The Catch Up

Doug wiped down the polished wooden bar at The Pine Knot, Aspen's go-to spot for locals who pretended the ski slopes didn't exist in summer. The place was a chaotic mix of hammered tourists and off-duty ski instructors, plates of elk burgers flying out from the kitchen like they were late for a powder day. He'd been slinging drinks here for two years, ever since ditching the corporate grind in Denver for something with actual fresh air. Tonight, the crowd was rowdy—some group in the corner belting out bad karaoke versions of old country tunes—but Doug kept his focus on the rhythm of pouring IPAs and nodding at regulars.

That's when he spotted her. Diane. She was tucked into a booth near the window, her dark hair catching the glow from the string lights strung haphazardly across the ceiling. She laughed at something her friend said, head thrown back, that same infectious energy he'd remembered from their wilder days. It had been over a year since they'd last crossed paths—back when their friend group was all about riverside barbecues and impromptu hookups in the park by the Roaring Fork. Doug remembered introducing her to a few Aspen transplants one summer evening, the air thick with weed smoke and the thrill of no expectations. They'd shared a threesome once with Cory under the cottonwoods, bodies tangled in the grass while the river rushed nearby, but that was ancient history now. Life had pulled them in different directions: her chasing freelance graphic design gigs, him settling into this bartending routine.

He caught her eye as he refilled a pint for the guy next to her booth. Diane's face lit up, and she waved him over during a lull. Doug slid behind the bar partition and approached, wiping his hands on his apron.

"Diane? Holy shit, it's been forever," he said, leaning against the booth's edge. Her friend excused herself to the bathroom, leaving them in a pocket of relative quiet.

"Doug! Yeah, way too long. What are you doing behind the bar? Last I heard, you were climbing mountains or some rugged bullshit."

He chuckled, pulling up a stool. "This pays the bills while I figure out the rest. You? Still designing those killer logos?"

They fell into easy chatter, catching up on the group. Cory had moved to Boulder, chasing a music gig after that concert hookup Diane vaguely recalled with a smirk. The old crew's antics came up—hiking trails where things got frisky after a few beers, spontaneous quickies that Diane laughed off as "the perks of summer in Aspen." She mentioned a recent hike up Maroon Bells, the kind where the wildflowers made her feel alive, echoing those riverside flirts they'd all shared. No one brought up the park threesome directly; it hung there like a shared secret, adding a layer of warmth without awkwardness. Doug poured her a free glass of the house red, on the house, and they swapped stories until last call loomed.

The restaurant emptied out around midnight, the karaoke dying into echoes. As Doug locked the side door, Diane lingered by the exit, her cheeks flushed from the wine and the late hour.

"Listen," he said, pocketing his keys, "my place is just a quick walk up the hill. Got a decent bottle of cabernet I've been saving. No pressure—just to keep talking. Feels like old times, minus the drama."

She tilted her head, considering. They'd always been friends first, the physical stuff a bonus from their friends-with-benefits phase. Nothing serious, just fun. "Sure, why not? A nightcap sounds perfect."

His apartment was a third-floor walk-up in a creaky building off Main Street, the kind with mismatched furniture and a view of the stars if you craned your neck. Doug flicked on a lamp, the warm light spilling over a worn leather couch and a coffee table cluttered with trail maps. He uncorked the wine, pouring two generous glasses, and they settled in, legs stretched out, the conversation flowing like the Roaring Fork after a melt.

One glass turned into two, the wine loosening tongues and memories. Diane leaned back, her sundress riding up slightly on her toned legs—legs that Doug remembered wrapping around him during those park escapades. But this was different; they were older, wiser, content with friendship. Or so they thought.

Diane set her glass down, her eyes lingering on his broad shoulders, the way his shirt stretched across his chest from years of hauling kegs and hitting the gym. "I love your strong chest, shoulders, and back, my sexy honey," she said, the words slipping out half-teasing, half-serious, the wine making her bold.

Doug's pulse quickened. He met her gaze, feeling that old spark ignite. "And I love your sexy body, your perfect breasts and toned back, ass, and legs… oh my gosh. I’m feeling sailor-y. I want to kiss those lips."

She didn't pull away. Instead, she shifted closer on the couch. "I want to kiss you deeply and feel your body pressed against mine."

It happened fast, like a summer storm rolling in. Doug leaned in, capturing her mouth with his. Their lips met soft at first, then hungry, tongues brushing in a familiar dance. "We thought the same thing," he murmured against her skin. "I love kissing you, feeling your tongue with mine, lips pressed."

Diane's hands roamed up his arms, pulling him tighter. Their legs entwined naturally, bodies aligning on the couch. He rolled them onto their sides, still locked in the kiss, the world narrowing to the heat between them. One of Doug's hands cupped her face, thumb tracing her jaw, while the other slid down her side, mapping the curve of her hip.

She arched into him, her own hand gripping his ass, holding him close. "Our legs entwined. You roll us on our sides still kissing."

"Yummy," he breathed, his voice rough. "Your leg draped over my hip. Pulling you close."

His hand ventured lower, brushing the front of her dress, fingers grazing the damp fabric between her thighs. She was getting wet, the evidence of her arousal soaking through. Diane gasped into his mouth, her body responding instinctively. He could feel himself hardening against her, his dick straining against his jeans.

"You put your fingers between my lips," she whispered, guiding his hand under her dress, past the edge of her panties.

Doug looked into her eyes, seeing the mix of love and lust swirling there, raw and unfiltered. His fingers slipped between her slick folds, teasing her entrance. "I look into your eyes, and see love and lust all mixed together." His other hand rested on her belly, feeling the rise and fall of her breaths.

He trailed kisses down her neck, nipping at her shoulder. "I want to kiss you all over, taste you."

"Mmmm, I love your gentle kisses," Diane moaned, her head falling back.

Looking up, Doug saw the desire mirrored in her face—she wanted him as much as he wanted her. One hand stroked up and down her back and ass, squeezing the firm muscle there, while the other played at her clit, circling the swollen nub before dipping inside. She was so wet, her pussy clenching around his fingers. "I want you so much, and you can feel it."

"You put two fingers inside and you know I want you," she said, her voice husky.

He curled them, pressing against her G-spot, thumb rubbing her clit in steady rhythm. Their mouths crashed together again, the kiss deep and urgent.

Diane's hand mirrored his, sliding down to his lower belly, then lower, caressing the bulge of his dick through his pants. "I’m touching your lower belly and glide down to caress your penis."

"Ohhhh," Doug groaned, thrusting lightly into her grip. "I love your touch." His fingers moved in and out of her pussy, slick sounds filling the room as she spread her legs wider without thinking. He kissed her hard, hungry, devouring her like he'd been starving.

She pulled back slightly, her eyes dark with need. "I’m touching myself... why I’m not writing. I want your mouth on me but also want to lick and suck you, so turn you to back so I can get on your face."

"Yes!" Doug flipped onto his back, shedding his shirt in one motion, his strong chest rising and falling. She straddled his face, hiking her dress up and shimmying out of her panties, her bare pussy hovering inches from his mouth. His cock throbbed as she unzipped his jeans, freeing him. He was so hard, the tip already leaking pre-cum.

Diane leaned down, taking him in her mouth, licking around the head with slow, teasing strokes. Her tongue flickered along the underside, gentle up and down.

Doug's hands gripped her thighs, pulling her down onto his face. His tongue delved between her lips, lapping at her wetness, tasting her salty-sweet essence. "My face between your legs, my tongue licking your lips, you feel it moving inside you. I love the view of you sitting on my face, your wet pussy and perfect ass!!!" His hips bucked up, pushing his dick deeper into her mouth. "Put it all the way in." He worked his tongue in circles on her clit, sliding two fingers back into her pussy, pressing her G-spot firmly.

She alternated between sucking softly and harder, her lips sealing around his shaft, creating delicious suction as she bobbed. "I’m alternating between sucking softly and harder. I want you so much, my love."

"You like me in your mouth?" Doug asked, his voice muffled against her folds. "Tell me. Because I love eating you out!!! You react so well. I want you to cum on my face, hips grinding."

"Yes..." Diane moaned around his cock, the vibration sending shocks through him. She felt him getting harder, so she sucked rhythmically, taking him all the way down, maintaining suction as she pulled back.

His dick filled her mouth, thick and pulsing. "My cock in your mouth. You like it, I can tell." Doug's tongue tasted every inch of her, loving how she tasted—musky and aroused. His hands spread her ass cheeks, the view obscene and perfect: her tight hole and dripping pussy, his fingers plunging in and out. He slipped a third finger inside her, stretching her, and she ground down harder, her clit rubbing against his tongue.

"I love to feel your tongue lick all around and be inside me," she gasped, popping off his cock for a breath before diving back in.

"My tongue is EVERYWHERE." Doug flicked and probed, feeling her building, her G-spot swelling under his fingers. She was so wet, juices coating his chin. "You feel me building up, I want to cum with you sucking me! You’re building too, I can feel your spot hardening and you’re so wet. My fingers filling you up, my strong tongue on your clit."

Diane's body tensed, her mouth working him faster. She came hard, shuddering on his face, her pussy clenching around his fingers as waves of pleasure ripped through her. "I just came thinking about that as I touched myself," she panted, though in the moment, it was real, her orgasm soaking his mouth.

Doug's hips pushed up, fucking her mouth in shallow thrusts. "My hips pushing me into your mouth."

But she wanted more. Pulling off with a wet pop, she looked back at him, eyes wild. "I want you inside of me, sweetheart."

"I was thinking about you sucking me all the way… oh my gosh. Told you I was feeling like a sailor."

They disentangled, both breathing heavy, clothes discarded in a frenzy. Doug's body was all hard lines—broad shoulders, defined abs from those Aspen hikes—and Diane's was a masterpiece of curves: full breasts with dark nipples, a toned back flaring to a round ass, legs that went on forever. She pushed him back down, straddling his hips, but first, she wanted to finish what she'd started.

Diane took his cock in hand, stroking the length, slick with her saliva. She sucked him deep again, her throat relaxing to take him fully, one hand fondling his balls. Doug groaned, his fingers tangling in her hair, not pushing but guiding. She loved the taste of him, the way he throbbed on her tongue. As she hollowed her cheeks, increasing the suction, he couldn't hold back.

"Fuck, Diane, I'm gonna cum," he warned, but she didn't stop, humming encouragement. His hips jerked, and he exploded in her mouth, hot spurts of cum hitting the back of her throat. She swallowed every drop, milking him dry, her eyes locked on his as she savored it.

"God, that was intense," Doug panted, pulling her up for a kiss, tasting himself on her lips.

But they weren't done. Diane's pussy ached for him, still pulsing from her orgasm. She positioned herself over his semi-hard dick, which twitched back to life quickly under her touch. Sinking down, she took him inch by inch, her wetness making the slide easy. "Fuck, you feel so good," she moaned, rolling her hips.

Doug gripped her ass, thrusting up to meet her. They moved together, a rhythm born of old familiarity—deep, passionate strokes that hit all the right spots. He sat up, capturing a nipple in his mouth, sucking hard while she rode him. Her hands braced on his shoulders, nails digging in.

"Choke me a little," she whispered, remembering how she enjoyed that edge during oral, the control it gave her. Doug's hand came up, fingers wrapping loosely around her throat, applying just enough pressure to make her gasp, her pussy clenching tighter around his cock.

They flipped positions, Doug on top now, pounding into her with controlled force. Her legs wrapped around his waist, pulling him deeper. "Harder," she demanded, and he obliged, the slap of skin on skin echoing in the small apartment.

Diane's second orgasm built fast, her clit grinding against his pubic bone. "I'm close—fuck, Doug, don't stop." He reached between them, rubbing her clit in circles, and she shattered, crying out as her body convulsed, squirting a little against him, soaking the couch.

That pushed him over the edge again. With a guttural moan, Doug buried himself deep, cumming inside her, filling her pussy with his release. They collapsed together, sweaty and spent, his weight a comforting press.

As their breathing slowed, Doug kissed her forehead. "That was... unexpected, but damn, I'm glad it happened."

Diane smiled, tracing patterns on his chest. "Me too. Friends with benefits upgraded, huh? But let's keep it casual—no strings, just like old times."

He laughed, pulling her closer. "Deal. Though if this is what nightcaps lead to, I might start inviting you over more often."

In the quiet afterglow, with the Aspen night humming outside, they dozed off entwined, the wine glasses forgotten on the table. Come morning, over coffee and easy banter, Doug walked her out, both knowing this reunion had reignited something fun—proof that some sparks never fully die, they just wait for the right breeze. And as Diane headed down the hill, a playful wink over her shoulder, Doug couldn't help but grin, already plotting the next "no strings" excuse.