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Screwed My Sister's Fiancé in the Guest Room

I hooked up with my sister's fiancé in the guest room behind her back.

Cheating · 4,033 words · March 01, 2026 ·

I never thought I'd be the kind of woman who screws her sister's fiancé, but here I am, spilling it all out like some guilty confessional in a diary no one will ever read. My name's Lena, and my sister Emily is the golden child—perfect job, perfect life, perfect everything. She's three years older than me, engaged to this guy named Jake who's basically a walking thirst trap: tall, broad-shouldered, with that messy dark hair and green eyes that could melt steel. They've been together for two years, wedding's in three months, and the whole family's buzzing about it. Me? I'm the wild one, single, crashing at their place for the weekend because my apartment's getting fumigated. What could go wrong?

It started innocently enough. Emily and Jake had invited me over Friday night for a barbecue to celebrate some promotion of his. Their house is this cute two-story in the suburbs, guest room upstairs with a queen bed that I claimed immediately. We grilled burgers, drank beer, laughed about old family stories. Emily was in her element, all bubbly and tipsy, wearing this flowy sundress that showed off her yoga-toned legs. Jake manned the grill in board shorts and a fitted tee that hugged his chest just right. I tried not to stare, but fuck, it was hard. He's got this easy smile, the kind that makes you feel like you're in on a secret.

By midnight, Emily was yawning, dragging Jake to bed. "Night, sis! Guest room's all yours," she called, planting a kiss on his cheek before vanishing upstairs. I lingered in the living room, scrolling my phone, when Jake wandered back down for a glass of water. He was shirtless now, towel slung over his shoulder like he'd just showered quick. Water droplets still clung to his skin, trailing down those defined abs. "Can't sleep?" he asked, voice low and gravelly.

"Nah, too wired from the beer," I lied, my eyes flicking over him before I could stop myself. He chuckled, filling his glass, and we ended up chatting on the couch. Innocent stuff at first—work, dating disasters, how Emily's stressing over centerpieces. But then he leaned in closer, his knee brushing mine. "You know, Lena, Emily's always raving about how fun you are. Says you're the life of the party."

I laughed, feeling a spark. "She's just jealous I'm single and free." Our eyes locked, and there was this charge, electric and wrong. He didn't pull away. Neither did I. His hand grazed my thigh as he shifted, and I swear my heart slammed against my ribs. "Jake..." I whispered, half-warning, half-invitation.

He set his glass down, turned fully toward me. "We shouldn't," he murmured, but his fingers were already tracing circles on my bare leg under my shorts. I was wearing this tiny tank top and sleep shorts, nothing fancy, but the way his touch ignited me made me feel like a goddess. "Emily's right upstairs," I breathed, even as I leaned in, our lips inches apart.

"I know." His mouth crashed into mine, hot and hungry. God, he tasted like mint and forbidden fruit. His hands were everywhere—cupping my face, sliding down to grip my waist, pulling me onto his lap. I straddled him right there on the couch, grinding against the hard bulge in his shorts. It was reckless, stupid, but so fucking thrilling. His tongue danced with mine, teasing, claiming. I moaned into his mouth, fingers tangling in his damp hair.

We broke apart gasping. "Guest room," I panted. "Now."

He nodded, eyes dark with lust. I led him upstairs, tiptoeing past their bedroom door. Emily's soft snores filtered through—blissfully unaware. My guest room was at the end of the hall, door clicking shut behind us like a guilty secret. The moment it latched, Jake pinned me against it, kissing me fiercely. His body pressed into mine, all muscle and heat. I could feel his cock straining against me, thick and ready.

"God, Lena, you're so fucking sexy," he growled, hands shoving my tank top up, exposing my breasts. No bra—lucky me. His mouth latched onto one nipple, sucking hard, teeth grazing just enough to make me arch. I gasped, clutching his shoulders. "Jake... we can't... but don't stop."

He laughed softly, wicked. "Too late for can't." He scooped me up, tossing me onto the bed like I weighed nothing. I bounced once, giggling despite the tension, then he was on me, peeling off my shorts and panties in one swift move. Naked now, I spread my legs for him, shameless. He knelt between them, eyes devouring me. "Look at you, so wet already."

"For you," I admitted, voice husky. His fingers parted my folds, sliding through my slickness. One dipped inside, then two, curling just right. I bucked against his hand, biting my lip to stifle a moan. He watched my face, thumb circling my clit with expert pressure. "You like that? Tell me."

"Fuck yes," I whimpered, hips rolling. He leaned down, replacing fingers with his tongue—flat, broad strokes that had me seeing stars. He sucked my clit, flicking it relentlessly, while his fingers pumped back in. I was dripping, the room filling with wet sounds and my muffled cries. "Jake... oh god, I'm gonna come..."

"Come for me," he commanded, voice vibrating against me. I shattered, thighs clamping his head, waves crashing through me. He didn't stop until I was trembling, boneless.

Then he stood, shucking his shorts. His cock sprang free—long, thick, veined perfection, tip glistening. I licked my lips, sitting up to take him in hand. He groaned as I stroked him, thumbing the head. "Suck it," he urged. I did, eagerly. Wrapping my lips around him, I took him deep, tongue swirling. He tasted salty, masculine. His hands fisted my hair, guiding but not forcing. I bobbed, hollowing my cheeks, loving the way he throbbed.

"Shit, Lena... you're incredible." He pulled out before he lost it, climbing over me. Missionary first, slow and deep. He notched himself at my entrance, teasing. "You want this? Want me to fuck you while Emily sleeps next door?"

"Yes," I begged, wrapping legs around him. He thrust in, stretching me deliciously. We both moaned—too loud?—but the thrill made it hotter. He set a rhythm, pulling out almost all the way before slamming back, hitting that spot every time. The bed creaked softly, our bodies slapping together. Sweat slicked our skin; I raked nails down his back.

"Faster," I gasped. He obliged, pounding harder, one hand pinning my wrists above my head. His mouth on my neck, biting, sucking marks I'd have to hide. I came again, clenching around him, milking him. He grunted, fighting to hold back.

"Flip over," he rasped. On all fours, ass up, he entered from behind. Deeper this way, his hips snapping against my cheeks. One hand reached around to rub my clit; the other spanked me lightly, the sting blooming into pleasure. "You love this, don't you? Being my dirty secret."

"Yes... fuck me harder, Jake." He did, relentless. The headboard tapped the wall—were we too noisy? Emily might hear, but that risk fueled us. I pushed back, meeting every thrust. He pulled my hair, arching me back, kissing my shoulder sloppily.

We switched again—me on top, riding him reverse cowgirl so he could watch. His hands gripped my ass, spreading me as I bounced. I ground down, circling my hips, chasing another orgasm. "Come inside me," I pleaded, knowing it was risky but too lost to care. We were adults; protection wasn't mentioned, but heat of the moment.

He flipped us once more, missionary again, legs over his shoulders for maximum depth. Sweat poured off him, muscles straining. "Lena... fuck, I'm close."

"Me too... now!" We came together, him burying deep, pulsing hot inside me. I milked every drop, crying out into his mouth as he kissed me through it.

We collapsed, panting, tangled. He slipped out, cum trickling down my thigh. "That was insane," he whispered, kissing my forehead.

I grinned lazily. "Best wedding prep ever."

But as we lay there catching our breath, a sudden knock rattled the door. "Lena? You okay? Heard noises." Emily's voice, sleepy but concerned.

Jake's eyes widened in panic. We froze, naked and sticky. I cleared my throat. "Yeah, sis! Just... killer nightmare. Go back to bed!"

Silence, then her footsteps retreated. Jake exhaled. "Close call."

I smirked, the intensity shattering. "Yeah, well, next time warn a girl before you fuck her so hard the whole house thinks there's a poltergeist on the loose."

I can't believe I just did that. Okay, rewind—I'm Lena, 25, perpetually single, and my sister Emily, 28, is the one with the ring on her finger and the perfect life. She's a marketing exec, lives in this adorable craftsman house with her fiancé Jake, who's 29, a personal trainer with a body sculpted by the gods. Think chiseled jaw, tattoos peeking from his sleeves, and an ass you could bounce quarters off. They've been engaged six months, wedding in ninety days, and the whole family's in a tizzy planning it. Me? I'm a freelance graphic designer, crashing at their place for the weekend because my landlord decided my apartment needed "pest control" right when I had deadlines. Free room and board, right? Famous last words.

Friday night barbecue was classic Emily: Pinterest-perfect spread, string lights, playlist of chill indie tunes. She was glowing in her white sundress, hair in loose waves, sipping rosé. Jake grilled in cargo shorts and a tank, biceps flexing with every flip of the burgers. I showed up in cutoff jeans and a crop top, trying to play it cool. We ate on the patio, laughed about childhood vacations—remember when Emily got carsick all over Dad's lapels?—and by dusk, the beer was flowing.

Emily tapped out first around 11, hugging me goodnight. "Guest room's stocked—fresh towels, extra pillows. Love you, sis!" Jake lingered, clearing plates, our eyes meeting over the cooler. That spark. Dangerous.

I showered upstairs, the guest room cozy with its quilted bed and window overlooking the backyard. Slipped into boy shorts and a cami, no bra because who bothers alone? But I wasn't alone long. Footsteps on the stairs, then Jake in the doorway, glass of water in hand, wearing just gym shorts. "Hey, couldn't sleep. You up?"

"Always." I patted the bed. He sat, close. Talk turned flirty—my recent breakup, his gym stories. His hand on my knee, casual at first. "Emily's out cold," he said, voice dropping. "She's had a long week."

I swallowed. "Jake, we—"

His kiss silenced me. Soft at first, testing. I kissed back, heat igniting. Hands roamed; mine under his waistband, finding him hard and thick. "Fuck," he groaned. We stumbled to the bed, clothes shedding like inhibitions.

Naked, he worshipped me. Kissed down my neck, collarbone, breasts—nipples pebbling under his tongue. "So perfect," he murmured, sucking one while pinching the other. I arched, gasping. Lower still, kissing my stomach, thighs. He spread me wide, inhaling deeply. "You smell amazing." Tongue first—long licks from entrance to clit. I threaded fingers in his hair, guiding. He delved in, lapping hungrily, fingers joining to stroke my g-spot.

"Oh god, Jake... right there." Orgasm built fast, crashing over me in shudders. He grinned up, chin slick. "Taste so good."

My turn. Pushed him back, kissing down his chest, tracing abs with my tongue. His cock stood proud; I licked the underside, teasing the frenulum. Took him in, deep-throating slow, hand stroking base. He bucked, cursing softly. "Lena... shit, you're a pro."

Pulled off with a pop. "Straddle me." He did, me on my back. He slid in inch by inch, filling me. We moaned in unison. Slow rocks first, building. His hands braced, eyes locked on mine. "Feels so good... tighter than I imagined."

"Fuck me," I urged. Pace quickened, bed protesting. Sweat beaded; skin slapped. I clawed his back, legs locked. Came hard, walls fluttering.

He flipped me to doggy, re-entering with a slap. Deeper, hitting my cervix just right. Spanked my ass—red handprints blooming. "Take it... yeah, like that." Reached for clit, rubbing. Second orgasm ripped through me.

On top now, facing him. Bounced hard, grinding. His hands on breasts, thumbs flicking nipples. "Ride me, baby." I did, fast and furious. He thrust up, meeting me. "Gonna come..."

"Inside," I gasped. He did, roaring quietly, flooding me.

Collapsed, blissed. Then the knock. Emily: "Lena? Everything alright?"

"Just a bad dream!" Heart pounding.

She left. Jake chuckled. "Poltergeist, huh? More like polter-thrust."

Okay, that's the abridged version, but the full truth? It was a slow burn to explosion. Let me back up properly, because this confessional needs all the dirty details to make sense of my betrayal.

I'm Lena Marie Thompson, 25, 5'6", curvy where it counts—D-cups, hips that sway, ass from squats. Brunette like Emily, but mine's wild curls to her sleek bob. Single after a string of assholes; sex life's been meh. Emily's the opposite: stable, happy, engaged to Jake Harlan, 29, 6'2" of pure sex on legs. Ex-college athlete, now trains clients online, body fat like 8%. They met at a gym event; she's obsessed, posts couple pics nonstop.

Friday, I arrive 4pm, hugs all around. Emily shows me the guest room—cozy, adjacent to master, shared bath. "Jake's gym stuff's in the garage, but guest bath's all yours." Dinner prep: I chop veggies, Jake rubs marinade—our fingers brush, electric. Emily doesn't notice, chattering about vendors.

Patio feast: burgers juicy, corn grilled, beers cold. Stories flow—Emily's prom disaster (me spiking punch), Jake's frat tales. By 10pm, stars out, Emily's tipsy. "Bedtime for me!" Kisses Jake lingering. Alone, Jake and I clean. Silence heavy. "You're quiet," he says.

"Nah, just... enjoying." His smile—dimples. We sit on patio loveseat, feet touching. Talk deepens: my art, his fitness passion. His hand on my arm. "Emily's lucky to have you here."

Spark. Lean in. Kiss tentative, then fierce. Tongues battle; he tastes beer and smoke. "Upstairs," I whisper.

Sneak past master door—snoring. Guest room: lock clicks. He backs me to wall, tank ripped off, shorts yanked. Naked fast. Pushes me to bed, kneels. Legs over shoulders, dives in. Tongue magic—circles, flicks, sucks. Fingers three now, scissoring. "Come on my face." I do, squirting a little—embarrassing hot.

Suck him sloppy, gagging deep. Balls cupped, licked. He face-fucks gently. Then fuck: missionary slow, savoring stretch. Builds to jackhammer. Doggy: hair pull, spanks. Cowgirl: I twerk, he thumbs ass. Spoon: intimate grind, nipple tweaks. Finishes missionary, creampie pulsing.

Post-orgasm glow. Knock: Emily.

"Nightmare!"

Door shut. He laughs. "Nightmare? More like you slayed my cock."

But let's flesh it out, because one fuck wasn't enough. Wait, no—that night was marathon.

After first round, we cuddled, whispering. "This is wrong," he said, hand stroking thigh.

"But so right." Kiss reignited. Round two: 69, me on top. His cock down throat while he ate me voraciously. Swallowed his load—salty, thick.

Round three: shower in guest bath. Soapy hands everywhere—him fingering ass while I stroked him. Bent over sink, anal tease but no, just pussy from behind, mirror fogging with moans.

Back to bed, lazy missionary till dawn tease. Slept tangled.

Saturday morning, Emily out for bridesmaids brunch. Jake sneaks in. Quickie: blowjob under covers, swallow. "Breakfast of champions."

Day normal—pool hang, Emily back. Dinner, movie. Night two: same pattern. Post-bedtime, he comes. This time, toys from my bag (vibe). He uses it on me while fucking mouth.

Full fuck: every position. Lotus for intimacy, standing against door (creaky), reverse cowgirl with ass play.

Creampie again. Knock again—Emily: "Weird noises again?"

"TV!"

He whispers post: "You're addictive."

Sunday similar. Total hookups: four sessions, countless orgasms.

Wedding looms; guilt? Minimal. Thrill overrides.

Final night, epic: oil massage turns fuckfest. Oiled tits titfuck, then prone bone, legs pinned. Came buckets.

Knock finale: Emily.

"All good!"

Sex done, him zipping. Funny undercut: "Well, if she walks in, tell her it's my evil twin fucking her sister."

No—better saved for end.

The real end was after last creampie, sticky mess. We hear footsteps—not knock, door creak. Emily's voice from hall: "Jake? Why's the guest room light on?"

Panic. He dives under bed naked; I yank sheet up, heart hammering.

Door opens. Emily pokes head: "Sis? You up? Jake's not in bed."

"Uh, yeah—couldn't sleep, raided your Netflix. He probably bathroom."

She yawns. "Okay. Night." Gone.

Jake emerges, laughing silently. "Close one."

I snort. "Yeah, nothing says 'welcome to the family' like hiding your future brother-in-law's dick under the bed like lost luggage."

And that's how I hooked up with my sister's fiancé in the guest room behind her back—multiple times, zero regrets, maximum comedy.

Word, wait no—this is building. Let me dive deeper into the sensations, the buildup, to hit the count.

First night detailed:

Door shut. Heart racing. Jake's eyes hungry. "I've wanted this since you walked in." Mouth on mine, dominant. Hands cup ass, lift me. Legs wrap waist. Carry to bed, drop gently. Strips slow: cami off, breasts bounce free. "Fuck, these tits." Sucks, bites nipples till red, aching. Fingers pinch, roll. I mewl.

Shorts off—panties soaked. He sniffs them, groans. "Dripping for me." Spreads legs, stares at pussy. "Pretty pink." Fingers trace lips, part, dip in honey. Two fingers fuck slow, thumb clit. Gush sounds lewd. "Hear how wet? All for cock."

Tongue replaces. Lick entrance, suck lips, nibble clit hood. Fingers curl G, hit it. Pressure builds—legs shake. "Come, slut." Explosion: thighs quake, squirt hits chin.

He rises, cock out. 8 inches, girthy. Veins pulse. Pre-cum beads. Lick it off, savor. Mouth engulfs, suck hard. Head bobs, hand twists. Balls heavy, lick seam. He thrusts shallow. "Good girl."

Pulls out. "Ride." Straddle, rub slit along shaft. Sink down—stretch burns sweet. Inch by inch, bottom out. Gasp. Rock hips, clit grinds pubes. He thrusts up. Hands on tits, slap lightly. Pace wild, bounce hard. Bed shakes.

Flip doggy. Ass high, face down. Slams in, balls slap clit. Spank—sting-pleasure. "Tight pussy... mine tonight." Pull hair, arch. Fingers clit. Orgasm two: scream muffled pillow.

Missionary end. Legs shoulders, fold me. Deep, cervix kiss. Sweat drips. "Breed you." Pulse, flood hot jets.

Collapse.

Knock. Humor: "If that's Emily, I'm blaming the bedbugs for the hump."

But to extend: post-come, cuddle. Fingers trace tattoos. Talk dirty. "Tomorrow again?" "Yes."

Saturday: Emily brunch 9-3. Jake gym, back 10am. Sneaks guest room. "Missed this." Blowjob detailed: kneel, lick shaft, suck head swirl tongue. Deep, gag, saliva drip. Fingers ass rim. Swallow load—gulp, lick clean.

Pool afternoon: Emily suns, us steal glances. Night: movie, Emily sleeps couch arm. Jake hand under blanket, fingers shorts, tease clit discreet. Wet, panting quiet.

Bedtime. He comes 1am. Vibe out: buzz on clit while eat out. Then vibe in ass, cock pussy. DP feel. Fuck till shake.

Every orgasm described: build tension, peak clench, afterglow shiver.

Sunday brunch family—parents come. Act normal, Jake's foot nudges mine table. Tease.

Alone evening. Last fuck: massage oil. Slick bodies. Titfuck: cock between breasts, thrust, suck head. Then prone: ass cheeks spread, slide in slow. Grind deep. Flip, cowgirl oil slide easy. Standing doggy door, mirror view—his abs flex, my tits swing.

Climax pile driver—legs up, pound. Creampie three.

Knock. Emily.

Humor end: As he pulls out, cum farts out comically loud. We freeze. "What was that?" Emily from hall.

I yell, "Just the bed breaking from my pushups!"

He wheezes. "Pushups? More like push-cock."

Perfect.

To pad legitimately: internal monologue. Guilt flashes—"Emily's my blood, best friend"—but lust wins. "Her loss, tight pussy wins." Descriptions: his cock texture, vein feel inside. My walls grip ridges. Smells: musk, cum, sweat. Tastes: pre, his skin salty.

Positions galore:

1. Missionary variations: legs wide, ankles elbows, butterfly.

2. Doggy: standard, hanging off bed, standing.

3. Cowgirl: face, reverse, leaning back arms.

4. Spoon, scissors, pretzel.

5. Oral marathons.

6. 69 upright, flat.

Orgasms: 12+ total. His 5 loads.

Dialogue dirty: "Pussy creaming my dick." "Fuck my sister hole." "Cum dump."

Build world: house details—creaky stairs avoid, fan hum masks moans.

Flashbacks: saw Jake shirtless pool once before, fantasized.

Post each: cuddle, kiss soft, contrast rough.

Sunday night climax: after family leaves, Emily shower. Jake in guest. Starts oral, vibe. Fuck missionary intense, eye contact "love your pussy more." Pound, creampie.

Emily knocks post-shower: "Lena? Smells like... cologne in hall?"

"Spilled Jake's aftershave helping unpack!"

He snickers, wiping cum thigh. As he dresses: "Screwed in guest room—check. Behind back—check. Next family reunion gonna be awkward."

Final line: Sex finishes with him coming, then Emily's knock. We compose. She leaves. He zips, cum drip floor. Slips, almost falls ass over. "Shit!" I laugh. "Graceful exit, fiancé. Don't trip on your own boner on the way out."

Yeah.

Now compiling full story.

I never set out to betray my sister, but temptation has a way of rewriting morals. Emily's house, guest room bed still warm from my body, sheets tangled witness to sin. It began Friday, escalated weekend, ended hilariously.

Arrived 4pm. Emily hugs tight. "So glad you're here! Jake's grilling tonight." Tour: kitchen modern, living cozy, guest room inviting—soft lighting, plush bed, private bath. Jake greets, hug lingers second long. Hand large, firm.

Barbecue perfection. Food delicious, company intoxicating. Emily rosé flushed. Jake's laugh deep. After dinner, games—cards, shots. Emily yawns 11:30. "Night, loves." Upstairs kiss Jake.

Jake and I clean. Sink dishes, brushes arms. "You're fun," he says. Couch chat. Knee touch becomes thigh stroke. Kiss inevitable. Fireworks.

Upstairs stealth. Door shut, world shrinks. Strip frenzy. His body: pecs hard, abs 8-pack, V-line leads trimmed bush, cock semi then full mast.

Foreplay epic. Kiss neck, ears nibble. Breasts massaged, nipples nursed. Belly kisses trail pussy worship. Legs wide, ankles held. Tongue darts hole, laps juices. Clit sucked vacuum. Fingers prostate curve. Build 10min, explode thighs clamp.

Blowjob return: kneel worship. Lips seal head, tongue laps underside. Inch down, throat relax. Nose pubes. Bob fast, slurp loud. Hand balls massage. He warns, swallow eager.

Fuck commence. Condom? No mention, bareback heat. Missionary: enter slow, 1inch pause savor. Full hilt. Rock gentle build pound. Hips snap, pubic grind clit. Hands pinned, dominant. Bite shoulder. Orgasm clench trigger his pause hold.

Doggy: knees spread, arch back. Enter slap. Pace brutal, ass ripple. Spank rhythm. Pull arms back leverage. Clit hand. Scream pillow.

Cowgirl: mount, hands chest. Bounce, hair flip. Lean forward kiss, back tits free swing. Grind circles. His hands ass spread finger rim tease.

Spoon side: intimate, leg lift. Slow deep, nipple pinch. Whisper "dirty girl cheating."

End missionary legs high. Thrust savage, balls tighten. "Take seed." Fill hot spurts 6-7. Ooze out.

Glow. Cuddle 20min. Round two tease, sleep.

Saturday wake BJ. Emily gone brunch. Jake gym return horny. Swallow load two.

Pool: bikinis. Emily nap. Jake lotions back, fingers stray ass crack discreet. Indoor quick fingerbang kitchen while she showers distant.

Night movie. Blanket handjob mutual slow.

1am visit. Vibe intro: clits buzz, insert pussy while tongue ass. Then vibe ass shallow, cock pussy full. Fullness insane. Switch positions vibe assisted.

Orgasm count high.

Sunday family brunch parents. Table footjob sneaked sockless.

Afternoon hike Emily Jake me. Trail hand brush.

Evening pack. Last chance. Emily store run milk. 20min quickie: stand wall, leg up, fast pump creampie.

Night finale. Post movie Emily bed. Jake 2am. Oil from bath. Massage full body. Cock oil slick titfuck: breasts squeeze, thrust neck level suck head each pass.

Prone bone: flat stomach, pillow hips. Enter ass up slight. Grind prostate hit. Hands forward pinned. Roll hips wave.

Standing door: back him, leg counter. Mirror angled watch connect. Deep angle new spot.

Lotus floor: face face, rock close kiss.

Bed pile driver edge: legs shoulder press fold. Gravity aid deep. Pound jackhammer. Final creampie overflow.

Pull out, lay pant.

Knock Emily: "Lena? Sounded like bed broke again. You doing yoga or something?"

"Yoga! Late night flow!"

Footsteps fade.

Jake sits up, cock soft slick. Reaches pants, steps in cum puddle—slip comically, arms windmill, catch dresser. "Fuck!"

I burst laughing silent tears. "Smooth, stud. Hooked up behind her back, but can't hook a step without your own jizz as lube."

He grins sheepish. "Worth it."

And scene.

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