Knowing that no jeans or cargo pants are allowed in the office, I’m left with two options… one; pull a sickie, or two; wear something suitable. I knew that my aunt would flat refuse to let me pretend to be sick and take the day off, which really gave me only one option. I figured that the shift dress was a little more conservative and a little less girlie than my short grey A line skirt. I wore it with a blouse and although she said I looked OK, Aunt Katinka wasn’t keen on the pointy collar. She loaned me one of her blouses which has a round collar, trimmed with a narrow band of lace. Once I had that on, Aunt Katinka was satisfied. I wasn’t so sure but with the clock ticking, I didn’t have time to try yet another blouse. I pulled the same tan tights I’d worn on Saturday up my legs, and slipped my feet in to my loafers. I checked my reflection and couldn’t believe that I had to go to work like this. “What are people going to think!?” I feared. Then after a moment’s thought and staring at myself, I realised that they’re not going to think anything they don’t already think about me. At least with the shift dress on, they can’t see my bra through my blouse… and the one my aunt has loaned me is far more see-through than any of my others, even the outline of my arms can be plainly seen through its long sheer sleeves. As inappropriate as my attire is, it’s the best I’ve got under the circumstances. I pushed my arms through my jacket sleeves and hunched it on to my shoulders. I picked up my handbag and had a long hard stare at myself. “You’d better hurry if you don’t want to be late.” my aunt advised. “Have you got a spare pair of tights?” she asked, glancing at my legs. I hadn’t, but didn’t have the time to worry about such trivial matters. “You need spare tights William!” my aunt told me, before going to fetch me a pack.

I opened my handbag and rummaged around, panicking that I’d lost the USB stick which held the small amount of work I’d done last night. I found it just as my aunt returned. “Thanks.” I gulped as she gave me a brand new pack of tights. I put them in my handbag along side my sandwich and zipped it shut.

Before I left, my aunt put her hands on my shoulders and looked me square in the eye. “Be confident William… you belong in that office.”

“I will.” I replied, gulping and forcing a smile.

I turned and took a deep breath before opening the front door and stepping into the outside world. It’s by no means the first time I’ve stepped out of my aunt’s front door wearing a dress, but it’s the first time I’ve done it as an adult and the first time I’ve done it alone.

I certainly turned some heads as I walked to work that morning, much more than usual. I don’t think it was so much the dress itself, but the combination of that and my loafers… they really didn’t go! I made the mistake of glancing at my reflection as I passed a large shop window and realised just what is turning all those heads… it’s not my ill-matched footwear or my corporate frock, nor is it my feminine black jacket or leatherette handbag, as perched on top of everything is my unmistakeably male head. I’d have felt better if I’d gone the whole hog and worn make-up and maybe a wig too… but I know nothing about make-up and so far as I know, Aunt Katinka doesn’t have any wigs.

In a way my clothing is the least of my worries on this overcast Wednesday. I’m behind at work and got little done at home, meaning I’ve got my work cut out for me if I’m going to get yesterday’s task completed by lunchtime. No matter which way I look at it, today isn’t going to be a good day. I tried to be confident as I stepped into the office. The women coed, some clapped and some laughed. The men snorted and sneered, some threw me looks that might kill whilst others made a point of not looking at all.

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