Cover of The Proposition

The Proposition

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I hope in reality did not give Ashlee or Kevin authorization for this lesson! The apartment smelled like stale... September 14th, 2025 The apartment smelled like stale pizza and cheap beer. Friday night leftovers. Ashlee sat curled at one end of the worn corduroy couch, the flickering blue light of some forgettable sitcom washing over her face. Kevin sprawled at the other end, scrolling his phone, the silence thick and comfortable, just background noise. "Hey, Kev?" He grunted, not looking up. "Hmm?" She shifted, tucking her feet under her. The silence stretched, punctuated only by the tinny laugh track. He finally glanced over. Her brow was furrowed, chewing on her bottom lip. Her thick, dark red hair was piled messily on her head, escaping strands framing her face. That tiny gap between her front teeth was visible as she worried her lip. "You okay, Ash?" She took a shaky breath. "Okay, don't freak out. Seriously." Her voice was low, hesitant. "But… I need a favour. A… big one. Like, monumentally awkward big." Kevin put his phone down, fully attentive now. Ashlee wasn't usually this… fidgety. "Shoot. Can't be worse than the time you asked me to help bleach your roots and we nearly gassed ourselves." He tried for a grin. She didn't smile back. Instead, she pulled her knees up to her chest, hugging them. Her oversized band t-shirt slipped off one shoulder. "It's about… um… sex stuff." Kevin blinked. Sex stuff? With Ashlee? They were roommates, friends, but their boundaries were usually strictly platonic. "O…kay," he said slowly. "Hope giving you girl advice or something?" Hope, his girlfriend, was Ashlee’s friend too. The connection made sense. "No. Not Hope." Ashlee squeezed her eyes shut for a second, then opened them, meeting his gaze directly. Her green eyes were wide, earnest. "It's about me. And… doing it. Specifically, sucking dick." The word hung in the air, stark and crude against the mundane backdrop of the sitcom. Kevin felt his jaw loosen slightly. What the actual fuck? He stared at her, speechless. Ashlee, with her fiery hair and those Madonna-gap teeth, her curvy frame usually radiating confidence, looked utterly vulnerable. Fragile, even. Her cheeks flushed crimson. "See? Awkward. Told you." She rushed on, the words tumbling out. "Mason comes back next week. He's been gone a month. And… we haven't… done that yet. Oral, I mean. We've done other stuff, obviously, but…" She trailed off, looking down at her fingers picking at the co

Chapter 3: I hope this truck into a psych

The silence in the apartment felt different now, thick and accusatory. Kevin jumped when his phone vibrated on the coffee table, Hope’s name flashing on the screen. Her voice was a rushed, panicked whisper. “It’s my aunt, in Sarasota. She took a turn.” He drove her to the airport, the car filled with the weight of everything unsaid. Under the harsh terminal lights, she looked small. “I am so, so sorry for how I acted the other day,” she blurted out, her eyes glistening. “It was the pills, and the stress… I was completely out of line.” He pulled her into a brief, tight hug. “It’s okay,” he murmured into her hair. “Just go. Family first.” He watched her disappear through the security gate, a knot of guilt tightening in his chest. Back in the car, the silence was a relief. He texted Ashlee: She’s gone. Family thing in Florida. The reply was almost instant: How long? He started the engine, a dark, liberating thought taking root. A few days, he typed, pulling into traffic. The place is all ours.

The front door clicked shut behind him, sealing them in a bubble of shared complicity. Ashlee was already on the couch, one leg tucked under her, a slow smile spreading as she looked him over. "So, a family emergency in Florida?" she asked, her voice laced with a knowing amusement that made the lie feel solid and real.

He tossed his keys onto the cluttered coffee table, the sound sharp in the quiet room. "She bought it completely," he said, running a hand through his hair. The faint, lingering scent of her coconut shampoo mixed with the smell of old books, a familiar combination that now felt charged with possibility.

She unfolded herself and stood, closing the distance between them with a few silent steps on the worn rug. "No more lessons needed," she murmured, her green eyes holding his, "but I think we both know that was bullshit." Her fingers traced the line of his jaw, a light, testing touch. He caught her wrist, his grip not gentle, and felt her pulse jump against his thumb. "This is fucked up," he stated, but he was already pulling her closer. "Tell me to stop." She laughed, a low, throaty sound, and rose onto her toes. "I don't want to stop," she whispered against his mouth, her breath warm. The lamp flickered, casting long, dancing shadows across the walls as he backed her toward the same couch where it all began.

His hands were on her hips, her back arching into the familiar dip of the cushions. The worn fabric smelled of them now, of that first secret lesson and every reckless thought since. Her mouth found his neck, a hot, open-mouthed kiss that sent a jolt straight through him.

He froze.

His body went rigid, his grip on her loosening. "Wait." The word was a rough exhale, torn from somewhere deep. Ashlee stilled, her breath warm against his skin. "What?" she whispered, her voice frayed with confusion and desire.

Kevin pulled back just enough to see her face in the flickering light. His own was a mask of conflict, eyes shadowed with doubt. "What have you learned from the lesson, Ashlee?" he asked, the question sounding hollow and strange.

He ran a hand over his face, trying to wipe away the image of Hope’s trusting smile at the airport. "I know you love Hope," he continued, the words feeling like glass in his throat. "And I care for her deeply." The weight of the lie about her aunt pressed down on him, suffocating. "Maybe we should reconsider," Kevin said, conflicted as hell.

Ashlee’s expression hardened, a flash of irritation in her green eyes. "I learned enough," she said, her tone defensive and sharp. "Mason will be happy, which was the whole point." She shifted away from him, putting a cold inch of space between their bodies. "Don’t use her as an excuse now."

The challenge hung in the air between them, a dare. He looked at her, at the stubborn set of her jaw and the invitation in her eyes, and felt the fragile wall of his resolve begin to crack.

He could still feel the ghost of her mouth on his neck, a brand of pure temptation. Ashlee watched the war play out behind his eyes, the internal struggle that made his breath catch. Then, with a deliberate slowness, she placed her palm flat against his chest and pushed herself away, creating a cold, sobering distance between them on the couch.

“You are a good man, Kevin,” she said, her voice soft and startlingly clear, all the previous heat gone. She tucked a strand of thick red hair behind her ear, her gaze steady and unnervingly sincere. “And I need to be an incredible friend to Hope.”

She stood up, smoothing her shirt down with hands that didn’t quite tremble. “We got carried away, both of us, and it was a mistake.” The finality in her tone was like a bucket of ice water. “We can simply pretend that nothing ever happened.”

She didn’t wait for his reply, turning toward the hallway that led to her room. The floorboard creaked under her weight, a familiar sound that now felt like a period at the end of a sentence. Kevin stared at the empty space she left behind, the faint scent of coconut hanging in the air like a taunt.

The faint, sweet scent of her shampoo clung to the fabric of the couch, a ghost in the lamplight. He could still feel the heat of her palm where it had pressed against his chest, a push that felt more like a pull. What the hell was that?

One minute she was all heat and invitation, the next she was framing his hesitation as virtue. She played him. The realization was a cold stone in his gut. She’d taken his moment of doubt and twisted it into her own noble exit, leaving him alone in the wreckage of their shared secret.

His phone buzzed, shattering the silence. Hope’s name glowed on the screen, a jolt of pure guilt. He took a breath, forcing his voice into something steady. "Hey, babe. How's your aunt?"

"It's… a lot," she said, her voice thin and stretched. "The doctors are talking about a longer-term care facility." He closed his eyes, pinching the bridge of his nose. "I'm so sorry, Hope." A beat of silence passed, filled only by the staticky sound of her breath. "I miss you," she whispered. "I feel so far away."

"Me too," he said, the lie tasting like ash. He could still smell the coconut in the air. "Just focus on your family. I've got everything here under control." She let out a shaky sigh. "I know. I should go. I love you, Kevin." The words hung in the dead air long after the call ended. I love you, too. He couldn't say it. The silence in the room was absolute, and it was entirely his own making.

The flickering lamp cast long, shifting shadows that seemed to mock the stillness. He could still smell her on the cushions, that cheap coconut scent now inseparable from the taste of his own betrayal. His phone felt heavy in his hand, a cold, guilty weight.

He stood abruptly, the worn rug bunching under his feet. The silence was a physical pressure in his ears, broken only by the frantic rhythm of his own heart. He needed to look at her, to see the truth in her eyes after that calculated retreat.

His footsteps were unnaturally loud on the creaking floorboards as he moved down the hall. Her door was slightly ajar, a sliver of yellow light cutting through the dim hallway. He pushed it open without knocking, finding her perched on the edge of her bed, calmly applying nail polish.

She didn’t look up, focusing on a steady stroke of crimson. “Change your mind?” she asked, her voice flat and unsurprised. He leaned against the doorframe, crossing his arms over his chest. “What was that, Ashlee?”

“That was me saving us from a really stupid mistake,” she said, finally meeting his gaze. Her eyes were clear and sharp, devoid of the heat from minutes before. “You were about to crack, and I don’t do guilt trips.”

“You don’t get to play the noble friend,” he shot back, his voice low. “Not after what happened on that couch.” She blew gently on her nails, a small, dismissive action. “The lesson is over, Kevin. Mason comes home soon.”

The silence stretched between them, thin and sharp as a razor. Kevin’s jaw tightened, the mention of Mason’s name a cold splash of reality. Ashlee watched him, her expression unreadable in the dim light from the hallway.

Then, a slow, knowing smile curled her lips. "Hey, Kev," she said, her voice dropping to a conspiratorial whisper. "Just so you know, you really have a beautiful dick."

Kevin’s breath hitched, the crude compliment landing with the force of a physical blow. Is she trying to dismantle me with praise? he thought, his mind reeling from the sudden, intimate focus. This isn’t about Mason anymore.

It’s perfect in every way, Ashlee’s mind supplied, a sharp, clinical assessment beneath the lust. And the amount of cum you generate when you orgasm is exceptional. She saw the shock in his eyes and felt a thrill of power. Let him remember that when he’s with her.

The air in the room felt charged, thick with the scent of her nail polish and their shared deceit. Kevin could only stare, his earlier resolve crumbling under the weight of her blatant admiration. "Exceptional," she repeated, letting the word hang, a challenge and an invitation.

His own traitorous body responded, a flush of heat spreading through him. She’s mapping my insecurities and feeding my ego, he realized, even as the memory of her mouth clouded his judgment. The lamp from the living room cast a long, distorted shadow of them against the wall.

"Ashlee," he managed, his voice rough. She simply smiled, her green eyes gleaming with triumph.

The triumph in her eyes was a physical force, pushing him back a step into the dim hallway. That cheap, cloying coconut scent from her shampoo followed him, a taunt he could taste at the back of his throat. “Exceptional,” she repeated, the word a soft, devastating weapon aimed directly at his crumbling resolve.

He turned and walked away, his footsteps echoing in the narrow space. Each creak of the floorboards felt like a condemnation. Back in the living room, the flickering lamp seemed to pulse with a sickening rhythm, casting long, distorted shadows that danced across the same couch where it all began.

He could still feel the ghost of her weight in the cushions, the memory of her choked gags a corrosive whisper in his mind. His phone, heavy with Hope’s trusting words, felt like a block of ice in his pocket. He stood there, trapped between the woman he betrayed and the one who dissected his body with such clinical praise.

From down the hall, her voice cut through the silence, sharp and clear. “You know where I am if you want to finish what we started.” The offer hung in the air, naked and undeniable. It wasn’t an invitation anymore; it was a test of what little character he had left.

He didn’t answer.

The silence from the hallway was a verdict. It left him standing in the living room, the flickering lamp making the shadows of the mismatched furniture seem to breathe. He was a fool, and she knew it.

That clinical praise echoed, dissecting him. Exceptional. The word was a hook in his gut, pulling him toward her door. It seemed a profound waste, this willingness of hers, a secret door left open just for him while Hope was safely distant. His love for Hope was a solid, real thing, but this was a different kind of hunger, sharp and immediate.

He could almost feel the weight of Ashlee’s curvy figure under his hands, a topography he’d only briefly mapped. The guilt was a cold stone in his pocket, right next to his phone. Each second he stood there, paralyzed, felt like a failure to choose a side of himself.

Each second he stood there, paralyzed, felt like a failure to choose a side of himself. He moved then, his feet carrying him down the hall as if pulled by a string tied to his spine. Her door was still ajar, that same sliver of light, and he pushed it open to find her exactly as he’d left her, a statue of waiting calm.

I’M NOT SURE WHAT IT IS, he thought, the words a frantic, internal scream as his eyes traced her form. SHE IS KIND OF THICK - CURVED BODY - THICK ASS THAT IS FORM - BUT THOSE PERFECT C SIZE BRESTS AND THOSE RED PILLOW LIPS AND THAT RED HAIR… He watched her run her tongue over her teeth, and he saw it, THE GAP BETWEEN HER TOP TWO TEETH. It was that specific, vulnerable detail, coupled with THAT LOW SELF ESTEEM THAT HE WANTED TO HELP RESTORE, that finally snapped the last thread of his resistance. MAYBE THE WRONG THING WAS NOT TO HELP HER, the thought arrived, fully formed and perfectly twisted. HE WOULD NOT BE A REAL FRIEND IF HE DID NOT MENTOR HER AND BUILD UP HER SELF ESTEEM.

“Changed your mind?” she asked, her voice a low hum. He didn’t answer with words. He crossed the room in three long strides, the floral pattern of her quilt a blur beneath his knees as he joined her on the bed. His hand, which had felt so heavy with indecision moments before, now cupped the back of her head, his fingers tangling in the thick, dark red silk of her hair. He pulled her to him, and her mouth opened under his, a soft, yielding sigh escaping into the space between them. This wasn't a lesson anymore; it was a surrender.

He kissed her with a bruising intensity that tasted of mint and betrayal, his hands mapping the curve of her waist through the thin fabric of her shirt. When he finally pulled back, his breath was ragged. "We need rules," he whispered, the words gritty against her lips. "Or this burns down everything."

He laid it out in a low, hurried monotone, a stark blueprint for their deception. Short trips allowed for calculated risk, but extended holidays meant a complete shutdown of their contact. "When Hope is here, you and I are nothing," he stated, his eyes locked on hers, demanding understanding. "We are roommates who share a microwave and nothing else."

Ashlee listened, her expression unreadable, her fingers tracing idle patterns on the quilt. "So I’m a scheduled intrusion," she said, her voice flat. "Sex only when she’s conveniently absent."

"It keeps you safe, it keeps me safe, and it keeps this secret," he countered, his jaw tight. "We do weekly check-ins. If either of us feels… too much, we hit pause immediately." He watched her process the cold architecture of the plan, the way it neatly compartmentalized her into a category. "This is the only way it works."

A slow, knowing smirk finally touched her lips. "Okay, professor," she murmured, her green eyes glinting in the dim light. She leaned in, her breath warm against his ear. "Then we should make this first session count." Her hand slid down his chest, past his belt buckle. "Before my curriculum ends."

His fingers tightened in her hair, a possessive anchor. "The curriculum just expanded," he growled against her neck, his breath hot. He reached into his jacket pocket, the leather creaking, and pulled out a sinister black object.

It was a ball gag, the thick silicone sphere looking impossibly large. "I bought you a gift," he said, his voice dropping to a low, instructional tone. "But you have to earn it."

Her eyes widened, flicking from the gag to his face. "You need to keep my dick buried in your throat for a full sixty seconds." He held the gag up, letting the leather straps dangle. "If you can work up to that, conquer that fear, the gift is all yours."

A shaky breath escaped her, part apprehension, part thrill. "Sixty seconds?" she whispered, her voice already sounding raw. He merely nodded, his expression severe, the teacher setting a difficult final exam. "Let's see if you've been paying attention."

He didn't wait for her to agree. His hands were on her shoulders, pushing her down the bed until her head hung over the edge. The world inverted, the floral quilt a distant ceiling. He knelt before her, his buckle clinking as he freed himself.

The first touch of him against her lips was a familiar shock. She opened, taking him in, the memory of her first choked gags flooding back. He pushed deeper, past the point of comfort, until the head nudged the tight ring of her throat.

She gagged instantly, a wet, strangled sound. He didn't pull back. "Breathe through your nose," he commanded, his voice rough but steady. Her body tensed, fighting the reflex, tears springing to her eyes as he held himself there, stretching her.

He forced deeper, a brutal, unyielding pressure that made her throat convulse around him. Spit bubbled at the corners of her stretched lips, and her fingers clawed at the quilt. "Just breathe," he grunted, his own knuckles white where he gripped her hair, holding her in place for the relentless, slow count in his head. Her vision spotted at the edges, the inverted room swimming in a haze of tears and desperate, nasal breaths. He watched, mesmerized, as her body fought and then gradually, tremulously, began to accept the violation. A wet, surrendering sound vibrated through her, and he felt the tight ring of muscle give way. "That's it," he murmured, a flicker of something like pride cutting through the predatory focus. "Now you're getting it." He began a shallow, rhythmic pumping, each thrust a measured conquest of that newly opened space. Her gagging subsided into choked, gurgling swallows that traveled the entire length of him. He pulled out, glistening and slick, and her gasp for air was a ragged, grateful sob. "Forty-five," he stated, his voice cold and instructional as he wiped a strand of saliva from her chin. "Again." He didn't wait for her to ready herself, plunging back into the wet, yielding heat. This time, her body took him easier, a practiced, shameful acceptance. He fucked her throat with a steady, piston-like rhythm, the obscene, wet sounds filling the quiet room. "Fifty," he counted, his breath starting to hitch. He drove in to the hilt and held, burying himself completely in the spasming, hot darkness.

He held himself deep, the seconds stretching as her throat convulsed in wet, rhythmic pulses around his length. Her fingers scrabbled against the quilt, knuckles white, while tears traced hot paths through the spit shining on her skin. "Fifty-eight," he growled, his own control fraying at the edges as he watched her take it.

A guttural, surrendering moan vibrated through her, the sound muffled and obscene. He finally withdrew, his cock glistening and slick, leaving her gasping and shuddering on the rumpled sheets. "You took it all, you fucking did it," he breathed, his voice thick with a mix of awe and dark satisfaction.

She wiped her mouth with the back of her hand, her eyes bleary but sharp. "Give me the gag now," she demanded, her hoarse voice cracking with urgency. He handed her the leather straps, the black silicone sphere looking sinister in her trembling grasp.

"Open up," he instructed, his tone leaving no room for hesitation. She parted her lips, and he fitted the ball into her mouth, the straps snug behind her head. "Now, let's see how quiet you can be," he said, pushing her onto her stomach.

He entered her from behind in one brutal, fluid motion, her choked cry stifled by the gag. Each thrust was a punishing rhythm, the slap of skin echoing in the small room. Her muffled screams were a vibration against his palm when he gripped her hip, driving deeper.

"Remember the couch?" he grunted, his breath hot on her neck. "This is so much better." She nodded frantically, her body arching, every muscle taut with a shameful, rising pleasure. He could feel her tightening around him, her earlier lessons forgotten in this raw, filthy act.

"Come for me, Ashlee," he commanded, his pace becoming erratic, desperate. And she did, a silent, shaking climax that ripped through her as he emptied himself inside with a low, guttural roar.

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