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Best Friends With Benefits

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Kevin has a wife of ten years named hope who is out of town working in San Fran for the week. Hope is 5 foot three small frame and has small natural tits. She is a terrible kisser but amazing at giving blowjobs and expert she also has a very high sex drive. Ashley Kevin best friend and weekend nanny for his platonic friend) Ashlee is Kevin's best friend. She is in her late 20s, curvy with perfect sea-size breasts, red hair, and a small gap between her top two teeth. She is insecure and quirky, working in a call center. Ashley sees Kevin as a brother, and father figure and he reciprocates that familial affection. Kevin is a successful investment banker in his early 30s. He is athletic, about 6 feet tall, with dark hair and blue eyes. He lives in a luxury apartment in Salt Lake City and enjoys the finer things in life. Despite his professional success, he finds his personal relationships complicated. Kevin and Ashlee are always joking with each other bringing whiskey and levity to any situation Ashley wakes up in Kevin’s bed after moving in. She passed out drunk the first night at his place, sleeping in Kevin’s king-size bed. Ashlee realizes she must have removed her T-shirt while she was sleeping. Kevin is sleeping naked on the other side of the bed. Internal monologue and thoughts with both characters, internal thighs and monologue, including what they see, think, and feel with visceral detail, including what they see, think, and feel. Kevin does not kiss or fuck Ashlee, but he does eventually end up straddling her face with his naked body, his nine-inch cock in front of Ashlee’s face. Ashlee laughs as Kevin slaps her face with his cock after winning the ticket contest, telling her to say uncle. Instead, Ashlee takes Kevin into her mouth. Kevin and Ashlee use extra whimsy during the blowjob, and Kevin also tells Ashlee that she is his best friend and he can’t believe he is inside of his best friend’s mouth . His best friend’s throat. The taboo of his best friend’s cock is electrification . Kevin reminds Ashlee that they will always be friends, that the blowjob changes nothing, as he pulls her head down. Ashlee is fully impaled a version of this that is gonzo dark as tons of humor whimsy silliness might be unbelievable, but somehow it’s all sticks together through several chapters during all chapters. We look into all characters, internal log, and thoughts, what they see thinking, and feel with visceral, explicit graphic detail.

Chapter 1: **The Whiskey Bet and the Morning After**

Ashlee woke to the smell of whiskey and expensive linen. Her mouth tasted like regret and stale Chardonnay. A dull throb pulsed behind her eyes, each beat syncing with the low hum of the city far below. Sunlight, sharp and accusatory, sliced through a gap in the blackout curtains, painting a brilliant line across the rumpled duvet and onto her bare thigh, which was stuck to the deep charcoal silk of Kevin’s sheets.

She didn’t need to open her eyes to know where she was. The pillow smelled like him—cedarwood soap, a faint hint of his cologne, the underlying scent of clean, warm skin. It was a smell that was both profoundly familiar and, in this hazy context, dangerously confusing. She remembered coming over, the bottle of single malt, laughing until her sides hurt on his absurdly large sofa. She remembered crying a little, too, about some guy at work. She did not remember deciding to sleep in his bed.

A floorboard creaked. Her eyes snapped open.

He was standing beside the bed, already dressed for his day in dark jeans and a simple grey t-shirt that strained slightly across his shoulders. His hair was damp from a shower. And he was… very close. Close enough that she could see the tiny scar through his eyebrow, the playful crinkle at the corner of his eye.

Close enough that her sleep-blurred vision focused, starkly, on what was positioned directly in front of her face.

He was completely, casually naked from the waist down. And he was… impressively, undeniably erect. The morning light glinted off the tip of him, which hovered, terrifying and mesmerizing, a mere breath from her parted lips. A stifled gasp caught in her dry throat. Her brain short-circuited, trying to process the sheer, audacious reality of it—the size, the proximity, the warm, musky scent of him mixing with the cedar and whiskey.

He looked down, a slow, wicked grin spreading across his face. It wasn’t a leer. It was the same grin he got when he was about to win an argument or pull off a ridiculously complicated cocktail. Pure, unadulterated Kevin confidence.

“Say uncle, Ash,” he said, his voice a low, morning-rough rumble.

Her heart hammered against her ribs, a frantic bird in a cage. Every neuron fired at once. This was Kevin. Her Kevin. The guy who’d held her hair back when she had food poisoning, who lectured her about her 401(k), whose fridge she raided without permission. He was her brother-from-another-mother, her fortress, her safe, platonic harbor in a chaotic world.

And he was currently presenting his fully erect, frankly magnificent penis to her like it was a trophy she’d won.

A hot flood of something—shock, yes, but beneath it, a treacherous, liquid warmth—spread through her belly. She stared, transfixed. The curve of him, the soft-looking skin pulled taut over unyielding hardness, the bead of moisture at the tip. It was so utterly alien, and yet, on him, it looked… logical. Like a piece of high-performance machinery, perfectly designed.

It’s just a body part, her mind screamed, trying to regain control. It’s just Kevin’s stupid, show-offy body part. But another, quieter, much more secret part of her whispered something else. It catalogued the sheer boldness of the act, the terrifying intimacy of it. It remembered all the times she’d accidentally-on-purpose brushed against his arm, the way her heart skipped when he laughed at one of her dumb jokes, the empty ache she felt in his apartment after Hope left. That part of her wasn’t looking at a brother.

“I… what?” she finally croaked, unable to tear her eyes away.

“You heard me,” he chuckled, shifting his weight slightly. The movement made him sway, and she flinched back against the pillows instinctively. A deeper, more visceral reaction clenched low in her abdomen. “You’re in my bed. My domain. My thousand-thread-count sheets. You forfeit your dignity when you passed out here. Now, say it.”

He was playing. He had to be playing. This was just an escalation of their usual ridiculousness, a boundary pushed into surreal, uncharted territory. But the air in the room had changed. It was charged, thick, crackling with a new and dangerous voltage. The simple, sibling-like trust they’d built over years felt thin and fragile as glass.

Just play along, she thought. Laugh it off. Call his bluff. But her throat was tight. Her lips tingled with a phantom sensation, the imagined heat of him. She couldn’t form the sassy retort. All she could do was stare, her cheeks burning, her body humming with an awareness of him she had spent years meticulously suppressing.

Kevin watched her, the grin still on his face, but his blue eyes were sharp, studying her reaction. He’d expected a shriek, a pillow thrown at his head, a shouted “You’re disgusting!” He’d expected the easy, scripted banter of their friendship. He hadn’t expected this stunned, wide-eyed silence. He hadn’t expected the flush creeping down her chest, disappearing beneath the oversized t-shirt of his she wore. He hadn’t anticipated the way her gaze didn’t dart away in disgust, but held, locked on him with a look he’d never seen from her before. It wasn’t sisterly. It was… something else.

A strange, unfamiliar tension coiled in his own stomach. This was Ashlee. Goofy, insecure, brilliant Ashlee, with her sea of red hair fanned out on his pillow and that tiny, endearing gap between her front teeth visible as her mouth hung slightly open. She was his best friend. His confidante. The one person whose presence didn’t require a performance.

So why had he done this? A juvenile power move? A test? The sight of her curled up in his bed, in his shirt, had sparked something primal and stupid in his sleep-addled brain. A need to provoke, to shatter the comfortable, safe dynamic, just to see what happened. Now, seeing the shock and the latent curiosity in her green eyes, he felt the game tilt on its axis. The control he always felt, in his deals, in his life, in this very apartment, slipped a notch.

The silence stretched, taut and humming. The confident leer he’d practiced in the mirror wavered. The nakedness he’d worn as a costume suddenly felt truly vulnerable.

Ashlee swallowed. The sound was loud in the quiet room. Her tongue darted out to wet her lips. She saw his eyes track the movement, his grin faltering for a split second.

Then, moving slowly, as if in a dream, she raised her hand from beneath the covers. She didn’t swat him away. She didn’t cover her face. Her fingers, trembling slightly, extended. They paused, a hair’s breadth from his heated skin.

Kevin stopped breathing.

Her fingertips, cool from the sheets, brushed against him—the lightest, most tentative touch. Just a whisper of contact. It was an electric jolt that went straight up his spine, shorting out every rational thought in his head. He hardened further under her touch, a completely involuntary response that made him suck in a sharp breath.

That single, soft touch shattered the last pretense of the joke. It was an question. An answer. A line irrevocably crossed.

Ashlee pulled her hand back as if burned, her eyes flying up to meet his. The confusion, the fear, the want was all right there, naked and undeniable. The playful challenge in his “say uncle” had vanished, replaced by a tense, breathless reality that hung between them in the sunlit, whiskey-scented air.

He opened his mouth to speak, to say something—anything—to glue the pieces of their old friendship back together. But no words came.

Before he could find them, Ashlee moved. In one fluid, desperate motion, she yanked the duvet up over her head, disappearing into a cocoon of dark silk.

“Go make coffee,” came her muffled, strained voice from within the folds. “We… we need to not be doing this.”

Kevin stood there, naked and utterly disarmed, staring at the shrouded form in his bed. The momentum of the morning, of his life, of everything, had just veered violently off its predictable, luxurious track. He turned, mechanically, and walked out of the room, the ghost of her feather-light touch still blazing on his skin.

He turned, mechanically, and walked out of the room, the ghost of her feather-light touch still blazing on his skin.

In the stark, minimalist kitchen, he moved on autopilot. The polished chrome of his espresso machine was cold under his palms. He filled the portafilter, tamped, locked it in. The gurgle and hiss were a familiar, grounding soundtrack. He was constructing normalcy, brick by brick, trying to rebuild the shattered wall between what just happened and what their friendship was supposed to be. He poured the dark, aromatic shot into a small ceramic cup. For her, he added a splash of steamed oat milk, just the way she liked it. His hands were steady. His mind was a riot.

What the fuck was that? he thought, the steam from the espresso curling up like a question mark. You shoved your dick in her face. Classy. Real fucking classy, Matthews. It was a joke. It was always a joke. But her touch… that wasn’t a punchline. That was an admission. And his body’s immediate, traitorous response to it? That was a confession.

He carried the two cups back down the hall, the silent apartment feeling like a held breath. He pushed the bedroom door open with his elbow.

She was sitting up, his t-shirt pooling around her hips, the duvet kicked down. She’d pulled her wild red hair into a messy knot. She looked young and eerily calm. Her eyes tracked him as he entered, green and unreadable.

“Espresso,” he said, his voice too loud in the quiet. “For the… you know. The head.”

She took the proffered cup, her fingers brushing his. A jolt. “The head?”

“The headache. From the whiskey.” He stayed standing, a safe few feet from the bed, sipping his own bitter shot. It did nothing to settle the chaos in his gut.

Ashlee took a slow sip, watching him over the rim. She lowered the cup, holding it in both hands in her lap. “We need to talk about the other head.”

Kevin choked, sputtering espresso. “Jesus, Ash.”

“What? It’s a valid topic. You presented it for discussion.” Her tone was light, almost their usual banter, but her gaze was unwavering, serious. “You started this. Don’t get shy now.”

“I started a stupid joke,” he said, running a hand through his hair. “It got out of hand. Let’s just… let’s just call it a weird morning and move on.”

“Move on,” she repeated flatly. She placed her cup on the nightstand with a definitive click. “Right. Because that’s what we do. We ignore the elephant. Or, in this case, the fully engorged, nine-inch elephant in the room.” She swung her legs over the side of the bed, planting her feet on the floor. The hem of his shirt rode up her thighs. “I touched you, Kevin.”

“I noticed.”

“I wanted to touch you.”

The silence that followed was absolute, broken only by the distant groan of the city. Kevin’s heart hammered against his ribs, a frantic, trapped thing. This was the cliff edge. He could back away now, make another joke, save them. He opened his mouth to do just that.

“For years,” she added, quietly.

The air left his lungs. All his clever deflections, his banker’s rationalizations, evaporated. Years.

“Ash… you’re my best friend.” It sounded weak, pathetic even to his own ears.

“I know exactly what I am to you,” she said, standing up. The shirt fell to mid-thigh. She took a step toward him. “The quirky sidekick. The sister you never had. The safe, non-threatening girl you bitch about your real girlfriends to.” Another step. The scent of her—sleep and sweet perfume—wrapped around him. “But Hope’s gone. And I’m here. And you put your cock an inch from my mouth. So, tell me, what exactly was the joke?”

He had no answer. There was none.

She closed the final distance. She had to look up at him. The gap between her teeth appeared as she set her jaw. “You’re scared.”

“Damn right I’m scared,” he burst out, a raw laugh escaping him. “This is a thermonuclear option, Ashlee! This is the thing that ruins everything. We don’t come back from this.”

“Who says we need to come back?” she whispered. Her hand came up, not to touch him, but to hover near the hem of his t-shirt. “Maybe we go somewhere else instead.”

His resolve was a sandcastle against a tidal wave. Every objection melted under the heat of her gaze. This is a catastrophic idea, screamed the part of his brain that managed risk for a living. This will destroy your most important asset. But the other part, the part that had just been alone in a kitchen screaming what the fuck, was tired of managing. It was tired of safe. It wanted the volatile, high-yield, utterly irresponsible investment standing right in front of him.

“Ash…” It was a groan, a surrender.

She took it as the permission it was. Her hands found the hem of his shirt and pushed it up. He raised his arms automatically, letting her pull it over his head and drop it to the floor. Her palms flattened against his chest, feeling the hard planes of his muscles, the frantic beat of his heart. She leaned in, pressing her lips to the center of his chest. A soft, warm kiss that burned through him.

“No,” he muttered, even as his hands came up to cup her shoulders.

“Yes,” she murmured against his skin, her mouth trailing lower, over his abdomen.

“This is insane,” he breathed, his head falling back.

“Probably,” she agreed, her fingers hooking into the waistband of his jeans. She popped the button. The zipper sounded obscenely loud.

He was still half-hard from the earlier encounter, but as she shoved his jeans and boxer briefs down his hips in one rough movement, the cool air and her hot gaze made him swell to full, throbbing rigidity again. He kicked the clothes aside, standing naked before her.

Ashlee didn’t hesitate. She didn’t gasp or swoon. She looked, with a focus that was almost clinical, her quirks submerged under a deep, singular hunger. “You’re perfect,” she stated, a simple fact.

Then she sank to her knees on the plush rug.

“Ashlee, wait,” he said, his voice strangled. His hands hovered above her head, wanting to push her away, wanting to pull her closer. “You don’t have to—”

“Shut up, Kevin,” she said, looking up at him. Her green eyes were dark, ferocious. “I’ve thought about this. For years. Let me have it.”

Her hand wrapped around the base of him, her fingers not quite meeting. Her touch was firm, purposeful. She didn’t tease. She leaned forward and took the swollen head into her mouth.

The heat was instantaneous, shocking. A sharp, sucking gasp ripped from his chest. Every nerve ending fired. Holy fuck.

Her mouth is so goddamn warm, he thought, the coherent part of his mind dissolving. And soft. And she’s… she’s really doing it.

Ashlee’s mind was a silent scream of triumph. Finally. Finally. The taste of him was musky, salty, uniquely Kevin. The weight of him on her tongue was a reality she’d only fantasized about. She hollowed her cheeks, applying pressure, and heard him curse above her.

She worked him slowly at first, learning the shape of him, the ridge of the head, the thick vein running along the underside. She used her hand in tandem with her mouth, twisting up from the base as she sucked down. Saliva slicked her movements. The sounds were lewd, wet, and they sent a corresponding pulse of aching need between her own legs.

“Fuck… Ash…” he groaned, his fingers tangling in her hair now, not guiding, just holding on. His hips gave a tiny, involuntary jerk.

She took it as a challenge. She pulled back, letting him pop from her lips with a slick sound. She looked up, her lips glistening. “You were saying? About ruining everything?”

He stared down at her, chest heaving, completely enslaved. “I was an idiot.”

A slow, wicked smile spread across her face. “Yeah,” she whispered. “You were.”

Then she dove back down, taking him deeper. She relaxed her throat, fighting the instinct to gag, pushing further until her nose pressed into the coarse hair at his base. She held there for a second, swallowing around him, feeling him twitch violently in her throat.

Kevin saw stars. White-hot pleasure shot up his spine, coiling tight in his balls. The visual was obliterating him—his best friend on her knees, his cock buried in that gorgeous, smart mouth, her red hair fisted in his hands. The taboo of it, the sheer wrongness, lit a fire in his gut. This wasn’t just sex. This was a boundary incinerated.

She began to move in earnest, a ruthless, steady rhythm. Up and down, her hand working what her mouth couldn’t take. She was messy, enthusiastic, hungry. She slurped and swallowed, using her tongue to lap at the sensitive spot just under the head with every upward stroke.

She’s going to make me come, he thought, panic and euphoria mixing. She’s going to swallow it. Oh, God.

“Ash… I’m close,” he warned, his voice ragged.

She redoubled her efforts, humming around him, the vibration driving him wild. Her free hand crept between her own thighs, rubbing frantic circles over the fabric of his t-shirt she still wore. She was getting off on this, on servicing him, on claiming him.

That was the final thread snapping. The sight of her pleasuring herself while she sucked his cock shattered any last pretense of control. His orgasm built, a tidal wave gathering force in his balls, a tight, screaming tension.

“I’m gonna—” he gasped.

She pulled off just before he erupted. A string of saliva connected her lips to his glistening tip. She stroked him fast, rough with her hand.

A strangled curse tore from his lips as his orgasm ripped through him. Thick, hot ropes of come shot out, splashing across her chin, her throat, the stretched collar of his t-shirt. He bucked into her fist, each pulse wracking his body, his muscles going taut as wire. She kept stroking him, milking him dry until he was spent, shuddering, dripping onto her fingers.

The room was silent except for their ragged breathing. The smell of sex and salt and sweat saturated the air, thick and heady. Ashlee looked up at him, her face a mess, his release glistening on her skin. She didn’t wipe it away. She held his gaze, her expression a complex mix of triumph, awe, and fear.

Kevin stared back, his mind blank, utterly emptied. The coiled tension that had defined his every moment since Hope left was just… gone. In its place was a hollow, shocked calm. He watched, detached, as a single drop slid from her chin onto her chest.

He reached down, his hands trembling slightly, and cupped her face. His thumbs, rough against her soft skin, smeared his own come across her cheeks. It was a possessive, filthy gesture. A brand.

“You’re fucking insane,” he breathed, but there was no heat in it. It was pure wonder.

“You started it,” she whispered, her voice hoarse.

He pulled her up by her shoulders, his strength returning in a rush. Before her knees left the rug, he kissed her. It was a raw, hungry clash of lips and teeth and tongue. He could taste himself on her—bitter, elemental. It should have repulsed him. It ignited him.

He walked her backward until her thighs hit the edge of the mattress. He broke the kiss, his hands going to the hem of the t-shirt. “This,” he growled, “is mine.” He pulled it up and over her head in one swift motion, tossing it aside.

She stood naked before him, bathed in the unforgiving morning light. Her body was lush, exactly as he’d imagined in his most secret, guilt-ridden thoughts: full breasts with pale, pink nipples already peaked and tight, a soft waist, the gentle curve of her hips. The red hair at the junction of her thighs was a surprise—a vivid, fiery match for the cascade on her head.

“You’re staring,” she said, a flicker of her old insecurity surfacing. She started to cross her arms over her chest.

“Don’t,” he commanded, his voice low. He caught her wrists, gently pulling them away. “Don’t you fucking hide from me. Not now.” He let his gaze travel over her, devouring every detail. “Christ, Ashlee. You’re beautiful.”

Tears welled in her eyes, but she didn’t look away. She let him look.

He pushed her down onto the bed. She fell back, her hair fanning out on the silk. He followed her down, covering her body with his, the heat of her a delicious shock against his skin. He took her mouth again, kissing her deeply as he settled between her thighs. The coarse hair there brushed against his still-sensitive cock, and he groaned into her mouth.

He kissed down her neck, licking away the traces of his own spend from her skin. He sucked a dark mark at the base of her throat, claiming her. His mouth moved lower, over the swell of her breast, until he took a nipple into his mouth, sucking hard, nipping with his teeth.

She cried out, her back arching off the bed. Her hands flew to his head, her fingers twisting in his dark hair, holding him there. “Kevin… please…”

He switched to the other breast, giving it the same torturous attention. His hand slid down her belly, through the damp curls, and found her already wet and open for him. He slid a finger inside her, and she was so tight, so hot, he nearly lost his mind.

“So fucking wet for me,” he muttered against her skin. “All these years… were you always this wet thinking about it?”

“Yes,” she gasped, shameless. “God, yes.”

He added a second finger, curling them, searching. When he found that spot inside her, rubbing it with a relentless pressure, her whole body jerked. She let out a sharp, broken sound. He fucked her with his fingers, setting a brutal rhythm, his mouth still on her breast.

“Come on my fingers,” he ordered, his voice rough. “Come for me, Ash. Show me.”

It wasn’t gentle. It wasn’t romantic.

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