from Stevie

Dear Auntie Helga,

I am quite embarrassed to send you this email today with not knowing how to resolve my problem on my own. You see it was my birthday on Saturday with my girlfriend buying me a couple of gifts to open here at home. She was more than excited which is the way she is with gifts whether receiving or giving. When I opened the first one I thought it was a joke seeing several pairs of pink panties. Me thinking Arlene was playing a joke on me I thanked her asking how she knew I wanted pink panties again as a joke. The next box was heavier so I opened it hoping it was something I wanted when I saw 3 pink molded cup bras and silicone breasts with nipples on them. I was getting nervous and not feeling the same thrill as Arlene. It was clear she was thrilled, all smiles and showing excitement. I thanked Arlene with less enthusiasm as she handed me another larger box and me feeling afraid to see what was next. When I opened it there was more pink with this lace covered satin dress and a pair of women's high heels. By now I knew what Arlene was planning as we had talked about sissymaids last summer once. Arlene held the dress up to me with me turning all shades of red and finally asking what was going on.

Arlene told me she wanted me to be her sissymaid and knew if she asked I would have said no which is why she bought me the gifts. Arlene begged me to be her sissymaid even if it was just for fun. I wanted nothing to do with it as she begged me over and over to say yes to her. Arlene pulled my pants down proceeding to give me the best birthday blow job I would ever ask for. When she was done the begging started again with her wanting me to go have a bath with her. I thought okay why not have a bath and maybe another blow job. In the bathtub Arlene started shaving me and I mean shaving all of me telling me to life my arms and turn around and finally shaving my pubic hair while giving me a hand job. When she was finished I cleaned up the bathtub when Arlene returned with another small gift to open while I was only wearing towel. In the box was a stainless chastity device of which Arlene went to work fitting on my penis. With the click of a lock she had it on in a few minutes smiling at me pulling on it. I knew what was next as she guided me back to the living room where my gifts were waiting. Step by step Arlene started to dress me going to get stockings and a garter I hadn't seen yet. Before long I was standing there in my new birthday gifts with Arlene chuckling at my appearance. I asked if Arlene was happy when she smiled telling oh yes very happy.

Arlene went on to talk to me about her dream of having me as her sissymaid and all the reading she did over the past few months. I had no idea what it was all involved until Arlene shared her plan with me of being her sissymaid so I would clean the house, cook her dinner, wash the clothes and iron them for her. My reward was to have pretty clothes as she called them and have her unconditional love. With me trying to figure out why the clothes and stupid heels Arlene showed me a couple of websites include yours Auntie Helga where many other women had become mistresses and their boyfriends and husbands became sissymaids.

When I asked why Arlene told me the way of the future is with women having more of a role both at home and in the work world. Arlene explained no longer are women put on this earth to cook and clean for men. When I asked what about how I feel about it all Arlene told me I was welcome to ask questions but it would be best I begin getting used to the shift of power. I asked Arlene about the clothes again when she told me the sissy dress is necessary to help train my mind since it wasn't going to be a natural transition for me otherwise. Arlene told me women have been doing this for years around the world so she was going to follow the same process with training me. Arlene went on to tell me every day I was to wear my sissy dress and work on assigned duties with her inspecting my work to ensure it was to her standards.

Auntie Helga as you can see I am now in a bad situation and don't see a way out unless I move out. Arlene has just in a couple of days changed me into her sissymaid and I am totally confused about why. I admit I learned how to run the washer and dryer and how to iron her clothes but I am not excited about these changes. We are getting married in a few months and I am not sure living as her sissymaid is for me.

What to do?


Thank you for your letter Stevie. I understand how confusing this must be for you right now and it came as such a surprise. She obviously wishes you to try this for her and really, what's the harm to do so for a little while.

I don't really see this as a bad situation but rather an opportunity to express your love for her by your sacrificing yourself to her desires. As to why she wishes you to become her sissymaid I couldn't really say and she may well not know all the reasons herself, sometimes we just want to try new things.

Auntie Helga

Return to Index
Letter 10