I hope you do not mind me writing to you this evening after reading the latest monthly letters. My situation is rather odd where you may have seen or heard what I am about to share before. It was three months ago when I discovered some pictures on the home computer surprising the heck out of me. There are only two people using our home computer, my husband and myself. Guess who put the pictures on the computer? Anyways the pictures I found were those of maids serving women dinner and drinks. Oh, but after looking again the pictures were not female maids instead were men made to look female. So why was my husband looking at men dressed as female maids I asked myself. Looking further I discovered my husband appeared to have a thing for sissymaids or was it he wanted to be one.
Helga looking at everything on the computer it became clear my husband had a fantasy or a strong interest in sissymaids. Was he wanting to be with a sissymaid and was he gay I asked myself. I couldn't find anything in the house other than the computer pictures to make me think any differently. Rather than freak out on Gordon having had a few days to digest and think about my findings the plan was to discuss it with him. Helga not having any experience with men's fantasies especially not one about sissymaids it was new to me making me think it through before speaking to Gordon.
I started to read about sissymaids and Mistresses who kept them learning as much as I could while preparing to surprise Gordon. One night after a nice dinner I asked Gordon to do the dishes and clean the kitchen for me. It was something he rarely did however there was no argument from him. Gordon brought me a coffee while relaxing watching him clean up for a change.
When he was finished I commented that Gordon would make a good maid with a smile. We talked for a while until I made mention of having a few girls over for dinner some night. Gordon thought it was a great idea until I asked him if he wanted to be the maid of the night serving dinner to the girls. Helga the look on Gordon's face was one of confusion, excitement and surprise. He asked me what I meant so I explained we would make dinner together then he would look after serving drinks, dinner, desert and clean up just like a maid would do.
Poor Gordon didn't know what to say however it was clear to me then the pictures on the computer meant more than my initial thoughts. Taking Gordon down to the basement I presented him with a maid uniform with all the trimmings. Without going into detail about what was on the computer I coaxed Gordon to try on his new maid uniform. It was clear to me as he put on a pair of silky panties there was a level of excitement as his penis stood right up.
I helped Gordon with his bra, girdle and stockings before slipping the uniform over his head. Surprisingly Helga there was no push back or talk back from Gordon as he stood there for the first time dressed as my maid. I heard other Mistresses used compliments to help their sissymaids become comfortable with their new position and the same worked with Gordon.
Knowing Gordon fantasized about not only being a maid but also serving a group of women I started to train him on cooking, serving and cleaning up the kitchen. Every night when Gordon came home from work one of his uniforms was waiting for him to wear so we could get to work. It has been a few weeks now with Gordon following my orders while I prepare him for a night with the girls as my maid.
Gordon hasn't asked why or complained about the training or even wearing one of his maid uniforms yet. I have given him a date when the girls will be here for dinner and a goal for him to be ready.
Helga so far so good however do you feel I should also put Gordon in chastity from now until the dinner night or permanently? Also do you feel taking Gordon with a strapon is optional or mandatory for sissymaid training? I look at what we are doing as fulfilling his fantasy however I want to be prepared if he decides no more at some point.
What do you think?
Thank you for your letter Danielle. I don't mind you writing at all, I would be happy do what I can to help. I can imagine your surprise at finding those sissy photos. Isn't the Internet a fascinating thing.
I am so pleased to see that rather than dismiss this discovery you did your homework and thought it through. As you can see, the benefits are plentiful. Great idea about the dishes, and to see him hop to it must have been interesting. And then to a party, I see where you're going with this, good plan.
You are off to a great start, yes, chastity is best and from now on, not just until the party, the party could be just the start of a long term commitment. The strapon can be one of the most sexually exciting things you can do, I fully recommend it. This may well be his fantasy and that's the way it started, but this can be a whole new lifestyle for you both and very fulfilling at that.