Doubling Down

Author's Note

To the readers who are returning from reading the first version of this erotic tale, you may recognize some of the events in this chapter! We are finally starting to tie things back together to the old version, but hopefully now things are much better explained and elaborated. I plan on continuing to keep things more "realistic" and seamless, the same way that I have been trying to so far.

Feedback on the story so far, as well as this version of this part of the story, would be greatly appreciated!

The old chapter, if you're interested: https://chyoa.com/chapter/Doubling-down.1341871

Jazmine entered the living room, her mind still reeling from the uncomfortable date with Kyle. She found Clea lounging on the couch, a glass of wine in hand and a serene smile on her face.

"Hey, Clea," Jazmine greeted, sinking into the armchair opposite her friend. "I need to talk about tonight."

Clea's eyes sparkled with curiosity as she set her wine glass down. "Of course, darling. Tell me all about it."

Taking a deep breath, Jazmine launched into a detailed account of the evening's events. She described how Kyle had been crude and pushy, making her uncomfortable with his advances. "And then, when we got back to his car, he just... I don't know, Clea. He wanted to..." Jazmine trailed off, unable to voice the explicit nature of Kyle's intentions.

Clea's response was surprisingly nonchalant. "Oh, sweetheart, boys will be boys," she said, waving a dismissive hand. "You're just getting used to this whole dating thing. It's perfectly normal to feel a little awkward at first."

"But Clea," Jazmine protested, her frustration bubbling to the surface. "I'm not like other girls. I'm not even a girl! This whole thing is so messed up. I struggled to even kiss him, and he just kept pushing and pushing..."

Clea's smile remained fixed, her tone unwaveringly positive. "Darling, you're doing so well. Kyle is a catch, and you're lucky to have his attention. Just relax and enjoy the ride. Everything will fall into place, I promise."

Jazmine's heart sank at Clea's words. She had hoped for understanding and support, but instead, she felt dismissed and invalidated. Swallowing her disappointment, she **** a smile and nodded along with Clea's reassurances, all the while struggling to suppress the turmoil raging inside her.

"Jazmine, darling, you're doing so well," Clea cooed, her voice dripping with encouragement. "Kyle is absolutely smitten with you. Can't you see how much he adores you?"

Jazmine fidgeted nervously in her seat, her mind still reeling from the uncomfortable encounter with Kyle. "But Clea, I struggled to even kiss him," she confessed, her voice barely above a whisper. "It just felt... wrong, you know?"

Clea's expression remained unwaveringly cheerful, her tone soothing and persuasive. "Oh, sweetie, it's completely normal to feel a little nervous on a first date," she reassured. "But you're a natural beauty, Jazmine. Kyle couldn't keep his eyes off you. You're irresistible."

Despite Clea's attempts to lift her spirits, Jazmine couldn't shake the nagging sense of discomfort that lingered from her encounter with Kyle. "I know, but..." she began, trailing off as uncertainty gnawed at her resolve.

Clea's smile faltered for a brief moment before she quickly regained her composure. "Listen, darling, you're on the verge of stardom," she declared, her voice firm and commanding. "You need to seize every opportunity that comes your way. Kyle is your ticket to the top, and you can't afford to let him slip away."

Jazmine swallowed hard, her mind swirling with conflicting emotions. Part of her longed to please Clea and fulfill her dreams of fame and fortune. But another part of her, a quieter voice buried deep within, whispered of doubts and fears she couldn't ignore.

Clea leaned forward, her eyes locking onto Jazmine's with unwavering intensity as she continued to weave her web of persuasion. "Jazmine, darling, I understand your concerns," she began, her voice gentle yet insistent. "But you have to remember, this is Hollywood. It's all about appearances, about playing the part."

Jazmine shifted uncomfortably in her seat, her brow furrowing with uncertainty. "But Clea, I'm not sure I can do this," she admitted, her voice tinged with doubt. "I struggled to feel anything for Kyle because... because I'm not into men. I never have been, and I don't think I ever will be."

Clea's smile never wavered, her gaze unwavering as she reached out to gently take Jazmine's hand in hers. "Sweetheart, I know it's difficult," she murmured, her tone soothing and empathetic. "But think about the opportunities that lie ahead. Kyle is Hollywood's golden boy, and being seen with him could open so many doors for you."

Jazmine's mind raced with conflicting emotions, torn between her own feelings of discomfort and the tantalizing promise of fame and success that Clea dangled before her. "I just don't know if I can keep pretending," she confessed, her voice barely above a whisper.

Clea's grip tightened reassuringly, her voice filled with conviction. "You're stronger than you think, Jazmine," she declared, her words laced with confidence. "And besides, who's to say what the future holds? Maybe this is just the beginning of something wonderful."

Despite her lingering doubts, Jazmine found herself nodding along, drawn in by Clea's unwavering optimism and belief in her abilities. Deep down, she knew that Clea was right—that she had come too far to turn back now. With a resigned sigh, she squared her shoulders and **** a smile, determined to face whatever challenges lay ahead with courage and determination.

Jazmine sat before the mirror, her reflection illuminated by the soft glow of vanity lights. She took a deep breath, trying to steady her nerves as she applied the final touches to her makeup routine. Her hands moved with practiced precision, expertly blending foundation onto her flawless complexion and adding a subtle touch of color to her cheeks.

As she worked, her mind drifted back to the events of the previous evening—the uncomfortable dinner date with Kyle that had left her feeling unsettled and uncertain. Despite Clea's reassurances, Jazmine couldn't shake the nagging feeling of unease that had settled in the pit of her stomach.

With a sigh, she pushed aside her doubts and focused on the task at hand. Glancing down at the outfit she had selected for the day, she couldn't help but feel a twinge of self-consciousness. The ensemble was casual yet undeniably stylish, a reflection of her status as a Hollywood starlet.

She wore a form-fitting turquoise top that hugged her curves in all the right places, the plunging neckline offering a hint of allure without veering into overtly provocative territory. Paired with a pair of high-waisted jeans that accentuated her slender waist and toned legs, the outfit struck the perfect balance between sexy and sophisticated.

Beneath her clothes, Jazmine wore a lacy black bra and matching panties, the delicate fabric serving as a reminder of the woman she had become. It was a stark contrast to the boxers and briefs she had once worn as Jackson Steele, a reminder of the lengths she had gone to in order to pursue her dreams.

As she applied a final coat of mascara to her lashes, Jazmine couldn't help but reflect on the irony of her situation. Here she was, living out her wildest fantasies as a glamorous Hollywood actress, yet unable to shake the lingering discomfort that came with it.

With a resigned sigh, she pushed aside her doubts and **** a smile onto her lips. Today was a new day, she reminded herself, a chance to face whatever challenges lay ahead with grace and determination.

Jazmine descended the stairs, the soft click of her heels echoing through the hallway as she made her way to the kitchen. As she entered, the aroma of freshly brewed coffee filled the air, mingling with the scent of warm pastries that Clea had set out on the countertop.

Clea was already seated at the small breakfast table, a steaming mug of coffee cradled in her hands. Her outfit was effortlessly chic, a reflection of her impeccable sense of style. She wore a crisp white blouse tucked into a pair of tailored trousers, the fabric draping elegantly over her slender frame.

"Good morning, darling," Clea said, her voice warm and welcoming as she rose to her feet.

Jazmine couldn't help but smile at the sight of her friend, her heart swelling with gratitude for the woman who had become like a sister to her. They shared a brief but heartfelt hug, their arms wrapping around each other in a gesture of camaraderie and affection.

The daily hug routine had become a cherished ritual for Jazmine, a moment of solace and connection in the midst of her hectic life. In Clea's embrace, she found comfort and reassurance, a reminder that she was not alone in this journey.

But for Clea, the daily hug was more than just a gesture of friendship—it was a strategic move, designed to strengthen their bond and solidify their partnership. Beneath her warm exterior, Clea's mind was always calculating, always focused on the end goal.

Yet despite her ruthless determination, there was a flicker of gratitude in Clea's heart as she looked at Jazmine. In her, she saw a kindred spirit, someone who shared her ambition and her drive to succeed. And as they sat down to breakfast together, Clea couldn't help but feel a sense of pride in how far they had come, and how much further they had to go.

Jazmine reached for the sleek silver coffee pot, pouring herself a steaming cup of coffee. The rich aroma enveloped her senses, offering a momentary distraction from the weight of the conversation to come.

Clea leaned against the kitchen counter, her expression serious as she sipped her coffee. "Alright, Jazmine," she began, her voice steady and determined. "Today is going to be a pivotal day for you."

Jazmine nodded, her heart pounding in her chest as she braced herself for what was to come. She knew that Clea had never been one to shy away from a challenge, and today would be no exception.

"We're going to start with some intensive training," Clea continued, her gaze unwavering. "I want you to develop an attraction to men, or at the very least, learn how to act like you are."

Jazmine felt a surge of anxiety rise within her at the thought of confronting her discomfort head-on. She had always been honest with herself about her feelings, but now, faced with the prospect of pretending to be someone she wasn't, she couldn't help but feel a twinge of unease.

Clea laid out the plan with precision, detailing each step of the rigorous regimen she had devised. "First, we'll start with some research," she said, her tone businesslike. "I want you to watch some porn videos and take detailed notes on the physical attributes of the men you see."

Jazmine's cheeks flushed at the suggestion, her mind reeling at the thought of delving into such explicit material. But she knew that Clea was right—she needed to push herself out of her comfort zone if she was ever going to succeed in this out-of-the-box plan.

Jazmine shifted uncomfortably, her fingers tightening around the handle of her coffee cup as she listened to Clea's plan. "I don't know, Clea," she began, her voice hesitant. "I think I'll be fine as things are. I can manage to kiss him or whatever."

Clea arched an eyebrow, her expression incredulous. "Oh, honey," she said, shaking her head. "It's not just about kissing. What if Kyle wants more than that? What if he wants a blowjob? Or worse, what if he wants to have sex?"

Jazmine's cheeks flushed at the blunt words, her mind reeling at the thought of being put in such a compromising position. "I...I hadn't thought about that," she admitted, her voice barely above a whisper.

Clea leaned forward, her gaze piercing. "Exactly," she said, her tone firm. "These are realistic and likely situations you'll be in with any man, Jazmine. And if you're going to convince them that you're actually a woman, you need to be able to go through with it."

Jazmine swallowed hard, her stomach churning with unease. She knew that Clea was right—she couldn't afford to be naive about the challenges she would face in this industry. But the thought of engaging in such intimate acts with a man made her skin crawl.

"I just don't know if I can do it, Clea," she admitted, her voice trembling with uncertainty.

Clea reached out, placing a reassuring hand on Jazmine's arm. "I know it's scary, sweetheart," she said, her voice gentle. "But I believe in you. You're stronger than you think, and you have me here to support you every step of the way."

Jazmine met Clea's gaze, a flicker of determination igniting within her. She knew that she couldn't let her fears hold her back—not when she had come this far.

Clea wasted no time as she grabbed her laptop, a notepad, and a pen, setting them down in front of Jazmine with purpose. The laptop screen flickered to life, revealing a familiar website: PornHub.

With a determined click, Clea selected a video titled "Hot Studs Bang Babes: A Compilation." Jazmine's stomach churned as she read the title, already dreading what she was about to witness. But Clea was relentless in her pursuit of Jazmine's transformation, and there was no escaping it now.

"Alright, Jazmine," Clea began, her voice firm. "Today, you're going to take some detailed notes on the men in this video. Pay attention to their masculinity, their cocks—anything you find noteworthy. This is all part of your training to develop an attraction to men, or at least know how to act like it."

Jazmine nodded weakly, her heart hammering in her chest. She picked up the pen, her hand trembling as she prepared to write down her observations. The video started, and Jazmine **** herself to focus on the task at hand.

The scenes unfolded before Jazmine's eyes like a surreal nightmare. Muscular men, their bodies glistening with sweat, engaged in passionate encounters with women. Limbs entwined, bodies pressed together in a frenzied dance of desire. Moans filled the air, mingling with the sound of flesh slapping against flesh.

Jazmine's gaze flickered from one couple to the next, her discomfort growing with each passing moment. She couldn't tear her eyes away, even as her stomach churned with unease. Clea's voice echoed in her ears, pointing out specific attributes of each man that she found attractive—his chiseled jawline, his defined abs, his well-endowed member.

Her hand trembled as she picked up the pen, her heart pounding in her chest. With a shaky breath, she **** herself to focus, determined to fulfill Clea's expectations. She began to jot down her observations, her handwriting shaky and uneven as she struggled to keep up.

"The first guy has a strong jawline," she murmured to herself, her voice barely above a whisper. "And his abs... they're so defined." She hesitated for a moment before adding, "His cock... it's... it's huge."

Each detail she noted felt like a betrayal of herself, a surrender to the expectations placed upon her. But she pushed aside her doubts, forcing herself to continue. She cataloged every aspect of the men's performances—their thrusts, their groans, their expressions of ecstasy—as if committing them to paper would somehow make them real.

As the hours dragged on, Jazmine found herself sinking deeper into a maelstrom of discomfort and confusion. The explicit scenes playing out before her eyes left her feeling overwhelmed and nauseous, yet she **** herself to stay focused, to absorb every detail with unwavering attention.

Her hand trembled as she scribbled notes in her notebook, each word a testament to her growing unease. She cataloged every aspect of the encounters with meticulous detail, her writing becoming more elaborate and explicit with each passing moment.

"The women, they... they're so eager to please," she muttered under her breath as she wrote, her voice barely audible over the sounds of moans and groans emanating from the screen. "They... they act like sluts, begging for it, taking whatever the men give them."

Jazmine winced as she wrote, the words leaving a bitter taste in her mouth. It felt wrong, somehow, to talk about men and women having sex from this perspective. But she knew that she had to push aside her discomfort if she wanted to succeed in her new identity.

"And the men... they... they treat them like... like objects," she continued, her voice faltering as she struggled to write the right words. "They... they use them, take whatever they want, without a second thought."

But amidst the revulsion, there was a nagging sense of obligation—a relentless voice urging her to find something, anything, to admire about the men on the screen. With a sigh, she **** herself to focus, to search for the qualities that Clea had deemed attractive.

"The men... they're... they're strong," she murmured as her writing flowed, her words tinged with ****. "And... and they're... they're confident. They... they know what they want, and they... they take it."

With each passing moment, Jazmine felt herself slipping further into a world of contradictions and compromises. Her heart ached with the weight of her doubts, yet she knew that she had **** but to press on, to bury her misgivings beneath a facade of determination.

And so, with a heavy heart and a trembling hand, she continued to watch, to observe, to record, until the final frame faded to black, leaving her alone in the suffocating silence of her doubts.

By the time the video finally came to an end, it was the afternoon. Jazmine felt physically and emotionally drained. She handed over her notepad to Clea, her eyes downcast with exhaustion.

Clea scanned through the notes, her expression unreadable. "Good job, Jazmine," she said finally, her voice tinged with satisfaction. "You're making progress."

Jazmine **** a weak smile, but inside, she felt a sense of emptiness. She couldn't shake the feeling that she was losing a part of herself in this process, and she wasn't sure if it was worth it.

The next day, the morning sun filtered through into the house, casting a warm glow over the kitchen as Jazmine settled in at the island, her eyes fixed on the laptop screen before her. The familiar sights and sounds of pornography filled the room as she hit play on yet another porn compilation, the images flickering to life with a tantalizing promise of arousal.

Jazmine's heart raced with a mixture of anticipation and apprehension as she watched the scenes unfold before her eyes. The explicit imagery left her breathless, her pulse quickening with each passing moment as she struggled to keep up with the relentless onslaught of desire.

But amidst the chaos, a strange sense of clarity washed over her, as if she were seeing the world with newfound clarity. The men on the screen seemed larger than life, their bodies pulsating with raw, untamed energy as they ravished the women with a ferocity that bordered on primal.

Her hand trembled as she picked up her pen, her mind racing with a torrent of thoughts and emotions. With a sense of grim determination, she began to write, her words flowing onto the page with an ease that surprised her.

"The men... they're... they're like animals," she muttered under her breath, her voice barely audible over the sounds of moans and groans emanating from the screen. "They... they fuck like beasts, taking whatever they want, however they want it."

Her words spilled forth in a rush of raw, unfiltered desire, each sentence more explicit than the last as she delved deeper into the depravity of the scenes before her. She cataloged every detail with meticulous precision, her writing becoming more elaborate and obscene with each passing moment.

"Their cocks... they're so... so fucking huge," she continued, her voice trembling with excitement as she described the men's impressive endowments in lurid detail. "And the way they... they thrust into the women, pounding them into submission, it's... it's fucking hot."

Jazmine's heart pounded in her chest as she wrote, her body thrumming with a primal urge that she could no longer ignore. With each stroke of her pen, she felt herself drawn deeper into the world of lust and desire, her inhibitions melting away in the heat of the moment.

And as the morning wore on, she found herself lost in a haze of arousal and ecstasy, her notes becoming more explicit and obsessive with each passing moment. She reveled in the taboo of it all, surrendering herself to the carnal pleasures that consumed her, until the final frame faded to black, leaving her alone in the suffocating silence of her desires.

Just as the silence covered the room, Clea sauntered into the kitchen, her gaze fixated on the notepad sprawled out on the island. With a sly smile, she picked it up and began to scan the pages, her eyes widening in surprise at the explicit content written there.

"Wow, Jazmine," she remarked, her tone laced with admiration. "These notes are... impressive."

Jazmine's cheeks flushed with pride at the praise, her heart swelling with a sense of accomplishment. She had poured her heart and soul into those notes, and it felt good to finally be recognized for her efforts.

Clea turned to face her, her expression curious as she posed a series of questions, almost like a test to gauge Jazmine's newfound knowledge and attraction to men.

"So, Jazmine," Clea began, her voice laced with curiosity. "After watching all those videos and taking such detailed notes, do you feel like you've developed an attraction to men? Or at least, a better understanding of what it means to be attracted to them?"

Jazmine took a moment to consider the question, her mind racing with thoughts and emotions. She had spent hours poring over those videos, dissecting every aspect of the men's behavior and anatomy. And while she couldn't deny the physical appeal of the men on screen, she still felt a lingering sense of discomfort at the thought of being intimate with them.

"I mean, I guess so," she replied hesitantly, her voice tinged with uncertainty. "I can appreciate their... physical attributes, I suppose. And I understand why women might be attracted to them."

Clea nodded in understanding, her gaze probing as she continued to press for more details.

"And what about their... sexual prowess?" she inquired, her tone suggestive. "Did you find yourself drawn to their... techniques, let's say?"

Jazmine swallowed hard, her cheeks flushing crimson at the explicit nature of the question. But she knew that she had to be honest if she wanted to succeed as Jazmine Jade.

"I mean, yeah," she admitted, her voice barely above a whisper. "Some of the things they were doing... it was pretty... impressive, I guess."

Clea grinned knowingly, her eyes twinkling with mischief as she leaned in closer.

"And what about their... endowments?" she asked, her tone teasing. "Did you find yourself... intrigued by their... size?"

Jazmine's heart pounded in her chest as she recalled the explicit details she had written in her notes. She had cataloged every aspect of the men's anatomy, from their impressive length to their girth and beyond.

"Yeah," she replied breathlessly, her voice barely audible over the pounding of her heart. "I mean, they were... pretty well-endowed, I guess."

Clea's grin widened into a smirk as she leaned back, clearly satisfied with Jazmine's responses. She had passed the test with flying colors, proving that she had indeed learned something from her rigorous training.

"Well, Jazmine," Clea said, her tone playful. "It looks like you're well on your way to becoming the starlet you were always meant to be. Keep up the good work."

Jazmine **** a weak smile, her heart heavy with the weight of her own deception. She couldn't help but wonder if she would ever truly be able to embrace the role she had been **** into, or if she would forever be trapped portraying a character in the movie that she was living in.