The first thing I discovered was a note signed by ‘Margaret’ and I smiled realising that this was the first time the shopkeeper had actually used her name. The note listed the contents of the bags and, as I read the tiny handwriting, I could not hide my disappointment at how little she had let me take from the shop. There was an exquisite blond wig, an incredibly tight corset and some underwear but no makeup and no outer clothes at all. Even the shoes, beautiful as they were, were rather flat compared to the pair I had been fitted a few days earlier. However, I sent the rest of the day wandering around the house in delicate underwear, stockings and suspenders and my pretty patent leather shoes, enjoying the freedom of being able to wear the long blond wig without fear of being caught. It was a fantastic day and, despite the limitations of my wardrobe, I knew that I wanted more. Later that evening, my prayers were answered as Sandy announced that she had to go away with the Managing Director for two weeks to accompany him on a conference. Despite the fact that I knew the lecherous old man had designs on my wife, I could barely contain my enthusiasm for her forthcoming trip. Three days later she was gone and, at last, I had the house to myself.
On the first day after she left, a package arrived for me in the post and I opened it eagerly. I was not expecting anything and I was surprised to discover that Margaret had sent me a small gift. Nestling amongst the crumpled tissue paper was another note and, to my amazement, a pair of wonderful silicone breasts. As I read the now familiar handwriting, I felt my eyes glaze over. Some indeterminate time later I found myself in town, credit card in hand, wandering in a daze from shop to shop. I hardly registered what I was buying but somehow, by the end of the day, I had acquired cosmetics, jewellery and a new pair of outrageously high-heeled shoes and some decidedly kinky thigh-length boots. My taste in clothes seemed to centre on the gloss PVC designs that Margaret had introduced me to in her shop but, unable to find a suitable ladies retailer and too embarrassed to visit Margaret again, I found a shop selling leather skirts and jackets. Somehow overcoming my unease about buying women’s clothing, I had soon acquired my first real outfit.
Once corseted and happy with my underwear, I placed the silicone breasts into the welcoming support of my bra and my figure took on the curvaceous shape that I now desired. Over this attractive female figure, my tight leather skirt, crisp white blouse and figure-hugging leather jacket looked fantastic and I spent the rest of the day in a daze. The day-to-day business of cooking and cleaning in my home took on a whole new meaning once I was dressed, every glimpse of my manicured nails and feminine figure filled me with pleasure. I felt completely relaxed, more at ease with my body than I had ever felt before.
This enjoyable routine continued for the next three days. I would wake early, shower and cleanse my skin before dressing in my increasingly familiar leather outfit. I slowly grew accustomed to seeing my feminine form in the mirror and it soon seemed perfectly normal to be wearing stiletto-heeled leather boots and a short leather skirt. My previous masculine existence seemed like a distant memory as I grew progressively more attached to my female persona. I had even taking to reading Sandy’s romantic novels to pass the time as I enjoyed the simple pleasures of wandering around my home dressed as a glamorous attractive woman. That afternoon though, everything changed.
It was 3 O’clock when the phone rang; I recall the time exactly for some reason but the voice on the line was not my wife’s as I had been expecting.
"How are you getting on Richard?" Margaret asked me, her voice crackling on the line. "I assume that you’re dressed."
"Yes I am." I stammered. "My wife has had to go away for a while…"
"Good." Margaret interrupted me. "I think its time for the next stage of your transformation to begin. Have you been brave enough to venture outside dressed yet?"
"Good god no." I exclaimed. "It’s hard enough overcoming my embarrassment at home never mind…"
"Sleep Richard." The voice commanded. "Just relax and listen to my voice."
The journey passed in a daze. I blushed as a group of men shouted across the road, commenting rudely on my appearance but, rather than being angered by the attention, I actually felt flattered. I barely noticed as my gait took on a cute wiggle after the encounter. Somehow, I must have managed to raise the pitch of my voice as I bought my ticket because the bus driver barely raised an eyebrow as I found myself a seat on his mercifully empty bus. Shaking with fear and, though I hate to admit it, excitement I somehow completed my journey relatively unscathed. By the time I arrived at Margaret’s salon, I was breathless after the thrill of my first public appearance as a woman. I felt so relieved to have actually ‘passed’ for the first time, I barely winced as the assistant pierced my ears. Five minutes later, I was wearing beautiful gold rings in my ears and, more surprisingly, a tiny diamond stud in the soft folds of my upturned nose.
After this more permanent feminisation of my features, Margaret took me to a quieter area of her salon and explained what the next stage of my transformation would involve. I listened attentively and, once I had heard the key post-hypnotic word, my resistance simply faded away. As Margaret continued, once more lulling me into a deeply suggestible state, I found myself impatient to continue with my profound feminisation.
"You have clearly become quite an enthusiastic crossdresser over the last few weeks." She said matter-of-factly. "And you clearly enjoy acting out your feminine role."
I nodded, trying desperately to keep my eyes open as Margaret’s voice soothed away my doubts.
"After today’s session however, you will graduate from simple crossdressing to the next phase of your training. You will soon be a dedicated transvestite Richard, living and dressing as far as possible just like a real woman. We will do everything we can to assist you in your transformation of course; supply you with suitably glamorous clothes and you have already had your ears and nose pierced. I’m sure the girls in the salon can come up with a makeover more in keeping with your burgeoning female sexuality and it shouldn’t be too difficult fitting you with some more permanent breast-forms."
My imagination was already filling with enticing images of what would be done to my body and I felt my glossed lips part in a wan smile as I anticipated the radical changes which would soon overtake me.
"I think its time we added a sexual element to your transformation as well." Margaret continued. "Your enjoyment has been quite innocent so far but you will have noticed already how men react to you. I don’t think there would be anything wrong in conditioning you to flirt a little and, given your wife’s obvious lack of interest in the bedroom department, it’s only a matter of time before you eventually succumb to some young man’s attentions."
Margaret paused, letting this new information sink in before she continued.
"We’ll undress you in a minute or so and see what we can do about hiding your more obvious masculine features. Your new breasts will be attached with surgical glue and to all intents and purposes they will be identical to the real thing. We’ll do some electrolysis on your legs and face and I don’t see any reason why we shouldn’t get you out of wigs and just give your own hair a touch of colour and a more suitable style. We’ll start you on hormones too and even though they will render you quite impotent, they should accelerate the feminisation of the rest of your body so I’m sure you won’t regret your decision to take them."
I took the pen that Margaret handed to me and signed the forms obediently without even reading the writing that swam in front of my eyes. One hour later with my flaccid penis tucked neatly into an elaborate cache-sex and my new cleavage jutting provocatively from a tight latex top, I was ushered back into the salon where the hairdresser was waiting to totally re-style my hair. The beautician had already worked her magic on my face and, with the tiny diamond glistening dangerously in my freshly pierced nose, I knew that I now looked almost unbelievably attractive. With dark arching brows and incredibly heavy eye makeup, my features smouldered in the mirror, promising a sexuality that I still did not truly understand. As I sat down, Margaret’s other intimate gift reminded me of new sensations that I was already being conditioned into accepting. The humiliation of being ‘plugged’ for the first time filled me with trepidation but there was something else too, something dark and thrilling, a forbidden pleasure that was already growing increasingly gratifying. I shuddered in anticipation as I lowered my buttocks carefully into the soft leather of the chair and waited for the hairdresser to begin.
TO BE CONTINUED
Don't forget to choose who makes the prettier girl (details here) and also choose which version of my eyes you prefer (details here)!
