My feelings were not helped by the silky pink nightdress that I had had to wear to bed that night. Used to pyjamas, boxers, or just being in the buff, the feel of silk clining against my body was strange and I looked just like a girl. Albeit a very big one. The flowing silken, lace trimmed garment was the first feminine garment that I had ever worn.
After I had showered and donned a pink fluffy bathrobe, Milly took me in hand. I was astonished at her sudden take charge manner. My hair was her first target. I had deliberately allowed it to grow into a long mane, like that of the king of beasts, the lion. Milly, a hair stylist amongst her many other talents, set about taming it. She washed it, cut it and shampooed it. Then she used straigtheners to give me flowing tresses that came down to my shoulders and which framed my face. The result was I looked more womanly. From the back, I would look just like any other woman.
With my hair sorted out, Milly produced a bottle of perfume and proceeded to liberally spray it all over my large body. An overpowering aroma of tiger lily and jasmine assaulted my senses. This was how I would smell to others.
Next came my new clothes and I was confronted by an assortment of garments that were familiar, yet at the same time utterly alien. I was handed a bundle of white lace and it took me a moment to deduce that these were my new underwear. Ladies' knickers! Fighting back feelings of shame and humiliation, I put them on. They were a lot tighter than any of my male underwear, but then they were designed to be, to show off my rear and to provide a pretty cover for my most intimate area.
I was next given something even more symbolic of womanhood. My first bra. With help from Milly, I put the lace contraption around my chest. Once the clips had been done up expertly by Milly, the weight of my breasts became a lot easier to bear. Still, it was very peculiar to find my chest, shoulders and top back covered by this lace support garment.
Instead of the corset that I had worn the day before, I was put into what Milly called a waspie. And boy did it sting! A white elasticated band, festooned with lace trimmings and attachments for stockings. The waspie did the same job as the corset of pulling my waist in, but was much smaller, and allowed me to experience wearing the bra. It was uncomfortable to wear though. I would have to wear this thing, and the strange bra, all day.
A pair of black stockings with black lacy tops was handed to me and Milly showed me how to put these on and attach them to the suspender tabs on the waspie. Soon my legs were sheathed in nylon, save for a small amount of bare flesh at the top of my legs. The stockings felt comfortable, but it was odd to be wearing them.
And that, Milly said, concluded dressing me in my foundation wear. Now for my outer clothes. Much of my underwear and stockings would be hidden from the eyes of the rest of world, thank goodness. Milly was in her bossy mode and she picked out my outfit for me.
I had to put on a flowery top with puffy sleeves that left two thirds of my arms bare. It also exposed the tops of my shoulders and revealed my bra straps. Most disturbing of all, and something I was still not used to, was the sight of two mounds in my chest region. The material of the top was silky and clingy. I was experiencing some strange, sensuous feelings.
Then I had to put on my suit. Not my normal man's suit, but a woman's jacket and skirt combination. I had to step into a pinstriped skirt with a slit up the back to expose more of my stockinged legs. The skirt fitted tightly around my lower body and especially around my bottom, which would be prominent and on show for all to see.
It was very weird and, for a man as masculine as me, very humiliating to suddenly find himself in a skirt, one of the most obvious symbols of femaleness. Parts of my body that had been hidden from view by male clothing were now on display.
I slipped on the matching jacket, noting the different cut. It had been designed to adorn and flatter a female form. Of course, with my breasts and my small waist, it fitted me well enough. Milly slipped a thin leather belt around the waistband of my skirt. It had a buckle in the shape of an oversized golden butterfly. The belt further emphasised my womanly waist.
Milly handed me some accessories to wear with my new outfit. A slender silver ladies' watch with a tiny face, a pair of diamond clip on earrings and a silver band necklace. Milly helped me put these on. The feeling of wearing earrings was entirely foreign to me, as well as jewellery in general.
Milly then sat me down at her vanity table and proceeded to apply my make up. A thick layer of foundation that softened and blurred my naturally masculine features. Milly then put on eyeliner, mascara, eyeshadow, blusher, lip liner and finished off with a deep red lipstick. The cosmetics she was using, Milly told me, were the best in the business.
I submitted to having my face altered and painted with the best grace that I could muster, but I was finding it shameful and demeaning. Men should not wear make up, that was for the ladies, had been instilled in me since, well, forever!
I was startled by the results of the transformation. I actually looked quite pretty!
Milly produced yet another distinctively female accroutrement, a pair of black high heeled shoes. I was uneasy at the prospect of having to wear them. Not only were they a icon of pure femininity, but they would be uncomfortable to wear. Milly got me to put my stockinged feet into them and helped me up.
The shoes raised me up so that I appeared even taller than usual. However, they made me wobble about and it took me a while to find my centre of gravity. Walking in them for even a short distance was challenging and I was forced to adopt short, mincing steps in place of my usual long stride. The shoes also rubbed my feet and toes. They were seriously uncomfortable to wear!
Then Milly handed me something which made me groan inwardly. A handbag! It was a Prada one that I had bought for Milly and which she was now loaning to me. It was yet another symbol of womanhood. The previous evening, I had had to transfer all of my money and credit cards to a purse. The purse, a compact mirror and some make up occupied the handbag.
I accepted the handbag with inward reluctance. I would have to cart this thing around with me everywhere.
Milly helped me into a ladies' brown macintosh. My transition from man to woman was complete!
Now I had to go out and face the world. My stomach was turning somersaults at the thought of everyone seeing the new me.
Milly gave me a gentle peck goodbye, then pushed me out of the door and quickly shut it behind me, as if to say "there's no way back lady!".
I stood there for a few minutes, wibble-wobbling in my new shoes. I could feel a draught up my skirt, the unaccustomed weight of my handbag perched on my right arm, and my earrings swaying gently. Momentarily paralysed with fear, from somewhere within me, a spark of courage galvinised me and I bravely stepped forward......
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