from Sissymaid Merri

Dear Auntie Helga,

Yes my Mistress is very thoughtful and I know that she was thinking about you when she decided to have me share my training with you. She seems to enjoy showing off to other Women how well she has trained me and so I think she is enjoying having me share my lessons with you. She has stressed to me that I'm to share every intimate detail of my training with you that I can remember so I'll try to do my very best. She really did spend quite a bit of time working with me to help me become a sissymaid and I really do very much appreciate it.

Right from the start Mistress made several things clear to me. She made sure that I understood that if she was going to play our game and indulge me that she would be in charge. I was to agree to all of her rules including any discipline she might deem appropriate or the game would end immediately. I was so excited that I would become her sissymaid that I immediately agreed without giving it much thought. With a devious grin on her face she emphasized that if I was going to dress up like a girl that I would have to look and act like one. She said that her Mother always said that nice girls don't initiate sex. She said that went double for sissy girls. She said that she had no interest in making out with another Woman so I would have to learn to control myself at all times. She told me that meant tucking away my sissy parts so that I wouldn't be tempted to use them like a naughty girl.

While she said she wasn't excited about living with another girl she said that she was excited about having maid service. She made it very clear that my position in the household would be to work as her domestic maid. Later she also made me her secretary. She also made it very clear that since I was being indulged in my sexual fantasy that her sexual pleasure would always come first.

It took considerable practice and I did have to concentrate to apply my makeup to the satisfaction of my Mistress. She insisted that I didn't have a clown-like appearance like the way some sissymaids make themselves up. She really stressed the natural and authentic look that she wants me to strive to have. At the time she liked to say that if I really wanted to be a sissy so bad then she would make sure that I would become a true sissy from nose to toes. She also insisted that since I wanted to dress like a Woman that I would be taught how to serve her like a real hired female domestic maid. She has always said that anything less would detract from the pleasure of her own fantasy.

For Mistress that meant that I was even to wear panties and a bra all the time beneath my clothes. At first I wasn't sure that I wanted to do that full time. She really didn't give me much of a choice because she had me take all of my guy clothes to the second hand store. I wasn't sure if she was angry at me when she made me do that or if she was making a point. Anyway at the time she told me that I would get used to the attire and that soon I wouldn't feel right unless I was wearing Women's undergarments and Women's outerwear. She was right about that.

She would get irritated with me if I gave her any indication that I didn't want to fulfill her fantasy just the way she envisioned it. If I annoyed her too much she would remind me that it was my idea and that she was only giving in to my tawdry desires. She often used the word indulge when she referred to my training and after a while I just came to accept the full feminization treatment as part of my tutoring.

So the makeup lessons continued for quite some time until I started to become comfortable applying my own makeup. At the same time Mistress started playing dress up games and putting me into different outfits. She tried different hemlines on me while she decided on how she wanted me to look. I felt a bit slutty in the dress shown here but when I mentioned it to Mistress she said that was the idea. Mistress always says that a girl should show a little leg. The dress was another hand-me-down from her wardrobe that she used to wear when we were single. I suppose that I deserved to feel slutty in it because of the ill-disciplined thoughts I used to have about her when she wore it.

Most Humbly,
Sissymaid Merri
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Thank you for your letter Sissymaid Merri. I certainly do appreciate her thinking I would enjoy reading about your early training and of course I do, the beginning is so important, taking an otherwise masculine man and helping him to realize his potential to become the feminized submissive sissy she is today takes skill and determination coupled with heavy doses of humiliation and occasional pain your glorious Mistress has in spades. You are the living embodiment of her power.

She indulged your fantasies and desires and now you are living your dream, isn't it wonderful? I just love how she had you wear the very clothes that you lusted after when she wore them, now the heel is on the other foot. Charming photo, thank you.

Auntie Helga

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