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Chapter 87 by cutiepie183 cutiepie183

New sissy roles

Working it

Kyle pushed back his chair, his gaze steady as he regarded Logan and Matty. "Logan, today you’re going to be putting that maid uniform to good use and cleaning this entire house from top to bottom, I want it sparkling by the time I get home from work." he commanded with with authority. "Now Matty, you are going to need to go get changed, something cute and girly but professional should do the trick. You’re coming with me and I’m going to drop you in the city and you’re going to find a job by the time I finish work tonight." Kyle ordered Matty firmly. 

Matty smiled weakly. “Yes Master, I’ll go change now,” he agreed, forcing a smile to his lips.

Matty was nervous about the task Kyle had assigned him. He wasn’t particularly worried about finding a job – he was a smart guy, capable of handling various responsibilities. But the idea of wearing something “cute and girly,” as Kyle had instructed, filled him with anxiety as he hadn’t been in public since his sissy transformation.

He excused himself and left the room, his heart pounding in his chest. As he ascended the staircase, he thought about what he should wear.

As he searched through his wardrobe, he stumbled upon a sleek pink pencil skirt that would come to about mid thigh, a white crop top and a matching pink blazer. He finished the outfit with a pair of sensible heels, a small stylish handbag and touching up his makeup with a more paired back and simple look.

His reflection in the mirror was striking, with his feminine appearance blending effortlessly with the professional attire. Satisfied with his ensemble, Matty descended the stairs, eager to please his Master.

"Well, well," Kyle purred, his gaze fixed on Matty's transformed appearance. "You clean up quite nicely when you’re not trying to be a slut, don't you?"

Matty blushed, his gaze flitting nervously to Kyle. "Thank you," he stammered, his voice quivering slightly.

“Now let’s just take this off for today, and then you can get in the car so we can go, I don’t want to be late to work.” Kyle said as he swiftly unlocked and removed Matty’s collar.

Matty felt a rush of cold air hit his naked throat, and he gasped softly, his heart pounding in his chest.

His hands shook as he adjusted his clothing, the absence of the collar leaving him feeling strangely exposed.

"Alright," Kyle said briskly, his gaze steady as he gestured towards the door. "Let's get moving."

Matty followed Kyle into the car, happy to be riding in the passenger seat again. 

As they drove through the bustling streets of the city, Matty couldn't help but feel overwhelmed by the intensity of his situation. Everything was different now—his body, his identity, his purpose. It was exhilarating and terrifying in equal measure.

"Matty," Kyle said, his voice soft and deliberate. "Remember what I told you earlier. You're a strong, intelligent individual, and I have faith in your ability to succeed. Just stay focused, and don't let fear hold you back, oh and you only have until the end of the day, don’t forget that either."

Matty nodded, his gaze flicking nervously to Kyle.

"I won't let you down," he promised, his voice steadying as he tried to muster up the courage while getting out of the car now they had reached the city centre.

Kyle smiled, his gaze steady as he patted Matty on the shoulder. "I'm sure you’ll do fine," he answered, his voice confident and reassuring.

"Just go in there with confidence, and you'll land a position."

Matty nodded, his gaze flitting nervously to Kyle. "Okay," he whispered, his voice shaking slightly. "I'll try my best." "That's the spirit!" he encouraged, his voice enthusiastic and optimistic. "Now remember, the clock is ticking! So don't waste any time."

Matty took a deep breath, he turned and walked away, down the streets towards a large, busy office building. He figured someone in this massive corporate tower of million dollar businesses must be hiring so it seemed the logical place to start his search.

Walking confidently through the entrance lobby, his eyes scanned the directory for available companies that might provide a suitable opportunity. He spotted a few promising options and chose one called 'TechGenius Corp', hoping that it specialized in software development or web design. Those were fields where he could leverage his education and skills.

Matty approached the receptionist desk with a charming smile and friendly demeanor. "Hi," he greeted politely, his voice bright and cheerful.

"My name is Matty, and I'm looking for a job. Any openings at TechGenius Corp?"

The receptionist eyed him curiously, her gaze flicking between Matty and the computer screen. "I'm sorry," she replied, her voice clipped and impersonal. "We're not currently hiring secretaries or assistants."

Matty's heart sank, his gaze flitting nervously to the floor. "Oh," he murmured, his voice quavering slightly. "I see.

What about positions related to programming or web design?" Matty asked, his voice wavering slightly. "I do have experience in those areas."

The receptionist raised an eyebrow, her gaze flicking skeptically between Matty and the computer screen. "I’m sorry, you’re just not what we’re looking for in those departments right now, good luck with your job search though.” The receptionist answered dismissively before answering the phone and ignoring Matty.

Feeling defeated, Matty slumped against the wall near the elevator bank.

He didn't want to face Kyle empty-handed, and he desperately needed to find a job quickly. As he pondered his next steps, he noticed a man approaching the elevators. He wore an expensive looking business suit and Matty recognised his name badge as one of the other businesses listed in the directory downstairs, a large corporate law firm. 

The man caught sight of Matty standing alone, looking downcast and sad. Feeling sympathy for the young woman, he decided to approach her.

"Hello," Matty heard the man say. "May I offer some assistance?"

Matty looked up, surprised at the interruption. "Oh, hi," he replied, his voice hesitant and shy. "I'm just looking for a job, but I haven't had much luck so far."

The man smiled, his gaze steady as he sized Matty up.

"I'm James," he introduced himself, his voice warm and welcoming. "I work for a law firm upstairs. As luck would have it we are actually looking for a new assistant office manager right now. The role would actually be part office manager work and partly my personal secretary. Would you be interested in that kind of work?"

James asked, his eyes sparkling with curiosity.

Matty blinked, his gaze flicking nervously to the ground. "Yes," he murmured, his voice quaking slightly. "I'd definitely be interested."

James nodded, his gaze steady as he studied Matty carefully. "Well, I suppose we could schedule an interview for tomorrow," he offered, his voice hopeful and encouraging. "How does that sound?"

Matty smiled widely, his gaze flitting nervously to James. "Is there any chance we could do it today?" he replied, his voice hopeful and excited.

James considered the request, his gaze steady as he studied Matty. "Well, I suppose we could squeeze in a quick meeting if you're free," he replied, his voice thoughtful and accommodating. "Would you like to join me in my office?"

Matty nodded, his gaze flitting nervously to the elevator doors. "Yes, thank you," he whispered, his voice cracking slightly as he joined James in the elevator.

"I really appreciate your kindness."

James patted Matty affectionately on the shoulder. "It's no problem," he replied, his voice gentle and caring. "I just hate seeing someone so talented struggling to find work. Besides, I'm always looking for talented and passionate staff to join my team."

Matty smiled, his gaze flitting nervously to the elevator doors. "I'm glad I met you," he replied, his voice soft and grateful.

As the elevator stopped at the building’s penthouse, Matty followed James into his stunning high end offices.

The atmosphere was refined and sophisticated, with modern art adorning the walls and plush leather furniture positioned throughout the space. Matty couldn't help but be impressed by the lavish surroundings.

"Please, take a seat," James offered, his voice warm and inviting. "Let's begin our interview."

Matty nodded, his gaze flitting nervously to the plush armchair across from him. "Thank you," he murmured, his voice soft and appreciative.

Following quite a basic interview process Matty is offered the job with a generous salary and significant bonus if he can start immediately, he eagerly accepts and takes his starting paperwork to review and sign overnight before returning tomorrow to start his new job.

Matty smiles with relief at the prospect of having a job, he is excited to start working with James and his team. He looks at the time and realizes that he still has a few hours before Kyle finishes work. Deciding to spend some quality time alone, he decides to explore the city and shop for new work clothes.

Matty takes a deep breath, feeling rejuvenated and ready to take on the world. He exits the office building and begins walking towards the bustling city center. The streets are alive with people, and the aroma of street food fills the air. Matty can't help but feel invigorated by the energy of the city.

As he walks, Matty notices a trendy boutique on the corner of the street. The window display features stylish outfits, and he can't resist stepping inside to take a closer look.

By the time Kyle has finished work and come to collect Matty, he had purchased at least a dozen new power suits all balancing feminine cuteness with complete professionalism perfectly. 

He knew that this job required sophistication and elegance so he wanted to ensure that he made a lasting impression on James and his colleagues.

Matty exited the store, his arms laden with bags full of fashionable attire. He couldn't wait to show Kyle his purchases and bask in the praise and validation that he knew his master would shower upon him.

He headed back to where Kyle dropped him off to wait patiently for him to return, as he knew would be expected of him.

Is Master proud?

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