Thinking about it

Rachel sat alone in her office, long after Jack had left, the city lights casting faint reflections against the glass windows. She rubbed her temples, a familiar ache forming, but it wasn't from the day's work. It was something deeper, something that had been nagging at her for weeks now. Ever since she'd started listening to Jack's playlists.

Her career had always been her focus, the single thread that kept her grounded. Romance, intimacy—those things had come and gone, never sticking, never feeling necessary. She was independent, successful, respected. But lately, an unsettling feeling had crept in. A sense of missing out, of being incomplete. She hadn’t thought much about her sexuality before. It was always just... there, a background element to her strong, capable self.

But that had recently changed. Her insecurities about her attractiveness had bubbled up unexpectedly. Why now? She had never been concerned about it before, dismissing fleeting thoughts of relationships or physical desires as distractions. And yet, sitting here in the quiet of her office, she couldn’t shake the feeling that maybe she'd neglected something essential.

Jack’s experiment had sparked something in her. At first, it seemed like a professional exercise—something to help her relax, focus more effectively. But the playlists... they had done more than that. They had unearthed something. Her growing unease about her desirability, her femininity. These weren't new thoughts; they'd been there, buried deep beneath years of ambition and responsibility. But the playlists had helped her tune into them, to recognize them without judgment.

She thought about Jack, how easy it had become to trust him, to value his opinion in ways that felt natural, even comfortable. Why is his approval so important to me now? She wondered, frowning slightly. It wasn’t like her to seek validation. But it wasn’t ****, either. It had felt... organic. Authentic, even.

Rachel decided that Jack hadn’t pushed her into anything. Not really. He’d simply created a space where her subconscious could speak up, and now she was listening to it, probably for the first time in years.

Her insecurities had been a wall, but with Jack's help—his experiment—she was breaking it down. Letting herself be ****, intimate, in ways she hadn’t before. There was a strength in that, too, she decided. She didn’t have to choose between being the strong professional and owning her sexuality. She could do both.

She straightened her back, a new determination settling in. She wouldn’t shy away from this. She’d embrace it—evolve. Professionally, she was already confident. Now, she would work on confidently allowing her physical desires, her femininity, to be part of who she was.

Rachel’s fingers hovered over her phone, briefly considering texting Jack, but then she set it down. There was no need. She didn’t need his approval for this. This was about her.

But still, somewhere deep inside, she knew Jack had played a part. I value Jack's friendship and approval deeply, her mind whispered. Following Jack's suggestions feels good, and helps me relax. Weird. She shook off the thought, standing up and grabbing her things.

Whatever the reason, she was in control now. She’d make this part of her life. On her terms.

Rachel lay in bed, staring up at the ceiling, her mind still racing with everything she’d realized that night. She wasn’t the type to hesitate once a decision was made. She acted. She achieved. And now, she was ready to tackle this new part of herself the same way she’d conquered her career—head-on.

Her thoughts drifted to the one indulgence she’d allowed herself over the years: the secret thrill of wearing lingerie under her sharp, professional outfits. No one knew. It had been her own private rebellion, a silent expression of the part of herself she’d kept hidden. The silky fabrics, the lace hugging her skin, always felt like a quiet reminder that there was more to her than the polished exterior she showed to the world. But she had never taken it further.

What if I did? The question sent a pulse of heat through her. What would it mean to embrace that side of her fully? To not just wear the lingerie but... let it define a new part of her identity, a new confidence? Could she push it further, let that secret part of herself spill out into the open, just like she had today with Jack? The memory of him seeing her bra, the way his eyes had lingered, the encouraging hunger in his voice—it sent a shiver through her. He had liked it. He had approved of her.

Rachel bit her lip, a plan forming in her mind—something bold, something that scared her but excited her at the same time. Maybe she could take that step. Show him more, in her own way, at her own pace. Gauge his reaction. But also... not just for him—for herself. She needed to feel that power again, to own that part of her, to make it real. Tomorrow, she would wear her favorite, most daring lingerie under her suit, and she wouldn’t just keep it a secret. She’d find a way to let it be known, subtly. Maybe a glimpse, a flash of lace at the edge of her blouse... something that would feel both empowering and thrilling. God, could I actually do that?

Her heart raced with the thought. I can do that, she told herself. She needed to own it, not just hide it away. This was her body, her femininity, and she was ready to wield it as confidently as she did her business strategies.

But even as she formed the plan, a creeping thought lingered at the edges of her mind. What would Jack think? His encouragement had become... important. Pivotal, even. She blushed, trying to imagine if he'd be pleased be if he knew what she was planning. She hated admitting how much that thought affected her, but it did. It mattered.

Her heart raced, her body responding to the intensity of it all. She hesitated only for a moment before her hand slid beneath the covers, exploring the softness of her skin, wanting to rediscover her sensitive places with an intensity she hadn’t allowed herself to feel in a long time. The thrill of it was overwhelming, the sense of empowerment intoxicating.

Her hand trailed down, her fingers decisively moving underneath the soft cotton of the underwear she slept in, her breath catching as she cupped her pussy, tentatively sliding a finger in between her lips. Her body responded instantly, heat pooling deep inside her as she stroked herself with a building passion. This wasn’t just about pleasure. It was about awareness, power—her power.

As her fingers found her clit, her mind wandered, the thought of Jack’s approval surfacing again. His opinion mattered, didn’t it? It had felt so good when he'd praised her, when she'd showed him what she had been hiding, when he had stared, hungrily... when the sight of her breasts had pleased him. She imagined showing him more, unhooking her bra, sliding off her trousers, following his encouragement. What would he say? She imagined she would ask him how to continue, she imagined he would tell her that he wanted to touch her, to feel her.

She would come closer, she would straddle his lap. She imagined letting Jack do to her whatever he wanted, letting him explore her body like she was doing now. Her hand moved quicker, stronger, fingers rhythmically circling her most sensitive part. She imagined how she would let Jack grab her breasts, hold her waist, squeeze her butt. How he would kiss her neck, how he would praise her. You're stunning, Rachel.

She even imagined letting him... push a finger... Aaaiih...—before she could continue her fantasy, a loud moan escaped her lips, and she surrendered to a flood of sensations, emotions. Like a volcano erupting after years of seismic build-up, intense vibrations of pleasure suddenly waved through her whole body, from her pulsating clit to the tips of her fingers and toes. She felt everything contracting, tensing up, releasing, as her mind went blank for several seconds, maybe minutes. Euphoria.

Her heart was beating rapidly, her nether regions softly throbbing and pulsing, and Rachel was utterly at peace—every nerve-ending soft, every muscle relaxed. Satisfaction washed over her as she sank deeper into the bed, her body humming with the sensation of finally letting go. It wasn’t just about the physical release. It was the surge of power, of reclaiming something deeply personal, intimately hers. Starting tonight, she would work on owning it, fully. A tsunami of excitement, acceptance, and unshakable certainty had washed over her, leaving her breathless and calm in the aftermath.

Blushing deeply but feeling better than she had in weeks, Rachel’s eyes finally fluttered shut. As she fell asleep, her resolve stronger than ever, her mind idly buzzed with plans for the morning—her secret rebellion about to become something much bigger.