The Consequences of Being Caught

I was caught cross-dressing in my early teens a few times and those feelings associated with it have stayed with me ever since. Shame. Guilt. Fear. Humiliation. All those emotions that can cause harm to youngsters. The first times were by near neighbours. The first was a woman in her 50's who suddenly came out as I dared to walk up my garden path whilst all femmed up. I was too caught up in the moment to hear the door and notice her approaching. Her look said it all to me. It was a mixture of shock, disgust and pity. She knew me, she knew my family, she knew everyone around me.... and it terrified me to know this. What the fuck had I done?

I don't think she ever told my parents but I'm pretty sure she told some of her friends and other close neighbours. I could tell by some of their looks as they passed me. The thing that convinced me was when I was walking up for a bus one day and one of my other neighbours was hanging out of her top window as I approached. I saw her and as I got closer said "Hello" to her. She smiled down at me and said "Not wearing a skirt today then?"

I was dumbstruck. She had always been a friendly chatty woman and to hear her say this to me was like a punch in the stomach. I laughed it off and carried on my way with my mind in overdrive. She had never seen me so it must have been my neighbour who told her. Fuck. Fuck. Fuck. Fuck. Fuckity fuck....

Over the next few months I was caught more and more. Always by women.  I hadn't left school yet but had time off before exams started and school finished. I spent it wisely by experimenting with my mum and sisters clothing. I'd try on all types of combinations for a look that I liked. My first favourite was a pair of my mum's black tights, bra and panties coupled with my sisters skirt and blouse. A pair of mother's strappy heels and I was all set to go.

I loved to prance around the house admiring myself in the mirror before eventually giving in and coating my belly in jets of my warm cum. After some months this wasn't enough and I had to increase the thrill factor. This was done by getting all dressed up, going upstairs and looking for people approaching. I was waiting for strangers to walk my past my front door and then I'd come out the door just as they passed so they got a good look at my long shaven legs in high heels. I stuck to women and girls only. I wanted them to see me as their sexy sister. I was good enough to pass as female and I wanted them to see a sexy woman - or my idea of a sexy woman as dictated by the porn mags of that day. High heels, short skirts, tight blouses, stockings.... I guessed no-one knew me so it didn't matter. How naive was I? The place I stayed in wasn't small but it wasn't huge either. Men didn't interest me so I never bothered with them and to tell the truth I was scared one might get violent towards me. I couldn't risk that happening at my front door. That was way too risky....


Then one day I spotted a girl approaching as I watched from upstairs and so I dashed downstairs to rendezvous with her just as she passed my house. I ran down the stairs in my high heels and quickly composed myself and the mirror by the door. I smoothed down my hair, gave my make up a quick check, blew myself a kiss and swiftly opened the door and stepped out to look around. Oh my fucking God. I couldn't believe it. In my hurry to show myself off to this girl I hadn't looked properly and I'd made a big mistake. I knew her. It was Lesley. I knew this girl from school and she knew me. She knew the boy me. She also now knew the girl me. She had stopped in her tracks expecting me to come out of the door as she heard it open. Instead, of me, my as yet un-named female alter ego stepped out. I was all in black that day - skirt, blouse, heels, tights - and had my hair made up in a very feminine style. I'd clip on earrings in and, as usual, was wearing lipstick, mascara and eye shadow. I was to those that never knew me a slightly slutty looking girl. However, this girl knew me.

"What the fuck....." she exclaimed and again her face said more than her voice ever could.

I was caught bang to rights and knew it. My world crumbled around me as I realised who it was. Oh shit. Why Lesley? Why hadn't I looked more closely? Lesley was quite possibly one of the most beautiful girls at my school. To have this beautiful girl look at me as I stood in front of her all dressed up in sexy clothing was mind numbing. After a few seconds of silence on my behalf I turned on my heel and ran back in the house slamming the door. Behind the door I collapsed to my knees leaning against it as my world turned upside down.

 I still know Lesley- she's on my facebook - and she is still stunning even in her mid 30's. She has lost none of her natural beauty and when we see one another out and about we still chat. None of the two of us have ever mentioned that day ever again but she absolutely 100% knows my dirty little secret. Every time we talk it is in the back of my mind and it turns me on immensely. It used to scare me just after it happened. I would do everything I could to avoid speaking to her such was my shame. Now... now it gives me a semi. Go figure.