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Crossdressing Guide

One of the most wonderful parts of my work for JJ has been the opportunity to interview some of her girls. This third interview is with Kathryn who has come to depend upon JJ as her crossdressing guide and mentor.
Charlotte, PA to JJ

Crossdressing Guide

Kathryn’s crossdressing guide was found in the form of the Crossdressing Service in Cheshire.

Charlotte: please tell us how crossdressing started for you and how you felt at the time?

Kathryn: My first fantastic moments happened when I was eleven. I would come in from school and would always have a bit of time to myself as my parents would not be in till six o’clock in the evening. So I would sneak some of my mother’s tights and underwear at first. Then as I became bolder and braver, I found a skirt and blouse that fitted me really well. I could never find shoes that would fit perfectly and this used to frustrate me because I just wanted to look as feminine as possible. I experimented with make up to but was not very good lacking a crossdressing guide to this difficult art.

Was there any critical turning point in your first dressing experiences?

My dressing in secret snatches at home went on for about a year, with of course no crossdressing guide other than my own instincts. Then one day my best friend’s sister invited me to a fancy dress Halloween party. I asked her what I should wear and she said she would help. So one evening I went to her house and she came out with this black and white polka dot dress: “Put this on,” she said. I thought: “Wow, did she know I was in heaven?” She even let me try her shoes on as well. From that day on I was truly hooked and I still have that wonderful memory deep within me. She was my first crossdressing guide.

Did you have a role model in these early years?

My auntie was such a dear friend as well as a relative. Perhaps she was a kind of role model for me in a sort of away. She used to dress in skirts and blouses and I have always loved that look. But sadly my auntie died when I was only 15. So I never know whether or not she would have become a crossdressing guide for me.

Kathryn in her 1920's outfit

Kathryn in her 1920’s outfit ready for the Murder Mystery party she will be attending in April.

How did your crossdressing develop as you grew older?

I would keep experimenting with different outfits on and off for a few year until my education at school was over. I even thought my need for crossdressing would pass; but how wrong I was! It seems now that every spare moment I had was taken up with my crossdressing; and with money in my pocket when I started work, I could buy my own clothes and shoes. But still I always dressed in secret, even when a few years later I got married. Throughout this time I remained my own crossdressing guide.

Tell us about the first time you bought your own clothes? Were you nervous?

I remember well that first time I bought clothing was a Saturday afternoon. I was able to drive by this point, so thought I will go where no one knows me: so it was a ‘self’ crossdressing guide trip to Morecambe. There was a women’s dress and clothing shop on the promenade. I was so sure I was going to come away with some item of clothing, but without a crossdressing guide my nerves took over. I just did not get the courage to go through. But I kept making trips to the same shop. Then one day the shop assistant came over to me and asked if she could help me: a crossdressing guide at last. Her name was Jenny and I remember was so helpful. Despite my nerves and perhaps because of her role as a crossdressing guide for the day, I did manage to come away with a black skirt and a white blouse. It was some time before I could summon the courage to return. But when I did I bought tights and underwear. My inner crossdressing guide knew what she wanted!

And when did you start to build your crossdressing guide wardrobe and wear a full set of women’s clothes?

I was seventeen: I wore a leopard print dress and a fine pair of suede knee boots; and yes these came from the shop in Morecambe which with its fantastic assistants had become my shopping crossdressing guide in these early years.

And were you ever tempted to try a dressing service to act as a crossdressing guide for you?

Yes, since my dressing before and after my marriage was always in secret, I did try out a  crossdressing service in Manchester and one or two others. But until I met JJ, somehow I just didn’t feel secure with these services as my crossdressing guide.

Crossdressing Kathryn looks so elegant

Crossdressing Kathryn looks so elegant in her pearls and faux fur wrap.

And how did you come across JJ’s crossdressing guide service?

The first time I saw JJ’s website – such a wonderful crossdressing guide all by itself – my breath was taken away.  I would pick up my iPad ever night and read more; and more reading the crossdressing guide testimonials, I just knew I have to see JJ.

The first visit to JJ as a crossdressing guide, mentor and friend is always momentous. Tell us how you felt.

On my first visit to JJ’s crossdressing guide service, I felt so nervous before we met; I don’t quite know why really but my anxieties were soon put at ease when we met. She is such a lovely warm person and is so welcoming. We chatted about Kathryn and her journey. I remember on that first visit I wore a white satin blouse, black pencil skirt and a lovely pair of high-heeled black shoes.  Afterwards, having found my true crossdressing guide, I felt I was on top of the world. Kathryn was finally developing the look she had longed for all these years and I have grown in confidence ever since.

So what styles does Kathryn like now?

I love to wear red and black underwear especially black stockings; and I still am totally hooked on skirts and blouses especially the pussy-bow satin ones. But with my crossdressing guide’s help, I do explore other styles. I now have quite a lot of shoes and boots with four to five inch heels. Just look at some of the pictures of me on this page; I hope you will see how much JJ my fabulous crossdressing guide has helped Kathryn to grow as a woman. Floral patterns and lots of pearls! A girl who knows where she is going, with a little help from her friends!

Dressing Service Kathryn

Kathryn Anne visited us at the dressing service and is wearing this elegant women’s light blue satin blouse

And what does the future hold for you?

This is probably the part that will be the most hardest for me. I have always managed to keep my dressing a secret from my partner up until very recently; and we have now split up. Perhaps I should have told her years ago: I shall never know. But I now look to the future optimistically with JJ as my crossdressing guide. I have many friends who are helping me go forward in my life as Kathryn.