GRANDSON CROSSED THE LINE - CONTD.
from Nancy

Dear Helga,

Taking into account our discussion today along with some ideas I had in the back of my mind I decided to move forward with Robbie. Living across the street from a mall and all kinds of shops on the other corner I went shopping with Robbie's bank card that I manage. I bought Robbie a couple padded bras, a slip, pantyhose, stockings and a girdle. With me buying his clothes sizes were no issue. Al;so there is a woman that lives near me who works at a new and used clothing store. They sometimes have dresses and shoes in odd sizes that don't sell in the big stores. I had in mind to buy Robbie a dress but not a very pretty one. The idea in my mind was to just buy him his own dress with it being something he wouldn't get excited about. The sissy dress with be the opposite if you see where I am going.

Looking around I finally found something in a size that would fit Robbie and maybe one size larger and a pair of shoes right beside the dress. They must have been brought in from the same person. When I went to the cash I met the woman living down the street. She looked at the dress and shoes asking if I really wanted to buy them. I said well yes as part of a joke to teach someone a lesson. She looked around telling me they had been there for weeks so she was going to give me the dress for free and just pay for the shoes. I think she was happy they dress was out of the store and I was happy to have it free. On my way home I was going over what to tell Robbie when I thought just be honest. He came home just as I unpacked everything in my bedroom. He hasn't done anything wrong for a week and does wear his panties every day.

I sat Robbie down to have a talk with him while he looked at me wondering what he did wrong. We started to talk about him wanting to wear my clothes a few years ago and that urge is still part of him. Robbie apologized wishing he did want to do it so much. I put my hand on his shoulder letting him know I finally understood and wanted to help if he would allow me to.

Robbie was hearing a new side of me Helga and showing interest. I talked to him in a semi serious tone about wearing his own dress and shoes only in the house. Robbie was surprised holding back on me before answering. I offered him a deal and that was the only way it was going to work. He asked me what that meant so I talked to him about wearing a dress that I bought and the shoes as long as he was willing to learn how to cook, clean and do the laundry.

Robbie asked what kind of a deal was that to offer him. I didn't say anything then he well okay Grandma. With that I sent him to take off his clothes and come back in his panties which was the first time I saw him in his own. Blushing in front of me I talked to him like a daughter showing him the bras I bought giving him one to try on for me. Surprising to me Robbie knew how to put on a bra properly. I gave him the slip I bought while telling him the brand name. Robbie slipped it over his head and I help him adjust the straps.

Before showing him the dress I was careful to let him know it was a temporary dress with me having a pretty one made for him. I wanted to get his measurements so the dress would fit better than the one I bought today. Up until now Robbie had no clue what a proper fitting dress would be like only having tried mine. He commented that it was something he would have bought.

I was talking to Robbie telling him finding shoes his size was impossible but I found a pair that would hold him over until a nice pair came along. With that Robbie slipped on the shoes and surprising to me he likes them. Looking at my grandson standing before me I wanted to get a feeling from him it was alright. It wasn't long that he hugged me and thanked me for helping him deal with his habit.

I once again reminded him that he had to live up to his part of the deal or else. He said anything grandma and thank you. I let Robbie know it was my feeling that I could help him instead of getting angry. Robbie looked at me asking did I want him to be like a maid now. That I didn't expect to hear but had to say yes to him. I asked Robbie what did he know about maids and why did he ask that question. He was telling me about a website that he saw men dressed in maid dresses and women watching then ironing and washing floors. Helga there was no pretending I didn't hear that then try to bring it back another time.

I just spit it out letting Robbie know that is what I wanted him to do for me and if he did I would buy him a closet full of pretty clothes. He looked at me then down at his dress and shoes. I went on to tell him from now on I expected he would come home from school and wear his dress and shoes helping me with the housework.

Robbie asked if I wanted him to be a sissy maid so I answered in time yes he would be my sissymaid. I let Robbie know it would be my pleasure to train him how to be a sissymaid if it was something he wanted me to do. It wasn't a quick yes Helga but it was a yes. Tonight we are going to get started on what I think he should learn. This is a big step for me and maybe Robbie too.

Thank you so much,
Nancy


Thank you for your letter Nancy. Really well done, your loving yet firm approach has done it, now you are well on your way to having your very own sissymaid and I couldn't be happier for both of you.

I wonder if the website he was talking about was mine, though really what matters is that he is aware of this and has agreed to obey you. It is a big step but I know how much you love him and want whats best for a happy home, his secretly wearing your clothing was not good, his shame and your anger were counter productive and now that clock is reset and together you can change things for the better. (By coincidence the first letter was published one year ago this month.)

Helga

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