SISSYMAID TRIAL
from Tiffany

Dear Auntie Helga,

I have liked your website and had an interest in petticoat training for a couple of years. It is something I never talked to anyone about not even my wife. A few months ago I lost my job however my wife got promotion a week later which saved the day. I helped out at home as much as I could without knowing how to do it all. The thought crossed my mind to ask my wife if she would allow me to be her sissymaid except I was scared. Sometimes in life we want something and when we get it the feeling isn't the same as what it appeared to be. I read as many letters as I could to figure out if I wanted to do it and how to share it with my wife.

One night while showing me how to work the washing machine the opportunity happened. My wife mentioned life with a maid would be a dream come true. It was then or never for me so out of my mouth came my question to her. I said what about me becoming her maid to take all the pressure of her. Linda laughed basically telling me I wasn't maid material. I tried one more time by letting her know if she trained me I would like to try it. Linda looked at me very weird then asked you mean like a maid maid. I replied close to a maid maid which is when I showed her the pictures on your website. There were a few OMGs as she looked at the pictures and the wheels turned in her head.

Linda asked me if I really wanted to wear women's maid clothing so I answered if she thought it was appropriate. She asked me a couple of times was I absolutely sure which caused me to put a disclaimer in the deal. Linda wanted to know what disclaimer as she rolled her eyes and laughed. I suggested trying it for a month which is when Linda's business negotiation skills took over. She did a few calculations of the cost of clothing compared to having a maid service then came back with three months. Linda convinced me three months was the break even for the clothes. We went back and forth until I agreed. Linda reiterated sissymaid and not maid maid right? I thought I guess so

Within a couple of weeks Linda had trained me how to clean, cook, do laundry etc. I became the maid she wished for the night I volunteered. Linda read all about sissymaids and training them. I found myself completely shaved, in chastity and dressed from head to toe like a well dressed sissymaid. The dream I had without ever telling Linda became true. I thought she would buy me a maid uniform, shoes and maybe a bra or two. Instead Linda transformed me into a real sissymaid right down to the stainless steel chastity cage on my penis. Linda taught me a valuable lesson which was be careful what you wish for.

The reason I sat down to write tonight was to thank you for your website for one. The other reason is to ask your assistance. You see Auntie Helga in two weeks my three month trial with Linda will expire. I might have an opportunity to land a job in my field but I haven't applied yet. Linda has never been happier having me as her sissymaid. She took to the Mistress role more than I anticipated. It's one of those things when I used to dream about a life as a sissymaid except I never knew how Linda would take it. Now only weeks away Linda bought me another sissy dress and a new pair of heels. As much as I enjoyed the experience and thanked Linda for helping me with my dream it might be time to hang up my dresses. My concern Auntie Helga is Linda is showing signs of extending my life as her sissymaid. For example the new dress and shoes. Also Linda pierced my ears on the third week which I thought why do that for a three month trial. I didn't say anything because Linda taught me to be her sissymaid as she was my Mistress. It was all part of when Linda said sissymaid and not maid maid. Somehow I felt Linda wanted to test me as far as she could within the agreement. She has done that too.

Auntie Helga what do you feel about sissymaid trials? Do you feel it was fair of me to volunteer for three months or do you feel once a sissymaid always a sissymaid?

Please be honest with me so I can be prepared to talk with my Mistress Linda.

Thank you,
Sissymaid Tiffany


Thank you for your letter Tiffany and thank you as well for your kind comments about my site. What a wonderful conversation with Linda, I'm sure she was surprised.

Thank you for the background info but let me get to your questions now. Like you did when this started I suggest you have an honest conversation with your Mistress and discuss what happens now, however this should be her decision it seems to me. Besides the employment opportunity, you also have the possibility of living out your dream and making your amazing wife's life so much better. I feel a 'trial' is a 'start' and only a trial in your mind because as soon as she experienced the benefits, she's sold and you are her sissymaid from now on, enjoy it.

Auntie Helga

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