CORRESPONDENCE FROM MISTRESS ALISON
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A brief introduction is in order; Mistress Alison is a good friend and a very knowledgeable and experienced Mistress, she has also been a frequent contributor to PDQ. She is now available to answer questions from both Mistress and sissies alike, assuming a respectful tone of course. These email conversations may well be included at some future date in PDQ though a request for privacy would be respected. Feel free to write her at mistress-alison@petticoated.com and please don't waste her valuable time asking "where / how can I find a Mistress?"

Dear Mistress Alison

My wife Susan and myself were reading some of the letters and your replies these past few months while Covid has kept us at home. Susan never heard about petticoating men before. I heard of crossdressers but not sissy maids. Up until now we have lived a vanilla lifestyle so never looked into kinky things. It was funny last week while we looked at things together Susan asked me if I would ever want to dress up like a maid. I thought about it when we looked things together but talked myself out of it. To answer Susan I did with a question which was, "Would she think less of me if I wore women's clothing items like a maid uniform." Susan had to think about it as she did think it was kind of weird. Susan went on to say she didn't think she could be a Mistress or anything like that. Susan is a petite passive woman and not dominant at all. I asked Susan if she wanted me to be her maid would she be a Mistress or dominant? She said she didn't think that was something in her personality.

Susan said to me if I wanted to try to be her maid she would be willing to show me how to do the things she does now. Once again I asked her if it would gross her out if I was to wear all women's underwear with the maid uniform. It wasn't something I wanted to do except all the reading we did pointed to the guys wearing bras and panties too. I asked Susan from the pictures which way did she think would be best for me. Susan liked the conventional black and white maid uniform. I showed her some guys with long hair or wigs to look more like women while others looked like guys in a maid uniform. Susan asked me which way did I prefer then she told me her preference. I thought a shorter woman's wig would be best and Susan liked that way too. Susan asked me what about shoes. She liked something with a 4" heel because that is what she wears mostly. I thought 2" or 3" heels would be something to try. We looked at some pictures where most guys wore what looked like 3" to 4" heels. Susan asked me what about getting both. Then we looked at underwear which I knew nothing about. Susan showed me plain bras and fancy bras. She went to get the one she likes to wear which was more a fancy bra. Susan told me that women like to feel sexy with nice lingerie items even if they don't show it off to onlookers. Susan felt a maid uniform is not sexy so if I was to wear sexy bras and panties I would have that feeling she mentioned.

I let Susan pick out the lingerie after she measured me. We spent hours looking at lingerie, shoes and maid uniforms. It was all ordered before we went to bed. Susan wanted to ask me something but was afraid. I asked what was it so she mentioned chastity devices. We had seen a few which was the first time Susan ever saw one. I asked her if she wanted me to try one of them. Susan then asked me would I like to and if not would I wear one if we picked one out together. I asked why she liked that idea so much. Susan felt why not because other guys had them on. We picked out a pink plastic one since pink is Susan's favourite colour.

One week later the orders arrived. Susan asked me if I was still ok to try the maid uniform on or had I changed my mind. She said if I had then we could just send it all back and she wouldn't be angry. We had a bath together to talk about it more since it was all new to us. Susan told me in the bath that she had noticed all the sissy maids had no leg or chest hair. She asked me if it would be ok for her to shave me while in the tub. I thought that was a weird idea. A few minutes later we were both shaving me. Susan had fun shaving my privates while I shaved my legs. It took a while to shave me clean even though I was not a hairy guy. I cleaned the bathtub while Susan went to put on her robe. When Susan came back she held the pink chastity device. She asked me if she could put it on not having done that before, and I said better her than me. It took her a few tries to get it on with my penis all the way inside. I heard her giggle when the lock clicked. I asked if I could have a key but Susan said maybe later with another giggle.

Then Susan showed me how to put on a bra after I had put on panties. A while later I was dressed like a maid with 4" high heels and a wig on my head. Susan giggled again then said I looked very nice as a maid. I asked her if she really liked me this way and wasn't unhappy with the results. Susan said no she liked the look. She explained after seeing others online it was different to see me that way. Susan asked me if I liked it as much as she did. Sadly, I wasn't as thrilled but would not ruin her fun. Susan asked me if I would wear the uniform every day for a week to give it an honest try. I thought ok if she likes it, I will try it for a week. I asked what about the thing on my penis. Susan asked me to try it for a week too, please.

For the next week I dressed every day as Susan's maid which she liked more than both of us thought possible. Susan showed me how to do work around the house like she always did up until now. Surprising it brought us closer while we worked together of at least I worked while Susan instructed me. At the end of the week we talked about how the week went and what we liked and disliked. Susan was happy with the work I learned to do. Since she is a girly woman she talked to me about being more girly. I wasn't sure what that meant so Susan went on to tell me about painting my finger and toes nails, plucking my eyebrows and wearing some eye makeup. I wasn't so sure about that stuff. Susan said why not it would be fun to see how pretty she could make me. I asked Susan once again if she thought less of me as her maid. Susan said not really but she thought of me more as her maid than her husband which was just fine. I asked her what if she gets sick of it will she let me know. Of course Susan said no worries me being her maid is more fun that she thought from reading and looking at pictures.

Susan started to keep my nails painted, plucked my eyebrows and kept me clean shaven. She wanted me to let my hair grow longer so she could do it up like a real maid would wear. Susan used to be a hairdresser years ago so we have all the stuff in the basement. I asked Susan if I didn't like it would she change it back. She laughed to tell me it wouldn't be that easy but over time it would grow out again. I pointed out one day that we agreed to try me as her maid and her as my Mistress. Susan still said that a Mistress was not something she wanted to be. So I said if I want to stop being her maid what would she say. Susan said she would be sad if we stopped when it was fun for her to help me look like a maid. I just wanted to know if there was a time to stop that Susan would not get all dominant on me. Susan told me to enjoy it and have fun with it.

Over the next month Susan bought me more uniforms in different colours, more panties and bras. One day I said Susan I have more maid clothes than guy clothes. She smiled to let me know it was ok with her for me to enjoy having more. Susan felt it to be better if I had a variety of uniforms since I wore them every day. The day Susan did my hair she commented that I looked more feminine that every before. Susan asked me would I ever consider going for a drive in one of maid uniforms or would I prefer to wear a nice dress for a change. I stopped Susan right there and asked what she meant by going for a drive. Susan felt I looked very much like a woman from a few feet away so why not go out for a change. Susan said if I was too afraid then maybe another time.

A week later Susan showed me a new dress she bought and asked me if I liked it. I said yes it was very nice as usual. Susan asked me if I would like to try it on for her. I said ok without knowing she bought it for me in my size. Susan said, "Oh I like that on you very much." She went to get a purse for me to hold for a different effect. I put the strap on my shoulder and posed for Susan. I heard her say OMG you look so good. The dress, shoes and hair make you look so much like a woman she said to me. I looked in the mirror and was surprised the dress changed my look from the daily maid uniform. Susan freshened up my makeup then said come on let's go for a country drive. My heart dropped to the floor. Susan said again come on it's going to be fun.

In the car I went looking around to see if any neighbours watched. We were gone for a couple of hours which gave me a chance to see what it would be like to go out as a woman. Susan enjoyed the drive with me. I felt Susan was getting into having me as a girlfriend and maid more than a husband. It had been weeks since the chastity device was locked in place. Although Susan wasn't dominant she had a way to keep me interested in my role as her maid. Every time I brought up going back to the old ways somehow I ended up keeping my maid uniform on. I didn't even look like my old self anymore with my hair curled, makeup every day, eyebrows shaped and plucked, hairless body, in chastity and painted nails. I would ask Susan if she had enough of me as my feminine self once in a while. The answer was please continue I love you this way. Then I would go away confused yet keep my uniform on.

Susan talked me into going out a few more times with a different dress each time. Winter came so she bought me a long coat and knee high boots. Susan was very good at helping me look as much like a woman as possible. She taught me to walk and carry myself like her. Susan talked me into going to a mall to walk around just to practice my walking. I started to give in to Susan and think of myself as her maid and not her husband any longer. Susan was always nice to me and never raised her voice all the years I knew her. It was just part of her the way she was able to talk me into things. I can't explain it but look at it this way from the beginning to now. I look and dress like a maid and a woman. At no time did I say no Susan. That is because she has this way about her of getting me to do things. There were many times I asked if I could just put on a pair of jeans and t-shirt. Susan would talk me into put something pretty on instead. She bought me nightgowns to lounge in after dinner. In Susan's mind I was more feminine than masculine. I felt more feminine and at times tried to escape from it all. Susan taught me to cook, clean, launder, polish and iron our clothes. She taught me how to do her nails and my own.

One night a month we would go look on the internet to see how other couples lived the lifestyle. Susan never wanted to be a Mistress or dominant. Instead she developed a way to keep me as feminine as she liked without me complaining. We talked about her way of getting me to not only do something, but want to do it for her. Susan didn't know how she did what she did as it was just a natural thing about her and me. I gave her an example of me wanting to stop a few times, but within minutes I was back in line with her way of thinking. Susan said if I wanted to stop she wouldn't stop me not that she felt she could stop me. Then within the same minute Susan admitted it would make her sad when we have had so much fun together and wife and maid. How the heck do I walk away from this life when Susan keeps supporting it?

Susan read me a story about a couple similar to us where the husband changed to live as his wife's maid fulltime. The story described much of the way we live but with a twist Susan continued to read that the wife wanted her maid husband to have breast augmentation for her. At first he was shocked and even tried to say no way. The story went on to tell about the day he went for the surgery and how it changed their relationship. Apparently he became that much more feminine and they became closer than ever before as though they were girlfriends. When the story was over Susan asked me if I would ever consider having breasts. My answer was the fastest answer yet, which was No Thank you Susan. It was quiet for a while as we both thought of what just happened. Susan actually brought up something that would make me permanently feminine. She realized the effect it had on me so she apologized later. We talked about it as we did with everything to date. I asked Susan did she think I wanted to have breasts because I dress as a woman. Susan said no she didn't think I wanted breasts as we had never talked about it before then. I said if I had breasts my life would change in a way that it would only be feminine. Susan asked if that would be a bad thing while she thought I liked being feminine for her. I would say I like it but instead I do it for her and if that makes Susan happy then I am happy to do it. Susan asked me if I would stay as her maid for the rest of my life and be her girlfriend on weekends. I thought about it for a while since the rest of our lives was going to be a while. Susan asked me if I still enjoyed wearing women's clothes and having my hair and nails done by her. How could I say no without hurting Susan's feelings?

Susan brought up breasts again letting me know I might like them She pointed out my breast forms were showing quite often where cleavage would be more natural looking. Susan felt if I was to remain as her maid and weekend girlfriend why not go that extra step to be more feminine. There was pressure to get breasts from Susan as she made sense the way she put it. I was always concerned Susan would get sick of my feminine look or leave me for another man. She assured me that my living as her maid was much more important than meeting anyone else. Susan told me that if I didn't look so feminine she would never talk about me having breasts. We had been out a few times and not once did anyone look or say there is a guy under than dress. I was there so I knew she was right that I had no trouble passing as a woman from a distance. Susan wanted to try going in a store to buy a new bra by myself while she watched. I was terrified yet Susan felt I could do it. She said if I can go into a woman's shop and buy myself a bra would I think of getting breasts then. I thought about it knowing full well the women in the shop would know I was not a real woman but maybe a transgender woman.

It was a week later that we went to the mall where Susan had been buying my bras. We both went in me going one way and her another. I picked up my bra then headed for the checkout. The lady smiled then asked if I found everything I was looking for today. I smile back with a faint yes. When the transaction was finished she said have a nice day and hope to see you again. Susan caught up with me to ask how did it go. I told her the truth that the lady never said anything even if she knew I was not a real woman. Susan said see there was reason to be scared when you look that good. I said I suppose you think I should get breasts now. Susan said only if you want to get them. She wanted me to have her support and be part of making the decision. In the car on the way home I let Susan know if I got breasts there would be no turning back and that sooner or later some friends and family would know too. Susan let me know she had thought about it already. She felt it is our life together and we deserve to be happy. Our happiness has nothing to do with others family or friends. Susan agreed that breasts would be a game changer for life. We talked about how our life was before looking at maids online. It was rather boring yet we always got along together. Since I became Susan's maid we grew closer and had more things to do together. I learned more about Susan as a woman and woman related issues. Susan taught me how to be a better person, about fashions and lots about cooking. Susan felt if I was to get breasts we would have the rest of our lives to learn and share more things in common. To be honest there was nothing bad about becoming Susan's maid other than sore ankles and calves every so often. I found the clothing very comfortable and stylish. I got used to having my hair done and wearing makeup. Susan taught me how to do all those things and in return I looked after all the housework. You know what they say. A happy wife makes for a happy life. That is so true for me.

Susan took me to a clinic to see about breast implants. I wore a pretty dress that day so I was convincing when the doctor came in the room. She asked me several questions and showed us the types of implants. Susan asked me right there if I was sure about going ahead. I signed the papers and Susan witnessed them. A week later I went to get breast implants with Susan by my side. When I woke up I was in some pain as I looked at my chest. Susan was beside me when I woke up. She said you did it and everything went well. The next few days were on and off uncomfortable with drain tubes sticking out. A few weeks later I was wearing one of my bras instead of the post op bra. Right away I noticed the weight of having breasts and how they moved when I walked. Susan asked me if I had any regrets as she felt guilty for a few days when I was taking pain pills. I let her know it was my decision to have breast with her pushing me to do it as we both laughed. We went shopping to buy me a new dress to celebrate then out for dinner. A friend of Susan's met us so she was surprised to meet me as Darlene and not Derrick. She commented part way through dinner at how good I looked and how happy we both appeared to be. Susan replied, "Yes we are happier than ever before."

Mistress Alison, at one point I was going to write to you to say help me get out of this, but as time went on Susan helped me more and more. I'm not sure how other guys deal with women who have the ability to point them in a certain direction. I stuck with Susan even when I wanted to quit the maid life. Susan had and has a way to make me feel comfortable with myself.

I hope you find our story interesting.

Regards,
Darlene

Dear Darlene

Thank you for your fascinating letter.

You said several times that your wife, Susan is not naturally dominant and that she told you it was not something in her personality. Well I beg to differ; she may not look or act like most people's idea of a dominatrix or a Mistress, or use the more usual techniques of a dominant, but she has changed both you and your life irrevocably and got precisely what she wanted. I'd say she has been far more effective than any woman who dresses up in leather and brandishes a whip or crop.

You also said that you had been going to write asking for my advice on how to get out of your situation. Had you done so I would have replied that I doubted you really wanted to. Your penultimate sentence was "Susan had and has a way to make me feel comfortable with myself" which suggests you are happy with the new you she has created. She very obviously prefers you as a girly maid to a conventional man and intends to keep you like that whatever.

To quote another line in your e mail, "A happy wife makes for a happy life," you have achieved what few men seem to be able to achieve and made your wife (Mistress) happy through your compliance. You should celebrate this and continue to serve and please your wife and reap the rewards it brings.

Yours sincerely
Mistress Alison

Dear Mistress Alison

Thank you for reading my letter and offering some insight. Susan was always a very passive woman who never raised her voice even when someone did a bad thing to her. Neither of us were fighters growing up. I see what you mean by Susan not showing me dominance yet it is there. She is still very soft spoken yet she gets her way with me all the time. I am not complaining at all as I love her dearly.

We are a happy couple even though we live a different life than before. Susan has some great ideas so I just go along with her to keep peace at home.

I'm glad I shared our life with you since not too many people know.

Take care,
Darlene

Dear Darlene

I think that the words "neither of us were fighters" speaks volumes, and can't help wondering if either or both of you are too diffident to reveal your true natures, even to one another. Susan as a dominant and you as a submissive, and that you have just adopted those roles almost as a way of avoiding conflict.

Be honest now, would it excite you if Susan were to look and act the role of a Mistress rather than a bossy wife? Would it make you feel elated or uncomfortable to kneel in front of her and call her your Goddess? If you told her that through your service to her you have found your true m├ętier in life and would dearly love her take things further, how do think she would react?

I ask these things for a reason: just because life seems good and comfortable at the moment doesn't mean it can't get even better. Any relationship that fails to grow and mature becomes stale and then withers and dies. It is certainly worth discussing them with Susan.

Yours sincerely
Mistress Alison

Dear Mistress Alison

I think it makes sense that we adopted the ways since we never ever fight or argue. Usually in the past we just tried to avoid any conflict instead of arguing since we are not good at it. When Susan wanted something I just gave in and so would she. Susan is not a bossy wife or a Mistress. I asked her if she would like to be my Mistress yesterday when we were talking. She said ok except no yelling or hitting like what she read about online. When I kneeled before Susan she liked when I did that as she said she felt like a queen.

I understand what you mean to find a way to keep things in the relationship going. Right now with me in a feminine role with Susan things are fresh as they say. Susan likes everything we are doing. I will ask her again about wearing the Mistress title to see if she can take and run with it. It isn't her nature to be mean or nasty however she likes when I do what she suggests.

We are still finding out how this life can work for us. Susan does like me in a feminine role that I can see every day. I asked her if she would ever have wanted to live with a woman. She said not at all but she liked to help me be like a woman knowing I am still a man under the women's clothes.

Susan is calling me so I must go for now.

Take care,
Darlene

Dear Darlene

Being a Mistress is more a state of mind than anything else. It means giving orders rather than asking, and expecting to be obeyed with question or complaint. It means doing whatever you like in the manner you like without ever having to explain and never having to do anything you don't wish to. It means being placed on a pedestal and worshipped.

I never raise my voice because I don't have to, I never swear or use bad language and I never insult or demean my sissymaid. She is giving me her total commitment and obedience, I know if I ordered to jump out of the window or put her hand in the fire she would do it without hesitation, but of course I would never do either of those things and she knows it. She trusts me completely and I would never abuse that trust. She always puts me first and considers my needs and desires to be paramount, my comfort comes before hers and serving me makes her happy. When I smile or praise her she is in heaven. The bond between us is a very special form of love and every day she makes me feel like a queen. I am her Mistress, but I'm neither an ogress or a sadist, I control every aspect of her life, but I also take care of her as a queen should look after her loyal subjects.

I'm sure Susan would love it if you made her feel like a queen every day too and reward her most loyal subject.

Yours sincerely
Mistress Alison

Dear Mistress Alison

Susan has been giving me more things to do to keep me busy. I never realized Susan did so much before we dove into this new life of ours. We are getting along very well with Susan trying to be more dominant although she still has the soft voice. In a way there is not much change in Susan as I see her the same woman as before this all started. I do know from talking with you Mistress Alison that sooner or later Susan will take on that dominant role. On my end I do everything Susan asks or tells me to do. Most of the time Susan asks me to do things. She has commented on my look as she has said a few times I look better as her maid than before as her husband. Susan was teasing me the other night when she said I didn't have to get the breast implants if I didn't want them. I was like now you tell me. Susan said that she was proud of me for getting them though and now that I have them she wants me to always have them. I do like wearing my maid uniform more now that in the beginning. I like wearing a bra then again I don't have a choice right now.

Mistress Alison, how long did it take for your sissymaid to get used to his role and how long did it take for him to get used to wearing women's clothing? I think I am getting along pretty good but wanted to know how others make out.

Regards,
Darlene

Dear Darlene

It sounds as though things are all going in the right direction and that Susan is taking things at her own pace, just as she should, and you are accepting it, just as you should.

The thing about this lifestyle is that it is a journey, an exciting voyage of discovery that has no destination. It's all about the things you discover along the way, and the wrong turns and dead ends you might take along that way simply make it more interesting.

My sissymaid, kitty was already a cross dresser when I first met her and the most naturally submissive person I've ever met. It was she who persuaded me to become her Mistress, and at first I was very reluctant. I certainly didn't want deliberately to cause her pain, but she was very persuasive and I had good mentors, Auntie Helga being one of them. Ever since both of us having been growing into our respective roles and now I couldn't imagine being in a vanilla relationship or not having total control. As I written many times before power is both erotic and highly addictive.

Yours sincerely
Mistress Alison

Dear Mistress Alison

I am glad you shared the kitty story with me. It confirmed Susan and I are in the right place with no particular destination as you put it. I have never asked Susan what is next or how long or anything like that at all. Susan has never given any indication about where the journey may end up which is good for both of us. I read about a sissymaid who asked too many questions about when, where and why. It didn't turn out well as his Mistress became very angry over the 20 question routine. Susan and I just take one day at a time together. She is very happy with how things are at this point and so am I. That is all that matters don't you agree?

Regards,
Darlene

Dear Darlene

I couldn't have put that better myself. Just trust Susan to lead you where she wants to go. Obey her without question or complaint at all times, let her know how much you love, worship and adore her and be happy for her and with her and both your futures will be rosy indeed.

Yours sincerely
Mistress Alison

Dear Mistress Alison

Susan and I are learning together where she is learning how to be more in charge and I am learning to server her like my queen. Our relationship is strong just as it has always been. We never argued before which makes this change in our lives so much easier. When Susan wants something done she asks me to do it then I just do it. The way we used to work was if Susan wanted something done I did it because she asked me to do it. Susan would not ask me to do something if it didn't need to be done so why would I ever challenge her? The same goes now I just do what Susan wants. To me it is easy to do what Susan wants as it is nothing new.

Susan and I are enjoying the new life we have together more than we did before. It is hard to explain the love we have for one another. It would be safe to say I love Susan more now than I did before even though I always loved Susan.

I had the drain tubes removed from my breast surgery on Thursday. The doctor said things were healing well and she was happy with the results. In another 2 weeks Susan will take me for a bra fitting when I can take off the post op bra. This is all new to me so probably not interesting to you. Women are lucky they grew they breasts slowly then adapted to having them. For me it was overnight. Susan is proud of me for letting her talk me into having the surgery. That is where trust comes in to the picture.

Anyways I wanted to say hello to you and let you know we are still out here working hard to make things work like you and kitty.

Regards,
Darlene

Dear Darlene

Good news about your surgery, you will find walking much easier when the weight of your breasts is being properly supported in a well fitting bra. As you say it all about trust.

Yours sincerely
Mistress Alison

Dear Mistress Alison

Susan and the doctor told me that a full support bra will be necessary for quite some time while my body heals. The weight of my breasts is something to get used to especially wearing heels. I know it will take time to get used to living as a sissymaid. Susan said I am doing well so far. That makes it worth while to hear for me.

Regards,
Darlene

Dear Darlene

The combination of breasts and heels can make walking feel awkward at first. If you don't already do so then wearing a corset can help keep your back straight later and has the advantage of encouraging you to walk from the hips rather than the knees, which will give your gait a feminine swing and make your bottom wiggle.

Yours sincerely
Mistress Alison

Dear Mistress Alison

I will ask Susan about a corset to help me walk better with heels and breasts. Susan and other women make it look so easy when they walk in heels. We know a woman who is very large breasted who wears heels every day. I wondered how she could so it and not fall forward. Now I am learning myself.

Thank you for sharing your life with me Mistress Alison.

Dear Darlene

You're welcome.

Learning to walk in heels is like learning how to apply your make up, it's all part of learning how to be a woman. Biological females learn it in their teens, usually with help from their mother or older sister(s) but, like everything else worth having, success isn't achieved overnight or without effort. Fortunately you have Susan to guide and help you.

Although I frequently tell those who are nervous about embracing the new that the two saddest words in the language are, "If only," wondering about what ifs is always a fruitless exercise. To paraphrase Polonius, grapple what you have to your soul with hoops of steel and be grateful for it.

I wish you both well in your lives together as new people.

Yours sincerely
Mistress Alison

Dear Mistress Alison

Happy New Year.

I haven't talked to you in almost a month due to my busy lifestyle as Susan's maid. She has shown me how to do all the housework through the whole house. Susan has also helped me look and feel more feminine now that I wear makeup every day. I have to admit I do look more feminine than every before. My hair is growing and my breasts have healed up. It took some getting used to having my own breasts, well implants that is. Susan is pleased with how far we have come making me the feminine maid and house wife she had read about by other women.

You had suggested Susan buy me a corset to help with my figure. She liked your idea and a result I now am corseted Monday through Friday. Susan makes it pretty tight so I have to bend over at my knees more like she would rather than the way I used to bend over. Susan wants me to always do things the way a woman would and drop my old male habits. I know she is right and I am working hard to please Susan for giving me the opportunity to serve.

I hope you had a wonderful holiday season. Like most families this Covid thing impacted ours but Susan wasn't ready to show me off to the whole family. She said by next year everyone will know.

Regards,
Darlene

Dear Darlene

A very Happy New Year to you both.

It sounds as if everything is going well for you, and you are progressing in the right direction under Susan's guidance.

As you have now discovered wearing a corset doesn't just make you look more feminine; with a narrower waist and more pert bottom, and give your hips that alluring wiggle, it also forces you do things in the way a woman would. It also has another advantage that is purely psychological. Its firm but gentle embrace is a constant reminder of the authority your wife (and de facto Mistress) has over you. It is she who put you into it and insists you wear it Monday to Friday, she who laced it so tight, she who has the power to tighten it more or loosen it if she so wishes. With every move you make you are reminded of this and of the fact that you are you wearing it to please her and must always do your best and try your hardest for her.

You once told me "I do like wearing my maid uniform more now that in the beginning. I like wearing a bra then again I don't have a choice right now." That's now even more true than it was then. You have become in effect a 24/7 sissymaid and there will no going back for either of you, and I suspect that neither of you want to. Susan has told you that next Christmas everyone will know; and, trust me, the day she thinks you are ready to be shown off to the family will be the proudest moment of your life. You will have attained the required standard, become the person she wants you to be and demonstrated your love and total commitment in the sincerest way imaginable. Exciting times lie ahead.

Yours sincerely
Mistress Alison

Hi there Mistress Alison,

Mistress Susan is working to make me look more like a woman. This week she coloured and cut my hair then put it in curlers. Mistress Susan plucked my eyebrows which hurt like you know what. My nails are filed and polished in pink. I'm learning more what it is all about to be a woman at least from clothes and personal care. Other than tightening my corset I dress myself and get ready every morning while Mistress Susan sleeps. When Mistress Susan gets up she tightens my corset then has her breakfast.

Last weekend the neighbour lady came over to have tea with Mistress Susan. Before she saw me she asked Mistress Susan if I had a maid. I guess she saw me through the big window at the front of the house. Mistress Susan called me to come meet the neighbour lady. I curtsied to the lady then went about my duties. I heard them talking about me as a maid. The neighbour lady wanted to know how Mistress Susan convinced me to be her maid. I tried to keep my distance so not to listen to the conversation and so that the neighbour lady didn't ask me questions.

Mistress Susan is happy with me as a sissymaid. She wants me to look more feminine so in time I can do the shopping for her. When I asked if she was serious about me shopping the answer was, "Yes in good time Darlene." We never talked about me leaving the house so it came to a shock to me. I know Mistress Susan would never tell me to do something that would endanger me. I'm learning Mistress Susan wants to push me further than before. I think she has talked to another Mistress but not sure.

Regards,
Darlene

Dear Darlene

You continue to make excellent progress and Mistress Susan obviously has great plans for you. That's the thing about this lifestyle, and indeed FLRs in general, it's progressive, and as Mistress Susan becomes more comfortable exercising her power over you she will push you further and further, and as you get more accustomed to serving as her maid, you will want her to push you and you will want her make her proud of her sissymaid.

Being shown off to your neighbour is just the first stage and I bet you felt a real frisson as you curtsied to Mistress Susan's guest. You will feel the same mixture of nervousness and excitement when you go on your first shopping trip and will think everyone's looking at you, but don't worry they probably won't and if those that realise the truth under your clothes are unlikely to say or do anything other than perhaps snigger. Just tell yourself, "So what if they snigger, I don't care, I'm a sissymaid on a mission and Mistress Susan expects me to accomplish it and accomplish it I shall." It's all about confidence and mental attitude.

What makes you think Mistress Susan has spoken to another Mistress? She hasn't written to me, though naturally I would be pleased to hear from her if she so chooses.

Yours sincerely
Mistress Alison

Hi There Mistress Alison,

Susan has taken to her role as my Mistress more than I ever thought possible. As you know Susan has always been a soft spoken woman who basically got me to do things through her niceness if there is such a word. That hasn't changed all that much although I hear in her tone a more dominant Susan that the woman I married. Susan talked me into having breast implants, growing out my hair then having it done at a salon her friend owns. My ears were pierced, nails done and eyebrows thinned and shaped. With all that done Susan's goal continues to be to feminize me. Last week Susan insisted I go grocery shopping with her while wearing one of my many maid uniforms. It was horrifying to me as I pushed the cart with my head lowered at times. Susan stopped a few times to talk to people she knows while I stood there waiting. Susan began treating me more like her property than her husband lately. I was introduced to one lady as maid Darlene. The lady smiled at me a few times while Susan talked to her not about me, just general chat. When we got home Susan asked me how it went from my point of view. I let her know it was horrifying. Susan let me know it was the first of many outings so not to worry about it. She said all of that with a smile then Susan walked away while I put the groceries away.

This new life is challenging almost every day. The part that helps is knowing Susan loves me and appreciates the work I do for her. I was treated to intercourse on Sunday after weeks of none. Susan was pleased that I was able to perform. I was thrilled to have been able to perform.

I hope you and your family are safe and healthy.

Regards,
Darlene

Dear Darlene

Things have happened more or less as I thought they would and wrote to you about in my previous e mail. This is all well and good and I suggest you re read the penultimate paragraph of that e mail.

My only criticism is that you kept your head lowered as if you were hiding some shameful secret. You should be proud of what you are doing, serving the Mistress whom you love and worship. Think of all the things you have done, what you have achieved and how far you've come since you first wrote to me. You did it all for her and you should be proud of that, and proud of yourself, it took courage and commitment and above all else love. By submitting willingly to her authority you are demonstrating that love in the sincerest possible way. So next time, and every time thereafter, hold your head up and dare the world to challenge you; if you keep your back straight and take small, precise feminine steps most observers will neither realise or care. If anyone does say anything tell then, "Yes. I am a sissymaid for my beloved Mistress, I'm intensely proud of that fact and it is absolutely no business of yours how I choose to dress so please go away and mind your own business." Do it with sufficient aplomb and they will become the ones who feel embarrassed and hopefully ashamed too.

You say that Susan is treating you more like her property than her husband. The truth is that your relationship has now change irrevocably from that of husband and wife to that of Mistress and sissymaid. My sissymaid, kitty, would say that means you have become her property; to use, to command, and to control in any way she sees fit, but it is important to realise that this doesn't mean she loves you any less. In fact she probably loves you even more, just in a different way. She is obviously enjoying her new role and you should enjoy the privilege of serving her too.

The very fact that you used the words "This new life" indicates that you have now accepted most of this and the more you accept it the happier you will become. I'm not saying life will become any easier or less demanding, the life of a sissymaid is never an easy one, but you will find an inner contentment through knowing you are serving your Mistress well and that she appreciates what you are doing and the sacrifices you are making for her. She has shown how much she appreciates you and your efforts by rewarding you with the ultimate privilege. Carry on as you are doing and such treats will become less infrequent and your joy all the more intense.

Yours sincerely
Mistress Alison

Hi there Mistress Alison,

Thank you for the feedback on how I am doing both good and bad. I'm trying very hard to do everything that Susan demands of me and more. Maybe I misunderstood when I lowered my head in the grocery store. It is something I do at home when I'm with Mistress Susan. After I read you comment I now understand better. I will be proud of who I am next time we go shopping. I do have the walk down well enough that met with Mistress Susan's approval. It did take practice because men don't walk like women. Yes, I have accepted my new life just as Mistress Susan has accepted her role as my Mistress. I'm learning slowly to embrace this lifestyle. It took a while to get used to doing the opposite that I did as a man. For a guy to learn to be more like a woman from clothes to hair it not easy to do. It got better when I was more comfortable with my appearance and my role with Mistress Susan. Now I have to get ready to cook dinner.

Thank you for helping me again.

Regards,
Darlene

Dear Darlene

You're welcome, it's what I'm here for.

Don't worry too much about making mistakes, it's a big change for you and Rome wasn't built in a day. Lowering your head as a sign of respect is one thing, hiding your face is quite another, but Mistress Susan will cure you of these errors. Just trust her and obey her. Perfecting a feminine walk was a big step (bad pun entirely intentional) but thinking not just like a woman but a female servant is an even bigger one. Sissymaids are a breed apart and though some, like kitty, are born most have to be trained and that takes time and patience. Most Mistresses use some system of punishment and reward, the proverbial stick and carrot, to help the training process and I suspect that in her own good time Mistress Susan will introduce one that is appropriate for your own particular situation. It is important for you to recognise that any punishment is there to help you improve and that you should be grateful for it rather than resent it. Don't let that frighten you, punishments don't have to be brutal or necessarily involve physical pain, something as simple as the writing of lines can help concentrate the mind and prevent the repetition of errors.

Keep up the good work and be happy in your new life.

Yours sincerely
Mistress Alison

Hi there Mistress Alison,

The weekend is here again which is when Susan is home with me. It's also a time when we do things together or Susan wants to do some training. This morning we went out to get groceries and then stopped to get gas in the car. Grocery shopping once again a challenge for me even with a mask on while shopping. Susan encouraged me to act normal to blend in like other women. I did my best but it was scary for me. The good thing at the gas station was being able to put the credit card in the pump so I did not have to go in the station to pay. I thanked Susan for letting me pay at the pump rather than go in the station. Susan told me that over time I will get more comfortable with my new self as she will expect me to go out to do more errands alone.

Sometimes I think back to when I was just a husband and how life was so simple. Today Susan has feminized me in hopes I forget about my husband ways. Most of the time I am the feminine maid Susan wants me to be while other times I get confused. When I come out of the shower I look down to see breasts and my penis in a cage. For those few minutes I wonder what and who I have become. The minute I put on my panties and a bra it is clear to me again. I'm Susan's sissymaid.

Mistress Alison, does your sissymaid ever get confused about who she is or is this just a me thing? Will I always have some confusion or will it all sink it at some point?

Regards,
Darlene

Dear Darlene

It's good that Susan is pressing ahead with your training and you are doing things together as Mistress and maid.

The longer it goes on the more comfortable you will become with going out in public as your new self. As some sage once said, "If you worry about what people are thinking about you then you would be probably be upset to learn how just how infrequently they think about you at all."

In reply to your question about kitty: the answer is: no, she never does. Kitty looks like a sissymaid, acts like a sissymaid and most importantly thinks like a sissymaid 60 seconds of every minute of every hour, 24/7. She has been cross dressing since her early teens and has been my full time sissymaid for almost ten years. It is what she always wanted to be, she is the most naturally submissive person I've ever met and loves her job, which she calls her vocation in in life, her true calling. She regards the time before she became a sissymaid as an aberration which she would rather forget about; she hates wearing what she calls drab and only does so when absolutely necessary. The last occasion, at my insistence, was for her mother's funeral more than 3 years ago. She wanted to attend in a skirt suit, but I made wear trousers as a mark of respect. Given time you will lose any lingering identity confusion, just keep telling yourself that you are being the person that Mistress Susan wants you to be, she loves you just the way you are and that's all that matters. It's a bit like walking in heels, at first it seems impossible and you wonder how on earth woman manage it and why they put themselves through such a daily ordeal, but over time it becomes second nature and you just stop thinking about it.

Yours sincerely
Mistress Alison

Hi there Mistress Alison,

Once again you have steered me back in the right direction so I thank you. Every time I talk with you in email I walk away feeling better about myself. There is just something about the way you word things that tells me to do as you say without any questions. Why no questions? Simply because you just make perfect sense each and every time. Wow kitty has been your sissymaid for 10 years? I am glad to hear that she loves the life so much that she prefers that over her previous life. That in itself is a motivation for me to keep going. I let Mistress Susan know that kitty has been your sissymaid for 10 years. Her answer was, that is excellent just as I will get to the 10 year mark before we know it.

I asked Mistress Susan if she preferred all men be sissymaids now that I am hers. She said no only those that are best suited for the life to serve their Mistress. There has to be some good strong men out there to satisfy the women of the world as well. I wanted to know what percentage Mistress Susan felt should be sissymaids. Mistress Susan laughed then told me probably 70% or more of all men should be sissymaids. Mistress Susan felt that in time women will take over the planet and the only logical place for men will be serving women. In the meantime, Mistress Susan is helping me adjust in every way possible.

Regards,
Darlene

Dear Darlene

Thank you for your kind words.

A question perhaps you should be asking yourself is "Why am I asking Mistress Alison instead of Mistress Susan?" I may have more experience, but Mistress Susan is obviously a woman who knows what she wants and your role in life is to be that person, to obey her without question, and to love her and cherish her. If you think about it that's hardly an onerous task, is it? Striving to please and satisfy the woman who means the world to you, to put a smile on her face and joy in her heart.

I think the world would be a far happier and better place if all men were under the strict control of a loving female authority figure. That doesn't mean they should all be sissymaids, just deferential, respectful and obedient and less concerned with macho posturing, which boils down to "my willy's bigger than yours" playground rivalry.

Being a big strong man doesn't automatically mean a male can't be a sissymaid, and being a sissymaid certainly doesn't mean they are incapable of satisfying a woman where it counts most, in bed. Kitty is young enough and fit enough to have remarkable stamina and of course her dedication to putting me first each and every time makes her far and away the best lover I've ever had. She might be a super submissive sissymaid, but if she thought anyone was threatening me, she'd toggle in an instant into a roaring lioness and go straight for the jugular no matter what the odds. She certainly doesn't lack courage. It takes great strength of character to be what she is and live as she does, so I get the best of all possible worlds.

Yours sincerely
Mistress Alison


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