I am writing to you today with an understanding that you wanted to meet me. This does feel somewhat awkward so I do hope that Jackie isn't playing a trick on me. According to Jackie she has been communicating with you about a recent turn of events here. Let me say meeting Jackie was not like most men I have met in my life. She was shy and not aggressive at all which to me was a welcome. It has only been a few months knowing her with very few surprises until the other day.
We all have something inside us that is private however hearing Jackie's story was mind blowing. You might think a boy raised as a girl then a sissymaid might be one of confusion when in fact Jackie is not confused at all. She is loving human being and now as my sissymaid even more so. I must admit this is so new to me that typing the terms her and sissymaid when I think of Jackie does seem odd. Her aunt gave me a quick education on Jackie's past along with a suggested future. Hearing about Jackie had me going crazy in my own head wondering could this work for me, would her aunt dictate to me the rules and would all of that break us apart.
My usual way of approaching something new to me would be to listen and digest before using my mouth which is what I did here. I had to also figure out if Jackie was kidding me which was easy then figure out if I wanted to have a sissymaid boyfriend. How does one do that when this was all new to me and I had know one to ask about it. Was Jackie just some crazy guy who likes to wear women's clothes or was there a real person here. All of those feelings rushed through me with either Jackie or her aunt right there. There was another question that her aunt posed to me which was could I even be a Mistress.
Helga, OMG so much was on my mind at once and in my face. Jackie was having her own challenges living together and having an aunt such a big part of her life. So keeping an open mind with Jackie I decided to take on the role of her Mistress. I love her so being mean is not something I can do right now. Yes I understand in time it will be my job to discipline and punish Jackie. Maybe a good spanking might be fun although I haven't done that to anyone yet. Right now each day is a learning adventure for me which is just fine.
Sure when I met Jackie her breasts were no secret to me nor did they scare me away. Now seeing her dressed like a sissy that is something I am getting used to and will continue. She is cute all dolled up and I like the look however it is still new to me. Having Jackie attend to the house and me when I get home is fantastic. I wanted to tell my girlfriend at lunch today but held off for now. Jackie wouldn't have an issue with it as she appears to be comfortable as my sissymaid. It is just me getting used to all this right now.
I am not sure if Jackie shared details with you but I have decided to keep her in chastity suggested by her aunt. It is a good feeling having control of her penis which I have never done before now. Jackie's aunt showed me the strapon that her mother used to use. That was any eye opener seeing it and knowing her mother used to use it. I am getting the feeling that both Jackie's mother and aunt used to control Jackie in many ways. I do hope to live up to the title of Mistress so that Jackie is happy with me too. Jackie's aunt assured me that Jackie is for real so I should do as I wish and not be worried.
Last night I tested the waters asking Jackie many questions and to my surprise she answered them truthfully. I discussed spanking her some day which also appeared to be alright for me to do. We talked about Jackie becoming more feminine again with her not being as quite the way she was when her mother was alive. With that in mind I have requested that she let her hair and nails grow again. I expect to see is full makeup at all times and finally her body shaved smooth as per her aunt.
If I am going to live with a sissymaid and be called a Mistress then my role is to ensure Jackie looks like a sissymaid in all ways. Let's see how well I get used to my words. As I mentioned Jackie is to remain in chastity although we are young and we both love sex. I have agreed to release her so we can make love as long as she goes right back into chastity afterwards. Jackie's aunt talked to me about milking Jackie instead of allowing her to ejaculate however that isn't for me so Jackie lucks out.
Someday I may be more firm with Jackie and get tired of her love making abilities but for now I enjoy her. Jackie's aunt and I had a good chat today as she is concerned all of Jackie's training will be lost. I assured her that by accepting the role of Mistress and that I have no plans of leaving Jackie there is no risk. We agreed that other than the sex Jackie will continue being a sissymaid. The last thing I wanted was having troubles with Jackie's aunt yet at the same time she must understand I am not Jackie's mother.
There you go Helga for not knowing each other I am hoping this email will answer some questions. Now do you have some advise for me being that I am the newbie? I would love to hear from you just to get some ideas that Jackie's aunt hasn't shared or is aware of.
Barb aka Mistress Barb
Thank you for your letter Barb. Being an effective Mistress is a learning experience and her training depends on you now, though in reality you don't have to do that much as she will do most of the work, it does however require a certain attitude and approach, in my opinion and that is to not ask her to do something, but to tell her and if she does something wrong it must be dealt with harshly.