Crossdressing Secretaries

Feminine, glamorous and a secretary for the day, how fabulous would that be with Dress Me Up? I am offering a special day rate for crossdressing secretaries. I have decided that any young lady may come along to be crossdressed by me into a stunning crossdressing secretary, one of my many crossdressing secretaries. Hair and make-up will be done immaculately to become my personal assistant or secretary for the day. The day will start at 11.30am and go through until 4pm; all clothes, hair, make-up etc will be supplied and applied. You will be asked to do some secretarial duties as well as tidying up my lingerie wardrobe and sorting through clothes, panties and bra’s. You will serve a suitable lunch of sandwiches, tea or coffee and generally talk about girly things, the latest copy of Vogue and what colour nail polish is trending at the moment.

Imagine that I have a temping agency and as a highly qualified secretary or personal assistant you are employed to make sure your appearance and administration skills are second to none. As one of my crossdressing secretaries that temp for my agency you are posted to a large corporation, you work in their office as a secretary or PA; no one knows you are in fact just one of my many crossdressing secretaries at the agency. You take your work very seriously and sometimes you are asked to accompany the boss to customer meetings or help out on the customer service desk where you must always look your best. Ultimately feminine from your lingerie to your silk blouse and pencil skirt there are always female co-workers that roll their eyes as you pass the copying machine and tut at your seamed stockings and stilettos.

Taking notes on important projects and typing them up can be quite difficult with your long scarlet red painted nails but just as any of my crossdressing secretaries you have mastered that so impeccably. Of course you know exactly which top coat of nail polish works best for you, so your nails do not get chipped or damaged, not forgetting the matching lipstick. Always wearing stocking gloves when putting on your silky nylon stockings, oh goodness there is so much to learn to be one of my perfect crossdressing secretaries. Please note that all the clothes, blouses and skirts that my crossdressing secretaries are wearing are all available to wear at Dress Me Up.

Crossdressing Secretaries First Day by Miss Pink

You know you have always wanted to be a secretary and have often admired the girls on their way to work: particularly those who clearly have made an effort with immaculate hair and makeup walking in the highest of heels. Well now your dream can come true at Dress Me Up where you will be transformed to that lovely girl who sits behind her desk, answers the phone and gossips with all her friends. The dress code at the office is strictly smart business attire (no trousers) given the number of clients and visitors attending meetings and discussions.

In the past girls have been sent home as they do not look professionally attired and well presented. You will be required to start work at 11am and work through until 4pm performing various secretarial duties for the business which is in the fashion industry. Knowledge of current fashion trends, colours and styles is required and you should read the latest copy of Vogue before attending as you will be asked questions about it on the day so bring your copy with you as well as your preferred colour of nail polish.

I arrived nervously for my first day of work not sure what to expect but very anxious to please and be offered a permanent position as an administrative assistant. My new boss was a woman so I knew I would have to look my best. I was pleased therefore to have spent the day at Dress Me Up by way of preparation for the big day. JJ had taught me so much and I put that training to good use before leaving for work.

I set my alarm early after a good night's sleep, ran a warm foaming bath and bathed my smooth body all over with the perfumed water. I chose a cream pair of panties with a matching bra which was very delicate and lightly padded to show off my breasts. I chose nude hold up stockings and drew them up over my smooth legs admiring my pink toes which I had painted carefully to match my finger nails the night before.

Sitting in front of the mirror I applied a light foundation and chose a light brown eye shadow before adding eyeliner and lots of dark mascara. Lightly blushing my cheeks with blush and applying lipstick I chose a delicate pair of pearl earrings, my ears had been pierced for the first time last week. I placed a very classy pearl necklace around my neck before brushing out my long blonde curls.

I applied a sweet delicate perfume on my neck and wrists and a simple gold jewelled ring on my finger. I reached into the wardrobe and put on the stunning silk ivory white blouse. There were four buttons on each cuff and I loved the look and feel of the silky material. A classic black short pleated silk skirt next with a simple black belt around my waste. It was a lovely sunny day and I chose my prettiest pair of sandals with a very high heel. I knew I was being looked at as I walked nervously along the street to the office building.

"Good morning Miss Pink" said my boss. "Please come into my office, I have some typing and filing for you and I really need a cup of tea" Did you read the article in Vogue this morning with the fashion section on summer dresses? Please write a short summary about it for my meeting later this afternoon. Love your blouse by the way. Now run along”


'Who said, dreams can't come true?'