Two Guy Aspen Weekend

Diane stepped into the hotel bar in Aspen, her scrubs swapped for a simple black sweater and jeans that hugged her legs after a long shift at the hospital. The place hummed with the low buzz of conversations and the clink of glasses, but she zeroed in on the bartender mixing something with a flourish. She ordered a bold red wine, the kind that bit back just enough to shake off the day's exhaustion. That's when she noticed him—Missed Opportunity Guy, as she'd later dub him in her mind—sitting a stool away, nursing a whiskey. He had that easy, outdoorsy look: tousled hair, a flannel shirt rolled up at the sleeves, like he'd just come off the slopes.

He caught her eye and grinned, sliding over. "Rough day saving lives?" he asked, his voice carrying a hint of a drawl. Diane laughed, surprised at how quickly the banter flowed. They talked about the mountain air, her shifts pulling her away from the fun, his solo trip to clear his head. Two drinks in, he leaned closer. "Why don't you crash with me for the weekend? I've got a room upstairs, killer view." She hesitated for a beat, then nodded. Why not? Spontaneous was her vibe lately, especially after that spark of flirting at the après-ski party last month—reminded her of dancing close with someone who knew how to move.

Up in his room, the energy shifted fast. Missed Opportunity Guy pulled her in for a kiss that started promising but fizzled into something rote. Clothes hit the floor in a heap—her sweater, his shirt revealing a decent but unremarkable chest. He was eager, hands roaming her body, cupping her tits as he kissed down her neck. Diane arched into it, her pussy already warming from the wine and the thrill. He laid her back on the bed, spreading her legs to lick at her clit with mechanical swipes of his tongue. It got her wet, but not soaked—not the way she craved. She guided his head, but he didn't pick up the rhythm.

"Fuck me," she murmured, pulling him up. His dick was average, hard and ready, sliding into her with a grunt. He thrust steadily, missionary style, his hips slapping against hers in a predictable beat. Diane wrapped her legs around him, trying to grind deeper, but he was all surface-level pumps, no real drive to push her over the edge. She came anyway, a mild ripple through her body, clenching around him as he groaned and spilled inside her, hot cum filling her pussy in spurts. He rolled off, breathing heavy, and they lay there catching their breath. It was fine—average, like a solid B-minus fuck—but she already sensed the weekend might drag.

Morning came with coffee and more talk. They headed out for a hike that afternoon, the trail winding up the mountain under a crisp blue sky. Diane pulled ahead, her legs carrying her faster, the fresh air sharpening her senses. Missed Opportunity Guy lagged, pausing to tie his boot or snap photos. Halfway up, she rounded a switchback and nearly collided with another hiker—NY Finance Guy, tall and sharp-featured, with a polished jacket and a backpack that screamed city transplant. "Whoa, easy there," he said, steadying her with a hand on her arm. His eyes lingered, dark and appraising, and Diane felt a jolt—attraction, raw and immediate.

"Trail mix mishap?" she joked, nodding at his pack. He laughed, a deep sound that cut through the wind. "More like bad timing on the ascent. You from around here?" They chatted for a minute—her hospital gig, his finance world in New York, the irony of escaping the grind in Aspen. There was chemistry, the kind that made her skin tingle, but the trail called. "See you on the way down?" he said, flashing a smile that promised more. Diane nodded, pulse quickening as she continued up.

At the summit, the view hit like a rush—snow-capped peaks stretching out. Missed Opportunity Guy finally caught up, sweaty and out of breath. "You move fast," he panted, pulling her in for a quick kiss. They descended together, but Diane's mind wandered back to that encounter, the easy spark with the New Yorker. In the parking lot, as she grabbed water from her car, NY Finance Guy appeared from his SUV, scribbling on a card. "St. Jerome Hotel," he said, handing it over. "If you're free later. Room 512." His gaze dropped to her lips, then back up, bold without being pushy. She pocketed it, a secret thrill buzzing in her veins.

Back at Missed Opportunity Guy's hotel, the evening devolved into routine. They showered off the hike, and soon enough, he had her bent over the bed, fucking her from behind. His hands gripped her hips, dick sliding in and out of her pussy with the same lackluster pace as before. Diane pushed back against him, chasing friction, but he was grunting too soon, cumming deep inside her again—warm seed mixing with the remnants from last night. She faked a stronger orgasm than she felt, rolling her eyes inwardly at his quick finish. As he collapsed beside her, spent, Diane sat up, still feeling his cum leaking slowly from her folds.

"That was great," he mumbled, eyes half-closed. She dressed quickly, the stickiness between her thighs a reminder of the mediocrity. "Hey, listen," she said, keeping it light. "Thanks for the weekend—the drinks, the hike. But I'm heading out. Got some stuff to handle." He blinked, confused, but she was already at the door. "Take care." No drama, just done. She didn't bother cleaning up; the mess felt like punctuation on a chapter closing.

The St. Jerome loomed elegant against the evening sky, all sleek lines and glowing windows. Diane texted the number: *Here.* NY Finance Guy—let's call him Alex, though she wouldn't learn his name till later—met her in the lobby, looking effortlessly sharp in a button-down. "Glad you came," he said, his hand brushing her lower back as they headed to the bar. Dinner followed in the hotel restaurant: steak for him, salmon for her, wine flowing bold and rich, the kind she loved for its playful edge. Midway through, under the table, his foot nudged hers, then his hand found her thigh during dessert. They made out right there in the booth, his tongue teasing hers, fingers tracing her neck. Heat built fast, her pussy throbbing despite—or maybe because of—the cum still slick inside her.

They barely made it to his suite. Alex kicked the door shut, pressing her against it, mouth on hers as hands yanked at clothes. Her sweater gone, bra unhooked, he sucked her nipples hard, teeth grazing just enough to make her gasp. "Fuck, you're hot," he growled, dropping to his knees. He hiked up her skirt—no panties, a last-minute skip—and buried his face in her pussy. His tongue was expert, lapping at her clit in firm circles, then delving into her folds. He tasted the remnants of Missed Opportunity Guy's load, the slick mix of cum and her arousal, and instead of pulling back, he groaned into her. "Sloppy seconds? Even better—makes you so fucking wet." Diane's knees buckled, fingers in his hair as he ate her out, sucking her lips, fingering her deep until she came hard, juices flooding his mouth.

He stood, dick straining against his pants—thicker than Missed Opportunity Guy's, veined and eager. She dropped to her knees, taking him in her mouth, swirling her tongue around the head, tasting salt and pre-cum. He fucked her face gently at first, then deeper, hands guiding her. "That's it, suck that cock." She gagged a little, loving the stretch, until he pulled her up and bent her over the couch. Doggy style, he slammed in, her pussy gripping him tight around the leftover cum. It squelched with each thrust, messy and hot, his balls slapping her clit. "You like that? My dick filling you up with his mess still in there?" She moaned yes, pushing back, the angle hitting her G-spot until she shattered again, walls pulsing.

They moved to the bed, where he flipped her onto her back and ate her out once more, then fucked her missionary, slow and deep, building to a frenzy. He came inside her, adding his load to the mix, hot ropes painting her insides. Exhausted, they collapsed, but it wasn't over. After a breather, she straddled him, riding his dick reverse cowgirl, grinding until he flipped her for more. Oral again—her on him, him on her—sixty-nine with her pussy dripping cum onto his chin. He fingered her ass while licking her, prepping her, and soon she was on all fours, begging for it. "Fuck my ass," she said, and he did, lubed with spit and her wetness, inching in slow. The stretch burned then bloomed into pleasure, his cock pounding her tight hole while his fingers rubbed her clit. She came screaming, and he pulled out to cum on her back, sticky lines cooling on her skin.

Saturday blurred into exploration. They ordered room service, fucked on the floor—her on top, tits bouncing as she rode him to mutual orgasms. In the shower, water cascading, he took her against the tiles, doggy style again, but this time in front of the full-length mirror. Diane loved watching—her face contorted in ecstasy, his dick disappearing into her pussy, water streaming down their bodies. "Look at you taking it," he murmured, thrusting harder. She watched her tits sway, his hands gripping her ass, until she squirted a little, soaking his thighs. He came in her mouth after, her swallowing every drop as she knelt, the water rinsing them clean.

Night fell, and they hit the hotel pool after hours—deserted, steam rising from the heated water. Skinny dipping turned to making out, her legs wrapped around him as he fingered her underwater. He sat on the edge, and she sucked his dick, the chlorine scent mixing with his musk. Back in the water, he fucked her against the pool wall, slow to avoid splashes, her nails digging into his shoulders. Another round on a lounge chair, him eating her out until she came, then missionary under the stars, cumming on her tits—warm spurts she rubbed in like lotion.

Sunday mirrored the intensity: lazy morning sex on the balcony, her blowing him while he sipped coffee. They hiked a short trail, stealing kisses, then back for shower sex—anal this time, her bent over, his cock sliding into her ass with soap as lube. He came inside, filling her, the sensation making her finger her pussy to another orgasm. Evenings meant dancing in the suite to slow music, bodies grinding leading to floor fucks, doggy in front of the mirror again because she couldn't get enough of the view—her pussy stretched wide, his dick glistening.

By Monday, as they packed, the high lingered. "Come to New York," Alex said over breakfast, his hand on hers. "My place, the city—let's see where this goes." Diane smiled, intrigued. She flew out that week, landing in his sleek Manhattan apartment overlooking the skyline. The sex was electric from the start—on the kitchen counter, her legs spread as he ate her out, then fucked her standing, cumming in her pussy. They did it in his office chair, her riding him while he worked late, and on the rooftop at night, risky and raw, his load on her back under the city lights.

But the city wore on her. The noise, the pace—it clashed with her mountain soul, the spontaneous vibes she cherished, like those pre-work quickies that kept life exciting. After a week of intense fucks—oral marathons, ass play with toys he pulled out, her squirting on his sheets—she realized it. Over coffee one morning, post-shower sex where he'd cum in her mouth, she said it gently. "This has been incredible, Alex. But I'm not a city girl. Aspen's my rhythm."

He nodded, understanding flickering in his eyes. They parted with a final, tender fuck—slow and deep, him inside her pussy one last time, cumming together in a quiet release. No regrets, just satisfaction. Back in Aspen, Diane hit the hospital trails, the memory of those wild days fueling her steps. She met friends for après-ski, danced close with a new face, feeling that familiar spark. Life was full of opportunities—not missed, just chosen. And damn, if the right ones didn't make every ache worthwhile.