Chapter 6: Check In and Checked Out
The resort's common area sprawled under a canopy of twinkling fairy lights, the air thick with the scent of jasmine and spilled rum. As the group collapsed into plush loungers, their phones chimed in near-unison, the screen of Emmalina’s device illuminating her triumphant grin as she read the new challenge aloud.
As the group collapsed into plush loungers, their phones chimed in near-unison, the screen of Emmalina’s device illuminating her triumphant grin as she read the new challenge aloud. “It’s a group icebreaker! Two rounds, blindfolds. Group one is all the men… plus Becky.” A competitive spark flashed in Becky’s eyes at being singled out with the guys. “Group two is the rest of us women. We get paired randomly, one from each group, blindfolded. You have two minutes to figure out who you’re with using any method except talking or peeking. Anything goes.” A charged silence settled over the common area, broken only by the distant pulse of reggae from the pool bar. “Touching. Groping. Kissing. You name it. Full submission for points, then we all guess who we had.”
A thick, charged silence followed her words, broken only by the rustle of palm fronds and the distant clink of bottles from the bar. Nicole was the first to move, pulling a silk scarf from her bag with a wicked smirk. “Well? Let’s fucking pair up. Draw straws or some shit?” Someone produced a deck of cards, the chaotic shuffle loud in the quiet. The groupings were decided with brutal simplicity: red cards for Group One—Christopher, Joe, Derek, Justin, and Becky. Black cards for Group Two—Michelle, Emmalina, Michaela, Nicole, and Faith.
They scavenged blindfolds from scarves, belts, and in Justin’s case, a tie from his luggage. The common area, a semi-private patio sectioned off by lush foliage, became their arena. “Group Two, blindfolds on first,” Emmalina directed, her voice tight with anticipation as she tied a sapphire blue scarf over her eyes. Michelle’s hands trembled as she adjusted her glasses before a black sleep mask obscured everything. The world became a hot, dark void of sound: ragged breathing, the shift of fabric on skin.
“Round one. Group Two’s turn to explore. 120 seconds… now.” Emmalina’s voice was the starter pistol.
Emmalina’s voice was the starter pistol.
Michelle’s hands shot out, her fingertips making first contact with a cotton-covered chest. Her heart hammered against her ribs. She mapped the terrain—broad shoulders, a solid torso, the faint, familiar ridge of old scar tissue just below the left collarbone from a long-ago biking accident. Christopher. A wave of dizzying relief and heat flooded her. Her exploring hands grew bolder, sliding down to his waist, her thumbs hooking into his belt loops to pull his hips firmly against hers. She could feel the hard, thick line of his erection already straining against his shorts. She rubbed herself against it, a slow, filthy grind, then sank to her knees on the cool tile.
Her fingers fumbled with his button and zipper, her breath puffing hot against the fabric. She yanked his shorts and boxer briefs down just enough to free his cock, springing heavy and hot into her waiting hands. She didn’t hesitate. She took the full, salty length of him into her mouth in one deep, practiced motion, her lips stretching wide around his girth. She suckled hard at the tip, her tongue swirling around the crown before plunging down again, her throat relaxing to take him deeper. One hand worked the base in a tight, twisting stroke, the other cupped and squeezed his balls, rolling them gently in her palm.
Emmalina, meanwhile, stepped forward into empty space, her hands swiping air until they connected with a shorter, slighter frame. The shoulders were narrow, the hair under her searching fingers was soft and chin-length. Becky. A grin spread beneath her blindfold. Her hands plunged downward, finding the impressive, weighty swell of breasts barely contained in a sports bra. She squeezed them both, kneading the firm flesh, her thumbs seeking out nipples already stiff through the fabric. She ducked her head, mouth finding one peaked nipple through the material, sucking and biting gently.
Her other hand slid down the tight, quads of a triathlete, over the curve of a hip, and pressed firmly against the damp heat between Becky’s legs. Becky jerked, a muffled gasp escaping her. Emmalina rubbed her palm in slow, firm circles against the spandex, feeling the swollen lips beneath. She then brought her wet fingers up, guided them under the blindfold to her own mouth, and tasted the tangy musk. She nodded, confirmation achieved.
Nicole moved like a predator, her hands landing on a tall, lean waist. She snaked one arm around to palm a firm, masculine ass, giving it a proprietary squeeze. Her other hand rose, fingertips tracing a strong jaw dusted with stubble, then up to hair that fell in soft waves to the shoulders. Justin. A current of old electricity snapped between them. She crushed her mouth against his, her tongue invading instantly, a fierce, claiming kiss. Her hand left his hair and shot between their bodies, gripping the rigid bulge in his pants hard enough to make him grunt into her mouth.
She unzipped him with brutal efficiency, her small, strong hand wrapping around his bare shaft. She stroked him fast and rough, her thumb smearing the bead of pre-cum over the sensitive head. She dropped her head again, taking just the tip between her lips and sucking viciously, her tongue flicking the slit before pulling off with a wet pop. She used her own saliva-slicked hand to jerk him faster, her rhythm punishing and expert, a reminder of history no one ever spoke of.
Michaela’s approach was tremulous. Her hands fluttered against a polo shirt, tracing the outline of a body that was fit but softer, less defined. The scent was clean, a familiar detergent. Derek. A complex knot of frustration and reluctant affection tightened in her chest. Her exploration was methodical: the slight paunch over his belt, the curve of his shoulders, the short, trimmed hair. It felt like a marital audit conducted in the dark. She leaned in, her nose brushing his neck, inhaling the familiar scent, but no spark ignited.
Following the rules, her hands moved to his belt, unbuckling it with wifely familiarity. She reached into his trousers, finding him semi-hard. She stroked him dutifully, her touch mechanical, her mind a thousand miles away until she felt him thicken slightly in her hand. A sigh escaped her, part resignation. She quickened her pace, her other hand cupping his balls, her movements proficient but devoid of the hunger that crackled around the others.
Faith’s manicured hands encountered a broad, solid chest covered in a fine, curly pelt of hair. Joe. She could smell Emmalina’s perfume lingering on him. Her exploration was sensual, almost clinical in its thoroughness. She mapped the topography of his chest, pinching his nipples until they pebbled, then trailing her nails down his happy trail. She found him fully hard, his cock straining against his chinos. She freed him, her grip firm and knowing.
She dropped to her knees without a sound, taking him not into her mouth, but between her enhanced breasts. She squeezed them around his shaft, creating a warm, soft valley, and began to slide him up and down through the slick cleft. She tipped her head forward, letting her tongue dart out to lap at the head with each upward stroke. It was a polished, pornographic performance, designed to overwhelm and disorient. She timed it perfectly, bringing him to the trembling edge right as Emmalina’s voice cut through the heavy breathing.
“Time! Step back. Blindfolds stay on. Group One, get ready for your turn. Then we guess.”
A frantic, silent shuffling commenced as pairs were broken apart and new ones formed in the dark. The air was thick with the smell of sex, sweat, and spilled cocktails. Michelle, back on her feet, trembled, her lips swollen and chin damp. Christopher’s taste was still on her tongue. She heard someone—Faith, she thought—adjust a bra strap with a soft snap.
“Round two. Group One explores. Now.”
Rough, eager hands grabbed Michelle’s shoulders from a new direction. These hands were larger, hotter, more desperate than Christopher’s. They slid down her arms, then cupped her breasts violently through her blouse, thumbs grinding her nipples. A mouth crashed against hers, the kiss sloppy and aggressive, all tongue and teeth. Justin. The realization came with a jolt. His hands groped down her back, clutching her ass, pulling her against the hard proof of his arousal.
He spun her around, bending her forward over the arm of a nearby lounge chair. She felt him yank her sundress up around her waist, his fingers hooking into the sides of her thong and tearing it down her thighs. The humid night air hit her bare skin. He didn’t bother with finesse. She heard the tear of a condom wrapper—a dim, rational part of her mind noted its presence—and then the thick, blunt pressure of him notching at her entrance.
He shoved into her with one deep, brutal stroke, filling her utterly, stretching her. A choked cry was muffled by the cushion. He fucked her with fast, driving snaps of his hips, his body slapping against hers, his hands gripping her hips hard enough to bruise. “Fuck, you’re tight,” he grunted, the words hot against her neck, his rhythm punishing and exhilarating. She came suddenly, a sharp, shocking convulsion around his invading cock, her fingers clawing at the chair fabric.
Nearby, Emmalina was laughing breathlessly as calloused hands—Christopher’s, she knew instantly by their size and the scrape of his wedding band—found her waist. He lifted her like she weighed nothing, seating her on the edge of a patio table. He pushed her dress up, buried his face between her thighs, and ate her out with ruthless, focused intensity. His tongue was a broad, flat stroke followed by quick, pinpoint flicks on her clit. She tangled her hands in his hair, grinding against his mouth, her head thrown back.
“Yeah, right there, fuck,” she hissed, no longer caring about silence. He slid two fingers inside her, curling them, scissoring them, stretching her as his tongue never stopped. Her climax ripped through her, a silent, back-arching scream as she flooded his mouth.
Becky, paired with Derek, was guiding his hesitant hands over her body with impatient authority. She made him squeeze her tits, then shoved his head down toward them. He took a nipple into his mouth through her top, suckling clumsily. Her hand was wrapped around his cock, jerking him with a smooth, urgent rhythm that felt nothing like his wife’s touch. “Harder,” she whispered fiercely against his ear, biting the lobe, and he complied, his movements growing frantic.
Michaela stood frozen as gentle, almost reverent hands framed her face. The thumbs that stroked her cheeks were soft. The kiss that followed was tender, questioning, a bare brush of lips. Joe. Her heart ached with a strange pity. His touch remained shy, exploring her arms, her back, but going no further, a stark contrast to the carnal noises surrounding them. She took his hand and placed it on her breast, a gesture of kindness, and he cupped it gently, his thumb making a single, respectful pass over her nipple.
Faith found herself with her back against a post, a body pressed flush against hers. The hips that rocked into hers were female, strong and lean. Becky, again? Sharp teeth nipped at her neck. A hand shoved aggressively between her thighs, rubbing her through her silk shorts with a rough, circular pressure that brooked no argument. Faith moaned, her head thudding back against the wood, her own hands clutching at a muscular back as the skilled fingers worked her toward a swift, sharp orgasm.
“Time!” Emmalina yelled again, her voice ragged. “Blindfolds off. Now fucking guess.”
A chaotic tableau of dishevelment and flushed skin was revealed under the fairy lights. Michelle, still bent over the chair with her dress around her waist, turned her head to see Justin pulling up his shorts, a cocky smile on his face. Christopher was wiping his mouth on the back of his hand, his eyes locking on Michelle’s exposed position with a dark, possessive flare. Joe looked stunned, his lips parted. Derek was panting, his shirt untucked.
“I had Chris,” Michelle whispered, standing shakily, pulling her dress down.
“Becky,” Emmalina stated, shooting a grin at the blushing triathlete.
“Justin,” Nicole said, lighting a cigarette with steady hands, her gaze challenging.
“Derek,” Michaela mumbled, not meeting anyone’s eyes.
“Joe,” Faith said smoothly, adjusting her hair.
The guesses for the second round flew, most correct, all confirming the tangled web of touch that had just been woven. The app chimed victoriously, signaling a massive point haul for the entire group. A collective, adrenaline-soaked laugh bubbled up, tense and wild.
“Fuck,” Christopher breathed, his eyes still devouring Michelle. “Let’s see what that bought us.” He pulled out his phone. The next challenge glowed on the screen, its text simple and incendiary. ”Public Cumshot. Partners must remain in the pool lounge area. One gives, one receives, in full view of at least ten non-group witnesses. Location choice multiplies points.”