HIS UNCLE WAS MY SISSYMAID
from Joanne

Dear Helga,

When we sat down for dinner this evening I could see that there was something on Paul's mind however I waited for him to introduce the topic which he ended up doing as predicted. Paul let me know before deleting so many of my internet files he couldn't help but notice so many of them were to petticoated.com. Alright so he caught me what was I supposed to do deny it? I let Paul know I go there often and really enjoy the petticoating stories. With a strange look on his face Paul asked why I liked stories about guys in dresses. To be honest I let Paul know his uncle was a sissymaid to me for over 20 years and he loved it.

Paul looked at me again wondering who is the woman that I have known all my life. With that I got up letting him know he should wait there while I went to get a picture of his uncle. Paul looked at with a few no ways and a damn that is crazy. Paul asked if his uncle did that every day as I shook my head yes then he asked if his uncle cooked and cleaned and did the laundry like some of the letters talked about. I replied of course and by the way when did he read the letters on the site?

Paul caught me with the internet files, now I caught him reading the letters. We talked about what his uncle used to do and why he wanted to do it or was it me who forced him into it. I asked Paul if he ever heard his uncle say one thing bad about me when Paul admitted no never. The old story of happy wife makes a happy life worked in our case too.

I talked to Paul about my house and estate would some day become his if he wanted to be part of it. Paul was surprised without ever knowing that until now which made him speachless for a few minutes. I let home know it would all be his if he would do something for me. Paul agreed to do anything for me so I let him know I wanted him to become my sissymaid just like his uncle. While his mouth was wide open I continued sharing my dream of him cooking, cleaning and looking after all the laundry while I worked fulltime at my job.

Paul looked at me letting me know that I was asking the impossible while he could never dress like a girl. I tried again letting Paul know that he would own a fully paid off house, a car and money in the bank if would just accept my offer to be my sissymaid. Paul asked if all the clothes in the spare room closet were purchased for him as I smiled shaking my head yes.

He looked at me shaking his head saying no way he could wear them. So I asked why not with not much of an answer coming back from him. I said look Paul when I die you will have it made which is much more than you have now. He agreed that it was very generous to include him in my will.

I took his hand letting Paul know I at least wanted to see if I guessed his sizes. Paul got up following me to the spare room while I held his hand. While talking to him I started to take off his clothes which surprised him yet kept him calm long enough for me to get all of his clothes off. I handed him a pair of pink panties so reluctantly he put them on with me talking to him about where I bought them. Then I took one of the bras I bought guiding his arms into the straps then fastening it behind him. With each item I let him know what it was called by brand name and where I bought it trying to keep his mind off of what I was actually doing.

A few minutes later Paul stood there from maid cap to heels he was looking more and more like a sissy. I took his hand while we walked to the family room to watch TV. Paul commented walking in heels was harder than I make it look. We sat watching TV with Paul in shock and not saying anything while dressed pretty in pink. A few minutes later I left Paul there while I made some changes to his room getting rid of underwear making room for his panties and bras.

Not wanting to attract Paul's attention I quickly went back to watch TV with him. I asked him how he was feeling just to test the waters. He was honest letting me know he felt like an idiot and looked like one too. Without missing a beat I let Paul know he looked very nice, in fact nicer than his uncle did at one time. Within a half hour Paul was talking to me again thankfully.

Pushing the envelope I thanked him for accepting my offer to be a sissymaid just like his uncle. The more I made reference to his uncle the more Paul settled in to his new role. He asked what else did uncle do when he was a sissymaid. I went through all my husbands duties which as you know Helga everything I didn't want to do.

Paul was taking it all in not saying too much to dispute it. We talked about sissies and petticoating so he could see this wasn't new or something I dreamed up. I felt it was important to keep going otherwise in the morning Paul might refuse to continue. I let him know later on we were going to shave all of his body hair off as a sign of him now being a sissy in training to be a sissymaid. Before he started I assured him that no sissy or sissymaid has body hair neither did his uncle.

I showed him the 3 nighties I bought him with matching panties and a nice housecoat for the cooler weather. He asked me if I forgot anything with a smile when I replied no I had done this before remember. We laughed easing the pressure. I let him know a few times how much l like him wearing a sissy dress and the heels were so prefect for that dress. Paul started to pay attention to what he was wearing and what I was saying about him.

Once again he asked what all I wanted him to do and when would it start. He let me know he knew nothing of an iron or how I wanted him to cook and clean. Just like my husband it took a while so I let Paul know I was willing to teach him everything so he could be proud of being my sissymaid.

Helga I don't expect Paul will be so willing tomorrow or the day after however I will make every effort to keep him on track. Paul doesn't have a clue who is playing with now or that I would have no problem putting him over my knee.

I hope you enjoy the read Helga

Thank you
Joanne


Thank you for your letter Joanne and for writing with such wonderful news, I am so happy for you, I know how much this means to you, even though he is a novice maid and will require a good bit of training, that can be fun too. It must have been some shock to him to learn about his uncle.

So far what you did here seems very effective, I can see you thought about this and were well prepared. I very much enjoyed reading about his introduction, thank you again for the details.

Helga

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