5. Cassandra
5
CASSANDRA
T he night was just beginning, and the chandeliers reflected light across the walls of the private bar in Manhattan. Cassandra stood near the polished counter, her long blonde hair falling down her shoulders like silk. She looked around, taking in the scene. There was chatter, the clinking of glasses, and the laughter that was expected at a New York City event.
It was a late Saturday night, and the fashion gala hosted by Vivienne Blackwood had brought out a mix of elite designers, models, and socialites. Cassandra’s blue eyes sparkled under the light as she tried very hard to maintain the energy to be extroverted in her older age.
“Cassandra!” Vivienne’s voice rang out, cutting through the large room. She approached with a confident stride learned from years of attending fashion shows. She had a warm smile on her face and was dressed in a fancy silver gown. As always, her presence demanded attention.
“Vivienne, it looks wonderful in here,” Cassandra replied. Memories returned of the time when they’d crossed the line from colleagues to something more intimate. They’d shared a moment, and it had been an interesting night. Power meeting power. As she met Vivienne’s gaze, a thought resurfaced…that night hadn’t been as fabulous as one might imagine. Sexually, they just hadn’t been compatible.
“You always know how to throw the best parties,” Cassandra continued, sipping her margarita to distract from the redness on her cheeks. She couldn’t deny the chemistry that had existed between them, but when she thought back to their encounter, she remembered how weirdly similar they’d felt. Both of them were powerful women used to leading in life. There had been no spark of contrast.
Vivienne laughed and tossed her dark hair back. “Well, darling, you know how I adore the spotlight. But tonight is about bringing us all together.” She leaned in closer, her voice a whisper. “And as always, you clean up rather nicely.”
Cassandra chuckled, surprised by the compliment. The conversation flowed easily between them, both women accustomed to the charm required in their industry.
“Tell me, do you remember when we…?” Vivienne started.
Cassandra cleared her throat. “Yes, I remember.” She managed a lighthearted smile, but her tone shifted slightly as she continued, “We’re just a little too alike, Vivienne. Don’t you think?”
Vivienne tilted her head, a puzzled look crossing her face. “Yes…but what do you mean by that? I wonder if it’s the same way I analyzed it.”
Cassandra felt strangely vulnerable. Was Vivienne Blackwood really going to lay her thoughts out now? “You know,” she said, taking another sip of her drink. “We’re both in charge, we both thrive on leadership.”
The loud chatter of the event faded for a moment as Vivienne considered her words. Then she straightened, one eyebrow arched defiantly. “So, you mean to say you prefer a little bit of chaos in your life?”
“Maybe chaos isn’t the right word,” Cassandra replied carefully.
“But you must tell me! How have you been since...well, since Nadine James took your client?” Vivienne asked, her expression turning more serious.
Cassandra sighed, the mention of Nadine bringing an edge to the night’s pleasant mood. “Super pissed, to say the least,” Cassandra admitted, rolling her eyes a bit for effect. “But I did get her to apologize for that. As much as she pisses me off, I can’t deny that she’s talented and has networking power.”
Vivienne raised an eyebrow, clearly amused. “Networking power?”
“Absolutely!” Cassandra laughed, glancing at the bustling crowd. “It’s like ever since I noticed her, I see her everywhere. It’s as if she’s always lurking around every event. I swear, she might as well be my shadow!”
Or my submissive?
As she spoke, the crowd shifted, and there, entering confidently through the large entrance, was Nadine James herself. Her shoulder-length dark hair stood out, at least to Cassandra. She wore an eye-catching gold dress that shimmered under the lights. Cassandra couldn’t help but admire her impeccable timing.
“Speak of the devil,” Cassandra muttered, her eyes widening. “Was she invited?”
Vivienne shook her head, a grin forming. “Not formally. I heard she managed to charm her way in.”
Cassandra chuckled, the irony of it all hitting her like a wave. “Of course she did,” she said, crossing her arms with a smirk. “Nadine has a way of getting what she wants. Should we be worried she’ll take over the whole event?”
“Oh, I doubt that!” Vivienne laughed lightly. “But she’ll definitely add some spice to the evening.”
As Nadine waved and greeted various guests, Cassandra felt a combination of annoyance and admiration. There was something magnetic about her, a kind of energy that drew people in. Cassandra knew that as she mingled, secrets and laughter would follow her. It was infuriating, but also fascinating.
“Are you going to go talk to her?” Vivienne asked, her eyes showing mischief.
“Not yet,” Cassandra replied, though she felt something pulling her in Nadine’s direction. “I need to gather my thoughts. Besides, if I approach her now, she’ll think I’m intimidated…or worse, that I care!”
Vivienne shook her head, still amused by Cassandra’s annoyance. “Cassandra, you’re a force all on your own. Just remember, you don’t have to compete with her. You’re in different leagues.”
“True,” Cassandra said, taking another sip from her drink. “But it’s hard not to feel that way when she’s practically everywhere I turn!”
As they stood there, watching the high-end fashion elites socialize around them, Cassandra decided to approach Nadine. Maybe this was a sign that Cassandra could choose a professional collaboration that could benefit them both. After all, in the world of fashion, cooperation could be just as powerful as competition.
But for now, she would enjoy the event, celebrate the creativity in the room, and let the evening play out. After all, there were plenty of moments left in the night, and a little intrigue was always good for business.
Putting on an icy smile, Cassandra approached Nadine, who was chatting happily with a couple of stylists. Why was Nadine here? How was she so confident flaunting a startup company to all of these moguls who came from generations of prestige?
“Look who it is!” Nadine said as she spotted her. “Cassandra Wynter! The Ice Queen.”
“Hello, Nadine,” Cassandra replied, her tone cool and even. “What a surprise to see you here.” She couldn’t help but notice the playful smirk on Nadine’s lips, and desperately wanted to assert her dominance again.
“I wanted to congratulate you on finally launching Wynter Media’s first TikTok account!” Nadine said, her lips curling farther. “Quite the move, don’t you think? Copying the trends we’ve set at Pulse Media? You must really admire us.”
“Imitation is the highest form of flattery,” Cassandra shot back, unable to contain her annoyance. She could feel her cheeks warming, and not just from the tequila. She didn’t want to admit that she’d been following Nadine’s social media strategy closely. After all, Nadine was a fierce competitor, now somehow at the forefront of fashion trends.
“I thought you were against jumping on social media bandwagons,” Nadine teased, arching an eyebrow. “What happened? Did you finally see the light?”
Cassandra forced a pleasant smile, masking the irritation beneath the surface. “Trends change, Nadine. I just adapt like everyone else in this industry.”
A tense moment hung between them, filled with unspoken words and memories of last week that would stay hidden, at least for now. Behind the businesslike banter, Cassandra felt the flutter in her stomach again. There was a thrill in exchanging sly comments that reminded her just how electric her connection with Nadine had been.
Memories of how good it had felt to grind her orgasm into Nadine’s sweet willing little mouth flitted through her head.
“And how does it feel to relinquish the title of trendsetter to your rival?” Nadine continued, enjoying the playful banter.
“Rivalry is what keeps the spark alive, don’t you think?” Cassandra replied, her voice low, as if they were still tucked away in that bathroom, the world outside forgotten.
“True,” Nadine said, leaning in closer. “And there’s something thrilling about being at odds with someone so capable.”
I’m going to fuck that smart mouth out of her.
They exchanged small talk about the event, the latest trends, and a recent dress that had stolen the show. As they chatted, Cassandra’s mind wandered to their previous encounter at the fashion show meeting. However, as Nadine’s gaze grew serious, Cassandra felt tension rise between them.
“You know,” Nadine started slowly, leaning slightly closer, “I still can’t believe we...” She lowered her voice, glancing around to ensure no one was eavesdropping. “What happened in the bathroom after that meeting.”
Cassandra blinked, her smile faltering for just a moment. She cleared her throat. “What do you mean, Nadine? I don’t know what you’re talking about.”
Nadine’s brow furrowed, a mix of annoyance and disbelief washing over her features. “Cassandra, come on! It was just us in there...” She crossed her arms, as if trying to protect herself from the confusion in the air. “You don’t really want to pretend it didn’t happen, do you?”
The euphoria from the alcohol began to mix with a strange feeling in the pit of Cassandra’s stomach. She loved her parties and her glamorous life, but Nadine’s words sliced through the joy like a knife. As much as she wanted to, she wasn’t sure it was the best idea to revisit what had happened, not now when the night was still young.
“Let’s just forget about that and enjoy the night,” Cassandra offered, forcing a laugh. “I don’t want to ruin this evening.”
Nadine rolled her eyes, clearly frustrated. “Fine. But I have been thinking about it. Want to take a shot with me?” Without waiting for an answer, she signaled the bartender.
“Sure! Let’s do it,” Cassandra replied, her heart racing. There was something about Nadine’s confidence that both thrilled and unnerved her. The bartender poured the shots, and without a second thought, they both raised their glasses.
“To the chaos of the runway!” Nadine cheered, a wicked smile spreading across her lips. They clinked their glasses, and in one swift motion, they downed the shots together.
Feeling a surge of confidence from the shots, Cassandra decided it was time for a breath of fresh air. She touched Nadine’s arm lightly and gestured for her to follow. With a warm smile, Nadine approached, her eyes sparkling with curiosity.
“Where are we heading?” Nadine asked, her head tilting slightly.
“The terrace. I need some fresh air.” Cassandra smiled, already feeling lighter. They pushed through the crowd and stepped outside into the cool night air. The city buzz hummed in the background.
As they walked to a secluded corner of the terrace, the faint lights of the city twinkled below them. Cassandra leaned against the railing, feeling the weight of her responsibilities lift for just a moment. “You know,” she began, her voice steady but with a hint of vulnerability, “I feel really inspired by you tonight. I want to be a more collaborative leader. It’s something I’ve struggled with, especially in this industry.”
Nadine’s expression softened, her gaze set on Cassandra as if every word spoken was a treasure. “That means a lot coming from you,” she replied gently. “I’ve always admired how you manage Wynter Media.”
“It’s easy to get caught up in the competition and forget the importance of teamwork,” Cassandra continued. She felt her cheeks warm as she spoke openly. “But after talking with you, I’m thinking that maybe building connections could not only strengthen my leadership, but also make my work much more fulfilling.”
Nadine smiled, a mixture of appreciation and admiration lighting up her features. “Collaborating can spark so much creativity. We could do amazing things together.”
Cassandra’s heart raced at the sincerity in Nadine’s voice. They stood so close. The world around them seemed to fade. The atmosphere felt charged. Without thinking, Cassandra reached out to gently tuck a stray hair behind Nadine’s ear.
In that quiet corner of the terrace, with the neon city lights glowing around them, Cassandra leaned in closer. Nadine’s eyes widened slightly in surprise, but she didn’t pull back. Instead, she drew closer, too, and their lips met in a passionate kiss.
It was a kiss full of unspoken words, dreams, and aspirations. Cassandra was hungry for her. Her tongue pushed into Nadine’s willing mouth before she drew Nadine’s own tongue into her own mouth and sucked upon it. In that moment they both felt the weight of their ambitions lift. As they pulled away, breathless and flushed, Cassandra couldn’t shake the feeling that this could be the beginning of something not just sexual or romantic, but revolutionary.
“Wow,” Nadine said softly, her eyes shining with surprise and joy.
Cassandra smiled. Kissing Nadine was a great pleasure. But, she could think of certain other things she wanted to do to her more.
Cassandra leaned against the cool metal railing of the terrace, her blue eyes sparkling like the city lights below. The warm breeze caught her long blonde hair and lifted it gently, as if to mirror the thrill she felt. She was fifty-two, but tonight she felt like a teenager.
Beside her stood Nadine, a bundle of energy with a smile that could light up even the darkest corners of Manhattan. Their connection wasn’t just about the kiss or the power play between them…it was about breaking free from their daily routines and stepping into something new.
“Let’s go up,” Nadine suggested, pointing toward the stairwell that led to the rooftop above them. “No one will find us there.”
“Why do you want to be alone with me, Nadine? What is it you want from me?”
Cassandra watched as Nadine’s lovely face became suddenly shy and uncertain, as though afraid to ask for what she wanted.
Cassandra smirked. She thought as much.
“I…uh…” Nadine’s voice was shaky and she couldn’t look Cassandra in the eye.
Cassandra took Nadine’s chin in her hand and tilted it up towards her own face so Nadine had to look her in the eye.
“You’ll need to look me in the eye and ask explicitly for what you want, or I won’t give you anything. I’ll turn and head straight back into that party.”
She watched as Nadine’s lovely hazel eyes widened in a curious mix of what had to be fear and excitement, heavily laced with desire.
Her lips quivered as though about to speak, but no sound came out.
Lovely full lips. Felt so good on my pussy.
Cassandra felt herself swell with the confidence of dominance again.
“Say the words, Nadine.” Cassandra’s voice was stern and her grip on Nadine’s chin was tight. She watched as Nadine began to pull herself together as much as was possible. At least enough to speak.
“I…” her voice was stilted and hoarse.
“I…. I mean… please… I mean….”
“SAY IT”
“I want you to fuck me,” the words tumbled from her lips like a waterfall.
Cassandra smiled like the cat who had got the cream.
“I thought you would never ask.”
She paused for a beat, still holding Nadine’s chin in her hand and looking down at her. With her heels on, she was over 6 foot and her height was something she relished.
“Only, I’m going to need a few more details from you, my sweet little slut. Tell me more.”
She watched in joy as Nadine’s face flushed bright red. She maintained her eye contact as Nadine squirmed visually in front of her.
Nadine took a deep breath and continued, “I need you to fuck me. I have a desperate need to feel your fingers inside of me. Not gently, either. I need you to fuck me hard and with no mercy. Deep, hard and relentless.” Her voice went quiet and her gaze dropped down to Cassandra’s feet.
She felt a bolt of desire between her own legs. She smiled smugly. Oh, yes.
Little Nadine’s eager submission was a fucking beautiful thing.
“Well then, little Nadine, why don’t you lead the way up to the roof.” Cassandra’s voice was deep with promise.
She released Nadine’s chin, enjoying Nadine’s flustered behavior as she turned and started up the stairs to the rooftop.
Cassandra had let her go first purely because she wanted to watch her lovely round ass in her tight dress as she made her way up the stairs.
And it didn’t dissappoint.
Absolutely delicious.
Cassandra felt her smile taking over her face. It had been a long time since she had desired anyone like this. Sure, she had always enjoyed being dominant, but had often chosen partners who were strong successful women and unfortunately they had also been sexually dominant. So, sexually, she had often clashed with her partners. Sex had never worked out for her quite how she had hoped.
Until now, perhaps.
She might very much clash with Nadine in the boardroom, but sexually at least Nadine capitulated to her in the most beautiful natural way.
As they reached the rooftop, Nadine turned to face her, her eyes wide with need.
Cassandra looked around, enjoying the view over the city at night and its glittering lights and an idea came into her head.
Mmmm, that would do nicely.
“Take off your clothes. All of them,” Cassandra commanded.
Nadine looked around, nervously, like a rabbit caught in the headlights as Cassandra’s hungry gaze roved up and down o ver her body.
She looked as though she was about to speak, to complain, perhaps.
Cassandra cut in harshly, “Of course, if you have changed your mind, you can keep your clothes on and we just go back down to the party.”
Nadine’s eyes panicked slightly before her hands reached to the straps of her dress, beginning to ease it down over her shoulders.
It had been very clear all night that Nadine wasn’t wearing a bra and as soon as her breasts were exposed to the night air, her nipples hardened.
Cassandra nodded in satisfaction, “Good girl,” she said and Nadine smiled in recognition as she continued to ease her dress down. Her breasts were so beautiful in the flesh, large and full, they moved every time she did and her lovely brown nipples were big and inviting.
As the dress moved down over her wide hips, Cassandra couldn’t take her eyes off Nadine’s body, her smooth brown skin lit up by the moonlight. She had all the curves Cassandra’s own body was lacking and that excited her greatly.
The dress dropped to the floor and Nadine stood in her high heels and red panties facing her.
“Panties off. You can keep the shoes on,” Cassandra ordered and Nadine’s hands reached for the waistband of her red silk panties and began to roll them down exposing medium brown curls that matched the hair on her head. Cassandra felt she might explode there and then, but she calmed herself and remained cool and in control until the panties were on the floor and stepped out of.
Cassandra lead her to the railings at the edge of the rooftop. There was a seating area nearby and Cassandra happily took a seat.
“Now, sweetheart. I want you to bend over holding those railings and looking over the city so the whole city gets to see your lovely big breasts.”
Nadine’s eyes glanced around nervously once again, but she quickly moved to obey her orders.
As she bent forwards to the railing, Cassandra could see her the length of her lovely legs, the round full globes of her delicious ass and as it parted, she saw the pinkness of her pussy as it fell open slightly.
Mmmmmm.
“Reach both your hands back and pull your ass cheeks apart. I want to see your pussy. All of it.”
Nadine’s hands obediently reached back, Cassandra could see she was shaking slightly, as they pulled her ass cheeks apart exposing her pussy deliciously. Pink puffy labia opened like a pearl before her. Oh, and she was wet. So very wet.
Cassandra watched as a thin strand of Nadine’s desire began to drip from her pussy.
“Oh, what a sweet sweet slut you look like now,” Cassandra said. “You are so fucking wet for me. Your swollen pussy is literally dripping for me, begging me to fuck it.”
“Please..” Cassandra heard Nadine’s squeaky pleading and she leant back and crossed her legs, enjoying the vision before her of Nadine wide open and wanting and dripping for her. She watched the strand of juice get longer and longer before it broke off and hit the floor.
“Do you like anal sex,” Cassandra asked, suddenly.
“Uh… I don’t really know. It isn’t something I’ve tried much,” Nadine’s voice returned.
“Well,” Cassandra said smugly. “I think you might learn to like it. Every time you come for me, you’ll do so with fingers or toys in your ass. Do you understand?”
“Yes, Mistress.” Nadine’s voice was a nervous gasp.
“Good,” Cassandra said. “In that case I want to to go back to holding the railing with one hand and with your other hand spit on your finger and reach back and work it into your ass hole.”
There was a moment of pause as Nadine no doubt digested her new orders.
It was a test perhaps from Cassandra. All of this was. And so far, Nadine was passing with flying colors. Cassandra felt her own pussy oozing with wetness. She stood to adjust her dress so it was above her hips before she sat down again. She didn’t want to get come on her dress. She reached to press against her own clitoris through her panties, it was swollen and eager as she lazily began to play with it through the damp lace.
She watched in satisfaction as Nadine did indeed obey the latest order and a wet index finger reached nervously around behind her, seeking out her ass hole.
“Play with it a bit,” Cassandra said. “You’ll find everything a lot easier if you get your sweet little hole all warm and wet before you start. Get some wet from your pussy. There’s plenty there.”
Cassandra watched Nadine’s right hand probing for her pussy and pressing her fingers in to take the beautiful juices to her anus. Once there, her fingers began to smear the wetness around the hole, pressing and rimming it, seeming to gain in some confidence as they went.
Cassandra continued to lazily touch herself as she watched in great pleasure. She was in no rush.
When she noticed Nadine beginning to relax into what she was doing, she knew it was time.
“Now, push your index finger inside for me. Slow and deep.”
Cassandra watched eagerly as the tip of Nadine’s finger began to press at her hole forcing it to open for her and then as it did, the tip of her finger disappeared inside and she gasped audibly.
“Good girl,” Cassandra growled. “You look so fucking sexy, you know. You are pleasing Mistress so greatly.”
Her finger gradually disappeared further inside her body.
“How does it feel, sweetheart?”
“A little odd… but it doesn’t hurt. It feels almost electric in here, like electric pulses deep within me.”
“Mmmmm,” Cassandra murmured. “I can’t wait to feel those electric pulses.” She watched as further strands of desire descended from Nadine’s juicy pussy. It was nearly time.
“Push it further in, sweetheart. Be a good little slut for me. All the way in.”
Nadine seemed to readjust her wrist to get the pressure she needed to push her finger in all the way and she groaned deeply.
Cassandra stood up, readjusting her underwear and her dress as she made her way slowly up behind Nadine. She rested her left hand on Nadine’s hip and whispered to her deep and throatily, “I’m going to fuck you now, sweetheart. Hard and deep and relentless just like you wanted. You’ll keep your finger in your ass the whole time, do you understand?”
“Yes…” Nadine gasped. “Yes, please, mistress.”
Cassandra plunged 3 fingers from her right hand deeply and firmly into Nadine’s sopping wet pussy curling them downwards to hit her G spot.
Nadine cried out, loudly.
“You are going to come for me screaming and crying, as the whole city watches you, little sweet slut that you are,” Cassandra growled.
She felt Nadine’s sodden pussy clench around her fingers. She could feel her index finger inside her ass through the thin membranes that separated pussy and ass.
She began to fuck Nadine with her fingers, hard and deep as she had requested. With each thrust Nadine was crying, screaming and squirming with the intensity of it. Her fingers were making sweet squelching noises in the wetness and Cassandra knew if she began to hammer Nadine’s G spot, she would probably squirt.
“You think you might squirt for me, sweetheart?” Cassandra growled, loving the idea of it. She felt alive in a way she hadn’t for years.
“Uh… oh… god…” Cassandra began to ram her fingers hard and fast against Nadine’s G spot. “Oh… fuck… oh… yessss..”
Cassandra smiled to herself as Nadine’s cries became louder. Of course she would.
As she cried out so loudly it was likely the whole party would hear her she squirted violently drenching Cassandra’s dress. Her whole body was quivering and her finger was still rammed tightly all the way up her sweet little ass.
“Oh, you little slut, you’ve come all over my dress. It’s a new season one as well.”
“I’m sorry,”Nadine yelped as Cassandra increased her tempo again banging hard into her. Nadine’s big breasts were swaying with every thrust and Cassandra enjoyed it.
“How sorry are you?” Cassandra asked, relentless in her fucking.
“Very… very… sorr- arghhhhhhhh” Nadine squirted again all over Cassandra’s dress.
“Messy little slut, aren’t you?” Cassandra continued with Nadine screaming and coming, screaming and squirting. She didn’t let up until many orgasms later and when she finally withdrew, Nadine was shaking and whimpering.
“Did you enjoy that, sweetheart?”
“More than any sex ever in my life,” Nadine’s voice was shaky, yet sure of herself.
“Good girl,” Cassandra said. “You can take your finger out your ass and get dressed.”