All For Five Thousand Dollars free porn video

All for Five Thousand Dollars By Sissie Maid Cuckold When I read the "help wanted" ad I was not sure I would qualify. The ad read, "Wanted self-reliant office worker who can and will follow orders without question or hesitation. Who is skilled in all office practices and who understands the boss is the boss." I sent an e-mail with my resume attached and waited for a response. Two days later I received a very detailed application that I was to fill out and return as soon as possible. It asked many personal questions and contained a disclaimer saying that it was NOT necessary to answer any of the questions asked but that it did help to evaluate a candidate at a distance. I lived In NY City and the job was 2200 miles away. I felt it best to answer them all and hoped that so doing showed my interest in obtaining the position. A few days later I received another email asking for a copy of my driver's license and four good clear photos of myself. I again did as requested and hoped that doing so would help. I heard that evening by phone from a MS. Jamison. She told me she was the owner of the company and had reviewed my application and answers and wanted to now do a phone interview to determine if I should be flown in for a personal interview. She asked the normal questions and then a few that I had not been asked before. "Mr. Allen, how do you feel about working for a woman boss?" "I have no adverse issues with working for a female boss Ma'am." "Good because that is important here." "I noticed in your photos that you have fairly long hair, do you always wear it that way?" "I have worn it that way for the past several years but if it is a problem Ma'am I can cut it short." "I did not say it was a problem and it is not a problem. It shows pride in yourself by having nice hair and keeping it nice I commend you on it and I am glad you have had it that way for some time." "Do you have the means to fly here for an interview?" "Ahh No Ma'am I don't at the moment." "Ok that's Ok, I think you are worth a chance on so I'll tell you what I'll do. I'll pay for your ticket and room, meals and transportation for the interview. If I don't hire you, you have no obligation to pay me back. But if I do you will agree to work for me for two years so I can recoup my time and expense. Will that work for you?" "Yes Ma'am, that's very generous of you. Thank you Ma'am." I left two days later for my interview. She had reserved a car for me at the airport and room close to her business. I drove by Jamison Industries before going to my room to see what it looked like. The building was fairly new and the landscaping immaculate. It made me a bit nervous when I saw how high class everything was but I reasoned she would not have made the deal she did with me if I did not have a good chance of winning the position. I did not sleep well that night and was early for my 9:00 A.M. meeting. Her receptionist had me take a seat and I felt that she kept looking at me strangely. The receptionist was good looking and quite tall about six foot one in her 3 inch heels. I was fascinated by her as well so did not know if it was just me or because I was staring at her. Soon her phone buzzed and she acknowledged that Ms. Jamison was ready to see me. I entered a very plush office. The kind that makes you want to put on cleaner clothes just so there is no chance you might smudge something. I shook her hand and noticed she had a strong grip for a woman. She smiled at me and then said, "Well, Mr. Allen, your hair is even prettier in real life." I blushed and thanked her, then took my seat. I could tell she was still looking at my hair and it made me feel a little strange. I had it back in a pony tail and was quite taken off guard when her first question was, "Mr. Allen would you let your hair down for me please, just take it out of the pony tail so I can see it better. I think it's marvelous that you have hair so pretty and well taken care of and I just want to have a better appreciation of it." Not fully understanding what her fascination with my hair was about I felt it much better to comply with my potential employers wishes than to piss her off and loose the interview so I complied. "My, it is just marvelous, I must really commend you on your hair Mr. Allen and I apologize for my fascination but I have to confess that I have always had a weakness for men with long hair especially those who take care of it properly, I hope you don't mind and thank you for indulging my fascination." "Yes Ma'am, it's no problem Ma'am," I replied to her. She then proceeded with the interview and told me that I had the job if I wanted it and since I was short on funds she would advance me a month's wages which I could work off at her home after hours so it did not strap me financially. She told me I would be working in the office filling, typing, sorting and doing other office work. She also informed me that the office manager was a Ms. Simpson and I should check in with her in the morning. Then as I was getting ready to leave she said, "I would recommend you wear your hair down while you're working rather than in a pony tail, I think it much more becoming." Other places I worked had the opposite feelings. They were Ok with my hair as long as it was in a pony tail so I found this nice as I did like to wear it down better than back. I reported to work the next morning and saw Ms. Simpson. She gave me my orders which I found easy to follow. It was a short week and when Friday came I was summoned into Ms. Jamison's office. She asked, "Are you ready to begin paying back your debt to me?" I told her I was and she said she was glad to hear it. She gave me her address and told me to be there at 8:00 AM. I arrived at a very beautiful home and was greeted at the door by the office receptionist but she was not dressed in a business skirt and blouse as she was before but rather in a French Maids uniform. She turned a bit red upon seeing me which I found odd at the time. She then led me into Ms. Jamison's study where Ms. Jamison dismissed "Patsy" The maid and receptionist. She asked me, "Is there any work you are averse to performing in paying back your debt?" "No ma'am," was my quick reply. "Good then I shall put you to work momentarily but first I want you to understand that you will also incur some expense while you are working here. Your meals and uniforms and other supplies will be charged to you before the balance is applied to what you owe me, is that clear?" "Yes ma'am." She then picked up a hand bell and rang it. Patsy returned and gave her a little curtsey and said, "Yes ma'am you rang?" "Yes Patsy, take Mr. Allen here and provide the necessary items he will need to scrub and clean the kitchen. Mr. Allen is going to be repaying a debt he has to me and will be working weekends, at least, until it is repaid." "Yes Ma'am, right away Ma'am," came Patsy's reply. Patsy provided me with all of the cleaning supplies I would need along with a pair of pink rubber gloves and matching pink shoe covers and an apron also pink. She told me to turn around and she would help me with the apron. I hesitated and asked why I needed an apron. She said, nearly in a whisper, "Because Ms. Simpson says you do and if you know what's good for you, you will NOT challenge her orders or expectations. I tried that once and believe me when I tell you not to try it." "But, what do you mean, tell me what you mean?" "Well let's just say that the reason I work weekends and have to wear a corset and French Maids uniform is because I was foolish enough to argue with her over a very minor matter that would have meant nothing had I left it alone. Now if you know what's good for you and me you will do as you are told. She did ask you if you could follow orders before she hired you didn't she?" "Yes." "Ok then follow them." I felt ridiculous but did as Patsy said to do and wondered what the heck the deal was. I cleaned until noon and was then permitted a short lunch break and back to work. It's amazing how much work there is in cleaning a kitchen thoroughly. About 3:00 P.M. Patsy came and told me to report to Ms. Jamison. When I did she smiled at how I looked and said, "You look very nice in pink, not every male can carry it as well as you do." "Yes Ma'am thank you Ma'am." "I want to measure you for your uniform. As you can see from Patsy I prefer my people to be in uniform I believe it gives them pride, a sense of belonging and keeps their minds concentrated on their work. By the way you seem to have a knack for cleaning." Again I thanked her. She seemed to measure everything but my inseam. When I asked her about taking an inseam measurement she said, "Oh that's not necessary they will be fine with the other measurements I took," and I was then dismissed to go back to work. The next day I was put about cleaning bedrooms, six in all and one which seemed to be Patsy's as it had nearly a dozen maid's uniforms in the closet. The week passed quickly and again I was told to report to Ms. Simpson's home on Saturday AM. Ms. Simpson was her bubbly self as usual and told me that my uniforms had arrived and from this point forward I was to shower after arriving and change into my uniform and work the day. She said that I would stay on Saturday nights and work Sunday before leaving. Patsy would be available to assist me in whatever help I needed." I was then escorted to the shower by Patsy and my uniform in a garment bag was hung on the doors hook. Patsy left and I got in the shower. After a quick shower I dried and then opened the garment bag to find a working maids uniform. I thought it must be a joke and looked around for my clothes but could not find them. Apparently someone had entered the bathroom while I was showering and removed them. I squeezed open the door and called for patsy. After calling and waiting for some time Patsy finally appeared and asked what the problem was. I explained and she looked at me like I was nuts. She said, "Ms. Jamison has assigned you to do maids work hasn't she?" "Well yes but I am not a maid and I am certainly not a girl." "Well if you do maids work I think that qualifies you as a maid and as far as I know being a girl is not a prerequisite to wearing a females uniform." "But I can't wear girl's clothes." "Why not?" "Because I am a man that's why, what's wrong with you is this some kind of a joke or something. Get Ms. Simpson and tell her I want my boy clothes back and want to talk to her." "If you are absolutely sure that's what you want that's what I'll do but I would recommend you reconsider that request as I don't think she is going to be very happy with you for disobeying her wishes." "Yes it is what I want you to do, this is ridiculous and I am going to put an end to it right now!" Patsy shook her head and left. Soon I heard a disgruntled Ms. Simpson coming down the hall chastising Patsy as she came. I had not seen this side of Ms. Simpson before and I became fearful. When she got to the bathroom door, she called my name and asked, "Is there something wrong with the uniform? Doesn't it fit?" "Well I don't know if it fits or not I did not try it on it's a girl maids uniform, Ma'am and I am a man." "You're kidding me; they gave you a Girl Maids Uniform?" "Yes Ma'am." "Let me see it," and she pushed the door open and took hold of it. She turned it and felt it and examined it all the time shaking her head and saying, "Oh My, Oh My." Then she looked at me and said in a very stern voice accompanied by glaring eyes, "WELL OF COURSE IT'S A GIRL MAIDS UNIFORM WHAT OTHER KIND DO THEY MAKE? I asked you if you had any aversions to any work and you said no. I told you that uniforms were to match the work being performed and you said you understood that, NOW put it on and get to work, Patsy you assist and if you both aren't working again under 20 minutes there will be hell to pay." She then stormed out and back down the hall talking to herself. Her demeanor was frightful and I was literally shaking as she left and I tried to figure out how to get the items on. I mean there were things there I had no idea what to do with them. Patsy was all upset as well and was mumbling something about how she would never get Ms. Simpson paid back at this rate. I needed extra help with the corset and putting on my nylons. I could not even figure out how to put the padded bra on by myself and my frustrations were felt by Patsy who said, "Just do exactly as she says and nothing will happen to you." When I was nearly dressed I thanked her for helping me and told her I was glad she was there because I needed a girl to know how to put some of these things on. She stopped what she was doing and looked at me in shock. "You think I am a girl? I am NOT a girl I am a boy just like you and had to learn these things just like you are going to. You should have listened to me but no you had to do it your way. You're an idiot and now you have us both in trouble." "What do you mean you are a boy? You're not a boy; you're way to pretty to be a boy, stop joking like this." Patsy just looked at me with disgust and then turned around, bent over flipped up her skirt and petticoat and lowered her panties until I could see a little cockhead poking out from between her smooth legs. "Now do you believe me?" She asked. I was totally shocked and stammered and stuttered around until I got out, "But how, why?" Patsy calmed down and whispered, "Look I took the job same as you did owning Ms. Jamison money. I agreed just as you did to work it off. I was given a uniform just as you were and because it was "too much trouble' to take off my makeup and long nails and my waist was not being trained to be small enough and a dozen other reasons she transferred me to the receptionist position and told me I had to also dress accordingly for that as well. And to top it off all the things I need for both jobs are charged to me so I can never get her paid back. I have been here for three years and owe her more than when I started. The breast implants alone cost me $6,000.00. If I ever get to the point that my debt is going down I get new dresses or a full makeover at the beauty parlor and there goes my progress. It's like owing the company store; you just get deeper in debt each day. And if you ever cross her she has a room downstairs that is soundproof and one you better hope you never have to go to. I did once and that was enough for me." "You really have tits?" was the only stupid thing I could say. She gave me a disgusted look and said, "Yes I really have tits and they aren't as much fun as you think, or at least they are not as much fun as I thought they would be." Now I was fully dressed and standing there in my heels and maids uniform. It was not a fancy one like Patsy was wearing instead being a working uniform. It made me feel very weird, sort of soft and vulnerable. It was also kind of nice feeling. Patsy sensed my confusion because HE had gone through it himself. He looked at me and said, "Yes they do feel nice and as you wear them more and more you actually begin to like the feel and the look and not be able to resist them. It seems impossible right now but you get caught up in it and there seems to be no way to fight it." "So what you are saying is that Ms. Jamison is going to turn me into a girl too?" Patsy looked me in the eyes and said, "Well not really a girl, more of a sissy. All of your masculine traits and thoughts will be stripped away and replaced by feminine ones and you will no longer think of yourself as a man or act or like one but you're not a real girl either so you're sort of in between. We better get to work, we can talk more later." Patsy quickly left and I presented myself to Ms. Jamison to show her I had complied. Walking down the hall created strange sensations from the nylons, slip and even the bra and corset. I felt different' not like a man at all and more like I imagined a girl would feel. Ms. Jamison's' eyes grew wide as she say me. "My, my, that's much better. How do the clothes feel?" Caught off guard by her question I spoke what I was feeling rather than what I should be feeling and said, "They feel strange but nice." "Good I am happy you like them and they fit you well. You will enjoy your work much more now that you are properly uniformed and as time goes on you will look forward to the comfort you will know from wearing proper clothes. Now turn for me. Did Patsy assist you?" "Yes Ma'am, she I mean he I mean she did." "Oh so Patsy told you she was really a he and what I have done to her?" "Yes Ma'am." "And are you worried that is what is going to happen to you?" "Ah, I don't really know Ma'am, is it, are you going to turn me into a girl Ma'am." "Oh silly, I can't turn a boy into a girl I can only expose the girl that's in him so the boy part goes away and he transforms like a butterfly into a sissy." "Do you think I have that girl part in me, Ma'am?" "Yes I do Alice; I am going to call you Alice from now on. You are very much a sissy needing to be let out and allowed to fly around in pretty things." "Why do you say that, I am a man and I don't act like girl or a sissy?" Ms. Jamison smiled and said, "No? What about your beautiful hair? Real men don't have hair like yours only girls and sissies have hair like yours. I want you to understand something. You will really enjoy being made a sissy even though right now the thought may be scary or even repulsive; I promise you that you will enjoy the transformation. You have seen Patsy; don't you think she is beautiful?" "Well...Yes but." "No buts, is she being held against her will?" "No but." "No buts Alice, you see she enjoys her position and if you don't believe me or feel I am being honest with you let's make a deal. You do as I say for the next 30 days, no exceptions. You observe her and you note how you feel now and how you feel after the thirty days and if you think you're not a sissy and want out I will wipe the slate clean and give you five thousand dollars and send you on your way, what do you have to lose?" "That does sound fair I guess." "Ok then, you promise to obey me in every way for the next thirty days without exception and to observe Patsy and see if she is happy or not?" "Yes I will do that." "Good girl. Then I want you to get to work doing your housework, you are my maid and you are to act like my maid. Later we will work on your poise, actions and looks some more so you will feel more comfortable and confident in your new position, now get. Oh and by the way, you do look VERY lovely in your new clothes." It was so weird. I felt proud and complimented even though I was a boy being made to dress like a girl against my wishes. Her words hunted me because it seemed like Patsy was happy and she certainly was attractive. I actually heard myself saying, "I wouldn't mind being a girl if I looked like that." As I did the house work I found it was more enjoyable doing it dressed like a maid. I can't explain why but I just seemed to fly through it. I would notice from time to time the feel of my clothing and it was intriguing. Several guests arrived and left and I found myself studying them, or more specifically their clothes and actions. They were all women and most wore pants but a few wore skirts and those fascinated me the most. I tried to imagine what they had underneath out of sight and one woman had a skirt I quickly imagined how I would look in it. Like I said, it was weird! When Patsy walked by I watched her too. She seemed to move gracefully and it was difficult to imagine her as a boy. She had a very nice figure and her face and hands were so feminine. Even her walk had no boy ways to it. It did not seem like she was in distress or was against her transformation. It was all curious and I felt comfortable that spending 30 days doing as Ms. Jamison asked would be of some benefit to me after I left. I was pretty sure that I would be leaving after thirty days with $5,000 in my pocket and the slate whipped clean and I was also pretty sure that I could pull of her request for thirty days without too much sweat. After dinner Ms. Jamison had Patsy bring me to her vanity where she sat me down and begin to work on me. As she did my face she had Patsy do my nails. Patsy glued longer nails on my fingers and then shaped them before painting them with three coats of bright pink polish and two coats of clear. Ms. Jamison explained that this would help make them stronger and less prone to damage until I got used to them and could grow out my own. Ms. Jamison worked on my face applying a base and then mascara and eye liner. She put a light blue eye shadow on my eyelids and some blush on my cheeks. My lips were coated in a color that matched my finger nails and she explained, "Alice it is important that you stay color coordinated. You need to have matching panties and bra and your nails and makeup need to be matching or complimentary as well. We will also fit you with accessories that will be color coordinated. Now this is very important for you to be a proper sissy so do you understand this?" "Yes Ma'am, I do." "Ok then I want you to repeat after me." "To be a good sissy I must make sure my bra and panties match." I repeated her words saying, "To be a good sissy I must make sure my bra and panties match." Then she told me to say, "I will make sure my makeup and accessories are color coordinated with the rest of me." And I followed with, "I will make sure my makeup and accessories are color coordinated with the rest of me." "Very good Alice, now I want you to say that out loud each morning before you change out of your nightgown into your dress." Night gown? I had not heard this before but I guess it made sense she was going to go all the way and while it was a bit of a shock hearing that I would be wearing a nightgown, it sort of made sense so I did not question it. They worked on me for about a half hour and then had me turn and look into the mirror. I was shocked, amazed and intrigued. I looked pretty... like a girl! I looked pretty and I liked it. As I sat there staring Ms. Jamison said, "Well? Don't you look pretty? How do you like the new you?" Before I could really think I blurted out, "I like it; I do look pretty, don't I?" "Yes you do Alice, very pretty. What do you think about changing your hair color making it a little lighter?" "You mean dying my hair?" "Yes Alice I mean dying your hair. All the girls do that and I think changing your hair from light brown to blond would make you even prettier, so let's try it OK?" I don't know what overcame me. I must have been caught up in the whole thing because I agreed to it! They wasted no time in doing my hair. I sat in the chair and watched them in a mirror. I was fascinated by it, I don't really know why but I was. It was sort of nice I guess being attended by two beautiful women and being made to look so pretty. And besides it was only for a month and why not try it out. After a month it would all go back and I would have the $5,000 bucks to do whatever I wanted. When they were done I looked amazing. I could not even tell I was a man and I knew I was. They fussed over me and put a pink bow in my hair. My maid's uniform was replaced by a pretty dress and plain shoes were exchanged for open toed pumps and showed of my painted toe nails. I was HOT. I was afraid to admit it but I could not keep it in I admitted I liked it! They both complimented me on how I looked and tried to teach me how to walk more like a lady, well, that was going to take some time, that was for sure. But just the overall feeling was really special, I don't know how or why but it felt very comfortable and natural. It was like it had been missing from my life and I was filling in the void. I noticed when I sat I mimicked how women sit in a dress; it just seemed to come natural like the dress had control of what I did and how I did it. I felt special and nice and warm and relaxed. In my mind I had imagined that I would be very uncomfortable and embarrassed and anxious but it was not that way. "Boy a month of this was going to be easy," I thought to myself, this is not so bad and besides it would probably help me hit it off better with chicks knowing some of this stuff. After we had spent several hours fussing with me and me learning things Ms. Jamison said, "Ok girls we have had enough fun for one night it's time for you girls to go to bed. Go get changed, Patsy will help you Alice and then report back to me." Patsy led me to her bedroom and opened her dresser drawer that was full of silky pretty night gowns. She took out a pink set and said, "Here Alice, these will go good with your nails and you look good in pink." She got herself out a pastel yellow set. She then explained that I would wear the bra I had on and the corset along with the nylons under the panty and gown that she handed me. We changed in front of each other like two girls with no masculine hang-ups about it. She then helped me remove my makeup stating, "You don't wear your make up to bed because it will get all over the sheets and be a terrible mess on your face in the morning." She sensed my disappointment about having to remove it after only hours of applying it and said, "I know Alice, you don't want to take it off and I will say you look very pretty in your makeup but it's a must do." As she removed her makeup I noticed that she still had eye liner and lip liner on and so I asked her why she got to leave that on and I had to remove mine. She smiled and said, "Mine does not come off my eye and lip liner is permanent, it is tattooed on so it's there all the time. It saves me time and looks good, don't you think?" I was fascinated that there was such a thing as permanent makeup and for a second I wished I had some but instead told her that I did think it was nice and for sure looked great. Then I thought about asking her if she thought I could have it put on me but then I remembered I would only be doing this for a month so it was probably not worth it. We got ready and she said, "Let's go and present ourselves to Ms. Jamison." When we got there Patsy executed a curtsey and I thought I probably should to since she had so I tried one. Let me tell you they are not as easy as they look and mine was sort of disaster. This brought giggles from both of them but Ms. Jamison said, "never mind, I appreciate your attempt and tomorrow you can practice how to do a proper curtsey. Well you girls do look sexy tonight. Alice I want you to go to my vanity and get my hair brush and bring it here I have a special treat for you." I did as instructed and returned with her hair brush avoiding any more attempts at dipping a curtsey to her. She told me that she was very proud of how I had responded and impressed with my appearance so I was going to be allowed to brush her hair. She instructed me on how to do it and I stood behind her and brushed her hair for some 20 minutes before she was satisfied. I don't know how to exactly explain how this felt. I was standing there in a very short pink gown wearing a frilly pink panty under with nylons, bra and corset and a pair of fluffy pink slippers. She was fully clothed in a pants and blouse outfit reading as I brushed her hair. It made me feel like she was a Queen and I her maid servant. I felt very small but very privileged. It felt natural and proper, but at the same time confusing. Why did I seem to enjoy doing this being this way, was she right, was I really a sissy deep down inside? After I was done she told me and Patsy to go and get in to Patsy's bed together and go to sleep as morning would come all to fast. Patsy gave me a bit of a strange look at these orders but said nothing. When we got into Patsy's room it dawned on me why the look. There was only one bed and it was single bed! Suddenly I felt a bit uncomfortable and so did Patsy. I asked what we were to do and she said, "We will do what we were told to do it will be tight but we'll manage. We got in and of course were pressed against each other and when ever Patsy or I would move nylon or silk was rubbed against my body stimulating me. It was a very strange sensation. To be in bed with a man who looked like a beautiful woman and be dressed like a beautiful women myself. It sort of made two men being in bed like not being in bed and like it was two women in bed and yet they were men and I knew I was but Patsy was so girl like it was just soooo confusing. In the morning I was again dressed in my maid's uniform and put makeup on, actually mostly Patsy put my make up on but told me I had to learn to do it myself. After Ms. Jamison had her breakfast she informed Patsy and me that I would spend an hour on deportment and feminine movement before doing my house work and that after lunch and after dinner an hour would be spent doing the same thing. The first order of business was just as I had expected how to execute a proper curtsey. I learn pretty quickly and once I got my balance downright I was able to execute a pretty good curtsey. Ms. Jamison was so pleased with how fast I learned and how well I did that she told me I was going to get a reward. She sent Patsy of for "cuffs" and when Patsy returned she had a pair of leather wrist cuffs and a collar. I was told to turn around and Ms. Jamison took my wrists and pulled them behind me and fastened them together. She then placed the collar around my neck and secured it. This all was followed by the wrists cuffs being raised up and attached to my neck collar in a way that held my arms high behind my back. I was beginning to wonder how this was a reward when I heard Ms. Jamison say, "Ok Alice now lay across my lap." Starting to shake, I did as she asked really wondering what was going to happen when I felt her hand on the back of my thighs. She caressed my nylon clad legs and it felt oh so nice. Then she moved her hand up and rubbed my pantied bottom for a while which felt even better. Next she seemed to brush my petticoat and dress up over my hands and went back to rubbing my bottom. After a few moments of this I was told to spread my legs some which I did without hesitation, I mean it felt way to good and I did NOT want her to stop what she was doing. I had been taught when wearing panties to pull my penis back between my legs and give it a half twist. Patsy said that was the best way to wear panties and it seemed to make sense I didn't know why but it did so I did it. Ms. Jamison now located my penis head through my panties and began to gently caress it. Oh how wonderful that felt. It was exquisite! I felt absolutely wonderful and erotic. It went on for some time and I hoped it would never stop but I was getting more and more excited. I could feel my penis straining and I knew that some pre cum had leaked as Ms. Jamison told me, "Oh Alice you are creaming your panties just a like a real girl does when she is excited." She then began to ask me questions and stop periodically with the caressing. She began by asking, "You like the way this feels don't you? This is the best you have ever felt isn't it? These clothes feel wonderful and you love wearing make up? You don't want to stop wearing pretty sissy clothes do you? You want to wear makeup all the time and even get permanent make up so you can be as pretty as Patsy? Do you want to cum? Well dear you are a sissy girl now so you have to learn to cum like a sissy girl and this is not the way a sissy girl cums. If I teach you how to cum like a sissy girl will admit you want to be a sissy forever? Ok them tell me you want to and why and what you want to wear." "Oh God please yes I want to learn how to cum like a sissy girl and I want to be a sissy girl forever and I want to learn everything a sissy girl needs to know to be a good sissy girl and I want to wear makeup and pretty dresses and frilly panties and brush your hair and do whatever you want me to do, please I will do it please just let me cum." Ms. Jamison began to slow down with the tantalizing massage that she as giving me and told me that it would have to wait that I had not earned such a privilege yet. But that if I was a good girl and practiced being the best sissy I could possibly be it would happen. She then slowed even more and began to rub my bottom soon brushing my petticoat and skirts back over me. I was allowed to stand up but my hands were not released. She gave instructions to Patsy to remove them after 15 minutes. I stood there shaken and excited and defeated and obedient, I had no choice and the receding high of the sexual stimulation kept my mind focused on what Ms. Jamison had said "Be a good girl, be a good sissy." Patsy came over and unfastened my cuffs and my collar as instructed when the time had passed. I recall giving a long sigh and seeing Patsy coyly smile at me. She raised her eyebrows but said nothing I did the same, I guess we just knew and did not need to talk about it. I was sent back to doing maids work and after dinner had another session on feminine improvements. This time it was concentrated on walking and sitting. How to brush my skirt under me as I sat and then to sit with ankles crossed and hands folded in my lap up straight and to smile. Walking was more difficult for me I just didn't get it. I tried and I tried but neither Ms. Jamison nor Patsy seemed to be too pleased with my walk and frowned each time I made a pass. It was then that the bomb shell was dropped in my lap. Ms. Jamison informed me that I would be attending work in the morning as Alice and properly attired as young sissy should be. "What, I can't go to work dressed like a girl; I didn't have any idea that you would want me to do that. I thought it was just going to be here that I had to dress and act like a girl for a month not in public." I went on and on while Ms. Jamison just sat their calmly which began to unnerve me. I started to recall some of the things that Patsy had told me about arguing with her and the room down stairs that I did not want to visit. I remembered Patsy's breast implants and started to fear for my life. It was like an out of body experience I just began to melt and calm down I saw myself shrinking and getting smaller and smaller until I was the size of her big toe and then I heard myself agreeing to wear a dress to work in the morning and make sure my makeup was perfect. It was like a dream but it was real. She had not said a word, not one and she had made me bow down and do what she wanted. How did she do that? I thought as I heard this strange me agreeing to be her female employee with no force or pressure on her part. Suddenly all was quiet and I stood their head bowed hands folded on my skirt and feet together as I heard her tell Patsy, "Take are little angel to the bed room and pick out a very pretty dress for her to wear to work tomorrow. An be sure and get one of the special corsets out as well and dress her up, put her in 4 inch heels and let me see what we have." Patsy curtseyed to Ms. Jamison and said, "Yes Ma'am." And the two of us left to try on dresses. Patsy picked out a bright red dress with a full skirt pleated and just above my knees. She thought the pink petticoat would go well with it. It was dated to be sure and certainly not the kind of dress that any real woman would be caught dead wearing especially in the work place but that was the point as I learned later. I was not to be a real woman I was to be a sissy, a feminized male subject to be ridiculed and mocked at every turn especially if I did not toe the line. My tantrum was not unnoticed it was not forgotten it was dealt with in a cool calm collected manner designed to show me her power and make sure I never forgot who she was and what my position to her was. But I knew none of this at the time. I was not into women's fashions so it was all Greek to me. The special corset was quite restrictive and along with its wasp waist had a posture collar. As patsy laced me into it she asked, "Did you really mean all the things you said?" "You mean when I was telling her I was not going to be a girl?" "No I mean when she had you over her lap and was massaging you, did you really mean you wanted to be a sissy girl?" "Who Me? No, not a chance I am just doing this for the money." "Really, said Patsy, because you sure made it sound real to me." "I hesitated and said, "Did it really? Good I had her fooled then." "I doubt you fooled her. She did that same thing to me you know and I said similar things and afterward I pretended that I hated it too but really I didn't and maybe you will think I am weird and hate me but I have to confess I did mean them and I am glad she turned me into a sissy. I love pretending to be a girl and being treated like one. And well I was hoping you meant it so I could have a friend, you know." I stood quiet (other than the gasps as my laces were tightened) not sure what to say or do and then I hung my head and said, "I want to be your friend Patsy, I like you and I think your very pretty but I don't know about becoming a girl, I just don't." "I understand and it was too much to ask I am sorry just forget I said anything." She then finished lacing me and I could not stop thinking about her question. It really was nice of her and it was actually an honor for me. I knew that at the time I said those things I DID want them all to be true but I was afraid to admit it. I finished getting dressed and then appeared before Ms. Jamison who received me quite well. I was nervous but she loved my outfit and told me it was perfect for my d?but at work the next day. That night in bed we cuddled closer than we had the night before. Things seemed different somehow; we were more like girlfriends I guess. We had shared things that men never share and that seemed to make us special, we had our bonds released in a way. I slept well even though I was told to wear my corset to bed. In the morning the first thing Patsy did was to tighten my laces. She helped me dress and primp and get ready for work. I then learned that we were to take the bus to work and that Ms. Jamison drove herself. We had nine blocks to walk to the bus station and got many looks on the way. We rode the bus to work and then had to walk three blocks to the office. When we went in Patsy told me to take a seat and wait until she called Ms. Simpson. Ms. Simpson came into the waiting room and Patsy said, "this is Alice, Ms. Simpson she is replacing Mr. Allen who is no longer with us, would you please escort her to her work station, I am sure she will adapt quite quickly." Ms. Simpson gave me a knowing look and said, "So you are the replacement to Mr. Allen are you, I suspect that I can skip the preliminaries with you as you appear to already know most of that so I think I will just take you to your desk and allow you to begin working." She then shook her head and made a "tsk, tsk sound. I began to wonder how many other of the so called women working here were actually transformed sissies? After work Patsy and I would ride the bus home and assume our roles in Ms. Jamison's household. Each night I would be put through one sort of training or another and after two weeks I had pretty well adapted and conformed to Ms. Jamison's wishes. The people at work seemed to not know or ignore that we were sissies if they did know. It was the weekend again and Ms. Jamison was giving me another reward. I lay across her lap bound as before but this time she had added a new twist. A penis gag had been inserted into my mouth. I realized that I consciously obeyed her as she inserted it. I seemed to not be able to resist anything she told me to do. She rubbed and massaged and played with me for some time and then asked Patsy to bring her an ankle binder. I lay there listening to her words but offering no resistance and she put them on me when Patsy returned and resumed caressing me. Then a knock at the door came and I was told to as well as assisted in standing up. I could not move and as my ankles were bound and I was in five inch heels! With my arms bound and lifted high behind my back and fastened to my collar, I was virtually helpless. Ms. Jamison sent Patsy to the door and she soon returned with three women. They quickly noticed me and immediately focused their attention on me. It soon became apparent to me that I was the reason for their visit. I found myself very humiliated and at the same time the sexual high that Ms. Jamison had recently created made me kind of excited at their presence. They looked me over and discussed my training and then Ms. Jamison told them they could make a closer inspection if they wished. Well...they wished and soon their hands were rubbing my legs and lifting my short skirt, rubbing and caressing my legs and bottom and even my penis head. Then they put real fear into me when Ms. Jamison sent Patsy for the strap on's. My bottom had received a butt plug each night for the past ten days and the size had increased to be three times larger than the original. But I had not been penetrated by a woman with a strap on yet and the thought of it scared me. Ms. Jamison took one of the strap on's and a lady named Olivia took the other. They talked about taking turns with me like I was not even there. Shortly after their discussion I was taken to the kitchen table and told to lay over it. A second leash was attached to my collar and it was looped around the table holding my head and neck flat and stretching me across the table with my legs still bent and feet on the floor. My ankles were released and tied off to the table legs so I was spread and bent over and completely vulnerable. Ms. Jamison then said, "Welcome to Alice's deflowering party. I will go first and them Olivia can go next. After that Lisa will have a chance and finally Linda can finish up. Ms. Jamison then requested a pair of scissors to cut my panties off and did just that. The butt plug was removed and I was lubed up and I felt the head of Ms. Jamison's dildo pushing at my hole. It soon was in me and I could not believe how easy I took it. I almost felt a sense of pride as I took it in me. She rested for a moment once I was fully penetrated and then began a slow rhythmic in and out motion. The sensation soon felt very wonderful and I was getting into it. As I did Ms. Jamison quickly noticed my addiction to her hard cock and slowed a bit and then asked me to tell the ladies why I loved being a sissy and why I wanted to remain a sissy after my 30 days was up. Someone but I forget who, put a large mirror in front of me so I could see myself and what was going on. Now if you have never been in this position. Fully feminized, dominated and held in a vulnerable submissive position while a group of real women fuck you, you can't understand how compliant you become. I would have done or said anything to cum and I did. I said what I knew they wanted to hear and did what they wanted me to do. They told me how pretty I was and how sexy I looked and what a good little sissy I was and how if I kept up the good work I could become a real star and fine example for sissies everywhere. I felt like such a pansy but I also have to admit I loved every second of it. Ms. Jamison asked me if I was ready to commit to staying a sissy forever as she had me so close to a climax I would have screamed if a hard cock was not locked in my mouth. I shook my head yes and tried to mumble the words. Oh how badly I wanted to come and she knew it and used it to make me agree too many things. Then it happened, I began to climax. But not like before as a man no this was a different climax one from deep inside and more complete. It was exhausting and deep, not like the ones I had had as a man. Ms. Jamison whispered into my ear, "You did good little girl, now there is no going back. You have climaxed like a girl, you can never think of yourself as a man again. Now the other ladies will each take you over the edge past all masculinity and into the feminine world of submission that you will live in forever forward. Enjoy my dear for you have now become a complete sissy." And each did as she had said. I came over and over and so different than before I felt in love with each of them and even the strap on cocks they wore. As I lay their limp Ms. Jamison removed the penis gag from my mouth and asked me if I had any requests. I said, "Yes Ma'am I do and I hope you will grant it to me. You know that $5,000 that I will earn after being a good girl and a good sissy for a month?" "Yes precious I do but I was hoping you would not want to choose that road after tonight." "Oh yes Ms. Jamison I want it more than anything now. I want to know if I can use it to get breast implants like Patsy has." The four ladies laughed and Ms. Jamison said, "Well I think that is a splendid idea and if you wish I will grant you the money and the implants before your time is up." I was so happy I cried and said, "Thank you," over and over, and then finally I said, "Please put my gag back in so I shut up and fuck my brains out one more time!" Ms. Jamison quickly responded to that request and the fifth climax was the best of them all As she fucked me I thought about how pretty my chest would look with real boobs on it. Yes I was a sissy and I wanted to stay a sissy forever!