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Chelsea By Sissie Maid Cuckold "Chelsea! Come here this instance!" Chelsea knew that mother was mad. She did not raise her voice unless she was. She was, after all a lady and proper lady at that! "Yes Mother?" Carrie Williams was out of patience. "I did not see a curtsey young lady!" "Yes Mother." Chelsea hated to have to curtsy. It was so, so childish and girlish. Oh, why must it be done? But Chelsea knew better than to challenge mother. Soon the hem of the pretty yellow skirt was being lifted and Chelsea was dipping in unison. "Much better," said Mother. However, Darla, Chelsea's sister was not so kind. "You look like a little sissy fairy doing that Chelsea, you're hilarious!" "MOTHER! Make her stop!" "Now Chelsea if you had done what you were told she would not be making fun of you...now would she?" Chelsea's head hung as mother reminded that the reason Chelsea had to curtsy in the first place was Chelsea's misbehavior. "But mother I am 18 years old. Why must I succumb to this sort of punishment? It's not fair, Darla never gets in trouble." "Now Chelsea! I will not stand for your insolence or your lying, you know very well that just last week I scolded Chelsea for not spanking you properly!" "I forgot!" "You forgot? Your sister got in trouble because of you Chelsea. If you had not misbehaved, you would not have needed a spanking. And if you had not needed a spanking, your poor sister would not have gotten in trouble for not spanking you long enough. Now I want you to apologize to her right now for getting her in trouble!" Chelsea looked at mother in total disbelief. To apologize to Darla because she did not provide enough spankings was beyond belief. As Chelsea thought it through it was apparent that not doing what mother had said was going to lead to even more trouble. So humbled and humiliated Chelsea apologized to Darla while Darla made faces teasing poor Chelsea for doing what mother had ordered. Chelsea knew that there must be a curtsey at the end of the apology so once again fingers took hold of the hem of the yellow skirt and a dip accompanied the hem lifting much to Darla's enjoyment. When Chelsea had finished the curtsey, Darla said, "Turn for us Chelsea I want to see your pretty new little girl's party dress. Yes, turn, turn and turn some more." Poor Chelsea turned and spun the skirt out showing off her pretty matching panties. "Mother I do love Chelsea's new dress. It's so, so, juvenile and fitting for punishment. Can I make her take the baby stroller and her baby doll for a walk around the block? I think it would do her good." Mother thought a moment and said, "Yes Darla I agree, she certainly is a slow learner and that may be just the thing needed for her to get her head straight." Chelsea hated having to go out in the neighborhood in a little girl's party dress. It was so humiliating. Being seen in such a juvenile outfit and pushing a baby stroller with her dolly in it was simply so juvenile that anyone who saw her laughed. After all she was 18 years old. But even worse, worse than an 18-year-old girl having to do such a thing was that Chelsea was not even a girl but a boy. A petticoated boy constantly punished by his mother and older sister. It had all begun when he got in trouble for not doing his chores and then making it worse by saying that doing dishes was girl's work! His sister Darla was the first one to suggest that if dishes were girl's work that he be a girl while he did them. His mother agreed, and they wrestled the weak wimpy boy down and turned him into a girl. He behaved so well for a period after that, that the next time he acted out they used the same sort of punishment. Chelsea was only 5 feet tall and weighed 110 pounds. He was a runt! Both his sister and mother were quite athletic, bigger and in far better shape than Chelsea was. His real name was Chester but whenever he was bad and had to endure the petticoat punishment, they called him Chelsea to further humiliate the hapless boy. The ladies found that petticoat discipline was extremely effective and what's more a blast to apply. In fact, truth be known the ladies had come to enjoy Chelsea's punishment so much that they hoped he would screw up just so they could punish him. Chester was the most pathetic male they had ever seen. It was as if nature had made a horrible mistake. Even his face was unmanly, and his voice was often mistaken for a girl's. Both mother and daughter admired real men, branny, strong, determined, dominant men. They had no respect for wimps and Chester was a wimp. "Mother, please, there is no reason to send me out for a walk..." "That will be two trips around the block, now go and get your dolly and get going!" "But mother, please..." "Three trips...would you like to try for four?" "No mother." "Then off with you... maybe you will run into some of your friends on the way". Both mother and sister laughed at this statement knowing full well that Chelsea knew several of the families who lived around the block. In fact, two of his female classmates from high school lived on the block. Chelsea's stomach turned into knots and his heart beat fast and breathing rate increased rapidly. Oh, how he hated to make the walk and now because he was too stupid to keep his mouth shut he was going to have to make it three times! Chelsea put her baby doll, Nancy, into the baby stroller and put a blanket over her up to her neck. He had made mistakes before in not properly covering the baby doll or walking to fast, both considered an endangerment to the baby doll. The result was a very hard over the knee spanking and then double the walks! Just as he was about to depart, Darla came to check and make sure that Nancy was properly taken care of. "Three walks are going to take you quite a while Chelsea, I think you better take a bottle incase Nancy gets hungry. In fact, on your second round stop off at the buss stop and feed her." "Yes Darla." Chelsea was not looking forward to sitting in a bus stop feeding her dolly but what could she do. Darla would know if she did not do what she was told and then she would be in trouble. Chelsea prepared a baby bottle of milk, warmed it and then left. She went out her back door and around to the driveway and down the driveway to the side walk and turned right. The first 5 houses went well but as she approached the 6th house, the girl she went to high school with was walking out to her car parked on the street with the other girl he went to high school with. "Oh Jessica, look it's Chelsea again. He must have been a bad boy again! Ha, ha, ha." "Yes, CindyI bet he has been. Let's wait and ask him?" The two girls waited for Chelsea to get closer, they could hardly contain themselves they were so excited. Cindy thought It was so much fun to make fun of Chelsea. She had done so when they were in school, making fun of how effeminate he was but she never imagined at that time how effeminate he would end up being. Chelsea saw them and knew what he was in for. They would be merciless with him and he wished he could crawl in a hole and hide. "Hi Chelsea, you taking your little Nancy for a walk? Ha, ha, ha." Chelsea was red faced, so much so he could feel it burning. "Hi Cindy, Hi Jessica, yes mother told me to, but it was Darla's idea." "I see," said Jessica, "is that a new party dress you have on?" "Yes, I just got it Monday, Ms. Stokes made it." "Its very pretty Chelsea and it fits you perfectly," said Jessica. "Thank you." Chelsea did not really mean the thankyou but knew if she did not say it and it got back to his mother or sister there would be hell to pay. "Aren't you supposed to curtsey when you say thank you," asked Cindy? "Oh yes, I am sorry...thank you Cindy (and a curtsey) and thank you Jessica (and a curtsey). The girls both laughed causing Chelsea great humiliation. They had both been invited to Chelsea's petticoat punishment party. A Party idea that Darla came up with to acquire a wardrobe of feminine items to help outfit Chelsea when being petticoat punished. Two aunts and two girl cousins along with a former teacher had made up the party. All of them giving Chelsea various feminine gifts. Chelsea was quite sure his life ended that day. The humiliation was so overwhelming that Chelsea had actually begun to block it out of his mind. "Cindy smiled and said, "Do you remember Cathy Johnson and Ginger Riley? Well we showed them the photos we took at your petti coating party and they thought they were wonderful. They asked us if they could see you being petticoated. I am going to ask your mother if you can come to my house and give a little fashion show for them and us of course and maybe a few others, won't that be fun?" Chelsea was horrified! How could they do this to him. He was in totally shocking just imagining the party. Cindy interrupted his thoughts. "Chelsea! Chelsea! I asked you if it would be fun?" "Oh, oh yes, yes it will be fun." "We thought you would enjoy it. I told Jessica that I think you really like being a girl and that's why you act up so much, so you can get petticoat punishment." "Well Duh Cindy, I mean he isn't a real man anyway. Look how tiny and feminine he always looked in school. Besides one of the boys I dated was in gym class with him and he said he saw him in the shower one day and had to look three times, he was sure he as a girl at first his dicky was so tiny! Ha, ha, ha, ha." Cindy got an evil look on her face. "How tiny is your dicky Chelsea? Tell us really how long it is?" Darla his sister had measured him one day, so she could laugh at him at how short he was. She had dated some real men with dicks up to 8" long so when she saw her brother's little dicky she had to measure it. She pulled it tight and it got to 3" long. She told her mother and her aunts and cousins and even some of her friends how tiny Chelsea's dicky was. Chelsea hung her head. "It's, it's 3" long." "Three Inches! Is that all, how can you even hold it to pee? That's so small does it even qualify as a dick?" The girls made terrible fun of him as he stood there and took it unable to move on or reject them or suffer the consequences. Chelsea started to tear up. "Look Jessica, sissy Chelsea is going to cry!" Cindy enjoyed making Chelsea cry, but Jessica was kinder. "Oh don't cry Chelsea, we were just having fun. You can't help it and we know that. Let's go Cindy." The tears were dripping as the two girls left. Cindy proud of making the wussy boy cry and Jessica sympathetic. Chelsea scared that his mascara would run lifted his eyes skyward and blinked rapidly in an effort to contain the swollen tears. Soon he had regained his composure and continued his walk. As he pushed the baby buggy with little dolly Nancy in it he tried to keep his eyes focused on the baby doll and ignore all around him. He continued around the block passing or being passed by several people but none of them paid any particular attention to him. Strange in that he was an 18-year-old boy wearing a little girls party dress pushing a baby buggy. True he was quite small but still no respectable female over the age of 8 would wear a dress like the one Chelsea had on. The whole purpose of the little girl's short frilly skirt and ruffled top was to humiliate the wearer, and, in that purpose, it was being quite successful. Chelsea was totally humiliated and felt a total defeat hanging over him. He began to reflect on his plight and vowed to not disobey his mother or sister ever again no matter what. But upon reflection he began to understand that in over half of his petticoat punishment exercises he had done nothing wrong. Like the other day he was punished for Fed x being late! And before that he received another two moths of petticoat punishment because it rained. He was now aware that no matter what he did he was going to be petticoated. He could do nothing to stop the punishment or force behind it. Everyone seemed to rejoice in his petticoating. They all made fun of him and looked for ways to further escalate his petticoating. Even Cindy said, "He likes it, so he does things to encourage it. It was a conspiracy." They were all out to get him, none of them cared how he felt or how bad they made him feel...none of them except Jessica. He remembered that Jessica was the one person in high school that would ask him if he was all right or say not to worry about what others said. Maybe she would be his friend. He needed a friend, someone who cared about him. Someone he could trust. He made the one and half rounds mark and looked over at the buss stop and saw that there was only one lady sitting there so he took Baby doll Nancy out of the carriage and along with her bottle went over and sat at the opposite end of the bench from the woman. As he approached and sat down she looked over at him then she smiled. She looked his way several times while he tried to ignore her. "You're a boy, aren't you?" Chelsea tried to ignore her. "I said! You're a boy aren't you?" in a much loader voice. Chelsea nodded her head and then looked over at the woman, "How did you know?" She smiled and looked forward then back at him. "Because no real girl would wear a silly outfit like that out in public. Not now a days anyway. Your idea or somebody else's?" "My mother and Sisters idea." "Being punished?" "Yes, petticoat punishment." "Yes, I can see that. Do you mind? Would you show me your outfit, I promise I won't laugh I think it's a very pretty dress?" Chelsea began to like the lady. She was about 50, very pretty and fit for a 50-year-old woman. She put the bottle down and Baby Doll Nancy back in the buggy and walked over to the woman. She curtsied which brought a huge smile to the lady and then turned twice for her and stood. "My, my, is this custom made?" "Yes, my mother has a lady make them for me." "Them? You have more...like this I mean, little girls party dresses?" "Yes, I have four of them like this." "Oh, my and other dresses or skirts?" "Oh yes mother kept my older sisters' wardrobe from junior high and I have all of her things from back then." "Is your sister your size?" "No not now, she is much bigger than I am but in 7th grade she was my size and some in 8th grade." "Why so many outfits. Are you that bad that you need that many?" "No Ma'am, I don't think so. But I get in trouble constantly. Since I tuned 18, 9 months ago, I have been in constant petticoat punishment night and day." "Well if you're not bad why are you being punished so much?" "I think they like it! I was thinking today what I could do to stop being punished and I reminded myself I got three months because it rained the other day. Now I ask you ma'am how in the world could I help that?" "I have to admit I think they do to. Well you can't really blame them." "Ma'am?" "Oh, well I used to petticoat my husband bless his soul. It was very enjoyable, and I liked the power and control and he liked being controlled." "Really...you made your husband dress up like a girl, like me?" Chelsea was excited by what she was being told. "Did he like it...I mean..." "It's ok hon, no not at first but he learned to like it and it was good for him and for us." "I don't see how I could learn to like it." "No not now but if things were a bit different you could, you could easily learn to enjoy it and want it." "Really...I just don't see how. The humiliation and shame and the pain are all a lot to bear let alone think of them as nice." "I know dear I know. You are not getting any of the benefits out of it right now they are still breaking you." "Breaking me?" "Yes, you see the male mind thinks its above all things feminine and once it sees it is actually below all things feminine a new peace takes hold and all is well." "I don't understand?" "I don't expect you do. Who is your mother?" "Carrie Williams, Ma'am." "Where does she live?" "Why?" asked Chelsea suspiciously. "Well hon I like you and I want to help you if that is ok with you. I think if I talk with your mother I can make life a bit easier and more fun for you if your willing to give me a chance." Chelsea looked at the woman for a few seconds and found a certain trust in her eyes. What could it hurt it was pretty rough right now. "Ok, we live at 1425 Oak Dale Street. My name is Chelsea." "Its nice to meet you Chelsea, my name is Sylvia Reynolds. I will see what I can do to help you." "Thank you, Ms. Reynolds...Ma'am, do you mind if I ask you a question?" "You may ask anything you like." "Why didn't you mock me? I mean everyone else does, except well maybe Jessica." "Why would I mock you? You look very pretty in your little party dress, I like sissy boys as you now know but most important I know what value a well-trained sissy boy is. As I told you I petticoated my late husband for many years. It was a pleasure, a joy and big help. So, no I won't mock you, but I will try to help you." "Well, then why do all the others mock me?" "That's simple child, they have not learned how to get real benefits out of you yet either. You see sweetie, when petticoating is done right, everyone benefits. Its better for all besides you told me this Jessica girl does not mock you." "How can I possibly benefit by being a petticoated boy?" "You especially will benefit Chelsea. I mean look at yourself I can not imagine you trying to compete with real men. You're so tiny and feminine naturally let alone after a little feminization work is applied. Can you truly see your self competing with big strong 200- pound men? So, by learning to be a girl you are in a realm of physical size and strength you fit better into and you're not expected to perform like a real man." "I see, I guess you do have a point." "Yes, dear I do, now tell me who is this Jessica?" "Oh, she's a girl I went to high school with. She is very pretty and outgoing and very smart. She was a straight A student and a cheerleader, and she is very pretty..." "Yes, dear you said she was pretty, so how do you interact with her?" "She lives about 6 houses down from me and she found out about my petticoating through my sister. My sister Darla is two years older than me, but she was a cheerleader too so that's how they know each other. My sister loves to humiliate me, and it was her idea to let Jessica and Cindy in on the deal." "Who is Cindy?" "Cindy is Jessica's best friend and another cheerleader. They are almost inseparable, and Cindy really loves to make fun of me. She is mean like my sister and doesn't care what she says or how she makes me feel. Jessica tries to tame her down sometimes and apologies for some of the things that Cindy says and does and that's why I like Jessica." "How does Jessica feel about your petticoating?" "I don't know for sure cause we never talked alone but she truly does seem to like my outfits and tells me I look cute or pretty in them. I think she sort of likes me being a girl if you really want to know." "Yes, it sounds like she does, interesting. What is Jessica's last name?" "Ah its Phillimore, Jessica Phillimore and she lives at 1413 Oak Dale St. How's come you want to know?" "Oh, I was just wondering if I knew her, thats all. How many more times do you have to go around the block before you can stop?" "One and a half times about." "Ok well you better get on with it. I hope to see you again Chelsea." "Thank you, Ma'am. Yes, I hope to see you again. You make me feel a lot better and thank you Ma'am for that, I mean talking to me and treating me like a real person." "Oh, don't be silly Chelsea you are a very real person and we just need to find a place for you, so everyone sees that, goodbye now." Chelsea put baby doll Nancy back in her buggy and made the rounds. The next time she came to the buss stop Ms. Reynolds was gone. Chelsea found herself being somewhat disappointed. She was the nicest most understanding person she had met since her petticoating had begun some nine months earlier. Ms. Reynolds made Chelsea feel much better and even more important she convinced Chelsea there was hope. She was pretty unsure how it would be possible as Ms. Reynolds said, that she would begin to like being petticoated but still it was nice to think things would get better. As she passed Jessica's house on the last round she thought about Jessica and almost hoped she would be outside and see her...especially if the dreaded mean Cindy was not with her. But alas, is was not to be. As she entered the house Darla and Mother were waiting, like pouncing leopards, to hear all of the humiliating events that fell on Chelsea. They were surprised to see a somewhat calm and dignified look on Chelsea. Darla spoke first. "Well tell us what happened on your walk and do not leave anything out or else!" Chelsea smiled at them and said, "Oh sure, first let me put Baby doll Nancy in her crib and I will be right back and tell you everything." Mother and daughter looked at each other in totally disbelief as Chelsea trotted off to take care of the baby doll as if she were a real baby. They stood blinking their eyes at each other not know how to react or what to say. Chelsea soon returned and told them of her walk. Meeting up with Jessica and Cindy and what they said and then going to the bus stop and meeting Ms. Reynolds and finishing the walk. "You mean to say that this Ms. Reynolds you met thought it was appropriate for you to be dressed like a little girl taking your baby doll for a walk?" "No, I said she said she understood why you were doing it and that she had petticoated her late husband." "But she did not make fun of you at all? Not one time?" "No, she said a sissy boy like me if properly trained was an asset and that she had enjoyed her sissy husband and all that he did immensely." "And she was serious?" "Yes, I think she was very serios." "Are you sure she was not just saying these things to make you feel better?" "No mother, she was quite honest and direct with me. For example, she asked me how I thought I would do comparted to real men. 200-pound men who were manly and strong. She did not pretend I was something else she just did not mock what I am, there is a difference. And besides you will see when she gets in touch with you." "In touch with me? Why does she want to do that?" "I don't know but I think it may be to share some of her experiences since she petticoated her husband." Darla and Carrie just simply did not know what to think. But it did not take long to find out. They had just sent Chelsea to bed when the phone rang, and it was Ms. Reynolds! "Hi is this Carrie Williams?" "Yes, who I am speaking with please?" "Oh, Hi Carrie, this Sylvia Williams and I met your little sissy girl Chelsea today at the bus stop. She was giving a bottle to her baby doll...Nancy she called her." "Oh yes Chelsea just finished telling me and my daughter about meeting you." "Oh, good I wasn't sure if she would or not." "Yes, yes, she did, and she said you were quite nice to her. What is your interest in her?" "Straight to the point, I like that, very well. I would like to hire her as my maid two days a week if that is suitable to you. You see my late husband served as my sissy maid and I really could use another good maid around the house." "You want her to work as your maid?" Carrie had now put the phone on speaker phone, so Darla could hear the conversation as well. "Yes, I most certainly do, and I will train her, but I expect her to learn quickly and be efficient as my maid." "Will you want her to wear a dress for work, she is being petticoated you know?" "Yes, I know but I will provide her with maid's uniforms to wear. I expect my sissy maid to dress properly with an appropriate maids' uniform and to learn proper servant protocol, that is not up for negotiation." Darla and her mother looked at each other with raised eyebrows and then smiles. "So just so I understand this, she will be required to wear a regulation maid's uniform the entire time she is working for you and follow proper maids' protocol?" "Yes, that's exactly right, no exceptions." Carrie looked at her daughter as both of their smiles grew and then high fived each other in joy. "Oh, I suppose we can live with that," Carrie said as she and Darla tried to stifle their laughter and joy at the prospect of poor little Chelsea prancing around dressed as a maid and being totally subservient. "Very well, agreed then. When can I have her?" "When would you like her?" "Tuesdays and Thursdays and if I have any special events." "Special events?" asked Carrie. "Yes, dinner parties, luncheons, things like that. I will expect her to learn to be efficient at serving groups." Darla wanted to know, "And she will wear her maids' uniform then to. I mean while serving these groups?" "Most certainly though it will be a formal maids' uniform and not her everyday working maid's uniform that she will be expected to wear on a daily basis. Oh, and do you mind, is it ok if she wears her maids' uniform to and from work?" Carrie responded, "You mean you want her to change at home and wear her uniform to and from work?" The two ladies were ecstatic over this imagining the humiliation this would heap upon Chelsea and they were loving it. "Yes, that way she does not waste time changing here I am not one to allow a sissy to waste time. I never permitted my late husband to waste time and I am not going to start allowing it now." "We agree. Yes, she can wear them to and from work. We think that will be character building for her anyhow. What time do you want her, and does she know where you live?" "8:00 AM till 7:00 PM will her work hours with a ten-minute break at lunch. No, she does not know where I live so if you are ready I will give you my address." "Yes, please go ahead." "I am at 2628 Center street in the big yellow house. I will have her fitted the first day and she will have her uniforms on Thursday. I believe I am about 5 blocks from you, so I would prefer she walk to work. I don't believe in a sissy having a driver's license anyway. By the way, Chelsea said you have a seamstress that custom makes her little girl's party dresses. Do you think she might be available to alter some maids' uniforms to fit her? I think the sooner I can get her into a uniform the better." Carrie Williams was delighted and said, "I agree Sylvia, yes her name is Pam Stokes and her number is 555 1212. I hope to meet you soon in the meantime good luck with my so, I mean my daughter, ha, ha." Goodbye Ms. Williams and Darla and maybe one day soon you can attend an afternoon tea and see how your little girl is coming along." "Oh, that would be wonderful Ms. Reynolds," said Darla. "Oh Chelsea! Chelsea, Chelsea." Chelsea lept out of bed in her little pink nighty and hurried toward her mother fearing she was in serious trouble to be called from bed like this. Scared, the pansy said, "Yes Mother?" "I just spoke with Ms. Reynolds, you know the lady you met at the bus stop?" "Oh yes I know who she is, she called you?" "Yes, and she wants you to begin serving her as her maid two days a week starting tomorrow, and I have agreed." "Seriously?" "Yes Seriously, she is going to teach you to be a proper maid. She lives at 2628 Center street in the big yellow house, she said, and you are to be there before 8:00 AM. So, you will need to leave here by 7:15 Am as you will be walking and its about 5 blocks from here she thinks." "Yes mother." Both mother and sister were ecstatic over sissy boy Chelsea having to walk to and from work and then serve as a sissy maid. It just sounded like so much fun and humiliation. Chelsea was not too sure what to think. He believed Ms. Reynolds when she said she would help him but how was this helping him? Oh well, for now he was going to give her a chance before he condemned her. In the meantime, Ms. Reynolds was already on the phone to Pam and asking her if she might have a record of Chelsea's measurements for altering the maid's uniforms. "Yes of course I keep a record besides I know that both Carrie and Darla will want more pretty sissy dresses for Chelsea to wear. He is such a panty waist you know?" "Yes Pam, I do know, and I am beginning his maid training tomorrow. Do you think if I bring over some uniforms for you to adjust you could possibly get one done yet today, so he has it to wear in the morning?" "Well, normally I do not turn things around that fast, but I will make an exception this one time for you because I know how much better it would be or Chelsea to be wearing a maid's uniform when she starts her training. Yes, I think I could have it done in an hour after I get it." "Oh, that's wonderful Pam, I really do appreciate it. I will be right over." Sylvia dropped off 3 working maids dresses and two formal maids' dresses and asked that Pam do one of the working maid dresses right away. She left and came back in an hour. Her work was exquisite. Sylvia was quite pleased. At 6:15 Chelsea rose and took her bath and got ready. She thought a great deal about what might happen at Ms. Reynolds. She was almost sure the lady was going to be kind and helpful but there was an ounce or more of doubt placed in her little brain by her mother and sister. She thought about it all the way to work. When she saw the big yellow house, she suddenly got butterflies in her stomach and her doubts increased with each step forward. As the door started to open she thought she would surely faint but as she saw the smile on Ms. Reynolds face her worries melted away. "Well good morning Chelsea, don't you look pretty this morning. I trust you had an enjoyable walk? Please do come in." "Good morning Ms. Reynolds, Yes my walk was pleasant and uneventful." Sylvia led Chelsea to the kitchen where she invited the sissy to sit and she sat as well. "Well Chelsea, I suppose your mother told you I want you to work for me as my maid two days a week, Tuesdays and Thursdays and then serve parties or teas or whatever when needed?" "Yes, she did tell me and her and Darla both acted like it was a prison sentence for me..." "Oh, it will be no such thing. I told you I would try to help you, and this is how I figured I could do it. This will get you out of the house at least two days a week where you can be more appreciated. And I will just bet you will love being my maid, my late sissy husband sure did, he loved being my maid. He said it was so rewarding and made him feel so good that he just loved it!" "He did? But doesn't a maid have really hard drudgery and all?" "Oh, you watch to many movies. Being a sissy maid is an honor, you'll see ,you will quickly love it." Chelsea was buying the story and smiling and hoping Ms. Reynolds was right! "Now listen Chelsea, there will be rules and punishments delivered when they are not followed. But they will be fair, and they will be for your own good. But you will also get to have fun and feel good about yourself while earing respect. "Respect? How in the world could a prissy pansy like me earn respect? Who would ever give a sissy respect?" "You will see my dear, you just obey me and do your best and you will see who will give you respect. In fact, I will tell you right now four who will but there will be more rest assured. The four I will name right now are me, your mother and sister and Jennifer." "Jennifer? How? Why? I mean..." "Just you never mind just mind me and know they all will. Ok come with me I have a surprise for you." Chelsea got up and followed Ms. Reynolds down a hall to a bed room on the left. "This will be your room Chelsea. This is where you will rest, change, prepare or spend time if I send you to your room. It is your responsibility ty to keep perfectly clean and organized, are we clear?" "Yes Ma'am." Sylvia opened up the closet and there hanging all alone was a simple Black dress with white trim. On the floor under was a pair of Black opened toed 4" spike heels. Chelsea looked and wondered what this was all about. "I have taken additional uniforms to Pam Stokes to alter. You know her she made your pretty little girl's party dresses and she will have them done over the next few days. But for now, this is your one uniform altered to properly fit you. Please take off your dress and when you do please hang it next to the maid's uniform." Chelsea took off her dress and her shoes and put them in the closet and carefully with wonderment took out the maids uniform hanging and laid it on the bed. She noticed it had multiple pieces. The dress, a cap, a collar and an apron. "A maid is uniformed according to her position and time of day. There are various positions for maids like : Lady's Maid: The lady's maid is normally the senior-most maid in the household who reported directly to the lady of the house and represented the other maids under employment. Her duties included maintaining the wardrobe and accessories of the household lady. Lady's maids are also generally expert needlewomen and hairdressers. Though the job could be challenging sometimes, they enjoyed a higher social status than the other servants and earned more money. Chambermaids: Chambermaids perform a number of duties which included typical domestic chores such as cooking, ironing, washing, cleaning the house, grocery shopping, taking care of household pets and children etc. Parlor Maid: The main function of the parlor maid is to take care of the parlor, or reception room and the table, and to answer and welcome the door. Nursery Maid: The nursery maid reports to the nanny or the children's nurse and her main duties included chores related to the cleaning and maintaining of the nursery. She is also to assist the nurse in other chores when needed. Kitchen Maid: The kitchen maid reports to the Head Cook and ranks below the cook in the household help hierarchy. She could also become the assistant cook depending on experience and expertise. Scullery Maid: As an assistant to the kitchen maid, the scullery maid is the lowest ranking maid in the household. Her duties included cleaning of the floor, stoves, sinks, pots and dishes. They are more commonly known as "Hall Girls" in the United States. Of course, my household is not large enough to require a "girl" for each position, so you will learn to perform all the duties and be able to identify the duties of each position and how you should dress. Your first uniform, the one lying on the bed is a basic plain uniform. You will have several more uniforms in a few days. Most days you will wear two different uniforms but, on some days, you will wear three different ones. I will expect you to always be in the proper uniform for the occasion." "It seems like and awful lot to know!" "Don't worry sweetie I will help you learn it. I want you to succeed." Chelsea smiled at Ms. Reynolds. Sylvia smiled back. "Ok let's get you into this uniform." Chelsea looked almost anxious to put on the uniform. This was not normal for her to want to do something like this. Sylvia helped her with it and soon she had it all on including the shoes. The dress fit perfectly since Pam had altered it. She looked very cute and subservient in the uniform. "My, that fits you perfect, Pam is a great seamstress. How do you like it?" Chelsea stood in front of the three-sided mirror looking and feeling. "I like it Ms. Reynolds, it makes me look...ah proper somehow." "Yes, I believe you are right, proper is a great description. Ok let's get you started doing some basic maid's duties." For the rest of the morning Sylvia had Chelsea cleaning bathrooms and the kitchen. Chelsea never knew that there were so many places that really required cleaning. She doubted that even her mother knew of or cleaned those areas. Even though the work was hard it was not difficult and for some reason it went very fast and it was sort of fun. Especially when Chelsea finished a room and stood back and looked it all over. It felt so rewarding. Each time Chelsea did a good job and finished a task, Sylvia would comment, "Good girl, you are going to make a perfect sissy maid." That was what Chelsea liked best about Ms. Reynolds. She was honest and fair. She did not pretend she was not sissifying Chelsea, in fact she sort of emphasized that she was doing just that to the pansy. But she complimented him often on his work, direction, position and all. She made it all positive. Never mocking him. At noon, Sylvia used her skills to guide Chelsea to make a perfect ladies' lunch and serve it. She taught Chelsea to serve the lunch and then remove herself directly from the table area. To be standing nearby with head hung down standing against the wall, hands folded on apron and waiting for a command and returning after each command was completed to her position at the wall. Chelsea was a good student and Ms. Reynolds made that known to Chelsea. Chelsea responded with a big but quickly retracted smile acknowledging to Ms. Reynolds that it meant a great deal to Chelsea to receive compliments. It reminded her of her late husband who also tried not to show it but appreciated a compliment tremendously. In fact, Sylvia had learned early on that often a compliment to a sissy was the best encouragement there was. They simply seemed to thrive on it and seek them out and in so doing did a better job of serving their mistress. Ms. Reynolds was a very intelligent woman who wanted the most out of a male which meant turning them into a sissy servant. A maid skilled at doing all the mundane and ordinary work that required physical talents rather than mental ones. She recognized early on in her marriage that males were not exceptionally bright nor capable of figuring things out like an intelligent woman was. This helped her to push her late husband in a direction that benefited both and created a very long and happy marriage. She was in charge and there was no mistake about it. The sisification served to remind Herbert, her late husband, of that very thing. He was certainly unable to establish himself as the "Man" of the house while wearing 6" heels a tightly laced corset, silk panties and a fancy formal French Maids uniform. Who would take him seriously as the "Man" of the house? However, mentally challenged Herbert was, he was perfectly capable and good at obeying and serving his wife. In understanding she would do the thinking...for both...and then to follow her leadership. He had in fact become a very competent and capable sissy maid of which Both Ms. Reynolds and her pansy husband had taken great pride in. What pleased Sylvia was the way Herbert seemed to thoroughly enjoy her domination, leadership and being able to serve her. What pleased her pantie waist husband most was when guests complimented Ms. Sylvia on her sissy maid. If it were not for a very unfortunate car accident her prissy sissy husband would still be prancing around her home in 6" heels and short sissy maid's uniforms. Chelsea was a God-send in this regard. She was such a tiny sissy boy with no hint of real masculinity even if she had been allowed to wear trousers, men's shoes and shirts. The pathetic excuse for a man would have still presented himself as a very feminine male. So, what his mother and sister had done, even if in a sort of cruel fashion, was what Chelsea needed and Sylvia could see that. She had often wondered what it would have been like if Herbert had been raised properly, as a sissy by a domineering mother from a young age. Now she was going to find out with Chelsea. The day seemed to fly past very fast for both Sylvia and Chelsea, it was a pleasure for both of them. Chelsea's mind was awhirl with all that she had learned this day. Cleaning, making proper lunches, serving. It was all so interesting and rewarding, especially the smiles, head nods and compliments Ms. Reynolds had given her. She made it so enjoyable to be her sissy maid, Chelsea was on cloud nine and felt better about her self than she ever had in her whole life! Sylvia also had a wonderful day, the best since losing her husband over a year ago. It was such a pleasure to see a young man so determined to be a proper sissy maid and give up all that masculine nonsense and embrace the world of femininity. "Chelsea, come here please." Chelsea hurried to Ms. Sylvia and curtsied her arrival. "You have such a lovely curtsy my dear, would you please give me another, I love to see you do them?" Chelsea tried to hide her smile and gave Ms. Reynolds another curtsy. It was true she did curtsy quite well and was grateful for both mother and Darla for teaching her and making her practice, though at the time, doing 100 at a time seemed a bit much. But right now, receiving such a compliment and request seemed to make it all worth it. As Chelsea gave Ms. Reynolds her second curtsy she could not help but smile her pride. "You know Chelsea, you are such a good little sissy. Your curtsy is perfect, you are obedient and respectful. I want you to know its my pleasure to have you as my maid and I intend to show you off as soon as possible." If Chelsea's smile had gotten any bigger it would have required to faces to display it! "Really Ms. Sylvia, that is so nice of you to say, I...well, I really enjoyed working and learning from you today, you are so smart about this kind of stuff and I well just want to say thank you very much." "Let me tell you a secret Chelsea, A teacher always looks better with a great student. Now tell me, isn't it a lot more fun being a little pantie waist sissy than trying to be a real man?" Chelsea found the words conflicting. No male wants to be identified as a pantie waist or a sissy but somehow these words seemed positive coming from Ms. Sylvia. She thought it over and said, "Yes Ma'am, I really do love being a pantie waist and sissy and serving you Ma'am." "Very good young lady now let me see one more curtsy before I send you home." Chelsea smiled a huge smile and performed her third curtsy of the session. Sylvia clapped this time and expressed a huge smile of her own. "Ok, little girl, go get changed and you can head home." "Ma'am excuse me but do I have to change?" "What do you mean?" "I was wondering if I could wear my uniform home and show my mother and sister that I am a real maid now." Sylvia turned it over in her mind. "Well I wasn't going to have you do that until we received the other uniforms back form the seamstress. But you know what Chelsea, I think you have earned the right to wear your maids' uniform home. I know you will take good care of it and Yes, you may that is a wonderful idea. You will need to wash it and have it on when you report for work Thursday and Thursday is going to be a very exciting day for you. If you do as well as I think you will I am going to hold a luncheon on Saturday and you will be serving in a formal French Maids uniform. Won't that be fun?" Chelsea was already a robot for Ms. Reynolds and without even thinking agreed that it would be fun. His mind told him it would be fun but there was this little voice that said, "You are a guy and you will be all made up as a girl wearing some frilly fancy dress serving women as your superiors." But there was a second voice that said, "Yes, I know, and I want to do it!" Sylvia had already developed an ulterior motive sending Chelsea home in her sissy maid's uniform. Jessica! As Chelsea went out the door Sylvia quickly called Jessica. She had planned to invite the girl to her luncheon, but this was even better. "Hello is this Jessica?" "Yes, yes, it is." "Jessica this is Sylvia Reynolds and we have a mutual acquaintance that I am calling about...Chelsea." "Chelsea? Is he, I mean she ok?" Sylvia loved hearing the concern in Jessica's voice this confirmed she had feelings for the pansy. "Oh, she is fine, wonderful in fact. Listen Jessica, I think you care about Chelsea like I do, and I wanted to see if you would help me help her?" "You are right Ms. Reynolds I do care about Chelsea even if others make fun of her. I think she is a very sweet and good person". "She is all of that and more Jessica. She started working for me as my maid today. She will work two days a week and for special occasions. She has really come out of her shell and loves being a sissy maid. I don't have much time right now because Chelsea is walking home and will go right by your place. She is wearing her maids' uniform and loves it. She asked if she could wear it home and show her mother and sister that she was a real maid now!" "Really? That's amazing since she is a really a boy, what do you think triggered that?" "I don't have the time right now to explain it all, but my late husband was my sissy maid. Once they get past their silly macho nonsense and embrace the feminine they truly become proud to be sissies and especially sissy maids." "I see, amazing and interesting. So, you're saying Chelsea can actually like and want to be a sissy maid servant and be controlled by a woman all the time?" "Yes, and much, much, more but I want to ask a favor." "Sorry It's just that I find this so interesting." "Ok we can talk latter in as much detail as you want. I love the subject but if you could please intercept Chelsea on her way home and do it like it was an accident and praise her about her new job and uniform in a way that she does not know we talked. I want her to feel really good about her day, her position, her uniform and especially about you Jessica." "Oh, ok I can do that. I'll call you after were done...if that's Ok?" "Yes, I wish you would, bye." Jessica watched for Chelsea to appear heading towards her house. Her house was hers now. Her father had been transferred out of state the last half of high school and so her parents allowed her to take over the house. She had a great job and was buying it from her parents. When she saw Chelsea walking her way she timed it to run into her on the sidewalk. "Oh, hi Chelsea, how are you today?" Chelsea brightened right up to see Jessica especially because Cindy was not with her. "Hi Jessica, I am very good how about you?" "I am fine Chelsea thank you. Where are you coming from?" Chelsea was so happy to run into Jessica. "Oh, I have a job now. I work for a lady named Ms. Sylvia Reynolds, she is wonderful to work for." "Is THAT a real maid's uniform you are wearing?" Jessica said with all the admiration she could muster. Chelsea beamed with pride, "Yes, it is I am a real maid now and while I still have a great deal to learn Ms. Reynolds said I am an excellent maid and she even trusted me to wear my uniform home. Oh, and I actually have a lot of maid's uniforms. Ms. Stokes is altering them right now. Some are even fancy formal French Maid's uniforms and I am going to get to wear one on Saturday." It was obvious to Jessica that Chelsea was extremely excited, she had never seen the pantie waist boy she went to high school with so excited before. It was fun to watch. "Would you like to come in for a few moments Chelsea?" "Chelsea almost swallowed her tongue. Jessica was actually inviting her into her house?" She almost could not answer. "Y, ye, yes I would, thank you Jessica." As they went into the house Chelsea walked like she was entering a castle. Looking careful around as she entered the mysterious den of the beautiful princess Jessica! "Let me look at you, I love your uniform its so proper looking. It fits perfectly doesn't it?" "Yes Ms. Stokes is a very good seamstress. She's the one who makes my..." "Your?" Chelsea got very embarrassed, "my little girl's party dresses." Chelsea's face turned down and she got quiet. "Now Chelsea you need not be embarrassed because your sister and mother make you parade around in little girl's party dresses. I know you get embarrassed over them, but they really are cute, and I do so love to see you in them. They make you look so juvenile and sissyish it's just so cute, it sort of turns me on. But listen this maid's uniform makes you look entirely different. So proper and professional. I like the look, well honestly I like both looks." "Jessica?" "Yes Chelsea." "Why do you like me to look like a little girl, you know I am not one." "No, you are not really a little girl Chelsea but that's what makes it so cute. You are entirely out of character. You have surrendered your manhood and subjugated yourself completely. It's a very vulnerable look and it makes me feel good to see you with that look, acknowledging you're not a real man and you accept it. That takes strength that real men don't possess." "Really you think it makes me stronger than a real man?" "In some ways Chelsea, in ways that appeal to a woman like me." "So, you don't want to make fun of me or put me down like Cindy does?" "Oh, don't pay any attention to Cindy, I think she is threatened by you, you are actually prettier and sexier than she is and that bothers her. Besides she doesn't like anyone who takes my attention." "I take your attention?" "Well...you know what I mean...well I guess I should be honest with you, you are so honest with everyone. Yes, you do take my attention, I talk a lot about you to who ever will listen. I find you fascinating. I don't say I completely understand but I do like you Chelsea and I enjoy talking to you and seeing you and even thinking about you especially when I am alone at night I ... Well never mind. Tell me about your new job. That's what I want to hear about." Chelsea was totally thrilled to know Jessica cared about her. She told Jessica all about her day and what she did and learned and even about Ms. Reynolds wanting her to curtsy three times. Jessica had seen Chelsea curtsy before and she recalled it was a very sexy thing so she asked her to curtsy for her. Chelsea was pleased to do so and performed an excellent curtsy for Jessica. Jessica was amazed, the image of this prissy sissy boy curtsying to her triggered a feeling inside her that Jessica had never felt. It was one of domination one where she began to think she needed to own and control this little pansy. It made her wet, she asked Chelsea to curtsy again and say, "Yes Ms. Jessica," as she did it. Silly Chelsea not recognizing what was going on did three more curtsy's and said, "Yes Ms. Jessica," as she did each of them. Jessica actually had a climax watching the pantie waist subjugate himself to her! She recognized that Chelsea was clueless to what had happened so did not mention it. "Listen Chelsea, you work for Ms. Reynolds on Tuesdays and Wednesdays, right?" "Yes Ms. Jessica." "Ok then I want you to work for me on Mondays and Fridays. Is it a deal? "Will I be wearing a maid's uniform?" "Yes, you most certainly will young lady or anything else I tell you to wear!" "Ok, I will, I will work for you to." Chelsea was truly clueless to what was going on. He saw it simply as a fun thing and way to spend more time around Jessica. "I am very proud of you Chelsea and I love your uniform, maybe you and I will go uniform shopping together, would you like that?" Chelsea would love to spend any time she could with Jessica so naturally she told Jessica she would. "Ok let's go tomorrow and buy you some uniforms. I have off tomorrow, so it will work perfectly. You better get on home now before your mother sends out a search party. Oh, and I want to see a curtsy before you leave young lady and don't forget the "Yes Ms. Jessica."" Chelsea smiled and did as told leaving feeling really great about himself. He hurried home and soon after entering the house both his mother and sister appeared and began to look him over. "Well," asked his mother? "Oh, it was amazing mother. I learned so much about being a sissy maid today. And I like working for Ms. Reynolds." "Did she give you that uniform?" "Yes, and she told me I could wear it home today to show you and Darla. Do you like it?" "Let's see, turn for us." Chelsea turned, and the ladies examined him carefully. Darla spoke up, "I'd say it's perfect for you, it certainly makes you look more like a servant." Darla meant it as a rub, but Chelsea took it as a compliment and said, "Thank you Darla that was nice of you to say that." Darla raised her eyebrows and looked over at her mother in wonderment. What had happened to her little sissy brother in the past day to change his attitude like this? He would have had tears in his eyes before, causing his mascara to run but now he just smiled and thanked her. Had Ms. Reynolds put him under some spell? "Oh mother, Darla, I want to thank you both for making me practice my curtsies so much. I admit I hated it at the time, but it really paid off Ms. Reynolds loved them and So did Jessica." The two women looked at Chelsea and then each other in total shock. Did they just hear him right? Did he actually thank them for making him practice taking hold of his petticoat punishment skirt and dip properly with it? Did he say that both Ms. Reynolds and Jessica loved seeing him curtsey and he took pride in sharing that? "Jessica? How did she get into this conversation?" "Oh, I ran into her on the way home and she loved my new uniform and I am also going to be working for her as her maid two days a week and she loved my curtsey too so again thank you for making me practice them so much the practice has really paid off! If it's ok with you mother, I would like to scrub the kitchen floor now it looks as if it needs it!" Carrie and Darla Williams did not know what to say other than "Sure, ya go ahead." They were confused and amazed. How could so much happen in just one day. Carrie decided she was going to call Ms. Reynolds and find out. The line was busy. Sylvia was already on the phone with Jessica who was sharing what happened when Chelsea stopped by. "Ms. Reynolds, I don't know if this is improper to share but I just have to know what you think. I actually had a climax watching Chelsea curtsy. I don't know why I found it so sexy, but I most certainly did." Ms. Reynolds giggled. "Its normal dear. I used to climax every time I watched my late sissy maid husband on his hands and knees scrubbing the floor. Its part of why I loved owning a sissy maid husband. I will share a secret with you my dear. Sometimes when I was going out on a date I would have my husband scrub the kitchen floor as I was leaving. It made the date a little more interesting f you know what I mean, giggle, giggle." "Oh Ms. Reynolds you are wicked, ha, ha, ha." The two talked for quite some time and shared a good deal of information. Sylvia confirmed with Jessica about the luncheon for Saturday at noon and both were excited to think of Chelsea serving her first formal luncheon in a French formal French maids' uniform. "And 6" heels" remarked Sylvia. "He will be teetering but it will help focus his mind on his sissyness. Now dear one more thing, I know you have needs but you must remember that Chelsea cannot in any way be permitted to function as a man especially when it comes to sex. So, you will need to find real men for those needs but that does not mean you cant use him as a sexual servant. There are face dildos. Oral service and you can always peg him." "Peg him? What is that?" "Pegging? That's where you take on the role of a man and treat him like a woman. You wear a strap on cock and fuck him Dear, it's very empowering." "Really? I never knew..." "Go on line and do a search for "Pegging", you will see and its really becoming quite common in Female Led Relationships. It certainly keeps them in their place." "Do they enjoy it at all?" "Oh my, do they, they become addicted to it They have climaxes like we do, long and deep and much better than the ones they typically enjoy. Yes, dear it turns out to be good for all, you have more and better control and they become even more subservient and subjugated to you." "Sounds interesting, I may have to try it." "Just learn how to do it right and be gentle in the beginning so he learns to love it right off." "I am so glad I met you Sylvia, I can't wait to meet you in person Saturday." "I'm looking forward to it as well." "You really think Chelsea is ready to serve a group of ladies as a sissy maid?" "Yes, she is ready and she will be even readier. She will be nervous of course but I think she will find it very rewarding and feel really good about herself after the luncheon."