Dear Auntie Helga,
Recently I moved back home with my mom with the lack of jobs where I lived. It was nice to be with my mom and enjoy her cooking again. Last weekend we were looking at old pictures from when I was a young boy. There were several pictures with a little girl in them so I asked my mom who was the girl. That was when I learned it was me. Yes, that is right, my mother liked putting me in dresses as though I should have been born a girl. I wanted to know why my mom put in dresses.
She explained her mother did the same thing as a way of turning on a boy's feminine side to help them deal with girls later on. I thought it was a dumb idea until I read about how common it was in other parts of the world. My mom proved her point by showing me dresses in her closet. She asked me which one liked and why. I picked one out then let her know why I liked that one. My mom then asked me how I gained the skill of knowing what dress looked the best when I never wore a dress before. She had a good point which is when my mom pointed out the reason. She said I was attracted to the material because she saw me feel the dress, the color and probably wondered if it looked as good on her. Some of what I did without thinking was what she did when she bought the dress along with other things only my mom would know.
The my mom surprised me by asking if I wanted to try on a dress again. I said no thanks. My mom was sure the thought of wearing a dress was still buried in my head. I left to go to the bathroom. When I came back my mom had picked out an older dress she wore before weight loss. My mom pushed me to try it on for old time's sake.
Finally I agreed to try it one time. My mom asked me to strip down so she could help me just like she used to when I was little. I rolled my eyes before taking off my pants and shirt. My mom said socks too and then she handed me a pair of her panties followed by trade you for boxers. I hesitated but my mom was persistent. It was clear to see my mom was having fun. She put one of her bras on me and a girdle with garters for stockings. In a few minutes my mom had me wearing her dress. She was full of compliments as it reminded her of the past. I wore it for a while until I talked her into pulling the zipper down on the back. My mom unhooked the bra and then helped me with the girdle which left me standing there in her panties. I traded her undies again then went to put in my shorts.
While watching TV with my mom she asked me if she bought me a dress, shoes and undergarments would I wear them like I used years ago. I just said that would be silly to spend the money on that stuff. A few minutes later my mom tried again almost begging me to let her dress me. I waited a while and just before she asked me again I agreed to let her have fun at my expense.
Before bed I went on the internet to see if other mothers dress their sons and was surprised by how popular it was in the UK. Hours later I found your website through a link posted by a mother. Auntie Helga I am writing to you to understand why mothers do this with their sons. If my mother decides she wants me to dress in feminine clothes all the time would that be normal? This is forward thinking but what if she decides to petticoat train me?
I could use your experience to help me here if you don't mind.
Thank you for your letter Sean. What a delightful childhood experience and thank you for sharing that with me. Obviously this was very meaningful to your mom as well and she wishes to re-live it in some way.
Its not unusual for a mother to share this with her son, your mother's motivations are her own and I really couldn't say, but I will say its more common than most people think. She may well decide to petticoat you but don't be concerned about that right now.