Cheating

The Groom's Best Man's Cabin Weekend Betrayal

Best man barebacks his best friend's fiancée all weekend at the cabin.

9 min read 2,048 words June 29, 2026New

The engine of my truck growled to a stop in front of the sprawling lakeside cabin, tires crunching over the gravel drive that wound through thick pines. The air smelled of pine needles, sun-warmed wood, and the faint metallic tang of the lake beyond the trees. I killed the ignition and glanced over at Chloe in the passenger seat. Twenty-four, sun-kissed, and wearing a thin white sundress that clung to her full breasts and the smooth curve of her hips like it had been painted on. Her long chestnut hair spilled over one shoulder, and those hazel eyes flicked toward me with the same electric awareness I’d felt since the moment she climbed into my truck yesterday morning.

The other two groomsmen, Jake and Tyler, were already stumbling out of the back seat, laughing too loud and cracking open fresh beers even though it was barely noon. My best friend, Ryan, was still stuck in the city finishing up a work emergency. He wouldn’t make it until tomorrow night. That left me—the best man—in charge of the cabin, the boats, the whiskey, and, apparently, his fiancée for the next thirty-six hours.

Chloe stepped out of the truck and stretched, the hem of her dress riding high enough to show the soft underside of her ass. My cock twitched at the sight. We had history. Five years ago, at a mutual friend’s house party, we’d gotten wasted, ended up alone on a balcony, and spent three hours trading filthy whispers and almost-kisses. My hands had been under her shirt, her fingers stroking me through my jeans, when someone had come looking for us. We never spoke of it again. Two years later she met Ryan. Now she was wearing his ring.

She caught me staring and didn’t look away. A slow, guilty smile curved her lips before she turned and followed the guys inside.

The afternoon passed in a haze of beer, grilling steaks, and loud music. The sun dipped low, painting the lake in molten gold. Jake and Tyler were already sloppy by eight, pounding shots and telling the same stories they always told. By ten they were both face-down on the oversized sectional in the living room, snoring like bears. The cabin fell into that deep, echoing quiet that only exists this far from the city.

Chloe found me on the back deck. She had changed into tiny denim cutoffs and one of Ryan’s old college hoodies that hung off one shoulder, exposing the delicate strap of her pink bra. Her feet were bare, toenails painted a soft coral. She carried two glasses and a fresh bottle of rye.

“Thought you might want company,” she said, voice low and a little husky. “They’re out cold.”

I took the glass she offered. Our fingers brushed. That single touch sent a bolt straight to my groin.

We walked down the wooden path to the private dock that jutted out over the black water. The night was warm, the sky thick with stars. Crickets and frogs made a low, pulsing chorus. Chloe sat at the edge, legs dangling, and I settled beside her. The whiskey burned sweet down my throat.

For a while we just drank in silence. Then she spoke.

“I almost didn’t come this weekend.”

I glanced over. “Why?”

She stared out at the lake. “Cold feet. Big, ugly, screaming cold feet.” A shaky laugh escaped her. “Ryan’s been working late every night for months. When he is home he’s on his phone or too tired to even kiss me properly. I keep thinking… is this what the rest of my life is going to feel like?”

My pulse hammered. I took another swallow. “You love him though, right?”

“I do,” she whispered. Then, softer, “But I’ve never stopped wondering.”

“Wondering what?”

She turned those hazel eyes on me, and the air between us suddenly felt too thin. “What it would’ve been like if we hadn’t stopped that night on the balcony. What it would feel like to have you inside me. I’ve thought about it when I’m touching myself. I’ve thought about it when Ryan’s on top of me and I can’t come.”

The confession hit me like a freight train. My cock surged to full hardness so fast it ached. I set my glass down with a soft clink.

“Chloe…”

“I know,” she breathed, cheeks flushed. “I’m a terrible person. But I’m getting married in three weeks and I’m so fucking scared I’m making a mistake. And the only thing that makes me feel alive right now is the way you’ve been looking at me since we got here.”

I reached out, slow enough that she could pull away. My fingers slid into her hair, cupping the back of her head. She shivered.

“Tell me what you want,” I said, voice rough.

Her lips parted. “I want you to fuck me. Bare. I want to feel all of you. No condom. No regrets tonight. Just… give me something I’ll remember when I’m walking down the aisle.”

The last thread of my restraint snapped.

I pulled her into a kiss that had been five years in the making. It wasn’t gentle. It was teeth and tongues and years of swallowed hunger. She moaned into my mouth, climbing into my lap on the dock, grinding her denim-covered pussy against the thick ridge of my cock. Her hands fisted in my shirt. Mine slid under the hoodie, palming her heavy tits, thumbs circling her hard nipples until she whimpered.

We barely made it back to the cabin.

The moment the door shut behind us I had her hoodie off, her shorts yanked down her long legs. She stood in nothing but that pink bra and a tiny matching thong already soaked at the crotch. I stripped fast, kicking my jeans aside. My cock sprang free, thick, veined, and leaking at the tip. Chloe’s eyes widened with raw want.

“Jesus,” she whispered. “It’s bigger than I imagined.”

I sat on the big leather couch in the center of the living room and crooked a finger. “Come here. Show me how bad you’ve wanted this.”

Chloe didn’t hesitate. She straddled me reverse cowgirl, facing away, and reached back to pull her thong to the side. The sight of her glistening pink pussy hovering over my bare cock was obscene. She lowered herself slowly, inch by thick inch, until her ass met my thighs and every centimeter of me was buried in tight, molten heat.

“Fuck,” she gasped, head falling back. “You’re so deep. I can feel you in my stomach.”

She started to ride. Slow at first, rolling her hips in filthy circles, grinding her clit against the base of my shaft. The wet sounds of her pussy sucking on my cock filled the cabin. I watched her perfect ass bounce, the tight pink ring of her asshole winking every time she bottomed out. I brought my hand down hard on one cheek. The slap cracked through the room. Chloe cried out, clenching around me.

“Again,” she begged. “Harder.”

I spanked her again and again, turning her ass a glowing pink while she rode me faster, her juices dripping down my balls. I fisted her long hair and yanked her head back, arching her spine.

“Ride that dick like you’ve been dreaming about it,” I growled.

“I have,” she moaned. “God, I have. Every time he fucked me I closed my eyes and pretended it was you.”

Her words sent a spike of dark pleasure through me. I thrust up to meet her, pounding into her from below. The couch creaked violently. Her tits bounced inside the pink bra until I reached around and yanked the cups down, freeing them so I could pinch and tug her nipples.

She came suddenly, violently, pussy spasming around my bare cock like a vice. Her cries echoed off the rafters. I didn’t stop. I kept driving up into her through her orgasm until her legs shook.

I needed more.

I lifted her off me, spun her around, and bent her over the wide arm of the couch. Her ass was up, back arched, pussy swollen and dripping. I slammed back inside her in one brutal thrust. Chloe screamed my name—my name, not Ryan’s—loud enough that I clamped a hand over her mouth.

“Quiet, baby. You want them to wake up and see you getting railed by the best man?”

She shook her head, but her pussy clenched harder at the words. I fucked her mercilessly, hips slapping against her reddened ass, balls smacking her clit with every stroke. I kept one hand twisted in her hair, the other gripping her hip hard enough to leave marks. The couch arm bit into her pelvis. She pushed back to meet every thrust, greedy for more.

“Say it again,” I demanded.

“I’m yours,” she gasped against my palm. “This pussy is yours. Fuck me harder than he ever could.”

I gave her exactly what she asked for. The wet slap of skin on skin, her desperate moans, the obscene squelch of her soaked cunt—it all blended into a filthy symphony. I felt my balls drawing up, the pressure building at the base of my spine.

I pulled out, flipped her onto her back on the couch, and shoved her legs wide. Her eyes were glassy with lust, lips swollen, mascara smudged. She locked her ankles behind my back as I sank back into her.

“Look at me,” I ordered.

Our eyes locked. I fucked her with long, deep strokes, grinding against her clit on every thrust. Her nails raked down my back. Her mouth fell open in a silent cry.

“Come inside me,” she whispered. “Please. Fill me up. I want to feel it leaking out of me all weekend.”

That was it. I buried myself to the hilt and came with a guttural groan, pumping thick ropes of cum deep into her married-to-be womb. Pulse after pulse, more than I thought I had in me. Chloe came again at the feel of it, her walls milking every drop from my cock, her legs trembling around me.

We stayed locked together, panting, sweat-slick, my cock still twitching inside her as the last of my load oozed around the seal of her pussy.

Finally I pulled out. A thick glob of my cum immediately dribbled from her well-fucked hole onto the leather cushion. Chloe stared at it with a dazed, satisfied smile.

We cleaned up in frantic silence—wiping the couch, showering separately, straightening clothes. By the time Jake and Tyler started groaning and shifting on the sectional an hour later, we were both dressed and pretending to scroll on our phones at the kitchen island like nothing had happened.

The rest of the weekend was exquisite torture.

Chloe wore Ryan’s ring on her left hand and my bite marks hidden under her clothes. Every time our eyes met across the campfire or the breakfast table, heat flared between us. She kept stealing guilty glances at me while laughing at Ryan’s jokes once he finally arrived. Under the dinner table Saturday night her bare foot slid up my calf while she texted me one-handed.

Need you again. Tonight. Cabin loft. I’ll leave the door unlocked. I can still feel your cum inside me.

I didn’t answer the text. I just looked up and held her gaze until her cheeks flushed crimson.

She had no idea I’d forgotten to lock the bedroom door when I left her that second time, deep in the night, after I’d fucked her twice more in the loft—once with her face pressed into a pillow to stifle her screams, and once with her riding me slow and tender while we both pretended this could stay a secret forever.

She also didn’t know that Ryan had come back from the city six hours earlier than he’d told everyone.

He’d seen my truck. He’d heard the sounds from the loft. And instead of storming in, he’d stood in the shadows of the hallway for twenty full minutes, cock in his hand, watching his best friend bareback his future wife until I filled her for the third time that weekend.

Some secrets, it turns out, aren’t just between two people.

And the wedding was still two weeks away.

Tagged cheating dirty-talk fingering almost-kiss breast-groping

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