The First Time

 It's January 1978.  Two days after my 13th birthday.  In the family home in Helston, Cornwall.  My little sister is a very talented junior athlete and is attending a trial for the county junior cross-country running team. My parents have taken her to the event, some 40 miles away in North Cornwall. I have chosen to stay home alone. Because I have something I'm going to do. I've been thinking about and planning it for weeks. Looking for an opportunity. And now the stars seem to be aligning. 

My family leave home at 8.30am. They will be out until about 3.00pm. Plenty of time. From the moment I awoke this morning, I have felt giddy with excitement and also nervous. It's going to be a big day. The best day. Please let it all go well. 

At 9.30am I walk up the stairs in our little 3 bedroom, semi detached house on the edge of town. I head for the bedroom. Not my bedroom. The small box room that I spend hours of my time in. Not this time. I head for the master bedroom next door. My parents bedroom. The place where I hope to finally realise my dreams and find my happiness. 

I've been in this room many times before. I know where everything lives. I know which drawers and part of the wardrobe belongs to my Dad. But most importantly I know which drawers and wardrobe space contain my Mum's beautiful clothes and underwear. I've spent months opening them. Admiring the wondrous contents. Touching them. Studying them. Dreaming about them. And now it is time to fulfill my deepest wishes.

 

I open the bottom drawer of the large pine chest of drawers. My hands are shaking. My heart is beating a military tattoo in my chest. I feel light headed. I feel aroused like never before. A new sensation as a 13 year old boy.

Inside I see the familiar sight of my Mum's underwear. All of it is foundation or shape wear, as I have learnt it is called from looking at the lingerie section of the John Moores home shopping catalogue that arrives twice a year. Once upon a time I would eagerly await it's arrival to look at the toy section. But for the last two years, the clothing sections have drawn my close attention. The women's clothing pages that is. My friends do the same. They look at the lingerie and underwear section, just as I do. But I look at so much more. I look at all of the women's clothes. And dream and hope and wish. And know I am here. My Mum's bottom drawer open in front of me as it has been so many times before.  But this time is different. 

This time I'm not just going to look and caress and feel the gorgeous underwear. I'm going to wear it. And I know exactly what I want to wear and how to wear it. I've spent years watching my Mum getting dressed. She has never been shy about being seen in her underwear by us family members. Of course this has changed as I have become older, but it's still etched in my mind.

A few months before, I discovered what I was, when I saw an article in the Sunday Observer, about men who dressed as women. It called them transvestites. I had looked it up in the dictionary. I knew that I was going to be a transvestite. It was my destiny.  And now I was ready. 

I carefully took a one piece, white Playtex corselette and gazed at it. Ran my hands over it. I even smelt it. It was beautiful. I felt a tingle down below. It was all so exciting.  I also took out a pair of tan tights. 

I quickly shed my boy clothes, and with shaking hands, pulled on the gorgeous corselette. I felt a thrill of exhilaration as the straps snapped over my shoulders. I dared not look in the full length mirror on the wardrobe yet. I pulled on the tights. The feeling on my legs was incredible. Like nothing I had ever felt. I went into my bedroom and opened my underwear drawer. I took out a few pairs of socks and placed them in the breast cups of the corselette, to create an impression of a womanly bust. Finally I returned to my parents bedroom and opened up the wardrobe. On a shelf at the top was something wonderful. My Mum's wigs.

My Mum had two wigs she sometimes wore on nights out. She had an auburn and a blonde one. In a similar style to her own hair, a typical bouffant wavy perm that was made popular by Elizabeth Taylor. My Mum's hair was brown, but she liked to have a change now and then. My Mum was still quite glamorous in the late 1970s. Not many boys trying on Mummy's clothes for the first time are lucky enough to have a choice of gorgeous womanly hairstyles. I was in heaven. I chose to be a redhead. My Mum had a friend who was a famous actress and she had similar hair and I had always admired her look. I put the wig on and then walked over to the dressing table.  

As I caught my first glimpse of myself in the mirror I let out an audible gasp. I looked like a woman.  I needed to adjust the wig a little but once done,  I saw a pretty woman staring back at me from the mirror. Surely it wasn't me? I smiled. The girl in the mirror smiled back.  Suddenly I felt a wave of emotion flood over me, and I felt tearful and shaky. There was just one thing left to do.

With trembling hands I opened a drawer in the dressing table. Here my Mum kept her make up. I selected a deep red lipstick by Max Factor. I had seen my Mum applying her make-up so many times. I knew exactly what to do. I managed to still my shaking hands and applied the lipstick perfectly. I was clearly born to do this. Just one thing left to do.

I approached the full length mirror slowly and nervously.  Then I closed my eyes.  I moved carefully in front of the mirror and then counted out loud to three. On three I opened my eyes. 

I was almost overwhelmed by the emotions that washed over me as I gazed at myself in the mirror. A young woman was stood before me, staring back at me. It just felt so good. Like nothing I had ever felt before. I felt a sense of excitement, but also completeness. This was me as i had always dreamed of being. The girl that had lived inside of me since I was little had suddenly appeared as a beautiful woman.  I was quite good looking in my youth and I looked very pretty as a young red headed woman. I was complete.

I spent an hour dressed, just enjoying the thrill and the sensation and the sight of myself as a pretty young woman.  I spent some time looking through my Mum's wardrobe.  But I decided to leave trying them on for another time. Hopefully there would be another time. I hoped my sister did well enough in her running trials, to get selected, which would mean more chances to dress.

I glanced at the clock. Nearly 1.00pm. Time to get undressed and carefully put everything back as it had been.  I had taken my Mum's underwear out of the drawer on many occasions before, so I was well practiced at putting them back just as they had been. I definitely was a natural born transvestite.  I was back into my boy clothes, lipstick removed and Mum's clothes and wig safely stored away by 1.30pm.

I knew that I had just had a life changing experience and that I was going to be doing this forever.  Just after 3.00pm my family returned home. Good news. My sister had made the county cross-country squad. There would be more Saturdays like today. 

I was so happy and also a little overwhelmed by my first experience of crossdressing. I had never expected to feel so happy and so complete.

I was on my way as a girl.  And ready to spend a lifetime as a transvestite.