Dear Auntie Helga,
Mom and I went to Alice's house tonight with me looking my best which isn't a daily occurrence. Alice showed us through the house with me taking notes of the floors, bathrooms and bedrooms. She served us some snacks while talking about the sissymaid position in more detail. Alice has a busy life so she wants a sissymaid who can look after the house including laundry which is something like I do with my mom now. She stopped every so often to answer mom's questions which was nice. My mom was very interested in me accepting this position since she did most of the talking with Alice.
I was shown my bedroom during the tour that has its own bathroom permitting me to get ready in the morning without waking Alice until she was ready. My mom asked if I would always be sleeping in my room or was that just until Alice got used to me living there during the week. My mom wants me to have a relationship with Alice and not just be the maid. Alice was good about it letting my mom know I would have to prove my worth before moving into her room.
Alice asked me to stand so she could take my measurements while asking me questions. She wanted to know what kind of bra I like to wear and asked me to show her and with my gynecomastia condition I have worn a bra for years, usually rather plain. Right away she said to my mom something sexier would be more appropriate didn't mom agree. Alice asked my size so I told her 38F as she wrote that down. She commented on my dress liking it however felt as a sissymaid I will want to show more cleavage. My mom asked how much more concerned of me showing too much. Alice let her know the sissy dress design she had in mind did show cleavage. She showed my mom a picture and from what I saw it was lower than my dress but not that revealing.
Mom bought my dresses and was always concerned men would be looking at my breasts even more of they were hanging out as she calls it. Alice was professional in her approach with my mom which helped the process go well in my opinion. Alice asked if I like to wear pantyhose or stockings. When I said pantyhose she told me I will be getting used to stockings and a girdle. Mom all of a sudden started agreeing with Alice. After Alice got all my measurements we talked for a while about hours of work and more about the job part. Mom asked Alice what type of punishment would I be looking at for mistakes since she felt I would always try to do a good job.
Alice showed her a leather handled wooden paddle and a riding crop for horses. Mom looked at both agreeing they will work well as she winked at me. Alice asked my mom, not me, if it would be alright if she tried a couple of chastity devices on me. Mom said sure why not Alice. I asked mom would that be necessary when my penis doesn't work that well with taking hormones. Mom thought it was fine to at least try them on so Alice went to get them. Mom asked me nicely to stand up so they both could pull my pantyhose and panties down. Alice had never seen my smaller than it used to be penis.
They didn't say anything about the size of my penis just that I did a good job of shaving. Alice put a plastic one on me then changed it to the metal one because it was for a smaller penis. I stood there blushing but couldn't see past my breasts to know exactly. Alice asked my mom what she thought of the metal one with mom agreeing it was the better choice. She handed me a mirror so I could see my penis inside this metal chastity device. Alice told me that was the one and that she wanted me to wear it from now on looking at my mom for approval.
My mom looked at me agreeing with Alice the metal one looked the best and that it was going to be on there for quite some time. Alice thanked my mom for the support of everything they discussed. With that Alice brought out a sissymaid contract to make it official giving my mom a copy so she could read it first. Mom sat there looking over the contract shaking her head in agreement with what she was reading. She asked Alice a few questions for clarification then agreed with the contract.
My mom passed it to me to read with a pen. The contract spoke to Alice's role and my role, my appearance, my duties and punishment options for Alice. Most of it looked like it belonged there but the punishment section didn't at least to me. Alice talked about why it was necessary and how some sissymaids don't live up to what they promised. My mom felt with my hard work I wouldn't be punished too often. Mom handed me the pen to sign the contract and she signed as a witness.
Alice congratulated me and my mom for accepting the job. She said my dresses will take about 10 days so in the meantime she would have me wear a maid uniform. I asked will it fit me looking at my breasts. Alice went to get it while mom helped unzip my dress. When Alice came back they put the dress on me which was a size bigger than what I wear. I couldn't do the top 2 buttons but surprisingly it fit not that badly. Mom looking it over pulling and adjusting it agreeing with Alice it would do for now.
Mom looked at me pointing out her son was now a maid and a pretty one too. Alice agreed with my mom. She asked my mom if she was okay for me to start work tomorrow. My mom looked at me agreeing tomorrow was fine and she would drive over in the morning. Alice gave me a list of what to bring and to let her know what I needed more of until I got settled with a routine. She gave me a hug letting me know it was going to fine.
On the way home mom talked to me assuring me Alice was going to train me to be not just a maid but a sissymaid. Mom feels that a maid role is good for me and my feminine side will blossom instead of me not knowing if I am male or female. Mom wants me to be more feminine as I go on in life because she sees me happier when I am out with her wearing all women's clothes. At home I am more confused who I am she feels. Mom knows best and I can't disagree with her having seen me growing up.
I asked my mom what if I was just a regular maid like at a hotel when she looked at me asking if I would even go for an interview. You see my mom knows I would not be able to go for an interview in men's or women's clothes. Mom strongly feels although there are aspects of being a sissymaid like punishments that in time I will be very happy serving a woman. Mom always tells me women understand more about differences people have are less likely to make fun or even stare at men like me.
She is right when we have gone shopping women see me because of my breasts I guess but they usually smile at mom and me. It is almost like they know what mom is going through and what I am going through. Men would look at my breasts only then call me names knowing I am a man. Mom told me as long as I am a sissymaid there will be a good woman in my life because women appreciate sissymaids and the work they do.
Alice felt that me becoming a sissymaid Monday to Friday with her would be even better if I was fulltime including at home. Mom agreed with that when I was in the bathroom at Alice's house. Mom called me into my room with that news and asked me to help her pack up all my men's clothes. I looked at her knowing she was right but hesitating until she took my hand with the usual come on now it will be okay. Mom's plans are to buy me new clothes that I can wear on the weekends that give me a break from the sissy dresses. She thought a new maid uniform something like what Alice had me try one would make sense. Mom did tell me when we go out on the weekend a couple of new dresses would be nice for me to wear.
Auntie Helga after all these years it looks like I am going to live out the rest of my life as a sissymaid with Alice. Mom told me that if for any reason Alice doesn't want to keep me as her sissymaid she will help me find another Mistress. I can see my mother is fully supportive of me as a sissymaid more than she has with me being anything else. Maybe mom sees this as my calling in life, I am not sure.
Auntie Helga I know tomorrow will be a very busy day for me while I get adjusted working as Alice's sissymaid. If you don't hear from me please understand I am busy. Alice did agree to me having some free time at night and breaks through the day. I have makeup to take off and some packing to do for tomorrow.
Thank you for your letter Joni. Some men that have these conditions do in fact become sissymaids, it as though they were predisposed from birth for this wonderful life. I think its a great idea and will be good for all involved.
You will get used to sissy dresses quickly, they feel delightful to wear. I suggest you accept her offer. Of course a sissymaid really has no need for a penis at all anyway and so your small penis is preferable and lack of erections is not an issue either. Your shouldn't worry about it.