Dear Auntie Helga,
My wife and I like your website and always read the letters sent in by the readers. The other night we were talking about women who transform their husbands or boyfriends into sissymaids. One thing led to another as our conversation touched on some related topics when I asked my wife if she ever wanted me to be her sissymaid and her my mistress. She laughed letting me know lots of times except she knew I would say no way. Then I asked her how far she would go as a mistress so she answered all the way why not. I asked her if she would ever have me castrated which lit up her eyes like I hadn't seen before followed by oh yes. Connie explained that is a fantasy of all kinds of women.
I was puzzled not ever hearing anything like that before. We talked for a while when I asked Connie how she could sit there and admit to castrating me when we both loved sex so much. She smiled then showed me a clear slip on penis men wear when they aren't big enough or women don't want them to have any sensation. There was another one more like a strapon for guys to wear if they did have a penis or were in chastity. Once again I looked at Connie then shook my head after she admitted castration turned her on and so did a sissy husband. I said to her all this time we read stories together and I was just heard her fantasy. Connie laughed then told me I never asked her before so she never told me. All of a sudden the stories we read had a new meaning to both of us. Connie looked over at me then asked if I wanted to be her sissy.
I didn't say anything but my brain was working overtime. Connie sat down close to me grabbed my balls then whispered in my ear she wanted to cut them off. I said no way pushing her away but Connie came back again. She whispered in my ear how much she wanted to dress me up like a little girl in pink panties and a cute pink dress. I let her go on that time since she was determined to get me to say yes I could feel it. Connie was convincing except I wanted to think about it more.
A few nights later at dinner Connie made me aware she found a place who did castrations and she made us an appointment. I immediately thought she was kidding me except she wasn't. Connie held my hand then looked right into my eyes as she told me castration really turned her on. She told me how much our conversation turned her on the other night and she wanted me to say yes to castration and yes to being her sissymaid. I looked at Connie then told her she was full of it. She looked back at me then told me she wanted me to say yes and for me to give her my balls. Jokingly I asked Connie if she wanted to chop off my penis too.
We went to watch TV. Connie took my clothes off until I was nude then she took hers off. She took my hand and ran it all over her soft body and told me she wanted me to be soft like her. Connie told me she wanted to shave my entire body if I would let her so we went to the bathroom to have a bath together. Connie asked me if I was ready then she went to town and shaved all of me. While she shaved I played with her breasts and vagina which she had just shaved for me. When she was all finished we dried each other off then went in the bedroom. Connie took my hand then pulled me over to her side of the bed. She took out a pair of panties then put them on me. Connie pointed out how much I liked them by the size of my penis. She then put a bra on me and filled the cups with silicone forms. I was speechless as Connie continued dressing me more and more until I was stood there in a sissy dress.
Connie put a pair of heels on me then adjusted my stockings. She told me how much it meant to her for me to be her sissymaid and she knew I wanted it too. I thought Connie was done until she brought out a chastity device and a bag of ice. Before I knew it my penis dropped from the cold ice on my balls. I was paralyzed and just stood there while Connie put the chastity device on me. Next I heard there we go all done. I was dumb founded that a conversation led to Connie turned me into her sissymaid.
Connie talked with me about how much she wanted me to be her sissymaid and how she expected me to serve her well. She told me I was going to be castrated this week and possibly have my penis taken away too. I came to my senses then spoke up but Connie slapped me. She looked at me with a firm look so I knew to not challenge her decision. Something inside told me Connie was serious and I was going to be castrated no matter what.
For the next few days Connie showed me how to clean the bathrooms, wash the floors, vacuum and how to do laundry all while I was dressed as her sissymaid. The day came for me to go with her to be castrated and I was terrified. Connie told me in the car she loved me more than anything and I was going to have the surgery done to show her how much I loved her. Without my knowledge Connie had my medical records sent to the clinic so I wasn't there to talk about castration I was there to have it done. We saw the doctor, I signed the papers and took my clothes off to put on a gown. Connie took the chastity device off while I was lying on the operating table. I remembering her kissing me then counting to ten while I held her hand. It was hours later I woke up in recovery with some pain and then I was out until the next day. Connie came to see me the next morning as I remember her smile as my eyes opened. She kissed me then told me I did really well and it was all done. I remember asking what was done since I was drugged up. Connie whispered in my ear my balls and penis were removed just like we talked about.
It all came back to me as I teared up. Connie whispered in my ear I was her sissymaid just like we always dreamed. The next few days were quite painful at times until I began the healing process. Before long I was at home with Connie again. A week later I went to have the bandages removed and the tubes. The doctor told me I did very well and was healing well on my own. She gave me a prescription to have filled on the way home for Estradiol. I had no idea what it was until a few weeks later when I asked Connie how long I had to take them. She told me forever since I didn't have a way to make testosterone anymore they put me on estrogen to help me become more feminine. I was shocked and asked Connie how did we get from talking about sissies and castration to where I ended up.
Connie talked to me about how she detected I wanted to be her sissymaid and how much she wanted it to happen too. She told me how much she loved me and how much it meant to her I gave up my manhood to be her feminized sissymaid. I told her I was being sarcastic when I mentioned her taking my penis too. Connie told me I didn't need a penis when she wasn't going to let me use it anyways. I knew then our conversations were more than just talking, it was Connie's dream.
Over the next month I healed up completely as though I was never born with a penis. I felt the effects of Estradoil as it seemed to make me more submissive in nature. Connie booked me an appointment to have breast augmentation. She was determined to completely feminize me. By the time my breasts were healed I was the sissymaid Connie dreamed about and more than I ever thought about. Connie never became a Mistress like many we read about however she does control everything about me. I'm still learning how to be the sissymaid of her dreams. Connie took a liking to wearing a strapon and using it on me. I on the other hand took a liking servicing her orally 5 nights a week. Connie has introduced me to most of her friends as her sissymaid. Only a few of them know I have breasts and had surgery to remove my penis and testicles.
I give oral service those women on days when Connie is at work. Connie continues to explore other opportunities for me from feminization to servicing her. When I look back to the woman I married and the years we had as husband and wife the Connie I know now is more determined. We have talked about how many times she wanted to bring up me as her sissymaid. I remember those times too but for some reason she wasn't ready or I wasn't ready in her mind. One thing for sure the night I asked so many questions about sissymaids and castration Connie knew it was the time.
You can see by my story here she took action without backing down. Connie knew she had me and it had to be then of not at all. I never thought she would actually arrange for me to be castrated much less have my penis removed too. I learned a valuable lesson that night which was never underestimate a woman in any way. I thought of talking about castration and sissymaids just to see what Connie thought. Instead it was like a time bomb in head. She heard the words come out of my mouth and took action while the topic was on our minds. She knew a week later the topic might not be discussed again for months. I guess Connie wanted this for a long time but didn't know how to introduce it to me. One thing she did know was how to implement it. Connie never talks about me not having testicles or a penis as though I never did. She only talks about feminizing me more to help her with her dream.
Auntie Helga I hope you enjoy hearing how a loving husband and wife turned Mistress and sissymaid.
Thank you for your letter Sissy Malinda. What a wonderful introduction and thank you so much for sharing your story with me, the details of your exploration together are so good to hear, its obvious how much you love your Mistress wife.