My Life in Girl's Clothes

Dear Auntie Helga,

My wife of many years has rather strongly suggested I write at tell your readers about myself.

I was born in Toronto during WWII to a widowed working class mother. My father had been killed during the Normandy invasion. I had one sister two years older than myself. Needles to say times were not the best and until I went to school I wore nothing but my sisters hand me downs. This was not uncommon in those times. However, even then when coming home from school I had to change into my play clothes which of course were hand me downs. Mother had stopped putting me in dresses when I was about 6 I think but all my play clothes were of course girls. I even had some which were given to my mother from my aunt and were clothes outgrown by a female cousin.

I think I was 11 at the time when I found a very feminine short set in my drawer and complained to my mother. It was peach colored with elastic around the ruffled arms and legs. Actually I guess I did more than complain and threw a bit of a tantrum and said I was not going to wear something so girly. Well, mother hauled me off to my room and stripped me to but and gave me a good spanking. She left and came back a few minutes later with a sun dress of my sisters. Well she said, if you think the shorts were too girly perhaps you will find this more girly and put it on me along with a pair of my sisters white sandals. I cried as she took me to the porch and made me sit there in the dress for all passers by to see. For the rest of the summer my clothes became decidedly more girly and I found myself in dresses or skirts almost every day. Everyone saw me as I was made to play outside and go shopping and visiting dressed this way. I was the subject of much humiliation by other children but sometimes complemented by adults saying how I seemed to suit girl's clothes.

When school started that fall I was allowed back to my boys school clothes but still was made to wear the hand me downs after school and on weekends. Dresses were less frequent but on many occasions I was made to wear them especially for visiting.

I guess I came to not only accept my fate but started to actually like the girl's clothes. Although I put up a fuss when mother put a girdle on me I actually liked it. She told me it was necessary for my slacks to fit properly. She also told me now I would have to sit down to pee so I would no longer splash and dribble on the floor.

By the time I was 14 my sister clothes no longer fit me properly and mother started to buy me boys slacks, shirts and things. I missed the girl's clothes even though wearing them made me feel very self conscious and at times humiliated and I guess mother sensed it. One day when shopping we were in a department store in the girl's dept when mother held a dress up to me and asked if I liked it. I kind of stammered and said yes. With that I was taken to the fitting room to try it on. The sales lady kind of joked and said it needed something on the top to fill it out. With that mother just said, lets try a little bra on him to see how it looks. Being going through puberty I had rather large breasts and they fitted me with a full A cup bra. I was kind of proud and humiliated at the same time, especially when the sales lady told me how nicely I filled out the bra. I could not believe myself when I asked if I could wear my new outfit home.

Well, for the next several years I dressed in girl's clothes as much as I could and loved it. Mother seemed to revel in the fact that I could look so feminine. She called me her sissy son. Even my older sister was now treating me like a sister..

In college I met Fay, my future wife. After meeting my mother a couple of times she was made aware of my like for feminine clothes and after seeing me in them a few times she seemed to like the dual me, We married and for many years I worked as a man but was the second woman in the house when I was at home. Over the years we have gone on several vacations as girlfriends. Sometimes I pass as a woman but at times my wife likes to keep me in line by exposing me as her sissy cross dressing husband. These time can be quite humiliating ad do get me a lot of attention, especially when shopping or on a cruise.

In six months I retire and Fay has suggested I become Jillian full time. I am ecstatic. We have purchased a motor home and plan on traveling North America as girlfriends at least most of the time. My wife has told me I will not be allowed to take any male clothes whatsoever.

I will write you again of our travels.

Sincerely
Jillian


Thank you for your letter Jillian. What a wonderful story and I hope you appreciate just how fortunate you are to have a wife that continues this effective treatment. We'd also love to here about your travels when you get a chance to write again.

Auntie Helga

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