Chapter 6: The Ultimate Stretch
The air still stank of sex and sweat and Maggie’s own release, thick and cloying despite the vanilla candles Ben had relit. Maggie lay sprawled on the ruined silk sheets, utterly spent. Her body felt like it had been dismantled and loosely reassembled. Her cunt throbbed with a deep, bruised ache. Her asshole pulsed, a raw, open ring of fire still stretched wide from the thick plug Ben had slowly withdrawn minutes ago. The DP training kit plugs lay discarded, glistening obscenely on the nightstand beside the harness. Her clit, swollen to a fat, angry red nub, felt hypersensitive even to the cool air drifting over it. She shivered, a tremor running through her limbs, her eyelids fluttering as she fought to stay present. The low thrum of the computer fan was the only constant sound besides her ragged breathing.
Ben, however, was already moving. Efficient, focused. He rummaged in the large, black case he’d brought. "Chat's restless, Mags," he said, his voice calm, devoid of the dark intensity it held during her destruction moments before. He pulled out an object wrapped in thick plastic. "They saw you take the big one. They want… more perspective." He tore the plastic away.
Maggie forced her eyes open, focusing with effort. What he held made her breath catch, a fresh wave of exhaustion and apprehension washing over her. It was the XL Bad Dragon plug. Its asymmetrical shape was monstrous, covered in thick, pronounced ridges and bumps that looked more like geological formations than sex toys. The sheer girth near its middle dwarfed even the thickest plug from the DP kit. It glistened under the lamplight, coated in a fresh layer of slick, clear lube Ben had just squeezed onto it.
"Ben…" Her voice was a cracked whisper. "That thing… it’s a fucking monster."
"It is," he agreed, holding it up casually. He turned it slowly, letting the camera mounted on the tripod capture every intimidating ridge, every brutal contour. "Check the scale, chat." He walked closer to the bed, the monstrous toy held aloft. "Hold still, superstar." Without ceremony, he pressed the cold, lube-slicked tip firmly against her still-gaping asshole.
Maggie hissed, her body tensing instinctively. The tip alone felt huge against her tender, overstretched ring. It wasn't entering; it was just pressed there, a chilling promise of violation. Ben held it in place, letting the camera zoom in. On the monitor, the image was stark: her fiery red pubic hair slicked flat, her swollen, dripping cunt still visibly puffy, her huge clit jutting aggressively, and her asshole – stretched wide enough to admit fingers easily – dwarfed by the obscene, ridged head of the Bad Dragon plug pressed firmly against it. The sheer size difference was shocking.
"Look at that fucking gape," Ben narrated, his tone almost clinical. "Still hungry, isn't it, Maggie? But look at this beast." He wiggled the plug slightly, making her flinch. The chat exploded. Emojis of fire, shock, and dollar signs flooded the screen. Names started popping up: ‘The Canyon Maker!’ ‘The Gape God!’ ‘Mount Fuckmore!’
‘FUCK HER WITH IT!’ ‘SHOVE THAT MONSTER IN!’ ‘HER HOLE WILL SPLIT!’
Maggie whimpered, her eyes fixed on the monstrous toy. "Oh fuck, no… Ben, please… not that… not now…" She was genuinely terrified. Her ass felt raw, the memory of the brutal DP stretching still a fresh agony.
Ben held the Bad Dragon plug against her for another agonizing second, letting the image sink in for the chat, letting Maggie's fear radiate through the screen. Then, with a swift, decisive motion, he pulled it away. Maggie sagged in relief, a shaky breath escaping her.
But Ben wasn't done. He dropped the XL plug onto the bed beside her thigh with a soft thud. It lay there, a gleaming, terrifying presence. He turned back to the open kit, pulling out two much smaller plugs – smooth, tapered silicone, each about the girth of two fingers. They looked almost laughably tame next to the Bad Dragon, yet still substantial enough to promise significant stretch, especially together. He coated them liberally with lube, the slick sound loud in the sudden quiet.
Maggie watched him, confusion warring with dread. "Ben? What…?"
He didn't answer immediately. Instead, he positioned himself between her splayed legs again. He held up the two smaller plugs for the camera. "Chat wants double penetration," he said simply. "Maggie’s greedy asshole just got a taste of the big leagues. Let’s see how well it handles… guests." He pressed the slick tips of both smaller plugs together, aiming them squarely at her gaping, tender asshole.
Realization dawned on Maggie, sharp and terrifying. "No! Ben! Not both… in there?!" Her voice rose in panic. Her asshole clenched weakly, instinctively recoiling from the dual pressure.
"Shhh," Ben murmured, his voice low but firm. "Relax. Open up." He applied steady pressure. The two tips, pressed side-by-side, felt wider than she expected against her loose ring. It wasn't the single, brutal girth of the XL plug, but the separateness of the invaders was deeply unsettling. "Push out. Yeah… let them in."
Maggie squeezed her eyes shut, tears pricking again. She forced herself to relax, pushing out as he’d taught her. The resistance gave way with a soft, wet pop. The dual tips breached her simultaneously. She gasped, a sharp intake of breath. The stretch was immediate and intense – not the agonizing tear of the XL, but a unique, spreading pressure as her asshole stretched laterally to accommodate both invaders at once.
"Fuuuuck," she moaned, her fingers twisting in the sheets. Ben pushed slowly, steadily. Maggie felt every ridge of each plug slide past her ring, distinct sensations in her sensitive passage. One seemed smoother, the other had subtle, teasing bumps. Her asshole stretched wide, engulfing the dual shafts. The feeling of being split open by two separate objects, each moving independently yet together, was profoundly violating and bizarrely erotic. The deep ache from earlier flared, mingling with the fresh stretch.
"Look at that," Ben breathed, his gaze fixed on her asshole as it stretched obscenely wide around the dual plugs. He pushed them deeper, inch by careful inch. The camera zoomed in, capturing the impossible sight: her dark, puffy rose forced wide around two distinct, glistening shafts of silicone. The stretched skin looked tight, shiny. "Chat, say hello to Maggie’s new front door." He gave the plugs a slight twist.
Maggie cried out, her hips lifting off the bed. The sensation of the plugs twisting inside her, turning against each other, sent sparks through her raw nerves. Her huge clit gave a painful throb, untouched yet responding to the deep, invasive pressure.
The chat lost its collective mind. ‘DOUBLE TROUBLE TUNNEL!’ ‘TWO IN THE PINK!’ ‘ASS GOBLINS!’ ‘WIDE LOAD EXPRESS!’ The crude nicknames scrolled by, fueling Ben, exciting the viewers. Tips chimed in rapid succession.
Ben began a slow rhythm. Not deep thrusts yet, but gentle rocking motions, sliding the plugs partially out before pushing them back in together. The dual penetration created a unique friction, the plugs sliding against each other inside her as well as against her tender inner walls. Her asshole visibly fluttered and clenched around the shafts with each withdrawal and re-entry, the gaping hole struggling to close only to be forced wide open again.
"Ben… oh god… it feels… so weird…" Maggie panted. Her voice was thick with overwhelmed sensation. The plugs were hitting spots deep inside, triggering unfamiliar pulses of heat. Her body, wired for pleasure even through exhaustion and pain, was responding. Her cunt, ignored for now, began to weep fresh arousal, mingling with the lube and sweat on her thighs.
"Feel them rubbing?" Ben asked, his voice dropping to a husky murmur. He increased the pressure, pushing deeper. "Two cocks in your ass, Maggie. Filling you up." He gave a firmer thrust, seating both plugs fully. The bases pressed firmly against her stretched opening. Maggie whimpered, feeling impossibly full, split wide in a way she never had before. The plugs felt huge inside her narrow passage, their combined presence dominating her completely.
He started a proper, slow fuck. In and out. Together. The wet, squelching sounds were loud, obscene. Her gaping hole stretched wide with each outward pull, the inner pink flesh glistening under the lights, then swallowed the plugs again with a wet gasp. The camera lingered, zooming, capturing every twitch, every pulse of her strained sphincter. Ben watched the monitor, a satisfied smirk on his face. "Look at them go, chat. Maggie’s asshole putting on a show."
The nicknames kept coming, more graphic, more degrading. ‘MEAT GRINDER!’ ‘SLOP HOLE!’ ‘DOUBLE FISTED FUCK CHUTE!’ Each one sent a fresh wave of humiliation and unwanted arousal through Maggie. Her breath hitched. The plugs ground deep, shifting independently with Ben’s movements, creating a chaotic friction that scraped deliciously against her raw nerves. The pain was still there, a constant throb, but it was becoming entwined with a rising, molten heat low in her belly. Her clit felt swollen to bursting, screaming for attention. The relentless double penetration in her ass, the crude commentary from the chat, the sheer degradation of being stretched so obscenely open… it was pushing her towards an edge she hadn't expected.
"Ben…" she moaned, her voice cracking. "I… I can't… it's…" She didn't know what it was. Too much? Not enough? Her hips began to rock minutely, meeting his slow thrusts. Her asshole fluttered wildly around the invading shafts. The plugs twisted again as Ben changed the angle, pressing hard against a bundle of nerves deep inside.
"Oh fuck!" Maggie shrieked, her back arching violently. "Fuckfuckfuck!" The heat detonated. Not from her clit, but deep in her core, radiating out from where the two plugs ground together inside her violated ass. It was an anal orgasm, brutal and unexpected, ripped from her by the relentless double penetration and overwhelming degradation. Her asshole clenched and spasmed violently around the plugs, a series of rapid, uncontrollable pulses trying to milk the unyielding silicone. Fluid gushed from her neglected cunt, soaking the sheets anew. She convulsed, eyes rolling back in her head, her mouth slack, drool trickling down her chin as guttural, animalistic sounds erupted from her throat. She came apart, utterly possessed by the sensation of being double-fucked in the ass on camera for thousands of strangers.
Ben held the plugs deep, letting her ride the violent waves, her gaping asshole twitching obscenely around them on screen. He leaned down, his lips brushing the shell of her ear as she shuddered and gasped. "That's my good little anal whore," he whispered, darkly possessive. "Look how greedy that asshole is. Swallowing two like it's nothing." He gave the plugs a final, grinding twist as her tremors began to subside. Maggie whimpered, a broken sound. On the monitor, the chat demanded he leave them in, make her walk, show the gape. Ben just smiled, his hand resting on the base of the plugs still buried deep in Maggie’s ruined ass. Her journey into the extreme had just found a new, deeper level.
Her journey into the extreme had just found a new, deeper level. Ben’s hand remained possessively on the twin bases protruding from her asshole. Maggie trembled, aftershocks still rippling through her core, her cunt dripping onto the soaked silk beneath her. The plugs felt heavy, alien, stretching her impossibly wide even at rest. Ben leaned close again, his breath hot on her neck. "Still with me, superstar?" His voice was low, almost conversational, yet laced with dark intent. Maggie managed a weak nod, her eyes fluttering open to see the chat still scrolling furiously on the monitor. ‘LEAVE THEM IN!’ ‘MAKE HER WALK!’ ‘SHOW US THE GAPE!’ ‘FIST HER CUNT NOW!’
Ben chuckled softly, a dry sound. "Patience, chat. Patience." His fingers trailed down her inner thigh, slick with her own juices and lube. They bypassed her weeping slit entirely, heading straight for the engorged, throbbing bud of her clit. Maggie gasped as his thumbpad made contact. Even that light touch sent electric jolts through her oversensitized nerves. He didn’t stroke yet. Instead, his other hand moved to the small remote control clipped to his belt. Maggie’s eyes widened, a fresh wave of apprehension tightening her chest. She knew what was coming.
He pressed a button. A low, powerful hum vibrated through the plugs buried deep inside her ass. Maggie cried out, her body jerking violently. "FUCK! BEN!" The vibration wasn't gentle. It was intense, buzzing directly against her raw, stretched inner walls, mimicking the frantic pulse of her recent orgasm but amplifying it brutally. The plugs seemed to come alive, vibrating against each other inside her passage, creating a chaotic, grinding friction that scraped every nerve ending raw. Her asshole clenched and fluttered wildly around the vibrating invaders, the stretched ring visibly pulsing under the camera’s relentless gaze. The sensation was overwhelming, a confusing mix of deep, internal agony and perverse, unwanted stimulation that radiated outwards, making her neglected cunt clench emptily.
Ben ignored her cries. His thumb began to move on her clit. Not gently. He pressed down hard on the swollen, hyper-sensitive nub, the pad of his thumb grinding against it in rough, deliberate circles. He used her own slick arousal coating his thumb as lubricant, but the pressure was brutal. "Look at this fucking clit," he growled, his voice carrying clearly to the mic. He pinched the engorged flesh between thumb and forefinger, pulling it taut, stretching it away from her body. The vibration in her ass intensified, syncing with the rough manipulation. Maggie screamed, her back arching off the bed, her vision blurring. Pain and pleasure collided violently inside her skull. Her hips bucked wildly, trying to escape the dual assault, but Ben held her clit firmly, stretching and grinding it relentlessly. Tears streamed down her face, mixing with the drool on her chin.
"Read it," Ben commanded, nodding towards the monitor. His thumb kept its brutal pace on her clit. Maggie forced her swimming vision to focus on the scrolling text. The words swam before her eyes: ‘STRETCH THAT MEATY CLIT!’ ‘FUCK HER RAW!’ ‘MAKE HER BEG FOR A FIST!’ ‘GAPE QUEEN!’ ‘SHOW US THAT HOLE WALK!’ The crude nicknames – ‘Meat Grinder’, ‘Double Fisted Fuck Chute’ – burned into her brain, fueling the humiliation that twisted alongside the agonizing pleasure radiating from her clit and vibrating ass. Each degrading comment felt like a physical blow, tightening the coil of sensation deep in her gut. She whimpered, the sound ragged and broken. "They… they want… the walk… Ben…"
"They do," Ben confirmed, his voice flat. He released her clit abruptly. The sudden absence of pressure was almost as shocking as the assault itself. The plugs still vibrated relentlessly inside her. He grabbed her hips, rolling her roughly onto her side, then pulling her up to a sitting position on the edge of the bed. Maggie swayed, dizzy, the plugs shifting heavily inside her, the vibration making her thighs tremble. Standing felt impossible. Her legs were jelly. Ben gripped her upper arm firmly, hauling her upright. "Move," he ordered, his tone brooking no argument. He steered her towards the center of the room, away from the bed, directly into the harsh pool of light cast by the main camera. The secondary camera swiveled smoothly to track her.
Every step was agony. The vibrating plugs shifted and ground deep inside her ass with each movement, sending fresh waves of intense, buzzing pressure radiating through her pelvis. She felt stretched impossibly wide, violated, the plugs a constant, humming reminder of her degradation. The camera zoomed in on her ass, capturing the obscene sight: the twin bases vibrating visibly against her stretched, puffy rim, the gaping hole struggling futilely around them. Maggie shuffled forward, her movements stiff and awkward, her breath coming in ragged gasps. She clutched her stomach, trying to contain the overwhelming sensations. The chat exploded again, loving her struggle, her vulnerability laid bare.
She made it halfway across the room, towards the velvet-draped window. Ben stopped her there. "Hold," he said. Maggie froze, trembling violently, the plugs buzzing relentlessly. The camera closed in on her face, capturing her tear-streaked cheeks, her glazed eyes, her parted lips. Then it panned down, lingering on her swollen, dripping cunt, glistening obscenely under the lights, untouched since the brutal DP session began. Ben’s voice was a low command. "Show them what they want, Maggie."
Maggie’s hand shook as she lowered it from her stomach. Her fingers, slick with sweat and arousal, hesitated for a fraction of a second above her swollen mound. The chat screamed its approval: ‘FINGER FUCK THAT SLOPPY HOLE!’ ‘MAKE IT GUSH!’ ‘SHOW US THE DEPTH!’ Taking a shuddering breath, driven by the relentless vibration in her ass and the eyes of thousands, Maggie plunged two fingers deep into her own dripping cunt. A guttural moan tore from her throat. She curled her fingers inside, seeking the familiar rough spot on her front wall. The sensation was overwhelming – the deep, buzzing fullness in her ass contrasting violently with the sudden, slick intrusion in her cunt. She began to fuck herself hard and fast, her fingers pistoning in and out, the wet, slapping sounds echoing in the room. Her other hand instinctively flew to her clit, rubbing the swollen nub in frantic, desperate circles, trying to catch the wave of sensation threatening to drown her.
The camera stayed tight on her working hand, capturing every plunge, every withdrawal glistening with her juices. It zoomed in on her stretched asshole vibrating obscenely. Maggie’s head fell back, her fiery hair cascading down her back, her mouth open in a silent scream as the conflicting sensations – the brutal vibration deep in her ass, the frantic fingering of her cunt, the rough circles on her clit – collided. Her hips jerked erratically. She was losing control, teetering on the edge of another brutal climax ripped from her exhausted body. Ben watched silently from the edge of the light, a dark silhouette observing his creation unravel. The plugs hummed. Her fingers slammed home. The chat roared. Maggie’s world narrowed to raw sensation and the relentless, watching eye of the lens.
The vibration in her ass was a raw electric current, the plugs grinding deep as her own fingers pistoned frantically in her cunt. She rubbed her swollen clit in rough, desperate circles, the conflicting sensations tearing incoherent cries from her throat. The camera drank it all in: the glistening stretch of her asshole around the humming plugs, the frantic plunge of her hand, the tears tracking through the sweat on her cheeks.
"Faster, slut," Ben’s voice cut through her haze, cold and commanding from the shadows near the monitor. "Show them how fucking greedy that cunt is. Make it drool." Her fingers obeyed, slamming deeper, curling hard against her G-spot. A fresh gush of fluid slicked her thighs. "Look at that fucking mess," he sneered. "Chat wants it messier. They want you overflowing."
Maggie sobbed, her back arching violently as another brutal wave of sensation ripped through her. Her knuckles were white where she gripped her own thigh, anchoring herself against the onslaught. Ben moved then, a dark shape stepping into the light behind her. His hand, slick with the lube he’d grabbed from the nightstand, bypassed her working fingers entirely. He shoved his middle and ring fingers roughly into her slick, stretched entrance alongside her own. Her cunt yielded instantly, a wet, sucking gasp as he speared her to the knuckles.
"FUCK! BEN! TOO MUCH!" Maggie shrieked, her body jolting. Four fingers now filled her, stretching her walls obscenely wide, scraping over her sensitive spots with brutal efficiency. Ben’s fingers worked ruthlessly against hers, a tangled invasion, twisting and spreading her open. The sensation was overwhelming, a deep, burning stretch that stole her breath. He hooked his fingers sharply upwards, grinding the heel of his hand against her clit as he did.
"Hold that leg open, whore," Ben growled, his breath hot on her neck. "Show them how wide you split." With a choked gasp, Maggie obeyed, grabbing the back of her own thigh and hauling it higher, wider, exposing her gaping, violated cunt and the vibrating plugs in her ass to the merciless camera. The position forced her pussy lips apart, revealing the glistening, distended pink flesh stretched taut around the intruding fingers. Ben fucked his two fingers into her relentlessly alongside her own, a wet, squelching rhythm that echoed the buzzing in her ass.
"Look at that," Ben rasped, his voice thick with dark satisfaction. "See how she takes it? Like a fucking fleshlight." He scissored his fingers inside her, stretching her wider, the raw friction making her inner muscles spasm uncontrollably around the intrusion. The combined assault – the brutal fingering, the grinding vibration deep in her ass, the rough pressure on her clit – detonated something primal. Maggie’s scream shattered into a wordless keen as her body locked, rigid.
Then she gushed. Not a trickle, but a hot, sudden flood of fluid erupting from her cunt, soaking Ben’s hand, her own fingers, and pouring down her spread thighs in thick rivulets. It splattered onto the dark carpet beneath her, a visible puddle spreading. Her asshole pulsed violently around the humming plugs as the orgasm ripped through her, a tidal wave of overwhelming sensation that felt less like pleasure and more like her body tearing itself apart. She trembled violently, held upright only by Ben’s hand still buried knuckle-deep inside her and her own desperate grip on her thigh.
"Jesus fucking Christ," Ben breathed, a hint of awe cutting through his control as he felt the hot gush coat his wrist. He slowly withdrew his fingers, glistening and dripping. The camera zoomed in on Maggie’s gaping, dripping hole, juices still seeping out, and the slick trails running down her inner thighs to her knees. Her chest heaved, her eyes rolled back, utterly wrecked. "Hold that gape, superstar," he commanded, his voice regaining its icy edge. "Don't you fucking move." He stepped back slightly, letting the lens capture the full, debauched spectacle: her trembling form, her ravaged holes on display, the evidence of her surrender pooling on the floor. The plugs buzzed on, a relentless counterpoint to her shattered breathing. The chat scrolled too fast to read, a blur of dollar signs and expletives, demanding more, always more.