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Maddy's Date Night

"Maddy goes on a date for the first time in 2 years, What will it bring."

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Author's Notes

"A very exaggerated account but I was also thinking of someone else when I wrote this. They know who they are and I would love to say Thank You to them both. xxx"

My name is Madeline, but I much prefer Maddy. It feels softer, less formal, more me. At Fifty-Four, I’ve learned a thing or two about what feels like ‘me,’ and what doesn’t. Tonight, ‘me’ was a trembling bundle of nerves and raw anticipation, clad in a sleek, midnight blue satin slip dress that whispered against my skin with every shallow breath. The silk was cool, but my skin burned beneath it. I hadn’t dressed like this in… well, it had been a while. A very long while. Nearly two years, to be precise, since I’d felt the intimate brush of another woman’s skin against mine, since I’d tasted the salt and sweetness of desire on another’s tongue. Two years since the last time I’d been truly, deeply, deliciously fucked. My body, usually a comfortable companion, had become a quiet, yearning entity, a vessel waiting to be filled. The longing was a dull ache most days, but tonight, it throbbed, a fierce, insistent drumbeat pulsing through every vein.

The taxi hummed through the evening streets, the city lights blurring into streaks of gold and ruby outside my window. My gaze was fixed on the glowing dot of my destination on the ride-share app: ‘The Velvet Spoon,’ an intimate little restaurant tucked away on a quieter street. Each second felt like an hour, each junction an eternity. My palms were damp, and I kept smoothing the fabric of my dress, though it was perfectly uncreased.

Analise. Her name tasted like a secret on my tongue. She was half my age, barely twenty-seven, and radiating an unapologetic vibrancy that both fascinated and intimidated me. We’d met a week ago, at a mutual friend’s casual get-together. There was an instant, undeniable spark, a current that arced between us the moment our eyes met across the crowded living room. She had a mischievous glint in her dark eyes, a smile that promised trouble and delight in equal measure, and a laugh that seemed to bubble up from a deep, joyful place within her. Our friends, bless their meddling hearts, had seen it too, and had subtly, then not-so-subtly, encouraged us to exchange numbers.

That exchange had opened a floodgate. For the past seven days, my phone had been an extension of Analise, buzzing with her thoughts, her jokes, and then, slowly, deliciously, her desires. We’d started with polite DMs, transitioned to playful banter, and by day three, the sexting had begun. It started innocently enough, a murmured curiosity about my evening, a hint of wanting to know more. Then it escalated, each text more explicit, more daring, more tantalizing than the last. She had a way with words, painting vivid pictures with her emojis and her descriptions, making me feel as though she was already there, tracing lines on my skin with her fingertips.

My nights had become a blur of hot sheets and racing pulses. Her words, “Tell me what you’re wearing, Maddy,” would send me to the mirror, stripping off my day clothes, feeling the cool air on my skin as I’d snap a quick, coy photo for her. Her response, “Imagine my tongue teasing its way down your stomach, stopping just where your panties begin,” would have my fingers trembling as I typed back, “Don’t just imagine, Analise. Make me feel it.”

I’d lie in bed, phone clutched in my hand, her explicit texts illuminating my face in the dark. My other hand would delve under the covers, finding my clit, already swollen and aching with need. I’d read her words, picturing her dark eyes, her full lips, her clever fingers, and fantasize about this very moment. I’d imagine her pulling my legs apart, burying her face between my thighs, the hot wetness of her mouth on me. I’d hear her breath hitch with anticipation as I’d describe what I wanted her to do, or what I was doing to myself in that very moment, her words guiding my touch. I’d come, multiple times, to the rhythm of our shared fantasies, my body shaking, desperate for the real thing.

This was it. The first time we were meeting alone, without the buffer of friends, without the safety of a screen. The air in the taxi was thick with the weight of my expectations, and the memory of those texts, still burned into my mind. I knew, with an instinctual certainty, that tonight would be different. I could feel it in my bones. And I knew something else, too – a detail she’d casually dropped in a late-night text that had sent a shiver of pure lust down my spine: she was shaved. And I, for my part, had made sure the landscape between my legs was just as smooth and welcoming.

The taxi pulled up to the restaurant, a soft glow emanating from its windows. I paid the driver, my tipsy fingers fumbling slightly with the cash, and stepped out into the cool evening air. The scent of roasted garlic and something sweet, like crème brûlée, drifted from inside. As I pushed open the heavy wooden door, she was already there, sitting at a small, candlelit table in the corner, a vision in a simple, elegant black slip dress that clung to her curves like a second skin. Her dark hair cascaded over one shoulder, catching the candlelight, and her eyes, those beautiful, mischievous eyes, sparkled as she looked up and saw me. A slow, knowing smile spread across her lips, and my breath hitched. She was even more stunning than I remembered.

“Maddy,” she breathed, standing to greet me. Her voice was lower than I remembered, a smoky caress that sent shivers down my spine.

“Analise,” I managed, my voice a little rougher than I intended.

We hugged, a brief, polite embrace that held an electricity that was anything but. Her body felt warm and firm against mine, and I could smell a hint of something clean, a little musky, and utterly intoxicating. We settled into our seats. The waiter appeared, unobtrusive, to take our drink orders.

“I’ll just have water, please,” Analise said, her eyes meeting mine, a silent acknowledgment of the fact that she was the designated driver. “And for you, Maddy?”

“A very large glass of Merlot, please,” I replied, a small, nervous laugh escaping me.

I needed the liquid courage, or perhaps, simply the rich warmth of a good red wine to settle my racing heart.

The initial small talk was almost excruciatingly polite. We discussed our day, the weather, the restaurant’s ambiance. My gaze kept drifting to her lips, to the curve of her throat, to the way the candlelight danced in her eyes. I could feel the heat radiating from her, a magnetic pull that made focusing on the merits of the artisanal bread basket nearly impossible. Then, slowly, subtly, the conversation began to shift. It started with a shared glance, a prolonged eye contact that lingered a fraction of a second too long.

“This dress… it suits you,” Analise murmured, her voice dropping to a lower register. “It looks like it would feel incredible against the skin.”

My cheeks flushed. “It’s satin,” I offered, a little breathlessly. “Very soft.”

“I can imagine,” she said, her eyes trailing down the curve of my chest, lingering for a moment on the swell of my breasts, then meeting my gaze again, hot and direct.

“You know,” she continued, leaning forward slightly, her voice barely a whisper, “I’ve been thinking about your texts all day. Especially the ones where you described… exactly what you wanted me to do to you.”

My heart hammered against my ribs.

“Oh?” I managed, my voice suddenly thready. The wine arrived, and I took a long, fortifying sip.

“Yes. The one about my tongue. About your… clitoris. And how you like it when I tease you first.”

Her words were like a physical touch, each syllable a caress. She reached across the table, her fingers brushing mine briefly, electric.

“Is that true, Maddy? Do you like to be teased?”

The polite veneer of dinner conversation shattered, replaced by an intoxicating current of raw desire.

“More than you know,” I whispered back, my eyes locked on hers. “And you, Analise? What do you like? What makes you ache?”

Her smile widened, predatory and beautiful. “I like to be worshipped, Maddy. I like a woman who knows how to use her mouth. And I like to feel a woman’s breath on my skin, right there, when she’s about to make me scream.” Her eyes dropped to my crotch, a brief, scorching glance, before returning to my face.

“Tell me, are you wearing those white underwear you teased me with in the photo earlier?”

My breath hitched. I hadn’t thought she’d remember.

“Maybe,” I whispered, a slow, wanton smile spreading across my lips.

“And are you as naked as you claimed under that dress?”

She giggled, a low, throaty sound that promised delicious secrets. “Wouldn’t you like to know?” she purred.

“This conversation… it’s getting a little too hot for a public restaurant, don’t you think?”

“I think,” I said, leaning closer, my voice barely audible, “that I’m about to explode.”

Analise took a sip of her water, her eyes never leaving mine.

“My flat isn’t far from here,” she murmured. “We could… continue this conversation there. In a much more private setting.”

A tremor ran through me. “I’d like that very much, Analise.”

We finished our meals quickly after that, the food suddenly tasteless, our appetites consumed by a different kind of hunger. The waiter brought the bill, and Analise insisted on paying.

“My treat,” she said, her fingers brushing mine again as she handed over her card. “Consider it a down payment.”

The short walk to her car was agonizing. The cool night air was a shock after the restaurant’s hothouse atmosphere, but it did little to cool the fire raging within me. She unlocked her sleek black sedan, and I practically dove into the passenger seat, my satin dress whispering around me. The moment she buckled her seatbelt and started the engine, she looked at me, her eyes dark with intent.

“Ready for a ride, Maddy?”

“More than ready,” I breathed.

She turned out of the parking lot, her movements smooth and deliberate. Almost immediately, her left hand, which wasn't on the steering wheel, slid from the gear stick and found my thigh. Her fingers, long and elegant, began to trace patterns through the satin, moving higher and higher, a slow, agonizing crawl.

“Analise,” I gasped, my voice barely a whisper, “you’re driving.”

Her smile was wicked.

“Just exploring, Maddy. Just getting acquainted.”

Her fingertips brushed the very edge of my white underwear, sending a jolt of pure pleasure through me. My hips twitched involuntarily. She knew exactly what she was doing. “Are you wet yet?” she murmured, her thumb brushing against the mound of my sex.

“Analise, please,” I pleaded, half-laughing, half-moaning. “We’ll crash the car. Wait. Just… wait until we get to your place.”

I gently, but firmly, caught her hand and held it. The restraint was almost unbearable, but the thought of finally being alone with her, with no limits, made it worth it. She sighed dramatically.

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“Fine, fine. But you owe me for this denial.” Her eyes sparkled with amusement and something deeper, something hungry.

The drive felt endless, but finally, she turned onto a quiet street and pulled into a parking spot in front of a modest, red-brick building.

“Home sweet home,” she purred, turning off the engine.

Before I could even unbuckle my seatbelt, she leaned over and kissed me, deep and hard, her tongue tangling with mine. My fingers tangled in her hair, pulling her closer, tasting the wine on her lips and the fresh, clean scent of her skin. This was real. This was happening. We practically tumbled out of the car and into her building, her hand gripping mine, tugging me along. Her flat was small, cozy, and filled with the faint scent of something earthy and sweet, like incense and old books. The lights were low, casting a soft, inviting glow.

The moment the door clicked shut behind us, she had her hands on me. Her fingers were nimble, finding the delicate straps of my satin dress, pulling them down my shoulders with expert ease. The cool fabric pooled around my feet, leaving me standing in just my white lace underwear. My breath hitched as her eyes devoured me, a slow, appreciative gaze that made my skin tingle.

“Leave those on,” she murmured, her voice thick with desire, her fingers brushing the lace at my hips. “For now.”

Then, with a fluid motion, she shed her own black dress, letting it fall to the floor with a soft sigh. She was wearing nothing but a pair of dark lace panties underneath. My eyes widened, tracing the elegant lines of her body, the gentle swell of her breasts, the flat plane of her stomach the perfect form of her vulva soft wet and inviting.

“Thirsty?” she asked, her eyes still locked on mine.

She moved to a small kitchenette tucked into the corner of the living room, pouring two glasses of red wine from a bottle already open on the counter. The clinking of glasses was the only sound in the apartment, a soft counterpoint to the frantic beating of my heart. She handed me a glass, her fingers brushing against mine, sending another jolt through me. I took a grateful sip, the rich warmth spreading through my chest. Then, she took my glass, setting it and hers carefully on a small side table. Her hands were on my waist, pulling me closer, her body pressing against mine. She lowered us both to the floor, gently laying me down on the soft rug in front of the flickering glow of a string of fairy lights.

Her eyes, dark and knowing, held mine as she leaned over me. Her lips descended, soft and warm, on my neck, trailing a path down to my collarbone, then lower, grazing my breasts through the lace of my bra, which I suddenly realized was still on. She undid the clasp with one quick, practiced movement, pulling it away. Her tongue flicked out, tracing the curve of my breast, making me arch into her.

“You taste like wine and anticipation,” she whispered, her words hot against my skin.

She licked her way down my stomach, her breath teasing me, dancing over my navel. My white panties were still there, a thin barrier that felt like a deliberate torture. Her tongue dipped lower, circling the lace, making my clit pulse with a desperate need. Then, she pulled my underwear down, slowly, deliberately, her fingers teasing the elastic, letting it ride lower and lower, revealing more and more of my wet, aching pussy. The white lace bunched around my ankles, a final tease. And then, she was there.

Her tongue, hot and wet and demanding, latched onto my already engorged clit. A gasp tore from my throat, a sound of pure, unadulterated pleasure. She ate me, hungrily, deeply, her mouth a perfect fit, her lips sucking, her tongue spiraling, swirling, driving me mad. I bucked against her, my legs splayed, my hands gripping the rug beneath me, my head thrashing from side to side. The two years of yearning exploded into a supernova of sensation. Every nerve ending in my body was alive, focused solely on the exquisite pleasure she was delivering. I cried out her name, again and again, as my body convulsed around her mouth, wave after wave of orgasm washing over me, leaving me breathless and trembling.

When she finally pulled away, I was panting, my legs shaking, my pussy throbbing. She looked up at me, her eyes shining, her lips glistening, a triumphant smile on her face.

“My turn,” I managed, my voice raspy.

I pushed her gently onto her back. Her black dress was still on the floor, somewhere. I moved between her legs, feeling her soft skin against mine. Her panties, it turned out, were lace, and already damp with her desire. I buried my face between her thighs, tasting her, inhaling her scent, then began to lick her through the sodden lace, dragging my tongue over the delicate fabric, feeling the wetness seep through, tasting her sweet arousal. She moaned, pushing her hips into my mouth, her fingers tangling in my hair. The sensation of her wetness through the lace was intoxicating, a challenge and a promise.

I pulled her panties down, slowly, savoring her gasp of anticipation. Her pussy was perfect, a delicate, pink flower, exquisitely shaved and begging for my attention. I ate her, deeply and thoroughly, mirroring her earlier ferocity, teasing her clit with my tongue, plunging deeper into her folds, determined to bring her to the same shattering climax she had brought me. She cried out, her legs wrapping around my head, her hips bucking, her body arching off the floor.

After her first orgasm, we shifted, our bodies intertwining, our legs scissoring together, our pussies rubbing, grinding, hot and wet against each other. Her mouth found mine, kissing me roughly, our tongues dancing a passionate tango. Our hands roamed, exploring every curve, every dip of each other’s bodies, fingers stroking, squeezing, teasing. We licked and tasted, mouths roaming over breasts, stomachs, inner thighs, teasing with nibbles and soft bites.

“Wait,” Analise whispered, pulling away for a moment.

She crawled to a small bedside drawer next to the sofa and pulled out a sleek, black vibrator, small enough to fit in the palm of her hand. Her eyes, filled with a delicious thrill, met mine.

“Want to play?”

My only answer was a guttural sound of assent. She turned it on, the low hum a new addition to the symphony of our pleasure. She pressed it against my clit, and I gasped, the vibrations sending me spiraling. She moved it down, tracing circles around my outer labia, then back up, teasing the edge of orgasm. I writhed beneath her, begging, pleading for more. Then, I took it from her, guiding her hand as I pressed it against her clit, watching her eyes roll back, a soft moan escaping her lips. We took turns, teasing each other, pushing each other to the brink, then pulling back, drawing out the exquisite torture until neither of us could take it anymore.

We came, again and again, a glorious cascade of orgasms, our bodies shuddering, our cries echoing in the small flat. We were a tangle of limbs and sweat and pleasure, our pussies slick and swollen, our skin burning. We lay there for a long time, intertwined, our breathing slowly returning to normal, the scent of sex heavy and sweet in the air.

I woke the next morning to the gentle light filtering through the blinds. My eyes fluttered open to find Analise watching me, her head propped on her hand, a soft, contented smile on her face. A warmth spread through me, a feeling of utter peace and belonging. But then, a distinct sensation made itself known: my pussy. It throbbed with a dull ache, a delicious soreness that spoke of a night—and morning—of intense, unbridled pleasure. It was the kind of soreness you earn, a badge of honor from a truly spectacular encounter.

“Morning, sleepyhead,” she whispered, her voice husky. She leaned in and kissed my forehead, then my lips, a soft, lingering kiss.

“Morning,” I mumbled, stretching carefully. “My… everything is a little bit sore.”

She chuckled, a low, throaty sound that sent shivers down my spine. “Good. Means we did it right.”

We spent a lazy hour showering together, then making coffee, and eventually, getting dressed. The thought of leaving still felt wrong, but I knew I had to go. She drove me home, the ride much more subdued than the frenzied journey the night before, but no less intimate. We talked, truly talked, about our lives, our dreams, the silly little things that made us laugh. The connection felt stronger, deeper than just the physical.

When she pulled up to my apartment building, she turned off the engine, her hand resting on my knee.

“I had… an incredible time, Maddy.”

“Me too, Analise. More than incredible.”

She leaned in, a soft, tender kiss, then pulled back, her eyes twinkling. “One more thing, before you go.” Her fingers, gentle, deliberate, found their way under the hem of my skirt, sliding up my thigh. Her touch was feather-light, barely there, but potent. She found my aching clit, still swollen, still sensitive, and began to massage it, slowly, gently, her thumb circling, teasing, bringing back the echoes of the night. I gasped, my head falling back against the headrest, a soft moan escaping my lips. My pussy, still tender, responded immediately, a fresh wave of wetness blooming between my legs. She knew exactly what I needed, a soft, tender goodbye. She continued to masturbate me, her fingers working their magic until I was whimpering, on the verge of another climax.

And just as I was about to tip over, she pulled her hand away, leaving me flushed and aching and deliciously frustrated. “There,” she whispered, a triumphant smirk playing on her lips.

“Something to remember me by.”

Then, her eyes dropped to my crotch, a hungry glint in them. “One more thing,” she said, her voice dropping to a low purr. “Those white panties. Can I… have them? As a gift?”

My breath hitched. The request was so simple, so intimate, so perfectly Analise. I felt a surge of warmth, a blush spreading across my cheeks. They were still wet, still damp with my come from the night and her recent touch. Without a word, I shifted in the seat, carefully pulling up my skirt. My hands trembled slightly as I hooked my thumbs into the delicate lace of my underwear. Slowly, deliberately, I peeled them down, past my hips, over my thighs, until they were a small, wet bundle in my hand. The warmth of my sex, exposed to the cool air, was a delicious sensation. I held them out to her. She took them, her fingers brushing mine, her eyes burning into mine. She brought them to her nose, inhaling deeply, a slow, satisfied smile spreading across her lips. The lace was still glistening, a tangible reminder of the passionate night.

“Perfect,” she murmured, tucking them into her pocket. “I’ll be in touch, Maddy.”

I watched her drive away, the small, wet bundle of my panties now hers, a secret between us. My pussy throbbed, still aching from her touch. I stepped out of the car, the cool air hitting my bare legs, and walked into my apartment, a soft, contented smile on my face. The two-year drought was irrevocably, spectacularly over. And something told me, this was just the beginning.

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Written by Madeline_Miles
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