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First steps on my mtf trans journey: experiments in cross dressing

If you’ve read “In the beginning”, you’ll have an idea of my early realisations that my number one dream was to be a girl, but that I wasn’t one.
Sad times 😢
And at the time, there didn’t seem to be much I could do about it anyway.
By the time I was in my early twenties though, I had my own place and freedom to experiment.
I still couldn’t “be a girl”, but I could at least dabble with “being like a girl”.
The best way Of being like a girl that I could think of, was dressing like a girl.
The first thing you do when getting dressed is underwear, so why not start there?
Also, it’s the most different and purely feminine and intimate and I was (and still am) fascinated by lingerie.
And, one can secretly wear it under male clothes and no one will know.
I had tried out bras and knickers and tights and skirts and dresses in secret when I lived at home (sorry Mother!).
Now it was my time to have my own things.

Buying lingerie for the first time 

And I wanted something special and really feminine just for me.
From my earlier browsing of the lingerie catalogues, purely for research you understand, I had a good idea that I wanted something like a teddy or bodysuit (which is what they were called back in the day, now either bodyshaper or just a body). Why? Because they were so very different to what I would wear as a boy, because I’d never tried one, because it is combining bra, knickers, the body, waist. Because it’s clingy and tight. Sexy and feminine. Pretty. You get the idea.
I don’t recall why one day I decided to make it happen but one day I did. I left the office at lunchtime and went to Marks & Spencer.  Shopping for lingerie and being conspicuously not a woman was nerve wracking and still is actually but excitement overcame fear. I wasn’t sure quite what to choose exactly from the different types and styles so I went for the prettiest one. It was white, padded cups and pretty trim around the legs and over the cups. All afternoon at work I was scared someone would find out what I had in the bag under my desk but equally couldn’t wait to get home and try it on. Anticipation was intense: my first lingerie of my own! Not much in life lives up to expectations but this is the one thing that did.  It really did!  Oh my, when I first put that body on it was so lovely and sexy and I felt so girly and pretty. Fond memories ☺️

Expanding my cross dressing wardrobe 

After that, I began to indulge myself and try new things. I got different styles of bras and knickers, tights and stockings, a dress and a skirt, leggings, cycling shorts, a leotard, a lovely swimsuit and a pretty silk shorts/cami set to sleep in.
But it was all just my secret when home alone. I could hardly go the the pool in my swimsuit so I used to wear it in the bath!  I didn’t dare go out as me, although I did sometimes wear my clothes under male outerwear.
Experimenting was fun though and I was becoming more comfortable with my feelings about myself.
Not everything was a success. I wasn’t comfortable to try things on in the shops then, so some of the sizing was a bit off but it’s all experience!

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