John to Sissy Jenney

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My son John has always been interested in being a girl. From a very young age he would dress up in my clothes. When he turned eight he had been dressing for several years. I asked if he would like his own girl clothes to dress up in? He said he would like it very much and over the next few days constantly asked when he was going to get his new clothes. I tried to discourage his enthusiasm by telling him if I bought them he would have to wear dresses and act like a girl and not boyish. He was all for it and would cry when I told him he had to wait until the weekend.

The weekend came and we went shopping, once in the girls department he had his hands running through all the clothing. Feeling the silky, satin panties with lacey openings and dainty dresses, socks with bows, flowered shorts, ruffle blouses. I could see right away that he was drawn to anything with satin or lace and ruffles. I bought him two dresses with lace, one cream colored and one in light pink. Seven pares of panties some in cotton with flowers and some satin with bows. Three blouses with ruffles, in pink , white and yellow and one pair of slacks and two pares of shorts.  Pink, white and yellow socks with little bows and some with lacy tops and one pair of maryjane shoes.  I was all smiles and when we arrived home he tried them on and modeled for me, keeping on a lacy dress and satin panties with lacy top anklets and his maryjane shoes. He was so cute and so sweet that weekend I told him he could grow out his hair so we could curl it when we go out.

One day he came home pouting because he had told some girls that he had some pretty dresses and they made fun of him. He wanted to know if he could wear one to school the next day so he could show the girls. I told him no, and not to be telling anyone that he was a girl.  He cried as I pulled him close and stroked his hair telling him to go put on something pretty. He came skipping into the room twenty minutes later in one of his outfits. That summer we moved to another state and John became Jenney. From then on he was dressed and taught to acted as a girl. Once I could see she had adapted well I figured that I would home school her and teach her amongst other teachings, to be as dainty as possible.

When Jenney turned sixteen I sat her down and explained that boys will want to date her at some point and that she should get use to the idea of having a boyfriend. Jenney had a lot of questions and by the end of that summer I had her wearing a chastity cage to contain her erections. By age of eighteen when we where at a wedding dance,  and a very handsome boy came over and asked her to dance. David being four years older than Jenney became good friends that summer and went out on dates every week. I knew that David was more mature for his age and I sat him down one afternoon and told him about Jenney. That Jenney was a boy in a girls body and has been living as a girl most all her life. David seemed more interested than appalled at this and had a lot of questions. I informed him that I kept Jenney in chastity for the past four years to control her erections. I also told him it might be time for him to take her to the next step of being a women. I gave him the okay and told him that he could use her bedroom. I called Jenney to where we were talking and brought her up to date on what David and I had discussed. She just stared at me as if she was hypnotizes with all the information. I told her to lower her panties and lift her dress to expose her little sissy cocklit as I unlocked the cage her three inch erection pointed straight up. David smiled as he stood, taking her by the hand saying her time had come to become a women as he took her to her room. I could here cries coming from the bedroom knowing that Davis had mounted Jenney and she was having sex with a real man for the first time.

A year latter Jenney told me that she wanted to become a sissy. I had not thought to much about what she told me. Then she told me of some sissy sights to lookup. I was surprised that she would want to become a sissy and asked what made her choose this? She told me that David had a party two weeks ago and had some of his friends over. Jenney was the only girl there and they all taught her what a sissy was good for. She confessed that she enjoyed it and now wanted to live as sissy. I called David to come over so we could talk over Jenney’s decision. We agreed that Jenney would move in with him and be his sissy. I asked if he would go out of state and marry Jenney since it was not legal in our state. He told me that he would consider it if Jenney became a proper sissy. He was going to send her to Sissy training once she had moved in. He also informed me that part of Jenney’s job would be pleasing his friends as one of her jobs. Jenney seemed to be happy about this and I agreed to it beings this was what she wanted. Over the last two, I am happy to say that she has adjusted very to being a sissy by acting and dresses the part.

Once John now Sissy Jenney.

 

(SM) Sissy Maker

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