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 1: The Unthinkable Favor

The flickering television painted shifting blue ghosts across Ashlee’s face as she twisted her hands in the fabric of her sweatpants. “I need you to teach me how to give head,” she blurted out, the words hanging in the pizza-scented air like a physical blow.

Kevin, who had been halfway to a sip of cheap beer, froze with the bottle an inch from his lips. His mind stuttered, a frantic, What the actual fuck? scrambling for purchase against the sheer absurdity of the request. Ashlee’s eyes, usually so defiantly green, were wide pools of raw, unvarnished terror.

He’s going to laugh, he’s going to think I’m a pathetic freak, Ashlee’s internal monologue screamed, her confidence shriveling under the weight of her inexperience. She watched his face, every micro-expression feeling like a verdict.

From the dark of the bedroom, a muffled sound seeped into Hope’s Ambien-haze, the voices weaving themselves into the fabric of a dream about arguing cats. Why are the cats talking about blowjobs? she thought, her consciousness a buoy bobbing on a chemical sea.

Kevin finally set his beer down with a definitive click. “Ash,” he started, his voice deliberately calm, “Mason is a dick, but are you seriously asking me for a… practical demonstration?”

Yes, you idiot, because I don’t want to be bad at it, she screamed inside, but all that came out was a strained, “I just need to know what to do. I can’t screw this up.”

Hope’s ear pressed harder against the cool wall, the dream receding as the cadence of their speech solidified into something terrifyingly real. That’s Kevin. And Ashlee. Talking about… A cold knot tightened in her stomach.

“This is insane,” Kevin muttered, running a hand through his hair as he glanced toward the closed bedroom door. Hope is dead to the world, there’s no way… but Jesus, Ashlee, this is a landmine.

“Please,” Ashlee whispered, the single word cracking with a vulnerability that made him flinch. She’s genuinely terrified, he realized, the absurdity suddenly overshadowed by a protective urge he didn’t ask for.

Hope’s breath hitched, her body rigid in the tangle of Kevin’s sheets. He didn’t say no. He didn’t say no. The drug’s embrace felt like a trap, pinning her in place to witness the collapse of her world.

“Okay, look,” Kevin sighed, leaning forward, his elbows on his knees. “For starters, it’s not a race. The enthusiasm matters more than some technical blueprint.”

He’s actually considering it, Hope thought, a silent scream building in her throat as she listened to her boyfriend outline the mechanics of infidelity. I’m right here.

Ashlee leaned in, her thick red hair a dark curtain against the TV’s light, her focus absolute. “Show me,” she breathed, the request no longer a question but a desperate plea.

Kevin’s heart hammered against his ribs, a frantic drumbeat of poor decisions. This is such a bad idea, he screamed internally, but the raw need on her face was a force he couldn’t deflect.

Hope’s fingers clenched the sheet, her knuckles white. Every word from the living room was a shard of glass etching itself into her memory. I am awake. I am here. And I hear you

That little bitch Ashlee with her thick red pillow lips and that curvy, firm ass, those perfect C-size tits she’s always so proud of—she’s trying to seduce my boyfriend right in our living room. She thinks I’m asleep, doped up on Ambien, dreaming through some twisted “blowjob lesson.” My blood is ice and fire, a static scream trapped in my chest.

“Just… use your hands, too,” Kevin’s voice is low, strained, a tutorial in betrayal. “It’s not just about the mouth.”

Ashlee shifts on the rug, her shadow stretching toward the bedroom door. “Like this?” Her whisper is a venomous curl in the dark.

My fingernails dig into my palms, the pain a sharp, clarifying anchor. Each of his words is a nail in the coffin of us.

He cleared his throat. “Yeah, like that. But softer. It’s not a… a job. It’s supposed to feel good.”

I can smell her shampoo from here, that cheap coconut scent, mingling with the stench of their secret. The floorboard in the hall creaks under the weight of their sin.

“Okay,” she breathes, a student eager to please. “Okay, I think I get it.”

I am not dreaming. This is real. The muted TV laughter is a mockery. My heart hammers a frantic, dangerous rhythm against my ribs. I will myself to move, to burst through that door and shatter their little world.

But my body is lead, frozen by the chemical haze and the sheer, gutting horror of it. He didn’t say no. He didn’t stop her.

The silence from the living room is louder than any sound.

Then, Ashlee’s voice, a low, urgent whisper, sliced through the dead air. “She’s fast asleep, Kev.” Hope’s blood went cold, every muscle locking. “She doesn’t need to know this.” The words were a venomous drip in the dark. “She won’t have a clue.”

Kevin’s reply was a ragged breath. “I don’t know.” His voice was thick with conflict. “This… changes things. Potentially between you, me, and Hope.” A floorboard groaned under his weight. “Isn’t she your best friend?”

Hope’s nails dug deeper, drawing blood she couldn’t feel.

“If she were thinking clearly,” Ashlee pressed, her tone slick and persuasive, “she would totally approve this, Kevin.” The rustle of fabric suggested she was moving closer to him. “It’s not a big deal.” A pause, loaded and heavy. “But we’ll still keep this a secret if you say yes.”

The silence that followed was a living thing, suffocating and dense. Hope could picture Ashlee’s predatory smile, Kevin’s tortured hesitation. Her own heartbeat was a frantic drum in her ears, drowning out everything but the echo of their betrayal. This was the point of no return.

This was the point of no return. Hope’s breath solidified in her lungs, a sharp, crystalline shard of pain. Every rustle from the living room felt like a physical violation.

Ashlee’s voice cut through the silence, a low, pleading whisper that grated against Hope’s nerves. “Can I at least look at it and you can explain things?” she urged, her words tumbling out in a rushed, desperate stream. “So I can get on my knees and you can kinda explain to me like where to suck and how to suck on it.”

Kevin’s internal monologue screamed a chaotic mix of panic and a twisted, reluctant curiosity. This is so messed up, but her fear is so real, so palpable it’s intoxicating. He let out a slow, controlled breath, the weight of the moment pressing down on him. “I guess I could do that,” he finally conceded, his voice hushed and tight. “No touching, Ashlee. Just theory.”

Ashlee’s heart hammered against her ribs, a frantic bird trapped in a cage of her own making. Thank god, now I might not be a complete failure when Mason gets back. She shifted on the worn rug, the coarse fibers scratching her knees through her sweatpants.

Hope’s fingers dug into the mattress, the fabric tearing under her nails. Theory? You bastard. You’re actually going to do this. The muted laughter from the TV felt like a mockery of her entire relationship.

Kevin ran a hand through his hair, his palm damp with sweat. “Okay, so… visually, it’s about the head, obviously.” His explanation was clinical, a feeble attempt to detach from the intimacy of the act he was describing.

Ashlee’s eyes were wide, unblinking, absorbing every word like a sacrament. She leaned forward, her red hair a dark curtain shielding her expression from the bedroom door, from Hope’s frozen, listening form.

The air in the room thickened, heavy with the scent of betrayal and stale pepperoni. Kevin’s gaze flickered toward the closed door, a spike of guilt piercing his chest. Hope is asleep, she’s safe, she doesn’t know, he lied to himself, the words a flimsy shield.

Hope’s tears were hot and silent, tracing paths through the makeup she hadn’t bothered to remove. She mapped the sounds, the cadence of their voices, branding this moment into her memory forever.

“The frenulum is… sensitive,” Kevin continued, his voice dropping even lower, each word a deliberate step into dangerous territory. Ashlee nodded, a quick, jerky motion, her mind already rehearsing.

Hope’s consciousness finally surrendered to the drug’s pull, the voices blurring into a distant hum as she fell back into a thick, dreamless sleep. Ashlee watched the bedroom door, her own heartbeat thundering in her ears now that the risk felt diminished. “Kevin,” she whispered, her voice husky with a mix of shame and desperate need, “can I just… put the tip in my mouth? For a second? Just to feel it.” His dick twitched against his sweatpants at her words, a traitorous response he couldn’t control. Fuck, this is so wrong, but the heat coiling in my gut is a live wire, his internal monologue screamed, the clinical theory evaporating under the weight of raw temptation. He let out a ragged breath, his resolve crumbling. “Just the tip,” he grunted, his voice strained. “For a moment.” Ashlee’s mind raced, yes, this is it, I need to know how it feels, her fingers trembling as she reached for his waistband. The fabric slid down, and the reality of him, thick and veined and already leaking, made her mouth water. She leaned forward, her red hair brushing his thigh, the scent of him—musky and male—filling her senses. Her lips parted, and she took just the swollen, purplish head into the wet heat of her mouth. Oh god, it’s so soft and hard at the same time, her tongue instinctively flicking against the slit, tasting the salty pre-cum. Kevin’s head fell back against the couch, a guttural groan escaping him as her hot, wet mouth enveloped him. Jesus Christ, her mouth is so fucking soft, the suction gentle but perfect, his hips bucking slightly against his will. She sucked, experimentally, her tongue circling the frenulum, and a violent shiver racked his entire body. I’m actually doing it, I’m not choking, it’s working, Ashlee thought, a surge of power mingling with her shame. He was so big, but she focused, her lips forming a tight seal as she applied more pressure. Kevin’s hand fisted in her hair, not pushing, just holding, his control fraying into shreds. “Ashlee,” he choked out, the word a warning and a plea. She moaned around him, the vibration shooting straight to his balls, and he knew this was far more than just a lesson.

The vibration of her moan was his undoing. His hips jerked forward, shoving his cock deeper into her wet, willing mouth. "Fuck, Ashlee," he grunted, his fingers tightening in her hair.

She pulled back, gasping, a string of saliva connecting her lips to his glistening tip. "Tell me what to do next," she panted, her eyes wild with a mix of triumph and need.

"Get lower," he commanded, his voice rough. "Suck my balls. Don't be gentle. Treat them like you would a shaft."

Ashlee didn't hesitate, her movements fueled by a desperate need to prove herself. She ducked her head, nuzzling beneath his heavy cock before taking one taut sphere into her mouth. She sucked hard, her tongue flattening against the sensitive skin, and Kevin saw stars, a raw, guttural sound tearing from his throat.

"Jesus, yes," he hissed, his body bowing off the couch.

Emboldened, she moved lower still, her hands spreading his cheeks apart. "And Tony's ass?" she whispered, the question a hot breath against his most forbidden place.

"Do it," he groaned, surrendering completely. Her tongue, slick and determined, pressed against his tight ring, licking and probing until he was shuddering, utterly possessed.

Her tongue, slick and determined, pressed against his tight ring, licking and probing until he was shuddering, utterly possessed. A distant, muffled sound pulled Hope from the depths of her drugged sleep. …take off your shirt. The voice was Kevin’s, but distorted, woven into a nightmare. Mommy play with a C cup titties for a minute. Her own mind was betraying her, stitching her insecurities into this awful dream. Now lay on the couch. The command was clear, followed by the sound of movement. I’m gonna get you a couple of pillows for your head. This wasn’t real. It couldn’t be. Gonna teach you how to take all my inches. The dream was so vivid, so cruel. You’re gonna gag. She felt a phantom pressure in her own throat. You’re gonna choke. Her breath hitched. Breathe your ass you’re gonna do great. The words dissolved into a static hum as the Ambien dragged her under once more, the truth buried beneath a chemical veil.

“Take off your shirt,” Kevin commanded, his voice husky and low, cutting through the thick air. Ashlee’s fingers trembled as she gripped the hem of her cotton tee, pulling it over her head and letting it fall to the floor. The cool air kissed her bare skin, her breasts feeling heavy and exposed. “Now lay on the couch, face up,” he instructed, his eyes dark with intent. She obeyed, sinking into the worn cushions, the fabric scratching her back. Kevin moved to the armchair, grabbing a couple of throw pillows, his muscles flexing under his t-shirt. He returned, placing them gently under her head, elevating her for better access. Her heart hammered against her ribs, a frantic drumbeat of anticipation and fear. Then he was above her, straddling her shoulders, his knees pressing into the couch on either side of her head. The weight of him was intimidating, his cock, thick and veined, hovering near her lips. He used his thumbs to gently part her jaws, opening her mouth wider. “Relax your throat,” he murmured, his tone a mix of instruction and desire. She felt the blunt, wet head of his dick press against her lips, then push past, into the warm, tight space of her mouth. He moved slowly, inexorably, the length of him sliding deeper, stretching her jaws and filling her throat. She gagged instinctively, tears pricking her eyes, but he held her head steady. “Breathe through your nose,” he grunted, his hips inching forward. The sensation was overwhelming, a full, suffocating pressure as he buried himself to the hilt, his balls resting against her chin. Every inch of him was inside her now, her throat convulsing around the intrusion. He let out a low, guttural moan, his body tensing above her. She could feel the pulse of him deep within her, a raw, claiming presence.

She could feel the pulse of him deep within her, a raw, claiming presence. Then he started to move, a slow, deliberate throttle that made her eyes roll back. His grip in her hair tightened, his hips setting a rhythm that was all his own. "Yeah, just like that, you perfect whore," he grunted, the words a hot, filthy prayer. The pace unwrapped, becoming something frantic and punishing. Her head snapped back and forth in a rapid, jerking motion, his hands using her skull for leverage, fucking her face with a brutal, selfish intensity. Spit slicked her chin and tears welled in her eyes, but the sounds he made were pure animal pleasure. "You're a natural, Ashlee, a goddamn great cocksucker." Each thrust hit the back of her throat, a suffocating, deep-stretch that made her gag and convulse around him. "This is our secret," he panted, his rhythm becoming erratic, jagged. "Hope can never know. We're always gonna be friends." The hypocrisy was as thick as the pre-cum on her tongue. She felt him swell, a throbbing, imminent pressure. "I'm gonna give you the biggest load," he groaned, his body tensing above her. "I want you to swallow every fucking drop." His release erupted, a hot, bitter flood hitting the back of her throat. She choked, then obeyed, swallowing convulsively as he emptied himself deep inside her.

The wet, gulping sounds from the living room were not a dream. Hope’s eyes were wide open, staring at the faint cracks in the bedroom ceiling she knew by heart. Kevin’s voice, raw and filthy, carved itself into her soul. You perfect whore. The mattress seemed to harden into stone beneath her. A goddamn great cocksucker. Each word was a puncture wound. She heard the frantic, rhythmic creak of the couch, the wet choke, his final, guttural groan as he unloaded into her throat. Her own throat closed tight, a searing line of pain where a scream should have been. She didn’t move. She didn’t breathe. The silence that followed was more violent than the noise. It was the silence of a bomb after the blast, the world holding its breath before the dust settles on the ruins. She stared at the ceiling, waiting for it to collapse. It didn’t. The only thing collapsing was her. A single, hot tear escaped, tracing a path through the numbness on her temple and into her hair. She did not wipe it away. She just lay there, dismantled, in the quiet dark of the bed she shared with him.

The taste of him, salty and bitter, was still a slick film in her mouth as she wiped her lips with the back of her hand. "Thanks, Kev," Ashlee whispered, her voice husky but steady, the earlier tremor of insecurity completely gone. "I actually feel... ready for him now."

"Shhh, for fuck's sake, be really quiet," he hissed, his eyes darting toward the bedroom door as he pulled up his sweatpants. He moved like a ghost across the creaky floorboards, easing the bedroom door open and slipping inside the dark room.

Hope felt the dip in the mattress, the shift of his weight, the faint, unfamiliar scent of her own shampoo on his skin. She kept her breathing slow and even, her body a statue of feigned sleep.

From the hallway, Ashlee’s voice, a low, confident murmur, slid through the crack in the door. "Good room. You have a great night."

Hope didn't stir, her eyes sealed shut against the treacherous dark, every muscle screaming as she listened to the sound of her world ending.

The sharp, acidic smell of coffee couldn’t cut through the thicker silence hanging over the kitchen table. Hope stared into her mug, the ceramic warm against her palms, her knuckles white. She’d been silent for most of the morning, the weight of the night a physical pressure behind her eyes.

“Rough night?” Kevin asked, his voice too casual. He nudged the sugar bowl toward her.

Hope’s smile was a tight, thin line. “Fine. I slept like a rock.” The lie tasted more bitter than the coffee. “What about you, Ash? You feeling better about things?” She forced her gaze up, meeting Ashlee’s eyes across the table. “Given that Mason had broken up with you.”

Ashlee froze, the spoon she was clinking against her mug going still. Her confident posture from the night before seemed to deflate. “He… what?”

“He broke up with you,” Hope repeated, her voice flat. “He texted the group chat last night. While you were… busy.” She let the implication hang, watching the color drain from Ashlee’s face. The satisfaction was a cold, sharp stone in her gut.

The satisfaction was a cold, sharp stone in her gut. Ashlee’s mouth opened, then closed, a fish gasping on the linoleum. “No, he didn’t,” she finally whispered, her voice cracking.

“Check your phone,” Hope said, her tone flat and dead. Kevin stared, his face a pale mask of dawning horror. Ashlee scrambled for her phone, her fingers fumbling against the screen.

The notification glowed, a bright, accusing rectangle in the dim kitchen. Her breath hitched. “Oh, god.”

Hope stood up, the legs of her chair screeching against the floor. “So you practiced for nothing.” She walked around the table, her movements deliberate and slow. “You sucked my boyfriend’s dick for a ghost.”

Ashlee flinched as if struck. “Hope, I—”

“Don’t.” Hope’s hand shot out, not to hit, but to grip the edge of the table, her knuckles white. “You don’t get to say my name.” The air crackled, thick with the stench of betrayal and stale coffee. Kevin finally found his voice. “Hope, let me explain—”

She turned her head, her eyes locking onto his. “Explain what? How you helped our friend?” She leaned in, her voice dropping to a venomous whisper. “Was she a good student, Kevin? Did she swallow your lesson plan?”

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