Cover of The Confessions of Cabernet and Girlfriends

The Confessions of Cabernet and Girlfriends

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three friends sitting at a table Sheri, 60: Katie, 59 and Sally, 61. they are drinking red wine and the topic turns to sex. they alll admitted to having gay sex in college: Katie started telling her story then Sally and finally Sheri whose story was wild.

Chapter 4: Sheri growls into Katie's ear 'Take it all' as Sally bottoms out the plug, watching Katie's back arch violently before rolling her over to suck her engorged clit while Sheri mounts Sally from behind, both women screaming as they come simultaneously.

The black leather roll lay open on the rumpled silk like a surgeon’s kit. Sally’s fingers, precise and steady, selected the glass plug. It caught the lamplight, cold and smooth, its fluted shape designed for a specific, uncompromising purpose. The room seemed to hold its breath. Frank watched, his expression one of detached readiness. Sheri’s eyes were wide, hungry, fixed on the object in Sally’s hand.

Katie felt the focus shift onto her, a spotlight of pure intention. Her throat tightened. She had just taken a man’s cock down her throat with a daring she didn’t recognize. This was different. This felt… targeted.

“Your lead, you said,” Sally stated, her gaze lifting from the plug to Frank. “Can you follow instructions? Not initiative. Instructions.”

Frank gave a single nod. “Verbal or demonstrated. I follow.”

“Good.” Sally’s eyes slid to Katie. There was no malice in them, only a fierce, probing curiosity. “Katie. On your hands and knees. Face the headboard.”

The command, delivered in Sally’s best courtroom tenor, brooked no hesitation. Katie moved, her limbs feeling like someone else’s. The silk was slippery beneath her palms and knees. She faced the ornately carved mahogany, hearing the rustle of movement behind her. She felt utterly exposed, the cool air of the room kissing the dampness between her thighs, the sweat on her back.

“Sheri,” Sally said. “Hold her. Keep her open.”

Sheri moved with a soft, eager sound. She positioned herself at Katie’s side, her body warm and solid. One arm wrapped around Katie’s ribs, pulling her back against Sheri’s soft, pillowing breasts. Sheri’s other hand slid down over Katie’s stomach, possessive, then further back, palming the curve of her ass. “I’ve got you, honey,” Sheri murmured, her lips against Katie’s shoulder. Her fingers kneaded the flesh, then parted it. Katie gasped at the vulnerability, the direct invasion of cool air.

Sally picked up the bottle of lubricant. The snick of the cap opening was loud. She poured a generous amount onto her fingers, warming it. She didn’t touch Katie yet. She looked at Frank.

“You. Kneel behind her. Do not enter her. Not yet. I want you to watch. I want you to see exactly how it’s done.”

Frank complied silently, moving to kneel on the bed behind Katie’s presented form. His presence was a palpable heat, a silent audience of one.

Sally’s lubricated fingers found Katie then, not at her vagina, which was slick and swollen, but lower. The touch on her perineum, then the tight, forbidden pucker of her anus, made Katie jerk violently.

“Steady,” Sally said, her voice low and firm. Her fingertip circled the clenched muscle, applying gentle, insistent pressure. “This isn’t the stories, Katie. This is real. You need to breathe into it. You need to let it happen.”

Katie tried. She forced a shuddering breath, her forehead resting against her stacked fists. Sheri’s hold tightened, grounding her. Sally’s finger pressed, a slow, inexorable invasion. The burn was sharp, startling, a full-bodied protest. Katie cried out, a short, sharp sound.

“Breathe deep, counselor,” Sheri whispered, parroting Sally’s earlier words with a throaty chuckle. “This is gonna hurt so good.”

The tip of Sally’s finger slid past the resisting ring of muscle. The intrusion was shocking, a fullness in a place that had never been touched, not even by her own hand. Katie whimpered, her body trembling. Sally worked her finger slowly in and out, the drag of lubrication and tight muscle a filthy, precise sound.

“She’s tight,” Sally observed clinically, her eyes on her work. “Virginal.”

“Fuck,” Frank breathed from behind them, the first hint of genuine awe in his voice.

Sally added a second finger alongside the first. The stretch was immense, a tearing, burning sensation that made Katie see white spots behind her eyelids. Tears welled in her eyes. It was pain, but it was pain with a purpose, pain being administered by her oldest friend, pain that was somehow unlocking a terrifying, dark pleasure deep in her belly. She bore down, trying to accommodate it, and a gush of wetness spilled from her vagina onto the sheets below.

“There she is,” Sally cooed, her legalist’s facade cracking to reveal a woman fascinated by her own power to elicit such a response. She scissored her fingers gently, stretching Katie open. “See how she’s dripping? Her pussy is loving this. It’s all connected, Katie. Every nerve.”

Sally withdrew her fingers. The empty, stretched feeling was its own strange ache. Katie heard the click of glass against glass, the sound of the plug being generously coated. She braced herself.

The cold, slick bulb of the plug pressed against her. It was so much broader than two fingers. She tensed, a low animal noise of panic escaping her.

“No,” Sally commanded. “You wanted new. This is new. Now take it.”

Sheri’s hand left Katie’s ass and clamped over her mouth, muffling her next cry. “Shhh, take it, baby. Just let it in.”

Sally pushed. The pressure was immense, impossible. Katie felt herself being stretched wider than she thought possible, the cold, hard glass an alien presence forcing its way into her most private depth. The burn was searing, a bright line of pain that felt like it would split her in two. She shook her head wildly against Sheri’s hand, her screams trapped.

Then, with a final, wet pop, the widest part of the bulb slipped past the clenching muscle. It was in. The narrow stem settled at the entrance, the flared base resting against her, a cold, unyielding anchor.

For a moment, there was only Katie’s ragged, sobbing breaths through her nose. The fullness was profound, a constant, pressing intrusion that shifted her entire sense of internal space. The initial sharp pain began to fade into a deep, throbbing ache, a heat that spread through her pelvis.

Sheri removed her hand from Katie’s mouth. “Look at that,” she breathed, her own voice shaky with arousal. “So pretty. So full.”

Sally sat back on her heels, wiping her hands on a corner of the sheet. She was flushed, her bun coming undone, dark strands clinging to her damp neck. She looked at her handiwork with a painter’s critical eye, then at Frank. “Now,” she said, her voice regaining its steel. “You may enter her pussy. Slowly. I want you to feel how this,” she gestured to the plug, “makes her even tighter for you. I want you to fuck her with it in. And I want you to tell her what it feels like.”

Frank didn’t need telling twice. The condom was on in seconds. He moved forward, his hands gripping Katie’s hips. The broad head of his cock found her soaked, swollen opening. He pressed forward, and Katie cried out again, this time from the overwhelming double sensation. The hard glass inside her pressed forward against his invasion, creating an almost unbearable tightness. He was stretching her front while the plug filled her back, sandwiching a thin, exquisitely sensitive wall of tissue between them.

“Jesus Christ,” Frank groaned, sinking deeper inch by torturous inch. “She’s… god, she’s gripping me like a vise. I can feel the other side. I can feel the fucking glass.”

His words, raw and descriptive, pushed Katie over an edge she didn’t know was there. The degrading clinicality of it, the sheer mechanical fullness, triggered a brutal, sudden orgasm. It ripped through her with no warmth, just a series of sharp, convulsive clenches that milked Frank’s cock and squeezed the implanted glass. She screamed, her body bowing between Sheri’s hold and Frank’s thrust.

Frank began to move, a shallow, grinding rhythm dictated by the intense pressure. Each withdrawal made the plug feel more prominent; each thrust drove it harder against his shaft. “Tightest fucking hole I’ve ever been in,” he grunted, his control fraying. “You’re packed, you feel that? You’re absolutely packed with cock and glass.”

Sally watched, her hand now between her own legs, her fingers working in a frantic, messy rhythm against her clit. She was no longer the director, but a participant, unmoored by the scene she had orchestrated. “Does it hurt?” she demanded of Katie, her voice breaking.

“Yes!” Katie sobbed, the word torn from her. “God, yes, it hurts, it’s too much!”

“Do you want him to stop?”

“No! No, don’t stop!” The plea was desperate, sincere. The pain had transcended itself, becoming a pure, blinding channel of sensation. She was a vessel, being used precisely as designed.

Sheri, overcome, released Katie’s torso and slid down behind Frank. She pressed her mouth to the small of his back, licking the sweat, then lower, her tongue finding his balls, then tracing the place where his cock plunged into Katie, where the base of the plug sat flush against skin. The wet, slapping sounds of fucking mixed with her greedy, slurping kisses.

Frank’s pace became erratic, brutal. He was chasing it now, his professional detachment incinerated in the furnace of this configured pleasure. “Gonna come,” he warned, his voice a ragged scrape. “Gonna fill this condom up inside this stuffed little cunt.”

His final thrusts were savage, pounding Katie forward into Sheri, who clutched at her. With a roar that seemed to shake the bed frame, he emptied himself, his body locked in a rigid spasm against her.

In the shuddering quiet that followed, Frank pulled out, collapsing to the side. The sudden absence of his cock made the plug’s presence even more pronounced, a cold, hard fact lodged inside her. Katie slumped forward, spent, tears cutting clean tracks through the sweat on her cheeks.

Sally was still touching herself, her climax elusive, a frantic energy with no release. Her eyes were wild, unsatisfied. She looked at the plug, at Katie’s wrecked form, at Frank recovering beside her. The experiment was a success, but it hadn’t given her what she needed.

Sheri crawled up the bed, her face glowing with vicarious pleasure. She gently pushed Katie onto her side and curled around her, spooning her, one hand stroking her hair. “You were amazing,” she whispered. “A fucking champion.”

Katie could only shudder, lost in the aftermath.

Sally stared at her own trembling fingers. Then she looked at Frank. His eyes were open, watching the ceiling, his breath slowly evening.

“The two hours,” Sally said, the words hollow. “They’re not up.”

Frank turned his head. He saw the unresolved frenzy in her, the void the plug and the orchestration couldn’t fill. He sat up. He reached for the black roll, his movements slow, deliberate. He picked up the second condom. He looked at Sally, not as a client, but as a puzzle.

“Your instructions are complete,” he said. “My initiative is now… permitted?”

Sally held his gaze, her chest rising and falling rapidly. After a long moment, she gave one sharp, almost imperceptible nod.

Frank moved. He didn’t go for her. He went to Katie. Gently, he turned her onto her stomach. Sheri made a small sound of protest but slid away, watching. Frank positioned himself behind Katie. His large hands smoothed over her ass, his thumbs finding the flared base of the glass plug.

“Sally,” he said, without looking away from his work. “Watch this.”

He began to slowly, slowly rotate the plug. The gentle twist sent a shockwave of sensation through Katie’s over-sensitized nerves. She moaned into the pillow. Then, with agonizing slowness, he started to pull it out.

The drag was immense, a reverse invasion that made Katie cry out. The glass, now warmed by her body, slid free with a soft, wet pop. The emptiness it left was shocking, a cool, open ache.

Frank held the glistening plug up, turning so Sally could see it fully. Then, his eyes locked on hers, he brought it to his mouth. He ran his tongue along its length, cleaning it of lube and her essence, his gaze never leaving Sally’s face. The obscenity of the act, the total reclamation of her tool, was absolute.

He tossed the plug onto the sheets. It landed between them with a soft thud.

“Now,” he said to Sally, his voice a dark promise. “Your turn. And I’m not following any more instructions.”

And I’m not following any more instructions.”

The silence after his declaration was brittle. Sally’s breath caught, a sharp intake that sounded almost like fear. It was the fear she’d described on the boat—the terrifying thrill of the script burning away. Frank moved. He didn’t approach her. He turned back to Katie, who lay shuddering on her stomach, the ghost of the plug still a palpable absence inside her.

“Roll over,” he told Katie, his voice leaving no room for refusal. She obeyed, her movements slow with exhaustion, her eyes glazed. He guided her onto her back, her legs falling open. He looked at Sheri. “Hold them. Keep her wide.”

Sheri, wordless, crawled to the head of the bed. She lifted Katie’s shoulders, pulling her into a half-seated position against her chest, then reached down and took Katie’s wrists, gently drawing her arms back and apart. It was a pose of vulnerable display. Katie’s head lolled on Sheri’s shoulder, her gaze drifting to Sally.

Frank retrieved the discarded glass plug from the sheets. It was still slick. He held it up, not to Sally, but to the light, as if inspecting it. Then his eyes, flat and intent, found Sally’s. “You like to watch. You like to direct. Now you’re going to participate.” He nodded toward Katie’s exposed body. “You’re going to put it back in.”

Sally’s throat worked. “I… no. That was for her. The experiment—”

“Is over,” Frank interrupted, his tone final. “This isn’t an experiment. This is you, putting this inside your friend, because I’m telling you to. Because part of you is screaming to do it.” He took a step toward the bed, the plug held loosely in his fingers. “You wanted to see how deep it could go. So find out.”

A tremor ran through Sally’s fine-boned hands. She looked from Frank’s implacable face to Katie’s yielding form, to Sheri’s eager, encouraging eyes. The part of her that drafted airtight contracts was gone. What remained was raw want, a yawning need for the degradation she’d so carefully assigned to others. She reached out, her fingers closing around the cool, hard glass.

Her movements were stiff as she moved to kneel between Katie’s splayed legs. Katie whimpered, a faint sound of protest mixed with startling anticipation. “Sally…?” she breathed.

“It’s okay,” Sally heard herself say, the lie automatic. Her thumb stroked the fluted base. She poured more lube, the bottle clicking in her unsteady grip, coating the plug until it gleamed. Sheri’s hold on Katie tightened, a silent reinforcement.

Sally positioned the bulb. Her hand was shaking. She pressed. Katie’s body resisted, the muscle clenched tight from the recent trauma. Sally pushed harder, her other hand bracing on Katie’s thigh. It was a brutal, clumsy re-entry, devoid of the clinical precision from before. This was force.

Katie cried out, her back arching off Sheri’s chest. “Fuck! Sally, stop—”

“Don’t stop,” Frank commanded, looming over them, a monument of demand. “Push it. All the way. Seat it.”

Sally’s jaw tightened. She leaned her weight into it, a low grunt escaping her as she bullied the glass past the tight ring of muscle. It slid in with a sick, wet sound. Katie sobbed, her body accepting the violation. Sally pushed until the flared base was snug against her, the stem buried deep within. Deeper than before. The plug was fully seated, a cold, hard truth inside her friend.

Sally stared at her own handiwork, her fingers still touching the base. A wave of nauseous power washed over her. She had done this. She looked up at Katie’s tear-streaked face and felt something crack open in her own chest.

“Now,” Frank murmured, his voice close to Sally’s ear. He had moved behind her. His hands, large and hot, settled on her hips. “You get yours.”

He didn’t guide her to the bed. He kept her kneeling. He freed himself, already hard again, and sheathed himself swiftly. His thumbs dug into the dimples of her lower back. “Arch your back,” he said, his tone leaving no space for thought. “Present yourself. You wanted complexity. This is simple.”

Sally obeyed, the command short-circuiting her mind. She arched her spine, pushing her ass back toward him, her face still turned toward Katie and the implanted plug. It was the most exposing posture of her life. Frank spat into his palm, slicked himself, and without ceremony, drove into her ass.

The penetration was instant and absolute. No preparation, no gentle stretching. Just a brutal, tearing entry that stole the air from her lungs in a silent scream. The pain was an white-hot spike, a cleaving. She collapsed forward onto her elbows, her forehead pressing into the mattress beside Katie’s hip. A strangled, animal noise was wrenched from her throat.

“Yeah,” Frank grunted, beginning a ruthless, shallow rhythm. “That’s it. That’s the sound. The smart one, reduced to this.” Each thrust was a jarring impact, driving the air from her lungs. The pain began to mutate, blending with a shocking, electrical feedback of pleasure as he hammered against her prostate. Sparks exploded behind her clenched eyelids.

Katie, through her own haze, watched Sally’s face contort. She saw the utter dismantling of her friend’s composure. Reaching out a trembling hand, she touched Sally’s cheek. “Sally,” she whispered.

Sally’s eyes snapped open, wild and unseeing. Then they focused on Katie. On the faint outline of the plug buried inside her. The connection—her pain in her ass, the object she’d buried in her friend—smashed the last of her restraint. “I’m sorry,” Sally gasped, the words ragged between Frank’s pounding thrusts. “I’m so sorry, I’m—”

Her apology dissolved into a guttural cry as Frank changed angle, sinking deeper. “You like it,” he snarled, his hands biting into her flesh. “Your tight little lawyer ass is fucking milking me. You put a plug in her and now you’re getting fucked in the ass. You planned this.”

“I didn’t—” she tried to argue, but her body betrayed her, pushing back against him, meeting his thrusts. The pleasure was filthy, undeniable, coiling low in her gut.

“You did.” He leaned over her, his chest damp against her back, his mouth at her ear. “This was always the last story. The one you wouldn’t tell.” He fucked her harder, faster, the slapping sounds obscene. “Come for me. Come on the cock in your ass while you look at what you did to her.”

The command, the imagery, the searing fullness broke her. Sally’s orgasm erupted without warning, a convulsive, violent seizure that locked her muscles and tore a shredded scream from her throat. It was pain and pleasure fused into a single annihilating fire. Frank roared, pulsing deep inside her as she clenched around him, her vision tunneling to the sight of Katie’s exhausted, placid eyes.

He withdrew slowly. Sally collapsed, a boneless heap on the soaked sheets, feeling the hot, aching emptiness he left behind. Frank disposed of the condom. The room was silent except for their tortured breathing.

Dawn was a gray stain seeping around the curtains. The candle had drowned in its own wax. Frank stood, dressed with the same efficient quiet with which he’d arrived. He looked at the three women tangled on the bed—Sheri holding Katie, Sally broken beside them, the plug still evident.

He said nothing. He simply left. The soft click of the front door was the period on the night.

Minutes passed. The gray light grew. Katie finally stirred, a wince crossing her face. “Sally,” she whispered, her voice rough. “It’s… it’s still in. You have to take it out.”

Sally forced herself to move. Her body screamed in protest. She knelt again, her fingers, now tender, finding the glass base. She met Katie’s gaze. There was no judgment there, only a shared, shattered understanding. Sally pulled, gently this time. The plug slid free with a soft release.

The relief on Katie’s face was profound. Sheri exhaled, her arms loosening. They lay there in the grim morning light, naked, used, and irrevocably changed. The stories they had told over wine were fairy tales. This, the silence thick with the smell of sex and sweat and their own collective fear, was the only truth that mattered now.

Sally finally spoke, her voice a hollowed-out shell. “What have we done?”

Nobody had an answer. The momentum of the night was gone, leaving only the heavy inertia of consequence in its wake.

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