The Devil's Wager: Taboo Step-Sibling Seduction

Marcus Holloway stood at the floor-to-ceiling windows of his father's penthouse apartment, watching the late afternoon California sun cast golden rays across the UCLA campus below. At twenty-two, he was in his final year of business school, cocky and confident with the kind of athletic build that came from years of rowing crew and the kind of face that made sorority girls stutter when he approached them at parties. His dark hair was tousled in that perfectly imperfect way, and his gray eyes held a perpetual glint of mischief.

But right now, those eyes were fixed on something far more interesting than the coeds sunbathing on the quad below. He was watching his step-sister.

Chloe Holloway—technically Chloe Van Der Berg since she'd kept her mother's maiden name after the marriage—was twenty years old and the bane of Marcus's existence. She was also, unfortunately for his sanity, the most fuckable woman he'd ever laid eyes on. Standing at five-foot-six with curves that could make a priest reconsider his vows, Chloe had long honey-blonde hair that cascaded down her back in loose waves, bright green eyes that sparkled with intelligence and cruelty in equal measure, and a mouth that was perpetually curved into a knowing smirk.

She was currently lounging on the balcony in a bikini so small it could have been made of dental floss and prayer, her toned legs stretched out on a lounge chair as she scrolled through her phone. The tiny triangles of electric blue fabric barely contained her full, perky breasts—natural D-cups that defied gravity and logic—and the bottom was cut so high on her hips that Marcus could see the toned planes of her lower abdomen disappearing into places he desperately wanted to explore.

"Take a picture, it'll last longer," Chloe called out without looking up from her phone, her voice dripping with that condescending tone she reserved specifically for him.

Marcus didn't bother pretending he hadn't been staring. That was part of their game, after all. The constant push and pull, the barbed comments, the sexual tension that had been building for the three years since their parents had married and they'd been forced into this luxurious prison together.

"Just wondering how much fabric they had to sacrifice to make that thing," Marcus shot back, stepping onto the balcony with two beers in hand. He offered her one, which she took without thanks. "Seems wasteful. Could have made three normal bikinis with that material."

Chloe finally looked up, her green eyes locking onto his with an intensity that made his cock twitch involuntarily. She had that effect on him. She had that effect on everyone. It was part of what made her so dangerous.

"Jealous that you can't wear it, big brother?" She stretched languidly, arching her back so her breasts pushed against the flimsy fabric, her nipples hardening slightly in the cool breeze. "Or are you just mad that you can't have what's underneath?"

Marcus took a long sip of his beer, buying time to calm the rush of blood to his groin. This was how it always went with Chloe. She'd push, he'd push back, and they'd both go to their separate rooms to jerk off or finger themselves while imagining the other submitting completely.

"Please," he scoffed, leaning against the railing. "I've had better."

It was a lie and they both knew it. Marcus had slept with dozens of girls at UCLA—cheerleaders, grad students, even a professor's wife once—but none of them had ever satisfied the deep, gnawing hunger that Chloe inspired in him. It was the forbidden element, he told himself. The taboo family sex fantasy that made his dick harder than steel every time she walked around the apartment in those tiny sleep shorts that rode up her perfect ass.

Chloe sat up, swinging her legs over the side of the lounge chair, and Marcus tried not to stare at the way her thighs parted slightly, offering a teasing glimpse of the smooth skin that the bikini bottom barely covered. She was waxed bare, he knew. He'd seen her laundry once, found a receipt from a high-end spa for a "full Brazilian," and had jerked off six times that day imagining her spread out on a table while a stranger worked hot wax between her legs.

"You know what I think?" Chloe said, standing up and walking toward him with a predatory grace that made his heart hammer against his ribs. She stopped inches away from him, close enough that he could smell her perfume—something expensive and floral with undertones of vanilla and sex. "I think you're full of shit, Marcus. I think you want me so bad you can taste it. I think you lie awake at night imagining what my pussy feels like, what my ass would look like with your cock buried in it, what my lips would look like wrapped around your shaft while I stare up at you with those pretty green eyes."

Marcus's mouth went dry. She'd never been this direct before. This bold. The sexual tension between them had always been a game of shadows and innuendo, but right now, standing on the balcony with the Los Angeles sunset painting her skin in shades of gold and amber, Chloe was offering something else entirely.

"And if I do?" he asked, his voice dropping to a dangerous growl. "What then? You going to run to Daddy and tell him his son has impure thoughts about his precious little girl?"

Chloe laughed, a throaty sound that went straight to his cock. She reached out and traced a finger down his chest, her nail scraping lightly over his t-shirt, following the line of his abdominal muscles down to where they disappeared into his jeans. She stopped just above his belt, her fingertip resting against the buckle.

"I was thinking something more... mutually beneficial," she purred. "A bet. A wager. Something to finally settle this little... rivalry... between us."

Marcus raised an eyebrow, intrigued despite himself. He and Chloe had made bets before—stupid things, like who could seduce a particular professor first, or who could steal the most panties from the sorority house across the street. But something in her tone told him this was different. This was the big one.

"I'm listening," he said.

Chloe stepped back, putting enough distance between them that Marcus could breathe again. She picked up her beer and took a long drink, her eyes never leaving his. When she spoke, her voice was all business, the seductive purr replaced by the sharp intelligence that had made her a straight-A student in the psychology department.

"There's a girl," Chloe said. "Emma Caldwell. You know her?"

Marcus frowned, searching his memory. The name rang a bell. "The pastor's daughter? The one who transferred from Bible college?"

"The very same," Chloe confirmed with a shark-like smile. "Sweet little Emma. Twenty years old, never been kissed—well, not properly—virgin in every sense of the word. She's been saving herself for marriage, you know. Wears a purity ring and everything. Goes to church three times a week, volunteers at the homeless shelter, the whole nauseating package."

"And?" Marcus prompted, though he was starting to see where this was going.

"And I bet you can't fuck her," Chloe said bluntly. "I bet that with all your charm, all your experience, all your 'Duncan family seduction techniques,' you can't get that innocent little virgin to spread her legs for you in the next thirty days."

Marcus laughed, a genuine sound of amusement. "That's it? That's the bet? Chloe, I've seduced harder targets than some repressed religious girl. This is easy money."

"Ah, but here's the catch," Chloe said, holding up a finger. "You can't just fuck her. Anyone can get a girl drunk and take advantage. No, you have to make her want it. You have to make her beg for it. She has to willingly surrender her virginity to you—no coercion, no trickery, no alcohol-fueled 'mistakes.' She has to consciously choose to let you pop her cherry, knowing exactly what she's doing. And you have to do it in a way that makes her fall head-over-heels in love with you, convinced you're her soulmate, her future husband, the man she's been saving herself for."

Marcus's smile faltered slightly. That was harder. Much harder. Seducing a virgin was one thing—seducing a virgin who thought she was saving herself for marriage, making her believe he was the one, that required a level of manipulation and acting that even he found daunting.

"And if I succeed?" he asked.

Chloe's smile widened, and Marcus felt a chill run down his spine. That smile promised either heaven or hell, and he wasn't sure which.

"If you succeed," she said, her voice dropping to a whisper, "you get me. Any way you want me. Any hole. Any position. Any... perversion... you've been jerking off to in the shower while imagining it's me you're fucking instead of your hand."

Marcus's cock surged to full hardness so fast it was almost painful. He shifted uncomfortably, trying to adjust himself without being obvious about it. Chloe noticed anyway, her eyes dropping to the obvious bulge in his jeans, and her smile turned triumphant.

"For one night," she continued. "Twenty-four hours where I'm your complete and total slut. I'll do anything you want, Marcus. Anything. You want to fuck my ass? It's yours. You want to come on my face and make me lick it up like a good little girl? I'll beg for it. You want to tie me up and use me as your personal fucktoy for a whole day? I'll bring the ropes."

"And if I fail?" Marcus asked, his voice rough with arousal.

Chloe's eyes glittered with dark delight. "If you fail, dear brother, you become mine. For the next year—three hundred and sixty-five days—you are my personal servant. My slave. You'll do whatever I say, whenever I say it. You'll clean my room, do my laundry, drive me wherever I want to go. And..." she paused, letting the anticipation build, "...you'll service me sexually whenever I demand it."

Marcus blinked. "Service you?"

"That's right," Chloe said sweetly. "If I want you to eat my pussy for three hours while I study for exams, you'll do it. If I want you to fuck me with a strap-on while I call you names, you'll do it. If I want to invite my friends over and make you strip for us, make you jerk off while we laugh at you, make you eat creampies from my freshly-fucked pussy... you'll do it. For a year, Marcus. A whole year of being my bitch."

The image sent a confusing rush of arousal through Marcus's body. He'd never considered submission before—he was always the dominant one, the one in control—but something about the idea of Chloe owning him, using him for her pleasure, made his dick throb painfully against his zipper.

"You're on," he said, extending his hand.

Chloe took it, her grip firm and warm, and they shook on it. The deal was sealed.

"You have thirty days," she reminded him. "Starting tomorrow. And Marcus?"

"Yeah?"

"If I find out you cheated—if you drugged her, or blackmailed her, or did anything other than seduce her properly—I win by default. And I'll make your life a living hell."

Marcus nodded, already planning his approach. Emma Caldwell. The innocent virgin. His ticket to finally tasting his step-sister's forbidden fruit.

"I won't need to cheat," he said confidently. "By this time next month, I'll have that little church girl screaming my name while I take her virginity. And then, little sister, I'm going to spend an entire day making you regret ever making this bet."

Chloe laughed, a sound like silver bells. "We'll see about that, big brother. We'll see."

Emma Caldwell was exactly as advertised.

Marcus spotted her the next morning at the campus coffee shop, sitting alone at a corner table with her nose buried in a textbook. She was pretty in a wholesome, girl-next-door way—long chestnut hair pulled back in a simple ponytail, minimal makeup that couldn't quite hide the constellation of freckles across her nose, and wide hazel eyes that seemed to take in the world with innocent wonder.

She was dressed modestly by modern standards—a floral sundress that fell to her knees, a cardigan despite the warm weather, and sensible flats. But Marcus could see the shape of her body beneath the conservative clothing—full breasts that strained slightly against the fabric of her dress, a narrow waist that flared into curvy hips, and legs that, while covered, hinted at toned muscle beneath.

Most importantly, she wore a simple silver ring on her left hand. The purity ring. Her promise to God and her future husband that she would remain untouched until marriage.

Marcus ordered two coffees—black for him, herbal tea for her, based on Chloe's research—and approached her table with his most charming smile.

"Mind if I sit?" he asked, setting the tea down in front of her. "You looked like you could use a break from whatever heavy reading you're doing."

Emma looked up, startled, and Marcus got his first real look at her eyes. They were beautiful—large and expressive, with thick lashes and a warmth that seemed to radiate from within. But there was something else there too. A loneliness. A hunger for connection that she probably didn't even recognize in herself yet.

"Oh, um, thank you," she said, her voice soft and musical. "But I didn't order this."

"I know," Marcus said, sliding into the chair across from her. "Call it a random act of kindness. Or a bribe to let me sit here. This place is packed and you're the only one with an empty chair."

It was a lie—the coffee shop was half-empty—but Emma didn't seem to notice. She looked around as if seeing the room for the first time, then back at Marcus. A faint blush colored her cheeks.

"I suppose that would be alright," she said. "I'm Emma."

"Marcus," he replied, extending his hand. She shook it, her grip soft and tentative. "And before you ask, yes, I'm one of those Holloways. My father owns half of downtown Los Angeles."

Emma's eyes widened. "Oh! I didn't—I mean, I wasn't going to ask. I don't really pay attention to... that sort of thing."

"Which is refreshing," Marcus said honestly. "Most people hear my last name and immediately start calculating how much money they can get out of me."

They talked for an hour. Marcus kept it light and friendly, asking about her major (English literature), her interests (poetry, volunteering, horseback riding), and her goals (teaching, eventually). He learned that she had transferred from a small Christian college in Texas because her father had taken a position as the new campus chaplain at UCLA. He learned that she had three older brothers who had teased her mercilessly growing up, which explained her slight shyness around men. He learned that she had never had a boyfriend, had never been on a real date, and had certainly never been kissed.

"That's... unusual," Marcus said carefully, swirling his coffee. "A beautiful girl like you. I would have thought guys would be lining up."

Emma's blush deepened, spreading down her neck and disappearing beneath the collar of her cardigan. "I told you, I was at an all-girls school. And before that... well, my father is very protective. And I have my faith. I'm waiting for the right person. Someone who understands that... that I'm not just looking for fun. I'm looking for forever."

Marcus nodded solemnly, projecting understanding and respect while internally calculating his approach. She wanted romance. She wanted a fairytale. She wanted Prince Charming to sweep her off her feet and prove that he was worth breaking her vows for.

He could be Prince Charming. He could be the best damn Prince Charming she'd ever met.

Over the next two weeks, Marcus launched a campaign of seduction that would have made Casanova jealous. He was everywhere Emma was—at the library when she studied, at the coffee shop when she took breaks, "accidentally" bumping into her between classes. He remembered everything she told him—her favorite flowers (peonies), her favorite author (Jane Austen), her favorite ice cream flavor (mint chocolate chip)—and used that knowledge to craft perfect moments of connection.

He brought her peonies when she was stressed about an exam. He quoted Austen to her in the quad, making her laugh with his terrible British accent. He took her for ice cream and walked her home, never pushing for more than she was willing to give, always the perfect gentleman.

And slowly, inevitably, Emma began to open up to him.

"I've never met anyone like you," she admitted one evening, two weeks into their... friendship? Courtship? Marcus wasn't sure what to call it yet, but he knew he was making progress. They were sitting on a bench overlooking the botanical gardens, the sunset painting the sky in shades of pink and orange. "Most guys, they... they want things. They get impatient. But you're different. You actually listen to me."

"That's because you're worth listening to," Marcus said, taking her hand. It was the first time he'd initiated physical contact beyond casual touches, and he felt her tense slightly before relaxing. Her hand was small and warm in his, her fingers delicate. "Emma, I know we haven't known each other long, but I feel like... like I've been waiting my whole life to meet you. Does that sound crazy?"

She looked up at him, her hazel eyes wide and vulnerable. "No," she whispered. "It doesn't sound crazy. I feel the same way."

Marcus leaned in slowly, giving her every opportunity to pull away. She didn't. Her eyes fluttered closed, her lips parted slightly, and Marcus captured her mouth in a gentle, lingering kiss.

It was chaste by his standards—just lips meeting, no tongue, no pressure—but Emma trembled against him, her hand clutching his shirt as if she were drowning and he was the only thing keeping her afloat. When they pulled apart, her eyes were shining with unshed tears.

"I've never..." she started, then stopped.

"I know," Marcus said softly. "We can go slow. Whatever pace you need, Emma. I'm not going anywhere."

It was the truth, he realized with a start. For all that this had started as a bet, as a means to an end, he was actually starting to care about Emma. She was sweet and genuine in a way that his world rarely allowed. She made him want to be better, to deserve the trust she was placing in him.

But then he thought of Chloe. Of the bet. Of what awaited him if he succeeded—or if he failed.

And he pushed his doubts aside and kissed Emma again, deeper this time, coaxing her mouth open with gentle pressure until her tongue tentatively touched his. She tasted like mint and innocence, and Marcus felt a surge of possessiveness that had nothing to do with the bet and everything to do with the woman in his arms.

Chloe was watching.

Marcus knew it even before he saw her, sitting at a table across the quad, sunglasses hiding her eyes but not the smirk on her face. She'd been observing his progress with Emma, he was sure of it. Checking in to make sure he wasn't cheating, that he was following the rules of their bet.

He was at the three-week mark, and things with Emma had progressed significantly. They were officially dating now—boyfriend and girlfriend, as she'd shyly confirmed to her father over Sunday dinner. They'd done everything but the actual deed—heavy petting that left Emma flushed and breathless, Marcus bringing her to orgasm with his fingers while she clutched at him and whispered his name like a prayer. She'd even touched him, once, her small hand wrapping around his cock with trembling uncertainty, her eyes wide as she felt him throb in her palm.

But she wouldn't go further. Not yet. She was still holding onto her virginity, still convinced that she needed to wait for marriage, even as her body begged for release.

Marcus was running out of time. He had one week left to seal the deal, and he was starting to worry that he wouldn't make it.

"She's got you twisted up, doesn't she?" Chloe's voice purred in his ear as he walked past her table.

Marcus stopped, turning to face his step-sister. She was dressed in a white sundress that should have looked innocent but somehow managed to be obscene, the fabric thin enough that he could see the outline of her nipples beneath, hard and prominent.

"Emma's none of your business," Marcus said coldly.

"Oh, but she is," Chloe replied, removing her sunglasses and fixing him with those piercing green eyes. "She's the key to our little wager. And from where I'm sitting, dear brother, you're losing. Badly."

"I'm making progress," Marcus insisted. "She's close. I can feel it."

"Can you?" Chloe stood up, stepping close enough that Marcus could smell her perfume—that same vanilla-sex scent that drove him crazy. "Or are you starting to develop actual feelings for the little virgin? Is that the problem, Marcus? Have you fallen for your mark?"

"Fuck off, Chloe."

She laughed, not offended in the least. "Here's what I think. I think you're too soft with her. Too gentle. Emma Caldwell doesn't need a nice guy, Marcus. She needs someone to take control. Someone to make the decision for her so she doesn't have to feel guilty about it. She's been repressed her whole life—what she needs is to be properly fucked, not romanced."

"And I suppose you have a suggestion?" Marcus asked sarcastically.

Chloe reached into her purse and pulled out a small vial of clear liquid. "Rohypnol," she said casually. "Odorless, tasteless, mixes perfectly with wine. One drop and she'll be compliant as a doll. She won't remember a thing, but her virginity will be gone, and you'll win our bet."

Marcus stared at the vial, then at his sister, disgust warring with temptation. "You said no drugs. That was the rule."

"I said you couldn't cheat," Chloe corrected, slipping the vial into his jacket pocket before he could protest. "I'm not saying use it. I'm just saying... options exist. If you want to win."

She walked away, her hips swaying hypnotically, leaving Marcus standing there with illegal drugs in his pocket and a war raging in his conscience.

He didn't use the drug. Of course he didn't. But the fact that Chloe had offered it, that she'd been willing to compromise her own rules to ensure he either won or lost... it made him suspicious.

And it made him more determined than ever to succeed on his own terms.

The breakthrough came on day twenty-eight, with only two days left on the bet.

Marcus had taken Emma to a charity gala—one of his father's events, filled with wealthy donors and champagne fountains. Emma had been nervous, overwhelmed by the glamour and sophistication of the crowd, and Marcus had spent the evening playing the perfect protector, keeping her close, shielding her from the more aggressive social climbers, making her feel safe and cherished.

They'd danced, Emma fitting perfectly in his arms, her head resting against his chest as they swayed to a slow song. Marcus had whispered in her ear—promises of forever, of love, of a future together that was brighter than anything she'd ever dreamed.

"Marcus," she'd whispered, looking up at him with those wide, trusting eyes. "I love you. I know it's fast, I know we haven't known each other long, but I do. I love you."

"I love you too, Emma," he'd replied, and meant it. "You're everything I've been looking for. Everything I didn't know I needed."

They'd left the gala early, taking a car back to his apartment—his father's penthouse was empty, Chloe having gone away for the weekend with friends. Marcus had poured them wine, they'd talked about their future, about marriage and children and a life together.

And then Emma had stood up, her hands trembling slightly, and removed her cardigan. Then her dress. Then her undergarments, until she stood before him in nothing but her purity ring, her body pale and perfect in the moonlight streaming through the windows.

"I want you to have it," she said, her voice shaking but determined. "My virginity. I want to give it to you, Marcus. I know you're the one. I know it in my heart."

Marcus stood up, crossing the space between them and taking her in his arms. She was trembling, he realized, terrified and aroused in equal measure. He kissed her gently, reverently, then swept her up and carried her to his bedroom.

He made love to her slowly that first time, taking care to prepare her properly, using his mouth and fingers to bring her to the edge of orgasm before he even thought about entering her. When he finally pushed inside, breaking through her hymen with a single, careful thrust, Emma cried out—not in pain, but in wonder, her nails digging into his back as she clung to him.

"Marcus," she gasped, her eyes wide. "Oh God, Marcus, I never knew... I never imagined..."

He moved inside her, setting a rhythm that was slow and deep, watching her face for any sign of discomfort. But there was none—only pleasure, only love, only the dawning realization of what her body was capable of feeling.

They made love three times that night. The first time was gentle, exploratory, tender. The second time was more passionate, Emma gaining confidence and beginning to move with him, her hips rising to meet his thrusts. The third time was wild, almost desperate, Emma begging him to go harder, faster, deeper, until she was screaming his name and clawing at his back, her orgasm ripping through her with such force that she nearly blacked out.

Afterward, they lay tangled together, sweat-slicked and breathless, Emma's head on Marcus's chest as he stroked her hair.

"Was it... was it okay?" she asked shyly.

"It was perfect," Marcus assured her. "You're perfect, Emma. I love you."

"I love you too," she whispered. "Forever."

Marcus held her close, but even as he basked in the afterglow, he felt a pang of guilt. He'd won the bet. He'd seduced the virgin, made her fall in love with him, taken her cherry. In two days, he would collect his prize—twenty-four hours with Chloe, doing whatever he wanted to her willing body.

But as he looked down at Emma, at the peaceful expression on her face as she drifted off to sleep in his arms, he wondered what the cost of that victory would be.

Marcus returned to the penthouse on day thirty, exactly one month after the bet had been made. Emma was at class—he'd left her with a kiss and a promise to call later, his heart heavy with the knowledge of what he was about to do.

Chloe was waiting for him in the living room, dressed in a silk robe that left little to the imagination. She'd clearly been anticipating this moment.

"Well?" she asked, though she already knew the answer. She could see it in his face, in the satisfied glow that radiated from him.