Dear Auntie Helga,
My girlfriend has been talking about sissymaids lately so I wanted to know more about it. When I found your website and email address I thought why not write to you about it. I read all the letters and looked at the pictures so I know more now than a few days ago. My girlfriend Cathy always told me I would make a pretty sissymaid which wasn't what a guy wanted to hear.
Cathy wanted to prove it to me so one night she curled my hair and put makeup on me. She bought me a bra with fake boobs, panties, stockings, a garter belt, high heel slippers and a nightgown. By the time she was finished I looked like my sister more than I thought possible. So Cathy proved her point wanting me to wear the stuff she bought me more and more. Cathy is one of those women who likes to get her own way and likes to have fun getting it. When I was at home Cathy wanted me to get used to wearing the stuff she bought while she was at work. She wanted to buy me a either a sissy dress or a maid uniform this week of which I wanted neither. I was thinking Cathy was moving too fast but I played along.
Before I started writing this email today I did put on the women's stuff Cathy bought so I was sitting here in the nightgown and all the rest. Cathy suggested I wear it more to get used to the materials and wearing a bra would take time to get used to. Part of me felt silly looking at my shaved legs covered in stockings with high heel slippers on my feet. The bra with these fake boobs sticking out was another story. Cathy thought I looked cute but then what guy wanted to look cute.
Cathy called to see if I was wearing my stuff this morning and when I let her know I was, she was happy. Cathy asked me to call her friend Jennifer to see if they had maid uniforms in men's sizes since she was too busy at work. Cathy told me it was alright since they knew one another and Jennifer was expecting my call. I didn't want to call and was embarrassed to think about it but knew Cathy would know if I didn't call. I waited until after lunch then I called to talk with Jennifer. She was very nice asking me my men's sizes as she looked at her computer to find the women's size. I asked her how many men bought maid uniforms or wives bought them for their husbands or boyfriends.
Jennifer told me it was far more popular than I thought and her company was talking about making a line of maid uniforms in men's sizes in the future. I was very surprised but then knew why Cathy wanted me to be her sissymaid like it was becoming a popular thing for women to have a sissymaid. Jennifer talked to me about the styles and colors that Cathy wanted me to wear. Jennifer suggested I come to see her and bring my bra and stockings for uniform and shoe fittings.
I thought no way I could do that so I let her know I would have to get back to her on it. It was less than 5 minutes after I hung up when Cathy sent me a text letting me know about my call with Jennifer. Before I replied Cathy told me to go see Jennifer and try on the uniforms and shoes. Auntie Helga I was so nervous and waited a while until I got another text. I left my bra and stockings on but took the fake boobs out and put them in a bag. I wore a shirt and pants to hide what was underneath. Leaving this email unfinished I headed out the door.
I met Jennifer who was a very pretty lady as she showed me what Cathy had in mind. Jennifer took me to a change room in the back away from other customers where I tried on a couple of uniforms for her. I felt so embarrassed when Jennifer told me not to worry lots of men become maids these days. Jennifer looked at me in both uniforms with my fake boobs in my bra for the full effect. She got me a few pairs of shoes all with heels as I held the wall while she slipped them on my feet.
Jennifer gave me her expert opinion on the pink uniform with a white apron and white trim to match the uniform. She packed up 4 dresses and 2 pairs of shoes wishing me good luck as I walked out of the store. By the time I got home Cathy had texted me letting me know how happy she was I went through with it. Cathy told me in text to surprise her when she got home with me wearing one of my new uniforms. After being humiliated with Jennifer putting on a uniform for Cathy would be easy.
Now as I continue my email I sit here dressed as a maid for Cathy who is on her way home to see me. Auntie Helga I am nervous and terrified all at the same time. I shaved my armpits and my pubic area since Cathy was bugging me about it yesterday. I don't feel very manly right now that is for sure. Cathy talked me into all this without me saying no way which is what I would normally say.
He is what is happening Auntie Helga. I was going to ask you for advice when I started this email before the situation changed. Maybe it was going to change anyways and the timing of me email was perfect. All I can hope for now is Cathy doesn't want to be a Mistress like some I read about. Auntie Helga I won't ask you anything stupid like is this normal or how do I get out of this mess since I know you will probably tell me it is okay and to go with it. What I will ask is do women accept having a sissymaid dressed as a maid or do they end up putting their sissymaids in sissy dresses? If I have to be Cathy's maid I can live with it but I'm not fond of those sissy dresses at all. Then again I am not fond of the uniform I am wearing but I'm wearing it now.
Thank you for your letter Cam. What wonderful new adventure you are embarking upon, I know how confusing it seems right now to you but making a small sacrifice of your masculinity to please the woman you love seems a small price to pay. Each Mistress is different with some preferring a sissymaid while others tend towards a conventional maid's uniform though of course the decision is hers.
It will be fine and you can do this for awhile, it might even be fun.