Joanna’s First Time

My own first time was very late indeed. I was 24 and had a full-time job that I still have and my own flat. I had known that I wanted to crossdress for a long time, but had never done so.

As a child, I didn't see much difference in the girls I mixed with (though I was insanely jealous of their hair and dresses). My parents bought my clothes and took me to the hairdressers, so there wasn't a great deal of opportunity to express that part of me.

Also, my Mum's clothes were my Mum's, no chance of using hers, it wouldn't have been right. I did write stories about being zapped into a girl's body that dealt less with the physical changes and more with the wish-fulfillment. I find it interesting that none of them had the protagonist ever upset or simpering ― they were themselves as a girl.

In my teen years, I didn't even buy my own shirts because I was too scared of 'getting it wrong' so female clothing was out then, too. But I read about it and learned that it had a name, crossdressing. 

Around the age of 17 at university, I wore a pair of knickers for the first time that had been sent to me as a dare and to try and break me up with my first girlfriend by pretending I had a secret admirer. It didn't work, but I wore them a few times before finally throwing them out in disgust with myself. I had the biggest feeling that crossdressing was wrong, but without really understanding why. I struggled with this until I was 23. At this point I bought a pack of my own knickers (black and plain, full briefs) and wore them a few times to sleep and to make meals on an evening.

When I turned 24, a girl I liked convinced me to go back to her flat and try on a dress. It was a purple one with a corset-like bodice, scoop neck, puffed sleeves and a full skirt to the floor. I wore it over my actual clothes for the day and the girl tied the corset up in the back so that I couldn't take it off by myself. It was heavenly. It shimmered and flowed and I felt so right and at peace. It was a feeling I had never felt before. I could feel the skirt billowing, even though I wore jeans beneath, and the pull of the fabric on my shoulders (despite the shirt I wore). The color too ― it was soft and feminine and beautiful.

All the feelings about crossdressing that I had been struggling with for a good decade by this point seemed to melt away. I almost forgot about the girl I was with and when she told me to go and check out my reflection in the bathroom I did. She told me I suited the dress better than she did and, you know, I did feel that it suited me. I think she was being nice though ― she suited the dress better. My mind was in overdrive and my emotions all over the place. I couldn't think straight and I could barely breathe properly with the joy and the risk and the beauty of it all.

I was going to ask to borrow lingerie to fill out the top better, but my companion misunderstood my breathlessness and red face and asked if I wanted to take the dress off before the rest of her flatmates came home. She thought she was saving me from embarrassment and feared that she had made me do something I didn't want to do. I tried to stammer out that she was wrong, but it was too late. She undid the laces and hoisted the dress off me.

Afterwards, as we shared a coffee and I told her how I really felt in fits and starts because I just didn't have the vocabulary and was still trying to parse the whole sensation. But her friends arrived in the middle of this before I could ask to try again
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For me, then, my first time was very late indeed, much later, I would wager, than most people who have crossdressed. But it confirmed in me that it wasn't really crossdressing, though I couldn't explain that at the time. I was so comfortable and happy in my own skin whilst in that dress that I instantly started buying clothing that would emulate that; starting a wardrobe that stayed small but lovely and remains now, though none of those original clothes remain (they were all purged when I was 29).

Now I know what I was unable to express at the time ― I was not cross-dressing, rather I was showing outwardly what I felt inside. I was presenting as myself for the very first time. In short, I was me. As a consequence, that first time remains wistful, hopeful and full of wonder. It is lost forever, of course, the girl and I shared a brief relationship and my next relationship ended in marriage. She does not approve of nor understand my feelings on clothing and so there are precious few opportunities to embrace who I am. I miss it.

I invite all femulators to share their first crossdressing experience. Try to recall that moment the first time you tried on a woman’s garment and began the process of unveiling and exploring your feminine self. To entice you to share your first time story, I will give away a free copy of my e-book Fantasia Fair Diaries to all whose stories I use in Femulate.

Wearing Metrostyle.

Jeremy Stockwell as Dinah East in the 1970 film of the same name.