehead. "Well, that's good because it would a damn shame if I had to come back and kick his ass for not treating you right," Nina replied as she shouted back towards where she saw Trystan. "No, he's never been better to me," Natalie replied truthfully. "Why doesn't come out and say hello to me? The way he was scurrying, I'm sure he saw me." "Oh, right, now?" "Yes, why not?" Nina asked. "Could you hold on just one minute," Natalie replied as she hurried down the hallway. As she scurried into the kitchen the smile left her face as she looked for her husband and found him hiding between the stove and the kitchen island. "Get her out of here," Trystan said in a low, desperate voice. "She wants to see you." "Now? I can't be seen like this." "Don't you think I know that," Nina said in an aggravated whisper. "What are we going to do?" "I'll bring her into the living room. You just sneak up the stairs and get changed." "Okay. Okay," Trystan replied as Natalie walked towards Nina. "He's just finishing up something in the kitchen," Natalie called out to Nina as she walked back towards her. "Trystan's in the kitchen? Retirement has been good to you both. Is he your little housewife, now?" "Something like that," Natalie said with a smile as she led her friend into the living room. As Trystan heard them walking to the living room, Trystan got to his feet. He took off his heels and waited a few minutes before he began to creep towards the stairs. He crept down the hallway as Natalie and Nina chatted in the living room. Nina noticed something from their college days on the wall and got to her feet as Trystan neared the stairs. "I'll get that for you," Natalie hastily said before Nina turned and saw the figure in the maid's outfit trying to ascend the steps with a pair of fetish heels in its hands. "When did you get a maid?" Nina asked as Trystan froze. "And what a maid," Nina added as she realized the fetish nature of the maid's uniform. "I can explain everything," Natalie said as Trystan turned towards her. Nina caught a glimpse of Trystan's face and based on the size of the maid standing on the staircase, she was able to realize that she was actually looking at Trystan in a maid's outfit. "This explains a lot," Nina said as she turned towards her friend. Trystan got off the stairs and asked, "What's that supposed to mean?" "Well, a girl like her and a guy like you, I always had my questions." Trystan glared at her as he replied, "I was a football player." "Yah, but second string," Nina retorted. Trystan went to respond, but Natalie put up her hand and looked at him while she ordered, "Put on your heels, Minnie." Trystan glared at his wife for using his feminine name in Nina's presence. "Minnie? That's a perfect name," Nina said as she shook her head. "It's not even a good name," Trystan muttered as he pouted while he placed his heels back on. "Okay, let's just all calm down. I'll explain everything. Minnie, go get us some wine while I talk with Nina here." "It's Trystan." "That cats out of the bag, Minnie," Natalie responded as she shook her head at her husband's protestation. Trystan grimaced as he turned and walked into the other room to get a bottle of wine and glasses for Natalie and Nina. Trystan came back out carrying a silver tray upon which rested a bottle of wine and two glasses for the girls. Nina stifled herself from laughing as she realized that Trystan was really serving them as if he was nothing more than Natalie's domestic. Trystan poured each girl a glass before he placed the sliver tray down on the table. Trystan then stood to the side while Natalie began to explain everything to her friend. Natalie looked at her friend as she described the boredom that had set in on their lives after they retired. She then told Nina about the series of bets that she and Trystan had made that had led to Trystan being her maid for a month. Nina reacted better than Trystan and Natalie had expected. While Nina was open-minded, they were surprised that she did not have any objections to how they were living their lives. As they continued to talk, another knock was heard upon the door. Trystan hid himself as Natalie answered the door and signed for the package from the deliveryman. Natalie called Trystan over and said, "Please take this up to our room." Trystan nodded before he picked up the package and carried it up the stairs. When he came back down, he walked back into the room where Natalie and Nina were sitting and could see that Nina was a bit flustered. He began to wonder about what Natalie had told her before Natalie looked over at Trystan and said, "Minnie, please get Nina a glass of water." "Yes, Mademoiselle," Trystan replied prompting Nina to chuckle again. As Trystan walked out of the room, he paused as he noticed that his stockings felt strange. Trystan reached down and adjusted his stockings and garters with the tips of his fingers as Natalie had scolded him to do earlier in the month. Nina smirked as she watched him doing it. She turned to Natalie and let out laugh while she said, "Wow! I've never been that girly." Trystan blushed as he picked up his head and hurried towards the kitchen to get a glass of water for Nina. After he filled the glass, Trystan carried it into the living room and placed it down on the table before Nina. Nina looked at Trystan and said, "Minnie, I'm sorry if I embarrassed you." "No worries," Trystan replied. "No. I shouldn't have said anything. This clearly works for you." "What do you mean?" "I can understand that you're more girly than most guys." Trystan gave Nina an offended look prompting her to add with reddened cheeks, "And I say that as a girl whose long time boyfriend left her for a woman he called a real woman because he thought I was too butch." Trystan nodded as he remembered hearing her tell him and Natalie that was why her ex-boyfriend broke up with her over two years earlier. Trystan shrugged and told her not to worry about it. Nina breathed a sigh of relief as she began to joke around with Natalie about their college days before the subject turned back to Trystan being dressed as a maid. Nina smiled as she asked, "So what are you going to make him do if he loses the bet tomorrow?" "I haven't thought that far in advance," Natalie responded with a lie because Trystan was in the room. "How about you Trystan?" Nina asked. "Oh, she'll get hers," Trystan replied. Natalie smirked as she thought, 'Anything you can think of for me I'll make ten times worse for you.' Nina smiled as she asked, "I know that Natalie's enjoying this, Minnie, but do you get anything out of this?" Trystan looked to his wife to see if she wanted him to answer. Natalie answered for him, "Minnie gets a lot out of this." "Like what?" Nina asked. "She's lost another ten pounds. She's never been this thin, at least since I've known her." 'To be honest that wasn't a goal,' Trystan thought as he looked down at his thin body that was much different than the muscular body he had when he was a collegiate athlete when they met and the slightly pudgy body he had before the crash diet his wife put him after she won her first bet. "She's never had more stamina either," Natalie added before darting her eyes towards Trystan and smirking. Nina briefly choked on her water as Trystan blushed as both he and Nina wondered if his wife was serious given that neither believed that he was as fit as he was when he was in playing shape. "I bet you're mistress is getting more though," Nina said to Trystan once she stopped choking. Natalie responded once more for him, "There's no doubt about that, but that's the natural order of things." "Natural order?" Nina said. "Yes, the maid lives to please her mistress, not the other way around." Trystan blushed as he nodded in agreement with his wife's words. "You two take this stuff very seriously," Nina said as she marveled at Trystan and Natalie's relationship. "Yes, we do," Natalie replied. "Can I get in on this betting for a month?" "Why would you want to do that?" Natalie asked. "I think it'll be fun." Natalie shrugged and turned towards Trystan and asked, "Minnie, do you mind if we play with someone else for a month?" "Whatever you want, Mademoiselle," Trystan answered. Natalie laughed as she replied, "I'm not asking you as my maid, Minnie, I'm asking you as my...lover. I don't want to do this unless you're on board." "I understand. My answer remains the same, Mademoiselle," Trystan responded. Natalie smiled as she turned towards Nina and asked, "So what do you have in mind if you win?" "If I win, I want the two of you to come to my home for a month and serve as my personal maids." "Oh, I think Minnie would love that," Natalie said with a smile as she turned towards her husband. "That's a deal, but before we make the bet, you should hear what you'll have to do." "Okay." "If either myself or Minnie wins, and I'm sure that I'm speaking for her here, you'll have to let us give you a girly-girl makeover. Oh, and unlike Minnie, I won't hesitate to take you to the salon for extensions. You'll have to stay that way for a month too. I want pictures sent back everyday of you at work in the super feminine outfit and makeup I'm going to get for you." "Well, what about you and Trystan. What will the loser do?" Nina asked as she blushed while thinking about what her coworkers would say about her potentially, suddenly hyper feminized appearance. "Whatever we want the loser to do. We trust each other, so we don't have to say it aloud before we make the bet." Trystan nodded, sure of what he would make her do and what she would make him do. "When do you make the bet?" Nina asked. "Usually, the last of the month," Natalie answered. "Oh, I've got to get going today," Nina replied dejectedly. "No worries. We'll make a special exception and move it up one day for you." With the agreement made, the three conceived of something to bet upon. Trystan got back to work while the girls waited to see who would win the bet. Shortly after he heard Nina celebrating, he realized who had won it. He walked into the room and saw Natalie hugging Nina before they told Trystan the obvious news. As Nina prepared to leave, Trystan knew that he would be seeing a lot more of her as he prepared to serve her for a month beside his wife. Trystan hoped that the next month would prove as fun for him as that month had been for him, but he wondered if things would take an unfortunate turn once he went to work in someone else's home. --------------------------------------------

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Hello all, this story is real-life incident which happened between my lovable dad and hot maid. My dad is a handsome person in his early 60s. My mom is a homemaker. I am their only son who witnessed the hot sweaty sex between my dad and maid. We had a maid – a divorced woman of 45 years who used to take care of household works. She has a slightly brownish skin tone and is slightly chubby with fat in the right place. The main highlight is the fold in her hips. She wears her saree in such a way...

4 years ago
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The Indentured Maid

The Indentured Maid By Janis Elizabeth Devon Lindsey had two passions in his life, neither of which he could or would reveal to his family and friends. First was his love of wearing women's clothing, a love that first began in his pre-teen years when he had found a pair of his mother's silky panties folded on top of the clean laundry in the basket. When he touched them, he felt an exciting sensation go through him, a sensation that caused him to hurry to his room and try on this...

2 years ago
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Lady Heathers Maid

Lady Heather's Maid. By Trish. This is the story of how I was seduced from a university course that bored me into a life of skirts and service to Heather Lane. I first heard of Heather when I was about thirteen. It was after school one evening and as usual my mum was picking me on her way home from work. I was on first glance a typical teenage boy in most respects, for instance I was not happy about being forced to sit in the back because mum was giving Edith, her best friend a...

2 years ago
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Friends mother and maid

Hi this is Jairam 26 year old from Hyderabad, India. I’m average guy without any bad habits. But I’m very interested in sex right from my childhood, you know what I mean. I was more attracted to the boobs and belly buttons. The story which I’m going to write is not a real story. The story is about my friend’s maid and her mother Sunita. Sunita was not very beautiful, but was having good amount of flesh at the right places. She is 42year old with 38, 27, 38 measurement. I was very close to...

Incest
3 years ago
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From Man to Maid

From Man to Maid Donna and I had been living together for six months when the changes started. It was a Friday night and I was the first to arrive at our apartment after work. Then I heard a key in the front door. Donna came bounding into the living room with a huge grin on her face. I rose to greet her. She wrapped her arms around me and we kissed. "How was your day Bill?" "Same shit, different day. Answer the phone. Stare at the computer screen. Process the paperwork. ...

4 years ago
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A new maid

"Life can't get much better than this," Jack thought aloud as he laid around his family pool. Jack was the heir to his family's vast fortune and constantly thought that this made him better than everyone else. This was especially true with regards to his younger sister. Jack was 19 years old and loved to threaten his younger sister, Jackie, about how if something ever happened to their parents she would find herself penniless and destitute. The thought of his 18 year old sister...

Horror
4 years ago
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Made To Order Maid

Maid To Order Mr. Carstairs shuffled to the door and managed to stand fully upright in order to hug and "air kiss" his wife goodbye for the day. "Now honey, remember what the doctor said," she reminded him. "Keep taking your heart medications and try to keep calm. Remember your blood meds too!" she chided him as she stepped out the door and off into her Porsche. "Don't worry, dear, I won't forget!" he promised as she sped away. Mr. Carstairs then shuffled himself over to his...

4 years ago
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Breeding My Familys Filipino Maid

I lay awake naked on my bed, staring up at the ceiling in the dark. We were going through another blackout and the air conditioning was dead. The sweltering Bangkok heat was unbearable, even in the middle of the night. I couldn't sleep anyway; I was a few months over 18 and my near-uncontrollable sex drive had no outlet. My big cock was a steel pipe that I gripped and pumped in my hand, lubed up with a palm of spit. I was frustrated; I was a good-looking white k** from a well-off American...

4 years ago
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Justine The Maid

The next few days were bliss.  Justine rushed home from college each day to be transformed into Aunty Sophie’s niece as she tried on all the outfits they had chosen at the shops.  Justine, with a bit of makeup and the right clothes had become a beautiful young woman.  She learnt the power of a peeping lacy slip could make men weak at the knees.  Sophie also lent Justine some more lingerie until she was able to build up her own collection. Perhaps they would make another trip to M&S at the end...

Incest
4 years ago
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Lust Adventures 8211 Part 2 Laid With Maid

Hello readers, this is Rahul and it has been a while since I last visited ISS. Thanks for the overwhelming support for my first story. If you haven’t read it yet, please go read it. In continuation to my first story, it’s been 5 months since then and whenever my sister visits home, I used to find a chance and fuck her. After 5 months, my brother-in-law shifted to Canada and so was my sister. What the hell!!!! All the fun I had was gone and I was feeling lonely. I tried to get busy with work...

4 years ago
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Maid

Copyright© (c) 1994-2003 "Oden the bardling averred His muse was the bum of a bird, And his Lesbian wife Would finger his fife While Fisherwood waited as third." -author unknown She came highly recommended, with references and a resume that greatly impressed me. The children loved her, my wife was thankful of the excellent work she did, and I was able to spend more time with my work. The maid also entered my family and began to systematically control or terrorize everyone in the...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

2 years ago
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The Resort Maid

The Resort Maid Belladonna Elias Dara and his wife, Mariasela, exited the bus with smiles on their faces as the warm wind off the Caribbean Sea brushed against them as they stepped onto the resort's grounds. They followed their fellow travelers towards the check in desk while the resort staff began to unload the luggage from the bus. As Elias followed behind them, hand in hand with his wife, he smiled as he thought about how his vacation was going to be far different than that of...

4 years ago
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The Master the Madam and the Maid

The drive to Don and Carol’s isn’t far but traffic was snarled making the journey irritating. It had been an arduous work week for both Jean and I and we were looking forward to the evening as we always do to these special get-togethers.Jean and I are married, in our late fifties and began swinging about eight years ago. Jean is 5’ 8’’ tall, a slim blonde who could easily pass for 38. She has small breasts with large, erect nipples, an ass to die for and a multiple orgasmic pussy topped with...

1 year ago
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The Master the Madam and the Maid

The drive to Don and Carol’s isn’t far but traffic was snarled making the journey irritating. It had been an arduous work week for both Jean and I and we were looking forward to the evening as we always do to these special get-togethers. Jean and I are married, in our late fifties and began swinging about eight years ago. Jean is 5’ 8’’ tall, a slim blonde who could easily pass for 38. She has small breasts with large, erect nipples, an ass to die for and a multiple orgasmic pussy topped with...

Swinger
4 years ago
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Summertime Maid

It was all in place for Leo Munby. He had sold the company that he had built from the ground up for over 100 million dollars. He had given 20 years to creating that company and now he was going to enjoy the middle years of his life. The deal was signed. He had bid goodbye to all of his employees and returned home from the office for the last time. He exited the building through the servant's entrance as he often did. The feeling of walking under that sign always gave him a thrill. Of...

2 years ago
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The Patched Up Maid

THE PATCHED UP MAID It all started when I was first seriously dating Carla, my soon to be wife. Well no, I suppose it really started when I was about six or seven years old. That was when I first discovered the wonderful feeling of my older sister's underwear. I got hooked and although I tried to kick my compulsion many times, I knew I had to tell the woman I was going to ask to be my wife my little secret. I admitted that I was ashamed of what I did and she agreed. Carla...

4 years ago
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Boarding School Encounter 04 Miss Marilynn Molests the Maid

Chapter Four: Miss Marilynn Molests the Maid By mypenname3000 Copyright 2016 “Miss Marilynn! Missy Marilynn,” a panicked, feminine voice called, reaching into the confused thoughts of Marilynn Gully, the young philosophy teacher at The Kensington Boarding School, an all-girls school in the English countryside. “Please, please wake up, Miss Marilynn.” What happened? the teacher wondered, trying to organize her thoughts while her body lay limp, her eyes closed. She felt the hands push on...

2 years ago
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My Father The Maid

My Father, The Maid, by Oona. I thought it was really weird when I received the random text from my step mother, even though I had known her for most of my adult life as my father's new wife we had never really been close. Hell, for that matter I had never really been close to my father either, he was always pulling long hours at the office when I was young, so he was never around. Nowadays I rarely if ever saw him, once a year for Christmas at most, and maybe a text on my birthday....

4 years ago
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Made to Maid

Made to Maid name of author withheld by request Part I It was great having my own car. Even though it was a just a used Neon, I didn't care. A car was a car. My parents had bought it for me only a few weeks ago for my 18th birthday. And today, I was making the drive by myself from Omaha to Chicago for a cousin's wedding. I was shocked when they said I could make the drive myself, but happy to have the newfound freedom. Having left after school, I knew it I wouldn't make it...

4 years ago
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Becoming a Career Sissy Maid

I have been submissive for as long as I can remember. Growing up I adored my mother and would watch everything she did around the house. Eventually I would help her with more and of the cleaning, cooking and laundry. She playfully called me her maid when I was helping her and I began to refer to her as Ma'am. When I was 13, we decided that I should go to a friend's Halloween party as a French Maid. For some reason this really excited me! My first masturbation fantasy was imagining...

4 years ago
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The Happy Maid

THE HAPPY MAID "You don't need a husband, Carol dear, you need a maid," Tina West told her best friend. "I know you're well paid but the idea of you going home and being the little housewife makes me shudder. How do you put up with it?" "It's not quite as bad as you make it sound Tina, Norman usually does the cooking and other household chores. He knows that his job isn't as demanding as mine. The trouble is that I still feel that I should look after him better than I...

1 year ago
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Connie The Junior Maid

CONNIE THE JUNIOR MAID by Monica Graz PART 1 - Connie becomes a maid My name is Connie and I'm a 23 years old gender fluid male. I work by choice as a full-time live-in housemaid for almost a year now. But let me tell you my rather unusual story and how it all started. I was born as Michael (Mike) Allen the only child to a well-off family and I grew up as a privileged boy going to the best private schools and eventually to a prestigious university where I was studying...

2 years ago
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My First Experience As A Maid

My first experiences as a maid Hi, I am Mariëlle (28) and I like to tell you about my first experiencesas... a french maid! I hope my (rather naughty) story does not only turn youon, but may also inspire you. I know there are a lot of people (both men andwomen) who fantasize about being a maid or having one, but usually people don'tspeak our about it. Not even to their partner, because they feel ashamed orsomething. Something they shouldn't be! I have had submissive feelings as long as I know....

2 years ago
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Friday Night Maid

Friday Night Maid - By: Diane Leonard I am a Friday night maid. After a week of hard work, I relax by dressing up in a sexy maids outfit and serving, pleasing and pleasuring my wife. While she is out dancing with her friends, I am dressed up as a Friday uniform waiting for my wife to return home. She doesn't like my fetish, but this agreement, once a week seems to work for us. But this last week was to be totally different. It started out like any other Friday night session. I...

4 years ago
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Transformation Finale The Maid

The maid. I open my eyes and stare at the ceiling. I feel the smooth silk of the sheets against my skin and revel in the sensation. My mind flicks through the miriad of bodies I have inhabited over the last few months. Despite the different faces one thing has been constant, the fact that they were all submissive, something I now relate to. I look around, It appears by the light through the blinds that it is early morning. I rub my eyes.......wait! Those are my hands, I am back in my...

4 years ago
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Boarding School EncounterChapter 4 Miss Marilynn Molests the Maid

“Miss Marilynn! Missy Marilynn,” a panicked, feminine voice called, reaching into the confused thoughts of Marilynn Gully, the young philosophy teacher at The Kensington Boarding School, an all-girls school in the English countryside. “Please, please wake up, Miss Marilynn.” What happened? the teacher wondered, trying to organize her thoughts while her body lay limp, her eyes closed. She felt the hands push on her. Who is that? Daisy? ... disconnected... an alien voice whispered through...

4 years ago
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Forgetful Maid

Forgetful Maid by Sally Tranz 1 - Dressing for Sunday chores My silent alarm buzzed and my arm jerked slightly as the watch brought me out of my light sleep. Although it had been a late night, I rarely slept past 7am, but Sunday was a special day. Sometimes, the alarm was set as late as 9am, which meant that I lay in bed even when awake. Sunday was the day my lady was treated very special. Today it was 7.30. As I eased out of our bed, the gentle breathing of my lady reassured...

1 year ago
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My first experiences as a french maid

Hi, I am Mariëlle (28) and I like to tell you about my first experiences as... a french maid! I hope my (rather naughty) story does not only turn you on, but may also inspire you. I know there are a lot of people (both men and women) who fantasize about being a maid or having one, but usually people don't speak our about it. Not even to their partner, because they feel ashamed or something. Something they shouldn't be! I have had master I could serve. I decided the internet was a nice...

Fetish
2 years ago
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My New Maid

My New Maid By Margaret Jeanette Sarah and Jim Toomey were enjoying a steak at their favorite steak house. He was looking all around and observing the other patrons. "What are you looking at?" "I am just observing all the customers. Do you notice all the men are wearing dark suits and all the women are wearing bright, colorful outfits? Look at the woman at the table next to us. She is wearing a bright yellow blouse with lots of ruffles on it. She looks so feminine. Look...

4 years ago
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The Regents Maid

This is a role play between darknessmonger and Aurelié Catena It is written in third person so it can be read as a story instead of those roleplays that switch between characters. The rules of the game are: Aurelié decided on a torture that would break her and darknessmonger had 7 days to figure it out by noticing the hints on her reactions, and taking care of not overdoing and losing her. So, do you want to know who won? Read on. Introduction Aurelia is a maid at the Regent’s castle. At least...

2 years ago
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A Faithful Maid

James felt a hand on his shoulder as he slept but ignored it.“Young Master.” A female called out, at the same time shaking him again. “It’s time for you to get up now.”“Just a few more minutes… please, Paulette.” He flipped onto his side, putting his back to her.She giggled. “I’m not falling for that one again, mister. Last time, it took you almost an hour to get ready.”Letting out a sigh, he finally sat over the edge of the bed to see the woman standing in front of him. She was...

Mature
4 years ago
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The Feminization Amy Maid

[ ] A long day of cooking for a group of angry men who are all big brutes that make iron slabs all day had me horny and ready to beg one of them to let me suck him until he got hard like a iron rod and bend me over to fuck me deep in my ass. Yet I was to scared that I would be called a fag or worse. I came into my bunk to sleep and I had a toy that I was going to use under my covers to satisfy my needs for a man. It was not a good comparison. The room was occupied by me and three men that were...

3 years ago
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Sex With My Hot Maid

Hi, Last month my regular maid went on holiday for 1 week. After 1 week she didn’t come so we got a new maid. Her name was sarika. She was around 30 years old. She was average looking slim and dark. She had small breasts. She had very less fat and her ass was a nice tight one. She would wear sarees or Punjabi suits. When I saw her for the first time my dick rose immediately! She wasn’t very good looking but her body was good! She was wearing a Punjabi suit and her ass was just awesome! It was...

2 years ago
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Forever Maid

He brought in the mail. As he looked through it there were 3 identical envelopes. One addressed to Josh, one to Mike, and his. The return address was just a symbol. He set the other two on the kitchen table for Josh & Mike, and opened his. Inside was an invitation to a Halloween party called "The French Maid Ball". Also, there was a credit voucher for a place called The Pleasure Pit. He had never heard of it. He looked back at the invitation again. The address of the party was in a...

3 years ago
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The Maid

I was tasked to host a dinner party for the president of the company coming to Los Angeles from New York. He was here to see how the West Coast office was doing and if they needed anything in light of the economic downturn the country was going through. They had already closed one of the Midwest offices in St. Louis and broken that office up, sending the personnel to the other offices elsewhere. Obviously, my boss, Mr. Chapman was not interested in moving away from the sunny California home he...

2 years ago
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Unexpected Maid

Unexpected Maid It was 7 o'clock in the evening and I'd been looking forward to tonight. I'd got a decent excuse for a night out with the lads as my wife Hannah had invited about a dozen of her friends round for wine, nibbles and probably a bit of Singstar as the evening progressed and the alcohol flowed. I was happy to get out of the way, meet the guys, probably go for a few beers and a curry. The gathering wasn't due to start for another hour so I was idly browsing at the PC...

3 years ago
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How I Became an Asian Maid

"Great. Just fucking great..." I muttered to myself as I banged my head against the steering wheel in frustration. My name is Jake Francis and I've been having a terrible week. So terrible, in fact, that I feel close to losing my mind. First the girl I've loved for two years broke up with me, then earlier this week my father died of old age. My mom had already died a long time ago ago, so apart from some distant relatives I never talk to I'm the last remaining member of...

3 years ago
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Mallika sherawat8217s maid

Hi, Hello everybody. This is a sequel of my first story Erode’s mallika sherawat in the couples category, this all started due to an accident. And I also forget to tell the aunty’s name in the story, her name was kalpana. We have fucked three to four times in those two days when she was all alone but afterwards there was no opportunity for us to enjoy each other, but at that time we enjoyed talking on the phone whenever she find time she used to call me and many a times we enjoyed phone sex in...

3 years ago
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The Ruined Maid

Don Clarke walked on the sidewalk that ran along the Happy Hills strip mall. Don was the only owner the building had never known. He had built it on the grounds of a shuttered tire factory 14 years earlier. Ever since he had it built, it had been a gold mine for him. It was, however, just one of his many lucrative ventures. Don had built up a fortune over the years through land speculating, and there was nary a man better at it then him. He knew the value of a dollar better than anyone....

3 years ago
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The Maid

This story takes place many years ago where there were large mansions,and the owners hired many servants to help out in the household. There was a young woman named Alice that lived a troubled life in herc***dhood. Her parents kicked her out into the streets, because she was atroublemaker and they could no longer take care of her. So Alice didanything to have clothes to wear and food to eat. This meant she got intotrouble with the law. So she spent many years in prison. Every time shewas...

3 years ago
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The Maid

I was tasked to host a dinner party for the president of the company coming to Los Angeles from New York. He was here to see how the West Coast office was doing and if they needed anything in light of the economic downturn the country was going through. They had already closed one of the Midwest offices in St. Louis and broken that office up, sending the personnel to the other offices elsewhere.Obviously, my boss, Mr. Chapman was not interested in moving away from the sunny California home he...

Uniform
4 years ago
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Blackmailed And Had Sex With A Virgin Maid

Hi, friends, my name is akshay .I’m from hyderabad.I love to fuck young and married women .I have long dick and stamina to satisfy a woman. They love to share their bed with me. Want to have sex with me you can message me at I am akshay, my dick is around 7-inch .I have an athlete body. Because I love fitness exercise and maintain my body.I had many encounters with school girls, young and married women.They always love to share there body and bed with me.   Coming to the story.This story is...

3 years ago
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Remaid

Re-maid By Lady_in_Waiting "How many times do I have to tell you to clean your room?!" Michael's mother stood in the doorway looking very upset. "If I have to tell you one more time, you'll regret it." "OK," said Michael. The usual response. He sat at his computer, talking to his girlfriend, Laura. He spent nearly all of his time there, talking to her. Michael didn't have time for things like cleaning his room. His mother stormed...

3 years ago
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Man Maid

"I am glad the weekend is almost here." said my roommate Todd. "If I can get through tomorrow, it's two days of peace and quiet with nothing to do." "Nothing to do except the dishes, laundry, sweeping and the pool needs cleaning." I answered. "Oh yeah, I forgot. No rest for the weary. Shame we can't hire a maid to do all that." "To expensive. You want a beer?" I asked getting up and heading for the kitchen. "Yeah, ok. How much you figure a maid service costs anyway?" "More...

3 years ago
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Alice the New Maid

This story takes place many years ago where there were large mansions, and the owners hired many servants to help out in the household. There was a young woman named Alice that lived a troubled life in her childhood. Her parents kicked her out into the streets, because she was a troublemaker and they could no longer take care of her. So Alice did anything to have clothes to wear and food to eat. This meant she got into trouble with the law. So she spent many years in prison. Every time she was...

Spanking
4 years ago
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My first night as a Maid

I sat up slowly and streched my arms out wide as i sat on the sofa, groaning a little as the aches released, and caringly draped my arms around the gorgeous boy next to me. Kyle, my boyfriend for a few years now, was sitting beside me, with me resting my head on his lap only a few seconds ago. I loved lying like that, curled up just next to him, feeling so safe and protected. I gently rested my head now on his shoulder, closing my eyes from my sleepiness. Maybe i should describe us first of...

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

1 year ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

3 years ago
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Sexy games and finally sex with my African maid

My wife used to have a job where she would have to travel one week a month.I would watch her dress and do her make up while I stroked my cock.When she was ready to leave, she would sit down beside and rub and suck me for a few minutes to finish me off. According to her that would be me good till Friday night when she got back.Actually that left me and the black African maid alone for a few days.This maid had caught us doing stuff many times. In the morning when she brought coffee my wife was...

3 years ago
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Seducing And Fucking My Innocent South Indian Maid

Hello, I am Vihayas and I am from a town area in south India. Later, I moved to Delhi for studies. I am a girl of 20 years of age but I am going to tell this story in a boy’s perspective. So, this hot story is about me. When I used to be in my hometown, I used to be a shy guy and I used to have a good boy image. We had a servant whom we called Pushpakka who used to clean our house. She was almost 36 years, same age as my mom. I was 19. Pushpakka was with us from childhood. She had a bad...

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