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Click on Tilly’s portrait below to go to her Flickr  page.  


  I first wanted to dress as a girl when I was 6. I remember fantasizing about dressing like my mother,  envying my little sister that she was allowed to play with my mum’s makeup and dress up in her high heels and dresses. My mother asked me if I wanted to play too, but I was too embarrassed to say yes. I so regret that I did.

I first dressed as a girl age 12. I used to bunk off school and wear my mum’s clothes and try on her make up. Once everyone else had left for school/work I would give myself half an hour to make sure no one was coming back and then go through my mother’s drawers and assemble my wardrobe. Tights, bra, her pantie girdle, lipstick, powder, nail varnish, a skirt, and best of all her high heeled shoes. I loved how difficult bras and stockings were to put on, loved how elasticated and firm my mother’s panties were, just how hard it was to walk in heels and how difficult to apply makeup. It sort of gave me a goal – achieve feminine perfection no matter how difficult and challenging it is to achieve. After dressing up I would ruefully take everything off and replace it with great care exactly where I had found all my mother’s things. I wonder if she ever guessed?

My fantasy was that one of my teachers – a very strict, classy and well-dressed woman whose auburn hair was in a bun and who always wore patent leather stilettos and who I found very sexy – singled me out from the class to have make up lessons and be feminised. Ever since I have loved the idea of a woman feminising me. Not that she ever did….

As I went through my teens I discovered sex, girl friends, became very vanilla and sort of left crossdressing behind, but when I left home and lived by myself  and I had the freedom to dress- well it started all over again - albeit not very well. I bought my first women’s clothes and make up and had my first makeover.

I am lucky – I was a small and pretty boy and have grown to be a slight adult. I can pass as a girl.

The watershed moment for me was discovering the long discontinued World of Transvestism magazine. There were other people as well as me with this kinky compulsion to dress as women - I WAS NOT ALONE. It was such a relief! And studying all the photos I thought I can pass as a girl just as well as some of these.

Then along came the internet. I didn’t think I was gay or bi sexual (I liked girls too much; so much that I wanted to be one…) but when I discovered that guys fancied girls like me I crossed another watershed. Girls dress up to attract guys. Why don’t I do the same? So I did, went to clubs, got picked up, lost my cherry – and realized that sex as a girl made me feel SO feminine. And that as a girl, I fancied men.

I read the Story of O when I was about 16 and thought wow I want to be like her. I wanted to be a submissive girl.

I saw The Stepford Wives movie a few years later. It is a crazy and slightly repellent film, but I realized that its portrayal of femininity was a picture of the kind of woman I yearned to be – pretty, beautifully groomed and utterly obedient. I still would love to find a husband – or a mistress - who would make their bimbo princess sissy Stepford Wife. Ever since seeing it I have loved retro fashions – A line dresses or pencil skirts that make a girl mince, ultra high heels, blonde wigs, false eyelashes, red lips. Long nails – the ultra-feminine works is what Tilly aspires to – as long as I look pretty and feminine. I have never done drag.

I am a girly girl.