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Wicked Pleasures [Steamy Short Stories]
Wicked Pleasures [Steamy Short Stories]
Author: Jon Faith

An Enticing Proposition 1

Author: Jon Faith
last update Last Updated: 2025-10-29 16:19:50

“So, apart from dad dying and ruining the family’s business, he has an unpaid debt?” 

Ava Sullivan’s eyes widened with disbelief as she sat across from her mother in their small dining room. The revelation was nothing short of astonishing, and it felt like a cruel twist of fate on top of their family’s existing hardships.

Ava, at the age of twenty-two, was a strikingly beautiful woman. Her long, curly black hair framed her face with captivating blue eyes, and her physique was undeniably alluring. 

With an hourglass figure, she boasted a naturally full-figured chest, curvaceous buttocks, a flat stomach and a tiny waist, all harmoniously complementing her stature, standing at a mere five feet and four inches. 

Her body was a source of pride and confidence, a testament to her genetics and perhaps a nod to her disciplined self-care routines.

She had grown up in a family of wealth and privilege, enjoying the comfort and security that such a life offered. However, the course of her life was abruptly altered by a dramatic and unfortunate turn of events.

Not too long ago, tragedy struck the Sullivan family as Ava’s father met a gruesome end, subjected to a savage beating at the hands of unidentified assailants he had become entangled with. 

He had once been the pillar of responsibility, a man who steered their family company towards prosperity and success. 

However, one day they discovered that he was into gambling to the point of obsession.

It was this all-consuming vice that ultimately led to his downfall. 

The poker tables and high stakes had ensnared him, and as the debts piled up, so did the danger he placed himself in.

His life ended. Just like that.

Now, Ava’s mother, Caroline, bore the grim task of delivering another blow to their already-struggling family. 

The news that her late husband had an insurmountable debt was like an anchor threatening to drag them all under.

What more does he want from them?

The Sullivan family’s reputation had already been destroyed.

Their once-flourishing company crumbled under bankruptcy, and even their mansion, a symbol of their past affluence, had been lost. 

They were left with nothing but a litany of troubles, and now this crushing debt threatened to bury them deeper.

Caroline Sullivan, her mom, carried the weight of these troubles on her shoulders.

“I’m at a loss, darling, but the only way out seems to be working myself into the ground to pay off this debt,” Caroline admitted, her voice heavy with exhaustion and despair.

Ava regarded her mother with a mix of sympathy and concern, leaning forward as she inquired, “How much do we owe, Mom? Can the restaurant even handle a debt like this?”

Caroline blinked, her eyes filled with the weight of an unthinkable burden, and then softly confessed, “It’s an exorbitant sum, Ava. We’re facing a staggering fifty million dollars in debt.”

Ava gasped in shock. “Jesus! Fifty million?! Mom, that’s unimaginable! How did this happen?”

“It’s an amount that’s beyond our means, Ava,” her mother replied, a heavy sigh escaping her lips. “That’s why I’m going to attempt to reason with him, to plead for more time to repay.”

Ava’s brow furrowed in anxiety. “And who exactly is this person, Mom?”

“Travis Vanderbilt,” Caroline’s response came with a deep exhalation, her voice filled with a mix of frustration and fear, “He’s the one we owe this colossal debt to, and confronting him will be the most difficult part.”

Ava’s eyes widened as the name hit her ears like a bolt of lightning. Travis Vanderbilt, the man who owned the Diamond Group, a powerful and wealthy bachelor who embodied every woman’s wildest fantasies.

There was no denying it. Ava was one of those women who had, more than once, indulged in sensual daydreams about him.

In the privacy of her thoughts, she had conjured up images of him, his figure tall and statuesque, his handsome features gracing the pages of her imagination.

She hadn’t even laid eyes on him in real life, but that hadn’t stopped her from conjuring vivid mental scenarios that left her in a state of arousal more than once. 

Just the mere thought of him had led her to explore herself intimately in private.

He was the embodiment of desire, the blueprint of a man that girls dreamed of and boys envied. 

Towering and good-looking, with a pair of icy blue eyes that could freeze anyone in their tracks, broad shoulders that bespoke strength and charisma, and a mane of dirty blonde hair, meticulously coiffed to perfection. 

Travis Vanderbilt was the ideal male specimen, and Ava, like so many others, found herself yearning for him, even though the idea of being with him was more like a far-off daze.

Ava was briefly jolted from her day dreaming, mentally smacking herself as she realized the inappropriateness of her fantasies in such a difficult moment.

But then an audacious thought unfurled in Ava’s mind. “What if, Mom, I go to him tomorrow? I could approach him, talk to him, maybe even beg for an audience.”

Caroline’s eyes lit up with hope, and she nodded eagerly. “Yes, Ava, please do that. Plead with him to grant us an opportunity, to extend the time we have to repay our debt, okay?”

Ava responded with a nod, a smile gracing her lips as she contemplated the extraordinary prospect of meeting Travis Vanderbilt.

The mere possibility of seeing him in the flesh was enough to send ripples of desire through her core.

Her fervid fantasies about this man were, in all likelihood, unattainable dreams, but a chance to lay eyes on him in person would be a feast.

Just the thought of his face, hearing his voice, was sufficient to make her moist between her thighs and the electricity of anticipation coursed through her body.

She was aware of the age-old caution, ‘never meet your heroes,’ yet she couldn’t suppress the longing to witness this charismatic man up close, to ascertain if the attraction that had fueled her desires for so long would hold true.

As they concluded their meal, Ava couldn’t help but pray that this meeting would hold the potential to change her family’s future. 

She hoped, with every fiber of her being, that Travis Vanderbilt was not as unyielding as the media might portray him. 

She hoped he would be the savior they so desperately needed.

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  • Wicked Pleasures [Steamy Short Stories]   Anal Plumbing 6

    Karl shook his head, half-amused, half-stunned, silently wondering how the hell a woman like her ended up this depraved, but he didn’t care enough to ask.“Now,” Maya purred, voice still shaky but greedy, “fill my cunt too.”Karl gave a single nod. His right fist stayed buried deep in her still-pulsing asshole. Then he coated his left hand in more lube and lined it up at her dripping, swollen pussy.The moment he pushed, her cunt opened like it was welcoming him home, swallowing his fist in one smooth, greedy glide.Maya let out a soft, blissful sigh. “Mmm…”“Damn,” Karl muttered, genuinely awed. “Your pussy’s so fucking loose around my hand.”“It should be,” she answered casually, almost proudly. “After how many times it’s been used? Yeah… I’ve done a stupid amount of shit with this pussy.”Karl’s brows lifted, intrigue burning hotter in his eyes. “You don’t look like a street hooker. So what the fuck do you actually do?”Maya let out a shaky laugh, hips rocking slightly around both

  • Wicked Pleasures [Steamy Short Stories]   Anal Plumbing 5

    Maya reclined against the headboard, shoulders propped high on a thick stack of pillows, legs splayed obscenely wide. Her knees were pulled back toward her chest, feet planted flat on the mattress, putting her wet pussy and still-gaping asshole completely on display for Karl’s ravenous stare.She was practically vibrating with anticipation, eyes glassy and hungry, dying to feel those big, rough hands punching deep inside both her holes.“You absolutely sure about this?” Karl asked one more time, needing to hear it again.Maya nodded frantically, lips parted, breath coming fast. “Stop asking, Plumber. My holes can take it, trust me, they’re fucking impressive. Shove those massive hands in me already. Wreck me.”The raw, slutty desperation written all over her face made it impossible to doubt how badly she needed it.Karl let out a dark, amused chuckle, shaking his head like he couldn’t believe his luck.“Jesus Christ… you really are the filthiest, greediest slut I’ve ever gotten my ha

  • Wicked Pleasures [Steamy Short Stories]   Anal Plumbing 4

    Karl lounged back on Maya’s bed like he owned it, one arm folded behind his head, a lazy, smug grin spread across his face as she crawled up onto his naked body.She dragged both hands slowly over his hard, carved muscles, eyes heavy with lust. “Fuck, I love this body,” she murmured, voice thick and sultry. “All this muscle… makes me want to ride you so hard.”He smirked wider, letting her touch.She shifted slightly to the side, leaned down, and captured his mouth in a deep kiss while her hand wrapped firmly around his cock, giving him a slow, possessive squeeze while her tongue pushed past his lips.Karl kissed her back just as hungrily, lips parting, tongues meeting in a wet slide.However, Maya was the one leading, and she was so horny and needy that she kissed him harder, deeper, pressing her mouth against his with greedy insistence, tilting her head one way then the other. Her free hand roamed his torso restlessly over his ribs, along the tight planes of muscle, brushing his nip

  • Wicked Pleasures [Steamy Short Stories]   Anal Plumbing 3

    Maya turned away from him, dropping onto all fours. She spread her thighs wide, arched her back, and pressed her cheek to the floor.“Time to service my asshole, plumber,” she said, voice dripping with invitation.“As you wish.”Karl moved in behind her, hands clamping onto the full curves of her ass and spreading her open. He spat directly onto her tight ring, then lined himself up and drove straight in with one long, unrelenting push.Maya let out a soft, startled moan. “Oh… fuck, yes.”The sudden stretch burned so good it made her eyes roll and her hole fluttered wildly around the thick invasion.Then Karl’s fingers dug into her hips hard enough to leave marks, and then he started fucking her in earnest.“Ughhh, fuuuck!” Maya half-laughed, half-cried out in delight.Each thrust slammed home, balls slapping wetly against her soaked pussy with every punishing stroke. His thick shaft scraped along every slick, sensitive fold inside her, stretching her to the limit, stuffing her so f

  • Wicked Pleasures [Steamy Short Stories]   Anal Plumbing 2

    Karl’s slow, dangerous smile spread. “And you’re sure your asshole can handle my big tool?”Maya just smiled at him, using her eyes to rake his build like she couldn't wait to eat him.“Well, gonna need to open you up first,” he said, almost conversationally, as though he were still talking about pipes and fittings. “Can’t just force my way in. You understand?”Maya nodded. “I do. Except this hole doesn't need that much care, baby. You can force your way in however you want.”Karl studied her presented hole like he was inspecting premium-grade pipe. Without another word he lined up two thick fingers and shoved them straight into her asshole, knuckle-deep in one smooth, brutal push.Maya’s back arched hard. “Fuuuck… yes!”He twisted his fingers inside her, scissoring them wide, feeling how easily her well-used ring opened and swallowed him.“Hmm,” he grunted, pumping his fingers in and out a few times, listening to the wet squelch. “This line’s definitely seen some serious heavy-duty e

  • Wicked Pleasures [Steamy Short Stories]   Anal Plumbing 1

    The kitchen sink had been dripping for three days now.Not a dramatic gush, but a slow, maddening drop into the steel basin that drilled into Maya’s skull every time she tried to read, or work, or even think. She’d finally surrendered this morning, dialed the first emergency plumber Google promised would actually show up on a Saturday Then the doorbell finally rang after waiting.She opened the door in bare feet and an old cotton sundress the color of ripe peaches, thin enough that the afternoon light made it semi-transparent if she stood at the right angle.The man on her doorstep was not the middle-aged guy with a beer gut she’d braced for.And for two full seconds, she forgot how to breathe.He was tall, taller than the doorframe really required, shoulders wide enough that the navy work shirt looked painted on. And his dark hair was still damp, perhaps from a recent shower, his forearms roped with muscle. His handsome face had a faint shadow of stubble along his sharp jaw and st

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