Dear Auntie Helga,
I found your website with the help of my wife Dee. We have always had an open relationship so sharing websites of interests to one another is considered normal. Dee sent me a website to check out where men were wearing skirts and high heels. She thought it would be fun for me to try that too. We talked about it then decided to try something unisex first. I wore slacks and shoes that looked more feminine than anything else I had worn before. Dee wanted me to loosen up and try a skirt with heels, something low so as not hurt myself. I agreed to go shopping with Dee and try on a few skirts then a few pairs of heels. By the end the afternoon I had 2 new skirts and 2 pairs of heels. Oh yes pantyhose to go with them. I tried them on at home and Dee insisted I wear some panties she bought when I wasn't paying attention. Anyways I wore the skirt and heels at home for about a week, Dee wanted to go out for a walk with me in a skirt and heels. i was scared but went along for the ride. Dee walked me through how to walk in heels which I had no idea. A couple of young girls walked passed us chuckling to themselves after seeing me in a skirt and heels. Dee assured me most people would not pay attention since more and more people were coming out today.
A week later Dee wanted me to try on a bra she bought me with some forms. I was puzzled as to why she wanted me to wear a bra. Dee told me to go with the blouse she bought me to wear. She showed me pictures of women with a shapely figure and some that were skinny with no boobs. Which ones looked better she said to me. It was obvious the women with boobs looked better wearing blouses. I put the bra on while Dee went to get the blouse. It was vert pretty and see thru too. Dee put a camisole on me then the blouse. Once it was all tucked in I could see why Dee wanted me to wear a bra.
For the next few weeks Dee wanted me to wear blouses and skirts at home. She told me she had an idea but wanted me to get used to wearing a change in clothes from what I had always been wearing as a guy. We also read about petticoating as Dee wanted to learn more about it. Dee asked me if she bought me a pretty pink dress would I wear it for her. Pink was not a color for me but Dee bugged me so I agreed. Before long the dress arrived except it was a sissy dress. Dee was quite pleased about how nice it looked and wanted me to try it on with the new white heels she bought me. I didn't like the pink dress with all the lace on it. I thought Dee had gone too far but she liked it.
Dee made me wear only women's clothing for a month as in every day. She helped me learn to walk in heels more like a woman. It was Dee's goal to feminize me as much as possible. I had to wear a wig every day too.
Auntie Helga has Dee gone too far? I have been a good sport all along yet Dee wants more and more. How do I handle this?
Thank you for your letter Puzzled. What a wonderful marriage and so far things have gone splendidly so I see no need to alter the direction, while I understand your confusion, in my opinion she has not gone too far and to make her happy at this stage I would suggest you continue what you have been doing, obeying her.