In the four weeks since it was agreed I would move into Helen and Alice’s house, I’d achieved everything required of me, including putting my flat on the market, placing most of my possessions into storage, selling my car, getting used to the chastity device, buying four plain white bras, getting my ears pierced, and meeting Alice for the first time.
It had been a hectic period getting everything completed, and, at times, worrying and distressing. When the fateful Saturday arrived for me to move to my new home, I left the keys to my flat with the estate agent so that prospective buyers could look around, and then I travelled down on the train, carrying my two suitcases. There were butterflies in my stomach as I made the journey. I had already experienced Helen’s wrath, and I knew that she was going to be a tough mistress, on top of which there was the problem of Alice, who’d not taken to me at our one and only meeting. Nevertheless, despite my fears, I had burnt my bridges, and the only way was forward.
Of considerable concern to me was that I’d been unable to persuade Helen that I needed more time to come to terms with dressing entirely in women’s clothes. I’d broached the subject on the phone, pleading for a delay, but she had again dismissed my worries, saying her decision was irreversible.
I’d been told to travel down wearing male outer clothes over my bra and panties. This was the first time I’d been outside the house wearing a bra, so I was full of trepidation, not helped by it being a warm early-June day which precluded me from wearing a jersey or a coat.
I had to hope my shirt was thick and loose enough to conceal what was underneath. It also didn’t help that I’d had to exchange my deodorant and aftershave for more feminine products and, as I sat on the packed train, I was worried that my scent would attract attention. I was relieved to get off the train and walk the last mile to my new home.
On arrival, I rang the bell. Helen kept me waiting for a couple of minutes before opening the front door and beckoning me inside. We exchanged greetings and pecks on the cheeks, and I was invited into one of the several reception rooms in her large house. “In case you’re wondering, Alice is away and won’t be back until tomorrow evening, so we won’t be disturbed,” she advised.
“Thank you, I was curious as to whether Alice would be here when I arrived, Ma’am,” I responded.
“Well, now you know. And you have a bit of time to settle in before you see her again. I’ve spoken to her at length, and she is genuinely keen to have a second chance to get to know you. Alice is like me and doesn’t bear long-term grudges. Nevertheless, the ball will be in your court, so don’t screw things up again.”
“No, Ma’am.” I swallowed hard, as I remembered how disastrously wrong everything had gone the last time.
“So, Julie, do you have any further questions or concerns before you assume your new lifestyle? Have you been able to do everything to close the door on your old life?”
“No questions or concerns, thank you, Ma’am, at least none other than those already raised with you. And I believe I’ve done everything that you told me to do. I very nervously await my future.” I forced myself to smile.
“OK, so we’ll make a start. Strip down to your undies.” I quickly did as she asked, and I stood in front of Helen wearing just my bra and panties. Despite my nervous tension, I was aware that my penis was desperate to escape the confines of its cage and I couldn’t avoid wincing at the ensuing discomfort. Involuntarily, I took in a sharp intake of breath as pain from down under took hold. Helen smiled, knowingly, but said not a word.
She then picked up two breast inserts lying on a coffee table and placed them into my bra cups, before adjusting my straps to secure the inserts.
“That’s much better, Julie, these give you a nice shape. And, also, they are the same weight as real breasts, which will improve your experience of being a woman. The straps need to be kept tight to keep them in place, so I expect to see strap marks whenever you take your bra off.”
I had no proper idea of how much a real breast weighs, but, judging from the weight now hanging from my chest, they are heavy. I could appreciate why women with huge breasts can suffer back problems. Even these size Cs were going to take some getting used to.
“You will only take your bra off when showering or when sleeping. Understood?” she enquired. I nodded in reply.
Next, she pulled my knickers down and changed the padlock on the chastity device, while noticing how my organ was endeavouring to expand into a non-existent space. “This cage is a good fit. Obviously, I'm no expert, but I have a theory that small cages are better. Surely, cages that are roomy enough to allow partial erections are more brutal because they tease the wearer, leading them on, almost encouraging them to seek arousal. I think it must be better to nip a swelling in the bud by using a smaller cage. This one seems to strike the right balance, at least at this stage. We can always buy you a smaller one, sometime in the future." She looked at me before adding, in a matter-of-fact way, "How are you finding this cage?”
“I’m finding it tough, Ma’am, and I’m not sure how I will cope long-term."
“Hmm... it will take you time, I can understand that." She smiled, emphatically, though what true understanding she had of cages—and sizes of cages—was open to question. "You may find the discomfort from being aroused more of a problem than orgasm denial. So, try not to get aroused, eh, Julie?”
Well, that was easier said than done, but I decided it best not to discuss how I might achieve that objective. Instead, I added, “Also, it serves as an alarm clock, waking me up at five o'clock every morning, if not earlier.”
She laughed softly. “Yes, I know what you mean about the alarm clock. John used to complain about that as well but, over time, his willy realised that morning erections weren’t possible and it gave up, unless he had the misfortune of experiencing an erotic dream. Just give it time and you also should adapt, and be able to sleep later.” She made it sound simple, but, of course, the problem wasn’t hers, it was mine.
“As to coping in the long term, well, if you behave yourself and meet or exceed expectations, you can expect regular relief in some form or another. It's not in my nature to be cruel, Julie. On the other hand, if you misbehave or disappoint me then you will be locked up for longer periods. The good thing, from your point of view, is that the increasing frustration you experience will encourage good behaviour. You understand me?”
“Yes, Ma’am, I understand.” Indeed, I understood perfectly. I was already feeling frustrated, and this was just the start. I was sure the frustration would drive me to better serve Helen in the ways she expected.
“When did you last masturbate?” she asked, indifferently, as if she were asking when I last had a coffee.
I hesitated for a moment before answering, “Yesterday, Ma’am, I’m afraid.”
“Thank you for your honesty, but I will need to take that into account when deciding when next to give you relief.”
I was left standing in my bra and panties, feeling humiliated but painfully aroused within the tight constraints of my device, while she went through the rules I would need to follow while living in her house.
First, she explained my working hours, which were not as onerous as I had been anticipating. From Monday to Friday, inclusive, I would be working from 7 AM to noon, and then from 2 PM until 5 PM. On Saturdays, I only needed to work till noon, making it a forty-five-hour working week. The rest of the time, including Saturday afternoons and all-day Sundays, was free for me to do what I wanted, within reason, except that I was expected to help Helen get meals ready and then wash dishes afterwards.
I was then given several pages of A4 detailing the housekeeping tasks I had to do, and the standards to be met, but, in essence, I was going to do anything and everything that was associated with cleaning, laundry, shopping, and grass and hedge cutting. Underperformance of any kind, or any misbehaviour, would be punished, and very serious breaches of rules would result in my expulsion from the house.
It was also emphasised that any sexual advances towards Alice, including flirting or racy banter, or discussing my sexual relationship with Helen, would bring my housekeeping career to an abrupt halt and I would be thrown out with just the two suitcases I’d arrived with. Nonetheless, Helen stressed that I was not a prisoner and was free to leave at any time, although that would end my relationship with her, something that I didn’t yet want to contemplate.
Then she led me upstairs to what was going to be my bedroom. I had seen it before, while doing cleaning for her. It had been Alice’s room many years earlier, and it was tiny. She had used it until she was aged five because it was conveniently next to the master bedroom. Now Alice was in a much bigger bedroom, and her original room had been left as it was, still decorated predominantly in pink Disney wallpaper, and with a single bed that would have been too long for a five-year-old, but was far too short for me.

Even the bedding was intended for a child and wasn’t going to cover my longer body. There was minimal furniture and storage, so no wonder I’d only been allowed to bring two suitcases with me. What’s more, this was the only one of the four bedrooms in the house that did not have an ensuite bathroom, but there were facilities on the opposite side of the landing that I was to have exclusive use of.
Looking around, I was perturbed to see that hanging on the wall of the bedroom was a rattan cane. Helen saw me gazing at it. “My God,” I said, “you didn’t use that thing on Alice, I hope.”
“Of course not, don’t be ridiculous. I would never strike Alice with anything, let alone that cane. But it was sometimes applied to John’s backside. Save only for expulsion, the cane is the most severe punishment you will receive here. I hope not to use it on you, and I thought if it was hanging in plain sight it might serve as a deterrent.” Whether she was being truthful in saying she had no wish to cane me was a matter of conjecture, but I nodded in complete agreement.
Then came the moment I’d been dreading. Helen opened the small wardrobe, and I was introduced to my new uniform, of which there were several sets. It was not a maid’s outfit, which might disappoint some readers of transgender fiction, but, to me, it looked terrifying.
On my lower half, I would be wearing pocketless, beige trousers, tailored in a distinctly feminine style, along with pink ankle socks and pink trainers. Above the waist, I was going to have to put on a white T-shirt embossed, in pink, with the words “Julie, Housekeeping”, as if I was on the payroll of a hotel.
"The slogan was Alice's idea," Helen remarked. "I was fortunate to find a company that could knock them up in just a couple of days." She seemed pleased with purchases, maybe thinking that if Alice was contributing ideas there was a greater chance of me being accepted by her. I had my doubts, but chose to keep quiet.
"And on cooler days, you've got these." She went on to explain that I could either wear a plain, white cotton camisole with spaghetti straps beneath my T-shirt and over my bra, or wear a black fleece over the T-shirt—the fleece also bore the pink “Julie, Housekeeping” slogan. When necessary to protect the uniform, there were also pink aprons carrying the same motif, this time in white.
My uniform had to be worn at all times when I was on duty, including during trips to the supermarket or other stores. To complement it was a pink handbag with a shoulder strap, in which I was to carry my phone, bank cards, and so on.
“I designed the uniform to be androgynous so that you can wear it in public without being arrested! I think Alice is buying into this style as well, although she may still hanker over you wearing a dress at some time in the future,” Helen remarked, giggling. I could see it wasn’t erotic, but it was definitely very feminine and would be nerve-wracking to wear in public. I felt myself trembling at the prospect and I was close to tears.
“When you're off duty, you can wear what you like, but always with at least bra and panties.” And then she added, menacingly, “Unless I decide otherwise, which I might do! Now get dressed while I watch, as I want to make sure everything fits.”
As I was already in my underwear, it didn’t take long to put on the remaining items. The trousers were a skinny fit and ended four inches above my ankles, leaving an expanse of bare flesh above my pink ankle socks. And the thin white T-shirt was a tight fit, doing nothing to obscure my bra.
I caught a glimpse of myself in a mirror on the wall, causing me to make a grab for a fleece to put over the top, but Helen stopped me. “Don’t be silly, it’s too warm for a fleece.”
I was horrified by my appearance and unable to disguise my horror. “What’s the problem?” she asked, as if she didn’t know, because I’d expressed my concerns so many times before.
To avoid another harsh spanking, I knew I needed to approach this matter very delicately. “I hope you don’t mind me mentioning this again, Ma’am, but I’m really so sorry that I can’t wear this uniform in public. It will be too humiliating—I’m totally mortified at the thought.”
She took my hands in hers and said softly, “Take some deep breaths and calm down, Julie. You’ve told me many, many times that the thought of being made to dress as a woman in public is a big turn-on for you. Isn’t that right?” I nodded. What she said was true as a fantasy, but the reality was very different and very sobering. “And can you honestly say that you are not becoming aroused, right now, looking in the mirror and knowing that you have no choice other than to wear it? I can see it in your face.”
I couldn’t deny what she said, because my penis was pushing against the bars of my cage, and I felt my panties becoming damp from pre-cum.
“What’s more, with a bit of effort, you could convincingly pass as a woman! You’re not too tall, you are slim, your body shape is good, pert and not too muscular, your facial features are quite feminine, with lovely bone structure, and your hair is already on the long side. And, importantly, you are hairless below the neck. All that is needed is a little make-up—not too much, mind—a nice necklace, and some skin care with suitable moisturisers. Then, just soften your voice a spot and move a little more gracefully—I’m sure you can do this, Julie.”
She gazed at me, willing me to believe she was telling the truth, before continuing. “In those many conversations we had over the past few weeks and months, I said how much I wanted to push you to your limits, and beyond. This is one of those occasions, and I have every confidence that you will break through limit after limit and end up thanking me for pushing you. You’re going to have fun—we’re going to have fun! OK?”
I nodded, and then smiled. It was a genuine smile because Helen was right in what she was saying. “Thank you for your confidence in me, Ma’am. I’ll do my level best not to let you down.”
“I’m pleased you see it like that,” she replied.
“I have another question, if I may. When you're at work, am I looking after Alice if she’s at home?” I enquired.
Helen giggled. “She’s eighteen, for goodness’ sake! But, yes, you are there to make sure she doesn’t do anything I don’t approve of, such as entertaining a boy in her room.” She laughed again, but I experienced a wave of fear—the frightening thought of Alice’s friends, girls or boys, turning up at the house had never occurred to me, until that moment.
“Ma’am, please! I don’t think it’s a good idea for Alice’s friends to see me dressed like this.”
“Julie! Alice is not stupid, so you’ve got to trust her instincts to do the right thing. After all, she’s hardly likely to do anything that causes herself embarrassment in front of her friends. You overthink things. Just relax!”
This was simple to say, but hard to put into practice. Helen continued, “Anyhow, as I was saying, just make sure Alice doesn’t do something that may lead to regrets, otherwise, she’s in charge and you will do what she tells you. Is that clear?”
I was getting scared. “But she’s only eighteen years old.”
“Yes, she’s eighteen! She’s not a child! She’s just the right age to be given authority over others. This will give her experience that will pay dividends post-university when she’s in a managerial role. It’s an important step in her mental development. So, like I say, if she tells you to do something, you do it. OK?”
“What about if her demands are unreasonable?”
“Oh, for crying out loud, Julie! You’re more than twice her age. If she’s being unreasonable, surely, in thirty-seven years, you’ve gained the persuasive skills to talk her out of what she wants you to do. Use some common sense, for goodness’ sake. You seem to find a problem in everything you’re told. Start having a more positive attitude.”
“Sorry, Ma’am,” I conceded, yet fearing what might come.
“And, if you try to involve me in any petty disputes, it’s Alice’s side I’ll be taking. You have to fight your own battles. But I will be checking with Alice that you’re doing your best to be cooperative and not obstructive.” I gulped, but nodded to show my understanding.
She waited for all of this to sink in before continuing. “On a brighter note, I will be paying you an allowance of one hundred pounds per week, but at least a quarter of that must be spent on feminine items, such as clothes, cosmetics, creams, etc. Everything must be receipted, so that I can monitor you, and paid for using the personal credit card that I’ll give you. You’ll also be given another credit card for household expenditure, such as groceries and petrol. And you are no longer allowed to spend any of your own money, so I’m confiscating your old bank cards.”
“Yes, Ma’am, I understand. Thank you for the allowance.”
“Oh, one more thing! I need your phone. After your behaviour at the zoo, I intend to install child protection measures to control what you can do and when you can do it. It will also allow me to check up on you.” I handed it over to her, unlocked, recognising that yet another bridge to my past life was on fire.