Man to Maid

 1 - Girls Night Out

Julie touched up her lipstick, studying her reflection in the bathroom mirror. Her dark hair slipped loose again, and she tucked a stray lock back in place. Friday night was a welcome break. Across the country, perhaps across the world, office routine was predictable. She looked forward to a few drinks with coworkers to mark the end of another week before heading home. It was a chance to let loose, catch up on gossip, and laugh off everything from office politics to life’s smaller dramas. She looked forward to these nights, especially at the end of a week that included dodging her parents’ telephone calls.

Nearly a year into living with Peter, her parents still hadn’t warmed up to the idea. Every call seemed to circle back to the same topics - why there was no talk of marriage yet, or grandchildren, which only added to the strain. Her mum rarely missed a chance to slip in, “So, when are you going to settle down properly with someone?”

Julie’s response had become routine: Peter and I are only 23. It’s too young for marriage or kids.
She mostly believed it.

Peter had kissed her goodbye, his lips lingering longer than usual. "Have fun tonight.” 

She tried to shake the unease, but her mind drifted back to the night before. They’d been lying in bed when she asked, “Is something wrong?”

Peter hesitated, then he told her. In that split second, if superpowers existed, Julie would have chosen the ability to unhear as her superpower. 

The weight of his words had hung heavy on her chest. She tossed and turned until dawn announced its arrival through the curtains. A few months ago, she would’ve run the other way. But now? She wasn’t sure. Things were different.

***

A voice through the door ended her daydream abruptly. “We’re leaving, Julie. You ready?” a coworker called out.

“Coming” Julie took one last look in the mirror, she looked good but her smile didn’t quite reach her eyes. 

The bar was alive with the usual Friday night crowd. They found a table to settle with their drinks, soon the table buzzed with laughter and overlapping conversations. Stories about annoying clients and office drama floated around the table providing a distraction from real-life.

Cathy, Julie’s closest friend, slid into the seat next to her. Cathy always managed to read her mood. She nudged Julie, passing her a drink. “You alright?”

Julie smiled,“yeah, just... stuff on my mind.” Cathy knew her friend well enough to sense a heart-to-heart was needed and switched to soft drinks.

By ten, people were calling taxis, the table thinning out, “you want to talk about it?” Cathy asked, leaning in, her voice softer now.

Julie hesitated, “no, perhaps, not here.”

2 - The Uber Ride

Cathy steadied Julie as they made their way to the waiting Uber, they slid into the backseat of the car, the warm air inside feeling almost too cozy after the cool night breeze. 

"Usual route?” the driver asked, barely glancing at them. He’d driven them before and tried his pickup lines before. Choosing AirPods over conversation he pulled into traffic.

Julie leaned her head back against the seat, the alcohol buzzing pleasantly through her system. Cathy sat next to her, her face illuminated by the dim lights of passing street lamps.

"I had a good time tonight," Cathy said softly, breaking the comfortable silence.

"Yeah, it was fun." Julie paused, then added, "You and Jim should come over for dinner sometime soon."

Cathy smiled, turning her head toward Julie. "Or we could all go out for a meal. Payday soon, we could make a night of it."

"That sounds great," Julie replied, the alcohol continued loosening her inhibitions, pushing her to speak.

Silence settled between them, Julie fidgeted with her hands, "Cathy, has Jim ever wanted to... you know, dress up?"

Cathy blinked, turning her head slowly. "Dress up?"

Julie’s cheeks flushed, and she regretted asking the question immediately. But now that it was out there she plowed on "I mean, has he ever mentioned wearing your clothes?"

There was a pause before Cathy let out a soft chuckle. "Oh, Julie. I think every guy has those fantasies.” Cathy's voice turned playful. “Let me guess, he wants to wear your panties in bed, right?"

Julie’s heart skipped a beat. She hadn’t expected Cathy to be so blunt, but at the same time, her openness made it easier to talk. She bit her lip and leaned in slightly, lowering her voice. "Don’t tell anyone, Peter… wants to wear a dress. Of course I said no. I mean why would he want to do something like that Cathy? He knows I’m not comfortable with kinky stuff."

Cathy raised an eyebrow, intrigued but unfazed. “Is this just a dress indoors or going out like a woman?"

Julie hesitated, then sighed. "He wants to wear a dress indoors sometimes, says it might be calming! Do you think he’s gay Cathy?”

“I don’t think gay men do that, prance around in dresses, it is all leather and muscles for those guys Julie. Could be a passing fantasy…he tries it, doesn’t like it, moves on” Cathy remained silent for a beat then, to break the silence, laughed softly. "Well, this ride is more entertaining than I expected."

“Be serious Cathy! I just…” Julie trailed off, feeling suddenly embarrassed. "I don’t know how to handle it. I mean, what if I come home one day, and he's just sitting there, reading, wearing a dress? I cannot cope with that."

“Reading? Get real Julie! Wanking more like!” Cathy leaned back in her seat, crossing her arms with a grin. 

“Cathy!!! Reading to relax he said.”

“Lighten up Julie, just tell him you don’t want to see it and let him wear whatever he wants. I mean, what harm is there?”

Julie let out a nervous laugh, then shook her head.

“This is me” Cathy leaned in, planting a quick kiss on her cheek as the Uber rolled to a stop. 

"Good night!" Julie called after her, but her thoughts were already swirling, heavy with everything that had been said.

Cathy shut the door behind her, kicked off her heels and looked into the lounge room, beer cans and snack wrappers that had joined the mess that existed before she left for work that morning. “Stopping over tonight Jim?” 

Of course he was. Cathy looked forward to Friday night sex but wished it was a little more… satisfying.

Sounds of Jims’ movie filtered through to the kitchen. Cathy filled the kettle and set it to boil, ignoring the sink overflowing with dishes she scrolled, googled, bookmarked - Julies revelation had setoff thoughts that frightened Cathy a little. The kettle whistled, Cathy made tea, put the box from his beers in the recycling and joined Jim on the couch, handing him a mug.

“Thanks,” he muttered, eyes still glued to the screen.

The movie ended, credits rolled. Cathy glanced over at Jim, who was already starting to doze off. She nudged him lightly. "Hey, you’ll never guess what Julie told me tonight, you know how prudish she is… Jim!”

“What?” He sounded disinterested

“She is all worked up because Peter wants to wear a dress occasionally. Can you imagine?" Cathy smirked, setting down her mug.

Jim sat up straighter, as alert as a small dog hearing a leaf rustle. "Wait, what?"

Cathy retold the Uber-story  “… Saying no is unreasonable, right, I mean I would let you wear a dress. Does Jimmie want me to let him wear a dress?”

Jim theatrically spluttered, nearly spilling what was left of his tea. "Absolutely fucking not," he blurted out, wide-eyed.

“Julie said the exact-same thing.” Cathy smirked, setting her cup down. “I might come back to this. Meanwhile, Jim, take some time to think it over” she said, her voice laced with amusement. She leaned back into the couch, chuckling softly at his discomfort “even the manliest of men have a feminine side.”

Julie’s revelation had lit a fire in Cathy, and there was no putting it out! She spent the night researching, reading and scrolling on her iPhone. By the time Jim woke she had learnt the fundamentals of crossdressing, feminisation, transgenderism, female led relationships, the importance of humiliation, and much more. 

Julie awoke the next day, her head pounding. She blinked at Peter, feeling disoriented. “Was I very drunk last night?” she asked, her voice groggy “I can’t remember coming home.”

Peter chuckled. “You don’t even remember how you got home? You shared an Uber with Cathy. She called to make sure you were home safe…and to remind you about the meal at the end of the month.” Julie looked confused. “Seems like you don’t remember much.”

2 - Jim

Jim headed off to soccer after breakfast, Cathy to the mall. First store she bought what she thought of as a slut-dress - the shiny, sparkly, stretchy, material would work perfectly for what she had in mind, second store she bought what Jim called ‘fuck yea’ undies and sent him a selfie right from the changing room ‘think of me entertaining myself while you are out drinking with mates tonight’ her message read.

He texted right back - would arrive with food around seven. 

Scheming Cathy smiled at mirror Cathy - of course he would. 

She changed from mall-smart clothes into a casual look; makeup off, joggers, faded tee, slippers, hair in a messy bun and was slouched on the sofa when Jim arrived with the food. 

“Are you wearing it?”

“Not yet” Cathy smiled, said she had ‘sexy plans’ that included a shower together. 

Jim ate and drank in moderation. He did not want to risk a repeat of the limp-dick episode. And he did not want Cathy to remind him, again, not to overindulge the wine.

She applied makeup at late for work speed while Jim attend to his five o’clock shadow. He emerged from the bathroom with a towel around his waist, Cathy turned, let her bathrobe part to reveal the new bra, brief, suspender belt set and began to roll a stocking up her leg, “I bought something sexy for you”

Jim picked up the bag from the bed, took out a pair of panties, he held them up, smiled, said “I can’t wait to see you in these” his towel revealed just how much he was looking forward to it.

“Not my size silly” Cathy stood close to Jim letting his erection press against her stomach “they are your size, will you put your new panties on for me?”

“What? No way, I’m not some sort of gay, lady-boy, faggot Cathleen” 

The moment he full-named her Cathy knew they were several exchanges away from a full blown argument. Under different circumstances she would have backed down, said she was only teasing, but she really wanted this. “Oh, come on. I wear your boxers all the time and it hasn’t turned me into a gay-girl, and you never complain, but I guess I am more secure than you.”

“Secure, what is that supposed to mean?”

“It is okay for me to dress in mens underwear, it makes me feel closer to you - not gay.”

Jim laughed softly “It’s different for women.”

“But you think I am gay when I wear your boxer shorts?”

“Like I said, it is different for women”

Cathy went on the attack “do you fantasise I am a cockless man?” She noticed his cock no longer tented the towel “is that what this is about? If it is, I am okay with that”

“No, noting like that, look… I’m sorry Cathy, I’ll put the panties on if it’s that big of a deal.” Jim felt like an idiot standing there in the lacy panties, Cathy distracted him, said it was still early for bed, suggested they put some clothes on and watch porn in the lounge room. 

“I will wear anything you want.” She offered. Jim went to her closet, picked out the little black dress, so short that Cathy had never dared wear it outside the house, he asked her to take her panties off. She slipped her panties off and shimmied the dress over her head, “now I get to choose what you wear.” Cathy smiled and took the slut-dress from her closet. Jim couldn’t take his eyes off the shiny, sparkly, stretchy, dress. Cathy could barely keep her voice even as she said “let me put you into this.”

“No Cathleen” Jim crossed his arms.

Cathy held out the dress “you can hold it, holding a dress won’t turn you gay.” He gingerly took the dress from her as if touching the dress might just do that very thing. She realised this was not going her way when she caressed his flaccid cock through his panties and it stayed that way - in online stories the boyfriend was always hard, ready to cum instantly. Cathy dropped to her knees and even her mouth failed to remedy the issue. 

“Look…I’m just not into this Cathy.”

“Can we at least try it?” She pleaded, “once, for me?”

 Jim nodded and let her put the dress over his head. They snuggled on the sofa, Cathy was in heaven, Jim not so much. The screen played Jim’s favourite porn, normally he would be all hands on and needy within minutes, yet despite her best efforts he stayed soft and as disinterested in the porn as if it were one of her romcoms. 

Jim stood “Sorry… I am not into this Cathy.”

“Now I feel fucking ridiculous for making you do this, just take it off.” 

Jim sat back on the sofa naked “now where were we?” 

She breathed in sharply, “I’m sorry Jim” She swung a leg over his lap and rested her head on his shoulder. 

***

Cathy slid into the booth across from WhatsApp friend Angela, her heart racing slightly, the subject of their first in real life chat already making Cathy nervous. It had been Angela’s support had given Cathy the confidence to try dressing Jim. She gave a little smile as Angela sipped her coffee and leaned in.

“So, how did it go?” Angela asked.

Cathy sighed, her fingers tracing the rim of her coffee cup. “Not well, more a complete disaster actually. Jim wasn’t into it. At all. I tried the panties first, like we talked about, but he was turned off by them and the dress only made it worse.” She sipped her coffee “the evening was a disaster, even oral could not restore his erection.”

Angela raised an eyebrow, her surprise genuine. “Really? Sounds like he might be a lost cause Cathy.” She shook her head, taking another sip of her drink. “Honestly, it’s always easier when you start with a boyfriend who’s already intrigued by it, you know? Or better yet, finds it erotic.”

“So how do you find guys who are into this stuff Angela?” Cathy asked. “Do you think Jim might eventually come around, or… am I just wasting my time?”

Angela gave a thoughtful hum. “Well, in my experience, it’s best not to force it. If he’s really not into it, pushing too hard might backfire. But, to answer your question, there are guys out there who love it - who find it exciting and freeing. You just need to know where to look.”

Cathy leaned in, her curiosity piqued. “And where’s that?”

“There are clubs—places that cater to the trans and crossdressing communities,” Angela explained, her voice lowering conspiratorially. “You’d be surprised how many men, straight men, feel comfortable exploring that side of themselves. It’s all about being in a safe, welcoming space. You could take Jim along, let him see what it’s like. Maybe he just needs more exposure to the idea - maybe he is more bull material.”

Cathy hesitated, weighing Angelas’ suggestion. She and Jim were still new enough not to have had the exclusive talk yet and she had no idea how he’d react to something like that. Maybe if Jim saw other men exploring their feminine side, it might help him loosen up, break down some of his preconceived notions.

“I don’t know…” Cathy said slowly, she considered his suitability for the position of bull briefly before realising he lacked two qualities - size and stamina. Dismissing the idea she said   “I don’t think Jim would be into going to a club like that. But it’s an interesting thought.”

***

Cathy and Jim stepped into the dimly lit doorway of the club, the atmosphere was that of a club for socialising, tables where men and women talked, a dance floor where couples slow danced to soft music and the usual loners occupied bar stools like pigeons watching office workers eat their sandwiches in a park. 

The air was thicker with perfume than a whores bedroom, chatter, and the faint sound of laughter, but what really caught Jim’s attention - and froze him in place was the sight of men, here and there, wearing dresses, skirts, heels, wigs and such like. Some wore extravagant gowns, others more casual feminine outfits, but beneath the disguises, they were undeniably men in women's clothing. A few waitresses moved gracefully among the tables wearing delicate maids’ costumes and balancing trays of drinks with practiced ease.

Jim’s eyes widened in horror. “What the hell is this place?” he muttered, his voice barely above a whisper, Cathy caught the edge in his tone.

She had known he might react badly, but she hadn’t expected him to be this taken aback. “I…I thought it might be fun… or at least interesting” she said quietly, her hand reaching for his arm. 

Jim snapped back, anger flashing in his eyes, “Interesting? Cathy, you brought me to some freak show!” His voice rose four or five decibels - enough for a few nearby patrons to glance in their direction.

Cathy flushed with embarrassment but held her ground. “It’s just a club. I thought we could see it together, you know? Maybe it would help you understand”

“Understand what?” Jim’s hand gestured wildly toward a waitress who was passing by in a short, frilly, maid uniform. She seemed unfazed at working in a club awash with perverts. Ignoring Cathy she openly smiled and winked at Jim as she passed by.

“It’s just people having a bit of fun,” she tried, but Jim wasn’t having any of it. His hands balled into fists at his sides, and his jaw tightened.

“I can’t believe you thought I’d be okay in a place like this,” he spat. “This isn’t me, Cathy. This… all of it - it’s disgusting.” His words cut through the background hum like a knife.

Before she could respond, Jim turned on his heel and stormed out, the door slamming shut behind him. Cathy stood there, rooted to the spot, torn between running after him and staying put. Her heart pounded in her chest, a mix of anger, disappointment, and something else she couldn’t quite name for a brief moment - before realising the nameless feeling was arousal.

The server who Jim had gestured at approached, heels clicking softly on the floor. Asked “Can I get you a drink, ma’am?” as if nothing out of the ordinary had just occurred.

Cathy opened her mouth to decline but stopped as she realised what stood before her. 

Her eyes traveled over the maid uniform, the pristine white half apron, the black stockings, the small, delicate ruffles that adorned the sleeves of the uniform. She felt an unexpected tug of fascination. The outfit was so meticulously put together, so perfectly feminine - and worn with such quiet confidence by someone who, not long ago, might have been wearing a suit and tie.

“Yes, thank you” she said, her voice steadier than she expected. “A glass of wine, please.”

Man-maid nodded and click, clickety, clicked away, Cathy sat  on one of the plush, velvet-lined chairs at a small, empty, table for two that gave a panoramic view of the dance floor. The club was the kind of place where someone like Jim could have seen a different side of things if he hadn’t bolted so quickly. 

Maybe this was exactly why Angela had suggested the club.

Maybe it was about more than clothes. 

Maybe it was about freedom.

Cathy’s eyes examined the occupants in a victim at an identity parade way. Some were shy, tentatively adjusting their outfits or sharing nervous glances with their partners. Others were bold, walking with an exaggerated sway, clearly enjoying the performance of femininity. She noticed how the servers moved with practiced grace, as if they took pride in the roles they played here.

When the waiter returned with her drink, Cathy smiled at him, feeling a strange sense of calm wash over her, the more she sat here, the more she felt… intrigued.

Cathy sipped her wine slowly, her mind spinning with the possibilities. Maybe Angela had been right all along. Maybe it wasn’t about changing someone like Jim. Maybe it was about finding someone who already wanted this, someone like the men here. Cathy ordered a second drink, her eyes explored the club like she was a petrol head trying to pick out one car in the worlds biggest supercar lot rather than a novice dominant seeking a submissive.

Her phone buzzed in her pocket - probably Jim, she ignored it. The night wasn’t about him anymore. 

Cathy waited until the server from earlier passed “Another glass of wine, please” 

“Is your friend coming back?” The server asked.

“Sadly, not”

The server claimed to be on a break when he returned with two glasses of wine. “He doesn’t share your interest?”

“No, guess it is a lost cause”

“Everyone here does… you could take your pick” the server giggled, emptied his glass, and stood “let me know if anyone takes your fancy Ma’am”

Cathy was tempted by the suggestion. She scanned the room for loners, singled out one, imagined how things might go between them - ordered another drink - scanned the room for loners, singled out another, imagined how things might go between them and so on. 

Next morning, sat on her bed, staring at her phone, Cathy took a deep breath, dialled his number. The phone rang a few times before Jim picked up, his voice hard, distant. “Yeah?” he answered, clearly not in the mood for small talk.

“Hey, Jim, I just wanted to apologise for last night. I shouldn’t have sprung that place on you like that.”

There was a long pause on the other end. She could hear him breathing, as if weighing his words carefully before he spoke. “I don’t know what you were thinking,” he said, his voice laced with frustration. “That place, those people, it’s not me. I can’t believe after the dress episode you thought it was a good idea to take me there.”

“I know, I know,” she said softly, trying to keep her tone calm. “I just thought… maybe if you saw it, you might be open to the idea. I realise now I was wrong Jim. Pushing you like that was wrong.”

Another pause. “You have to promise me something,” Jim said finally, his voice serious. “Promise you’ll never do anything like that again. And don’t ever ask me to wear women’s clothes. Never!”

Cathy swallowed, a small knot forming in her throat. She knew what this meant - exploring that part of her desires, would have to stay inside her head. That or break up and she wasn’t about to let go of their relationship.

“I promise,” she said quietly. “I won’t ever mention it again. I’m really sorry, Jim. I didn’t mean to upset you with my kinky fantasies… forgive me?”

Jim let out a sigh, the tension easing slightly from his voice. “Yeah, I forgive you. I just want us to be back to normal.”

“Of course,” Cathy replied, her voice barely a whisper. “I want that too.”

After another brief silence, Jim cleared his throat. “How about I come over next weekend? Take the week as a chance to reset.”

A small smile tugged at Cathy’s lips. “I’d like that, come for dinner and make-up sex?”

During idle moments Cathy’s thoughts would circle back to the club, the servers suggestion. It was in such a moment she had an epiphany - taking on a crossdresser who was already “finished” would be like buying an exquisite hand made vase and passing it off as her own work.

Cathy was back at square one.

4 - La Trattoria

Julie and Peter, Cathy and Jim, gathered at their favourite pasta restaurant, wine flowed, they enjoyed good food and good company. Julie stirred her coffee absentmindedly, her mind wandering as she listened to Cathy, Peter and Jim chatting.

Cathy volunteered herself as designated driver, she had been waiting for the right moment, and that time arrived, her heart raced slightly. Desert course she looked toward Julie with a mischievous smile. “So, Julie, did Peter mention it again?”

Julie blinked, confused “what?”

“Did Peter mention wearing a dress again?” Cathy grinned, Oh’d. “You already tried it?”

Peter’s face drained of colour, and he stiffened beside Julie. “You told Cathy?”

“Where did that come from?” She shook her head. “I’m not sure what you are talking about…” Julie was cursing inside, in a way Peter’s knee-jerk reaction served as an admission. 

“How could you forget Julie? You could not talk about anything else in the Uber that night” Cathy’s eyes revealed amusement. “You told me Peter wanted to wear a dress to relax. You really don’t remember?”

Julie’s heart raced, said she had been drunk that night and didn’t recall discussing anything like that.

Peter, still demonstrating what visibly embarrassed looked like, cut in quickly. “It is a simple misunderstanding. I was talking about an essay I read, in it the character de-stresses in that way while reading. Julie got it mixed up.” He shifted awkwardly in his seat. “You know how, sometimes, Julie half listens Cathy.”

Cathy wasn’t fazed. “I know how stressful your job is Peter, you should be able to relax however you choose,” she said, leaning back in her chair. “And honestly, Julie, I think refusing Peter is a little mean. After all, where is the harm?”

Julie’s stomach churned as she tried to process Cathy’s words. “I have not, and never will, change my mind about not wanting to see my boyfriend mincing around our home wearing a dress.”

“You could let me help, Julie” Cathy offered with a smirk. She rested her hand on Peter’s forearm “Wear anything you like and read anything you like at mine Peter.”

Jim had been quietly sipping his drink, thankful at not being mentioned, finally he spoke up. “That’s a ridiculous idea Cathy, Peter is not playing dress-up with you.”

Cathy rolled her eyes. “Relax, Jim. If Peter wants to read while wearing a dress, who cares? It’s harmless and it will be fun and safe, I don’t get visitors.”

Julie, now furious, glared at Cathy. “Jim’s right, you are being ridiculous! You are seriously suggesting I let Peter go to your place to de-stress by wearing a dress? He needs therapy not a damn dress.”

Cathy’s expression shifted slightly, growing more serious. “According to what I read online it’s not unusual for people de-stress in ways others might find strange, and as a friend I’m only offering to help, Julie. I cannot understand why are you are acting like this.”

Jim, growing increasingly agitated, glared at Cathy. “I’m not going to allow you to do this.”

“Allow me?” Cathy scoffed. “Peter will be in my house, Jim. And did I forget to mention that I do NOT need your permission.”

Julie, her mind whirling, glanced at Peter, who looked humiliated. “Cathy, drop it,” she said firmly. “We don’t need your help.”

Cathy smiled innocently, leaned back in her chair, summoned the waiter “can we get some brandies?” her voice calm and unbothered.

***

Cathy breezed into Julies cubical mid week, a coffee in each hand, Julie sat daydreaming at her desk, her thoughts drifting back to Cathy’s suggestion. She hadn’t brought it up with Peter since, but it hung around in her thoughts like a bad smell in a dentists waiting room. Cathy handed her a coffee “penny for your thoughts.” Julie shrugged. “So…” Cathy parked herself on the edge of Julie’s desk, “have you thought more about my offer?”

“Honestly?" Julie sighed, rubbing her temples. “I haven’t stopped thinking about it. Peter says he does not need to wear a dress if it makes me uncomfortable, promises he will not do it without my agreement, but I’m not so sure Cathy.”

Cathy raised an eyebrow, intrigued. “What do you mean?”

“What if he does when I’m not there and I accidentally catch him? It would change how I see him…” Julie used a sip of coffee to gather her thoughts “I’m already starting to think less of him as a man. It’s not something I’m proud of, but it is how I feel.”

“Julie, you’re being too hard on him and yourself. All men have a feminine side, most are too scared to admit it, Peter is actually braver than most men for even telling you.” Cathy set a hand on Julie’s shoulder “I hope I am a close enough friend to say you are the bad guy in this.”

“You really think so?”

“I do,” Cathy said, her voice steady. “In my opinion, it took a lot of guts to raise a subject like that. It doesn’t make him any less of a man - if anything, he’s more of one for trusting you enough to share.” She chuckled “I doubt he expected you to tell me though.”

“Or you talking about in public”Julie said with a smile, her mood lifting. 

After a pause, Cathy leaned in closer, her tone lightening. “Look, my offer still stands if you don’t want to deal with it at home. He can try out de-stressing at my place, no harm done.” Cathy thought about her and Jim. “My guess is he will run a mile when I hand him the dress.”

Julie frowned. “Sending him to try out his fetish with another woman seems foolish.”

“You don’t trust me?” Cathy chuckled, said Peter was not her type. “You know I like my men sweaty and uncouth, plus, there’s a simple way to make sure things cannot get out of your control…”

Julie gave her a questioning look. Cathy’s eyes sparkled mischievously. “You lock him in a chastity cage. That way, you’d have peace of mind knowing for sure nothing happens beyond him just reading and relaxing.”

Julie burst out laughing, caught off guard by the absurdity of the suggestion. “Peter… in chastity?” she managed between giggles. “Oh, Cathy, if it wasn’t so kinky it would be ridiculous!”

“I’m imagining him in my lounge room wearing a dress and a chastity” Cathy grinned, enjoying the moment. “And panties!”

“What?” 

Cathy sent Julie a few links “chastity and panties go together like a horse and cart.” Julie opened the first link as Cathy continued “it solves everything, you call his bluff and no funny business. If he goes ahead with it he gets to unwind, and you get peace of mind.” Cathy left her reading.

In that moment Julie felt the weight lift off her shoulders. That evening, she messaged Cathy:

Julie: Were you serious about what you said?

It didn’t take long for Cathy to reply.

Cathy: Of course.

Julie stared at the screen, her heart racing as she typed her next message.

Julie: What happens next if I say yes?

Cathy’s response was almost immediate.

Cathy: We sort out a day. Then, you tell Peter you’ve been thinking about it and you were being unreasonable before, you’re willing to let him try it on your conditions.

Julie’s fingers hovered over the keyboard as she reread Cathy’s message. Her mind spun with possibilities and doubts, she liked Cathy’s calm, confident approach.

Julie: And the conditions?

Cathy: Simple. You let him know it’s on your terms, adding the chastity is a safety measure, that’s your call, not his.

Julie stared at the message, her stomach twisting with a mixture of curiosity and apprehension. Could she really go through with this? It felt surreal, like they were talking about someone else’s life entirely.

She took a deep breath and sent one final message.

Julie: Need to sleep on it.

5 - The Chastity

Julie was hedging “do you think Peter will crossdress in secret like it says in that article?” Julie said as they sat alone in the office canteen. 

Cathy had been discreetly chip, chip, chipping away at Julie, avoiding mention of her offer and sending her links from the net. And Julie responded by sending Cathy stories of women who had come home unexpectedly. 

“Okay… let’s do this.”

Cathy picked up her iPhone, sent Julie an Amazon link. “This chastity is ideal, it’s the latest thing in chastity devices” Cathy giggled “although, I guess, Peter’s cock will soon be the latest thing in chastity. With or without I promise Peter will be safe with me Julie.”

“How long have you been looking at these things?”

“Since the meal,”

“What’s in it for you Cathy?”

“You know what it says online about crossdressing men being submissive, well, I’m a little intrigued to discover for myself if that is fact or fiction. Here’s the deal, I’ll buy his dress and in return you tell Peter he has to give it try for a set period, like a day a week or whatever suits you.”

“When he works Saturday he gets a day off during the week.” 

“Okay, I can take a leave day.” Cathy said.

Julie pressed the buy now button before she could change her mind “next day express.”

Peter said a package had arrived, handed it to Julie. She left it on the dining room table while they ate dinner. “I have been researching your crossdressing and I’ve reconsidered.”

“I’m not a crossdresser!”

“You sound cross” Julie giggled and tried to be playful while suppressing feelings of distaste. For Julie sexy stuff belonged in the bedroom, lights off, curtains drawn. The second she ordered the chastity she felt as perverted as Peter. She slowed her breathing, told herself lots of couples do real perverted stuff. And this is nothing by comparison. 

And Peter will be safe with Cathy Julie reassured herself, not like those men she read about online - paying some stranger and getting into goodness knows what situations.

Peter attempted to interrupt, she told him to hear her out first and apologised for acting unreasonably, “it must have taken a lot of courage to raise the subject and now I have had had time to think through your suggestion I have decided we will give it a trial on days you are off during the week” Julie leant close, kissed his cheek.

Peter interrupted, thanking her for reconsidering, promised he would make sure she never even saw the dress.

“I asked you not to interrupt.” Julie looked serious “so you agree without reservation?”

He nodded “yes, when can I start?”

“Tomorrow at eight, I’ll drop you off on my way to work and collect you on my way home.”

“Where am I going?” Peter looked sheepish.

“If you had let me finish there would not be this confusion” Julie wore her angry look and revealed that his days would be spent at Cathy’s house, said while she wanted to be supportive she couldn’t bear to think of him prancing around their apartment in a dress. 

Peter had a change of heart, he wanted to forget the whole idea.

“I’m sorry, it’s too late for that Peter. Cathy has already bought you a dress…” she picked up the package from the table “and I bought you a chastity.”

It was not in Julie’s nature to be mean, she almost gave in to Peter’s whining. “You expect me to send you to another woman’s home to live out this fantasy and I am supposed to hope nothing happens? I want you to go shower, Cathy said she read online first thing crossdressers do is to remove all hair, neck down” Julie giggled “perhaps Cathy will let you wear pantyhose with your dress.”

Peter tried one more time to change Julie’s mind “… Cathy does not really like me so why is she doing this?”

“She does too like you. Why would you think differently? And why else would I insist on this chastity thing? It’s getting late and I still have to try this on you.”

His erection made it easy for Peter to shave his privates close, he liked how, without hair, his cock looked more impressive than usual. He toyed with the idea of masturbating before deciding against, Julie would surely want sex after he had tried on the chastity. He returned to the living room wearing a bathrobe. 

Julie mentioned his cock looked almost impressive now it wasn’t hidden in a bush. He remained hard “I’ll try the smallest ring first” she threaded a ring along his shaft. Julie had researched ‘top tips for new key holders’ on line and was being careful to stay with the script. He ‘ouched’ a couple of times when Julie began feeding his balls through “first time lucky, look, the smallest ring fits perfectly” she said with a chuckle and ‘accidentally’ squeezed a testicle. As if his cock had also read the instruction manual, he softened. “Oh dear, I hope this isn’t too big.”Julie said as she clicked the cock tube in place. Leaving the lock in the box she took a similar one from her purse. 

“Why not use the lock that came with it?”

“That’s just a suitcase type lock, the locksmith promised this will not open with a paperclip.” Julie handed it to Peter, “lock yourself away for me.”

Peter clicked the padlock, tugged at the cage “even Houdini wouldn’t be getting out of this without a key.”

Julie was pleased she did not have to look at his cock any longer, to her eye the pink plastic cage had looked too small to house his cock, but he fit inside with a little compression. The way the chastity angled down gave, as the website promised, ‘a feminine outline in any outfit’ She asked if it felt comfortable.

“It’s quite heavy”

“The website suggests wearing something supportive” she took a bag from her purse “I do not think boxers will cut it so I got you these”

“Pink panties! I do not think so”

“Pink to match your chastity, says online all chastity boys wear panties”

“Ha, ha, I don’t see why you want me to wear them.”

“You cannot wear boxers with a dress silly.”

“Okay, I’ll wear them, now can you let me out?”

“Sure” Julie fumbled in her purse, laughed nervously “I must have left the keys in my desk” He looked grumpy, said she was to bring them home next day. Julie chuckled, saying he was in no position to issue orders.

Peter lay in bed, his back to Julie, a degree of grumpiness clear in his voice when he said goodnight. She spooned into him, playfully tugged at his chastity, remembering the instructions and said “just checking your little willy hasn’t slipped out.”

“Where the fuck is all this little balls, tiny cock talk coming from Julie?”

She kissed his neck and explained when she read the instructions it said men liked their key holder to talk that way when putting them in chastity. “I’m sorry, I am trying to make this fun for you, we both know I’m not good at this kinky stuff.”

“It hurts when you call me little.”

“Consider it the price you pay for wanting to wear a dress.”

Next morning Peter slipped the pink panties on, Julie had gotten the size spot on, they took the weight off nicely. He shimmed them up a little further running his hand over his butt. 

“When you are finished caressing yourself I have news” Julie stood, beaming,  in the doorway. He asked if Cathy knew about the panties. Julie said they hadn’t mentioned them and if he changed discreetly there was no reason for her to find out. She turned to leave “nearly forgot why I came here” she tapped her forehead with the heel of her palm “that was your boss on the phone, asked if you could work today.”

“You said no, right?”

“We can’t afford to turn down overtime, I said yes and cancelled Cathy. She was disappointed, she is taking Monday off instead.”

“Can you not be so organised for once?” He pulled on work clothes and headed toward coffee aromas. Julie was right, they always needed extra money. She was in a playful mood as they breakfasted, mentioning he use a stall to avoid giving the men a flash of pink. “Is that a line from the chastity book of humiliation as well?” He cut back at her.

“Mr gr-umpy. I’m being practical, chastity boys sit to pee. Beware workman’s cleavage in your cubical” Julie kissed him goodbye “men wearing panties only get one chance for a big reveal.”

Peter considered her remarks and needlessly thought through several cover stories while trying to imagine some unimaginable incident. He had worked for the company for 10 years without exposing his boxers so why was one day wearing panties playing on his mind.

Cathy doubled over with laughter when Julie told her of Peters overnight imprisionment. “If you forget the keys tonight Peter is in for a chaste weekend, not so much you.” Cathy knew her friend views on oral and wiggled her tongue while making slurping sounds.

“Do not be so disgusting” Julie huffed and walked away.

Julie arrived home early for a Friday, Peter smelt the takeaway food the moment the door opened, Julie had picked up their favourite curry and rice dish. She talked about  her day, how coworkers hurried her out of the office “That is why I’m home early Peter” She chewed slowly, mentally preparing for an argument “in the rush I forgot your key.”

Peter stared, threw his fork down “so I’m locked in this fucking cock cage all weekend?”

“Please don’t be so crude, you are wearing a chastity,”

“Crude? Why are you acting like it’s no big thing?” Peter looked crestfallen, mumbled “heartless bitch”

Julie decided two can play being nasty. “Judging by the size of your chastity, it IS no big thing” Julie lied. Keeping him in chastity seemed like a good way to make dress wearing as unpleasant as possible for him. Now she felt an animosity toward him, her voice took on a quiet angriness “this meal  was to say sorry Peter, but ‘heartless bitch’ me is regretting not staying in the bar.” 

6 - Day One

Julie stopped the car in front of Cathy’s house, the engine humming softly as she sat in the driver’s seat, her fingers tapping nervously on the steering wheel. Peter rode shotgun dressed casually in sweats and t-shirt, but there was nothing casual about the tension that hung between them in the way a dark, brooding presence would. Julie glanced across ” you certain you want to do this?"

“Only if you are certain you are okay with me doing it” Peter swallowed hard, his voice was quieter than usual. He wasn’t sure what else to say. This was something he wanted, but now that the moment was here, he felt his courage drain away as if he were first in line to ride the Kingda Ka.

“Okay, have fun" she said after a pause. "I’ll pick you up after work. Just… behave."

Peter nodded again, feeling the weight of her words. “Thanks for this love," he murmured, giving her a brief smile before unbuckling his seatbelt and stepping out of the car. Julie watched as, library book in hand, Peter approached the front door and knocked. Cathy opened the door, a mischievous smile playing on her lips as she waved Julie off. "Come on in, Peter.”

He stepped inside, the cool, quiet of her house contrasting with the warmth of the day outside. Cathy led him through the hallway and into the kitchen. Leading off the kitchen a back hallway lead to the rear door. Off to one side of that hallway was a small room, more like a junk room where, over time, Cathy, and perhaps her grandmother before her, had  piled boxes and old furniture. “You can change in there," Cathy said motioning to the door. Inside, an A-line sundress hung from a rail on the wall. It looked very feminine, its elasticated bodice flared out from the waist - a style Cathy considered ideal for a new crossdresser. Before the mirror , on a stack of boxes, lay a pack of pantyhose, and a pair of pink ballet pumps awaited an occupant. “I was unsure how far you wanted to go, you know, so I bought you pantyhose and shoes. I guess you know how to put pantyhose on…”

“Julie rolls them up.” Peter’s mouth went dry as he took it all in. 

“Julie said she had already put you in panties and chastity so it seems as if you have all you need, do you like your dress?” 

Hearing Cathy say Julie had ‘put him in panties’ made Peters heart skip a beat. Why did Cathy need to say it like that? ‘Wearing panties’ would have been bad enough but being ‘put in panties’ made it sound as if he were living out Julie’s fantasy. Realising Cathy was waiting for some sort of reaction he said the dress was perfect. 

“I’m sure you recognise it from when you searched Julies closet, looking for a dress to fit, Julie has an identical dress… but in her size of course” Cathy smiled teasingly “If you want something different for next time or need a bra or corset you just let me know.”

Answering would only give Cathy reason to continue talking and suggesting ore items of feminine clothing and he already felt adrift in a sea made from a mix of embarrassment and exhilaration. “This is it” a voice inside his head said, he was about to step into a world he’d only glanced within the pages of a book.

"I’ll give you a few minutes to change. When you’re done, come find me in the kitchen.” Cathy turned to walk away. ”And don’t forget shoes, the kitchen floor might be a little grimy.”

Peter nodded, his heart pounded ever faster as he undressed, stepping out of his sweats and t-shirt he stood in nothing but his chastity and panties. The book had not mentioned female underpants, and he had not considered them let alone pantyhose. In his mind he assumed he would simply take off his tee and joggers and pull a dress over his head. Hands trembling he opened the pantyhose and slid them up his legs. The smooth fabric clung to his shaved legs sending a shiver through his body. Peter wondered if women felt the same putting on their undies, he decided they must do or why would they make such a big thing about wearing stockings.

Slipping the dress over his head he caught a glimpse of himself in the full height mirror. The absurd image did not distract from the sense of calm that enveloped him. The elasticated bodice of the dress hugged his upper torso highlighting absence of breasts. His dress swished across his pantyhose as he wiggled his feet into the ballet pumps and fastened the little Mary Jane straps across his insteps. The shoes were light and comfortable. To Peter’s eyes they looked identical to a pair Julie owned. 

He felt a shift inside as if he were an actor playing a role and for the first time there was an upside to his chastity - it prevented displaying an embarrassing erection to Cathy. 

Peter took a deep breath and, ready to be ridiculed, walked into the kitchen. His soft sole ballet pumps allowed him to move soundlessly. Cathy jumped in mock surprise, a smile spread across her face. "Well, don’t you look lovely, a dress size or two  bigger version of Julie” she teased as she searched inside her purse “I guessed that might be what you wanted.” Saying they need bread for lunch she finally found her car key, “ring me if you need anything” 

“Where is your house phone”

“House phone?” Cathy looked surprised “they still have those? Your phone out of battery?”

“I do not have a mobile telephone” Peter smiled “Hence the library book.”

“Then it seems you will not be ringing me” Cathy got as far as the door, turned back “sorry about the mess in here, make yourself a coffee if you can find a clean cup. Just ignore it Peter, I’ll tidy when I come home while you read. I like to read in the lounge room, but you decide where is best.”

Cathy smiled to herself all the way to the market, pleased and surprised he had actually gone through with it. And who says ‘hence’ nowadays?

Peter hesitated, he washed the moka pot and a cup for coffee and, having filled the sink with hot soapy water, decided to finish the dishes as a thank you for Cathy going to so much trouble on his behalf. Unsure where to stop he pressed on, cleared the kitchen table and counters, wiped them down and washed the floor. Seeing the mess waiting in the lounge room Peter sat at the kitchen table and opened his book. Cathy looked stunned and embarrassed as she piled fresh bread and groceries on the counter “you must think I’m a real slob” 

“Of course not, it must be hard managing a house and working full time.”

“I am gasping for a coffee… I need the toilet first.” She took her time, saw a text from Julie on her iPhone.

Julie: did he go through with it?

Cathy: he looks so sweet.

Julie: UGH do not say any more.
Julie: so he REALLY went ahead with it?

Cathy: took to it like a fish to water

Julie: don’t fish hatch in water?

Cathy: Pedant!

Peter had fresh coffee brewing and sandwiches ready. Cathy feigned guilt “I am a terrible host”

“Nonsense, I’m glad to be able to start repaying you for buying me these clothes.”

“Is it like you imagined” Cathy smiled kindly, “like in that book you read?”

“I’m shaking now” Peter said holding out his hand “doing the dishes calmed me, now I’m a bag of nerves again.” Peter smiled, said he often did chores after work said it relaxed him after a day of stress and dealing with angry customers.

“Hence avoiding owning a cell phone?” Cathy smiled at her use of ‘hence’ back at him.

Peter mentioned coworkers, and Julie, called him a dinosaur, “my coworkers live their lives serving their company smartphone twenty four seven. Would they be as happy if those same bosses put a ball and chain on their ankle?”

“Ahh, so no work calls after you leave the building” Cathy said

“They try calling on the house phone, I have caller ID”

“So, I guess today must be heaven for you in more ways than one” Cathy waved abstractly yet more at his clothes than the room. Swinging back to earlier she said “if doing chores helps that is fine by me. You go pick another room and go calm yourself… and if Julie asks we’ll just mention you reading your book.” Cathy chewed slowly. “How does that sound?”

Peter smiled, thanked her, took her up on the offer “to be frank Cathy I was having difficulty concentrating on the book.”

“You want to know what I think?” 

Peter remained silent. 

“I’ve been googling, researching, now I think wearing a dress while reading to de-stress was a ruse. Would I be correct if I said you never intended reading?”

“You are the one suggesting I do chores and I happen to be wearing a dress…” 

“I was not the one who mentioned the calming effect of chores Peter. Next time you come you can read or clean, not both. Which is it to be?” He remained silent, Cathy smiled at his discomfort.

“I would be repaying your kindness if I clean a little next time, that way we both get something” Peter looked nervous “I will still bring my book.”

Cathy let the silence stretch, her eyes never leaving him. “Now we both know you want to clean for me…” she began, “I will expect a certain level of… behaviour."

Peter’s heart skipped a beat. "What do you mean?"

Cathy leaned forward, her voice low and authoritative. "Now that you’ve decided being my domestic is a better way to de-stress, you will follow rules I set. No complaining, no slacking off, and no stepping out of line. Is that okay?"

“That sounds reasonable” Peter said knowing he was agreeing to something completely different - not bad-different just different-different.

Cathy smiled, satisfied with his response. "Good. Now, as for your afternoon tasks. I would like you to clean the lounge room; vacuum rugs, dust the bookshelves, polish coffee tables and so on. If you have time, you can clean the downstairs toilet."

Peter glanced down as Cathy spoke, each task she listed an act of submission to her authority. 

"One more thing," Cathy added, her tone light but serious. "While you’re here, would you act like a domestic, you know, be silent unless I speak to you. Would that be okay?"

Peter swallowed hard, nodding. “Sure.” It was as if Cathy could read his thoughts and take them to a whole new level. Daydreaming as he cleaned he thought what he was doing might be exactly what he had wanted from Julie. Perhaps, in time, Cathy could persuade Julie to accept this side of him. His thoughts drifted, he found himself smiling as he looked around the clean lounge room. For the first time in a long while Peter felt like he was doing something that made a difference. 

Cathy surveyed his work with a critical eye, inspected each surface with deliberate care, ran fingers along the edges of the bookshelves to check for dust. "You're a natural," Cathy remarked as she straightened up, her voice cool but approving. "But next time I will expect more attention to detail, especially in the corners. The kitchen isn’t spotless, either."

Peter swallowed hard, nodding, feeling the weight of her words, every time Cathy mentioned a flaw in his work, his stomach knotted with a mix of embarrassment and determination to do better. 

Cathy sat on a sofa, watching him as he re-dusted. She asked him about his experience, if the day was all he expected.
“Everything I expected and more, I’m worried how Julie will react when I tell her about cleaning.”

“I’m not sure she wants a blow by blow account of your day.”

“I will say I tidied the kitchen ready for lunch.”

“Sure, that sounds like a car in the drive now, why don’t you invite her in for coffee?” Cathy said casually as if she did not know how Julie would react.

Peter hesitated, his face flushing slightly. "Julie… well she doesn’t want to see me dressed like this," he admitted, feeling awkward even saying the words out loud. "She warned me not to ‘parade myself’ before her."

“Warned?” Cathy’s eyebrows arched, but she smiled. "I see. Well, you go change while I go talk to Julie outside."

He nodded quickly, hurrying back to the small room where he had changed that morning. 

Cathy stepped outside, Julie was parked on the drive. She walked up to the driver’s window. Julie rolled down the window, shrugged, “so, he stuck with it”

“I fully expected him to back out when he saw what I bought for him.”

“Information overload!” Julie sighed, her voice low and a little tense. "Cathy, you will keep this between us, right?"

"Of course," Cathy replied, placing a hand on her chest as if swearing a vow. "I won’t say a word to a living soul. But I have to tell you, I have enjoyed today more than I thought I would.” Julie and Cathy watched Peter step out of the house and walk toward the car. As Peter sat in the car Cathy said “Thanks for coming Peter, see you next week.”

***

Julie pulled off the drive, asked if he enjoyed his day. Peter said he did,“great book and a whole day of being uncontactable has left me so relaxed, did you know Cathy does not have a house phone?”

“Sure… did you feel trapped?”

“Not trapped, more safely isolated. Thank you for setting this up for me Julie.”

Julie smiled “am I still a wicked bitch?”

“No, you never were” Peter covered her hand with his, apologised saying it was nerves, now he had gotten through the first day it would be easier next time. “Julie, how does Cathy afford a house like that on one wage”

“Her Grandmother bequeathed the house to her along with the wherewithal to keep it. Don’t mention that to Cathy, she is embarrassed by her house”

“It’s a real gomi-yashiki Julie”

“Trash-mansion!!! Now who is a wicked bitch?” Julie giggled “I meant Cathy is embarrassed to own a big house.” 

Peter asked her not to repeat his comment. 

Julie laughed “I know it is uncared for, her grandmother would turn in her grave if she saw the house the way it is now.”

“I even had to do dishes to get a clean cup for my coffee”

“Yea, it’s a big house to manage alone, Cathy said you helped out in the kitchen. Perhaps you could do a few chores as a thank you for helping us?” Julie stopped at the lights, kissed his cheek, chuckled “Make sure to stand up for yourself from the get-go, once you start helping Cathy she will try piling more and more onto you just like she does to weak coworkers.” City streets passed by as Peter gathered his thoughts. 

Julie spoke first “thanks for not mentioning clothes.”

7 - The Routine 

Julie pulled to the kerb, took a key from the coin tray “Cathy said to let yourself in the back door, she will be back around lunchtime.” Peter changed in the storage room, pinned to his dress was a list of chores the last item ‘make lunch by 1:00.’ On top of the boxes was an old fashioned apron that he assumed Cathy intended him to wear. He put it over his head and fastened the waist with a bow. Walking into the kitchen he looked around with dismay. 

Under a week had passed and the kitchen looked as if eight left handed students, late for midterms, had left in a hurry.

***

Walking through the spotless kitchen Cathy realised he was already an incredibly efficient and hard worker. The list of tasks  provided motivation and he had gone at it like a human dynamo. She found him on his knees in the back hallway scrubbing the victorian tiles with such a ferocity that details, not seen in generations, were being revealed. She complimented him on how much work he had done and re-tied his apron “I found the pinafore in a kitchen drawer, must have belonged to a one of granny’s cleaners. I thought you might like it” 

While washing lunch dishes he mentioned Julie’s suggestion “half cleaning and half reading” hopeful Cathy would take the hint and let him relax for the afternoon. 

Instead of replying Cathy asked if he would mind changing her bed before he left. “Close your eyes when you go in, I left in a hurry this morning.”

“Okay” Peter smiled at the way Cathy added cleaning her bedroom while changing her bed without actually asking him to. 

Peter, Julie and Cathy settled into a routine that suited one and all. 

One morning a week Julie dropped him at Cathy’s house. 

One evening a week Peter dreaded the drive home in case Julie said she wanted him to stop.

***

“I was wondering Peter, would you like something different to wear next time?” Cathy asked one lunchtime.

“Like what Cathy?”

“Something more suitable, how about the sort of clothes a cleaner wears rather than a summer dress, it hardly goes with your pinafore.” He didn’t answer. “I thought wearing a dress might be something you would shy away from that first morning Peter,  but here we are, on your fourth, no fifth day you have visited…”

Peter interrupted “today is day six Cathy.” 

“I stand corrected, day six and here we are planning next time. One outfit is not enough, I promise to find something better for you to wear as a thank you for being so helpful.”

“Thank you Cathy, I think I hear a car on the drive.” Peter said and ran to what he now thought of as his room to change while Cathy went outside to meet Julie. Peter sat in the passenger seat and listened to their conversation…

Cathy was saying “with Peters help I am just about keeping most of the downstairs in order. Speaking of which…" Her voice trailed off, "I understand Peter is off next weekend and Jim’s away on one of his hiking trips with his friends.”

Peter stiffened slightly in his seat, sensing where this conversation was heading but unsure if he should say anything. He stared at the dashboard, willing himself to speak up.

"So," Cathy continued smoothly, “I was wondering, if you don’t have plans that is, if I could collect Peter from yours first thing on Saturday and keep him for both days. I think we could make real progress in two days."

Peter’s heart raced. Two days? He was about to say a whole weekend is too much when Julie spoke.

"That’s fine," Julie said without even glancing at Peter, her eyes fixed on Cathy. "It’ll have time to read, pamper myself, a little ‘me’ time.”

Peter blinked, stunned. He had expected Julie to protest, to say that a whole weekend was too long, that he needed to be home. But she didn’t. Instead, she seemed perfectly happy at Cathy’s request.

Cathy waved them off, Julie turned the car onto the road, a strange quiet settling between them. 

Julie was in one of the pre-menstrual moods he dreaded. Her coworkers knew to steer clear when the beast visited, and Peter had become adept at navigating those emotional waters. Julie casually asked if he had bought spare underwear.

"No," he replied cautiously. “Perhaps we could go together sometime."

Julie sounded angry-surprised he hadn’t followed her earlier suggestion to buy extra pairs of panties during his lunch hour from work. “One pair of panties is not enough for one day a week Peter, and certainly not enough for a weekend” Julie held up fingers as she counted off “Saturday, Sunday, plus a couple of spare panties to leave at Cathys. We can go now and pick out some new ones. The girls at work were talking about a lingerie store today,” Julie looked serious for a moment “I thought of you."

Peter, staring into ’the face of the beast’ knew better than to resist. “Thanks Julie”

At the lingerie store Peter acted like boyfriend following along while girlfriend shopped. As they walked down the aisles, Julie urged Peter to pick out some panties he liked. "You should stick with bikinis—they’ll work better with your chastity," she added casually. “Don’t forget to buy spares to keep at Cathys’ for when you stay over or have an accident."

Peter leaned closer and whispered, "Keep your voice down."

Julie raised an eyebrow, her temper barely contained. "I fail to understand why you're embarrassed. I’m the one helping a man choose panties."

A wandering sales assistant approached, she had been lurking, discreetly listening. "Can I help with anything?"

Julie smiled innocently. "He's just deciding about boy shorts - wouldn’t that be ironic?” With a smirk, she busied herself with browsing leaving Peter to handle the sales assistant.

Sensing a chance to increase her sales commission she launched into upselling mode. "Have you ever tried thongs? Once you do, you’ll never go back to briefs."

Before Peter could respond, Julie re-entered the conversation "he usually wears bikini style - says they hold his chastity secure," she said.

The sales assistant’s professional smile didn’t falter. "In that case, control panties might be a better option to hold you nice and secure. They’re a bit more expensive, but, I am sure you will find they’re worth every penny." She led him to another section. As if sharing a state secret, she confided, "They look just as feminine as bikinis but will hold your chastity thing nice and snug."

Level nine embarrassed Peter nodded, she pointed out matching bras and asked if he wore one. “No only panties today," ‘today’ he could have kicked himself for adding that, he quickly picked up a pair in each colour “I think this will be enough.”

“Not for every day, what are you a size 8?” The assistant smiled knowingly as she picked up, commission enhancing, second pairs in each colour. “Trust me, you do not want to be constantly washing your undies.”

Back home, Julie playfully suggested he try on a pair. Peter, sensing sex, quickly stripped off his clothes. Julie held out a pale blue pair of control panties, he wiggled into them as she watched with an amused smile. "The assistant was right, barely a hint of cock" she said, chuckling. "I expected you to try them with your chastity."

Peter, hesitant but compliant, agreed and soon locked his chastity device in place before pulling the panties back up. Julie’s mood seemed softer and not wanting to recall the beast he went along with her suggestion they watch a movie. He threw on a tee and sweats, and they settled down on the sofa.

As they readied for bed Julie needlessly mentioned her period was due. "I know what you usually get up to during period week," she said, her tone sly. "Why don’t you keep the chastity on? That way, we’ll both be out of action.” Peter looked at her, asked why she was being so mean. “I was reading up on chastity play… how men pretend they don’t like it, exactly like you do.” She said how key holders acted meanly because, secretly, that is what chastity boys crave. “If you can’t last the few days of my period I will let you out for a wank.”

“Thank you…”

Chastity lasted for a week, plus an entire weekend at Cathy’s house. Peter decided his hobby had gotten out of hand. Cathy and now Julie seemed to have their own agendas, he decided it was time to go back to slow things down. He cooked Julie her favourite spag-bol, opened a bottle of her favourite wine. “I think a whole weekend at Cathys is too much Julie.”

“Does that mean you are tiring of crossdressing?” Julie said hopefully. 

“No, it’s not that, cleaning is hard work and I did not expect Cathy would be so demanding, so strict.”

“Did I or did I not warn you not to let her take advantage?” Julie noticed how Peter no longer baulked when she crossdresser labeled him. “Just stand up to her for goodness sakes.”

Peter tried and approach from a different direction “I think leaving you alone for a whole weekend would be selfish of me.” 

Julie said how sweet he was - always considering her feelings above what he wanted. Julie shrugged, “you did promise Cathy you would, and I am looking forward to a little ‘me’ time.”

“Can I at least come home Saturday night, you know, go back to Cathy’s on Sunday?” 

***

It was a quiet Wednesday afternoon in the office. Julie sat at her desk, trying to focus on her report, but her mind kept drifting back to the earlier conversation with Cathy at the coffee machine. Cathy had spoken so nonchalantly about how she couldn’t imaging managing without Peter’s help around the house, as if in facilitating his new hobby, Cathy had smoothly transformed him into her domestic.

Cathy walked over, leaning against the cubicle wall. “So,” she said with a smile, “how are you feeling about this weekend?”

Julie glanced around to make sure no one could overhear. “I don’t know, Cathy. The whole point of sending him to you was to put him off this crossdressing thing.”

Cathy crossed her arms, leant against the desk. “I do make it unpleasant Julie. I load him up with chores, criticise him every chance I get… but he just seems to thrive on it. The minute he puts on that dress, he’s acting like the perfect little domestic. And he is so completely submissive.”

Julie’s eyes widened. “Wait… you’re enjoying this.”

Cathy hesitated, then sighed. “I didn’t expect to, but yeah… not just enjoying, I am longing for him to be there. The power, the control over a man - it’s something I’ve never really experienced before, and… it’s kind of addictive.”

Julie frowned, sensing something deeper. “And Jim? Does he know about all this?”

Cathy’s expression tightened. She shifted uncomfortably, glancing away. “Jim wanted to see Peter in the dress. Wanted to come over and tease him.”

Julie narrowed her eyes, sensing a tension beneath Cathy’s words. “Did you let him?”

Cathy shook her head. “No, I promised you I would not hurt Peter. I told Jim he couldn’t. I banned him coming around while Peter is there.”

Julie leaned forward, her curiosity piqued. “How did Jim take that?”

“Not well, he demanded I stop having Peter over” Cathy exhaled sharply, her shoulders slumping. “It got to the point where he gave me an ultimatum. It’s Me or Peter he said. You know how I react when backed into a corner Julie, you can guess the outcome.”

Julie stared at her, wide-eyed and stunned at her commitment to indulge Peter.  “You split with Jim because of all this, chose Peter over Jim?”

“I am glad we are having this conversation, I realised a while ago it was getting out of hand but let it continue.” Cathy hesitated. “I will put a stop to Peter coming to mine, before it threatens our friendship.”

“Our friendship is solid” Julie was taken aback. “Look Cathy, if you want to carry on I am okay for you to encourage Peter.” Julie went on to say how she considered Peter less and less of a man as time passes, “I decided to let this play out a while ago. Let the cards fall as they will… if you are okay with that.” 

Never a person to look a gift horse in the mouth, Cathy accepted Julie’s offer.

“That settles the matter…” Julie smiled “Do you wonder if Peter is drawing you into his fantasy? He thinks he is being clever when he tries to discreetly manipulate me. My guess he mentioned he had next weekend off more than once.”

“The sneaky bastard!” Cathy exclaimed. “And he says chores multiply faster than he can clean in ‘just’ one day.”

Julie said now they had an agreed plan of action she would let Cathy lead. “And it’s better for him to do it at your house where we can monitor him than have him sneak off to some strangers house or worse, right?”

“All I can think of right now is making him regret tricking me into suggesting a weekend and having me think it is my idea!” 

“Give him hell” Julie smiled. “At least you and I will enjoy our weekend.”

8 - The First Weekend

Saturday morning Julie was sat at the kitchen table wearing a bathrobe and towel around her damp hair. Peter passed her a coffee, a feint shake in his hand. Julie smiled asked why he was shaking.

“Working the whole weekend feels sort of scary now.” He was dressed in his usual attire: sweats and a faded tee. “And Cathy picking me up is new, I will be stuck there until she agrees to bring me home tonight.”

Julie shrugged, decided to test Peter, “then call Cathy, tell her you changed your mind, and come with me to the beach instead.”

Peter, realising his weekend was under threat, checked the time and said “I would love to but Cathy will be nearly here now.”

“I am glad you decided not to let Cathy down at the last minute.” Julie felt a little pleased he would not be disrupting her weekend. Julie was still mid- coffee when Cathy arrived saying she had time for a quick coffee. She almost ignored Peter saying they could chat all weekend and sounded excited at telling Julie how, with Peters help, her house would be nearly tidy enough for her parents to visit “I have been ashamed to let them see I have let Grandma’s fall into such a mess.” With that she picked up her keys and hustled Peter to her car.

“Where are we going?" Peter asked as Cathy drove in the opposite direction to her house.

"You'll see.” Cathy filled the drive across town with talk of the tasks that awaited him. Peter couldn’t shake the feeling that something seemed different in her mood. 

Julie would have instantly recognised the glint in Cathy’s eye to be the one she had when she was up to something.

After about twenty minutes, Cathy pulled into the kerb on the far side of town, an area new to Peter. The shops lining the street were older, more old fashioned stores that didn’t exactly match Cathy’s usual shopping style.

"Come on," Cathy said, hopping out of the car. She seemed eager, hustling him along as a sheepdog would a stray lamb. Peter froze as Cathy put her hand to the door of a small, old-fashioned shop, the sign above read: 

 “Eve’s Corsetry and Fine Lingerie."

“I’ll wait outside Cathy..." Peter began.

“Nonsense, I promised you better clothes and, like they say, ‘any project is only as strong as its foundations’ that is where we are starting todays project, unless you want me to take you back home…” Cathy was already opening the door, Peter followed her inside. 

The scent of polish filled the air giving the shop an old worldly quaintness with it’s polished wooden floors and rows of corsets, bras, and lingerie adorning the walls. Mannequins wore undergarments which, to Peter’s eye, seemed to be items of torture from another era. Peter felt a sudden flush of heat rise up his neck, a need to turn and run.

Cathy greeted the shopkeeper - a middle-aged woman with warm eyes and a knowing smile. She had shoulder length, greying hair styled in a curly mid-century style and wore a tailored blue dress. The way Eve held herself erect portrayed a school ma’am look of inner authority.

Cathy nodded and smiled. "Eve, nice to see you again.” 

 

“Cathy! And this must be Peter," Eve said, turning her attention to him. Peter, still too stunned to speak, gave a sheepish nod.

Cathy grinned and without hesitation said, “I brought Peter in for corseting as we discussed Eve.” She let out a soft chuckle, then added with a teasing tone, "Actually, I get the impression Peter wants to be corseted, but is too shy to admit it."

Peter's eyes widened as Cathy spoke, his mind scrambling for words that wouldn’t come. His cheeks flushed with embarrassment. Before he could say anything, Eve spoke “relax, Peter" she said with a reassuring smile. “rest assured I’ve had many gentlemen customers who see a corset as the crossdressing foundation.”

Peter’s heart raced. If his sneakers weren’t fashioned from an element denser than lead he would have run out of the shop that very second. He wanted to say so many things - he was not a crossdresser - he did not want a corset - he wanted to say he only wore a dress. But, at that moment, speaking aloud also proved to be as difficult as walking.

Eve lightly placed a hand in the small of his back releasing him from the spot. Guiding him toward the back of the shop she pulled aside a thick velvet curtain revealing a private fitting room, she motioned for Peter to step inside. 

Cathy gave him a little encouraging wink. “No need to be shy Peter.”

Peter stepped into the fitting room of doom. The room was compact in a cozy way, and had soft, flattering lighting. A large mirror filled one wall and stretched from floor to ceiling. Eve followed him in, cloth measuring tape and small notepad appearing in her hands as if by magic.

"Okay, Peter," she said gently. “Undress down to your underwear so I can take your measurements."

Peter hesitated for a moment, at least he would never meet the woman again he reasoned as he undressing revealed his pink panties and contours of his chastity. 

Eve began measuring as if not noticing. Her hands moved swiftly, measuring his waist, chest, and hips. She made small, professional sounding comments as she worked, mentioning how slim Peter was, mentioning how his frame would fit perfectly in one of her steel-boned waist training corsets.

Cathy pretended to browse but was very much listening to the conversation. She smirked when she heard Cathy mention the waist-training corset. It  impressed Cathy how Eve had only mentioned why he was being measured after she had all she had finished.

Eve stepped back and considered for a moment before going to the stock room. Eve returned holding a pink, steel-boned corset. The corsets eight metal suspenders, dangling from straps, jingled against each other like wind chimes signalling the approach of a bunch of hippies.  “This colour goes nicely with your panties.”

Peter's eyes widened as he stared at the garment.

"This corset style is sturdy yet elegant. Breathe in. It will give you a lovely feminine shape without being too restrictive," she explained while fastening the metal busk. Her hands moved with a precision that signalled experience, deftly tightening the back laces. As the corset constricted him, Peter felt a strange mixture of emotions. Forgetting a boa constrictor for a moment, the corset was tighter than anything he could imagine, and yet not unbearable. As she worked the laces ever tighter Eve scooped his chest fat up from the confines of the corset “we don’t want that going to waste.” 

To Peters horror the mirror revealed his chest hanging over the top of the corset, he instinctively crossed his arms over it. “too tight Eve.”

Cathy chuckled softly. 

"I’ve been fitting corsets for thirty years, dear. I know when tight is too tight.” Eve tied the laces off.

Peter looked at himself in the mirror, the his waist was cinched in looked out of place on a man. He couldn’t wait to be back in his own clothes, before he could suggest that, Eve held out a pink bra. "Slip your arms in," she said kindly.

Peter froze, “I don’t need a bra!”

“Better to wear a bra you don’t need than need a bra you don’t have.” Eve quickly moved his arms for him and fastened the bra around him before he could protest. After adjusting the shoulder straps Eve stood back to admire her work.

“Perfect size, not too big, not too small yet room in case your man titties grow a little.” Eve said with satisfaction. Then, like a conjurer revealing a seal balancing a red and yellow striped ball on it’s nose, Eve swished her arm across Peter “ta-da, Cathy, come see."

Cathy stepped into the fitting room, her heart skipped a beat. “And you put him in a bra as well, that is just perfect Eve.” Cathy circled around Peter, examining the fit of the corset and bra.

“The bra is from the ‘add a cup size’ range, dont you love the way it creates a little cleavage.” Peter saw the pack of stockings in Eve’s hand, he decided to play along - that would spoil their fun, to their surprise he reacted with enthusiasm. “Oooh, stockings!” He enthused.

Eve asked Peter to sit, he pointed his toe the way Julie did as Eve held out the rolled up stocking, stood when she told him “remember to always thread your suspenders through your panties.” 

Peter walked back and forth in the changing room, “Oh, I love the way my stockings feel Eve, they tug against my suspenders with each step.” The surprised looks Eve and Cathy wore almost made him snigger. 

Peter the controlled had become Peter the manipulator. 

Then Eve said something that turned the tables on him “Will you have Peter wear his new underwear Cathy?”

Cathy smiled, nodding enthusiastically, “it will save time, hurry up and put your drab man-clothes back on Peter, housework awaits.” 

Eve was smiling, her voice light “real job satisfaction comes when a customer wants to wear their new lingerie right away."

Peter feltl his heart pounding. “People will stare, please don’t make me go outside like this Cathy.” His voice wavered, and he could hear himself whining.“This bra… it makes my chest look big.”

Eve, standing behind the counter with her arms crossed, let out a soft chuckle “Don’t act so precious Peter, a sissy can never get enough attention,” she said, her tone light but teasing.

Peter’s eyes widened. “I’m not a sissy!” he protested, his voice a mix of shock and embarrassment. Cathy raised an eyebrow but did not interrupt, happy to watch him squirm.

Eve’s voice was laced with amusement, “if it looks like a sissy and whines like a sissy, then it probably is a sissy.”

“Wait Cathy,” Peter tried one last time “I cannot wear this corset and bra.”

“That is not true, is it Peter?“ Cathy said in a tone normally reserved for naughty children “just look… you are wearing your corset and bra.”

Once they were in the car, he could hardly contain himself. He turned to Cathy, his voice full of anger. “Why the fuck are you treating me like this? I can’t believe you humiliated me like that. I can’t wait to get to your house and get out of this device of torture.”

“Do not be so selfish Peter! You have spent enough days with me pampering you, have you considered corseting you might be my fantasy?” Cathy glanced at him, a satisfied smile playing on her lips as she pulled into traffic. “And I saw how you looked at yourself in the mirror when you thought no one was looking.” Cathy gave his knee a gentle squeeze “Julie knows nothing of this and I will not judge you Peter, just relax and let me have fun.”

***

Peter sulked silently in the passenger seat, his corset so tight he could barely breathe. He replayed what Cathy had said, he should have expected there to be payback for the days she had played employer to his domestic helper. “I am sorry I acted selfishly and spoilt your day Cathy.”

“You have not spoiled a thing Peter. I expected you to resist before submitting to my control.” Cathy smiled “angrily shouting at me just then was a perfect one time reaction.”

 

He was still trying to wrap his head around what Cathy wanted from him when he noticed they were driving through an industrial/retail estate. Cathy navigated the roadway between large warehouse buildings and business units with the speed and confidence of a small mouse in a dry stone wall. “Where are we going?” 

Cathy didn’t answer right away, after a few moments she said “you’ll see soon enough.” She pulled up in front of a building "Industrial Uniform Suppliers" the sign said. Realising his humiliation was not over his heart sank. He glanced over at Cathy, but she only gave him an encouraging smile. “Come on, time to prove to me you are being as supportive as you claim you are.”

Peter followed, they entered the showroom, along the aisle manikins displayed coveralls, hotel workers uniforms, cleaners uniforms. He focussed on the cleaners uniforms, some buttoned up the front, some had a pinafore over, some had a tabard…

The uniform store was a far cry from the humiliating lingerie shop they’d just left.  Cathy led him further inside.

A tall, professional-looking sales assistant approached them, a smile spreading “hello Cathy” 

“Hi Angela, this is Peter.” Cathy smiled, they cheek kissed.

“So nice to see you, is this a  social visit or…” Angela said using a hint of surprise in her voice to mask the fact she and Cathy had role played the visit. 

“I’m here to buy a uniform for my maid,” she announced. Cathy grinned, unable to hide how pleased she was with how the day was going.

Staying in character Angela raised an eyebrow and nodded “do you know your maid’s size?”

“I’m not sure…” Cathy’s smirk deepened as she turned to Peter “so I brought him along for a fitting.”

Peter’s eyes widened in shock. 

Angela, staying perfectly in character, kept her tone polite. “Ah, I see,” she said, eyeing Peter up and down as if assessing his size. “This way to the changing room Peter.” As the passed she took a couple of maid uniforms from a rack. 

The maid uniforms represented a visual definition of humiliation and servitude to Peter. He finally understood there was an ulterior motive to Cathy’s willingness to let him visit, and her encouragement to clean. Her bossy nature should have set alarm bells ringing. 

Angela held a maid uniform up to judge his size.

He noticed Angela already knew his name… Eve and Cathy had met before - background research on Peters part was needed.

As far as Peter was concerned the weekend would count as payback in full, he decided to go along with what Cathy wanted for the rest of the day then no more visiting Cathy.

He would go out with a bang!

Angela spoke a little louder “I said slip those scruffy clothes off for me sweetie,” 

At that moment Cathy was in awe of Angela, she had feminised Peter with one word - ‘sweetie’ - Angela had demonstrated expertise at manipulation and pulled him a step further into maid cos-play. There was a power in the way Angela spoke, a technique Cathy needed to learn if she was going to play the game successfully.

Angela wasted no time. “Now, let’s see how well this fits,” she said pulling the curtain closed. She watched him undress, Peter stood awkwardly in his corset, bra and panties as Angela held up the black uniform dress, her eyes flitting here and there taking in what he wore. She smiled, impressed by the control trainee-mistress Cathy already wielded over him.

“I must say, I love your corset sweetie, it is the perfect symbol Cathys’ control over you.” Peter felt a fresh wave of embarrassment and didn’t bother to answer. The black uniform was too snug around his waist for the back zipper to slide up. “No one will know Cathy has corseted you while you are wearing this” Angela frowned slightly at the inconvenience. “Hmm, this one’s a little too small for your waist,” Angela was already untying the laces at the back of the corset and pulling them tighter, ignoring his complaints. The sensation of the corset squeezing his waist was both thrilling and terrifying.

“You’ll have to watch your weight, sweetie, perhaps drop a couple of pounds” Angela said lightly, her voice teasing as she zipped up the back of the dress which now fit like a glove. “How’s that?”

Putting aside the shame of wearing the ridiculous uniform Peter kept to his plan to please Cathy. “It seems like it was made for me Angela, does this costume come with an apron or a headdress of some sort?” 

Cathy remembered how Peter had manipulated her in the past. She recognised his sudden enthusiasm for what it was…manipulation. She set her iPhone to video seconds before Angela  guided Peter out of the cubicle, one hand on his back.

“Do a 360 for your Mistress,” Angela instructed, spinning Peter gently so Cathy could see him from all angles.

Cathy gasped, not only at the sight of Peter in the uniform - that surprised her -  but at Angela’s use of the word Mistress. The word sent a rush of excitement through Cathy. 

Mistress was not a real world title she had imagined for herself, yet Angela’s casual use of the title solidified it in her mind. Now Mistress was out of the bag she would fully embrace being ‘Mistress.’  Cathy admired Angela’s handiwork. “It is so formal, don’t you just love it Peter?”

 Unsure how far to push his mock enthusiasm he shrugged, nodded, “very formal.”

***

Angela took a lilac day uniform from the rack along with a full apron, half apron, and a lacy mop cap. “Back to the fitting room sweetie. This is more suitable for a cleaning uniform,” Angela enthused. Peter had become so caught up in what Angela was doing he had failed to notice Cathy holding her iPhone up. 

“If you can bear to take the black uniform off I need to make sure this fits.” Angela had noticed Cathy filming and left the curtain open, she played to camera re-saying how cute his underwear was as she zipped him into the lilac maid uniform “oh, this colour looks so cute on you sweetie.” She tied the half apron around his waist in a big bow, Peter stared at his reflection in the mirror. Angela looked pleased as she positioned a mop cap on his head  “the final symbol of submission.”

With them both facing the mirror Angela said “try a little curtsey for me” she smiled when he complied “no like this” Angela demonstrated “again” she instructed stepping away and guiding Peter toward the open curtain “that’s better, one more time…” He slipped one foot behind the other and curtseyed to Cathy.

“Isn’t he just a perfect little sissy maid?” Angela enthused.

Peter’s head was spinning, he finally noticed Cathy videoing. 

Cathy was beaming. “Oh, I love it!” she exclaimed, clapping her hands together. “You look absolutely adorable Peter.” 

While Cathy and Peter admired his uniform, Angela quietly gathered up his clothes along with the formal black uniform and took them to the counter. Peter barely noticed what was happening until he turned around and saw Angela neatly wrapping a package.

“Wait, I need my clothes…” Peter began, but Angela had finished wrapping his clothes in brown paper and was placing the formal uniform into a dress carrier.

“Here Peter take these,” Angela said, her tone cheerful but firm.

Peter’s eyes widened. “But I can’t go outside dressed like this! What will people think?”

Angela smiled sweetly, meeting Peter’s panicked gaze. “Oh, sweetie,” she said, her voice dripping with playful condescension. “They’ll think a lucky sissy maid has been bought beautiful new uniforms by his mistress. Just be proud of what you are.”

Peter’s face burned with embarrassment. He looked to Cathy for help, but she was smiling, clearly enjoying every second of this. “Angela’s right, sweetie, no need to be embarrassed” Cathy said “I will be proud to walk to the car with you.”

Peter swallowed hard, evaluated his position:  I am supposed to be a maid, Angela is calling Cathy my Mistress. He smiled “I am sorry if I sounded ungrateful Angela, the day is a little overwhelming.”

Walking to the car a part of him was starting to enjoy a part of what was happening:

The control part not the uniform part. 

Not the public display part. 

Wearing a dress outdoors for the first time the cool air on his legs came as a surprise as did the swish of uniform against stockinged legs.

The car may have been only a few dozen steps away but in Peter’s head it was a few dozen miles. “Let’s go home,” she said softly. “You have work waiting.”

“Thank you for buying me more appropriate cleaning clothes Mistress.” Peter attempted to regain some control by M-wording Cathy.

Cathy bleeped the car open, if the wind changed her smirk might become a permanent feature. 

Peter’s heart kept up a fast thump, thump as they drove. “Why did Angela say that Mistress?”

“Angela said a lot of things.”

“That I am a sissy maid.” Peter watched Cathy “why would Angela call me that?” 

Cathy smiled, said she had explained to Angela what she wanted. “Angela went much further that I had imagined, I never suggested she call you a sissy maid to your face Peter.”

“You didn’t correct her when she did, I’m supposed to be a cleaner. That’s what we agreed.”

“You didn’t correct her either Peter, and that curtsey to me says, for now, a maid is exactly what you are.” Peter kept his eyes on his knees, if he didn’t look out the car windows then he wouldn’t have to see his reflection. They drove in silence for a while. 

“I am confused Peter, one minute you are rebelling, and shouting at me.” Cathy said “the next you are acting subservient and calling me mistress. What’s it to be Peter? Do you ‘want’ to be my maid today or do you want to go home?” She had stopped at the side of the road opposite his apartment building. Cathy smirked as he realised where they were. “Decision time Peter.”

“What is wrong with you? Drive!” Cathy killed the engine. “Julie could come out at any moment…just drive.”

“Decision?”

“Please drive away Mistress, I’ll be your maid today.” 

Cathy started the car “and after?”

“Now you have video I guess you will always be my Mistress.”

“I made the video is for my eyes only Peter” Cathy explained she missed him between visits and accusing her of blackmail both shocked and hurt. Cathy theatrically dabbed at her eyes with a tissue as she pulled away from the kerb. 

Pulling into her driveway, Cathy told Peter let himself in, have lunch then start on the list of chores she had left for him. He noted how she had called the back door ‘the maids entrance’ 

In the tight corset he doubted he could eat even if nerves allowed, he quickly changed from sneakers into the ballet pumps that were waiting by the back door, made a pot of tea. Drinking it while cleaning the kitchen he moved on to the hallway, starting from the cobwebs he worked downward until he was on his hands and knees polishing the wooden floor. As Peter finished he heard the sound of Cathy’s car pulling into the driveway. Attempting to play the part she wanted, he hurried to greet her. 

Curtsey “Hello, Mistress” the cheerful edge to his voice masking anxiety. 

Cathy’s surprise at having the door opened to her melted into a smile “hello Peter,” she said “the curtsey is a nice touch, please keep it up.”

Curtsey, “Mistress”

Cathy’s eyes sparkled, she said ballet pumps spoiled the uniform. “I bought you more suitable shoes,” she said, her tone teasing and took a 3-inch lilac heeled shoe from the shopping bag “heels are the correct footwear for your uniform,” she smiled. “My sissy maid wearing heels is a clear sign of his submission.”

Peter eyed the heels nervously. “They look... scary tall.”

Cathy chuckled, put the shoe back in the bag. “You’ll manage. First, I need to address something. Someone rang the doorbell while I was shopping. What’s the problem with answering it?” Cathy raised an eyebrow, observing Peter’s nervous demeanour.”

“I look like a man in a dress” Peter’s face flushed.

“Why are you telling me this?” 

Her teasing gave him confidence to continue playing the part of a maid, “I wonder if you could help me look more maid like if I am to open the door...”

Cathy’s eyes sparkled with a playful glint, she tilted her head, feigning confusion. “You want to look more maid like? And just how would you like me to do that?”

Peter swallowed hard, his voice barely above a whisper. “Is it possible to make me look less like a man-maid with some makeup?”

Cathy’s smile widened as she heard his request. “Well, I suppose I could. But there’s a little condition.”

Peter’s heart sank slightly. “Condition?”

“Yes,” Cathy said, her tone teasing. “Before I help you pass as a maid, you need to promise to answer the door to anyone except Julie. I don’t want her seeing you like this, just yet.”

Peter hesitated, he knew Cathy was mostly teasing but it still frightened him. “Thank you.”

“Take this bag to the maids room”

“Where is that Mistress?”

Cathy threw a wide smile “of course, you haven’t seen it yet, follow me” she led him through the kitchen and along the passageway toward the back door., 

“Tada!”she exclaimed unlocking and throwing open the door to the storage room. Cathy could hardly contain herself as she watched his reaction. Since he had last seen the room contractors had transformed  the junk room into Cathy’s idea of what a maids room should be.  She watched as Cecilia took everything in: 

New single bed, bedside, alarm clock, reading lamp. Opposite the full height mirror fitted to one wall was a sturdy hook that, as Cathy explained would make lacing his corset easy. Cecilia’s eyes opened even wider when Cathy opened the closet “somewhere to keep your ‘Peter’ clothes and spare uniforms, underwear can go in the dresser.”

Opening the door at the far end of the maids room revealed a small shower room complete with a fully stocked vanity. Peter felt overwhelmed, Cathy had spent a lot of money on the ‘maids room’ maid uniforms and corset - as if she intended this not to be a one weekend event.

Cathy motioned for Peter to sit at the vanity and set to work. She began with his short hair using gel to create a spiky look gave the impression of a pixie cut. Next came daytime makeup, carefully contouring and blending to achieve a look Cathy considered to be that of either a very feminine man - or a slightly butch woman. She examined Peter with a critical eye. “Satisfied?” she asked. “Just think of how shocked Julie would be if I told her how you manipulated me into feminizing you.” She paused, as if pondering complicated math problem. “Now we have come this far calling you Peter now seems a little ridiculous. I will call you Cecilia.”

Peter swallowed hard, his face a deep shade of red.

“Back to work Cecilia,” Cathy said, her tone leaving no room for argument. “Listen for the door; I’m expecting the courier to return…wait Cecila, we nearly forgot your heels.”

Peter gingerly slid his foot into one. Despite fitting the shoe was unsurprisingly uncomfortable. He wobbled slightly as he tried to find his balance while putting the second shoe on. Cathy wore a supportive smile and offered a steadying hand.

“First things first,” Cathy instructed, “stand up straight, shoulders back, chest out, stomach in. You need to walk with confidence, even if you don’t feel it.” She demonstrated a few steps across the maids room, her movements graceful and steady. Peter followed her instruction, taking small, cautious steps, He wobbled using her hand to steady himself, Cathy watched him with an amused expression. “Good start,” she said. “Now, practice bending. When you need to pick something up, bend from the waist, keep your legs straight like a rod. Never bend at the knees. Men like that.”

Peter paused, his eyes widening as he processed her words. He straightened up and gave a nervous curtsey. "Time out, please, Mistress," he stammered. “Men? Is someone coming?”

Cathy basked in his anxiety, her smile growing a little wider. She could sense his nerves, and she was going to make the most of it. “Oh, don’t worry, Cecilia,” she said in a sweet, teasing tone. “If a guest happens to call unexpectedly you will not be recognised. Feminised as you are now they will accept you as my maid.”

Peter’s heart raced at the thought, the image of Jim seeing him like this making his stomach churn. “What if Jim sees me, tells Julie about my uniform?”

Cathy, enjoyed his obvious discomfort while saying ‘my uniform’  “Relax, if you are a good maid Jim will not come here, I just want you to be prepared for anything.”

“Mistress” Peter curtseyed before resuming practicing bending to pick up an imaginary object. Next he tackled the stairs with Cathy’s guidance. After some time, Cathy refined his curtsey to her specification. “A proper curtsey involves moving one foot back, bending your knee slightly and lowering your body while keeping your back straight. It’s an important part of your role.”

By early evening his wobble had all but disappeared. Mindful of every move he served Cathy a pot of tea, asked if Julie would be coming to take him home soon. Cathy said he could listen silently while she telephoned Julie to finalise and put her iPhone on speaker:

Cathy: where are you?

Julie: Still traveling home, I’ve been at the beach all day. Where are you?

Cathy: Home, finally, after shopping.

Julie: Buy anything interesting?

Cathy: Clothes for Peter.

Julie:  Enough said, I do not want to know.

Cathy: We hardly got any work done, can I keep him tonight?

Julie:  Sure, I’ll fall asleep the second I sit down. 

Cathy: Okay, we can get an early start.

Julie: That much still to do?

Cathy: I doubt we will even get halfway.

Julie: That a hint? If you want something just ask Cathy.

Cathy: Okay, can I have Peter next weekend?

Julie: Sure, make arrangements with him.

***

Inside Peter seethed, considered his next move; Cathy clearly wasn’t satisfied humiliating him for one weekend, she spoke of pleasing men, how to behave and look to attract their attention. Peter’s mind reeled. He failed to understand how a simple desire to wear a dress had escalated into this. He felt as if he were careening toward being a maid on Cathys whim - something he did not want. He would make his feelings clear at the first opportunity.

While inspecting his work Cathy said how lucky it was he would get the chance to spend the next weekend at her house. Peter said “today was a one off, I refuse to be your maid again.”

“I am sorry you decided that” Cathy raised an eyebrow and leaned back in her chair, her tone playful. “But that is okay, you don’t have to wear uniform again. And you don’t have to come next weekend. We can go back to one day a week.”

Peter blinked, caught off guard by her sudden willingness to let him off the hook. “What, you are okay with that?"

“Sure, do you feel the same way about your corset Cecilia?

Peter said if she had asked a few hours ago he would have said never again.  “Now I have gotten used to the corset I could get to like it enough to wear it for you.”

“In time you might have felt the same about your uniform.” Cathy paused as if an idea had suddenly taken over her mind “would you wear the black uniform for me, just for tonight? I’ll understand if you say no.”

“Why not, I mean the entire day has been demeaning and humiliating.” Peter chuckled.

“And you want me to think not even a little bit of you did not like that?” Cathy smiled, said when Angela telephoned for an update she claimed the exact opposite, “Angela said you seemed to enjoy her putting you into a maid uniform.” 

 

*** 

Cathy showered, the hot water wash away the excitement of the day. She dried herself off leisurely, enjoying the thought of her evening out, and selected a sleek, smart dress for the night, the one that hugged her curves and made her feel elegant but while looking effortless. After styling her hair and applying a touch of makeup, she glanced in the mirror, satisfied with her look. Slipping into heels, she headed downstairs, where Peter was mock-busying himself.

Cathy complimented Cecilia, said the black uniform looked very smart. She settled onto the sofa, picked up a magazine and began flipping through its pages absentmindedly. The doorbell rang, and she didn’t even glance up. "Cecilia, get the door," she called casually.

Cecilia hurried to the door bracing himself, when he put his eye to the door viewer his heart skipped a beat - Angela! A smug grin spread as he opened the door.

“Cat got your tongue Cecilia?” she asked, a teasing edge in her voice. "Cathy is expecting me."

Peter felt the heat rise to his face as he scrambled to remember his lessons. He stepped back awkwardly and gave a small curtsey. “Sorry, Angela...”

Angela’s eyes flashed with amusement as she cut him off. “That’s no way to speak to me Cecilia, please address me properly. To you I am Miss Angela.”

“Sorry, Miss Angela,” Peter corrected himself and curtseyed.

Angela stepped inside and looked him up and down with a smirk. “I think you are a natural, what do you say to that…” she teased, but before Peter could respond, Cathy appeared.

“Stop teasing my maid, Angela,” Cathy said with a light chuckle and explained that Cecilia would not be wearing the uniform again. “Tell Angela why Cecilia.”

Cecilia repeated what he had told Cathy, Angela looked surprised “really Cathy? You are okay with that?” 

“The taxi is outside. We’re going to be late.” Angela smirked, looking from Cathy to Peter. “Is Cecilia coming to the restaurant with us? Some customers bring their own wine - we could bring our own maid.”

Cathy shook her head with a grin. “No, he can feed himself and wait up, I want my maid to open the door once before he is gone forever. ”

With that, the two women left for their dinner, leaving Peter standing awkwardly in the hallway, his cheeks burning as he thought over Angela’s taunts.

At the restaurant, Cathy and Angela sipped their wine, the evening air filled with laughter and conversation. Angela leaned in with a conspiratorial smile. “So, it seems your search for a sissy maid is back to square one”

Cathy laughed, swirling her glass. “Cecilia is rebelling at the moment. I’m not beat just yet Angela.”

“I did warn you after Jim” Angela looked serious, said that was to be expected “I mean he is not even a proper crossdresser and you plunged him into a maid uniform without warning.” 

“He has been so servile from day one, I thought he would love the uniform.”

Angela raised an eyebrow. “Everyone says online a trainee Mistress should start with a committed crossdresser as a minimum, preferably a sissy.”

Cathy said she had not given up hope, “he admitted to liking the corset.”

Julie sipped her wine “ooh, tell me about the corset shop again and don’t skip a single detail this time.”

Cathy smirked as she re-began.

Angela laughed. “We should’ve eaten in. Could’ve had Cecilia serve us.”

Cathy smiled but shook her head. “No, he’s had enough for one day.”

The night air felt cool, almost cold, as she neared the front door. Before she could ring the bell Cecilia opened the door, stepped back and curtseyed. “Good evening, Mistress,” he said softly.

Cathy, a little unsteady on her feet, stumbled slightly, her heels clicking on the floor. “I might have had one too many drinks,” she slurred with a playful grin. “Help me to my bedroom Cecilia.”

Peter took her arm, guiding her through the house and carefully up the stairs. As they entered her bedroom, Cathy tossed her purse on the chair, her eyes full of mischief. “Zipper Cecilia.”

Without hesitation, Peter stepped forward, gently unzipping the back of her dress. Before he could move away, Cathy turned toward him, shrugging the dress off her shoulders and let it fall to the floor, revealing that she was naked underneath. Peter quickly looked away. She climbed into bed, “I’ll be thinking of my maid before I go to sleep,” she said laughing, pulling the duvet up around her. He hung her dress, looked back as he reached the doorway only to see her slip an arm under the covers, she giggled “what are you doing to your mistress Celia…you naughty maid.”

Peter closed the door behind him and headed to his room as fast as heels permitted. He had been shocked when she casually undressed in front of him, and even more shocked by her display of self-indulgence beneath the covers.

If not for the chastity belt Julie had locked him into, Peter knew he would have indulged his own urges in the privacy of the maid's room.

Next morning, Peter woke early, eager to avoid any awkward confrontations. He showered, decided to meet Cathy half-way and laced himself into his corset and put on his summer dress. He thought through recent events, in the safety of hindsight the humiliation seemed not so… well not so humiliating.

Meanwhile Julie replayed the day at the beach as she waited for sleep, it had been her first leisure day without Peter in an age. Suddenly missing him she wondered where Peter was sleeping. Her body jumped at that feeling of falling that sometimes comes between wake and sleep, she sat up, suddenly wide awake. 

For the first time since they started dating, she found herself wondering what if every day was like that - without Peter. Julie stretched out in the half empty bed and felt ashamed by how okay she felt about that. 

“Good morning Cecilia” Cathy forgot her hangover at the sight of Cecilia, he had made an attempt, a beginners attempt, at recreating makeup look Cathy had done. Somehow she managed to hide her delight.

“Good morning, Cathy.”

Cathy sipped her coffee, a mischievous glint in her eyes. “Tell me, did I say anything risqué last night?”

Cecilia hesitated. “No.”

Cathy let out a sigh of relief, pretending to wipe her brow. “Thank goodness. In that case I had the strangest dream.”

Peter awkwardly excused himself by outlining a list of cleaning tasks. As he went about his Sunday duties, simple tidying and dusting, his daydreams surprised him - part of him wondered if he should go back on his decision.

By lunchtime, Cathy had mostly recovered from her hangover. 

Her mood mischievous. 

Her mind calculating. 

She walked into the kitchen, instructed Cecilia to prepare a salad for two and, leaning against the counter,  watched as he prepared the food.

As he set the informal table in the lounge room, Cathy continued her surveillance, eyes following his every action. She dropped a magazine twice, each time instructing Cecilia to bend from the waist and pick it up.

“Cecilia, I’ve a male lunch guest,” she said, a slow smirk forming on her lips. “You know him and so does Julie.”

Peter’s heart sank. The colour drained from his face as the implications of her words hit him. “Cathy, please… I…can we time out?” he begged, his voice shaky.

Cathy waved a hand dismissively. “No time outs, Cecilia. You’ll set the table and prepare the meal as instructed.”

Peter felt close to tears, panic creeping into his chest.

He knew Cathy would expose him to Jim. 

He knew Jim would ridicule him forever more. 

Cecilias eyes welled up, in his imagination Cathy would encourage Jim, drop her fork, take pleasure from his humiliation. 

Just when Peter looked as if he might burst into tears Cathy stood up and crossed the room, placing a hand gently on his shoulder. “Cheer up, Cecilia,” she said, her voice softening. “You are my lunch guest.” Her smirk faded into a genuine smile. “Just you and me. Let’s sit and enjoy our lunch.”

Relieved, Peter fetched a bottle of wine and sat across from Cathy at the small, intimate, table. As they ate, she talked warmly about the weekend. Cathy proudly retelling events in a way that cast Cecilia as a brave hero who had owned every experience  thrown at him the previous day. She studied him closely, her eyes gleaming with curiosity. “I’m sad I will not see Maid Cecilia again, but I want to thank you for humouring me and making my weekend unforgettable.”

“And I want to thank you for accepting my decision Cathy,” he replied. He was not about to back down, or admit to second thoughts.

Cathy raised an eyebrow, her lips curving into a smile. “You know what puzzles me, Cecilia? I never asked you to wear your corset and bra today. Yet, here we are.” She gestured with a wave of her hand, letting the silence draw out as she watched him shift uneasily under her gaze.

Cathy drove Peter home, the hum of the engine the only sound. Peter stared out the window, his mind swirling with conflicting thoughts, memories of the past two days replaying like scenes from a dream he couldn’t quite shake.

When they finally pulled up outside the apartment building Cathy turned to him, her expression unreadable. “Before you go…” She paused, the moment stretching between them, her voice soft but firm. “I am angered by your selfishness Cecilia, everything is not about you. If you want to come to my home again you will need to ask. And, if I agree, it will be on my terms.”

***

Peter was relieved Julie didn’t mention his weekend straight off. Instead, she asked if he'd eaten and talked about her Saturday the beach. He encouraged Julie to talk about her weekend while making a pot of tea.

One evening, while alone, Peter pulled his old, battered MacBook out of his briefcase. Cathy had written the password of her home network on the underside of the router, sometimes she would speak the password as she typed at her iPad. As guilty as he felt Peter stuck with it and soon learnt the visit to corset and uniform shops had been methodically planned. Cathy was active in a mistress chat group. He wiped his digital feet before logging out, not even a shadow of his snoopery remained. 

Soon remorse at being so selfish began setting in. He could have asked more questions. He could have been a better… better what? 

Better crossdresser? 

Better maid?  “No” Peter said aloud making himself jump. 

Better friend - that is what he should have been!

Cathy had used up days of her leave for him.

Cathy had spent a lot of money. 

A part of Peter regretted acting so selfishly.

A part of Peter regretted not giving maid play a fair chance - it is only a type of dress after all. But, he reasoned, Cathy had been so definite, there probably was no take-backs.

***

When Julie mentioned the following weekend Peter said “I’m not going back,” explained they had a disagreement, “and if I want to go she said I have to ask her permission first.”

Julie loved gossip especially when it involved boyfriend and best friend. “What was the argument about?” 

“Something and nothing, Cathy bought me a dress and I do not like it,” Peter played it down, he knew Julie would get Cathy’s side of the story.

Seemingly disinterested, Julie shrugged, said Peter had a crossdressers tiff. “Or are you done with that?”

“I really think if I could do it here…”

Julie cut him off. “No, not here! Never here Peter, we agreed that.”

Cathy invited Julie to stop by her house after work. Julie looked around in awe as they made their way to the lounge room. The house was spotless—no dishes in the sink, counters gleaming, and everything in place. Julie could hardly believe it. She'd never seen Cathy’s home so organised.

Cathy poured them both a glass of wine. “So, are you impressed?” Cathy said, swirling her glass, "Peter did quite a number last weekend.” 

“Like something out of a magazine spread,” Julie said “Peter said you two had a disagreement over a dress, from what he said I don’t think he is coming back anytime soon.”

Cathy shrugged, nonchalance better than inviting questions “fine by me, I mean his cleaning is second to none but he was being ungrateful.” She topped off their glasses “anyway, I’m motivated to keep the house like this now.” Julie asked if upstairs was just as sparkly. “The spiders seem happy enough in the spare bedrooms and bathrooms.”

Julie felt slightly buzzed from the wine she’d shared with Cathy. Peter was sat on the couch, she tossed her bag onto a chair and smiled at him. "You did a great job at Cathy’s," she said, surprising him with the compliment. “it is like a different house."

Peter’s face brightened as he basked in praise. "Thanks. I barely scratched the surface, though. There are so many rooms in that house Julie."

Julie opened the fridge, poured herself a glass of wine, her tone growing more casual. “Peter, when I thought you were staying at Cathys this coming weekend I arranged to visit my parents, you want to come with? As she expected he declined, Peter and Julie’s parents struggled to get along even before she told her mum about the dress wearing.

Peter shrugged, “I can read perhaps a few beers with mates.” He laughed “I mean wearing a tee and sweats reading.”

“You and Cathy still not speaking?”

Peter shrugged “I’m not backing down.”

Julie offered a voice of reason, saying how happy they both seemed with the arrangement while hiding how she felt inside.

 “Cathy can be a little short tempered at times. I find if I leave her for a day or two the next time we meet she behaves as if nothing happened. Hey, do you still have the key?” Julie suggested he go there after work Friday “that gives you time to be settled in before she gets home. My suggestion is; let her think she has won and act as if nothing happened.” 

“I am so lucky to have a girlfriend who is so understanding.”

Julie said tolerant would be a better word to describe how she felt, “below the surface I’m like a duck paddling against the current. Anyway…” Julie emptied her glass “what is so awful about the dress…NOOO…don’t tell me, don’t say a word.” They both laughed. 

Recently the central character in Julie’s dreams was Peter wearing a dress. 

Not always the same dress. 

Not always the same scenario. 

Not always, but often, the dream included a scene where Julie came home and discovered Peter crossdressed. And - worst of all - it was that scene that played behind her eyelids when they ‘made love’ as Julie called it.  

9 - The Second Weekend 

Julie mentioned she was skipping the Friday after work drink, instead she would visit her parents straight from work.

The Uber pulled into the drive, Cathy panicked, there were lights on in the house, she was certain she had not left the house that way. She shut the Uber door loudly, spoke loudly and held a one sided conversation as she neared her door, loud enough for burglars to hear her coming. As she went to insert her key the door opened.

“Good evening Mistress” Cecilia, wearing his black formal uniform, curtseyed.

“Cecilia! …you gave me a fright” Cathy hugged Cecilia, she could feel tears welling up inside her, knew they would streak her makeup but did not care “I’ve missed you.”

“I am sorry I misbehaved and acted ungratefully Mistress.” He said into her neck. 

Cathy turned to close the door hiding her face, “go to your room, we can talk tomorrow.”

Saturday, waking to the alarm clock, Cecilia felt the familiarity of submission settle over him as he corseted and brassiered himself, he put on his lilac uniform and slipped stockinged feet into lilac high heels. He applied the liquid lilac lipstick, embarrassingly purchased during the week, to his lips and turned his attention to a container of hair gel. Judging his appearance to be best achievable he brewed coffee, set a tray and headed upstairs, hearing movement he lightly taped on the door.

“Come in.” Cathy answered, unable to contain her look of delight. 

“Good morning Mistress.” Cecilia curtseyed as he set the tray down and poured her coffee. 

“I love your lipstick colour, is it new?” Cathy smiled kindly “and I like this new development Cecilia, coffee served in my room,  I trust it will be a regular part of your duties.” He remained silent and curtseyed. Sufficiently awake Cathy teased, gesturing toward the uniform and asking why the change of heart. 

“I assumed ‘your terms’ would include maid uniform and humiliation Mistress.”

“And you accept that?”

“I want us both to enjoy my visits…”

“Okay,” Cathy accepted that as his agreement, too late she realised a better, experienced, mistress would have been more forceful in demanding submission, she added “I think you NEED humiliation.” He stared at the floor while remaining silent. “Go on Cecilia, say it!”

“I came here because I need to be humiliated Mistress.” Curtsey.

He worked methodically finishing each chore; washing, sweeping, polishing, dusting. Each one felt more comforting than the one before as if, by wearing the uniform, he was becoming Maid Cecilia.

From time to time Cathy watched from a distance, her satisfaction growing with each passing moment. The sight of her maid cleaning her home, obedient and quiet, brought a deep sense of control that she relished. She leaned back, sipping her tea, thinking of the possibilities that lay ahead. This was only the beginning.

Cathy summoned Cecilia to the drawing room. “Cecilia, change into your formal uniform then take some time off to relax, make yourself some tea, and listen for the back door.”

Millie arrived at the ‘servants’ entry of Cathy’s house, she was around the same age, perhaps a year younger than Cecilia and wore the same traditional maid uniform; black dress, crisp white half apron, black heels. She wore her auburn hair pinned up neatly into a bun beneath a lace cap.

“Cecilia? I'm Millie," the maid said, smiling briefly. “Mrs Green sent me to collect you.”

Confused but dutiful, Cecilia invited her into the kitchen and returned to Cathy. "Mistress, Millie is at the door.”

She glanced at Cecilia and chuckled., Cathy explained the people in the big house were holding a cocktail party, they were short-staffed, “I volunteered my maid.”

“I am not ready for people to see me Mistress.”

“Did Millie look surprised and stare or accept you for what you are?”

“As a maid Mistress.”

“Then so will everyone tonight.” Cathy smiled “Thus, you are indeed ready. Now go with Millie and I will see you later.”

Cecilia returned to where Millie waited, careful to keep his voice soft and feminine. “Okay Millie, I’m ready. Mrs. Green’s cocktail party, right?”

“That’s right,” Millie replied as they started walking side by side. “I’ll be showing you the ropes today, but, from what I hear, it sounds like Miss Cathy is quite impressed with you already. She was telling Mrs. Green earlier today how excited she is to have you on board.”

Cecilia felt his heart skip a beat. Even third hand Cathy’s praise filled him with pride. While he felt confident in the role of Peter-in-a-dress / Cecilia indoors, he felt nervous of interacting with others for such a long time, people would be watching his every move.

They set off toward the village, with heels tapping rhythmically, and in time, against the paving. Cecilia held his chin tucked slightly to conceal his Adams apple just as Cathy liked. Millie, on the other hand, walked with  easy confidence, her experience as a maid clearly showing.

As they approached the village centre, they no longer had the street to themselves - people shopping, people sitting outside the coffee house chatting over lattes - that sort of thing. A few heads turned as the two maids walked past, their identical uniforms and neat appearances drawing more than a little attention. Cecilia could feel the eyes on her, the curious gazes following their every move.

“Don’t worry,” Millie whispered softly, sensing Cecilia’s unease. “It’s only natural they’d check us out. After all, people have been talking about Cathy’s new maid. They want to see what all the fuss is about.”

Cecilia nodded, her cheeks flushed slightly - being out in public, walking side by side with a seasoned maid like Millie, who seemed so at ease in her uniform made Cecilia feel exposed and accepted in equal measures.

Cecilia gave a small, polite smile, grateful for Millie’s reassurances but still feeling a knot of nerves in his stomach. As they passed the coffee shop, a few of the patrons leaned forward in their seats, clearly intrigued by the sight of Cathy’s new maid. Millie greeted them with a respectful nod, and Cecilia mimicked her gesture, feeling his heartbeat quicken.

When they finally arrived at Mrs. Green’s house they immediately set to work, ensuring everything was in order. The grandeur of the Green’s house was on full display; polished silver trays, crystal glasses, and carefully arranged hors d’oeuvres adorned tables. Cecilia moved with care, taking his lead from Millie and eager to perform his duties without a hitch.

As the guests trickled in, Cecilia found himself slipping into role, earlier nervousness ousted by business as he focused on serving. It wasn’t until Cathy arrived, radiant in a sleek evening dress, that Cecilia felt a nervousness thing overtake him. 

Cathy stood across the room in conversation with a small group. It was then that Cecilia made her way over, balancing a tray of drinks.

Cecilia approached Cathy, hands steady but heart pounding. He caught Cathy’s eye, and without thinking - without pausing to consider the room full of people watching - Cecilia dipped into a curtsey. “Mistress,” he said softly, offering Cathy the tray of drinks.

For a moment the groups chatter paused. A couple of  people exchanged glances, clearly taken aback by Cecilia’s curtsey and the use of the word Mistress as if he had time travelled from the 1920s’

Cathy, however, didn’t miss a beat. She smiled warmly, accepting the drink as if nothing were out of the ordinary. “Thank you, Cecilia,” she said smoothly, casting a quick, knowing glance at her audience. “I’m pleased to see you haven’t let your standards slip just because we’re not at home.”

The tension in the air seemed to ease as Cathy spoke, and a few of the guests chuckled, nodding in agreement. One of them, an older woman, even commented, “It’s refreshing to see such dedication to service.”

Gerald chuckled, "The most respectful thing our cleaner says is 'cup of tea, mate?'"

Cathy smiled, clearly enjoying herself. "Cecilia is not a cleaner Gerald, she is my maid. Cecilia is aware her conduct is a reflection on me." She turned back to Cecilia "please continue, Cecilia."

Cecilia moved on, continuing serving drinks. The evening wore on and Cathy, slightly unsteady on her feet, as much from her skyscraper heels as alcohol, beckoned him over again. "Cecilia."

Cecilia approached, curtseyed, "Mistress?" 

Cathy, her eyes gleaming mischievously, dropped her clutch purse. "Pick that up.” 

Cecilia froze for a moment and quickly bent at the knees, lowering himself to retrieve the purse while retaining modesty.

Cathy dropped the purse again, her smile widening. "No, Cecilia. We will repeat this exercise until you pick it up properly.

Cecilia’s heart sank as the game became clear. There was no choice now. To disobey would only serve to daw more attention. Slowly, he bent from the waist, imagined his uniform would probably expose his stocking tops to the room. "Much better," she purred, her voice dripping with satisfaction.

When a taxi arrived to take Cathy home Dominic, one of the guests, said he was staying over, offered to return Cecilia home the following day. 

Cathy smiled, “what is that saying Dominic… keep your friends close and keep your maid closer. Cecilia is coming home with me tonight."

Cecilia’s heart still raced from the public display of control exerted over him as he followed Cathy to the waiting taxi.

10 - Returning Home

Julie sighed, scanned the coffee shop for earwigers “…Mum called him a pervert.”

"You told your parents!” Cathy was genuinely shocked.

"Only mum, if Dad knew about Pervy-Pete I would be locked in my child-bedroom.’"

Cathy gave her a ‘really?’ smile. "He’s not a pervert, Julie."

“I’m struggling Cathy, I know how okay you are with this. But let me assure you having a crossdressing boyfriend is hard, I close my eyes and all I see is him mincing around in a flowing gown…or worse.”

Rather than stepping on Julies’ ‘worse’ landmine Cathy waited for Julie to expand on what might be worse, Julie fidgeted with her coffee cup before speaking again. “Mum asked if me and Peter are splitting. They’re pushing for grandkids, and they think Peter isn’t… well - you know.” She waved her hand in the air, avoiding finishing the sentence.

Cathy’s eyes widened slightly as the admission sank in. “How do you feel about that?” she asked softly.

Julie’s lip trembled, and she took a shaky breath. “I don’t know, Cathy. Some days, I think it’s inevitable. Other days, I cry because I don’t want to loose him. And I feel guilty for thinking about us separating, but then I think about Cecilia… I just don’t know how much more I can take.”

Cathy froze, coffee cup hovering mid-air. Hearing Julie refer to Peter as Cecilia sent a wave of shock through her. How much did Julie know?

“You didn’t think I'd find out?” Julie glanced up, pleased by Cathy’s wide-eyed stare of alarm. “You never think about the trail, do you? Person 1 knows Person 2, Person 2 knows Person 3, and so on and with such red hot gossip… my coworker friend has a maid… it didn’t take long for that gossip to reach Person Julie.”

Cathy’s face flushed with embarrassment as she realised just how careless she had been. “Julie, I never meant for…”

“Oh, I’m sure you didn’t, but here we are. ” Julie interrupted, her voice laced with sarcasm. “You created ‘Cecilia’ and paraded him around as your personal maid at some fancy party. How, exactly, does that sound like it wasn’t planned?”

Cathy took a deep breath, trying to compose herself. Her heart was racing, but she knew she couldn’t hide the truth any longer. “It started as a game, I read how some crossdressers like to be subservient, and what better way to indulge that than with a maid scenario? But the instant I saw him in uniform it became more than that. He went along with what I wanted and in that instant, like one hit of heroin, I was addicted.”

Julie nodded slowly “just you?”

“Perhaps we became addicted.”

“That fits.”

“I’ll end it with Peter right now, Julie, it’s over and I am truly sorry for what I did.” Cathy looked down, voice barely above a whisper, she plucked up the courage to voice her deepest fear, the tears she’d been holding back finally escaped “…if it’s not already too late I don’t want to lose you as a friend.”

“We are nowhere near un-friending, Cathy.” Julie’s smile was bittersweet. “This is not social media. Look, as far as I am concerned, it’s better this is happening now, before Peter and I started a family.” She paused. “I’ve been thinking about it a lot. If it hadn’t been you indulging his crossdressing it would have been some stranger. Mum and the internet agree on that point - it would have happened with or without you. And I agree as well.”

Cathy’s heart sank, guilt twisting inside her. “I never wanted to come between you two…”

Julie shook her head. “You did not Cathy. Cecilia must be something Peter’s always had in him, at least I know Peter is safe with you.”

***

On the spur of the moment Julie picked up her iPhone, called human resources, booked a holiday for the following week then called Peter at work, told him to do the same. “Okay, sorted" she said after ending the call, her voice soft with resignation as she told Cathy she was spending her week at her parents to ‘think things through’ 

“And Peter is taking a week off why?”

“For the same reason. Peter can stay home or you can have Cecilia at your place.”

They sat in silence for a moment, the weight of the conversation settling between them like a thick fog. Finally, Cathy spoke, her voice hesitant. “Peter is always welcome. I’ll leave the decision with you.”

Julie was relaxing with a glass of wine when Peter arrived home from work that evening. He seemed nervous, sensing the tension in the air. “You’re quiet tonight,” he said cautiously, setting down his bag and asking what surprise Julie had planned for their holiday week. Julie gave him a tight smile, outlined her thoughts. Peter seemed unsurprised as Julie told him about spending her holiday at her parents. 

As easily as Google maps deciding on the route to someplace, they reached a mutual agreement on the route to end-of-relationship. And, not needing a week to ‘think things over’ agreed there was no reason to put the decision off. 

Julie would spend her week as planned, Peter said he would ask Cathy to stay at hers for the week. He heard the sarcasm in Julies voice when she said “Cathy will jump through hoops for her Cecilia.” 

11 - The First Week

Julie handed over the keys as if she were presenting Cathy with the keys to a small kingdom in the Pacific Ocean rather than the keys to her ex-boyfriend. 

Cathy skipped the bar after work, she had plans for the night. Excitement built during the drive home, she planned her moves step by step - as carefully as Siri planned a route turn by turn. 

Cecilia opened the door before she was halfway from the car, Cathy greeted him warmly, told him to go the maids room, shower, denude his body of hair, moisturise, apply makeup, gel his hair, put on a bathrobe and wait for her. 

After taking a long, calming, shower, Cathy dressed how she imagined a dominatrix would; slutty makeup, her ‘just in case’ first date black undies, seamed sheer stockings, white blouse, knee length pencil skirt, and fuck-me heels. 

This was new! Cecilia felt nervous excitement coursing through him when Cathy walked into his room. She looked going-out ready, and he had been told to pamper himself. 

Most likely possibilities: Worst case she would make him wear some humiliating outfit, best case she would dress him similar to her and take him for a meal and humiliate him to the waiter. 

He hoped for the second scenario.

Cathy told him to loose the bathrobe as she circled, casually eyeing him head to toe, she smiled “I wonder what Julie would say if she saw us now. I mean now there is no longer any reason Julie cannot meet Cecilia.”

“Please, not meeting Julie, Mistress” Cecilia begged, feelings ramped up from nervous to scared.

“I’m getting ahead of myself” Cathy sniggered, asked how long he had been in chastity and looked surprised when he said it had been fifteen days. She handed him a key “let me see what Julie has dumped on me. Go on Cecilia, set the beast free.” Cecilia’s hand shook a little as he held key to lock. “Don’t be ashamed Sissy, my beast comment was a joke, I mean a beast would not fit in a tiny little tube like that.”

Cathy, impatiently took the key and unlocked him, “that is even more disappointing than I imagined, I expected your little cock to spring to attention. Never mind, let me watch my sissy maid corset and brassiere himself.”

Experience had taught Cecilia to roll his stockings up his legs before corseting himself. Cathy watched in silence as he fastened the metal busk of his corset then hooked the laces over the corset hook. He leant forward slightly and began working his way along the laces - top to waist, bottom to waist, scoop chest fat, top to waist, bottom to waist, and so on. Cathy saw he had the laces almost fully closed before tying off the laces. 

Not wanting to give Cathy cause to reprimand him he checked the seams and fastened his stockings to the suspenders, then re-checked seams in the mirror. He mimicked Julie putting on her bra and leant forward to situate his manboobs in the cups before fastening the back. Cathy barely controlled her laugh as he scooped wayward chest fat into the cup size bigger padded bra. 

Cathy noticed for the first time that Cecilia’s small yet convincingly enhanced bust and slim corseted hips created a look of mid-puberty.

He checked the mirror, to his dismay nerves continued to block an erection, and worse still a string of pre-cum now hung from his flaccid cock. 

“My poor little sissy.” Cathy spoke as if talking to a child who had fallen and scraped a knee “…Julie has had you locked away so long you are leaking. Well, you will be pleased to know, I am not like that.” Cathy turned Cecilia to face the mirror “Do you like what you see?” Cecilia nodded “don’t be shy, show me how much you like the way you feminised yourself for me.” She guided his forearm “don’t be shy, stroke your little sissy cock for Mistress.” As if her words acted as a remote control Cecilia began hardening, two weeks of chastity combined with Cathys humiliation sped his transformation from flaccid to hard. 

“You either do as you are told this second or it’s back in chastity.” Cathys voice contained a hint of anger. Cecilia obeyed, he began to stroke slowly, loosely. A wanking sissy-maid only had one chance to make a first impression and the last thing Cecilia wanted to demonstrate was hair-trigger. 

Cathy watched in silence as he began to harden. It was no sissy cock like they talked of on-line, with each stroke it grew and grew. His soft moan acted as early warning for Cathy’s controlling encouragement “that’s it Cecilia, cum for your Mistress.” Strings of cum hit the mirror.

Cathy stood slightly behind and to one side, they watched as the cum slowly made its way down the mirror like racing raindrops on a windowpane. “Do you like the taste of cum?” 

Cecilia looked shocked “I have never tasted it and never will!” 

“Go ahead, taste it Cecilia.”

“No, there is a limit to how far I will go Mistress” Cecilia decided not to push his disobedience too far hence ‘Mistress’ and a curtsey.

“I am disappointed Cecilia, but if that is your decision, okay, lock your chastity back on.” Cathy repeated how she was not the same as Julie “you can tell me when you are ready to be released….”

“Thank you Mistress.” 

“Let me finish, you can tell me when you are ready to be released….by asking to taste cum.”

“Can we talk about this?”

“We just did Cecilia - a taste of chastity until it’s a taste of cum, your decision when that is.” Cathy turned in the doorway “please serve coffee in the lounge room once you are properly dressed.”

The image of a 'teenage-like' Cecilia was still fresh in Cathy's mind the next morning. Where better to show off Cecilia on Saturday morning than the mall? Too close in age to be mistaken for mother and daughter, passersby might assume they were older and younger sisters, friends, or even lesbians if someone picked up on hints of butchiness. All possibilities were fine with Cathy.

After breakfast Cathy instructed Cecilia to change out of her maid uniform.

He slipped his only dress over his head, his bra helped it fit better across the bust, but his tightly corseted waist was now lost within its flowing fabric. Cathy sat him down in front of the mirror in the maid's room, Cecilia lacked the skills to create a shopping mall look. “You need to practise doing this, Cecilia,” Cathy said while applying makeup and gel to Cecilia's hair, Cathy stood back. “There, now you look totally passable.”

She handed Cecilia a small cosmetic bag. “Put this in your purse, then come to the car.”

As they drove two towns over, Cathy’s tone softened, she used travel time to coach Cecilia in speaking in a more feminine way, suggested simple phrases to get through interactions at the mall. “Don’t worry,” she said. “Even if someone does figure it out, they won’t let on.” Her voice was light with a hint of playful, as if Cathy were twelve and Cecilia were her favourite doll. 

The mall was far enough away that they was zero chance of meeting someone either knew. First stop the costume jewellery store, Cathy said she was going to have Cecilia's ears pierced. Cecilia resisted with a firm “No” Cathy took him to a nearby coffee shop to talk.

"What did Julie tell you?" Cathy asked.

“She suggested I use the week to make sure I want to be Cecilia above all else”

“Then grab this chance with both hands and try out Cecilia’s life.” Cathy smiled “remember, this is real life, and remember Peter can walk away at any time. I’ll try again, does Cecilia want earrings?"

Cecilia felt a lump in her throat. “Yes please Mistress.”

“I’m thinking how I will punish you for disobeying me…and you can drop the Mistress'" Cathy said. “We’re just two friends shopping. ” Nothing could have prepared Cecilia for what happened next:

"My boyfriend wants a gold stud in each ear," Cathy told the ear piercer. “While you’re getting that done, sweetie, I’m going to browse.” Sensing another opportunity Cathy smiled to herself as she looked at fake engagement rings - her mind ran riot!

Ear Piercer had Saturday Girl assisting, they smirked while marking up his ears “Are you really a man?” Saturday Girl asked Cecilia, Ear Piercer shushed her, gave a little shake of the head as if it would silence Saturday Girl in the same way a shake silenced her AirPods. But Saturday Girl was not finished “you get many customers like him?”

Ear Piercer answered quietly “mostly real men getting one ear, not many sissies like this one come in…nothing personal sweetie.” Ear Piercer went back to  a smirking silence as she fired the piercing gun.

Cathy stayed within earshot while selecting a costume ring from the counter. Waiting until he was beside her she said, “Peter, I bought you a present for being so brave. You need an engagement ring, just like I do - you know - for the times you want to avoid attention from unwanted men.”

“As far as I am concerned all men are unwanted.” Cecilia blushed as the sales assistant asked if he needed a bag or would wear the ring. 

He waited until they were outside, “and I do not want any men looking at me,"

“Liar! I saw you smile at a cute guy in the coffee shop earlier.” Cathy giggled. “And he smiled back.”

Cecilia attempted to change the subject, bringing up Cathy’s relationship with Jim, saying he was scared of being seen by Jim in the coming days.

Cathy was pleased Julie had not bothered to update Cecilia on her boyfriendless status, she liked his insecurity and teased: “He’s just my boyfriend, it’s not like we live together, he won’t be around when I am not there. I mean… I want to be there to see that meeting.”

Shopping continued, Cathy noted the styles younger women wore and picked out a shorter, form-fitting dress for Cecilia. She came into the changing room with him, “cute but not slutty, I want you to wear it home” she said as she pulled the tags “and the pleated skirt totally hides your little boy bits,” sniggers came from an adjoining cubical, they joined the end of line for the register, “I told you there was no need to be nervous.” Cathy smirked “Not a single person has noticed after two hours at the mall Peter.” She playfully kissed his cheek. “Sorry, I mean Cecilia.”

A group of teenage girls along the line turned to stare. Cathy couldn’t help but giggle. Now certain of his clothing sizes she left Cecilia in line to pay while she wandered looking for another outfit for her Cecilia-doll. 

During the drive home, Cathy mock admonished Cecilia accusing him of pretending not to enjoy humiliation. 

Cecilia smiled “how could I not play my part Mistress when you take so much pleasure from seeing my pain.” 

“Then we are both on the same page?” 

“Indeed Mistress.”

Cathy instructed Cecilia to enter through the back door and change into his lilac uniform. “You need to catch up on your chores,” she reminded, her tone returning to firm once more.

***

“Do you need this?” Cathy wiggled the key.

“No thank you Mistress.”

“Why are you being so stubborn Cecilia?” He said he did not need to ‘acquire’ a taste for semen. “Better to be prepared” Cathy smiled as she listed all the things he once did not need that ranged from wearing a dress to being humiliated. “Better to have something and not need it than need something and not have it.”

“I already have something I may not need.” Pleased by Cathys confusion, Cecilia saw a chance to take control of the conversation and his relationship with her. “Cathy, I  booked a second week off work…” his confidence began to wane but he had gone too far to stop. “If you need me, that is, Mistress.”

 Cathy smiled. “Staying at the apartment with Julie would feel awkward?”

“That as well Mistress… I was thinking with a second week I could ōhsōji, like spring cleaning but…”

“In autumn, I get it” Cathy said, “perhaps it’s time to have ‘the talk’ about where we are headed”  

“I could be your Maid all the time… after work, weekends, whenever you want Mistress.” Cecilia had a game plan all worked out in his head, Cathy asked where he would live “I could get a bedsit or, I was hoping to stay in the maids room. That way I would always be available, if you want that I mean.”

Cathy had a plan as well, and Peter coming and going was not a part of that - neighbours, gardeners, tradesmen, boyfriends would see a man coming and going. “My maid would be here when the man was not and vice versa, can you see how people will soon realise Cecilia.”

“Boyfriends, you mean just for you Mistress?”

“Drop the mistress for the moment, of course boyfriends for me, I have no romantic interest in you Cecilia.” She noticed his eyes welling up and quickly added “my feelings for you are strong - but as my maid, not as a partner Cecilia you must understand and accept that before we talk further.”

“I thought you watching me…”

“That is first step in using masturbation for control.”

“I’m sorry for misinterpreting.” Cecilia sounded casual while inside his excitement peaked… first step!

Cathy said that he was welcome to become her full time, live in maid, “that is twenty-four-seven. Medical emergencies aside Peter would be no more. Take some time to consider everything.” Cathy kissed his cheek “But no backing out of the second week Cecilia, your ōhsōji offer sounds perfect. I’ll let Julie know not to expect you at the apartment next time we speak.” 

Giving up a secure job to play maid to Cathy was a step too far for Peter. He took advantage of the thinking time to formulate plan 2.  He quickly changed into his Peter clothes when Cathy left for work, met Jasper, his coworker-friend from human resources for lunch. Peter invented a cousin named Cecilia, she had been offered a position as a live in maid and she wanted an employment contract that stacked the odds in her favour. Jasper smiled said he loved a challenge, they shared ideas. 

Cecilia said he was ready to talk about Cathys offer. “I am happy with what you offered Cathy but I need a contract.”

“Like you are my indentured Maid or a slave contract?” Cathy could hardly hide her excitement.

“You want me to give up a secure job, I like that security Cathy. I need an employment contract that maintains my job security.”

Cathy took the proffered paperwork; minimum wage, 20% deduction for board and food, free uniform, 40 hours flexible, extra hours optional, 3 written warnings before dismissal, appeals procedure, the small print went on and on. Whereas Cathy would find it difficult to dismiss him, Cecilia could leave at any time  - every detail was set out. Cathy could hardly believe what she was reading. This was like a reverse slave contract but, most importantly, one that could be legally enforced. 

Cecilia clearly wanted to be her maid for the foreseeable and that suited Cathy perfectly.

They each signed a copy, Cathy instructed Cecilia to open champagne to seal the deal. “We need to choose a safe word” 

Despite understanding what a safe word is Cecilia employed a look confusion, Cathy explained how a safe word works, that it needs to be a word that could be incorporated into a sentence or to work as a stand alone word - “something like ‘fish’ or ‘uncle’ or ‘rain’ you could simply say the safe word - perhaps if I am punishing you in some way. Either of us can say the safe word and we time out.”

He considered in silence until Cathy was mid champagne sip. “My uncle just walked past the window.”

Cathy turned her head “where?”

Cecilia laughed “uncle works in a sentence as well.”

***

Cathy drank the lions share of the champagne, she told Cecilia she needed help preparing for bed, instructed Cecilia to set the shower and without a trace of self-consciousness, she began undressing, carelessly dropping her clothes on the floor. “Hang my dress, and put my undies in the hamper, Cecilia,” she said as she stepped into the shower, her tone light with commanding undertones.

Cecilia, bent down to pick up Cathy's discarded clothing. As he hung the dress carefully, Cathy called out for him to tidy the room. When Cathy emerged in a bathrobe she busied herself setting up her iPhone on the dresser, aiming it directly at the bed. She nonchalantly tapped the screen to record, smiled into the camera. Cathy sat on the edge of the bed. “I am going to start your employment with an extra task. Kneel, Cecilia, and massage my feet,” she ordered with a big grin.

Cecilia knelt in front of her, hesitating briefly as he began rubbing her feet. Cathy's bathrobe parted as she shifted, revealing more than he was comfortable seeing. He quickly lowered his eyes, focusing solely on her feet, trying to remain undistracted.

“Hmm, that is wonderful, heels are such a pain, and yet you manage so well Cecilia, that feels wonderful…my calves are tense. You’ll need to work on those too,” Cathy leaned back on her hands, letting her legs part. “Thighs next”

Cecilia froze. “I’m not sure a maid should be going any further, Mistress,” he replied, his voice shaky, hoping for a reprieve. 

Cecilia hesitated one more moment, then placed his hands on her thighs, massaging them as instructed. Cathy’s face softened with pleasure, her eyes half-closing as she leaned back further on the bed. A satisfied smile crept onto her lips. “That feels good…what a perfect sissy maid you are,” she purred, a moan escaping as she revelled in her control. “your hands are good, it’s time to find out how your tongue skills are.” Cathy let her legs spread wide.

Cecilia couldn’t take his eyes from her welcoming pinkness, he moved forward, parted his lips. It was as if Cathy had a remote that controlled his tongue. Sleep evaded him that night, he hoped the evening would form a regular part of his duties. 

Next morning Cecilia prepared a tray with two cups, as instructed, brought it to the bedroom. Cathy was in the shower, and he placed the tray on the low table in front of the sofa. As he arranged the coffee, Cathy emerged from the bathroom, wrapped in a bathrobe, her hair still damp. She sat on the sofa and motioned for Cecilia to join her, patting the seat beside her. Hesitantly, he sat down as Cathy poured them both coffee.

Cathy sipped her coffee, a mischievous grin spread “you know, at work, female coworkers are always going on and on about sex,” she began, her tone casual but playful. “It’s like a religion to them - at the water cooler, coffee machine, lunchtimes.” Cecilia listened “and when they get onto blow jobs they can’t get enough of it - ‘Oh, it’s so rich,’ they say. ‘It’s the perfect mix of sweet and salty,’” Cathy mimicked, rolling her eyes in exaggerated mockery. “And then, of course, there’s Julie.”

Cecilia tensed at the mention of Julie, wondering how she fit into the story.

Cathy’s smile widened as she continued. “Julie’s the only woman in the entire office who doesn’t fall in line with the oral obsession. She just walks away, totally appalled. She calls putting a cock in her mouth or a man putting his tongue in her cunt disgusting, perverted, like she can’t even imagine why anyone would do it.” She watched Cecilias confusion, his nervous sipping to avoid speaking. “Is Julie the reason you refuse to taste cum, or are you ready try? You might like a ‘perfect mix of sweet and salty’ in your mouth.”

12 - The Homecoming

Cathy moved swiftly to consolidate her control; ordering hormones, t-blockers and booking laser facial hair removal. Saturday morning Cecilia lay beside Cathy in a sleek, modern salon chair, both booked for a makeover that incorporated a body-wax, highlights to his pixie cut, nail polish, lip fillers.

“Despite appearances, Cecilia is, in fact, a man.” Cathy pre-warned when making the booking at the salon three towns over and Nishina didn’t bat an eyelid during his body wax.

The soft hum of hair dryers and the light chatter of stylists filled the air as the makeover team worked around them. The warm scent of hair products mingled with the cool aroma of coffee was new yet calming to Cecilia.

“Hold still,” one of the stylists said softly, as she teased Cecilia’s hair up to create a modern spiky look. Cathy smiled as she watched as it was cut and styled perfectly. The colour was new as well - a soft chestnut brown with warm highlights, a slight contrast to Peter’s natural shade, but Cathy knew it would not go unnoticed. His new short, easily managed hair was both fashionable and ideal for a busy maid.

His lip fillers transformed Cecilia’s once sharp, thin lips into a Cathy-esque subtle pout, as if they were both poised to gently blow on steaming macchiatos.

The stylist assessed his skin tone carefully, dove into her makeup tote, “something daytime natural but elegant I think,” in a professional and friendly tone. Cecilia simply nodded, letting the process continue as soft brushes swept across his face, highlighting his cheekbones, defining his eyebrows, and giving him a soft, feminine glow.

Then, without even a hint of ‘ta-da’ their makeovers were complete. Even to Cathy’s critical eye barely hint of Peter remained.

Leaving the salon with coordinated makeup, matching nails and lips they had the look of a pair of delicate handmade cups - crafted by the same careful hand, yet each with its own unique details. 

Cathy wore her excitement like a new fedora hat as they walked into an upscale boutique, where racks of high-end fashion greeted them. She wasted no time, flipping through the selections with the confidence of someone who knew exactly what she wanted.

“This,” Cathy said, pulling out a tailored dress in a soft blue fabric. It was chic, elegant, and sophisticated - perfect for the occasion. “Go try it on.” Cecilia stepped into the dressing room, slipping out of her casual clothes and into the form-fitting dress. When she emerged, Cathy’s face lit up with approval.

“You look amazing,” 

Cecilia stared at her reflection in the mirror, barely recognizing himself. With Cathys guidance they completed the look with matching heels, a delicate necklace, and a small clutch-bag before heading out into the midday sun. On the way to Julie and Peter’s apartment Cathy enthused “you look perfect, just wait until Julie sees you.”

“Cathy, I’m not sure about this, I think Julie is expecting Peter.”

Cathy smiled, said they could go buy some Peter clothes if that is what he really wanted. 

***

Julie opened the door, her face momentarily frozen in shock as her eyes landed on Cecilia. She was expecting Peter, her Peter. But her Peter wasn’t to be seen. In his place stood a well-put-together woman who could have passed for Peters sister (if such a person existed).

Cathy felt her chest swell with pride as she stepped aside to let Julie take in Cecilias every detail. “What do you think?”

Julie blinked, her shock obvious, her eyes lingered on Cecilia. “I… I didn’t expect all this,” she swept her hands in Cecilias direction as if casting a spell that she hoped would instantly transform him back into her Peter. “Why Cathy?”

“I wanted Cecilia to look his best for meeting you today. It is a big day for both of you, after all.”

Julie nodded slowly, inner Peter recognised a trace of sadness in her eyes as she turned away toward the living room. “Shall we sit and get down to business, go over the final details of selling the apartment.”

The air was thick with unspoken emotions. Julie looked at some space between them, her voice calm but strained. “I’ll be moving back to my parents’ house next week.”

Cecilia nodded “you could stay here, I plan to take my things today, stay with Cathy.”

Julie’s gaze shifted toward Cathy, then back to a space not occupied by Cecilia. “Well, I never expected other woman to be Peter.”

“None of us saw that coming” Cathy joined Julie in a ‘yea’ type laugh and suggested “how about we grab a drink? The three of us can end the day with a happy moment.”

Julie hesitated, then nodded. “Sure, why not?”

The bar, already busy with the early evening crowd, was not a place they had been to before, Cathy asked what Julie wanted.

“Just a coke, it’s early”

“Same for me Cecilia, Julie and I will get a table” Cathy said. They watched Cecilia enter the throng of drink less drinkers vying to be served.

“Why did you bring him here like that - are you some sort of crossdressing magician?” Julie made no effort to conceal her anger. “Create Cecilia in your own image by all means… and don’t you think for a second I haven’t noticed every little detail… but you have no right to parade him like that, and in my own home of all places Cathy!” 

“I wanted you to see he is happy Julie, not let you continue imagining he is some pervert hiding in the shadows. And you are my best friend, so it’s not as if you two will never meet again.” Cecilia was walking toward the table.

Cecilia put the drinks down, the small talk flowed as if there were nothing unusual. Cecilia seemed oblivious to the searching questions Julie slipped in from time to time: 

I like your shoes, are they new?

That colour suits you, is that a new dress?

Where did you get your nails done?

Julie drained the last of her drink, she smirked “shall I send Cecilia to get another round of drinks Cathy?”

“No, I’ll go. I am sure you two have lots to talk about.” As she stood Cathy leant in to Julie said “please don’t hurt him Julie” quiet enough for Cecilia not to overhear. She took her time returning to the table, overheard Cecilia talking “…to be frank Julie I was terrified of you seeing me like this, I wanted to come in Peter’s clothes but Cathy had other ideas.”

“And you are okay with that?”

“I am now, I cannot believe how nice you are about this Julie.”

“It is not easy Cecilia.”

13 - The Cocktail Party

Cathy couldn’t help but feel a sense of satisfaction as Cecilia stood before the mirror in the maids room wearing only his corset, bra and stockings, he stepped into his heels. She was in complete control, and he was right where she wanted him - that place between obedience and arousal. Cecilia had lasted more than a week and he was not looking forward to tasting his cum.

“This is a special day,” Cathy said, with a glint in her eye. She watched as he stroked slowly to erection “if you can cum on command then you do not have to taste cum today. Fail and the price of release becomes higher.” 

His cock had her full attention, as she watched her mind seemed to take on the persona of a horse trader - she estimated the cock to be two and a bit of her hands, perhaps three. 

Cecilia had two choices:

1. Knock out an unsatisfying quickie.
2. Enjoy the moment and pay a penalty.

Cecilia chose option 2 and stroked at his favourite pace. Cathy counted 3…2…1…cum. 

He continued stroking casually, eventually shooting string after string of cum onto the mirror. Cathy scooped up a glob and fed herself Mmming. She repeated the process and fed it to Cecilia. He winced and pulled a face as he swallowed. 

“That was rude, you need to show appreciation, now try again.” 

Cecilia rebelled “one wank, one taste Mistress.”

“Pulling that face is not in the spirit of the agreement, thankfully there is plenty more cum and we have all day. Now, try again, here.” Cathy scooped a two finger glob from the mirror and held it out. Cecilia opened his mouth, Cathy told him to suck as she moved her fingers in and out slowly.

There was plenty more cum on the mirror and Cathy was in a mean mood, Cecilia demonstrated compliance with a mock eagerness. He licked his lips as she withdrew her fingers, “Mmmm, it really is the perfect mix of sweet and salty Mistress.”

Cathy watched, said he could consume the rest or lock himself in chastity. As he clicked the lock closed on his chastity she said “I hoped you would choose the first option, new game Sissy…” Cathy scared at the ceiling as if trying to calculate the number of minutes in a leap year, “you make such a mess on the mirror, next time we will use a wine glass.” She smirked “and now we both know how much you like cum you can drink it all. I will let you choose - down like a shot or sip, sip, sip.”

Cecilia settled into a routine; week days he arrived outside Cathys bedroom door as her alarm sounded, a little later weekends. He would tap lightly and take in her coffee. 

Every morning two tablets awaited on the vanity - one orange, one blue. He had worried first morning when Cathy told him they were hormones to make him a better sissy. From time to time she teasingly asked if the hormones had started helping him fill out his bra. After discovering vitamin bottles containing the orange and blue pills hidden at the back of Cathy’s closet he began to playfully react to her prompts; ‘my breasts feel so big today Mistress’ or ‘I will need a bigger bra soon’ 

Cathy noticed the sudden change, suspected he had discovered the two vitamin bottles in which she kept the hormones and t-blockers hidden at the back of her closet. Angela had suggested the re-packaging ruse during an online chat. Cathy loved the idea of him willingly taking hormones to please her.

Friday morning, as he tidied the bedroom and laid out her clothes for the day Cathy talked about her cocktail party as if they had spoken of it before. “Put fresh linen in the guest bedrooms, leave the doors ajar. Mrs. Green’s cook will send over hors d'oeuvres with Millie later.”

Cecilia curtseyed, “Yes, Mistress,” 

“Have you seen my grandmothers bracelet anywhere Cecilia?”

“No mistress.”

“I want you to search everywhere this week.”

As Cecilia went about his tasks, a wave of anxiety washed over him. Why had Cathy waited until the last minute to mention the party and preparations? Was it a test or was he being punished? Cecilia shook his head, deciding that this was a test of his ability to handle last-minute events.

Millie arrived mid-afternoon, as they worked together on the preparations, Millie commented, “You do well managing this place alone without contract cleaners to help.” Cecilia’s heart swelled with pride when Millie continued “Miss Cathy told Mrs. Green she couldn’t imagine life without her Cecilia,” Millie added with a wink. The compliment fuelled Cecilia’s efforts as she finished setting the house for the evening. 

Cathy looked stunning wearing a long burgundy evening dress. She gave final instructions to Cecilia and Millie, they were to circulate with trays of drinks and hors d'oeuvres after Millie had finished welcoming guests and answering the door. When all guests had all arrived, Millie would assist Cecilia. 

Cathy reminded the party would wrap up around 11.

As the night unfolded, the house filled with guests, and Cecilia moved gracefully through the rooms with her tray. “Everyone’s here,” Millie said when she joined him.

They were so busy time passed quickly, “one more hour, thank goodness. My feet are killing me.” Millie said as they recharged their trays again.

Cecilia noticed her - Julie! 

In the dining room. 

In conversation with Cathy and an older couple. 

Cecilia froze for a moment, trying to avoid eye contact, but it was too late. Julie had spotted him. She turned to Cathy, said something, and they both stared openly as Cecilia moved among guests.

***

Being seen by Julie in casual clothes had been nerve wracking, but that was nothing compared to the unprepared for, unexpected, humiliation of being seen in full maid uniform. He shuddered at the thought he would be forced to curtsey and call her ‘Miss Julie’ Heart pounding, he managed slip away before nearing Julie and rushed to find Millie. “Help me stay away from her, please,” he pleaded after describing Julie. 

Millie chuckled, said “no problem, at home there are male guests I avoid.” Without asking why?

Putting his personal anxieties aside Cecilia focused on being the best maid he could be by doing his duties flawlessly. As the last guests began leaving Millie whispered, “Relax Cecilia, she’s gone.”

Once the house had finally emptied and Millie’s taxi had arrived, Cathy called Cecilia into the dining room. Her expression was stern. “Why did you avoid Julie like that all evening?” she asked, her voice cold.

Cecilia, gathering her courage, attempted to explain. “Mistress, exposing me to Julie like that was cruel and…”

Cathy’s eyes flashed with anger, and she cut him off. “Julie is my friend, and tonight she was also my guest. You behaved disgracefully avoiding her like that. I am your Mistress, and don’t need permission who I invite here, one more thing” She paused, her voice softening slightly. “Don’t come to my room with coffee in the morning. I don’t know if anyone is staying over, have the morning room ready, keep fresh tea, coffee and juice on the table from 8 and be ready to serve cooked breakfast if needed.”

Cecilia lowered his eyes, his voice meek as he curtseyed. “Yes, Mistress, I will do better next time and treat Miss Julie as your guest.” Cecilia took a deep breath and began to clean up the remnants of the evening, his mind racing with the consequences of his actions and the reprimand that had stung more than expected

Cecilia set the table in the morning room, replenishing hot drinks regularly, the frying pan warming in case an overnight guest wants cooked breakfast. Cathy was first to arrive wearing running kit beneath a sloppy tee and ordered fresh coffee. She was joined by an older couple from the night before who had tea and toast and leave a few minutes later.  
Cecilia waited in the kitchen, the door to the dining room slightly ajar so he can listen for breakfast guests. His worst nightmare begins when he overhears Cathy call someone ‘sleepy head’ and Julie reply her bed was so comfortable she overslept.

“You just missed the Wilkinsons, they had tea and left.” Cathy said

“They enjoy last night?”

“I think so, talked about weather and suchlike, you know what breakfast chit chat is like with semi-strangers.” 

“I enjoyed last night Cathy.”

“Talking of last night, I tore my maid a new one last night for being so rude to you, I expect he will be a little more welcoming today”  Cathy said the coffee had gone cold and rang the little bell on the table.

The familiar ring of Cathy’s little bell sent a jolt through him. He quickly composed himself, and made his way into the room, rehearsing his apology in his head. “Good morning, Miss Julie,” he said with a curtsey as he entered. “I’m terribly sorry for my behaviour last night. It was very rude of me to avoid you.”

“We haven’t been introduced” Julie’s eyes twinkled with mischief as she looked him over “what is your name?”

Cecilia glanced at Cathy, who gave him an encouraging nod. “Cecilia, Miss” he answered, bowing his head slightly.

“Cecilia? Julie smirked “not Peter? Then turn around Cecilia so I can take everything in.”

Cecilia hesitated, but complied before Cathy reacted, feeling her eyes examining every stitch of his uniform, the tight fit of the corset beneath it. When he turned back to face her, Julie gestured for him to sit down.

He did so, perching on the edge of the chair, careful to maintain his posture. Julie’s brow furrowed slightly. “Why do you sit so upright?”

Cecilia took a breath before answering. “It’s my corset, Miss Cathy decided it was appropriate for me.”

Julie leaned forward, eyes narrowing. “Are you saying Cathy forced you to dress as her maid?”

Cecilia shook his head. “No, Miss Julie. What I mean is she guided me, I could have said no at any time. I mean I never intended to become a maid but once I was wearing the uniform I had no reason to go back.” 

“Like I can’t go back and unsee this?” Julie waved an arm

“He’s right Julie, I never forced him,” Cathy attempted to lighten the mood “but I did make it really easy for him.”

Julie raised an eyebrow, her expression skeptical but curious. “So, Cecilia you could say no to all this right now? Change and come home with me?”

Cecilia’s stomach twisted at Julie’s question. He glanced at Cathy, noticing a brief flicker of tension on her face. “In theory,” he began cautiously, “I could go change and be Peter again...”

“In theory?” Julie scoffed.

“I mean, if that’s what I wanted, but... I’m Cecilia by choice, Miss Julie. Mistress isn’t forcing me into anything.”

“Mistress” Cathy mocked and stifled a laugh, enjoying her game but not  Cecilia’s commitment to Cathy. “I told my parents I expected Peter would be here” Julie shook her head, her voice suddenly heavy with sarcasm . “I should get some pictures of you Cecilia so they can see for themselves exactly what my ex-boyfriend has become.”

“Cecilia, bring some fresh coffee, please.” Cathy waited until he had left “Why are you being so horrid Julie?”

“He’s so pathetic, Cathy,” Julie said effectively concealing the affection for Peter tugging at her heart.

Cecilia returned with fresh coffee, Cathy smiled and, before Julie could resume, said “take the day off Cecilia, go shopping, hide in your room with a book, or whatever… just avoid Julie. I think she has the beast visiting.”

14 - A Day out

“Today, you’ll be helping at the Green’s house for her Women's Institute meeting. Millie needs help with refreshments.” Cecilia nodded, his heart sank - another public display. Cathy, noticing his anxiety, added, “And Cici, I don’t think the ladies of the Women’s Institute will appreciate you bending at the waist. Today, you have permission to bend at the knees.”

Cecilia gave a small smile and curtseyed. “Thank you, Mistress.” He loved how Cathy would sometimes call him Cici when they were alone. 

He stood up and. Reflex like, collected the scattered laundry from the floor, bending at the waist. Cathy watched, “I see old habits die hard,” she teased.

Before he left, Cathy casually swung her legs over the edge of the bed, “I’m feeling tense this morning, can you help me with that…”

Cecilia smiled as he knelt.

Before leaving for work Cathy called Cecilia into the maids room room, she handed him an empty wine glass and unlocked his chastity “hold your dress out of the way.” He had lasted a month without giving in. “It’s for your own good” Cathy said in a no-nonsense way “men need frequent release, even sissy maids” 

Wine glass in one hand and hem of uniform in other gave Cathy the perfect excuse to assist, he seemed nervous as she squeezed out a palm-full of lube.

“This isn’t necessary Mistress”

His cock was already hard before Cathy slathered the lube over his cock and began stroking, the surplus of lube making slurpy slurp sounds when her hand gripped tighter “see anyone you know outside the window?” She teased.

“No Mistress.”

“A relation perhaps?” She teased

“Not a soul mistress.”

Cathy counted off strokes in-head, the silent stroke-tally passed her boyfriend best, daydreaming brought thoughts of not wasting it, thoughts of how it might feel inside her. As the cock in her grasp began to take on a life of its own she realised ‘mistress wanking maid’ was a step in the wrong direction.

Cecilia moved the wine glass into catching position. 

He slowly lifted the wine glass to his lips, tilted the glass slowly. As the contents neared his lips Cathy touched his wrist “not today Cici.”

***

The walk to Mrs. Green’s house took him through the village - alone, his formal black maid uniform drew far more attention than he was comfortable with. The frilly half apron, knee length skirt, and the click, clickety, click of his high heels seemingly demanding attention from everyone he passed, particularly the patrons of a café at outside tables. He felt their eyes follow him, heard his name whispered, heard Cathy mentioned somewhere among the tables. He walked with a confidence, each step steadier as he focussed on his forthcoming duties.

When he arrived at the back door of the Green’s large house, Millie greeted him warmly.

“Cecilia, thank goodness you are here! We have so much to do before the guests begin arriving,” Millie said with a grin.

Cecilia set to work, remembering Cathy’s instruction he asked “did you find a bracelet after the cocktail party?” She had not but promised to go on a treasure hunt when the house was quieter.

The Green’s house was far grander than Cathy’s, a full-time cook, chauffeur, and part-time domestic staff were employed besides Millie. The scale of the event was intimidating. Gradually, as the day progressed, Cecilia found himself becoming more relaxed just like he did the first time. He helped Millie with morning tea service and, later, with lunch in the formal dining room. Each task was carried out with precision, and by the time the lunch guests were seated, he was moving through the rooms with confidence.

In the quiet moments after serving lunch, Cecilia, Millie, and Cook sat together in the large kitchen for their own meal. Cecilia sat straight, his posture upright, the corset doing its job.

Cook, complimented his rigid posture, asked, “Is that the result of a corset?”

Cecilia glanced down shyly, feeling a bit exposed but eager to be honest. “I’m a little surprised you guessed correctly,” he said, his voice steady. “I’m training my waist. Mistress has promised me a custom corset once I can lace fully closed.”

Cook and Millie listened with interest, Cook nodding thoughtfully. “Ah, waist training. I’ve heard of that.”

Millie, though, looked a bit shocked. “You call her ‘Mistress’?” she asked, her eyebrows raised.

Cecilia smiled softly. “Yes, I do. I began addressing her Mistress, and she has not corrected me.” Both women seemed to accept his explanation, though Millie was clearly still digesting the revelation.

The walk home in the late afternoon was a different experience. The village was busier now, with more people about. But this time, Cecilia didn’t feel the anxiety of earlier. He walked with the confidence of someone who had proven themselves worthy of the uniform, inside he carried the knowledge that he had performed his duties well. Eyes that followed him no longer felt threatening but recognition of the role he had chosen.

As he neared Cathy’s house, home, his mind replayed recent events. If nothing else, they had taught him that he was capable of carrying out Cathys’ instructions, no matter how daunting. He felt a sense of pride in how far he had progressed. Whatever the future held, he would strive to be the maid who made his Mistress proud.

15 - The lost Bracelet

The entire office had heard the story of Cathy loosing her grandmothers bracelet often enough that everyone avoided any mention of jewellery in her presence lest it set the whole sad tale in motion again. 

As they had a pre-work coffee Julie broke protocol, casually asked if there was any news on the bracelet, during the retelling Julie suddenly exclaimed “were you wearing the bracelet that day you made your grand entrance with Cecilia?”

Cathy wanted to tell Julie to get over it but focussed on the bracelet. She clutched at the possibility “will you check for me, I know I sat on the sofa, it might have…”

“You can trust me to check thoroughly, only problem is the movers are coming today.” 

Cathy picked up her iPhone, her thumbs a blur as she asked Julie to delay the movers until the afternoon. “I have sent Cecilia to check.”

“Cecilia has a cell?”

“Do dinosaurs walk the earth?” Cathy laughed, “I make him carry a pager. That was difficult enough.” 

Julie joked about Cecilia being in a fluster at being dispatched on public transport. 

“That is brilliant Julie! I did tell him to take a taxi.” Cathy said with glee as she tapped away “now he is taking public transport. He will be so nervous he’ll be pissing his panties.”

Thankful Cathy did not send instructions to the contrary, Cecilia changed out of uniform; swapped his bra for his new ‘wonder bra’ - the one Julie had him wear the day she took him to the apartment. Next came leggings, white sport socks, white ankle-converse, and layered tops. He checked the mirror, saw a casual dressed woman, people would assume was shopping or gym, that sort of thing. He added the pleated, short, grey skirt that Cathy always said ‘looks cute’ with leggings, and he thought ‘hides chastity’ before heading out. 

As Cecilia neared the bus stop in the village his anxiety levels jumped up a few notches. He dug wired AirPods out of his purse, popped them in and slipped the cable end in his pocket to avoid people talking to him. He had practised and mastered ‘maid phrases’ and ‘mall phrases’ but not ‘bus small talk’

His light-bulb moment came as he waited for the second bus. Cathy had some humiliating event planned he decided. Rather than fret over what might be he decided to enjoy the day. If Cathy wanted to humiliate then Cecilia would be fine with that. Nothing could have prepared him for what awaited.

***

Julie smiled, she lightly lip-kissed Cecilia and said she had come to help look for the bracelet. Said she had put the movers off until 12:30 while making coffee, “no rush Cecilia, I will drop you home tonight on my way to my parents.” As much as she told people she was over him Julie has still not fully convinced herself, even seeing how he was dressed did little to change those feelings. Alone with him and dressed as a woman in their apartment for the second time felt less awkward. 

She had never been that type of person, the type of person who could stop loving on demand. In Julie’s head the next hour would be a test to see, once and for all, if she could tolerate Cecilia and continue loving Peter. 

They searched the lounge room, Julie’s constant smalltalk about life as a maid began to relax Cecilia. “I wish I had been less uptight about your crossdressing when you first told me” Julie said out of the blue, “I mean, it’s like now, I am perfectly okay with us spending the day together, and I think we should go to lunch one last time - like in the old days.” She said as they sat on the sofa.

“You mean like the last supper?’  Cecilia said with a smile.

“I like you have not lost your sense of humour.” Julie kissed his cheek, noticing for the first time the softness of his skin, “some couples have break-up sex as well.” She took a familiar key and a condom from her purse.

“Are you serious?” He wanted sex a little more than he wanted to ask so many things; did Cathy engineer this? how else would Julie have a key? was this Cathys way of proving she held no feelings for him?

Cecilia was not the only person in the apartment  thinking of Cathy - Julie imagined Cathys anger when she realised she had been manipulated. She led him to their couple-bedroom “do as I say.” She pulled his leggings down as far as his knees, his panties followed. “Lay on your back.” Julie liked how the bare mattress added a sense of cheapness to what she was about to do. She tried putting the key in the chastity, looked at the lock a second time - it looked the same, “when did Cathy change your fucking lock?”

“She changed my lock?” Cecilia reasoned Cathy was testing Julie - or them both - why was Julie so angry?

Julie regained control of her feelings, before the awkward foiled sex event she was enjoying being with him. Ignoring the clothes Cecilia was like a softer version of Peter. 

Julie liked that. 

She decided, in or out of uniform, she would make Cecilia a level one friend. And with the rest of the day before her Julie had opportunity to lay the groundwork for that friendship. “Cathy has you well trained.”

“I guess she has, what is with the condom Julie?” 

She smiled innocently “I stopped taking birth control pills while I don’t have a boyfriend.” 

There was a hidden message there but Cecilias inner man didn’t know what that message was. 

***

Cathy discovered Julies booth empty at lunchtime. Brittany said “she left the office first thing Cathy, right after talking to you.” 

Julie’s cell went straight to mail and texts remained dot-less. 

Cathy realised she had been played, Julie had embarked on one of her elaborate schemes. She went back to her own cubicle, let her mind wander over previous days and replayed one conversation in particular. 

The conversation - Julie saying she still had feelings for Cecilia and Cathy saying she saw Cecilia as a sissy maid, nothing more - played on an endless loop. Cathy smirked at her fortuitous farsightedness - day one she swapped out his chastity padlock. 

As much as Cathy would be devastated if he went back to Julie she would not resist.

The movers rang the bell “get the door Peter” Julie smirked at him, saw him pretending not to be embarrassed as they came in, “we will get out of your way…come along Peter.”

“Why are you doing this?” He asked in the elevator.

“Cathy told me public humiliation is compulsory for sissys” she part-lied. Putting events in the apartment behind her she led the way to the café across from their apartment building. The retired couple, who lived along the hallway from their ex-apartment, waved to Julie, she smiled at Cecilia “Hi Albert, hi Bertha” Julie kissed cheeks.

“Hi Julie, have we met your friend…”

“Do you not recognise Peter?” Julie sat, motioned for Cecilia to sit. “Mind if we join you?” Pleased with the puzzled looks she wasted no time in explaining “he goes by Cecilia now.” Julie began to understand the pleasure Cathy took in humiliating him. 

Emboldened by the result of exposing him, and the questions Albert and Bertha posed over lunch, Julie and Cecilia spent the afternoon window shopping.

***

Early evening Julie pulled into the pub carpark and soon they were sat at a table sipping on soft drinks. Julie said she had enjoyed their time alone “I want us to stay friends, so no more Miss Julie when I visit.” 

He said he would also like that, “you better run that past Cathy.”

“Sure, but like in this bar it’s Julie. Right?” They sat quietly talking over the afternoon. 

“there’s Julie!” someone at the bar said loudly. Seconds later several women slid into the booth. 

Julie introduced him to her coworkers “…and you know Cathy of course.”  She took pleasure in seeing how Cathy and Cecilia shared the same look of impending doom. “As I am driving Cecilia home I’ll be designated driver for you Cathy, and anyone else who needs a lift.” She stayed on soft drinks for the evening to make sure not a second was forgotten.

Brittany led the interrogation of the newcomer to the group, soon they were asking about Cecilia’s job. He explained he used to work in tech support, someone interrupted asking if he knew Julie’s ex. “You mean Peter, that is how I know Julie” Cecilia said with newfound confidence “and once you know Julie you soon know Cathy.” 

“So we can come to you for the gossip.” Brittany said.

“Oh I know so much it is more a case of where could I begin.” Cecilia noticed Cathy shaking her head. 

“What do you do now?” Brittany asked maintaining lead interrogator role. 

“Oh I am a domestic, less stress and a better working environment.”

Before alcohol loosened his tongue any further he was bustled into the back of the car. They rode in awkward silence for a while, Cecilia realised if he wanted to talk freely the car was the place, he said how Julie had taken him to a new level of humiliation, not a brief exposure in a shop but an extended exposure that lasted throughout the lunch.

“And what about the morning, what happened then?” Cathy asked in a spider to the fly way.

He relived changing clothes, bus rides, searching for the bracelet, and like a runaway train, relived the bed scene, “and then… well I know you already know this part Cathy, but I need to say it… the key did not fit, so there I was locked away frustrated, thank you for arranging today Cathy, I love you so much.”

Julie looked in the rearview, “what did you say?”

“I thanked Cathy, said I love being controlled so much” he lied. The second he dropped the L-bomb he realised there would be repercussions. 

Cathy was thankful when Julie pulled into her drive soon after “I shall not need you tonight, go to your room.” Cathy could see her friends tears, streaked makeup, she leant across and took the car key “don’t take any notice Julie, he is a little drunk. It’s late, please stay tonight or for the weekend if you can.”

16 - Sissy Surgery

Cecilia served coffee, without looking up, Cathy broke the silence. "I came across an article online," she said casually. "It’s about a company in Europe that specialises in something called ‘sissy surgery.’"

Cecilia’s brow furrowed, not sure what she meant. "Sissy surgery Mistress?"

Cathy’s eyes twinkled with mischief as she leaned forward, setting her phone down. "Yes, they offer this package where they shave down your Adam’s apple, tighten your vocal cords to give you a higher voice, insert hormone implants, and soften facial features to make you look more feminine. Make sissies more passable, you know."

Cecilia blinked, taking in the information. “Mistress, people who now me would notice if my voice or face changed suddenly."

An involuntary grin spread, she was enjoying the unease in his voice and plowed on. "They offer next-level procedures for committed sissies if you’re interested. Ever considered an orchidectomy?"

Cecilia stared blankly at Cathy, confusion written on her face. "Orch-what?"

"You know," Cathy explained, her voice light but teasing, "castration, for sissies who want to prove they are not real men.”

Cecilia shifted in her seat, still trying to process what Cathy was saying. In an attempt to distance himself said  "so… they, I mean those sissies wouldn’t be able to, you know, get aroused?"

Cathy smirked. "That’s not how it works. They can still get aroused, just without... a certain messiness."

Just as Cathy was about to delve deeper into the topic, her iPhone buzzed. She picked it up, glancing at the screen. “I have to take this,” she said, getting up and leaving the room. “We’ll talk later, once you have thought it over.”

For Cecilia the conversation was far from over. Dread of sissy surgery lingered in his mind no matter how hard he threw himself into his tasks, haunted him in the sleepless nights that followed.

Unwilling to let sleeping dogs lie Cecilia broached the subject the first time he was out of uniform - during the drive to a mall "Cathy… about that surgery you mentioned, is it something you are thinking of for me?"

Cathy looked at Cecilia thoughtfully, as if weighing her words carefully. "I don’t think I should be the one to tell you what to do, make the decision for yourself." She smiled warmly, though there was a glint of excitement in her eyes. "But if you do want it, I’d support you one hundred percent. I will even pay for it."

Cecilia’s heart skipped a beat at Cathy’s casual offer. “Would I have to have everything?"

Cathy’s smile grew wider. “Well… I’m happy with the way we are now, but if you wanted to dip your toe in starting with one or two things, I’d be even happier. It’s your body, though. You have to make that decision."

"I’ve decided," he said quietly. "I want to go ahead with the Adam’s apple shaving. And I will get the orchidectomy if that is what you want.”

“How would your chastity work? I am not sure I want you wanking at will.” Cathy said cautiously, “we could add something  like a vasectomy or have you considered hormone implants?”

“I’ve not told a living soul about this…” He was careful to get Cathy to promise secrecy before his big reveal “too late for a vasectomy” and went on to explain children had never been part of his life plan, he had a vasectomy when he was twenty. “Hormones are a big step Cathy.” 

Cathy said “it would save taking two hormone pills every morning.” 

He claimed he thought the changes to his chest were a result of wearing a bra. Cathy giggled “sure you did.”

“I’ll think about the hormone implants, meanwhile can I have my Adams apple shaved please?”

Cathy’s eyes lit up with enthusiasm. "Are you sure?"

Cecilia nodded. “Yes. I have to be careful how I hold my head, how I swallow and I do not want to risk embarrassing you or me Cathy.”

Cathy’s excitement was obvious, she pulled into a parking bay, handed him her iPhone. “I have the perfect clinic in mind, check it out - a really modern place just two hours drive. Nothing but five-star reviews. They’ll take great care of you."

Cecilia hesitated for a moment. "You don’t need to come with me. I don’t want you to see me until I’m fully healed."

Cathy tilted her head, a little surprised. "If that’s what you want. Would you like breast implants, too?"

Cecilia shook her head. "No, I want my bust natural, even small will be enough for me."

Cathy smiled approvingly. "Natural is best.”

***

Cathy was at work the morning Cecilia arrived home feeling nervous and excited. He tightened his corset a little more than necessary, put on his lilac day uniform and heels. He held his head high, admired his reflection. He looked and felt more Cecilia than ever before. He had taken the plunge, and though the path forward was still uncertain, he knew one thing for sure; there was no going back - even if he wanted to.

Cathy’s face lit up the moment she saw him, “you’re home” he held his head high, swallowed “you look amazing!" she gushed, rushing over to hug Cecilia. 

Cecilia smiled, his lips forming the soft pout Cathy had become accustomed to. "I can’t wait to get back to work Mistress," he teased.

Cathy’s laughter was warm and welcoming. "I’ve missed you, Cici." She stepped back, her tone suddenly more commanding. "Now, time to get back to work.”

17 - The Maid’s New Clothes

“You deserve a pamper session, and I have the perfect day planned.”

Cathy said “parcel up your uniforms and dress in something smart.”

“Mistress?”

“Now you wear your corset laced fully closed they are too big. Angela will have them altered, don’t look so worried Cici, I will buy you new ones to bring home today.” 

Cathy took him to her salon in the village rather than to a salon several towns away. 

Cathy had booked them in for hair and nails, she greeted her regular  stylist with a smile. “Hi Marie, I guess there is no need to introduce you to Cecilia.”

Marie raised an eyebrow, intrigued. "Oh, a customer bringing her maid, well Cathy, this is a first for me!" She gave Cecilia a once-over, “let’s get started then.”

“Cecilia is not at work Marie” Cathy said as she took the hair station next to Cecilia.

“I’m sorry if I embarrassed you earlier Cecilia” Marie said when she passed close.  

“Just split ends and add a little shape” Cecilia told his stylist, Kalina, his hair had grown out enough for a pony but not long enough for the style Cathy wanted. Their pampering session continued as they moved to adjoining makeup stations. 

Arriving at Eve’s Corsetry and Fine Lingerie Eve greeted Cathy and Cecilia warmly “I hardly recognise Cecilia.”

Cathy beamed. “He’s come a long way, hasn’t he?”

Eve was impressed as she examined Cecilia’s waist, now tightly laced in a corset. “You’ve done a fantastic job of waist training Cecilia,” Eve said approvingly, helping to lace Cecilia into a smaller corset. The pressure was intense, but Cecilia could sense Cathy’s pride, and that made it bearable.

“Your custom corsets are ready,” Eve laid one out on the counter. “I suggest a night corset to help maintain the progress while you sleep.”

Cathy’s eyes lit up at the suggestion.“would you like a bra fitting Cecilia.”

Cecilia didn’t argue. He knew full well that Cathy’s innocent public suggestions were, in fact, instructions. Rather than the padded bra that he was used to Eve handed him an underwired bra without padding. 

Cathy watched as he put it on and situated his budding breasts in the cups. Recently his breasts had been undergoing a growth spurt. Cathy loved how, initially, he had been embarrassed by his pert little breasts and erect nipples surrounded by wide areola. Now, even under the watchful eyes of Eve and Cathy, that shyness had evaporated, clearly replaced with feeling of pride.

Eve adjusted the shoulder straps “He is developing nicely Cathy, 36a.”

“Please may I wear my new underwear Mistress?” 

“Have you forgotten we are going to the uniform shop?” Cathy smiled “That bra is virtually transparent.”

“I hadn’t forgotten Mistress.” Cecilia said with a smile.

They left the shop with new corsets and a bunch of 36a bras, headed to their next destination: Industrial Uniform Suppliers.

Angela greeted them both warmly. “Cathy, Cecilia, welcome back! Let’s get you measured for that new, smaller uniform,” she said, eyeing Cecilia’s corseted waist with approval.

As Angela measured him, she and Cathy chatted as if he were not there. 

“I thought you had given up” Angela said. 

Cathy had not visited the mistress chat in a long while “pressures of work” She lied “you know how it is. Cecilia is pretty much fully trained now.”

“I can see that” Angela said lightheartedly “what colours today?”

“A pale blue daytime uniform, I think,” Cathy decided.

“What a wicked mistress” Angela laughed, teased “faded blue, will be a subtle reminder of his fading manhood.” 

Cathy added a primrose uniform to the pale blue uniform along with a black one. Like a proud mother sparrow looking at her brood Cathy’s breast swelled with pride when Cecilia said “may I wear uniform home Mistress.” 

Leaving the shop Cecilia held his head high, pleased by the restriction if his corset beneath his new baby blue uniform. “It’s rather short Mistress” he said in the car as he tugged at the hem and saw Cathy smile.

“It is rather.”

Back at the house, Cathy watched Cecilia unwrap the parcel of uniforms. He carefully lifted out the lemon uniform, the black one, the clothes he had left home wearing - another uniform remained - one identical to Angela’s uniform.

“Mistress,” Cecilia said hesitantly, holding up the uniform. “Angela put this in the parcel by mistake.”

Cathy looked, her eyes revealed amusement. “Hang it up carefully, I don’t want it getting creased before I take it back on Monday,” 

Cecilia nodded and returned to the kitchen to begin preparing dinner.

***

Cecilia was taking laundry from the machine, sensing Cathy behind him he spoke, "Mistress, do you have a list of tasks for me while you’re at work?"

“Come with me” Cathy was dressed for work, she opened his closet, pulling out the Industrial Uniform Suppliers uniform. "Try it on. I want to see how it looks."

Cecilia hesitated, but did as he was told, changing into the uniform. Cathy’s playful tone continued, "follow me."

Curtsey, “yes mistress,” curtsey.

Cathy was at the front door, already closing it behind her. "Mistress, please! Let me back inside!" he begged, fear evident in his voice.

But Cathy only smirked, unlocking her car. "Get in the car," her voice teasing but firm. "Trust me, Cecilia, you don’t want to be late for work. Angela is a much stricter boss than me."

Reluctantly, Cecilia got into the car, dreading what was to come. Cathy stopped a couple of streets away from Industrial Uniform Suppliers. Cecilia’s heart pounded as he walked the busy road, the unfamiliar uniform clung to his body in a way that made him hyper-aware of every movement. The mid-thigh length uniform was shorter than anything he’d worn before, its tailored bust and thin fabric accentuated his new brassiere. 

Cecilia noticed a group of men standing at a tea bar. They were chatting, but as he passed by, their conversation halted, and he felt their eyes follow him. His face flushed with embarrassment Without reason he convinced himself they could see through the illusion - see him for what he truly was, a crossdressed man. But their gazes lingered only in appreciation, not suspicion. To them, he was just another woman walking down the street.

He breathed a small sigh of relief as he approached the Industrial Uniform Suppliers building. Angela was standing by the counter, her arms crossed with her usual air of superiority.

"Good morning, Angela.”

Angela's smirk widened. "Good morning, Cecilia. This is Diane."

Diane, a younger woman with bright eyes and a friendly smile, waved. "Nice to meet you, Cecilia," she said warmly.

Cecilia nodded politely, grateful Angela had not forced to curtsey. Angela put him to work, starting with cleaning the staff room and the toilets - something that had probably not happened in years. The task was humiliating, yet oddly grounding. He scrubbed floors and sinks soon lost in thoughts of how far his transformation had come.

After lunch, Angela sent him to the packing room to assist Diane wrapping orders - a simple enough task, Diane was full of questions.

"So, how long have you been working as a maid?" she asked casually, her hands busy folding boxes.

Cecilia hesitated. "For a while now," he answered cautiously.

Diane raised an eyebrow. "Angela tells me you used to be a man," she said suddenly, her tone playful but probing.

Cecilia’s heart skipped a beat, and his mind raced to find the right words. He glanced toward the doorway and saw Angela standing there, her arms folded, a smug smile on her face. She was enjoying this.

"I... still am," he said, trying to maintain a sense of dignity. "Miss Cathy prefers it that way."

Diane’s eyes sparkled with disbelief. "Really?" she said, her voice full of skepticism. "Because I've been watching you all day, and I don’t see it. You really look the part, Cecilia."

Angela stepped forward, clearly amused. "Oh, don’t waste your time, Diane. There's nothing to see. His Mistress has him locked in chastity."

Cecilia froze as if he could simply will himself invisible. Diane looked intrigued.

"Chastity? What’s that?" Diane asked.

Angela didn’t miss a beat, she explained in an almost bored tone, as if it were old news “It’s a device to prevent sissies like Cecilia here from touching themselves. Keeps them in line."

Diane’s eyes widened. "What does it look like?" she asked, leaning closer toward Cecilia.

Angela smirked. "Go on, Cecilia. Show her."

Cecilia’s blood ran cold. "I’d rather not," he murmured, his voice barely above a whisper.

Angela laughed. “Well sissy, Diane and I could take a look ourselves, couldn’t we?"

Before Angela could act on that threat, Cecilia reluctantly complied. His hands trembling, he lifted the hem of his dress and lowered his panties just enough to reveal the chastity device. He didn’t look at either of the women as he did it, wishing the ground would just swallow him whole.

Angela grinned. "See? If he wants to touch a cock it needs to be a real mans cock. Does Cathy let you do that?” She bobbed her head back and forth. 

“No she does not.”

Angela turned on her heel and left laughing.

Diane, suddenly looking uncomfortable, leaned in toward Cecilia after Angela left the room. Her earlier boldness had evaporated, replaced with a softer, almost apologetic tone.

"I’m sorry," she whispered, glancing toward the door to ensure Angela wasn’t within earshot. "She made me take part. And how could I refuse? I really need this job."

Cecilia nodded, his voice flat. "Don’t worry."

Diane sighed, her eyes filled with sympathy. "Just... be careful. Angela’s got something much worse planned for you tomorrow," she warned quietly.

Cecilia’s heart sank but he forced a polite smile, nodding in acknowledgment and getting back to work.

At the end of the day, Angela handed him a small amount of bus money. “Use this to get home,” she said curtly, not sparing him any more attention than she deemed necessary.

The bus ride home took an agonisingly long hour which felt like an eternity. He let himself in through the back door and quickly changed into his black formal maid’s uniform, only to realise that this dress was even shorter than the one he had been wearing. He sighed, knowing that Cathy had done it on purpose.

When Cathy saw him, she was delighted. Her eyes lit up as she looked him up and down, clearly pleased with the sight before her.

"Oh, Cecilia, you look absolutely adorable!" Cathy beamed. "I just have to throw a cocktail party to show you off. Everyone will love seeing how cute my maid is."

Cecilia curtsied, his face flushed with embarrassment. “Thank you, Mistress,” he murmured, bracing himself for what was to come next.

***

Cecilia stood outside Cathy’s bedroom door, holding a tray of freshly brewed coffee. He had been awake all night, tormented by dread of whatever Angela had in store for him. His plan was set in motion hours ago when he carefully dressed himself in his new baby blue maid uniform, complete with sheer, seamed, blue stockings he had purchased on his nerve-wracking journey home the previous day. His uniform was immaculate, with a mop cap perched neatly on his head and a half-pinafore tied around his waist.

He waited for the sound of Cathy’s alarm and gently tapped on the door.

Cecilia smiled nervously and busied himself tidying the room while Cathy sat up in bed, sipping her coffee. She took a moment to admire his uniform, her eyes trailing down to the stockings that highlighted his legs.

“I must say, you look lovely in that uniform, Cecilia. And seamed stockings as well... very elegant.”

Cecilia curtsied, a hint of nervousness in his expression. “Mistress, I was hoping to speak freely about Miss Angela.”

Cathy looked intrigued, patting the bed beside her. “Come, sit.”

He carefully sat facing her and, in a low voice, recounted the events of the previous day - Angela’s humiliating demands, Diane’s reluctant participation, and her ominous “something worse” warning. The fear in his voice was obvious.

Cathy listened patiently, her expression thoughtful. After a pause, she smiled gently and said, “no need to worry about that, Cecilia. Today, you’ll be helping out at the Green’s house for book club.”

Cecilia nodded, though his heart sank at the idea of another public display. Cathy, noticing his anxiety, added, “And I will speak to Angela.”

Cecilia gave a small, relieved smile. “Thank you, Mistress.”

He stood up to collect the scattered laundry from the floor, bending at the waist. Cathy smirked, watching him. “It’s not only men those legs attract,” she teased. Cathy casually swung her legs over the edge of the bed, “You have me feeling tense now Cici, can you help me with that…”

Cecilia smiled, gave a nod, knowing exactly what she meant he knelt before her.

The walk to Mrs. Green’s house took him through the village. Head held high, he wore his new formal maid uniform with a sense of pride, and thankful it drew far less attention than the shop worker’s uniform.

Cathy telephoned Angela during her drive to work, said Cecilia was upset, scared by the talk of real men, “I heard him crying last night in his room Angela.” 

“You need to get past this Cathy, by now he should be kneeling for your bull.”

“There is no timetable for that, and I will decide when and where, not you.”

Angela said Cathy was being too soft, she had taken him so far now it is time to get Cecilia sucking cocks, “I was trying to help you both Cathy.”

“He is not ready.”

“You think he will volunteer? If you are waiting for that he never will be ready to suck cocks. Why not send your maid over to me tomorrow and I’ll send you a cock sucking sissy back. You can even blame cruel bitch Angela for turning him into a cock sucker.”

“Cecilia is mine to do with as I wish Angela” Cathy laughed to lighten the tension between them “tunnel…” Cathy lied, ended the call, replayed the conversation, leaving her even angrier at Angelas attempted interference. 

Cathy had calmed by the time she arrived home, made positive comments on his new uniform and saying he must be tired after two busy days “go change while I shower then we can go out for dinner.”

18 - La Trattoria

Cecilia waited until they were nearing the bistro before speaking about Angela. “Thank you, Cathy, for saving me from Angela.”

Cathy glanced at him briefly, an amused smile playing on her lips. “Saving you… what did you think Angela would do exactly?”

Feeling a mix of embarrassment and relief, Cecilia hesitated “I thought she push things further make me give a blow job…”

Cathy chuckled, her eyes sparkling with amusement. “Blow job? You’re not ready. When you are I’ll be the one to take you there, not Angela. If anyone other than me tries anything inappropriate, you are to refuse. Do you understand?” Cathy reached into the glove compartment and took out a pocket size can of mace. “Use this as a last resort.”

Cecilia nodded, feeling a surge of relief. “Yes, thank you Mistress.”

“Mistress… are you in uniform?"”

“At times like this Thank you Cathy is not enough.” 

They both laughed. 

The La Trattoria was busy for a week night but Cathy had booked the booth they had on that first night when she offered Peter a crossdressing lifeline. “You were so embarrassed last time we shared this table.” She teased, then said she was in the mood for wine as they browsed the menu.

“I can drive us home Cathy.”

She was about to reprimand him for keeping his divers license secret when she heard her name spoken. Joan, one of the women Cecilia knew from book club, and a man waved. 

Cathy acted casual and invited them to join them Cecilia sensed Cathys embarrassment at being discovered socialising with her maid. Joan looked oddly at Cecilia, and enjoying his mistresses embarrassment, Cecilia smiled innocently. He said “how nice to see you for the second time today Mrs Smithers.

“I was uncertain for a moment” Joan said with a rising infliction to encourage explanation. 

“Outside of work there is no need for you to be formal with Joan and Maurice, Cecilia.” Cathy smiled kindly. 

That moment Joan recognised that, beside her house and money, Cathy had inherited her grandmother's skill of quietly managing social dynamics with irresistible precision.

During the evening Joan and Cecilia happened to be in the rest room at the same time. Joan expressed surprise at how casually Cecilia acted around Cathy “I mean she is usually so strict with you, I am surprised you have lasted this long Cecilia.”

Without Cathy to boost his confidence Cecilia automatically slipped back into maid role, "Cathy has set clear rules for how I am to conduct myself when I am on duty and when I am off duty, Mrs. Smithers. I like it that way." 

Back home Cathy relived the events of the evening as she showered, relived the feeling when the Smithers ‘caught’ her socialising with Cecilia - she had not had that feeling since her mother saw her holding hands with a boy for the first time. Cathy slipped on a bathrobe “why are you still here?” She teased, out of uniform Cecilia was pretending to be tidying while he waited to massage her feet and more. 

The wine had left Cathy wanting more, much more, taking the chastity key from a drawer she said “do you remember the safe word?” 

“Uncle”

Cathy smiled, nodded, handed him the key, “slip your panties off  then lay on the bed.” Lifting the hem of his dress she straddled him revealing his half hard cock. Positioning his soft cock against his stomach she lightly rubbed herself back and forth imagining what that would feel like inside her.

Meanwhile Cecilia stayed silent, 80% of him wanted sex, 20% of him knew sex would leave him one step away from cuckolding.

“Are you trying to get hard like a real man?” Cathy teased, her arousal already reducing friction between them. “see if you can get hard for your mistress.” She  raised herself, slipped a hand between her legs, took his cock in hand and teasingly rubbed the end of his cock against her. 

She lowered herself enough for him to enter her a fraction, her self restraint lessened with each millimetre of penetration. Cathy had not had sex since Jim, and never anything Cecilia sized. She was beyond stopping, her breath shortened and she leant forward supporting her body weight on her hands, As Cecilia pushed with his hips, Cathy pulled up, took back control, “stop that… stay still.” Her throat tightened, her lower back tingled, lust battled willpower until. Lust won and she let pleasure sweep over her as. Sex rarely brought her to orgasam, but Cecilia had. That he was not spent despite time in chastity boded well! 

Cathy relaxed her thigh muscles and before she realised what was happening Cecilia, like some sex-ninja-maid, flipped her into the missionary position and was thrusting with a slow determination. While ‘uncle’ waited on the tip of her tongue Cathy felt her body beginning to respond to his trusts. Her second orgasam came over her like a  tsunami, gasping for air she felt him finally cum.

They sat on opposite sides of the bed, neither wanting to be the first to speak, an awkward silence settled between them. Cathy glanced over her shoulder at Cecilia and bit her lip. This hadn’t just been about sex but something deeper. 

Something neither of them expected. 

Previously she had always been the one in control, the one taking pleasure from his uncertainty. Now that same uncertainty prevented her from reaching out, holding him, saying how much he meant to her.

in his submissiveness seen him as her obedient sissy maid, someone to tease, control. Yet now, all she wanted was to reach out, hold him, and say how much he meant to her.

Likewise Cecilia’s usual composure was gone, replaced by dread of what comes next. He had read enough stories to know how these things turned out for sissy maids like him - relegated to the sidelines, a cuckold in someone else’s life. The thought hurt like a knife twisted in his stomach. Overcome, he choked back a sob and made for the door.

Cathy rose quickly, reaching out to place a steadying hand on his shoulder. “Cecilia, what’s wrong?”

He took a shaky breath, his voice barely a whisper. “I… I know what happens next, Cathy. I love you, but… I don’t want to be your cuckold…”

“No,” she cut in, her voice soft yet resolute. “That’s not what this is about. I thought once that maybe I’d want someone else - a man who wasn’t you. But I don’t feel that way anymore, I haven’t for a long time.” She paused, letting the weight of her words settle. “I love you as well, Cecilia. Not just as my maid, not just in uniform, but as you are right now. I don’t want anyone else.”

Cecilia blinked, trying to absorb her words, a mix of disbelief and relief in his eyes. “You… you mean that?”

“Every word,” Cathy said, taking his hands in hers. “I want us to be together - not just as mistress and maid but as partners. I want all of you.”

“I want that too… but how will we balance it?” he whispered. Slowly, Cecilia’s tears subsided. For so long, he had assumed his worth to Cathy came solely from being submissive, from being her perfect sissy maid. The idea of being loved, truly loved, had always felt out of reach. “I still want to be your maid.”

Cathy’s eyes softened. “We can have both. When you’re in uniform, you’ll be my maid, and nothing will change. But when you take it off, we’ll just be us - two people in love.”

A smile broke across his face. “I really want that.”

Cathy squeezed his hands, pulling him into a warm embrace. “Then that’s settled,” she murmured against his hair.

19 - The Lounge Bar

As much as Cathy longed for Cecilia to be in her bed every night she realised that would threaten his role as her maid. On ‘work days,’ no matter how needy she felt, Cathy acted like a real tyrant, criticising her maid without cause, inventing fault where none existed. Cecilia played his part with renewed enthusiasm and became ever more subservient. The new routine worked perfectly, she kept Cecilia in chastity releasing him only when ‘off-duty.’ At Cathys suggestion they purchased panties described as ‘gaff’ style for off-duty days.

***

From time to time Cathy and Cecilia would kick back and enjoy a night out. 

They made no effort to conceal their out of uniform relationship from villagers and neighbours. 

They made no effort to reveal it either, visitors became accustomed to being randomly greeted by Cathy or Cecilia randomly dressed - in or out of uniform. There was little reaction to Cecilia becoming Cathys plus one at dinners and fundraisers.  Gossip of the lesbians sprung up like a wildfire tearing through the community. And, like wildfire, gossip died down just as fast. 

Occasionally they would travel out of town, overnight hotel distance from home, far enough that Cecilias secret humiliations remained just that. On one such trip, they dressed to the nines in their hotel room - Cathy wore a sleek red figure hugging dress, and Cecilia, ever the chameleon, wore a daring black outfit that accentuated his slim, elegant frame. They both loved how movement revealed an eye-attracting amount of breasts on display. They headed out with excitement, ready to lose themselves in the city’s pulse.

A few cocktails and a couple of bars later, they ended up back in the hotel bar - a cozy, dimly lit lounge that felt both lively and intimate. The lonely businessmen occupied the barstools like pigeons on a railing watching for lunchtime crumbs. The bartender set their drinks on the table before moving. Cathy smiled barstoolwards, no one in particular, leaned close to Cecilia, her laughter bright and bubbling as they shared an inside joke about their evening so far.

Two men approached, slipping wedding bands into pockets, flashing confident smiles. The taller one, with dark hair and sharp cheekbones, threw Cathy a disarming grin.

“Mind if we join you ladies?” he asked smoothly, his gaze lingering on Cathy.

Cathy shot Cecilia a mischievous glance and smiled innocently. “Well, I guess we could use some company,” her voice playfully coy.

He said, sliding closer and giving Cecilia a bold once-over. “So, what brings you two out tonight?”

“Oh, just looking for a little excitement,” Cecilia answered, casting a flirtatious look back at Cathy’s companion, his voice light with a playful edge. The group laughed, shared stories, and flirted freely. Cathy let her eyes linger on her admirer’s every word, her laughter rich and a bit too warm. Cecilia, in response, leaned in closer to his admirer, flashing him a smile that made him lean even closer.

“So, what do you ladies like to go for fun?” Cathy’s companion asked, leaning just a bit too close, emboldened by the drinks.

“Oh, we’re just a couple of homies at heart,” Cathy purred, casting a teasing look over to Cecilia. “Snuggled up in bed early most nights.”

As the evening wore on, the men grew bolder. The bar began to empty, the laughter grew softer, one of the men glanced at his friend and asked, “What are you two doing tomorrow? Or later tonight - maybe we could hit the minibar?”

“Minibar sounds interesting…” Cathy gave them an innocent smile, biting her lip as she held back a grin. “I’d need to ask my boyfriend if he’d be okay with that first.”

Both men blinked in surprise, momentarily thrown. The taller one frowned slightly but tried to play it cool. “Oh, well, he doesn’t have to know, right?”

“He might already know…” Cathy smiled wider. “let me check with him…” She wore an ear to ear smirk while turning to Cecilia. “What do you think, Peter? Should we make a date with them?”

There was a second of pure, stunned silence as the men processed what they’d just heard. They glanced between Cathy and Cecilia, the dots finally connecting. Their faces shifted from confusion to sudden, wide-eyed realisation, their interest dissolving in an instant. The men stammered out something incoherent before they headed toward the safety of the elevator. 

The second they were out of earshot, Cathy and Cecilia burst into laughter, clutching their stomachs as they struggled to breathe. “Oh, did you see the look on his face?” Cathy gasped, wiping tears from her eyes.

“When you called me Peter, priceless.”

20 - Weekend Guests

A year had passed since Cathy and Cecilia had redefined their relationship, they were preparing for weekend guests - Julie and boyfriend Adrian Hawkes. Cathy and Cecilia had decided it was time to invite them. Although, as coworkers, Cathy saw Julie workdays, but too long had passed since Julies last visit to the house.

Cecilia felt nervous at meeting Adrian for the first time. And so much time had passed since their last meeting it would feel like meeting Julie for the first time as well. All that aside, he was excited to see Julie, to see for himself if she looked as pregnant as Cathy claimed.

Julie pre-warned Adrian did not need to know about Cecilia’s man-secret. And she pre-warned Adrian about Cathy and Cecilias unusual living arrangement which served to make Adrian keener to meet the odd couple. He was not disappointed when a maid opened the door to them. 

“Hello Miss Julie.”

“Hello Cecilia, this is Adrian Hawkes.”

“Nice to meet you Mr. Hawkes.”

Cathy had a playful glint in her eye. “Come on, Julie. Let me show you where I keep my maid while Cecilia shows Adrian to your room.”

Julie opened the door, her eyes scanning the uniforms hanging in the closet. “Wow,” she said softly, her voice  carrying a hint of disbelief. “So many uniforms... and where are her civilian clothes.” Julie smirked “is that what you call them? Civilian clothes?”

Cathy hid her annoyance at Julies teasing and smile-blushed “you are such a tease… in our bedroom.”

Cecilia made coffee for everyone before slipping away to change into casual skirt and blouse similar, but not too similar, to Cathy’s clothes. As they chatted he noticed the glow of happiness Julie wore, noticed her hand rested frequently on her belly. 

Adrian helped Julie even when there was no need, would gently take her elbow as they walked, he seemed utterly devoted to her. Cecilia liked how Julie’s face lit up whenever she looked at Adrian. 

Maid like attention to the small things meant Cecilia noticed little things like that. It made him happy to see her like this, but also made him feel a pang of nostalgia for the life they had once shared. He hadn’t loved Julie the way he loved Cathy, but he had cared for her deeply. 

He found a moment alone with Julie in the kitchen. She leaned close "you look well, Peter," she whispered, teasingly using the name he no longer identified with.

He smiled at their reflection in the window over the sink.

Julie’s eyes softened with understanding, and she nodded. "Cecilia," she said, her voice gentle. "I’m happy for you. You seem... content. More yourself."

He felt a warmth spread through him. "I am," he admitted, then looked back up at her, smiling. "And I’m happy for you. You and Adrian... you seem perfect together."

Julie’s hand fluttered instinctively to her belly, and she smiled, a little shyly.

Their moment was brief, but it still felt like closure.

Saturday evening the four left for a meal out at La Trattoria. Julie took in every detail of the look Cathy had created for her Cecilia; emerald green wrap dress skimming his figure in soft, elegant folds, understated yet striking, was complemented by classic matching heels. Sheer, seamed stockings a nod to timeless sophistication. His jewellery was discreet - a hint of gold glinting at his ears and a slender bracelet on one wrist, catching the light as he moved. Released from its earlier pony his dark hair was cut in a salon-sharp, blunt bob that framed his face perfectly, giving him an air of quiet confidence. She watched the way Cecilia smiled when Cathy tucked an unruly lock of hair behind his left ear from time to time.

Adrian also discreetly watched the strange couple, once Julie noticed his gaze settle on the hint of cleavage the green dress revealed as Cecilia leant forward.

The meal was relaxed, filled with light conversation. Adrian proved to be charming company, and Julie, glowing from her pregnancy, seemed at ease.

"Pass the wine, Cici," Cathy accidentally let slip.

Julie’s eyes sparkled with amusement, "Cici?" she repeated with a grin, arching an eyebrow. 

Cathy took a fork of pasta, Cecilia sniggered and matched her blush as he poured wine.

***

Sunday morning, Cecilia woke early, slipping out of bed without disturbing Cathy. He dressed casually - skinny jeans and tee, he went downstairs to prepare breakfast. The smell of freshly brewed coffee filled the air as he laid out a buffet breakfast croissants, cereal, fruit, yogurt.

Cathy, Julie, Adrian joined Cecilia, Julie, wearing dressing gown, rubbed her belly with a satisfied smile. "This looks lovely, Cecilia," she said, her tone warm.

Cecilia blushed slightly, pleased with the praise. "Thank you, Julie."

There was an ease to the morning that had not existed the day before - Cathy seemed more relaxed. Adrian seemed comfortable, made jokes and teased Julie as they all ate. Cecilia, distracted by the ease of the morning, made a slip of his own "more coffee Kitty?"

"More coffee Kitty?” Julie parroted. The table fell silent for a moment, Cathy’s eyes met Cecilia’s, a faint blush colouring her cheeks. 

Julie, quick as ever, smirked slightly as she raised an eyebrow. “Kitty that short for Kitten?" her voice teasing

Cecilia flushed crimson, realising his mistake. "I... I meant Cathy, I was confused by seeing that cat walk past " he lied.

“Smitten-Kitten?” Julie chuckled softly, shaking her head. "Oh, I love that," she teased, her eyes sparkling. “How sweet."

The sun was just beginning to dip toward the horizon when Julie and Adrian packed their bags. Julie, her pregnancy making her movements a little slower, hugged Cathy and Cecilia goodbye at the front door.

"Thank you both for such a lovely weekend," she said, her voice filled with genuine affection. "We’ll have to do this again soon."

Adrian cheek-kissed Cathy and Cecilia. "Yeah, it was great. Next time, maybe we’ll host you," he offered with a smile.

As the car pulled away from the house, Julie waved from the passenger seat. The weekend had gone much better than he had expected. Cecilia waved one last time as the car disappeared from view and turned to Cathy. She looked at him with a glint in her eye, one eyebrow raised in that way she always did when she was about to give him orders. "Well," Cathy began, her tone slipping effortlessly back into its usual commanding edge. "That was nice. But now, it's time to get back to work."

Cecilia felt a familiar thrill run through him. He knew what was coming.

“Get changed Cecilia, the guest room awaits," Cathy continued, her voice crisp and authoritative. “First I want you to clear the tea things and make sure the kitchen is spotless. After that, I’ll expect my coffee to be served in the lounge room."

Cecilia's smile widened as she spoke, he kissed her briefly on the lips. It was a light, teasing kiss, just enough to make Cathy narrow her eyes at him. “Yes, my little smitten kitten" he said with a cheeky grin.

Cathy’s eyes flashed with both amusement and mock severity. “You will pay for your insolence maid, get into uniform” she said, the edginess to her voice softened by the smirk on her lips.