Dear Auntie Helga,
I am writing you a letter today that is not quite the same as most letters on your website. You see I am not a sissymaid and will never be one yet I have a relationship with my mom worth sharing with others. Let me share some history before I begin and yes it will be very short. Both my sister and myself lived with my mom all our lives never knowing our father. We found it hard at times however rewarding because of how close we were growing up with only a mom as a parent. For my sister and my mom it was more normal than for me since boys usually bond with their mothers but also have a need for a father. My mom was very good at teaching me what boys need to know and I learned how to be nice to girls and my mom unlike some school friends. My sister and I were very close and very rarely argued at all.
One day not long ago my sister was killed by a stupid driver on her way home from work. Needless to say with our closeness it destroyed our once happy family over night. Death always affects a family and usually over time people mourn then get on with life but never forgetting the ones who passed. What happened to my mom was deep depression followed by doctors appointments and all kinds of drugs none of which worked. My mom went from a very happy woman to one who stayed in bed all day and night. I did all the cooking, cleaning and also the laundry for my mom. One of the doctors talked to me along one day offering some ideas on how I could help my mom. Some of the ideas didn't work however the theme for most was to find a way to get my mom back into doing the things she loved to do.
My mom loved to shop and do anything with my late sister. They went everywhere together and it was always clear how happy my mom was to have a daughter. I began reading about mother and daughter relationships which took me to mother and son relationships. I learned the differences and one day stumbled onto something I thought was weird at first. The website called it mother and daughter/son relationships which was more like crossdressing with your mother. At first I thought it was a crazy thing for a son to do with his mom. What I noticed in all the pictures was happiness by both mother and sons. It wasn't forced but instead it was something they shared together.
Over the week I read more and more thinking what would my own mother think if I had the guts to talk with her about such an idea. Before I was ready to talk about it I had to be sure opening my mouth was a good idea. In other words what if she thought it was a bad idea and she thought less of me. What if she liked the idea but I changed my mind or got cold feet. I remembered my mom used to dress my sister and me then play with us. Oh by the way she dressed me in my sister's clothes when we were much younger. So what I did was talk with my mom about a dream I had of when we used to play together just to test the waters.
The next day I shared my dream with my mom who was embarrassed that I remembered her dressing me up like a little girl. I didn't remember all the details but I do remember wearing a dress with my sister beside me. My mom explained why she did it with me and hoped I wasn't angry which I wasn't. For some reason I asked my mom if she wanted to do it again someday. My mom looked at me confused when I explained a website I read about mother and sons dressing as daughters. Considering my mom was mourning my sister and I was offering to do something with her that they used to do together somehow it clicked. I showed my mom the website and how the mothers looked with their sons dressed as girls. At first my mom thought it wasn't possible but as she looked and read it became clear it was real. My mom asked me why I wanted to do dress like a girl and why with her. After reading it made sense to me my mom was missing my sister or female companionship. I would never be able to replace my sister nor was I trying to do it. Somehow inside I felt it was possible for me to make a difference in my mom's life, the woman who did everything for us and never asked for anything in return.
One thing about my mom was she asked me every day a few times if I was sure I wanted to try it and if I wanted to back out it was okay with her. We talked so much about her ideas and my ideas then agreed to get started. We went shopping together to buy me the basics first and even on the way home my mom asked me if I was sure and if not the items could go back. I wanted to go as far as I could thinking of my mom all the way and less about myself. I started to dress like a girl at home as my mom bought me more and more. At first we thought of dressing at home only but quickly realized my mom wanted me more than just at home.
She talked with me every night about the website we read about showing moms and sons out on the town. I agreed to try that out when my mom thought I was ready. So my mom bought me an outfit with the plan of me wearing it when she thought I was ready. My mom taught me how to be a girl so shaving my legs, underarms and wearing makeup every day became a normal thing for me. My mom wanted me to experience everything a girl or woman would experience at home first. My mom taught me to walk in heels and how to carry myself. One night we went out for a drive in the car with me shivering in fear beside her. With me wearing a wig and makeup a car beside us would have to look twice to know I wasn't a girl so my mom told me.
As time went on we started to go out for walks at night and into low traffic areas to get me used to being outside. At home each night my mom would ask if I wanted to stop or keep going. The looks I got from her when I got ready every day and seeing her out of the corner of my eye I knew I couldn't stop on her. We continued with me going out every day or night with my mom of course. It got to the point my mom asked me just before I asked her how far we wanted to take this change in life. The good thing about having an open relationship with your mom is honesty. My mom went first letting me know how much I had helped her deal with the loss of my sister and how grateful she was for me to make such a sacrifice. My mom wanted us to continue and look at the future with me as Wendy and not Nick. We had read about boys turning into girls from hormones and surgeries. It was clear my mom was liking the new me and I was also liking seeing my mom happy again. I wanted my mom to know I wasn't trying to replace my sister but instead offer her a chance to have a feminine son or a second daughter to share her life with again.
We both agreed to go further so I gave up all my old Nick clothes and only dressed as Wendy at home and outside the home. My mom assured me she was going to help me become Wendy if I wanted to do so. One thing my mom had not done up until that point was put any pressure on me which I was grateful for however it was about to change. My mom made an agreement with me if we were to go further it was going to be a more permanent thing. Up until then my mom had always offered me a way out and encouraged it if I thought it best. My mom changed to telling me if I started on hormones or had any kind of surgery other than laser treatments there was no turning back. My mom explained herself to me wanting me to understand how difficult it would be for me to be Nick then Wendy then Nick after losing my sister. I agreed with my mom which she was pleased to hear.
Later that week we went to see the doctor about options for me which included hormones and or surgeries. The doctor was very interested in my answers to her questions and wanted to be sure it was my decision. By the end of the appointment we all agreed I would continue to dress as Wendy for a little longer just to be sure it was what I wanted and what I thought it would be. My mom took me to have my hair done since I always had long hair as a guy. It was weird sitting with my mom in a salon having her tell the girls what she wanted for me. My mom had always trimmed my hair at home so this salon thing was different to say the least. I liked the results and loved not having to wear a wig any longer.
A few days later I started to have leaser treatments to rid myself of the hair and to get away from shaving so often. My mom continued to support my decision and helped me become more feminine. I never knew there was so much involved to be a girl until recently. What I did learn was how much my mom missed having my sister here with us. My mom continues to teach me everything and we continue to spend more time together than I did as Nick.
Last weekend I met a few women friends of my mom's who were also out shopping. My mom taught me to be calm and not worry if and when we met neighbors or friends. My mom always did all the talking explaining I was transitioning and she was helping me become a young lady. In most cases it went well and for those couple that it didn't no big deal my mom said to me. My mom was always good about letting us kids know not everyone can be our friends and in some cases we don't want certain people as friends. That applied more now than before.
I'm scheduled to start taking hormones very soon and have decided to stay as Wendy for my mom and for me. My mom slowly got back to being herself not ever forgetting my sister but learning to live with the memories. I am still learning to be a daughter with my mom helping me every day. We joke around like we used to with a girly twist which is fun. It's not a Mistress and sissymaid relationship however it is one of love and we are very happy with it finally.
Auntie Helga I have to thank you for helping me along the way and convincing me it was the right thing to do for my mom and for me. Although I will never be a sissymaid or my mom will never be a Mistress we are both happy thanks to your guidance.
Lots of love,
Thank you for your letter Wendy. What an auspicious start, her happiness is obvious and I am just so proud of you for putting her needs before your own, it was after all your idea to try to help your mom recover and have some hope again, it worked beautifully. Really well done Wendy.
I feel that if you give this some time, you will get used to wearing the clothes, then the real work begins, becoming what she wants, a daughter, this is an amazing sacrifice on your part and I know she knows that and really appreciates it.