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Date Posted: 10:56:04 06/28/16 Tue
Author: Amanda (love)
Subject: My Son is Now Dressing as a Girl

Hello,
My name is Amanda. How is stumbled on this site I will never know. I had no idea anything like this existed. Word of warning: I use some explicit language some may find offensive.

I am a 36 year old mother of a 12 year old boy, Michael, who now goes by the name of melissa, but we use missy for short. My husband and I divorced shorted after Michael was born, and he is out of our lives entirely after he revealed himself to be gay. Fortunately his family is very wealthy, so the settlement left me wanting for nothing, but I did choose to work in my profession as an attorney. It is just missy and me in our household now.

This all started over a year ago when I noticed my things were out of place in my drawers. I smiled to myself, knowing full well that Michael must be experimenting with his feminine side. He is a small boy, thin but healthy looking. He would often comment on what I was wearing and how pretty I looked. He enjoyed shopping with me, certainly rare for a boy in puberty. Since I am always in a rush to leave for the office, I thought I would have him help me dress. Since it is just him and me, he has seen me naked occasionally so I really didn't think a thing about it. So, one day I asked him if he would like to help me, he didn't hesitate in saying "yes!" Soon he was fully into it. I showed him how to roll up stockings, place my foot carefully into them and unroll them on my legs and fasten the garter straps to them. I love stockings, they just feel so nice on my legs. Of course he zipped up my skirt or dress, and even helps me with my bra. He showed an eye for fashion also. It wasn't long before he was picking out my clothes for me!

One day during the "morning rush," I glanced down and noticed that he was sporting a little erection in his pajama bottoms. I asked him how long that had been going on and he said for a while. When he asked me what it was, I know we had to have a little talk, so that evening we sat down and I told him it was called an erection and boys started getting them at his age and they were entirely normal. He told me he got them when he was helping me dress and after he went to bed. I then asked him what he was thinking about when he got them, and he told me it was when he started thinking about about wearing pretty girl clothes like I wear. I then asked him if he had been sneaking and wearing my clothes. He turned beet red and replied, "yes maam." At last we were in the open on this. "Do you get an erection when you are wearing my things," I asked. "Always," he replied. I then asked if he knew why that was, and he said he didn't know why. I told him you get those when you are excited, which I went on to explain excited is a special kind of happy.

I then asked him if he would like to be pretty like me. His face just lit up and he said "I would so love that mommy." We talked about it a while. I told him if he really wanted to do that it would have to be all the time, not just now and then. He couldn't go back to being a boy. I would quit my job and we would move where no one would know us so he could start out fresh. I then found some things of mine for him to wear, which was difficult as I am quite a bit taller than him, but I was able to fit him out in a skirt, stockings and garter, bra, panties of course, and some stiletto heels a friend had left at our house. I styled his hair into a cute blunt cut until he could let it grow out more. It was obvious a major shopping trip was in order but this would do nicely for his initiation into girlhood.

He became so nervous, shaking all over after seeing himself in the mirror, but he was so cute! We smoked some pot in order to calm him dow. We walked around the room so she could get used to the shoes. He had a little erection sticking straight out of the skirt. I thought now was the time to show Michael what to do with his excitement. I had him lie down on the sofa, pull his panties down to his ankles and hike his skirt up. I gently started to message his little thing and he instantly started to moan. Before long he had orgasmed, squirting a river of semen all over (my!) lined skirt. He enjoyed it immensely.

We had a long chat after that. There would be rules: skirts and dresses only; no shorts or pants. If he wished to masturbate, he must always ask permission. He must take care of the house, as a maid. Last but certainly not least, we must choose a new name for him.

This was how it began for missy about a year ago. So much has happened since then I couldn't possibly write it all at one sitting. Hopefully I will be able to return and add to it.

Loving written,
Amanda

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