Cover of The Curious Case of Hillary and Dana

The Curious Case of Hillary and Dana

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Hillary and Dana are a lesbian couple who are both bisexual. After hearing that Bryan has a huge cock from Shay, they decide to trick or convince them into showing it to them. Astounded by the size of it, they take turns playing with it, measuring it, and attempting to deep-throat it unsuccessfully.

Chapter 1: A Big Surprise

The air in Shay’s apartment was thick with gossip and the sharp, sweet scent of cheap wine. Hillary lounged on the worn couch, while Dana perched on the armrest, both leaning in as Shay’s voice dropped to a conspiratorial whisper.

“No, seriously you guys,” Shay hissed, her eyes wide. “I’m not fucking around. Bryan is hung. I mean, a legitimate monster. I almost called an exorcist last night.”

Dana snorted into her glass. “Bullshit. Everyone says that.”

“I’m measuring from the base,” Shay insisted, her hands held a comical distance apart. “It’s like holding a fucking Red Bull can. I could barely get my mouth around it.”

Hillary’s eyebrows shot up. “You tried?”

“Of course I tried, it was right there!” Shay laughed, the sound cutting off abruptly as the bathroom door clicked open down the hall.

Steam billowed out first, followed by Bryan. He padded barefoot across the laminate floor, a thin white towel slung low on his hips. Damp hair dripped onto his broad shoulders. He offered a casual, “Ladies,” his voice a low rumble, and moved past them toward the bedroom without breaking stride.

The three women fell silent. Dana’s glass halted halfway to her lips. Hillary’s gaze was blatant, tracing the V of his torso leading down to where the towel knotted. The terry cloth strained, outlining a substantial, soft weight against his thigh.

The bedroom door closed softly behind him. A beat of silence hung in the air, then shattered.

“Holy shit,” Dana breathed, finally blinking.

“See?” Shay whispered, a triumphant, filthy grin spreading across her face. “Told you. That towel is a fucking liar.”

From behind the door, they heard the distinct sound of a drawer opening, then the soft rustle of fabric. Hillary drained her wine in one gulp. “Okay. I officially retract my skepticism.”

Shay leaned back, satisfied. “Told you. Now, who wants to hear what he can actually do with it?” The story was just beginning.

The story was just beginning. Shay’s voice dropped to a bare whisper, a wicked glint in her eye. “Okay, look. He’s going to come back out to grab his phone or a beer. I’ll ask him to get the bottle of tequila from the high kitchen cabinet.”

Dana smirked. “The one above the fridge.”

“Exactly. He’ll have to reach. I’ll say the towel’s slipping and point, he’ll look down…” Shay mimed a distracted adjustment. “You two are the distraction. Hillary, you ‘accidentally’ spill your wine on the floor near his feet. Make a big deal.”

Hillary nodded, already plotting her fumble. “He’ll bend down to help.”

“And Dana,” Shay continued, “you’re closest to the lamp. As he’s bent over, just… flick it off.”

“Blackout,” Dana breathed, a giddy smile spreading.

Shay leaned in. “Count of three after the light goes. We all just… reach. Whoever gets there first gets confirmation. Go for the knot.”

A floorboard creaked in the hall. The three of them snapped back, feigning casual sips of wine as Bryan emerged, now in grey sweatpants and nothing else, his hair still damp. He moved toward the kitchen.

Shay’s voice was syrupy sweet. “Babe, can you grab that gold tequila? It’s above the fridge.” He nodded, turning his back to them, stretching upward. The sweats pulled taut, outlining the full, heavy curve of his ass and the undeniable, thick drape of his cock against his thigh.Now. Hillary jerked her arm, sending a wave of crimson Merlot splashing across the floorboards at his feet. “Shit! God, I’m so clumsy!”

Bryan turned, immediately crouching. “It’s fine, I got it.” He reached for a roll of paper towels.

“Three,” Shay mouthed. Dana’s hand snaked out and clicked the lamp switch.

Darkness swallowed the room, punctuated by the glow of a distant streetlight. They moved in the dim blue haze. Three sets of hands found him in the sudden void. Fingers grasped at the loose waistband of his sweats, pulling them down in one sharp yank. He grunted, a sound of pure surprise.

Cool air hit his skin. The sweats pooled at his ankles. He was trapped, crouched and exposed.

“What the fuck—” he started, but it was too late. Somebody’s phone flashlight flared, a brutal white beam cutting through the dark.

It landed directly on his groin. The gasp was collective, sharp.

There was no denying it.

There was no denying it. The flashlight beam was clinical, unforgiving.

It lay thick and heavy against his thigh, even soft, a obscene curve of flesh that made Dana’s breath hitch. “Jesus Christ,” she whispered.

Shay’s hand, the one that had pulled his sweats down, didn’t retreat. Her fingers traced the thick vein running along the side. “Told you,” she said, her voice husky.

“We need proof,” Hillary insisted, her earlier clumsiness gone, replaced by a hungry curiosity. “A real measurement.”

Bryan didn’t move, crouched in the dark, his breathing audible. “You’re fucking insane,” he muttered, but it lacked conviction; there was a rough edge of arousal in his tone.

Dana already had her phone out, the measuring app open, its digital tape glowing in the dark. “From the base,” she said, her voice all business. “Press into the pubic bone. Shay, hold it straight.”

Shay’s fingers encircled him, firm, pulling him out to his full, softening length. The touch made him twitch, blood beginning to pool. Dana placed the phone’s zero point hard against his skin, pushing into the coarse hair.

She slid the virtual tape along the top. The numbers glowed. Seven and a quarter inches. Soft.

“For science,” Hillary giggled, nervous energy crackling.

“Now the girth,” Shay commanded. Dana fumbled for a loose hair tie from her wrist. She looped it around the middle, snug, then lifted it off and held it against the phone’s screen. A circumference. They all leaned in, the flashlight trembling.

The digital ruler read five and a half inches around.

“Holy fucking shit,” Hillary breathed, the number making it real.

Bryan finally stirred, a low groan escaping him as he began to harden fully under their scrutiny, the flesh in Shay’s grip swelling, thickening, becoming a solid weight. “Satisfied?” he growled, the humiliation twisting into something darker, more collaborative.

“Not even close,” Shay said, and her other hand joined the first, beginning to pump.

“Not even close,” Shay said, and her other hand joined the first, beginning to pump.

"Let me," Hillary said, her voice tight. Her fingers replaced Shay’s, her grip slightly tighter, her rhythm more urgent. Bryan’s head fell back against the cabinet with a thud, his hips pushing forward into her fist.

Shay vanished into the bedroom, returning a moment later with a small digital camcorder, its red recording light already glowing like a malevolent eye. She panned it slowly from Bryan’s strained face down the tense line of his body.

"Scientific method," Shay narrated softly behind the lens. "We need the control variable. Dana."

Dana was already there with the phone. Bryan was fully erect now, a thick, veined shaft jutting obscenely from his body, the head flushed a dark, angry purple. Hillary kept stroking, a slow, steady pump that made pre-cum well and drip.

"Base," Dana instructed, her voice clinical. Hillary’s hand stayed at the root, holding him still as the phone was pressed hard into his pubic bone. The digital tape flashed.

"Eight and a half," Dana announced, a reverent whisper.

"Girth now."

The hair tie was stretched taut. Six inches around. The proof was irrefutable, captured in the camcorder’s unblinking gaze. Bryan was panting, his muscles corded. "You’ve got your data," he gritted out.

Shay lowered the camera, her smile predatory. "Now we test application."

Shay’s declaration hung in the dark room like a challenge. Hillary never broke eye contact with Bryan as she leaned in, her voice a low, impressed murmur. “It’s a fucking masterpiece.” She pressed her lips to the swollen, slick tip in a soft, mocking kiss.

Then she glanced over her shoulder at Dana, a sly grin spreading. “A hundred bucks says you can’t take it all.”

“You’re on,” Dana said, pushing Hillary aside without hesitation. She dropped to her knees on the wine-stained floor, her hands gripping the base. She took the head into her mouth, her jaw stretching wide, and began to push forward. She made it about halfway down the thick shaft before her body convulsed, gagging violently. She pulled off, gasping, saliva stringing from her lips.

She tried again, forcing herself deeper, her eyes watering. Another wet, choking sound echoed in the quiet apartment. On the third attempt, she managed another inch before stumbling back, shuddering. “Fuck,” she coughed, wiping her mouth with the back of her hand. “No bet. It’s impossible.”

She looked up at Bryan’s flushed face, then at Shay behind the camera. “I want to know what it actually feels like.”

“I want to know what it actually feels like.”

Hillary’s eyes flickered. “Then take it, you fucking quitter. Don’t tap out now.” Her voice was a low challenge in the dark. “Get back down there.”

Dana wiped her mouth again, steeling herself. She leaned forward once more, opening wide. Just as she started to bob, her body tensing for the inevitable gag, Hillary’s hand shot out.

It wasn't gentle.

She grabbed a fistful of Dana’s dark hair, waited for the moment Dana’s lips slid over the flared head, and drove her down hard. Dana’s muffled shriek was wet and choked, her throat violently clenching around the invading thickness. Her body jerked, a wild, panicked tremor. Bryan gasped, his head thudding back against the cabinet.Again. Hillary pulled her off, a strand of saliva snapping, then shoved her face back onto the wet shaft, deeper this time. Dana’s nails clawed uselessly at the laminate floor. Her throat made a ragged, involuntary noise of pure shock with each brutal thrust.

The fourth try was a slow, steady pressure. Hillary didn’t relent, holding Dana’s head firmly as her nose finally pressed into the wiry dark hair at the base. Hillary’s expression was one of utter, clinical triumph. The red light of the camcorder shone on Dana’s heaving back.

“Holy shit,” Shay breathed from behind the camera, the lens focused tightly on the grotesque join. “Look at that. It looks even bigger in her. Fucked up optical illusion.” It pulsed visibly in the strained prison of Dana’s throat, thicker and more monstrous than before.

She shoved Dana’s head away roughly, gasping wetly as her hot, sticky head popped free.

"We need to measure this," Hillary commanded, her tone predatory, picking up the phone again. "Hold it steady."

As Dana crawled aside, Hillary forced the phone hard against Bryan’s wet pubic bone while Shay gripped the base. Dana reclaimed the hair tie, her hands shaking. They stretched the tiny band of elastic until it became a ringed circle, holding it against the screen. The numbers glowed in the digital silence of the room.

Bryan was gritting his teeth now, raw power obvious in his every muscle, he forced it all the way down him. "Eleven fucking inches," Shay announced, voicing the digits on the screen, a whisper of genuine awe that held nothing clinical, only carnal."And look!" Dana pressed the circumference measurement into the glaring phone screen: a blood-throbbing 10 full inches of veined, unbelievable flesh.

Dana pressed the circumference measurement into the glaring phone screen: a blood-throbbing 10 full inches of veined, unbelievable flesh.

“My turn,” Hillary declared, shoving the phone back into Shay’s hands. She got on her knees, her determination clear in the set of her jaw. She took him into her mouth with a wet, sucking sound, her hands working the base. She pushed, gagging instantly, pulling back with a string of saliva. “Fuck,” she muttered, wiping her lips. She tried again, deeper this time, her throat convulsing violently as the thick head hit her tonsils. She pulled off, gasping for air, her face flushed with effort and humiliation. “Goddamn it.”

A third attempt, a frantic, choking bob, ended the same way. Rage flickered in her eyes. “Stupid fucking thing,” she hissed, and before anyone could react, she flicked her thumb hard against one of his swollen balls.

Bryan grunted, a sharp, pained sound, his body flinching. “What the hell?” Shay lowered the camera, her voyeuristic smile vanishing. The room’s charged, predatory energy shattered into something brittle and dangerous. Bryan looked down at Hillary, his arousal now mixed with something colder, a darkening glint in his eyes as he caught his breath.

Bryan looked down at Hillary, his arousal now mixed with something colder, a darkening glint in his eyes as he caught his breath.

“Shit, fuck, I’m sorry,” Hillary whispered, the fight draining from her voice. She leaned in, pressing her mouth in a soft, apologetic kiss to the reddened skin of his ball, her tongue tracing a slow circle. “I got pissed off at myself.” Her hand wrapped around his shaft again, starting a slow, twisting stroke from the base. “Dana, get over here. Suck the head, play with his balls. Be nice.”

Dana crawled forward, her earlier struggle forgotten. She took the slick, purple head into her mouth, hollowing her cheeks as she began to suck with wet, noisy pulls. Her fingers gently cradled his sac, rolling the heavy weight.

Hillary worked the thick length in a firm, steady rhythm, her thumb smearing pre-cum over the flared ridge. “See?” she murmured, watching his face. “We’re good.”

Bryan’s jaw was tight, a muscle ticking in his cheek, but his hips began a subtle, involuntary thrust into their synchronized grips. A low groan vibrated in his chest.

“Look at that,” Shay said from behind the camera, her voice a knowing whisper. “I think he actually likes it a little rough. The apology just made it better.” The red light gleamed on the sheen of sweat now coating his stomach.

The red light gleamed on the sheen of sweat now coating his stomach. Bryan’s breathing turned ragged, a staccato rhythm that filled the quiet room. “Fuck, I’m gonna—” he choked out, the words tight and strained.

“Now,” Hillary commanded, her voice stripped of all playfulness. “Dana. Shirt and bra. Off. Now.” Her hand never stopped its ruthless, twisting pump.

Dana scrambled back from his balls, her fingers fumbling with the buttons of her blouse. She tore it open, sending a button pinging across the floor, then wrestled her bra clasp open. Her small breasts fell free. “Open your mouth,” Hillary ordered, her own focus entirely on the pulsing, iron-hard shaft in her grip. “Wider. Stick your tongue out.”

Bryan’s hips jerked violently, his control snapping. A guttural, animal sound tore from his throat as the first thick, pearlescent rope launched from him. It hit Dana’s tongue with a wet slap, the force of it making her flinch. The second shot streaked across her cheekbone. The third, a massive, continuous spurt, painted her chest, glazing her nipple and oozing down the curve of her breast.

He kept coming, the torrent unreal, painting white stripes across her skin until her face and tits were slick and dripping. The final pulses were weaker, dribbling onto the mess below. A heavy, spent silence descended, broken only by Bryan’s harsh gasps. They all stared, mesmerized, at the obscene, glistening proof covering Dana. The sheer volume was shocking, a pool of it gathering in the hollow of her collarbone. “Jesus fucking Christ,” Shay whispered from behind the camera, the red light still glowing.

“Jesus fucking Christ,” Shay whispered from behind the camera, the red light still glowing.

“Don’t waste it,” Hillary said, her voice calm and commanding. She nudged Dana’s shoulder with her knee. “Lick it off. Clean your own tits. Show him you appreciate it.”

Dana’s eyes, wide and stunned, met Bryan’s for a second before she looked down at the mess glazing her skin. She hesitated, her tongue darting out to wet her lips. Then she bent her head, a sharp, unnatural motion, and dragged her tongue in a long, slow stripe from her sternum up to her collarbone. She gagged softly at the taste, salty and bitter, but forced another lick, capturing a thick glob that had slid toward her nipple. She sucked it into her mouth, her throat working as she swallowed.

She sucked it into her mouth, her throat working as she swallowed.

Hillary watched, her breathing shallow. “Your face is still a mess,” she muttered, her voice thick. She leaned in, her tongue dragging a wet, deliberate stripe from Dana’s jawline up to her cheekbone, collecting the cooling streaks. Dana whimpered, turning her head to meet Hillary’s mouth in a sloppy, open kiss that tasted of salt and sex. They shared the bitter residue, their tongues sliding together until Dana’s skin was clean and shining only with saliva.

“Fuck,” Hillary breathed, pulling back, her eyes dark with a hungry heat. Her fingers hooked into the waistband of her leggings and panties, shoving them down her hips in one frantic motion. She kicked them away, standing naked from the waist down. “Your turn. Now. Get your mouth on me.” She grabbed a fistful of Dana’s hair, guiding her head between her spread thighs.

Dana’s tongue pressed against her, licking a broad, flat path through her folds. She worked clumsily at first, then found a rhythm, her lips closing around Hillary’s clit to suck hard. Hillary gasped, her hips rocking forward. “Yes, just like that, you fucking slut, make me wet.” Soon, a slick, audible shine coated Dana’s chin, and Hillary’s thighs were trembling. “Enough.”

She pushed Dana aside and turned, bending over the kitchen counter, her palms flat on the sticky laminate. “Bryan. Now. I don’t want a gentle fucking touch.” Bryan, who was fully hard again, thick and angry-looking, stepped behind her. He positioned himself, the broad head of his cock nudging against her soaking entrance. He pushed in with one brutal, deep thrust, burying himself to the hilt.

A sharp, ragged cry tore from Hillary’s throat, her knuckles white on the countertop. “Oh god, it’s too much,” she gasped, the pain cleaving her in two. “Don’t you dare stop. Fuck me harder.” He obeyed, pulling back and slamming home again, setting a punishing rhythm that made the cabinets rattle.

The sound was meaty, wet, and sharp. Hillary’s scream wasn’t pain; it was a raw, greedy command that ripped from her throat. “Harder, you bastard! Don’t you fucking stop!”

Shay kept filming, the red light a tiny cyclops eye in the dark, capturing the violent red handprint blooming on Hillary’s skin and the brutal, piston-like drive of Bryan’s hips. Dana watched for a second, her own breath coming fast, then crawled closer on the sticky floor. Her fingers, slick with her own saliva from before, wrapped around the tight, heavy sack beneath Bryan’s shaft. She squeezed gently at first, then rolled the weight in her palm, tugging just enough to make him grunt.

The new sensation shot through him, a jolt of rough pleasure that made his next thrust stumble, going deeper, twisting. “Fuck,” he snarled, his rhythm fracturing into something more frantic, more animal.

Hillary felt the change, the uncontrolled surge. “Yes! Like that!” she chanted, her voice breaking on each slam. Dana increased the pressure, her nails lightly scraping the sensitive skin, feeling the cords tighten as Bryan swelled even thicker inside Hillary, pulsing toward his limit. The camera watched, unblinking, as everything tightened, poised to break.

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