I have been dressing for goodness knows how long and have my own extensive and varied wardrobe and with the help of some of my girlfriends in the make up department can pass quite convincing for a woman.
Going back a few years I was working for a small independent company selling goods and services to various clients in the property sectors across the country. I was based in London and my boss, Sherri, was an attractive woman in her mid 40s, older than me by about 10 years. To be fair she was a good boss and treated me fairly.
I didn’t at that time go to work fully dressed as a woman, in fact I was still pretty much in the closet as they say. But I did tend to wear clothes that were in between male and female and always wore nice underwear and stockings.
One day in the office I was doing a bit of tidying and moving stuff around and the likes. Getting a little hot, I removed my jumper. I was wearing a blue blouse underneath with a spaghetti strap Cami top underneath. I didn’t think too much about what I was wearing as I thought it was quite conservative and as I said in between male/female in appearance.
About 10 mins later Sherri called me to her office and asked me to have a seat. I was a bit taken back by this as I was confused thinking what have I done wrong. Anyway, she proceeded to inform me that she had suspicions that I was often dressing in woman’s attire when at work and today her suspicions were confirmed, as she had seen the outline of my underwear whilst I was working.
At that point I found myself becoming a little embarrassed and blushing. She immediately notched this and apologised saying she didn’t mind me dressing and I shouldn’t be embarrassed about it and just wanted to tell me that I was not being as subtle as I thought and the other girls in the office had made comments in the past.
Anyway, what seemed like a very long time in the office I then left and although it was on my mind most of the day, it soon past and I went on with my usual routine. About a week had past when one evening I got a text message from my boss informing me that I would be the only one in the office tomorrow as the other two girls and Sherri had to go to a client’s site in Manchester and would not be back until the following day and could I just basically answer the phones, do emails etc.
I found this an opportunity to live out one of my fantasies and be the sexy secretary in the office. I decided that night I was going to have a fun day on my own in the office fully dressed head to toe as female me. I planned what I was going to wear that evening and opted for a leather pencil skirt and sheer white blouse and below that (to add a bit of old fashioned classical style) a black midi silk body slip with black heels, and I opted to wear a straight shoulder length chestnut coloured wig.
In the morning I dressed as normal for traveling into work and had my female clothes in a small day bag and underneath I was wearing a black bra with matching thong and fully fitted suspender belt with sheer seemed stockings. I must say just wearing this made me feel rather sexy and flirty.
I got to the office around 8:30 and did all the usual stuff to set up for the day and then proceeded to finish off my look by putting on some makeup and getting dressed in my female attire for the day. I wasn’t long before I was in the ladies toilet looking in the mirror admiring my work. I then went to the office to do my days’ work, the way I had always dreamed of being at work fully dressed as female, undertaking my secretarial work. I must admit I felt excited and comfortable in my new world and as the time passed, I just found myself getting so relaxed in my new working environment. To be honest the only thing missing was a man using me as the slut, I wanted to be and fucking me on my work desk.
Unfortunately, the end of the day was approaching, and it was time to transform back into male mode for my commute home. Or was it. As I was looking to get undressed to depart, I said to myself I can do this and out of the blue I found myself locking up the office and leaving for home fully dressed as a female.
Nervously I walked to the tube and noticed that everyone was caught up in the commute to notice anything I quickly settled down and relaxed. It was quite a squeeze on the commute and found myself literally face to face with men and women on the tube and being squeezed and pushed with people getting off at the various stops along my short journey underground. I found it so exciting I could have screamed out with pleasure.
It was then time to get off the tube and on to my train home and as I was traveling up the escalator to get to my platform, I couldn’t help but notice the looks and smiles I was getting from the guys coming down the escalator in the other direction I was even passed a telephone number from a guy asking me to give him a call. Cheeky.
I eventually got on my train and sat down and got comfortable for the 40 minute commute home. The train again was starting to fill up when a woman came and sat across from me and sat down looked at me and gave me a great big smile. I though, that’s weird. As the journey started the train was slowly emptying and the woman across from me started to chat to me, my replies were limited to one word or just a smile for fear of her finding out through my voice that I was a man. To my shock she causally smiled and said to me you are extremely convincing you know. Well, you could have blown me over with a feather.
It turned out that she was also a man in transition, she said to me as soon as she walked on the train and looked at me, I knew your secret. When I enquired into how she could tell she just smiled and whispered to me… I looked to sexy to be anything else. Blush. At that point my stop had come, and I stood up to get off and Debra (the ladies names) said she would see me around and to always get on the third carriage when traveling so we could meet and have a chat. I agreed and got off the train to walk the short distance home.
When I got home my head was spinning, I think it was the sheer excitement of the day, so I decided to pour myself a very large glass of wine and wind down for the evening. My phone rang and I answered, it was Sherri, asking me how the day went on my own and did I cope ok. I told her it was ok (God if she only knew) and everything went according to plan. She finished and asked me to come and see her first thing in the morning as she had something she would like to discuss with me, but not to worry. Well worry I did all night. Why do people say that.
I got into the office that morning as normal and once I had taken my jacket off, I went to Sherri’s office, knocked on the open door, Sherri looked up from her laptop, smiled and told me to come in and close the door. She thanked me for covering yesterday on my own. I responded by saying it was my pleasure at which point she replied… I guess it was for you! Confused, I asked what she meant. She asked me to come and look at her laptop screen, as I walked over to her desk, she turned her laptop towards me and on it was a video of me in the office fully dressed in my sexy secretary look from the previous day. It turned out that Sherri had CCTV in the office that I didn’t know about. TBC.
