Sign Here, Jenny
Copyright© 2025 by Saakael
Chapter 5
BDSM Sex Story: Chapter 5 - A cheerleader is tricked by a dominatrix.
Caution: This BDSM Sex Story contains strong sexual content, including Fa/Fa NonConsensual Reluctant BDSM FemaleDom Humiliation Spanking
March 15, 2025 – Florida – 2:35 p.m.
Jennifer Miller (better known as Jenny) couldn’t quite decide whether she should be mortified or secretly proud of herself.
Maybe a little of both? Judging by the flood of DMs lighting up her Instagram, though, her friends had already made their choice: she was a genius. A wicked genius, maybe, but a genius all the same.
At twenty-one, Jenny would never have described herself as some kind of “evil mastermind.” Her looks certainly didn’t suggest anything of the sort. She was beautiful — five foot seven, slim but toned from years of cheerleading, a hobby she still pursued in college), with an angelic face, brown eyes, lightly tanned skin, and long chestnut hair. Sure, she looked like the very opposite of “villainous.”
And her personality matched. She was friendly, nice, quick to laugh, the kind of girl people liked.
But she was also poor. Not dirt-poor, but poor enough to justify the “little scheme” she had set in motion a few weeks earlier.
Her chosen mark? None other than the young woman currently sharing the backseat of a Lamborghini Urus with her: Anastasia Rain (and just to be clear—the Lamborghini was Anastasia’s, not Jenny’s.)
Anastasia Rain was, in many ways, Jenny’s opposite. She was smaller (barely five foot three) with a thin, almost fragile frame, pale skin, long dark hair, and striking green eyes. She was pretty, yes, but not radiant in the way Jenny was.
And more than that, their personalities couldn’t have been more different.
Jenny, cheerleader, was a burst of energy—outgoing, smiling, effortlessly popular on campus. Anastasia, by contrast, was reserved. Timid, even. She kept to herself, spoke little, and gave off the impression of someone who lived mostly in her own head.
And yet, despite all that—or rather, because of all that—Anastasia was one of the most coveted girls on campus. Why? Because she was rich. Filthy rich in fact.
The Rain family wasn’t just wealthy—they were old money. The Rains had been part of the country’s elite for nearly a century and their company, Rain Corp, owned a gleaming tower in New York City. A sign that they seemed destined to stay at the top for decades to come.
And everybody knew (or thought they knew) the same simple truth: a lonely, unsocial rich girl needed attention. And she might just reward it with ... gestures.
That’s why, over the past three years, Anastasia had become something of a “target” for students on campus. The goal? Become her friend, and benefit from her generosity. And it worked.
With a monthly allowance rumored at fifteen thousand dollars, Anastasia could afford to be generous. It wasn’t hard to score a luxury birthday gift (say, a Louis Vuitton bag), get her to foot the bill for the entire party, borrow her car and driver, land an internship at one of Rain Corp’s subsidiaries (though oddly, people bragged about that far less afterward—Jenny had no idea why), and so on.
The holy grail, according to campus gossip, would be to seduce Anastasia. If she was that lavish with mere “friends,” imagine what she might do for a boyfriend ... or rather, in her case, a girlfriend.
Because Anastasia Rain, as more than a few disappointed frat boys had learned, was very openly gay.
But Jenny was a lesbian too. A beautiful, sexy lesbian. A cheerleader, no less—the kind of fantasy that had fueled more than a few campus rumors.
Which is why, for years, people had been telling her she had every chance in the world. That Anastasia could, if properly “managed,” cover some—or even all—of her financial problems.
For over two years, Jenny had brushed off the idea. Playing with someone’s feelings just wasn’t her style. Letting a rich friend pick up the tab for dinner was one thing, but becoming the pretend-girlfriend of a shy heiress purely for gifts—or, more to the point in Jenny’s case, for a steady monthly allowance—was another level entirely.
At least, that’s what she used to think.
Two months ago, everything changed. Her mother lost her job, and the five hundred dollars Jenny had relied on each month simply vanished. Suddenly, rent and groceries became an equation she couldn’t solve.
So, sometime in February, Jenny did what she’d sworn she wouldn’t: she made a move. Casually at first (sitting closer in the library, trading jokes, sharing coffee), then a little bolder, letting her charm bleed through.
At first ... the results hadn’t been great. Anastasia seemed glad enough to see her, yes, but she never quite stepped into the rhythm Jenny was trying to set. No spark, no real pull of attraction.
Then luck had shifted in the strangest way. Toward the end of February, Jenny had managed to wrangle an invitation into Anastasia’s apartment. And there, quite by accident, she had stumbled on the girl’s laptop—left open, screen glowing. A BDSM site.
Jenny had known nothing about BDSM, but the homepage had been hard to misinterpret. The picture of a gagged, rope-bound girl more or less spoke for itself.
For a split second Jenny had frozen, her mind a swirl of impulses. She could have laughed it off, pretended she hadn’t seen, made some joke and moved on. That would have been the safe play. Sensible, even.
But then another thought pressed harder, louder: this was an opening. Maybe the only one she was ever going to get.
Before she could stop herself, the words had slipped out of her mouth—reckless, unplanned, but sharp as a spark in dry grass.
She had told Anastasia she “wouldn’t mind trying it.”
And that was when everything changed.
Within a week, Anastasia had gone from merely tolerating Jenny’s presence—even, on good days, seeming to enjoy it—to actively seeking her out. Not just to spend time together (a point Jenny was still carefully working on), but to arrange a Spring Break for two, in a family-owned house in Florida. A week in which Jenny could “try out” BDSM as much as she liked.
The idea of a BDSM Spring Break had, if she was honest, unsettled Jenny more than a little. She had seen pictures online, enough to know things could get ... intense.
She had very nearly changed her mind—more than once, in fact.
But then came the chorus of her friends, and especially the little clique who had been “benefiting” from Anastasia’s generosity for years. They all agreed it was the chance of a lifetime—and, more importantly, they assured her Anastasia was harmless.
“What do you think she’s going to do? She’s a sweet, lost little thing. She probably wouldn’t even dare to kiss you.”
“BDSM takes skill. Can you honestly picture her tying anyone up?”
“Stop panicking. Worst case, you’ll end up in a pair of fluffy pink handcuffs.”
Jenny had let herself be talked into it. In the end, she’d accepted the offer, and now here she was, riding in Anastasia’s car, about to begin this so-called “Spring Break” with “a little” BDSM (though the “little” part was pure invention on Jenny’s side—Anastasia had never actually said that).
“The house your family owns looks ... kind of out of the way?” Jenny asked.
Anastasia, dressed head to toe in black—a blouse, skirt, and tights—gave a faint smile. “Yes. We don’t like paparazzi in the family.”
Jenny arched a brow. “Do you really get hounded that much?”
“No.” the brunette replied with a mischievous smile. A smile that suggested there was a story behind it.
Jenny didn’t get the chance to press further, because just then the car turned off the main road and onto a long drive leading to a pretty house perched on a rise, overlooking the sea.
The house was exactly what Jenny had pictured a billionaire’s vacation home would look like. Perched high enough to offer a breathtaking view, larger than it had any reason to be, it radiated wealth at first glance. With its mix of wood and stone, crisp white shutters, and the complete absence of neighbors, the place commanded its surroundings with elegance.
“Miss Rain, we’ve arrived,” the driver announced.
“Thank you, George,” Anastasia replied (the man’s name was actually Thomas, but Anastasia had never been particularly good at remembering the names of employees).
Jenny, only half paying attention, nearly jumped out of her skin when her door was pulled open by a man built like a linebacker in a black suit—with a gun riding openly at his hip.
For a split second, Jenny wondered if she’d somehow stumbled into an old mafia movie.
“They’re my bodyguards,” Anastasia said, as if that explained everything, while a second man in an identical suit opened her own door.
Jenny stepped out of the car, her eyes flicking to the guard’s gun.
“Do you really think the guns are necessary?” she asked.
Anastasia laughed. “Normally, no. Very few people are foolish enough to come after my family. But ... you never know.”
Jenny studied her for a moment. The girl beside her seemed ... different. Less timid. She brushed the thought aside. After all, it was only natural for Anastasia to be more confident in her own element, and headed toward the trunk to grab her suitcase.
“What are you doing?” Anastasia asked, amused, already walking toward the front door.
“Getting my bag,” Jenny replied, a little confused.
“George will take care of our suitcases,” Anastasia said, waving her forward with a flick of her hand.
Jenny glanced at the driver, who gave her a reassuring smile as if to back up Anastasia’s words, then she hurried toward the entrance to catch up.
“This isn’t our biggest house,” Anastasia remarked casually, already stepping inside, “but it should do for what I have planned.”
Jenny, crossing the threshold just as those words left Anastasia’s lips, might have worried more about the use of “what I have planned” instead of “what we have planned.” But her train of thought derailed the moment she got her first real look inside.
The entryway opened into a stunning living room, easily fifty square meters, decorated with care—paintings on the walls, no fewer than five sofas, a dining table set for ten, an equally impressive coffee table and the largest television Jenny had ever seen in her life. At the far end, a set of glass doors led out onto a wide terrace, offering another breathtaking view of the ocean.
“There’s a kitchen, but we won’t be using it,” Anastasia said, nodding toward another closed-off room. “Upstairs there are four bedrooms and two bathrooms.”
Jenny nodded, but the feeling of being out of her depth was written all over her face. This “vacation house” was bigger and more luxurious than her parents’ actual house, and she could barely imagine what Anastasia’s parents’ apartment in New York could look like.
A moment later George—Thomas, really—stepped inside carrying their suitcases. Anastasia pointed toward the staircase. “Thank you, George. Put my bag in the master bedroom, and Jenny’s in the one next to it.”
Jenny turned, only to notice that the bodyguards hadn’t followed them inside. Instead, they had taken up positions just outside the front door. The vibe shifted instantly—less “mafia,” more “Secret Service detail guarding a VIP.”
“Don’t worry about the bodyguards,” Anastasia said, settling onto the couch. “They’re very discreet, and they’ll never come in ... unless I ask them to, of course.”
Jenny swallowed hard. When she’d agreed to this spring break, she hadn’t quite accounted for the reality of Anastasia’s power. The girl might have been timid, fragile-looking, even a little lost back on campus—but here, in her own world, she was the daughter of billionaires. And it showed.
Thomas reappeared a moment later, hands empty, and slipped out of the house without a word.
Jenny and Anastasia were now alone.
The brunette smiled faintly and patted the cushion beside her. “Please, sit.”
It sounded like an invitation, but something in her tone made it feel almost like an instruction.
Jenny settled on the sofa, keeping a half-meter of space between them. That’s when she noticed the slim folder on the coffee table, positioned neatly in front of Anastasia’s seat. A pen rested on top of it.
She leaned forward just enough to read the header on the first page.
Consent Agreement...
Her brows knitted. “Uh ... what’s this?”