Who remembers their first time being dressed as a girl? Mine is as clear as if it were yesterday, and the consequences........well they stay with me 40 years on!
When I was around seven my mother decided I was too pretty to be a boy, and to emphasise the point, one night , instead of getting me to wear my pyjamas, she made me wear my sister’s nightie. This was bad enough, but then she thought it would be “nice” to show the neighbours what a pretty boy I was – and took me to the front door to show everyone. From then on she regularly made me wear a nightie as a “punishment“ for some minor transgression or other, much to the amusement of my two bigger brothers. She also made me wear frilly knickers and lacy vests under my school trousers and shirts, and occasionally, I was required to wear dresses or skirts for the whole day – but thankfully I was confined to my room on these occasions
We lived in the same house for many years, and when I went to high school I found that my neighbour Mrs T was the French teacher. I hoped and prayed that she didn’t remember my “Nightie” display. But one day in the third year at the school when I was 14, she offered me a lift home – it was a small community, and there was no problem accepting a lift from your teacher. My parents both worked full time, so we kids were expected to look after ourselves for a couple of hours after school. Mrs T was aware of this and invited me into her house. As soon as we were indoors she asked me if I remembered the “nightie“ event. She tried to say it in a jokey way, but I wasn’t so sure. I pretended not to know anything about it (even though I had actually been required to wear my nightie on the prevous night for failing to do my homework). She knew I was lying and said she had something for me. She took my hand and led me into her bedroom. I was absolutely terrified, but at the same time totally transfixed. On entering the bedroom she pointed to the bed, and told me to sit down on it. Then she went to a chest of drawers and took out some items of clothing. I felt my face go redder and redder as she held up a satin nightie in pale pink with white lace trim.
What do you think?” she asked. I know you wear nighties, as I have seeen you in your bedroom window. I tried to act indifferent, but I could already feel the heat from my cheeks. “I don’t know what you mean” I said. “Do you like it?” she asked. I didn’t know how to respond, so I just said “very nice”. “would you like to see it on?” she asked. At this point I didn’t really realise what she was asking – but then she added – “on you”!
“Um, I, well, er, if you like”, I stammered. “Oh no, if YOU like”, she replied. “Why don’t you take off your school uniform and try it on, I won’t look – ‘till later.” I gulped and nodded, somewhat lamely. What else could I do, she knew I was “dressed up” regularly – so I was terrified she might tell some of my friends.
Mrs T left the room, and I slowly got up from the bed and started to undress. I can’t describe the feeling, a cross between total fear and utter exhilaration. Until this point, althoughI had been forced to wear girl’s clothes regularly, I had never dressed myself. As I let the satin slip over my head and body, I felt the most incredible sensation, and for the first time was aware what a wonderful gift I had been given by Mrs T - that dressing up could be fantastic.......