Alice and I continued to run 5k a couple of times a week. I was always dressed in her old school uniform, while she was attired in something more like what other runners were wearing. It was mortifying that my short gym skirt was forever flipping up, revealing my gym knickers. I did try to persuade Alice that I would be better off wearing shorts, like her, but she would have none of it. “Surely, it must be embarrassing for you, Miss,” I had argued, “to be running with someone dressed in this short skirt. Why don't I buy myself some shorts?”
“No, Julie, it's not at all embarrassing for me,” she giggled, while shaking her head. “Are you saying you don't like wearing that gym skirt?”
I sensed she was laying a trap, but I blundered on. “Er... yes, Miss, that's what I'm saying.”
“Then I've got an idea! We drop the skirt, and you run in your knickers. People will think they're shorts. Problem solved and money saved!”
She beamed at me with delight. Yet again, she had verbally outmanoeuvred me. “Oh, no, Miss, it's best I keep wearing the skirt. Thank you.”
“Thought you might say that!” she smiled, knowingly. “But as a forfeit for trying to outsmart me, now when we run, I want you to put your hair into a ponytail and secure it with a clip.”
“No, Miss, I don't need a ponytail or a clip.”
“Yes, you do! If you're going to defy me, I will have to punish you. I will not stand for insubordination. Understood?”
“Yes, Miss, sorry, Miss.”
So, the next time we ran, my hair was secured in a ponytail, held together by a vivid pink clip that she gave me. If her intention was that it would draw even more attention to me, then her objective was achieved. I felt many eyes on me as I ran along.
On one occasion, there was even a wolf whistle. I assumed it was directed at Alice, but she corrected me. “No, that was for you, Julie. It's the way your ponytail is swinging seductively from side to side as you run. It makes you look far more feminine. So-much-so, you've turned that bloke on!” I felt myself redden, and I was sure she was fibbing, but how could I be sure? Had I really become so feminised that I was attracting male attention?
oooOOooo
When I was not working, I was free to dress as I pleased, as long as I wore my female undies. Therefore, to reduce my embarrassment, in my spare time I took to wearing male shirts and trousers. Whilst this was allowed, I detected growing resentment from Helen and Alice about this style of dressing. I was frequently nagged that I wasn't making an effort to fit in. Both wished I would dress full time as a woman.
Alice tauntingly suggested to her mum that I needed a prettier selection of garments to entice me to dress en femme fulltime. This encouraged Helen to introduce a new rule, that each week I was to use part of my allowance to purchase, from the supermarket, two outer items of female clothing.
What’s more, Helen then agreed to Alice's malicious suggestion that there should be a “one-in, one-out” policy, which meant that if I purchased a skirt, I was required to get rid of a pair of my male trousers. Likewise, buying a blouse would mean having to throw out a male shirt. A dress counted as two items, leading to both trousers and a shirt being discarded. My entire male wardrobe, small as it was, was soon replaced entirely by female attire, but the rule about spending part of my allowance on female clothing persisted, being extended to underwear as well as outerwear.
If she was around, Alice accompanied me to the supermarket and suggested purchases I should make. "Suggested" was her way of insisting, and invariably she got her way, so my effeminate wardrobe grew in size. Strangely, I found this inevitable progression to becoming more female to be very arousing, whilst simultaneously terrifying. When Alice was giving me suggestions on what to buy, my penis was always pushing against the bars of its prison, not that she was aware of my dilemma, thinking instead that I was being humiliated but not aroused.
Rapidly, I accumulated a collection of very girly clothing—miniskirts in bright colours, diaphanous shirts, tight fitting vest tops, and summery dresses with spaghetti shoulder straps. However, one remaining consolation, at this stage, was that apart from our 5k runs, I only left the house to visit the supermarket, and that was in the trousers that were part of my housekeeper outfit.
But this was soon to change. On one shopping trip, Alice spotted a plain blue skirt, with a hem that finished just above my knee, and she recommended I should buy it. As it was so different to her other recommendations, being more business-like than girly, I was suspicious as to what she had in mind, but all was revealed that evening when Alice casually remarked to Helen, “Mum, I don't think Julie should be wearing trousers as part of her housekeeper uniform—not in this warm weather. It's cruel—really very cruel.” She looked across as me slyly, before delivering the killer blow, “This blue skirt is smart enough to wear instead. What do you think, Mum?”
Alice held up the dark blue skirt against my waist and Helen immediately went along with her daughter's idea. My uniform trousers were swapped for a skirt and, of course, I had to wear this when visiting the supermarket, as well as around the house. What I thought was a personal limit had been breached and, before I knew it, I was wearing skirts all the time, in a multitude of different styles, and I was sent down to the charity shop to dispose of my uniform trousers. More and more occasions cropped up when I was sent out alone on some errand—going to the corner shop for a newspaper, to the drycleaners for Helen's dress, or to the petrol station to fill up the car.
Moreover, as I became more feminine in appearance, I'm sure Alice took to wearing jeans and trousers more often, no doubt to emphasise that she could, but I couldn't.
Alice also took malevolent delight in showing me how to wear a skirt, instructing me on how to smooth the back down before sitting. Sometimes, a whole lunch hour might be spent with me repeatedly sitting down, then standing up, walking around, before sitting again. Just as importantly, she stressed to me the importance of keeping my legs together when sitting. “You don't want people seeing your panties, Julie,” she teased, and my mind went back to the occasion when she had lured me into looking up her skirt to see a pink triangle.
I was being increasingly feminised by Alice, with Helen almost an amused bystander, seemingly unaware that both I and Alice were being turned on by what she was doing to me.
Alice was always in the driving seat, and she had this ability of embarrassing me and arousing me on at the same time. She was continually pushing me past my limits, yet I found what she was doing was stimulating me in every sense of the word. With her continued help and encouragement, I became more confident about applying make-up and passing as a woman. She also gave me advice on styling my hair and she even accompanied me to a salon, where, sitting in a summery skirt and revealing blouse selected by Alice, I had my hair cut and styled in a feminine fashion. The next day was a visit was to a nail bar, where I received a manicure and pedicure and left with brightly painted nails.