Holiday Fling Takes It Up the Ass

The salt-kissed breeze rolled off the Mediterranean and tugged at the hem of Rachel’s white crochet cover-up as she approached the tiki bar. At twenty-eight, the London marketing executive had flown to Ibiza alone for one reason: to forget the stale, predictable fucks that had defined the last two years with her ex. No more polite missionary. No more “was that good for you?” She wanted to feel used, claimed, filthy. And right now, every cell in her body was screaming that she might have found the man who could deliver it.

The bar was a palm-fronded temple of rum and sin, half-empty in the lull between sunset and the midnight rush. Behind the scarred wooden counter stood Felix. Thirty-two, rugged Australian bartender with sun-bleached streaks in his dark hair, a jaw like chipped granite, and shoulders that stretched the black tank top he wore like it was considering surrender. A faded tattoo of a compass rose disappeared beneath the fabric at his collarbone. His forearms were thick, veined, dusted with sand and salt. He looked like he could throw a woman over one of those shoulders and carry her off without breaking stride.

Rachel slid onto a bamboo stool, letting the cover-up ride up her thighs. She felt his eyes immediately—hot, unapologetic, dragging from her tits down to the generous curve of her ass as she settled. When his gaze lingered there, blatantly, a slow smirk tugged at the corner of his mouth.

“What’s a woman with an ass like that drinking tonight?” His voice was gravel wrapped in a lazy Australian drawl.

Rachel crossed her legs, letting the movement pull the fabric tighter across her backside. She met his stare head-on, pulse already kicking between her thighs. “Something strong enough to make me forget I ever played it safe. And maybe something that makes you keep looking at my ass like you want to bury your face in it.”

Felix’s laugh was low, dirty. He leaned both forearms on the bar, bringing his face closer. Blue-green eyes locked on hers with zero shame. “Been staring since you walked up. That thing’s a fucking crime in those bikini bottoms. Round, tight, made for a man to spread open and ruin. You gonna let me keep looking, Rachel?”

She hadn’t given him her name yet. The fact that he’d read it off the credit card she’d tossed on the bar without her noticing only made her pussy clench harder. “Depends. You gonna keep eye-fucking me like you’re already imagining how my asshole’s gonna feel squeezing your cock?”

The words left her mouth before she could filter them, raw and honest. Felix’s nostrils flared. A visible twitch rolled through his jaw. He didn’t blink.

“Careful, love. I’ve got three hours left on this shift and a private beach hut fifty metres down the sand. Keep talking like that and I’ll be serving drinks with a hard-on so obvious the whole bar will know I’m thinking about stretching that pretty little hole.”

Rachel’s breath hitched. Heat flooded her cheeks, her chest, the slick seam of her cunt. She shifted on the stool, deliberately arching her back so her ass lifted slightly off the seat. “Maybe that’s exactly what I came here for. A stranger who doesn’t ask permission with flowers and bullshit. A man who sees what he wants and takes it.”

Felix poured her a rum punch without looking away, sliding it across the bar. His fingers brushed hers—calloused, hot. The touch lingered.

“Keep teasing me, Rachel, and I won’t just take it. I’ll fuck that tight ass raw. No rubber. No gentle. Just my thick cock splitting you open until you’re drooling into the sheets and begging me to fill your guts with cum.”

Her interior muscles fluttered at the image. She had never let anyone fuck her ass. Her ex had hinted once; she’d shut it down. Now the mere suggestion from this bartender had her clenching involuntarily, a dark, hungry thrill uncoiling low in her belly.

She took a slow sip, letting the rum burn down her throat. “You talk a big game for someone still stuck behind a bar.”

Felix’s grin turned predatory. “Shift ends at ten. My hut’s got a king bed, cold beer, and zero neighbours. You show up, we stop pretending. I tell you exactly how I’m going to wreck that ass. You tell me how bad you’ve been dying to give it to a stranger who won’t be gentle. Then we find out if your tight little hole can take every inch I’ve got.”

Rachel’s nipples were stiff peaks against her bikini top. She could feel how wet she already was, the fabric between her legs soaked. “I’ll be there.”

The next three hours were exquisite torture.

Felix kept working, but his eyes never left her for long. Every time she stood up to stretch, to walk to the water’s edge and back, she felt his stare burning into her ass like a brand. Once, while mixing a cocktail for a group of tourists, he openly adjusted the thick ridge of his erection through his shorts while looking straight at her. No apology. Just raw hunger.

Rachel’s mind spun. I’m really going to do this. I’m going to let a thirty-two-year-old Australian bartender I met three hours ago fuck my ass with no condom and no limits. The thought should have terrified her. Instead it made her ache so badly she had to press her thighs together on the stool.

At ten sharp, Felix slapped the counter with a towel, told the other barman he was done, and crooked a finger at her. Rachel’s legs felt shaky as she followed him down the moonlit path behind the bar. His hut was small, private, half-hidden by palm trees and lit by a single string of fairy lights. Inside it smelled of cedar, salt, and man.

Felix closed the door behind them, flipped the lock, and immediately crowded her against the wall. Not touching her yet—just close enough that she could feel the heat rolling off his body and smell the faint coconut oil on his skin.

“Before anything happens,” he said, voice rough, “I need to hear it from your mouth. I’ve been hard as fuck for hours thinking about bending you over and forcing every inch of my cock up that virgin ass. No lube except spit and precum. No tapping out. I want to hear you moan like a slut while I wreck you. Tell me that’s what you want, Rachel. Tell me you’ve been fantasising about exactly that.”

Her heart hammered against her ribs. She looked up into his rugged face, at the raw lust in his eyes, and felt something inside her snap free.

“I have,” she whispered, then louder, braver. “I’ve touched myself for months thinking about a stranger like you. Someone who doesn’t care about being nice. I want you to take my ass raw, Felix. I want to feel you throb inside me, stretching me open, using me until I can’t sit down tomorrow. No limits. No safe words unless I scream red. I want to give my tight little asshole to you completely.”

Felix groaned, deep in his chest, and finally touched her—large hands gripping her waist, sliding down to palm the generous globes of her ass and squeeze hard. He yanked her against him so she could feel the massive, rigid length of his cock trapped between their bodies.

“Fuck, you’re perfect,” he growled against her ear. “Twenty-eight years old, marketing bitch from London, and you’re standing in my hut begging a bartender to sodomise you bare. I’m going to make you regret how badly you want this—in the best possible way.”

He walked her backwards toward the bed, hands never leaving her ass, kneading, spreading her cheeks through the thin fabric as they moved. Rachel’s breath came in short, excited gasps. She could already imagine the burn, the overwhelming fullness, the way his heavy balls would slap her dripping pussy while he reamed her asshole.

Felix stopped at the edge of the mattress and spun her around, bending her forward so her hands braced on the bed. He yanked the cover-up off her shoulders and let it drop. Then he hooked his fingers in the waistband of her bikini bottoms and peeled them down slowly, exposing her completely.

“Jesus Christ, look at that,” he breathed. One rough thumb traced down her crack, stopping just above her puckered hole. “So pink. So fucking tight. I’m going to spend the next hour opening this pretty asshole up with my tongue and fingers before I feed it every thick inch I’ve got. By the time I’m balls-deep, you’re going to be shaking and drooling and pushing back like the anal whore you were always meant to be.”

Rachel moaned, arching her back, offering herself. Her mind was a whirlwind of filthy anticipation—he’s really going to do it, he’s going to fuck my ass raw, no mercy, no condom, just pure, nasty, stranger anal—and the knowledge that they were only getting started sent a fresh gush of wetness down her thighs.

Felix dropped to his knees behind her, hands spreading her cheeks wide, hot breath ghosting over her most private hole. His voice was thick with lust.

“Last chance to back out, Rachel. Because once my tongue’s inside this ass, I’m not stopping until you’re gaping and dripping my spit and ready to take the roughest fuck of your life.”

She looked back over her shoulder, eyes glazed with pure need, and gave him the only answer she had left.

“Then stop talking and claim it.”

Felix’s hands tightened on her hips, but Rachel twisted before he could bury his tongue between her cheeks. She dropped to her knees on the rough wooden floor of the hut, the fairy lights casting warm gold across her bare skin. At twenty-eight she had never sucked a near-stranger’s cock with this kind of greedy urgency, but the ache in her untouched asshole had turned her into someone else—someone filthy, someone who needed to taste the man who was about to wreck her.

His shorts hit the floor. Felix’s cock sprang free, thick as her wrist, veined and heavy, the fat head already glistening with precum. Nine inches of raw Australian cock, curved slightly upward, balls hanging full and tight beneath. Rachel’s mouth watered. She wrapped both hands around the base and dragged her tongue up the underside in one long, sloppy lick.

“Fuck, that’s it,” Felix growled, voice gravel-rough. “Slobber on it, Rachel. Get it dripping for your tight little shithole.”

She did. Spit poured from her lips in thick strings as she worked him, sucking the head into her mouth with wet, obscene sounds. Her cheeks hollowed, throat opening as she forced more of him inside until her nose brushed the dark hair at his pelvis. Gagging, she pulled back, strings of saliva connecting her lips to his glistening shaft. She coughed, laughed breathlessly, then dove again, jerking the base with both fists while her tongue lashed the sensitive underside. The taste of salt, skin, and pure male made her pussy clench so hard she felt fresh slick slide down her inner thigh.

Felix’s hand fisted in her dark hair, not guiding, just holding on. “Look at you. Proper London marketing girl on her knees for a bartender’s cock. You’re going to take every inch of this up your arse, love. No mercy.”

Rachel moaned around him, the vibration making his thighs flex. She sucked harder, faster, until her chin was shiny with spit and his balls were soaked. Only when he was throbbing so violently she thought he might come down her throat did she pull off with a wet pop, strings of saliva breaking across her tits.

“Bed,” she gasped. “Now. I need it.”

She stood, turned, and bent over the king mattress, knees planted wide, back arched deep. Her round ass thrust up obscenely, the tight pink pucker winking in the low light. Felix knelt behind her instantly.

His hot breath ghosted over her hole first. Then his tongue—broad, wet, relentless—dragged from her dripping cunt all the way up to her asshole. Rachel cried out at the first firm lick. He ate her like a starving man, circling the tight ring, stabbing the tip of his tongue inside, groaning into her flesh. The wet, filthy sounds filled the hut. He spat directly on her hole, watched it drip, then pushed two thick fingers in without warning.

“Jesus, you’re tight,” he muttered, scissoring them, stretching the resistant muscle. “This arse has never been fucked, has it?”

“No,” she whimpered, pushing back onto his hand. The burn was sharp, perfect. Every thrust of his fingers sent sparks up her spine. “Never. I saved it… fuck, I saved it for this. For a dirty stranger like you.”

He added a third finger, pumping harder, his tongue still flicking around the stretched rim. Rachel’s legs shook. Her interior muscles fluttered wildly, caught between pleasure and the overwhelming pressure. She reached back, spreading her own cheeks wider, silently begging for more.

Felix stood. The blunt head of his cock nudged her spit-slick hole. “Beg.”

“Fuck my ass,” she moaned immediately. “Please, Felix. Slam it in. Ruin me.”

He did.

One brutal thrust and the fat crown popped past her ring. Rachel’s mouth fell open in a silent scream as six thick inches speared into her virgin channel. The stretch was ferocious, a white-hot ache that made her eyes water and her pussy gush. Felix didn’t pause. He gripped her hips and drove the rest of his length home until his heavy balls slapped her clit.

“Fuuuuck,” he snarled. “So goddamn tight. Like a velvet vice around my cock.”

He started pounding. Hard. The wet slap of flesh on flesh echoed off the cedar walls. Each thrust forced her forward on the bed, her tits dragging across the sheets. The burn melted into a deep, dirty fullness that made her see stars.

“Deeper!” she cried, voice breaking. “Harder, Felix—god, wreck my asshole! Make it gape!”

He gave her exactly what she begged for. His hips became a piston, slamming into her so hard her feet left the floor. One hand cracked across her ass cheek, leaving a red print. Rachel pushed back to meet every stroke, drooling onto the mattress, lost in the filthiest pleasure she had ever known. Her marketing brain had gone quiet; only the animal remained—ass up, begging a bartender to sodomise her raw.

“Switch,” he growled suddenly, pulling out with a filthy pop. His cock glistened with her spit and ass juice. “On top. I want to watch you impale yourself.”

Rachel’s legs barely worked, but she shoved him onto his back and climbed over him. She straddled his hips in reverse cowgirl first, then spun so they could see each other. Grabbing his slick cock, she lined it up with her wrecked hole and sank down in one aggressive motion.

“Fuck yes,” she hissed as he filled her again. The new angle made him feel even bigger. She planted her hands on his chest and started riding—hard, fast, filthy bounces that made her ass ripple. Every downward slam took him balls-deep. Her tits bounced wildly; Felix reached up and pinched her nipples until she cried out.

“That’s it, ride it, you anal whore,” he snarled, Australian accent thicker with lust. “Use my cock to stretch that greedy hole.”

Rachel rode like she was possessed, grinding in tight circles, then lifting until only the head remained inside before slamming back down. Sweat slicked their bodies. The hut smelled of sex and salt air. She could feel her asshole loosening, opening, taking him easier with every aggressive bounce. The pressure on her g-spot from the inside was unbearable; she came suddenly, violently, ass clenching around his thickness so hard Felix swore.

He flipped her onto her back without pulling out. In missionary he hooked her legs over his shoulders and folded her in half, pinning her knees beside her ears. The position let him look straight down at where they were joined. Rachel stared too, mesmerised by the sight of his thick cock spearing in and out of her once-tiny hole. It gaped obscenely around him now, red and puffy, her inner walls clinging to every vein.

“Look at that pretty arsehole,” Felix panted, slowing just enough for her to see how stretched she was. “Fucking ruined. My cock’s reshaped you, Rachel.”

“Cum in it,” she begged, voice hoarse. “Fill my guts. I want to feel you pumping deep.”

His thrusts turned savage. The bed creaked dangerously. Rachel’s fingers found her clit and rubbed frantically. When his rhythm stuttered and his balls drew up tight, she knew he was close.

With a guttural roar Felix buried himself to the hilt and came. Thick, hot ropes of cum erupted straight into her bowels. Pulse after pulse, so much it felt like he was flooding her. Rachel came again from the sheer filthy knowledge of it, her asshole milking every drop.

He stayed buried until the last spasm faded, then slowly pulled out. The moment his cock left her, a thick glob of white cum bubbled from her gaping hole and slid down toward her pussy. Rachel reached back with two fingers, scooped it up, and pushed it back inside her wrecked ass with a wicked, sated grin.

“Mine now,” she whispered, eyes locked on his.

Felix leaned down, sweat dripping from his brow, lips parted for the kiss they both needed.

A sharp, frantic knock rattled the hut door.

“Felix! Open up, mate—it’s urgent! The cops are here looking for that British girl who was at your bar all night. Someone reported her missing!”

They froze, his cum still leaking from her stretched asshole, her fingers buried inside it, hearts hammering as the knocking grew louder.