Cellar Aged Cravings: Our Holiday Fling's Last Anal

The gravel drive crunched under the tires of Hana’s rental as she rolled up to the old vineyard estate, the place her family still pretended was charming instead of a money pit dressed in holiday lights. Twinkling bulbs clung to the eaves of the main house. Somewhere inside, someone had already started on the mulled wine. She killed the engine, sat for a second with her hands on the wheel, and told herself she was only here for Christmas, for her mother’s sake, for the usual bullshit. Not because she’d checked three times whether Emmett might be around.

He was her stepbrother Sergio’s best friend. Thirty-two, filthy-mouthed, built like he still worked the vines even when he didn’t have to. Two summers ago they’d spent a secret week destroying each other in guest rooms, in the tasting barn, once bent over a crate in this very cellar while the rest of the family slept off too much Cabernet. She’d left with bruises on her hips and his cum still leaking out of her ass on the drive to the airport. They hadn’t spoken of it since. Hadn’t spoken much at all.

She hauled her bag inside, kissed cheeks, endured the noise. Miriam pressed a glass into her hand. Sergio clapped her on the shoulder and said Emmett had driven up that afternoon, was around somewhere, probably scrounging bottles for tonight. Hana’s cunt clenched so hard she nearly spilled the wine.

She lasted forty minutes before the excuse presented itself. Someone wanted the ’09 reserve for dinner. The special bottle. Down in the cellar. She volunteered before anyone else could open their mouth, grabbed the heavy key from the hook, and escaped into the cold evening air that led to the stone steps.

The cellar smelled like damp oak and old fruit. Rows of racks disappeared into shadow. A single bare bulb burned near the far wall. She was halfway down the center aisle, fingertips trailing dusty labels, when the door at the top of the stairs thudded shut and boots descended.

Emmett.

He looked the same and worse—broader in the shoulders, jaw rough with stubble, flannel shirt open at the throat like he’d been working. His eyes found her immediately and didn’t pretend politeness.

“Hana.” Her name came out low, almost a laugh. “Of course it’s you hunting the good shit.”

“Someone had to.” She kept her voice steady even as heat flooded between her legs. “Sergio said you were around.”

“Been around.” He came closer, not rushing, boxing her in between two tall racks of Pinot. The space narrowed. She could smell him—soap, sweat, the ghost of whatever he’d been drinking. “Kept wondering if you’d show your face this year. Or if you’d keep running.”

“I wasn’t running.”

“Bullshit.” He stopped close enough that her breasts nearly brushed his chest when she breathed. “You ghosted after that week. Left me with a raw dick and the memory of you begging me to stretch your tight little asshole again before you got on the plane. You remember that part, or do you need a refresher?”

Her nipples tightened hard under her sweater. She didn’t step back. “I remember everything. The way you spit on it. The way you made me thank you every time you bottomed out.”

Emmett’s mouth curved. He reached past her, deliberately brushing her hip, and tugged a bottle free like that was the point of any of this. “Still wet for it, then.”

“Fuck you.”

“That’s the idea.” He set the bottle on a nearby crate without looking away from her face. “I’ve jacked off to you bending over in this cellar more times than I can count. Two summers and I still wake up hard thinking about how your cunt dripped down your thighs while I fucked your ass. Tell me you haven’t done the same.”

Hana’s pulse hammered in her throat. The admission sat right there, filthy and true. “I’ve thought about it every time I put a plug in. Every time I finger myself and it’s not enough. I wanted your cock back in me the second I drove through the gates.”

He made a rough sound and closed the last inch. One hand braced on the rack beside her head. The other settled on her waist, thumb stroking under the hem of her sweater until he found bare skin. “Say it plain. You’ve been craving this.”

“I’ve been craving your body,” she said, voice gone hoarse. “Your hands. Your mouth on my tits. Your dick splitting me open. Especially my ass. I haven’t let anyone else near it since you. It still feels like yours.”

Emmett’s fingers dug in. He leaned down until his breath warmed her ear. “Good. Because I’ve been saving up for the next time I get you alone down here. Going to wreck that hole again until you’re shaking and sloppy and begging me not to stop. Holiday fling’s last anal, yeah? Make it count before we have to pretend we’re just polite strangers at the dinner table.”

She turned her face toward his. Their mouths almost touched. “Then stop talking and put your hands on me.”

He did. Both palms slid under her sweater, shoved it up, found the thin bra and yanked the cups down so her breasts spilled heavy into his hands. He thumbed her nipples hard enough to make her gasp, then pinched and rolled them while he shoved a thigh between hers. She ground down on the hard muscle without shame, already soaked through her panties.

“Christ, you’re hot for it,” he muttered, mouth dragging along her jaw. “I can feel how wet you are through your jeans. You come down here hoping I’d follow? Hoping I’d pin you against the racks and remind you who owns that greedy little hole?”

“Yes.” No point lying. She arched into his hands, rubbing her cunt against his thigh in short, desperate strokes. “I wanted you to corner me. I wanted you to make me admit it.”

Emmett kissed her then—filthy, open-mouthed, all tongue and teeth. She moaned into it and sucked on his tongue like she wanted it deeper. His cock was a thick ridge against her hip; she reached down and squeezed him through his jeans, feeling him jump.

“Fuck,” he growled against her lips. “Keep doing that and I’ll have you bent over a barrel with your jeans around your ankles before anyone notices we’re gone.”

“Do it.” Her free hand fumbled at his belt. “I don’t care. I need it. Need you back inside my ass where you belong.”

He caught her wrist, not stopping her exactly, just slowing the scramble. His eyes were dark, pupils blown. “Not yet. Not rushed. I’m going to take my time getting you ready. Fingers first. Maybe my tongue if you ask nice. Then I’m going to feed every inch into that tight ring and fuck you until you can’t walk straight to dinner. But first—” He spun her, sudden and sure, so her chest pressed to the cool wood of the wine rack. Bottles clinked softly. His body crowded hers from behind, cock nestling against the cleft of her ass through their clothes. One hand snaked around to pop the button of her jeans. “First you’re going to tell me exactly how you’ve been touching yourself thinking about me.”

Hana pushed back against him, shameless. The zipper rasped down. His fingers slid under the waistband of her panties and found her slick and swollen without preamble. Two thick fingers rubbed over her clit, then lower, gathering wetness, teasing her entrance before dragging back to press against her asshole through the thin cotton.

“I’ve fucked myself with a dildo thinking it was you,” she panted, forehead against a dusty shelf. “Pushed it into my ass while I watched porn and pretended the guy was you. Came so hard I cried once. Still wasn’t enough. Still empty after.”

“That’s because nothing else stretches you like I do.” He bit the side of her neck, not gentle, and worked a finger past the edge of her panties to stroke bare, sensitive skin right over her hole. “This is mine for the holidays. Say it.”

“It’s yours.” She was already trembling. “My ass is yours. Please, Emmett—”

A voice echoed faintly from upstairs, someone calling about the bottle, about dinner starting soon. Emmett’s hand stilled but didn’t leave her. His mouth stayed hot against her ear.

“We’re not done,” he said, quiet and filthy. “You’re going to grab that reserve, walk back up there with my fingers still smelling like your cunt, and sit through the whole fucking meal knowing I’m going to finish this the second I get you alone again. Tonight. Down here. Or in your room. I don’t care who hears you beg.”

He pulled his hand free, brought the glistening fingers to her mouth, and pushed them past her lips. She sucked without being told, tasting herself, tasting the promise.

“Good girl.” He fixed her bra and sweater with rough efficiency, zipped her jeans enough to be decent, then picked up the bottle she’d originally come for and pressed it into her hands. His cock still strained obviously against his fly. “Go. Before I change my mind and make you take it right now with the door unlocked.”

Hana’s legs felt unsteady. She clutched the bottle, turned in the narrow space, and looked at him one more time—at the hunger openly carved into his face, at the way his chest rose and fell.

“Don’t make me wait too long,” she said.

“Wouldn’t dream of it.” His smile was pure filth. “Now move. And Hana? When you sit down at that table, I want you thinking about how hard I’m going to fuck your ass later. How deep. How I’m going to fill it until it’s dripping down your thighs under the Christmas lights.”

She climbed the stairs on shaky legs, the cold air hitting her flushed face, the taste of herself still on her tongue, and the unbearable ache between her legs promising that this—whatever this still was—had only just started burning again.

She made it through the door with the bottle cradled against her chest like something fragile, face still hot, thighs slick. The kitchen noise hit her first—Miriam’s laugh, Sergio arguing about corkage, someone clattering plates. Emmett followed a full minute later, the perfect picture of casual, the bulge in his jeans only mostly tamed. He caught her eye across the room while she handed over the reserve and mouthed later without moving his lips.

Dinner was torture. They sat her three seats down from him, close enough to watch the way his throat worked when he swallowed wine, far enough that every accidental brush of knees under the long table felt deliberate. She crossed her legs tight and still felt the ghost of his finger circling her hole. Every time someone passed the bread she imagined his cock instead—thick, veined, the one that had split her open two summers ago until she sobbed thank-yous into a wine crate.

Halfway through the roast, Emmett’s boot found her ankle. Slow drag up her calf. She nearly dropped her fork. He didn’t look at her. Just kept talking to Sergio about yields while his foot stroked higher, nudging between her knees until she let them fall open under the tablecloth. The pressure against her still-damp jeans made her cunt clench around nothing.

“You all right, Hana?” Miriam asked. “You’re flushed.”

“Wine,” she lied, voice too tight. “Went down the wrong way.”

Emmett’s mouth twitched. Under the table his boot pressed firmly against her mound, rubbing once, twice, enough to make her bite the inside of her cheek. She shifted forward, shamelessly grinding just enough for friction, and watched his jaw flex.

By dessert the tension was a live wire. She excused herself to “check something in the cellar” before anyone could volunteer. Emmett waited exactly four minutes—long enough for the others to start the coffee ritual—then followed.

The door thudded shut behind him the same way it had earlier. This time the bare bulb threw harder shadows. She was already waiting by the stack of empty oak barrels near the far wall, the ones they used for display, her back to him, sweater peeled off and tossed aside so she stood in just the thin dress she’d changed into after the first round of hugs. No bra. The fabric clung to the hard points of her nipples.

“Thought you’d make me wait till midnight,” she said without turning.

“Couldn’t. Not after watching you squirm through three courses with my spit still drying on your neck.” He crossed the stone floor, boots loud. “You remember how it used to go, don’t you? You’d get that look—same one you had at the table—and start begging before I even got my zipper down. ‘Please stretch my ass, Emmett. Please ruin it. I’ll be so fucking good.’ You used to say it like a prayer.”

Hana’s laugh came out shaky. She braced both hands on the top barrel and arched her back, ass pushing toward him. “I remember. I remember coming so hard I blacked out the night before I left. And I remember every lonely night since. Years of it. Touching myself in hotel rooms, in my own bed, in the shower with the water too hot, always finishing with two fingers in my ass wishing they were thicker. Wishing they were you. I’d get myself right to the edge thinking about the way you used to spit right on my hole and then shove in without letting me adjust. I’d come empty and furious and still do it again the next night.”

He stopped behind her. Close. Heat radiated off him. “Show me.”

She didn’t hesitate. Fingers gathered the hem of the dress and dragged it up over her hips, higher, until the soft fabric bunched at her waist. No panties—she’d ditched them in the powder room after dinner, still soaked from the first cellar round. Cool air kissed her bare cheeks, the slick seam of her cunt, the tight furl of her asshole. She reached back with both hands, hooked her thumbs into the soft flesh, and pulled herself open. The stretch burned sweetly. She knew exactly what he was seeing: the little pink hole winking, already glistening because she’d been dripping since he first pushed his fingers into her mouth upstairs.

“Christ,” Emmett breathed. “Look at that hungry fucking thing. Been waiting years to get claimed again and it’s already soft for me.”

“It’s yours,” she said, voice raw, forehead dropping to the curved wood. “One last time before we have to go back to pretending. Before the holidays end and I’m on a plane again with nothing but the ache. Fuck my ass, Emmett. Stretch it. Fill it. Make it remember who it belongs to so I can touch myself to the real thing instead of a memory for the next decade.”

His hands replaced hers—rougher, bigger, spreading her wider until the rim fluttered. A thick thumb dragged through the wetness coating her cunt, scooped it up, and smeared it over her asshole in slow circles. She pushed back into the pressure, shameless.

“You’ve been keeping it tight for me,” he muttered, pressing just the pad of the thumb against the center until the muscle gave a little. “No one else. Just toys and your own fingers and the filthy fucking fantasy of my cock. Say it again. Tell me how bad you’ve needed this.”

“I’ve needed it every day.” The words tumbled out filthy and true. “Needed you to bend me over exactly like this and remind me how deep you go. Needed the burn. Needed to feel you throbbing inside me when you come. I used to beg—remember?—I’d say please wreck my ass, please use me, please don’t stop even when I’m shaking. I’m still that girl. Still yours down here in the dark with the barrels and the dust. Put it in me. Claim it one last holiday time before we have to be polite strangers again.”

He growled low and freed his cock with one hand, the heavy slap of it against her cleft making her moan. The blunt head notched against her hole, slick with her own juices, and just rested there—pressure without entry—while he leaned over her back.

“Not yet,” he said against her ear, even as his hips gave a tiny push that made the ring stretch and then bounce back. “I’m going to work you open first. Fingers. Tongue. Make you drip down these barrels until you’re sobbing for it. Then I’ll give you every inch and fuck you so full you’ll feel me when you sit down for Christmas breakfast tomorrow. But you’re going to keep those cheeks spread the whole time. You’re going to show me how pretty that hole looks taking what it craves.”

Hana’s arms trembled but she held herself open, dress rucked high, ass presented like an offering. Outside, faint laughter drifted from the house. Down here there was only the wet sound of his thumb finally popping past the rim, slow and deliberate, and her broken whisper of yes as he started to work her open for the last real claiming of the season.

His thumb sank deeper, twisting as he worked her open, the rim gripping him like it never wanted to let go. Hana moaned into the barrel wood, cheek pressed to the dusty curve, ass still spread by her own shaking hands. Emmett added a second finger without warning, scissoring them slow, stretching that tight ring until she felt the burn bloom hot and perfect. Her cunt dripped steadily onto the stone floor, a thin string of slick connecting her swollen lips to the ground.

“Fuck, listen to that sloppy little hole,” he growled, pumping his fingers in and out. “Sucking me in already. You’ve been starving for this.”

“Yes—God, yes—deeper,” she panted, pushing back to take more. Interior heat coiled low in her belly; every lonely night with toys flooded back, none of them thick enough, none of them him. Two summers of memory crashed through her: the bruises, the leak down her thighs on the airport drive, the way she’d clenched around nothing ever since.

He pulled free suddenly. She whimpered at the empty ache. Then boots scraped and he dropped to his knees behind her. Hot breath ghosted over her exposed hole. Emmett’s tongue dragged a long, greedy stroke right up the center of her ass, flat and wet, from the dripping seam of her cunt all the way over the fluttering rim. He did it again, slower, savoring, burying his face between her cheeks while two thick fingers speared into her pussy without preamble.

Hana cried out, the sound echoing off stone and oak. His tongue circled, then speared, fucking into her asshole with filthy wet thrusts while his fingers curled inside her cunt, stroking that spongy spot that made her knees buckle. He ate her like a man starved—long greedy licks, sucking hard on the rim, tongue plunging deep then pulling back to lap at the stretched edges. Slick noises filled the cellar. Her juices coated his chin; he finger-fucked her harder, three fingers now stretching her pussy while he tongue-fucked her ass open.

“Emmett—oh fuck—your mouth—” She couldn’t form full sentences. Pleasure knifed through her, sharp and dirty. She kept her cheeks spread, presenting, staring at the dark rows of bottles while he ruined her with tongue and fingers. Every stroke made her clench, made more cream drip down his wrist. He groaned into her hole, the vibration shooting straight to her clit.

He licked one final, filthy path, then stood. She heard the wet sound of him spitting into his palm, then the slick stroke of his hand over his cock. The blunt head notched against her loosened rim again. Emmett gripped her hip hard.

“Take every inch,” he ordered, voice rough. “Don’t you fucking tense.”

He pushed. Slow at first, the thick head forcing the ring wide, then one deep relentless thrust that buried him to the root. Hana screamed—raw, broken, pure pleasure-pain as her ass stretched around the full fat length of him. He bottomed out in that single stroke, balls tight against her dripping cunt, cock throbbing inside the clenching heat.

“Jesus Christ, still so fucking tight,” he snarled. He didn’t give her time. Hips snapped back and slammed home again. Standing doggy against the barrels, he fucked her hard—long deep strokes that dragged every ridge over her rim, burying himself so deep she felt him in her guts. The barrels creaked. Bottles rattled. He fisted a handful of her hair and yanked her head back, arching her spine, using the grip for leverage as he pounded her ass.

“Say it,” he demanded, free hand cracking across one cheek hard enough to leave a stinging print. Slap. Another. “Scream how much you love it.”

“I love it—fuck, I love being your anal slut!” The words tore out of her, loud, shameless. Each thrust punched the air from her lungs. “Love your fat cock stretching my ass—love when you slap it and pull my hair and use me—I’m your filthy fucking anal slut, Emmett, wreck me, please don’t stop—”

He growled approval and fucked her harder, the wet slap of skin on skin filthy and constant. Her tits bounced under the rucked dress. Slick from her cunt smeared his balls and thighs. He pulled her hair tighter, slapped her ass again and again until both cheeks burned hot and red, until she was babbling yes and harder and fill me. The burn of the stretch never faded; it only deepened, perfect, the way she’d craved for years. Every time he bottomed out she saw white at the edges of her vision.

He pulled out abruptly, cock glistening, her hole gaping wet and needy for a second before he spun her and bent her forward over a low wine rack. Bottles clinked in protest. He hooked her legs up and back—almost folded, piledriver-style against the rack so her ass tilted high and open toward him. From this angle he could stare straight down at the ruined little hole as he lined up again.

“Watch,” he ordered, even though she couldn’t quite see. “Feel how wide I stretch you.”

He slammed back in. The position let him drive deeper, let him watch every thick inch disappear into her pink stretched rim, the way it clung and bloomed around his shaft on every withdrawal. Hana’s hands scrabbled for purchase on the rack edges. The new angle lit her up from the inside; his cock dragged over places that made her sob. He fucked her like that—relentless, eyes locked on the lewd sight of her asshole swallowing him—while she screamed how much she loved being split open on him, how she’d never let anyone else near it, how she was still his dirty holiday whore who needed cum pumped deep.

“Going to fill this hole,” he gritted, pace turning savage, hips jackhammering. “Going to pump you so full it leaks down your thighs under the Christmas lights. Take it—take every drop like the anal slut you are.”

She came first, hard and shaking, cunt gushing around nothing while her ass clenched rhythmically on his cock. The tight milking pulled him over. Emmett buried himself to the hilt with a guttural shout and unloaded—thick hot ropes of cum flooding her guts, pulse after pulse, so much she felt it start to overflow around his shaft even before he finished throbbing. He stayed buried, grinding, forcing every spurt deeper while she trembled and whimpered through the aftershocks.

When he finally eased out, a heavy glop of cum followed, dripping white down her parted cheeks and onto the stone. Her hole stayed open, fluttering, leaking. He rubbed the head of his still-hard cock through the mess, smearing it, pushing some back inside with two fingers.

Hana hung over the rack, wrecked and glowing, dress still bunched, ass red and used. Voices floated faintly from the house again—laughter, a door slamming. Emmett’s hand stroked possessively over her ruined hole, scooping more cum and feeding it back in.

“We’re not finished,” he said low against her ear, even as he helped ease her legs down. “Not by a long shot. You’re walking back up there with my load plugged deep in your ass, and after they all pass out on mulled wine I’m bringing you right back down here. Or dragging you to your room. I want you again before sunrise—want to watch you sit on it slow this time, want to hear you beg for a second round while you’re still dripping the first. Holiday’s not over, Hana. Neither are we.”

She straightened on unsteady legs, feeling the warm trickle already starting down her inner thigh, and met his eyes with a filthy, hungry smile that promised she wasn’t close to done either.

She didn’t make him wait. The second the house went quiet—chairs scraping, footsteps fading up the stairs, the last clink of glasses dying into Christmas silence—Hana pushed the cellar door shut with her heel and locked it. Emmett was already waiting by the barrels, cock half-hard and still shiny with the mess he’d pumped into her less than an hour ago. She walked straight to him, dress still clinging to the sticky insides of her thighs, and shoved him back against the cool stone wall.

“You said not finished,” she whispered, voice raw from screaming. “So finish me proper this time. Holiday’s almost over. Make the last one count.”

His hands were on her before she finished the sentence—yanking the dress up, spinning her, bending her hard over the nearest crate so her ass lifted high and open. Cum still leaked from her used hole in slow white drips; he scooped it with two fingers and pushed it back inside, twisting deep until she moaned and pushed back for more.

“Still full of me,” he growled. “Still fucking dripping. Look at this greedy little asshole—can’t even hold a load without begging for another.”

“Then give it another,” she panted. “Stretch me raw. I want to feel you when I sit on the plane tomorrow. Want to clench and remember how deep you went.”

Emmett spat thickly onto her rim, rubbed it in with the head of his cock, and shoved in one brutal stroke. Her hole was already soft and sloppy from the first round; it stretched wet and easy around him, taking every fat inch until his balls slapped her cunt. She cried out into the wood, the sound filthy and broken, and he started fucking her like he meant to leave bruises.

Hard. Deep. No mercy. His hips cracked against her reddened cheeks, the wet filthy slap of skin echoing off the racks. Every thrust forced more of his earlier cum out around his shaft in lewd white froth that smeared her thighs and dripped to the stone. He fisted her hair, yanked her head back, and reached around to pinch her clit mercilessly while he pounded her ass.

“That’s it—take it like the holiday anal slut you are. Listen to that hole squelching. So fucking wrecked already and still sucking me deeper. Tell me how much you needed this last one.”

“Needed it—fuck—needed your cock splitting me open one more time,” she sobbed, pushing back to meet every brutal stroke. “Needed you to use my ass until it’s gaping and full and ruined. Please, Emmett—harder—fill me again—make it leak down my legs while I pretend we’re just friends upstairs—”

He snarled and changed the angle, one boot kicking her feet wider, folding her tighter over the crate so he could drive straight down into her guts. The new depth made her vision spark white. She came hard and sudden, cunt pulsing empty while her ass clamped like a fist around him, milking, fluttering, trying to drag the cum out of his balls. He didn’t stop. He fucked her straight through it, relentless, until she was babbling nonsense and her legs shook.

“One more,” he gritted. “Gonna pump you so full you’ll taste it. Keep that hole open. Don’t you dare clench shut when I pull out—I want to watch it gape and drip.”

He slammed home three more vicious times, buried to the root, and unloaded with a guttural groan. Hot thick ropes flooded her already-stuffed ass, pulse after heavy pulse, so much it forced earlier cum out around his cock in messy spurts. He ground deep, forcing every drop inside, hips jerking until he was spent and panting against her back.

When he finally eased out, her hole stayed open—pink, puffy, ruined—leaking a thick white river down her taint and over her swollen cunt lips. Emmett rubbed the head of his spent cock through the mess, smearing it, pushing some back in with his thumb while she trembled and whimpered.

Hana slid off the crate on jelly legs, turned, and dropped straight to her knees on the cold stone. She didn’t ask. She just opened her mouth, took his glistening, half-hard cock onto her tongue, and sucked it clean. Slow. Filthy. Looking up at him the whole time with pure filthy satisfaction while she licked every trace of her own ass juices and their mixed cum off his shaft and balls. She hollowed her cheeks, tongue swirling under the head, tasting salt and musk and the sharp tang of her own hole, and didn’t stop until he was shiny-clean and twitching again in her mouth.

She pulled off with a wet pop, kissed the tip once, and whispered up at him, voice hoarse and smug.

“Perfect way to end our holiday fling.”

Then she stood, straightened her dress with deliberate care, smoothed the fabric down over her sticky thighs and still-leaking ass. She grabbed the dusty bottle of reserve she’d originally come for, turned back, and gave his cock one last slow, teasing squeeze—fingers tight, thumb rubbing the sensitive head until he hissed.

She sauntered out of the cellar without looking back, hips swaying, the door swinging shut behind her, leaving him aching and hard again in the dark among the barrels.

Next Christmas couldn’t come fucking soon enough.