Chapter 1: Introduction
Jason sipped wine from a glass as he goes through his email he has set up for his peculiar job advertisement. He had put up an unusual job posting a few days ago. He was looking for someone that would fit his specific needs. He scanned through his emails, deleting most of them without a second glance. The usual applicants were either too young, too old, or too boring.
He sat back on the lush, leather sofa in his penthouse and let out a sigh. The view of the cityscape was breathtaking, but it was just another reminder of his solitary life. His wealth had afforded him a life of luxury, but it had also taken a toll on his ability to connect with others on a deeper level.
His last relationship had ended over a year ago, and since then, he had been living in a self-imposed exile, surrounded by material wealth but devoid of emotional fulfillment.
Jason's eyes lingered on one email, the subject line reading "Unusual Job Application - Just What You've Been Looking For." He raised an eyebrow and clicked it open. The applicant's name was Jena, but she had included a photo of herself, which was unusual.
Victoria was striking, with dark hair, bright blue eyes, and a confident smile, she had small bulge hiding behind her skirt, she's was actually a he, either staring their transition or a crossdresser.
Jena's email was short and to the point, but it was her photo that caught Jason's attention. She was sitting in a coffee shop, legs crossed, with a laptop open and a cup of coffee beside her. Her eyes looked directly into the camera, as if daring him to dismiss her.
Jason clicked on the attachment, a video file. He leaned back, watching as Jena spoke directly to him, her voice low and sultry.
"Hey, Jason. I hope this video finds you well. I'm Jena, and I'm applying for your... unique job. I'm a crossdresser hoping to transition into a woman with the money I earn," she paused, letting that sink in before continuing, "and I think I have just what you're looking for."
Jason raised an eyebrow, intrigued by her boldness. He leaned forward, his wine glass forgotten on the coffee table.
"I'm all ears," he said, his voice a low rumble.
Jena smiled, her eyes sparkling with mischief. "Well, Jason, I'm not just a pretty face. I'm intelligent, witty, and I have a knack for making people feel comfortable in their own skin. I think I could be just the companion you've been searching for," she says over the video.
"Very well I will send your information to my driver he will be in touch with you to set up an appointment for tomorrow morning," Jason replied.
Jena's smile widened, revealing perfect teeth. "See you soon, Jason."
Jason closed the laptop, his mind racing. He had to admit, Jena was intriguing. She was bold, confident, and even a bit mysterious. He liked that. He liked that a lot.
The next morning, Jena stood outside Jason's penthouse, butterflies dancing in her stomach. She had dressed carefully, wanting to make a good impression. She was wearing a black pencil skirt that hugged her curves just right, a white silk blouse that showed off her her flat chest, she hoped to buy implants with the money she earns here.
Her hair was pulled back into a neat bun, and she had her makeup done just right, enough to highlight her features but not enough to look like she was trying too hard. She took a deep breath and knocked on the door.
A few moments later, the door opened, and there he was. Jason Monroe. He was even more handsome in person, with his dark hair, sharp jawline, and piercing blue eyes. He was wearing a suit that looked like it was tailored just for him, and he smelled like expensive cologne. He held the door open and stepped aside to let her in.
"You're right on time, Jena," he said, his voice low and smooth. "Come in."
Jena stepped inside, her heels clicking against the polished concrete floor. She took a moment to take in her surroundings. The penthouse was even more impressive in person, with its floor-to-ceiling windows offering a breathtaking view of the city. The interior was a mix of sleek, modern design and opulent comfort, with high-end furniture and artwork adorning the walls.
Jason led her to the living room, where a coffee table was set up with a carafe of coffee and two cups.
He gestured for her to sit down and poured her a cup. "Black, right?" he asked, remembering the information she had provided in her email.
Jena nodded, taking the cup from him. "Yes, thank you. You have a beautiful home, Jason."
He smiled, a genuine smile that crinkled the corners of his eyes. "Thank you. I like to think so." He sat down across from her, his own cup in hand. "So, Jena, tell me more about yourself. What made you want to apply for this... unique job?"
Jena took a sip of her coffee, buying herself a moment to think.
She had prepared for this question, but she still wanted to choose her words carefully.
"Well, Jason, I'm 19 I've always been a bit of an outsider. I never fit in with the typical crowd, and as you can see not afford to show people what I am, crossdressing is my life but with the money I earn here I hope to transition into a woman,"
she said, her voice steady. "I've always been drawn to the finer things in life, the art, the culture, the beautiful spaces. But I've also always been drawn to the people who create those things, the ones who push boundaries and challenge the status quo. You're one of those people, Jason. And I think we could learn a lot from each other."
Jason's eyes narrowed slightly, a look of intrigue crossing his face. "You're direct, I like that. But tell me, what makes you think you're the right fit for this job," he asks , raising an eyebrow.
Jena leans forward in her chair, her voice low and confident, "Well, I'm smart, resourceful, and I have a knack for making people feel comfortable in their own skin. I'm not here to judge or be judged. I'm here to provide companionship, to listen, and to be present. I think my unique perspective can bring a fresh dynamic to your life, Jason."
Jason takes a sip of his coffee, watching her over the rim of his cup. "Unique perspective, huh? I like that. But you should know, this job isn't just about companionship.
It requires a level of... intimacy. Are you prepared for that?" Jason asked, his gaze intense.
Jena took a deep breath, her heart pounding in her chest. She had expected this question, but it still made her nervous. "I understand the requirements of the job, Jason. And yes, I'm prepared for that. I'm not just looking for a sugar daddy or a wealthy benefactor. I want to be your partner, in every sense of the word. I want to learn from you, grow with you, and explore new aspects of myself with you."
Jason nodded, a small smile playing on his lips. "I appreciate your honesty, Jena. But you should be know that in my sex life I act as the master, and I would expect you to obey my commands, do you understand," Jason asks, his voice firm but not aggressive.
Jena nods slowly, a glint of excitement in her eyes. "Yes, I understand. I'm not new to this, Jason. I've explored my submissive side in the past, and I find it... liberating. I'm ready to commit to that dynamic with you."
Jason leans back in his chair, a smirk playing on his lips. "Good. Because I have plans for you, Jena. Plans that will push your boundaries and test your limits."
Jena's breath hitches slightly, but she maintains eye contact with Jason.
"Now, tell me what would you like your monthly salary or be while living here," Jason asks, leaning back in his chair, his gaze never leaving hers.
Jena takes a moment to think. "I was thinking something around fifteen thousand a month, plus room and board. I understand that the job comes with certain... perks, but I also want to make sure we have a solid understanding of the financial aspects as well," she says, her voice steady.
Jason nods, a hint of approval in his expression. "Fair enough. I was thinking along the same lines. This is the contact to sign, read over it," Jason said, handing over a contract to Jena.
She scanned it quickly, her eyes darting over the clauses. It was a standard non-disclosure agreement, with a few additional clauses outlining the nature of their relationship and the terms of her employment. She looked up at Jason, her eyes narrowing slightly.
"This says that I'm not allowed to discuss our relationship with anyone, not even my closest friends. Is that really necessary?" she asked, her voice cautious.
Jason nodded, his expression serious. "You may talk about our relationship, that we are seeing each other, just not discuss what goes on behind the doors, understand," Jason said, his voice firm.
Jena nodded, understanding the importance of the clause. She took a pen from her purse and signed the contract. She handed it back to Jason, who did the same and placed it in a drawer.
"Now that the formalities are out of the way, how about a tour of the penthouse?" Jason suggested, standing up and extending his hand to Jena.
She took his hand, feeling a spark at his touch. "I'd like that," she said, a small smile playing on her lips.
Jason led her through the penthouse, showing her the various rooms and amenities.
The tour started in the kitchen, where a state-of-the-art espresso machine and high-end appliances gleamed under the soft lighting.
"I cook quite a lot, prefer it over going out," he says , watching as Jena ran her fingers along the countertop.
"I love to cook too. It's therapeutic for me," she replied, her eyes scanning the kitchen.
They moved on to the dining area, where a large glass table reflected the city lights.
"I've had many important meetings here, but it's also where I enjoy a quiet dinner alone sometimes," Jason said, his voice wistful.
Jena nodded, understanding the duality of his life.
Next, they walked through the home office, where shelves filled with books lined the walls.
"You read a lot?" Jena asked, her eyes widening as she scanned the titles.
"I find it's important to be well-read," Jason replied, his fingers trailing over the spines of his favorite books. "It helps keep the mind sharp."
Jena nodded, her gaze lingering on the classic literature section. "I couldn't agree more. I've always loved getting lost in a good book."
Jason smiled, a genuine warmth in his eyes. "Well, you're welcome to borrow anything you'd like."
They continued the tour, passing by a small gymnasium and a home theater before arriving at a door that Jason paused in front of.
"This is my personal space," he said, his voice softening. "It's where I go to... unwind."
Jena raised an eyebrow, curiosity piquing. "And what does that involve?"
Jason's lips curled into a small smile. "Come in, and I'll show you." He opened the door, revealing a dimly lit room filled with an array of objects that sent a shiver of anticipation down Jena's spine. There were whips, floggers, cuffs, and other assorted instruments, all neatly displayed on the walls.
In the center of the room, a large wooden St. Andrew's cross stood tall, its leather-padded arms gleaming under the soft light. Jena's breath hitched, her eyes widening as she took it all in.
"This is... a lot," she said, her voice barely above a whisper.
Jason crossed his arms, a smirk playing on his lips. "You didn't think I was joking about the intimacy and pushing boundaries, did you?"
Jena shook her head, her heart pounding in her chest. "No, I didn't. But this...
it's more than I expected," Jena admitted, her eyes scanning the room once more before meeting Jason's gaze.
Jason chuckled, a low, sexy rumble that sent a shiver down Jena's spine. I like to keep my partners on their toes. And I have a feeling you'll enjoy the thrill of it all."
Jena took a deep breath, her body tingling with a mix of nervousness and excitement. "I think I will. But before we go any further, I need to ask...
what's your safe word?" Jena asked, her voice steady despite the flutter of nerves in her stomach. She knew better than to dive into a new dynamic without establishing a clear line of communication and boundaries.
Jason's eyes softened, and he nodded approvingly. "I don't have one, these toys and devices are for my submission toys, what is your safe word my dear,"
he asked, stepping closer to her, his voice a low rumble.
Jena's breath hitched slightly as he approached, but she held her ground. She thought for a moment before answering, "My safe word is... jade."
Jason smiled, his eyes never leaving hers. "Jade it is. And you can use it anytime you need to, alright? I want you to feel safe and comfortable here, Jena. Our relationship is built on trust and communication," he said, his voice firm but gentle.
Jena nodded, feeling a sense of relief wash over her. "Thank you, Jason.
That means a lot to me," Jena said, her voice sincere. She took a moment to look around the room again, her eyes lingering on the St. Andrew's cross. "So, what's next?" she asked, her curiosity getting the better of her.
Jason stepped closer, his hand gently cupping her cheek. "Next, your first task," he says walking up to a draw and opening it pulling out a pink cock cage.
"Put your cock in this," Jason said, handing her the cock cage.
Jena hesitated for a moment, feeling a thrill of anticipation mixed with a hint of nervousness. She had prepared for this, but the reality of it was still a bit overwhelming. She quickly undid her skirt and her underwear, revealing her cock to Jason.
"Hurry up, I don't have all day," Jason said, his voice impatient.
Jena quickly slipped her cock into the cage, the cold metal sending a shiver down her spine. She struggled to fasten it properly, her fingers fumbling with the lock.
"I can see why you want to transition, it's one of the smallest cocks I have ever seen, only a inch," Jason said, his voice dripping with disappointment.
He took the cage from her and locked it securely, ensuring it was tight enough to restrict blood flow.
Jena winced slightly, the sensation new and uncomfortable. "You'll get used to it," Jason assured her, his voice gentle but firm.
He took a step back, his eyes scanning her body, taking in every detail. "Now, the rules. You're not to touch yourself without permission. No orgasms unless I give you one. Understand?"
Jena nodded, her eyes wide as she tried to process the sudden rush of information.
"Now, for your next assignment, I want you to strip," Jason commanded, his voice low and steady.
Jena hesitated for a moment, her heart pounding in her chest. But she knew better than to disobey him, especially this early in their arrangement. She slowly began to remove her clothes, her hands shaking slightly as she unbuttoned her blouse and slipped it off her shoulders.
Jason watched her intently, his eyes roaming over her body as she exposed more and more skin. He could see the goosebumps rising on her flesh, the slight tremble in her hands as she unzipped her skirt and let it fall to the floor.
"Leave the heels on," Jason instructed as Jena stepped out of her skirt.
He liked the way the heels accentuated her calves, making her legs look even longer. He could see that she was self-conscious, her eyes flickering over his face as if seeking approval.
"Very good," he said, his voice softening. "Now, come here." He held out his hand, and Jena walked towards him, her skin prickling with awareness. He could smell her arousal mixed with her nervous sweat, a heady combination that made his cock stir in his pants.
He gripped her chin gently, tilting her head up so that she was looking him in the eyes. "You're doing great, Jena. Now you might think this disgusting what I ask, but remember you must obey me," he says looking at her face "Get on your knee," he commands.
Jena hesitates for a moment, but she quickly kneels in front of him, her heart pounding in her chest. She can feel the cold hardwood floor beneath her knees, the slight discomfort grounding her in reality.
Jason chuckles, a low rumble that sends shivers down Jena's spine. "Good girl. Now, I want you to take my belt off."
Jena's breath hitches as she reaches for his belt, her fingers trembling slightly as she unbuckles it. She can feel Jason's gaze on her, intense and heated, as she slowly pulls the belt from his pants.
He remains silent, allowing her to anticipate what's to come. The leather is smooth and cool in her hands, and she hesitates for a moment before looking up at him.
"What do you want me to do with it?" she asks, her voice barely above a whisper.
Jason's lips curl into a smirk, his eyes never leaving hers. "You'll find out soon enough," he replies, his voice low and teasing.
With a deep breath, Jena folds the belt in half and runs her fingers along the length, feeling the stiffness of the exposed metal.
She looks up at Jason, her eyes filled with a mix of fear and anticipation. He nods subtly, encouraging her to continue.
"Good girl," he praises, his voice a low rumble. "Now pull my cock out," he commands, his words leaving no room for doubt.
Jena swallows hard, her heart pounding in her chest. She's never done anything like this before, and the thought of it sends a mixture of fear and excitement coursing through her veins. But she knows that she must obey, that she must give in to his commands if she wants to understand the dynamics of their relationship.
She reaches for his belt, her fingers fumbling slightly as she unbuckles it and pulls it off. His pants are next, her heart hammering in her chest as she unbuttons them and slides them down his hips. His boxers follow, revealing his hard, throbbing cock.
It's larger than she expected, and she feels a sense of both apprehension and arousal. She takes a deep breath, steeling herself for what's to come.
"Go on, Jena. Take it in your hand," Jason commands, his voice steady and firm.
Jena tentatively reaches out, her fingers wrapping around the base of his shaft. It's warm and hard, pulsating with life under her touch. She looks up at him, seeking approval or guidance, but his expression is impassive.
"Now open your mouth wide for me,"
Jason instructs, his voice low and commanding.
Jena hesitates for a moment, her mind racing with a mix of uncertainty and excitement.
"Good girl, now for your first tasks you will drink my piss," Jason says, his voice authoritative and unyielding.
Jena's eyes widen in surprise, her hand still wrapped around Jason's cock. She had never done anything like this before, and the thought of it sends a shiver down her spine.
"I-I'm not sure if I can do that," Jena stammers, her voice barely above a whisper.
Jason's eyes narrow, and he takes a step back, his cock slipping from Jena's grasp.
"Do you want to back out now, Jena?" he asks, his voice devoid of emotion.
"This is my first test of your obedience and willingness to please me. If you can't handle this, then maybe this arrangement isn't for you." She knows that she's in uncharted territory, but she also knows that she's in this because she wants to explore, to push her boundaries.
"I... I can do this," she says, her voice firm despite the fear in her eyes.
Jason nods, a smirk playing on his lips.
Now, put your hands behind your back and keep your mouth open," he instructs.
Jena swallows hard, her heart racing as she interlinks her fingers behind her back. She parts her lips, her breath coming in short gasps as she waits for what's to come.
Jason steps closer, his hand wrapping around his cock and giving it a few firm strokes. He looks down at Jena, his eyes filled with a mix of dominance and desire. "You're doing great, Jena," he reassures her.
"Now, I want you to count to ten while I do this.
Jena nods, her eyes glued to Jason's cock. She can feel the anticipation building in her stomach, a mix of fear and excitement swirling within her.
"Yes, Jason," she manages to croak out.
Jason takes a step closer, his cock now inches away from her mouth. He releases his grip, allowing his stream of piss to flow directly into Jena's open mouth.
Jena's eyes water as the warm, bitter liquid fills her mouth. She swallows quickly, trying to keep up with the constant flow.
The taste is overwhelming, and she fights the instinct to gag. She focuses on the task, counting under her breath.
"One... Two... Three..."
Jason watches her intently, a sense of pride and satisfaction washing over him. She's handling this better than some of his previous subs. He can see the effort it's taking her, but she's doing it. She's giving in to his command, pushing her boundaries, and that's what he loves to see.
"Four... Five..."
Jena's eyes water more, and the bitterness seems to intensify.
She swallows again, forcing herself not to let any spill from her mouth. She's lost track of her count, but she knows she's not at ten yet.
"Six... Seven..." she manages to say, her voice strained.
Jason's stream starts to slow, and he places a hand on her head, gently caressing her hair. "Good girl," he praises, his voice soothing. "You're doing so well, Jena."
He gives her a few more seconds to swallow the last of his piss before stepping back. Jena sits back on her heels, her hands still behind her back.
"Good girl, how did you like the taste of my piss," Jason asks, his voice teasing.
Jena takes a moment to swallow the last of his piss, her eyes watering slightly. She looks up at him, her expression a mix of surprise and relief. I didn't think I'd be able to do that," she admits, her voice hoarse.
Jason smiles, his eyes softening as he looks down at her.
"You did beautifully, Jena. You've passed your first test."
He extends a hand to her, helping her up to her feet.
"Thank you, Jason," Jena says, her voice filled with gratitude.
She looks up at him, her eyes shining with unshed tears.
"I can't believe I did that," she says, her voice filled with amazement.
Jason smiles, tucking his cock back into his pants and fastening his belt. "Believe it, Jena. You're stronger than you think." He steps closer to her, his hand cupping her cheek. "You're doing so well, and I'm proud of you," he says softly.
Jena leans into his touch, her eyes fluttering closed for a moment. She can feel the warmth of his hand, the roughness of his palm against her smooth skin. She takes a deep breath, letting the moment sink in.
"You going to be the perfect pet, and I can see your tiny cock got hard in its cage, seems like you like being dominated," Jason murmurs, his thumb brushing against her cheek.
Jena's eyes flick open, her face flushing with embarrassment. She looks down, her eyes avoiding his gaze.
Jason chuckles, low and throaty. "Don't be shy, pet. I can see your body's response to my commands. That's a good thing, remember."
He steps back, his hand dropping from her face. "Now, let's get you settled in. I'll show you to your room."
Jena nods, her body still tingling from the aftermath of her task.
She follows Jason out of the playroom and back into the main living area. He leads her down a long hallway, past several closed doors, and finally stops in front of one of them.
"This will be your room," Jason says, pushing the door open.
Jena steps inside, immediately struck by the contrast between this room and the rest of the penthouse. While the rest of the apartment is sleek and modern, this room is cozy and inviting, with warm wooden furniture and soft lighting. A large bed with a plush comforter sits in the center of the room, and a small seating area with a loveseat and a coffee table is tucked into a corner.
A door to the right leads to what Jena assumes is an en-suite bathroom.
"It's beautiful," Jena says, her voice filled with genuine appreciation.
Jason smiles, leaning against the door frame. "I'm glad you like it. Make yourself at home, Jena. This is your space."
Jena nods, taking a few more steps into the room and looking around. I really appreciate it."
Jason watches her for a moment, his eyes reflecting a mix of pride and desire. "You've done well today, Jena. I'm impressed with your willingness to push your boundaries and your ability to follow my commands. Tomorrow we will try something much more extreme, only if you want," Jason says, his voice laced with a hint of warning.
Jena turns to face him, her eyes filled with a mix of trepidation and excitement. "I want to continue, Jason. I trust you, and I want to see where this journey takes me."
Jason smiles, a genuine warmth in his eyes. That's all I need to hear. Now, why don't you get settled in? I'll have some dinner sent up for you, and we can discuss your next assignment over a meal."
Jena nods, a sense of relief washing over her.
"Good, now get acquainted with your new room dinner will be at 6 sharp," Jason instructs, his voice firm yet gentle.
He turns to leave but pauses at the door, looking back at her.
"Oh, and Jena?"
She turns to face him, her eyes meeting his.
"Yes, Jason?"
He smiles, a mischievous glint in his eyes.
"Wear something... comfortable for dinner. We'll be discussing your next assignment in detail."
With that, he walks out, leaving Jena alone in her new room. She takes a deep breath, looking around at her surroundings, a sense of excitement and anticipation coursing through her veins.
She had never been in a situation like this before, but she was eager to explore, to push her boundaries, and to learn more about herself.
As she unpacks her few belongings into the dresser, she can't help but feel a sense of disbelief. She was actually here, living in Jason's penthouse, and she had already proven herself to him. She couldn't wait to see what the future held.
At six o'clock sharp, there's a soft knock at her door. She opens it to find a Jason.
"Dinner is ready," he says
, smiling at her.
Jena looks down at herself, suddenly self-conscious about her attire. She had put on a simple silk robe, thinking it would be comfortable for dinner. Now, she feels a bit underdressed compared to Jason's tailored suit.
"I hope you don't mind, I wasn't sure what to wear," Jena says, her voice soft.
Jason's eyes scan her from head to toe, taking in every detail of her appearance. "You look gorgeous, Jena," he replies, his voice a low rumble. "Come, let's eat."
He turns and walks down the hallway, leaving Jena to follow him.
She takes a deep breath, steeling herself for whatever might come next. She knows that this is just the beginning of her journey with Jason, and she's eager to see what the night has in store.
The dining area is set up with a small table for two, a silver candlestick holder with a flickering flame, and a bottle of wine chilling in an ice bucket. The scent of the dinner wafts through the air, making Jena's stomach rumble. She's surprised by how quickly she's become accustomed to the opulent lifestyle Jason provides.
The dining table is set with crystal glasses and silverware that gleams under the soft light of the candle. Jason pours her a glass of wine as she takes her seat across from him.
"To new beginnings," he says, raising his glass.
Jena clinks her glass against his, taking a small sip. The wine is rich and full-bodied, and she lets it linger on her tongue for a moment before swallowing. "It's delicious," she says, setting her glass down.
Jason smiles, his eyes reflecting the flickering candlelight.
It's a vintage from my private collection, reserved for special occasions."
Jena feels a flutter of excitement in her stomach. She's not used to this level of luxury, and the fact that Jason is sharing it with her makes her feel special. "It's exquisite," she says, her voice soft.
They eat in a comfortable silence, the clink of silverware against china the only soundtrack to their dinner. Jena savors every bite, the food rich and delicious, a far cry from the instant meals she's used to.
"Just relax and enjoy yourself," Jason says, noticing her tense shoulders.
Jena takes a deep breath, trying to let the tension leave her body. She takes another sip of wine, allowing the warmth to spread through her.
As they finish their meal, Jason leans back in his chair, his eyes never leaving Jena. "So, tell me, Jena, what's your dream job?" he asks, his voice low and conversational.
Jena swirls the remaining wine in her glass, contemplating the question. She's always wanted to be a graphic designer, but she knows that's not what Jason is looking for. She looks up at him, her eyes meeting his.
"You mean, outside of this arrangement?" she asks, a small smile playing on her lips.
Jason chuckles, his eyes crinkling at the corners. "Yes, outside of this. What do you want to do with your life, Jena? What's your passion?"
Jena takes a moment to think, her eyes reflecting the candlelight. "I've always been drawn to art and design. I love creating things, bringing ideas to life. My dream job would be to work as a graphic designer, creating visual content for brands, magazines, or even video games.
I've always been fascinated by the way art and design can evoke emotions and tell stories. Plus, it would allow me to express my creativity in a tangible way," Jena replies, her voice filled with passion.
Jason leans forward, intrigued by her response. "That's interesting. And why haven't you pursued it yet?" he asks, his voice gentle yet probing.
Jena sighs, taking a sip of her wine before answering. "Unfortunately, my financial situation hasn't allowed me to.
I've had to take on jobs that paid the bills but didn't fulfill me creatively. I've been working as a barista for the past year, saving up to maybe go back to school and get a degree in graphic design. But it's been slow going," Jena admits, her voice tinged with frustration.
Jason nods, understanding her situation all too well. He knows what it's like to have to put your dreams on hold to make ends meet. "Well, that's all going to change now," he says, his voice firm with resolve. "Outside of this agreement we have, I may be able to have you intern with one of my chief graphic designers," Jason says, leaning back in his chair and taking a sip of his wine.
Jena's eyes widen in surprise, and she nearly chokes on her wine. "Really? You'd do that for me?" she asks, her voice incredulous. "Consider it a perk of the job. I like to see potential in people, and I think you have a lot of it, Jena. Plus, it'll give us something to talk about outside of our... more intimate moments," he says, his eyes sparkling with mischief. "And if you wanting to transition too a.woman fully I have a doctor who would be willing to discuss it with you, what size implants would you like," Jason asks, his gaze intense.
Jena's eyes widen, her heart fluttering with a mixture of excitement and disbelief. I don't know. I never thought I'd have the opportunity to do that. Maybe a C cup? Or even a D? I always wanted to look more... feminine, but I kinda would like to look like a bimbo. Do you think 3500 cc breast implants would be too big," Jena admits, her voice soft.
She looks down at the table, a blush creeping up her cheeks. "Too big? Only if you want them to look natural. But if you're going for the bimbo look, 3500 cc might be too small. I could introduce you to a doctor who specializes in extreme augmentations. He's the best in the business, but he doesn't come cheap."
Jena's eyes widen, but she nods, a determined look in her eyes. "I want to look like a real bimbo, Jason. Big tits, blonde hair, and...
and maybe even some cosmetic work to enhance my features," Jena says, her voice filled with determination. "I want to look like the perfect bimbo doll you can mold and play with."
Jason's eyes darken with desire at her words, and he leans forward, his voice low and husky. "You're going to make me very happy, Jena. Very happy indeed."
He takes a sip of his wine, his eyes never leaving hers. "But first, let's discuss your next task. Are you ready for it?"
Jena takes a deep breath, her heart pounding in her chest. "Yes, I'm ready.
I want to know what you have in store for me," Jena replies, her voice steady despite the nervousness she feels inside. She takes a sip of wine, the liquid giving her something to do with her hands as she awaits his response.
Jason leans forward, his elbows resting on the table, his eyes locked on Jena. "Tomorrow I will set up my fuck machine, I have a horse size dildo you will suck and let fuck your ass,* he says looking at her face as she goes pale "You see I was cursed with a cock, bigger then that of a horse as you have already seen you will have to practice on that dildo before you can take my cock in your ass," Jason explains with a smirk, enjoying the look of shock on her face.
Jena's eyes wide with shock, her heart pounding in her chest. She had heard about fuck machines but never thought she would be expected to use one, let alone one with such a massive dildo. She takes a deep breath, trying to calm herself. I've never done anything like that before," she admits, her voice barely above a whisper.
Jason smiles, a smug look on his face. "Well, now is your chance to learn. And remember, your safe word is jade.
Use it if you need to. I want you to push your boundaries, Jena, but not to the point of breaking. Understood?" Jason's voice was firm but gentle, showing a rare display of concern.
Jena nodded, her heart pounding in her chest. She took another sip of wine, her hands trembling slightly. I trust you, Jason."
Jason smiled, a look of satisfaction crossing his face. Now, finish your wine, and I'll show you to your room.