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A Second Chance At First Love

A Second Chance At First Love

by windowpeeler
19 min read
4.57 (5800 views)
adultfiction

Andrew keyed the ignition of his sedan and let out a slow breath, watching as dusk set the sky aflame with shades of orange and purple. The city around him seemed less like a bustling metropolis and more like a hushed stage set for something momentous. He had waited for this night. Anticipated it since that first tentative message on social media weeks ago. The moment he saw the familiar name and picture--Lisa Merritt (now Lisa Redford, but divorcing)--everything inside him shifted, as though ghosts from their teenage years had stirred awake.

They were both divorced now, both a little bruised by life. Both in need of something real, or maybe just a reminder of who they had once been.

He checked his phone again to verify her address. They had agreed to meet at a wine bar downtown for dinner and drinks. Lisa had insisted, half-jokingly, that she pick the place so that if the night somehow derailed, she could blame the ambiance rather than any fault of theirs. Andrew only chuckled at that. Nothing could possibly go wrong if she was in front of him--he had dreamed about her for years.

He drove in comfortable silence, letting the hum of traffic bolster his thoughts. Memories of Lisa from high school came rushing back: senior prom when she wore that crimson dress with a single rose pinned to her hair, the night they almost kissed on the football field but hesitated too long, that half-smile she always offered him whenever they locked eyes in the hallway. He'd been shy, and she'd been dating someone else. Their timing was never right. Then life happened--college, marriages, divorces. A messy swirl of experiences they'd each endured separately. And now, they were about to see if maybe, just maybe, it was time for their paths to finally intersect.

A Meeting Long Overdue

When Andrew entered the wine bar, the hostess welcomed him with a practiced smile. Soft golden lights illuminated the space, and the hum of conversation drifted like a gentle wave around them. He felt a sudden flutter in his stomach--part excitement, part nerves. Would she be the same Lisa he had once known, just older? Or would life have shaped her into someone unrecognizable?

Before he could dwell too much, he spotted her at a corner table. She was turned slightly away, scrolling through her phone. Light caught her hair--a deep, warm chestnut color that tumbled over her shoulders. She seemed smaller than he remembered, or maybe that was just the intimate setting casting a close-knit glow. Her lips curved in a relieved smile the moment she looked up.

"Andrew," she said, standing to give him a gentle hug. It felt like home, familiar in a way he hadn't experienced in a very long time. There was a slight tremor in his chest as they parted.

"You look amazing," he managed, trying not to stare too much at the subtle lines in her face that only seemed to accentuate her beauty, marking the life she'd lived since they were eighteen.

"And you look... well, older--but in a good way," she teased, eyes shining. "Still have that sincerity in your face, though."

He laughed, and they settled into their seats. Immediately, they fell into easy conversation, as if the intervening years were just a thin veil they could brush aside. They talked about high school memories, the time Lisa climbed out the classroom window to avoid a test, the day Andrew accidentally tripped over the principal's foot and spilled paint all over the hallway. Even the heartbreaks in their later years were less painful to recount in each other's company.

"It's weird, right?" Lisa remarked at one point, sipping her Cabernet. "I mean, how we never really found the chance back then? I always thought, you know, maybe I should have asked you out after Greg and I broke up, but then you were always so..."

"Shy," Andrew supplied.

"Exactly," she said, crinkling her nose in that gentle, playful way he remembered. "But I wanted to talk to you so many times."

He swallowed, a warmth settling into his chest. "Better late than never."

Her eyes danced. "Absolutely."

Dinner and Confessions

The waiter appeared with their entrΓ©es--grilled salmon for her, a steak for him. Conversation dipped into the heavier things. Lisa admitted how her marriage had disintegrated over five barren years--no real intimacy, almost no communication, like two ghosts inhabiting the same house. Andrew sighed, confessing that his own divorce was a dull ache that refused to go away, though it was definitely for the best. His ex-wife had grown distant, and neither knew how to rebuild the fractured trust.

"I can't believe it took so long to finalize everything," Andrew said, regarding the swirling wine in his glass. "Now that it's over, I just feel... a mixture of relief and guilt. Like maybe I should have tried harder, or maybe it was doomed from the start."

Lisa reached over the table and placed a comforting hand atop his. "I used to think that way too," she confided. "But you can't stay in a loveless marriage. It drains you. You forget who you are. Before you know it, you're just going through the motions."

He met her gaze. "That's exactly how it felt."

She nodded, eyes softening. "Then, there's the other part. The bedroom part."

Andrew felt a flush on the back of his neck. He remembered nights of dissatisfaction, that sense of mechanical repetition rather than genuine heat. He nodded slowly. "Yeah, that was... lacking, too."

Lisa exhaled. "Tell me about it. My ex--" She paused, taking another sip of wine as though bracing herself to admit something deeply personal. "He had a... single-minded approach, let's call it. He didn't like to try anything new, definitely didn't like me getting creative."

Andrew's brows lifted. "I guess I can relate. My ex liked routine. The same, every time."

Lisa smiled wryly. "Well, that's behind us both now. Maybe we can... explore." She let the word linger, and Andrew felt a jolt.

He coughed softly, taking a gulp of water to re-center. This conversation was venturing into territory he was both intrigued by and nervous about. "So, you're... open to trying new things?"

She smirked. "Are you?"

He met her gaze. Somewhere in that question lay a challenge, a spark that had never ignited between them when they were teens. His heart pounded. "I'd like to think so."

The Drive to Her Place

They lingered in the wine bar longer than expected. Conversation was too rich, too entertaining to cut short. A second glass of wine turned into a third, but both were mindful not to cross any lines of inebriation--they wanted clarity for the night that lay ahead.

Eventually, Lisa suggested they continue talking somewhere more private. Andrew agreed immediately. Memories of her, combined with the fresh swirl of desire building in his chest, made it impossible to say no. They decided on Lisa's place, a modest suburban home she had purchased after her separation.

On the drive, Andrew found himself rehearsing possible lines, things to say to ease any tension. But all his practiced phrases felt flat and unnecessary. Whatever was going to happen would unfold naturally--he could sense that.

He pulled up to her driveway, noticing the tidy yard and a small porch light casting a welcoming glow. A wooden wind chime tinkled softly in the breeze. Lisa guided him in. The house was cozy: plush carpets, warm lighting, and faint lavender scents lingering in the air.

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"Make yourself comfortable," she said, slipping off her heels. "I'll grab us some water, maybe a light drink if you want."

"A little water first, sure," Andrew replied, removing his jacket and draping it over a chair.

He surveyed the living room--shelves stacked with books, photos of Lisa with her parents, a small painting of a tranquil beach. She returned moments later with two glasses of water and a mischievous smile.

"We could open a bottle of wine if you'd prefer," she said, handing him a glass.

He chuckled. "I think we're both tipsy enough already. Let's keep our wits about us."

She nodded, eyes flicking to the sofa. "Sit with me."

Couch Confidences

They settled together, knees nearly touching. The hum of nighttime silence enveloped them, broken only by the occasional buzz of a passing car.

"So," Lisa began after taking a small sip. "You said you wanted to try new things."

Andrew inclined his head. "I did."

Her lips curled into a half-smile. "I should warn you, I spent so many years in a... let's call it passionless bedroom. I've got a list of fantasies--some mild, some not-so-mild--rolling around in my head that I never got to try."

Andrew swallowed, his pulse leaping. A swirl of heat prickled the base of his spine. "I... I'm game to hear them."

She grinned. "There's one I've been thinking about for ages. My ex wasn't into it--he thought it was weird, probably. Maybe too... kinky for him. But I always dreamed of, well, controlling exactly how a man finishes. Or doesn't finish. Like, letting him get right to the brink and..." She trailed off.

Andrew's mouth went dry. The words conjured images in his mind of her teasing him, taking him to the very edge. He cleared his throat. "So you're talking about... edging?"

She laughed softly. "Kind of. But specifically, I'm fascinated by the idea of what's sometimes called a 'ruined orgasm.' I've never seen it happen. Never done it. The idea is thrilling in my head: the man is so turned on, so desperate that he can't hold back. And then... I do something to let it out, but not in the usual way. It's a bit... humiliating, maybe, but that's part of the excitement. You get to watch him unravel."

Andrew's heart drummed a rapid staccato. He tried to wrap his mind around the concept--someone intentionally meddling with that final crescendo, so it releases without the intense pleasure of a full orgasm, leaving him in a haze of longing. Part of him bristled at the idea, worried it might be too intense or even disappointing. Another part, an unexpectedly large part, sizzled with curiosity and arousal.

He exhaled. "I've never tried that... but I'd be lying if I said I wasn't intrigued."

She set her glass down, her face open and earnest. "Really?"

He nodded. "Yes. I mean, if it's something you want to experience. I... I trust you."

Her grin widened. "Andrew, oh my God. You have no idea how hard it was for me to say that out loud. I've been carrying this little fantasy in my head for years. I always thought any partner I told would look at me like I was crazy."

He smiled gently, placing a hand on hers. "I get it. We've both had a lot of years with the wrong people--people who never bothered to explore or understand. This is a new chapter."

She exhaled, relief and excitement warring in her eyes. "So, you wouldn't mind trying it, just once, for me?"

Andrew hesitated only for a second, a thousand swirling emotions flooding him. But then he recalled the nights of monotony, the emptiness of going through the same motions, never feeling the spark of experimentation or surrendering trust to someone else. Maybe this was the moment to say yes to life, to something new, with someone who genuinely wanted to explore.

He nodded, voice coming out quiet but resolute. "Yes."

The Bedroom Invitation

Lisa's face lit with an eager excitement he'd never witnessed before. She guided him to her bedroom, which was a surprisingly cozy space with warm taupe walls and a large bed adorned with fluffy pillows. A few candles flickered around the room, adding a subtle glow that made the shadows dance across the ceiling. She must have set them out earlier, hoping the night would lead here.

At the corner of the room was a small dresser, and Lisa rummaged through a drawer. Andrew felt his heart pounding as he watched her produce a small box of latex gloves. She turned to him, almost shy now that the moment was upon them.

"Better safe than sorry," she joked, waving one of the gloves. "Plus, it helps me keep it... well, precise."

Andrew let out a shaky laugh, removing his tie and unbuttoning his shirt. Nervousness blended with anticipation. He had never done anything remotely like this. Yet something about Lisa's confidence--tempered with that glimmer of excitement in her gaze--made him feel safe.

They kissed then, a slow, lingering meeting of lips that tasted of cabernet and longing. It was gentle at first, but soon the hunger within them both sparked a deeper intensity. Her hands slid over his shoulders, down his chest, tugging his shirt off. He reciprocated, slipping the straps of her dress off her shoulders, baring her skin to the warm candlelight.

When they finally broke apart, breathless, Lisa guided him onto the bed. A swirl of sensations enveloped him as he sank into the soft blankets, her body pressing alongside his. She teased him, letting her hands roam lightly, exploring every inch of his torso, occasionally grazing just below the waistband of his trousers. The lightness of her touch was excruciatingly arousing, especially knowing what was to come.

Building Anticipation

Lisa's body was supple beneath his hands. They kissed and explored, reacquainting themselves with the thrill of new intimacy. She'd moan softly when he pressed against her neck or cupped her waist just right. He found himself growing harder, breath hitching whenever she trailed her nails along his thigh.

Eventually, she sat back, chest rising and falling with each breath. "Ready?" she whispered.

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Andrew inhaled, a crackle of nerves mingling with electrifying desire. He nodded.

Lisa reached for a single latex glove and slid it over her right hand with a practiced snap. She also grabbed a small packet of lubricant from the dresser, seemingly well-prepared. Andrew's eyes widened slightly at the sight, but he nodded, lying back.

"Relax," she murmured, pressing a slow, tender kiss to his mouth before moving lower, trailing down his chest, his stomach. Every press of her lips stoked the fire in him.

Andrew felt a pulse of longing between his legs, an aching need that had grown steadily since they'd begun. Her hands moved expertly, coaxing him to full hardness. He moaned as she teased him, swirling her tongue along his inner thigh, but each time he gasped or tried to urge her to go further, she'd pull back, leaving him panting, half-mad with want.

"You've been teased enough, I think," she said, her voice husky. "But remember, I'm in control tonight."

He watched her push his legs apart gently. She drizzled a little lube on her gloved fingers. The sensation of the cool air against his heated skin made him shiver. Lisa's eyes gleamed with a mixture of compassion and mischief.

"Just breathe," she repeated.

The Slow, Exquisite Torment

What followed was a slow, methodical exploration that sent Andrew's senses into overdrive. Lisa's gloved finger began by tracing small circles around that sensitive spot behind his testicles, occasionally brushing near his entrance. He felt each stroke as a shot of electricity, his entire body taut with arousal.

He'd never experienced such deliberate teasing before. His breath caught when she finally pressed a lubricated finger inside. The intrusion was foreign and intense, but her gentleness put him at ease. Once she found the subtle pressure point deep within, Andrew's body tensed in a rush of pleasure so profound he nearly cried out.

"Oh God--Lisa..."

She smiled, leaning in to nibble his ear. "Feel good?"

He could only nod, incapable of speech for the moment. The pressure she applied was excruciatingly perfect, not too rough, not too timid. Every time she shifted her angle slightly, a fresh wave of sensation blazed through him, leaving him breathless.

His erection throbbed with unmet need, longing for the familiar friction of a hand or mouth. But Lisa's intention tonight was to do something else entirely. Her eyes were alight with that playful mischief, the same spark he remembered from high school, but magnified by years of pent-up desires.

Slowly, meticulously, she coaxed him to the edge. Several times, Andrew felt that telltale rush signaling the precipice of release. He groaned, hips trembling, body clamoring for the final push. Yet each time, Lisa eased off, pressing a hand against his stomach to keep him from thrusting, breathing hot words of reassurance into his ear.

"I've got you," she murmured, her voice soothing yet commanding. "Just let me do this."

He nodded weakly, sweat beading on his brow. Every muscle in his body seemed to hum with tension, as if all his focus converged on that single spot where her finger teased against his prostate.

Time lost all meaning. It could have been minutes, it could have been hours. The only constants were the racing of his heart, the gentle swirl of Lisa's finger, and the building wave of pleasure that threatened to crest.

At last, when Andrew thought he couldn't bear the ache another second, Lisa changed her angle. She removed the subtle rocking motion of her hand, pressed just firmly enough for him to realize there was no going back.

His body started to convulse in the prelude to orgasm, mind screaming for the familiar grip of a hand on his shaft, or some urgent pumping to coax the pleasure out fully. Instead, Lisa pinned his hips with her free hand, preventing him from any friction.

"Lisa, oh God, I'm--"

She grinned wickedly, leaning close to whisper, "Let it go."

The Ruin

The wave broke. Andrew felt the climax ripple up from his toes, washing through his entire body. But something was off--there was no explosive burst of euphoria. Instead, the contractions of his muscles forced out a hot, pulsing release, but with none of the mind-shattering pleasure he was used to. It was as though the orgasm was happening to him, rather than with him, drained of the usual crescendo but still unstoppable.

His mouth hung open in a silent cry. He felt the wetness seep out, felt his body quake, but the ecstasy was... muted, elusive, just out of reach. Instead of sweet relief, he was left with a shuddering emptiness--a physical release that only served to highlight the mental frustration of not reaching that apex of bliss.

He groaned, half in ecstasy, half in torment, eyes flying open to see Lisa's gaze locked on him, her lips parted in awe. She watched, enthralled, as each twitch of his body gave up more of his pleasure in a slow, almost agonizing unraveling.

Andrew's breath caught in his throat, a contradictory mix of intense arousal and disappointment washing over him. The need to climax properly pulsed through him, but it was too late--his body had already emptied. This was the ruin, the very act Lisa had wanted to see.

She withdrew her finger, still wearing that latex glove. For a moment, neither of them spoke. Andrew's chest heaved with ragged breaths, heart pounding as though he'd run a marathon. Lisa carefully disposed of the glove in a small trash bin by the nightstand, then turned back to him with a glimmer in her eye--a heady combination of triumph, fascination, and something else altogether.

"You look..." She bit her lower lip, almost overwhelmed, "so gorgeous like that. I've fantasized about this for so long."

Andrew could barely form words. His body felt drained yet paradoxically still hungry for more. He wanted to pull her into his arms, ravish her, find some redemption in a second round. But he also felt the weight of that ruinous orgasm, the knowledge that his body had already spent itself.

He managed a shaky laugh. "That was... intense."

Lisa crawled onto the bed beside him, pressing a lingering kiss to his cheek. "You're okay?"

He nodded, though he couldn't hide the yearning in his voice. "Yeah, I'm just... I still kind of want it, you know?"

She ran a hand through his hair, gentle and teasing. "I know. It leaves you wanting more, doesn't it?"

He breathed out slowly. "That's the whole point, I guess?"

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