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.
Despite these stressful ordeals, I could see that the changes were successful in helping me pass as a woman. Nevertheless, they were humiliating events which I couldn’t have gone through without Alice being at my side.
oooOOooo
As I was pushed down this path towards increasing emasculation, there was a growing problem, one I could not discuss with Alice who was still ignorant about me being locked in a chastity device. Despite it now being many weeks since I had become the housekeeper, I’d not been unlocked for any relief for my sexual frustration, and I was becoming desperate. Helen was right when she had said that the increasing urge for release would ensure my compliance in anything I was asked to do, and I began working extra hours to get everything done to a level that defied criticism.
I had had no further sexual activity with Alice. She had ruled that out, and perhaps for the best, as another session pleasuring her with my mouth might have driven me crazy. Helen, though, did expect to be serviced by me in this way, and a few times a week there would be steamy sessions in which I gave Helen multiple climaxes, further increasing my frustration. During these sessions, I was naked, blindfolded and handcuffed, and my cage was never unlocked, causing me agonising pain. I could taste her arousal and ride with her as she climaxed, but orgasmic satisfaction was always denied to me. Sometimes, Helen sensed my disappointment, pre-empting me from vocalising any concerns by saying I needed to be patient. I was being patient, but I had never experienced such prolonged abstention in all my life. I recalled the time, not that long ago, when I was free to enjoy erections, and when masturbation was an almost daily occurrence.
With my frustration growing by the day, I had a brain wave and came up with a compromise that I thought Helen might accept. I waited until my weekly appraisal, knowing that at the end she would ask me if there was anything I wished to say or ask, off the record. “You may speak freely, Julie,” she would explain. “This is your chance to give me honest feedback on how things are working out.”
Sure enough, at the conclusion of my next review, she invited me to say what was on my mind. I hesitated before replying. “Thank you, Ma’am,” I began. “Erm…, I understand why it’s not in my interests to be allowed relief. As you’ve explained, it does make me more obedient. However…, er…, I was wondering whether you might allow me to have erections sometimes, even if I'm not allowed to cum?”
She stared at me, wide-eyed. Shaking her head, she asked, “Do you really think that would be a good idea, Julie?” Fortunately, the question was rhetorical, and she quickly continued, “Can’t you see that would be like letting an alcoholic sniff a bottle of vodka?”
This time, she waited for me to reply. “I don’t know, Ma’am,” was all I could say.
“Oh, for crying out loud, Julie, surely you can see that if I were to unlock you, so you could become fully erect, that would only add to your problems. You’d become even more desperate for release. It would be pure torture!”
“But, Ma’am, it’s torture now, when my penis tries to grow into its cage, only to find there’s no room for expansion.”
She snorted, which I thought was a little unkind. “For goodness' sake, if you’re going to think about sex all the time, of course it will swell up. Try to think of other things.”
“But when I’m pleasuring you, Ma’am, that’s impossible.” I didn't dare mention that my lunchtimes with her daughter were also a frequent source of arousal.
“We only do it three or four times a week, so learn to live with it,” she declared. She broke off to think, and I had a sense of foreboding as to what was to come. Sure enough, she turned the tables on me. “If you want it, I could get you a smaller cage. One that has absolutely no expansion room. That way, even the slightest arousal might warn your penis that it’s on a hiding to nothing. It might nip the problem in the bud. What do you think?” She smiled meanly, knowing what my response would be.
Once more, I had been defeated by one of the women who controlled my life. The thought of being held in a cage so small that I would be in permanent discomfort, and most likely persistent pain, didn’t bear thinking about. “Thank you, Ma’am, but I'm sure I can control my frustration without being put into a smaller cage,” I responded, forcing a smile.
She gave me a satisfied smirk, before saying, “I thought you might come to your senses.” Then she paused to think again, rubbing her chin. “Tell you what, Julie, let me give you some relief now. Eh?”
I couldn't believe what I was hearing and, sure enough, it was too good to be true. She continued, “As you’ve been a good girl, I’ll give you a prostate milking, right now.”
I’d read about such a thing, but never experienced it. As always required for my appraisals, I was dressed only in my underwear, so Helen told me to slip off my panties and then kneel on all fours. She disappeared for a few minutes, before returning with a saucer, some lubricant and a strange, curved device, which I was soon to learn was a prostate massager.
The saucer was placed beneath my locked penis and lubricant was applied to the device, which was then gently pushed through my anal sphincter into my rectum. She then worked the instrument up and down, using its end to stimulate my prostate.
It took just a couple of minutes of gentle thrusting back and forth for semen to start dribbling into the saucer, and a further ten minutes before the flow stopped. It was a strange session, which was pleasant but nowhere near as rewarding as an orgasm. Most disappointingly, there was no climax, just a slow ooze. At the conclusion, I was empty, but I’d received no fulfilment, and I was just as frustrated as I had been at the start.
“That should stop you having wet dreams,” she joked, or at least I was hoping she was joking. I’d not had a wet dream since I was a teenager but, being denied release, it might soon have occurred if she had not drained me.
I was still on all fours, resting on my knees and elbows. “There’s a price to pay for what I’ve done for you, Julie,” she laughed, while moving the saucer so that it was in front of me.
Having a good knowledge of femdom literature I knew what was expected. I leant forward and caught a pungent whiff from the freshly expressed fluid, still warm from my body heat. It looked revolting—whilst milky in colour, this stringy, gelatinous liquid could never be mistaken for milk. I felt nauseous, yet I bent further forward and began lapping up the slime. This was a first for me, and the viscous, salty semen made me gag a few times, but I managed to clean the saucer to Helen’s satisfaction. What I had done seemed so depraved, and I felt debased, yet contrarily the humiliation caused my penis to start swelling, bringing me full circle in terms of frustration. It had all been for nothing!
