Dear Auntie Helga,
I hope you can offer me some advice with the situation I now find myself in with my mother, given your knowledge and expertise in petticoating and sissymaids. I have been a keen reader of your website for the last few years and noticed you kindly offer counseling to both women and men alike via e-mail, so I hope you will spare me some of your time to help me. In exchange, please feel free to publish my letter or any future correspondence between us on your website if you deem them publishable.
I would like to tell you a bit about my background to begin with before I get onto what I want your advice on, so you can get a better understanding of my life as it is at the moment. I am 18 and I finished high school last summer and I am taking a year out to decide my future. My parents split up when I was young and I was actually brought up by dad, because at the time my mum suffered from mental health problems and addiction issues. Thankfully she eventually recovered and got over her troubles. Once she had, I was able to visit her and ultimately stay at her home at weekends and during school holidays.
Fast forward to a few months ago to cut a long story short, my life with my dad was turned upside down when he told me he had earned a big promotion within the company where he worked, but he would have to move abroad to take it. He told me he couldn't turn it down, as it came with a much bigger salary and could derail his career if he didn't take it. He wanted me to come with him, but said he would understand if I didn't want to. He then gave me some time to think it over. To tell the truth, I didn't like the idea from the start. I was happy for my dad, but I didn't really want to move to a foreign country with a different language. But the main reason I didn't want to go was because of my mum, as I wanted her to remain as big a part in my life as possible, and she probably thinks the same about me. Well, I know she does.
I phoned her to tell her the news not long after hearing it myself. We talked about it for a bit, and then she surprised me by asking if I would like to come and live with her or at least consider it as an option. I told her I would before finishing our conversation. I then went back to my dad to tell him about mum's offer and he told me as I was now an adult it was up to me what I wanted to do - he wouldn't stand in my way whatever I choose. But he did warn me that I would have to be careful around my mother, as there is always the possibility of a relapse with recovered addicts, so I would have to be on my best behaviour at all times, to obey all her rules and not to cause any sort of trouble, so not to put too much pressure on her or stress her out in any way. I understood, but told my dad I would like to move in with my mum, as I really wanted to get to know her better and to try to make up for all the things we had missed out on during my childhood and this was the perfect opportunity to do that.
She was thrilled when I told her, and less than a month later I moved in with her permanently. Given my previous stays with her, it didn't take me too long to settle in living with her for the first time since I was small. She didn't live too far from where I used to live with my dad, so it was not too much of an upheaval for me.
We got on great for a few weeks with me being careful not to stress her out too much and obeying whatever rules she had, until she told me that she had been on my computer when I was out one day and had checked my browsing history and found I had been visiting your site along with some others I won't mention here, but needless to say they are the kind of sites you don't want your mother knowing you visit. I usually erased my browsing history from my computer, so I guess it was partly my fault. I was of course angry and upset with her for doing that and bit surprised she was more tech savvy than I thought she was, even though I should have known better as she had her own computer, but she told me she simply wanted to get to know me as much as possible and to see what kinds of things I was interested in and what I liked reading about and watching, and so on. She sounded genuine, so I forgave her, not wanting to upset her too much, because of the reason I mentioned before. I simply told her not to invade my privacy again, and to ask me in future if she wanted to know anything about me or my life she didn't know about, rather than go behind my back.
She agreed and we both moved on, until a few days later when we were sitting together watching TV when she asked me about your website and why was I interested in that particular site; telling me again she simply wanted to get to know me better and was just curious. She told me she was open-minded about such things and didn't judge. She went on to say she wanted me to be open with her and to trust her to keep my secrets, as it would be just be between us.
Not wanting to upset my mum any further and to open up and be honest with her like she wanted me to be, I decided to talk to her about it. I told her I was interested in and had fantasies about being petticoated, becoming a sissymaid and serving somebody as such. I thought so, she told me. It seemed she had been browsing your website the last few days and had been reading all the letters and learning all she could about petticoating and sissymaids
She then shocked me by asking if I would like her to petticoat me and serve her as a sissymaid and for her to become my mistress mother. Before I could reply, she told me it could be something we could both explore together if I wanted, for us to become closer as a result and in a way start again in life as mother and daughter, to put the past behind us and start afresh with a second chance for her to be my mother and to 'bring me up' as a girl, and teach me everything about being a woman. She told it would be a chance for her to make it up to me for missing out on my childhood as my mother, and for me to explore my fantasies in a non-judgemental environment. She concluded by saying she just wanted me to be happy, and that she would do anything to make that happen.
I was very surprised by what she said. She had clearly set her heart on petticoating me having read your website, and reading about the other success stories mothers had had turning their sons into their sissymaids. I then asked her what she had in mind exactly for me. Well, she replied, I would like to explore everything, so we both get the full experience - her as mistress and me as a subservient sissymaid. She would teach me everything about looking after the house and her, including cooking, cleaning, doing the laundry, and some private things I won't mention here. I would be dressed in a full sissymaids uniform when carrying out my household duties including make-up and high heels, when not in my uniform I would be in full feminine dress still, even when I went out. I would be fitted with a chastity device, which would be permanent, so no more masturbating, as she said all sissymaids wear one and I would not be an exception. She told me I could seek relieve through anal play instead and that is something we could explore together if I wanted. She went onto to say, I would be completely subservient to her at all times, to do whatever she asked without question and to never answer her back. She finished up by saying she wouldn't be too strict in her role as mistress, as she wanted me to enjoy being her sissymaid and serving her, but there would be a certain level of punishment if I disappointed her in anyway. I asked her what. She replied having me over her knees and spanking me until I begged her to stop and/or cried. I simply replied, ok.
She had clearly thought all of this through thoroughly, I thought to myself. She then asked me if I wanted anything specifically if I agreed to become her sissy maid, and that she would do her best to accommodate me, as this was just about me as her. I though for a moment, and simply said I would like some say in not what I wore, but the general style of it, which she agreed to, but said the final decision would always be hers as mistress.
We left the conversation there more or less, with her telling me to think what she had said over and to take all the time I wanted to make a decision either way. That was a few days ago, and I am still trying to make up my mind as what to do. Having been a keen reader of your website for years, I know many of your male readers would jump at the chance to be a sissymaid to the woman in their life, be it a mum or wife, and I am perhaps looking a gift horse in the mouth, so to speak. I just don't know if am a true sissy, having never worn women's clothes before, or not.
That is what your advice on. What should I do? Am I a sissy or could I become one with my mum's help? Am I just being selfish and not thinking enough of my mother's feelings in all of this? I truly don't want my mum to relapse into her old ways and to please her in all things to avoid that, but some doubts still remain in my mind. I have learnt, through reading your website, all males are inferior to women, so any advice you can offer me would go a long way in helping me make a decision. I have told my mother I am writing to you and she said that was a good idea. She also told me she might write to you herself one day if I agreed to her petticoating me.
I'm sorry for the length of this letter, but I feel better getting my thoughts and feelings out into the open. Thank you for your time.
Thank you for your letter Mark. I will do what I can to provide advice that might be useful for this opportunity. I am so sorry to hear about your mother's issues but she seems to have turned the corner and is now ready to start a new chapter, for herself and with you. Becoming her sissymaid is a very large step to take and one that you both obviously are giving a lot of thought to, that's the right way to start, honest conversation and research.
Now she seems to be ready to begin training you, a wonderful opportunity and a very special way to live. You don't have to be a sissy to do this, you only have to be willing. I fully support you becoming her sissymaid.