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I put together my outfit and started getting dressed. I wore white bra and panties with black polka dots, pale black stockings, white satin camisole, grey business jacket, black pinstripe pencil skirt and shiny black high heels.
I couldn't go to work as Kimberley dressed like this so I called in sick to work so I could have the day off - a Friday. It took a few hours to muster up the courage to go outside even after Mum and Dad had gone to work because I am a closet sissy. Worse, I live in a cul-de-sac and everyone would be able to see me.
I finally went outside around 3pm, realising if I left it any later, Mum and Dad would come home from work, and schools would start closing. Parents would be out and about, children too.
I walked to the end of the road, turned left and left again feeling a mix of nerves and self consciousness at the loud click clack of my high heels and the swish of my skirt against my stockings. I've often worn the high heels when home alone, but the skirt I had owned for a few years but it had never been worn. I started to enjoy the way the skirt felt when I ran my hands over it and it had a slinky lining inside that made me feel sexy when I rubbed it against my legs and bum. I blushed bright red as I realised I was walking down the road and rubbing my skirt against myself. I crossed over and took a footpath to a bridge that crosses the main road and takes me towards a nearby canal. I took quite a few photos here. I turned onto the footpath that follows the canal and walked along here for some time. A few people walked past me, it felt like they were staring at me for the long minutes it took us to approach and pass each other. I could see the way they looked at me and it made me feel so self conscious. I came away from the canal on another foot path and crossed the main road at a pedestrian crossing, feeling so embarassed as I stood there. A young woman came up beside me, over a foot shorter than me as I stood in high heels and she wore flat shoes. I saw her looking me over and she made an expression on her face that said she didn't approve and I blushed bright red. Crossing the road I made my way home still trembling with nerves.
As I was walking down the road towards my house, my neighbour's daughter walked past me and I smiled to be polite. She responded with a smirk on her face that made me blush bright red and I could tell that she recognised me. I'm nearly home when a car drives past me and pulls up on the drive infront of me. I try to run across the front lawn to the door and as I got to my front door, I see that Dad had come home early. I could just imagine him looking at a business woman running up to his house and wondering why they have a key and then seeing the look of shame on his sissy son's face. I looked back at him getting out of the car as I turned the key in the lock and let myself in. I hurried inside and rushed upstairs to change out of Kimberley's clothes. My heart was pounding and I just managed to change into some jeans and put a jumper on over the camisole and pretend to be relaxed on the sofa while Dad locked the car in the garage before he came in the house and started asking about the woman on the doorstep. I then had to lie and say that no-one had been to the house and he must have been seeing things.
A few minutes later, I stretched my legs out and saw that in my rush to present myself as a boy, I hadn't put any socks on my feet to cover my painted nails and stockings. I looked down and saw that my chest was bulging like a girl's chest from where I hadn't had time to take off my bra, and had forgotten to take out my false breasts too! Looking in the mirror in my bedroom, I saw I hadn't taken off my lipstick either. I blushed bright red and felt so embarassed and humiliated that I didn't go back downstairs until Saturday morning and then had to face Mum asking me questions about the 'strange woman' Dad had (or hadn't seen), and she was looking closely at my face to see if I was wearing makeup. I also saw her looking closely at the hem of my jeans and could tell she was trying to see if I was wearing any nylon again.
My embarassment didn't end there as my friend reminded me of the full terms of the penalty and told me to make an account here, tell everyone what happened like I'd told her, and post the pictures to serve as my humiliation. If I didn't, she would post the pictures herself using an account under my real name.
I have been told to add that Kimberley lives in Woking, UK, and that she gives permission for her pictures to be shared and captioned. Please share this post around the internet and add captions here using my pictures so I can prove that my penalty is complete.
