Dear Auntie Helga,
I am not sure how much detail to share with you about tonight so if its too much please advise me. My aunt had called me before Barb came home to give me some instructions. Her concern was Barb might not have been ready to hear my story or not willing to continue with me. My aunt encouraged me to be honest so regardless of the outcome I would have tried my best. I listened to my aunt as always which helped me prepare myself for talking to Barb. Later when Barb did come home I did take her bags and coat putting them away for her. While I worked on dinner she talked about her day and that she had done some shopping at lunch. She continued talking while I cooked and once again she brought up shopping as though I was supposed to ask what she bought. Normally I never asked just in case it was personal but this time it looked as though she wanted me to ask so I did.
Barb started to talk to me like there was some big secret or like I was going to talk to her about tonight. She reached into one of her bags bringing out a bra and panty set asking me what I thought of it. As usual I always said it was nice or I liked it so this time I said the same. Barb confirmed with me that I liked it so again I replied that I did. The set was beige with lace and small ribbons so what was not to like. Then Barb gave me a hug whispering in my ear she bought them for me as my heart stopped. She went on to tell me that she felt I would like to wear matching bra and panties like she does because I told her a few times they looked very nice on her. I wasn't going to lie or freak out when later on I planned to share with her my own secret. Barb told me she noticed I shaved my legs and underarms which was a feminine thing to do. She asked me if I would at least try wearing panties for her which I agreed to do. Some how I was thinking she had already talked to my aunt.
There wasn't much talk about it while we ate dinner until later on when it was my turn. Relaxing watching TV we talked about our younger years like most couples do getting to know one another better. I asked Barb if I told her something that only my aunt and late mother knew could she keep it a secret. After she agreed I told her all about when I was younger my mother dressed me like a little girl, only at home though. Barb asked if I was kidding when I went on to say that my mother kept that up until she passed away. I shared that I was 24 then as Barb looked at me trying to put the pieces together. Calmly she asked if that was why I shaved my legs and underarms which I was used to doing. Barb asked what types of clothes was I dressed in by my mother which is when I let her know about being a sissymaid.
Barb taking all this in asked a number of questions which I answered before she asked was I kidding her. I told her that I spoke the truth and it was my mother's wish I find a woman some day to serve as I did for her. Barb asked me if this was my plan meeting her when I replied not at all. In fact I had discussed my feelings for her with my aunt who was going to tell Barb if I didn't. Barb hesitated as I wondered if she was going to leave or freak on my head but instead she asked me to show her my sissymaid clothes. In the house there is a door behind a door so to speak that leads to my closet. If you weren't paying attention or looking for it most people would walk right by it like Barb did many times. I opened the door turning on the light as I saw Barb's eyes looking at my dresses and shoes all lined up on the floor. She knew then I wasn't lying to her. Barb looked in the drawers seeing my bras, panties and stockings, then at me.
We went downstairs to talk about it more with Barb asking why I didn't tell her sooner. I admitted wanting to however my aunt suggested I wait a little longer but not too much longer. I also explained feeling bad that it wasn't something I could have said the first time we met. Barb wasn't angry but wasn't thrilled either as she took it all in. She asked me what it was like to serve my mother all those years when I admitted it was good so she started to understand that it wasn't abuse. I told Barb that my aunt was in charge of me from the time my mother passed away and still is today. Barb wanted to know how that all worked so I said that my aunt would like to come over and explain it when Barb was ready. She was somewhat confused however not angry and wanting to hear more so I called my aunt.
They talked on the phone for a while then Barb hung up telling me my aunt was coming over now. I asked Barb if she was alright which she was thankfully. We talked about what my aunt said to Barb on the phone which was assuring Barb it was going to be better than alright. Barb was smiling as we sat arm and arm waiting for my aunt to arrive. Shortly after my aunt walked in so I got her a drink so we could all talk together. My aunt had other ideas so she sent me to get ready for Barb to see her new sissymaid. She told me everything except makeup so I curtseyed then left the room. I heard Barb ask my aunt if I curtseyed to her when my aunt replied certainly.
Although I had been my mother's sissymaid for many years I found myself being nervous all of a sudden. I could hear a few OMGs from Barb with some laughter so I felt it was going to be alright for her which was my concern. It was time for me to go back downstairs and face the music so they say. Before walking in the room I curtseyed to my aunt again then walked up to her for inspection. As I turned around I could see Barb's hand over her mouth while my aunt talked to me showing Barb how to talk to a sissymaid.
I sat on a chair in front of them while my aunt gave Barb the tour with Barb commenting as my aunt told her everything. In a nutshell my aunt shared with Barb how wonderful her life could be now. My aunt told Barb I had been trained over the years to do everything from cooking to cleaning and that Barb would no longer have to do it. To show Barb my aunt was in control of me she sent me to get one of my chastity devices. When I returned my aunt pulled my panties down then proceeded to lock up my penis in front of Barb then passing her the keys. My aunt pulled my panties back up then asked Barb what she thought now. Barb asked me if I wanted her to be my Mistress like my mother used to be. I replied yes Mistress I do. She asked if I would dress like this for her everyday without any complaints when I again said yes Mistress anything for you. I could see in Barb's eye that she was starting to like the sound of this already.
Barb asked my aunt what about sex with the chastity thingy on when my aunt said it was all up to her now. She advised taking it off for sex or good behavior while the rest of the time keep me locked up to avoid me playing with myself. Barb asked me if I wore makeup sometimes too when my aunt said when at home always in makeup. Barb replied wow many times as my aunt told her everything I can and would do for her. My aunt went upstairs to talk about my clothes, wigs, shoes and nightgowns so that Barb had a good understanding of her role and my role.
When they walked back in the room I stood up to curtsy them. My aunt was telling Barb if she had questions to call her or if I caused any issues to also call her. With that my aunt left us alone which was awkward for a few minutes as I stood there ready to serve Mistress Barb for the first time. Barb told me to sit with her while she asked me all kinds of questions just to be sure I was going to be alright with this now that my aunt left. I assured Mistress that I was going to be fine as this wasn't that new to me. Mistress looked at me telling me I kind of looked cute and she liked the look. She asked me what I thought about the chastity thingy on my penis. I let her know I had worn it many times before when my mother was alive. Mistress said my aunt strongly suggested to keep it on most of the time except on nights when we had sex so I agreed to wear it for her.
Mistress told me my aunt took home most of my guy clothes and underwear so from now on I was to only wear my sissymaid clothes. I admitted not even seeing her leave with all of it when Mistress laughed asking what did I think they were doing upstairs. Mistress asked me if I really knew how to clean, iron and cook everything when I replied that I did. Mistress let out another wow Jackie that is fantastic. She told me that my aunt assured her that I would be a sissymaid for life if Mistress wanted to think of marriage I would make the best partner. Mistress asked me if I ever thought of being a sissymaid for life when I admitted knowing that for many years now. Mistress admitted to me not knowing much more than my aunt told her tonight however she was willing to try to make it work. I let Mistress know I would try also to make it a great experience for her too. I asked Mistress was she sure that it was going to be alright with me as her sissymaid. She explained it was a bit of a shock but she did like my look and could see getting more used to it especially in makeup. My aunt suggested to Mistress that she start feminizing me again as my mother had done. Mistress went over a few things with me about my nails, eyebrows and hair to show me she did in fact talk to my aunt. Mistress also went over some of what she wanted me to do in the morning as I started my life as her sissymaid.
Mistress left the room returning with the bra and panty set she bought me. I took off my clothes in front of he then tried on the new items so she could have a look at the fitment. Mistress then asked me to put my dress back on for her. I could see she was getting used to telling me to do things that might be humiliating and to get used to showing authority. Mistress asked me a few times if I would do anything she demanded when I replied yes as she shook her head with disbelief. She asked me what happened when my mother was alive if I refused to wanted. I let Mistress know my mother would use the belt on me or have me stand in the corner for hours on end. Mistress asked me why I kept living as a sissymaid when my mother passed away when I let her know my aunt kept an eye on me. I also told Mistress that my aunt wouldn't hesitate in punishing me if and when necessary. Mistress asked if I was afraid of my aunt when I admitted yes I am. I showed Mistress the petticoated.com website as we read letters together. By the time we were finished Barb was starting to feel pretty good as a new Mistress. She went to talk on the phone to a girlfriend which could last for hours so I asked permission to work on the computer.
I can hear Mistress telling her girlfriend all about me and my clothes, then I hear laundry and cleaning. Oh well Auntie Helga my sissymaid life is in full swing again just the way my aunt likes it. Tomorrow my day looks pretty busy while Mistress does Christmas shopping. I hope all this didn't bore you to tears Auntie Helga.
Thank you for your letter Jackie. Not bored at all, I enjoyed reading about you and your rather awkward conversation with your girlfriend now Mistress. Fortunately your aunt, a delightful and resourceful person did what family does best, helped you to continue in service to a strong and confident woman. Best of luck and please do write again some time.