from Randi

Dear Auntie Helga,

Ever since I was in my teens I liked reading about women who dressed their boyfriends and husbands like girls. It wasn't until I got married that I talked about it with my wife. We looked at men and women who liked kinks before anything actually happened. I showed my wife a couple who were married like us and the guy also had breasts showing in his dress. My wife was always a good listener as I shared myself with her in more detail than I thought. After a few months of talking and looking my wife asked me what I wanted to do and when I wanted to do it. I let her know I wanted to dress like her and go out with her as a couple if she thought I could pass.

Caroline wrote things down and asked me a few questions as though she was interested enough to make it happen. She told me it would be a lot of work for me to look like a woman but she felt she could make it happen. Inside I was excited and also a touch scared to think all what I read about others might happen to me too. Caroline looked up at me then asked if I wanted to have breasts or wear fake ones. My heart skipped a beat when she asked me that question. I played stupid then asked how I could have breasts. Caroline said she read about the one couple we looked at where his wife bought him pills to get the breast process going. I asked Caroline if she would want me to go that far. She looked at me then said why not if I wanted to dress the part why not be the part. A few weeks later Caroline showed me the prescription she ordered so I took the pills every day. I shopped with Caroline and my wardrobe began to grow as I only wore women's clothing Caroline bought for me at home. She taught me about mixing and matching clothes and taught me about makeup.

Caroline took me out for the first time a few months later which turned out to be a weekly thing. Some people knew I wasn't a woman however Caroline didn't care. She was careful where we went and when we went there to keep me safe. Caroline always took me in women's stores where she felt I would be safe. A few months later she noticed my breasts started to develop one more morning. I had felt something but never noticed the changes. Caroline was happy to see the results of me taking the pills every day. It took months before anything happened but once my breasts got started they grew at a steady pace month by month. About a year after I took my first pill I had no choice but to wear a bra since there was no hiding my breasts anymore.

It wasn't long after that my penis acted up when we made love. Caroline told me the pills were responsible for my breasts and my penis. I wanted to stop taking the pills but Caroline told me it was not a good idea and would not correct my penis troubles. By the time my penis stopped having erections my breasts had grown another cup size. Caroline told me my body had stopped fighting the pills which allowed them to work even better. I was concerned I went too far however Caroline felt it was what I wanted so it would all work out in the end. I looked more feminine than before so Caroline helped me find colors and styles that looked best on me. She told me I was going to live this way for life so best I found what looked best on me. Caroline also let her friends and family know I had decided to transition and she supported my decision. Slowly Caroline invited people over to see me and those that accepted me stayed in our lives and those that didn't accept were gone.

Caroline got a new job with more responsibility so I stayed home to become her housemaid. I learned how to cook, clean, sew and do the laundry. On the weekends we went out for dinner and did the groceries together. I never wanted to be the housemaid at the start. I just wanted to wear women's clothing and share it with Caroline. I learned over time she wanted to embrace it and more. It was like Caroline wanted something back for her acceptance of me dressing as her girlfriend.

Auntie Helga, now for my questions if that is ok. Caroline talked to me about having my penis and testicles removed to help me feminize more. It was something that shocked me and I blamed myself for getting in to this perhaps too deep. Caroline showed me a guy who had it done with and without panties. I agreed he looked better without a penis and testicles but then again it was him not me. Caroline told me the changes in my body are not reversible so I was going to have to dress as a woman and never like a guy again.

Auntie Helga is this something others have done and if so what was the outcome? Caroline wants me to be more feminine for her.

What do you suggest?


Thank you for your letter Randi. What an amazing relationship and I would love to read more about that at some point but in the meantime, let me get to your question.

First, thank you for the background, it helps put this in context. It seems to me that she is making your fantasies come true, the old 'be careful what you wish for' situation comes to mind. She is obviously enjoying taking the marriage in this direction and I don't personally see any problems.

Many others have had this small corrective procedure and with great effect, pleasure in serving their wife, becoming more feminine in body and mind, no real need for those things anymore anyway. I suggest you agree and become the feminine maid she desires.

Love to hear what you decide... Auntie Helga

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