Years ago I lived in a flat in London and whilst my landlady was away I was forever dressing in both my GF's and my landlady's clothes as well as my own girly clothes. Later my landlady found out about me and that was great because I could then wear women's clothes all the time I was at home and sitting watching TV with both my GF and landlady whilst we were all dressed as women was absolutely fabulous.
However, my GF at the time started to get quite anti me dressing, especially as I was pushing the boundries more and more such as make-up and nail varnish. Anyway, she drew the line at me going out with her dressed, apart from one night when I convinced her to let me walk around the block with her from her parents house (they were not there) whilst in a skirt, tights and high heels.
So, there I was with a terrible urge to dress and go out and no oppotunity until one month when my GF went off on a foriegn trip and my Landlady was on holiday abroad. I thought of what I wanted to do and planned it for days if not weeks before. I had noticed whenever I got the chance to dress up at home alone in the mornings (I used to get up really early to give myself as much time dressing before work as possible) that there were a couple of women who would walk past my house on the busy road that I lived, about the same time everyday.
One day I was in full makeup, a blouse, a red short skirt, white lacey tights and heels and as I saw them approach the house I slipped into the communal hall of my house, opened the front door and as they past the gate of my house, I knocked over a couple of milk bottles deliberately. The women turned automatically at the noise and I was putting the bottles back up and stood up, knowing that they could see my tights and skirt and hoping that they thought I was a woman myself. It was fantastic to think that they had seen me and of course I had to relieve myself as soon as I was safely back in thinking about being seen dressed. I wanted more of this.
So with my GF and landlady away I hatched my plan. One morning I got up really early, probably about 3:30 in the morning. I then proceeded to have a really close shave and then once ready I put on my make-up, being very careful to do a great job. When I finished I looked at my reflection and seeing the foundation, eye liner, eye shadow, mascara, lip liner and lipstick and blusher all put on as expertly as my GF had showed me to do, I saw my sister stare back at me! We looked very alike and with make up on I was a spit of her. Satisfied with this I went back to my room and put on white panties, white bra (stuffed I recall with panties to give me a breat form), a cami and the put on some blue lacey tights. Then I put on a blue blouse and a blue knee length stretchy skirt that my GF had given me. Then slipping on my 2 and half inch heeled blue court shoes I walked into my landlady's room and took out a knee length soft coat also in blue though a shade darker than my skirt and put this on. Taking a shoulder bag from her wardrobe, I put my keys in it along with a lipstick and went into the front room and after turning off the light I opened the blinds and sat smoking watching the road, my heart beating fast.
When I saw the two women approaching as I hoped they would do, I ran to my front door and opened it into the communal lobby, scared that the people upstairs might be up at that early hour. They weren't, so I slipped across the short hallway and opened the front door. The cold air hit my legs and I was thrilled, but in that split second I could either turn back or go on..I went on!
I stepped out onto my path and walked quickly to the gate and looked left, the women were a few yards down the road and with fear in every pore of my being I set off after them the sound of my heels clicking on the road was both load and beautiful. Within no time I had caught up with the women and as I walked next to them they glanced across to me. For that one moment I was walking with two other "women" all together - I was in heaven. I walked faster than them so was soon in font of them however and for the next 20 yards I was in front of them and knew that they could see me in my coat, tights and heels, coat on and bag over my shoulder. As I turned left again to get off the main road, a black guy was coming out of the road I was entering into and we almost bumped into each other and I said "sorry" in the most girly voice that I could. I then walked around the block and back home past my local shop where I saw the owner getting ready for the day..I was so excited to be doing this! I eventually made it back home, elated.