Dear Auntie Helga,
My friend Lisa sent me a link to your website since she is kind of kinky for a 19 year old. I did read several of the letters from your readers and liked them. Now let me share my story with you then I may have some questions or you may have some for me. When I was younger I used to spend my summers with my aunt. It was a fun time for me to be with my aunt. We used to do things together even cleaning and cooking which is when I learned how to look after myself. Since it was only my aunt and me there she used to let me wear an apron when we worked in the kitchen. I was only 8 years old that summer so my aunt thought it would be fun for me to dress more like a girl than a guy when we did things around the house. It felt a bit odd to be with my aunt while I wore a dress or a nightgown. My aunt told me it was perfectly okay for me to wear girls clothes at her house but suggested I not tell anyone, even my mom. As I got older I missed the odd summer at my aunt's but ended up back when I could. My aunt would buy me clothes during the year so when I got there for the summer I would end up wearing young women's clothing all the time. My aunt made sure I had nice panties, bras, dresses and shoes. The summers were fun except they ended too fast. When I went back home I had to stay clear of my mom for a few weeks to allow my underarm and leg hair to grow back again. I got so used to wearing young women's clothing that at home I missed it. I talked with my aunt to see of she thought telling my mom would be a good idea or a bad one. In the end we both agreed to keep it as our secret.
Over the winter my mom passed away which was devastating for me to lose her so soon. At my mom's funeral my aunt suggested I live with her at least for a while since I had no other family members. It took a while to move all my mom's belongings to my aunts house but I finally got there. For the first few days I didn't wear any of my summer young women's clothing mostly since I was mourning. Then one morning I got dressed in a new dress my aunt bought for me. It felt nice to be back in my women's clothes again after shaving myself. My aunt was happy to see the dress fit me and that I was willing to continue wearing women's clothing. I always found it hard to explain to my aunt or even you now Auntie Helga why I like wearing women's clothing. My friend Lisa thought it was cool I like to wear women's clothing and thought I would make a nice sissymaid for my aunt or Lisa herself. That was something I knew very little about until I read some letters on your website. Lisa suggested that I let my aunt feminize me or for me to ask for a wig or to grow out my hair. Lisa thought it would let my aunt know I was interested in looking more feminine if I wanted to that is.
As I settled back in at my aunt's house we talked about me getting a job or did I want to work for my aunt. Since my aunt has a home based business she was willing to train me to answer the phones and do office work. I decided to work for my aunt that way I could continue to wear my dresses fulltime as long as I didn't have to see customers or answer the door. Some how my aunt decided to make me more feminine as I was to be her secretary. Within a few weeks I began to wear makeup, a wig while my hair grew and painted my nails. I felt more like a woman than her nephew all of a sudden. Since the job was only 3 days a week my aunt talked to me about being the maid the rest of the time. I knew I had to earn my keep so we talked about the maid thing one night. One thing about my aunt was details. If I was to be her secretary which I was I had to look he part. The same thing to be her maid so my aunt bought me two maid uniforms and maid shoes. I told Lisa how things were changing for me and she cheered me on. It felt good to learn something new and to have two jobs both as feminine positions.
Last weekend my aunt came home with a Holy Trainer because she caught me masturbating one night. My aunt was not happy so she bought the device for me to wear every day and night. I put it on reluctantly while my aunt watched. The next day I sent a text to Lisa who wasn't surprised I had to wear a chastity device. Lisa told me if we ever got together she would insist I wear one too as the world is changing where most women want their men in chastity. Meanwhile back with my aunt things settled down as we worked together every day with no issues. My hair and nails grew to the point my aunt looked after them as she used to work in a salon. Other than when I went to the bathroom I looked more like a woman every day. The summer came again so Lisa wanted to visit me to see how feminine I had become. My aunt agreed so a few weeks later Lisa arrived to spend a week with us. At first I was so embarrassed but Lisa was proud of me and liked my new look. My aunt gave me some time off so Lisa could take me away from the house which I hadn't done all winter. It was nerve racking to go out looking as a woman but not as one. Lisa assured me I would be okay as long as she kept an eye on people. We didn't go anywhere heavily populated though.
Lisa asked me if I wanted to be her sissymaid and if my aunt agreed to let me go would I. It was a hard decision because my aunt and I had history sine I was very young. I also worked for my aunt as her secretary and maid. Then I had to decide if I wanted to be anyone's sissymaid. My aunt never told me I had to be her sissymaid or I had to stay with her as it was just assumed. What would it be like to live as Lisa's sissymaid? We were very close friends but I never had to take orders from her before. Did I want to go back to my guy life and get a good job in the city. They were all questions I had to think about first before saying anything to my aunt or Lisa. The week ended so Lisa went home as we agreed to talk about a future but it would take time. My aunt put me back to work as her secretary and maid while in chastity at all times.
Auntie Helga have you seen guys become sissymaids for their aunts or mothers then to go off with another woman? What about me going off to work as a guy and losing my feminine side? Would I be happy? Would it be possible?
I would just love to hear your thoughts some time.
Thank you for your letter Kevin. Absolutely, happens all the time. Many aunts and mothers love to see their sissymaid son/nephew married to a dominant wife. It also happens that people change and drop their feminine side. I can't say if you would be happy but anything is possible. How about you try a week or so with Lisa or have Lisa stay longer at your aunts and take on a more dominant role? We would all love an update at some point.