FROM STUD TO MAID
from Brent

Dear Auntie Helga,

My name is Brent a 23 year old guy with an interest in older women with huge breasts. I found most of the women I dated on MILF websites where they were looking for younger guys and younger guys were looking for them. Last summer I met a woman named Nancy who was 47 years old and has huge natural breasts. We hit it off which ended up us no longer looking for other partners and living together. Nancy is a successful business woman with me taking odd jobs here and there but never finding something I could call a career. Nancy would have liked to see me find something and had hinted if I didn't she would give me lots to do at home during the day. I admitted at my age having fun and having lots of sex was pretty important where working wasn't on the top of my list.

A few weeks ago Nancy sat me down to talk about our relationship and how much we mean to each other. She went on to say that in order for her to have the time to go out together a few times a week she wanted my help at home. One afternoon Nancy gave me a book to read called My Husband is My Maid then left the room. I took a look at it then laughed thinking no way was I going to be anyone's maid. Nancy asked me to read it for her then we could talk about it later on. Rather than make a big deal about it I read the book for her. Nancy is a beautiful woman and I don't want to lose her to another young guy.

She called me into her office telling me to sit down beside her while she showed me petticoated.com and I began to get very nervous. Nancy showed me lots of men dressed in maid like dresses who worked for their wives, girlfriends and mothers. I agreed that I would look after the house and do anything she wanted but didn't like the idea of dressing like a maid. Nancy told me how much she loved me and of all the young men she has dated she could see spending the rest of her life with me. I knew we loved one another and had amazing sex together but I was not a maid. In a business like way Nancy said to me that she had thought long and hard about this so it was what she wanted from me. She went on to say living life as her maid would be wonderful with me not having to worry about a job or money any longer.

Before I could refuse she took my hand leading me to guest bedroom where she told me to take off my clothes so she could show me something. Before I knew what was going on Nancy had me wearing pink panties and a pink bra with huge cups. Then she took out these huge silicone breast forms and put them in the bra. Nancy told me she knew how much I liked big breasts as she said to me those were the biggest she could find. I tried to talk but she put her hand over my mouth then proceeded to dress me. A few minutes later I was standing there in a pink French Maid type dress with huge breasts and wearing high heels. Nancy said Brent you look cute as hell and maybe even better than she would in that dress.

She showed me another dress and a bag of bras, panties and stockings that she wanted me to start wearing every day. I tried to talk to Nancy about it but she told me not to worry everything would be fine. That day Nancy started to teach me how to do the things that she didn't have time to do. Each day she helped me get dressed then gave me a list of things to do before she went off to work. At night we had great sex just like we did before. I learned that Nancy was happier and had more energy to do things, with me attending to the house work. I got used to carrying around the huge breast forms in my bra and have a much better appreciation of what Nancy goes through with hers.

Nancy continues to read letters on petticoated.com and other sites sharing with me what some women do to their maids. Sometimes it makes me nervous she will try something like that but she assured me that all I have to do is be her cute maid and it will be fine. Nancy showed me pictures of maids in chastity but she said I am lucky that my penis is too big for one of those devices and besides she wouldn't want it in chastity. That is one of the reasons I started to date older women as they could enjoy a large penis where younger girls couldn't.

While I get used to dressing like Nancy's maid I can see that it makes her happy. She likes to buy things for me and have me model them for her. If I was to guess I would say that Nancy's maid idea has strengthened our relationship. Nancy paid off my credit cards which I have to pay back working for her at home. She is teaching me to cook, clean like she used to do and even iron her clothes for her. It is hard work some days which also showed me what I used to take for granted. Nancy laughs at me now when I am tired or have sore feet or have a run in my stockings. All the things I had no idea about before I live with every day now.

The best nights and days for me now are when Nancy tells me to get ready to go out for dinner. The only thing I have to wear at all times is pink panties but wearing my guy clothes out for dinner is now a treat for me. It is fun going out with Nancy as many people think we are mother and son not mistress and maid. I asked Nancy if she ever thought of us going out together only with me being dressed more like her. I had read that in a letter that a mistress took her maid outside. Nancy said it wasn't her plan to do something like that unless I wanted to try it. If I did she would buy something nice to wear so we could go out together.

We have an open relationship where either one of us will ask the other a question without worrying if that is alright. I would rather know what Nancy wants from me instead of getting surprised again like the day she put in a maid dress. Nancy admitted it wasn't in her plans but did think it would be nice to go out together with me in a new dress and new shoes. Nancy told me that I would have to get my hair done or wear a wig to blend in on the outside. I thought wig would be easiest as I am not looking forward to having my hair done any day soon. Nancy told me that she will work on the idea over the next few weeks then let me know. At least I know now that Nancy would do some of things she read if I was willing to try it for her.

I am taking more of an interest in being a maid as I like to read about it when I have time. There are some unhappy maids but most are happy in this type of role and if not their wives, girlfriends and mother are happy that's for sure. I'm thankful that Nancy is a very sexual woman and has not cut me off like some of the women in the stories have done. In fact the other night Nancy was fooling around teasing me which ended up her having sex with her maid. I never had sex with any women while wearing a maid dress before.

I am sorry Auntie Helga for writing so much but I think this was good therapy for me to write down my thoughts and happenings.

I hope you approve
Brent


Thank you for your letter Brent. How nice of you to write and with quite a delightful letter. You are so fortunate to have found such a wonderful and amazing woman and now you have an opportunity to live a life of comfort and love, of course its only right that you do a bit of work for her largess and being dressed as a sissymaid just makes it perfect. In time you will grow to love your pretty clothes, how they feel on your hairless body and how much your Mistress loves seeing you.

I understand your need to talk about this and I am happy to listen, I hope it was cathartic for you and I would be happy to hear from you anytime, feel free to write.

Be obedient and enthusiastic, it would be nice to curtsy to your beautiful Mistress when she walks in the door, or you could drop to your knees and kiss her feet and thank her for this wonderful opportunity.

Auntie Helga

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Letter 8