older woman

Madeline’s First Encounter

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I took a deep breath, my fingers hovering over the screen of my phone. The exclusive dating app, “Cougar’s Den,” gleamed back at me, its sleek interface promising adventure and indulgence. At fifty, I, Madeline, had never felt more alive. My brown hair, now streaked with silver, framed my face, and my green eyes sparkled with anticipation. I was a woman who knew what she wanted: younger men, passionate encounters, and no strings attached. The plumber incident had only whetted my appetite, and now I was ready for more.

The app was a playground for cougars like me, and I swiped with purpose, my C-cup breasts rising and falling with each exhale. I paused on a profile that made my heart skip a beat. His name was Gary, a college student with a head full of golden hair and eyes as blue as the summer sky. His bio was shy but eager: “Curious about older women. Looking for someone to show me the ropes.” I smirked, my fingers swiping right without hesitation.

Minutes later, a notification pinged. Gary had matched with me. My pulse quickened as I opened the chat. His first message was simple: “Hi, Madeline. You’re stunning.” I chuckled, typing back, “Why, thank you, Gary. You’re quite the looker yourself.” The conversation flowed easily, his youthful enthusiasm balancing my seasoned confidence. We exchanged a few messages before I suggested meeting in person. “There’s a chic little café downtown,” I wrote. “How about tomorrow afternoon?”

“I’d love to,” he replied almost instantly.

The next day, I dressed to impress. A form-fitting black dress hugged my shapely figure, and a pair of red heels added a touch of boldness. My lips were painted a deep crimson, and a hint of perfume lingered in the air. I arrived at the café early, securing a corner table where I could observe the entrance. My heart raced as I sipped my latte, anticipation building with every passing minute.

Then, he walked in. Gary was even more breathtaking in person. His golden hair fell perfectly across his forehead, and his blue eyes widened as he spotted me. He approached with a nervous smile, his lanky frame exuding youthful charm. “Madeline,” he said, his voice soft but steady. “You’re even more beautiful in person.”

“Why, thank you, Gary,” I purred, gesturing to the seat across from me. “Please, sit.”

As we talked, I could feel his gaze drifting to my cleavage, subtly exposed by the neckline of my dress. I leaned forward slightly, giving him a better view, and watched as his cheeks flushed. He was shy, but his desire was palpable. I loved that—the mix of innocence and eagerness.

“So, Gary,” I began, my voice low and sultry. “What is it about older women that intrigues you?”

He hesitated, his fingers fidgeting with the edge of his napkin. “I don’t know,” he admitted. “There’s just something about the confidence, the experience… it’s intoxicating.”

I smiled, leaning back in my chair. “Experience can be a wonderful teacher, Gary. Are you ready to learn?”

His eyes met mine, and for a moment, the café faded away. “Yes,” he whispered.

I paid the bill, standing gracefully. “Shall we?” I extended my hand, and he took it, his fingers trembling slightly. I led him to my car, a sleek black sedan that reflected his awe. As we drove to my penthouse apartment, the tension between us thickened. I could feel his eyes on me, hungry yet respectful.

Once inside, I offered him a drink, but he declined, his nerves getting the better of him. I smiled, stepping closer. “Gary,” I said, my voice barely above a whisper. “There’s no need to be nervous. I’m here to make you comfortable.”

He nodded, his breath coming quicker. I placed a hand on his chest, feeling the rapid beat of his heart beneath his shirt. “Do you trust me?” I asked.

“Yes,” he replied without hesitation.

I stepped even closer, my body brushing against his. “Good,” I murmured, reaching up to undo the top button of his shirt. “Because I’m going to show you things you’ve only dreamed of.”

His eyes widened as I slowly unbuttoned his shirt, revealing his smooth chest. I traced my fingers along his collarbone, down to his pecs, savoring his youthful firmness. He shivered under my touch, his breath hitching as I pressed my body against his. “Madeline,” he groaned, his hands hovering at his sides, unsure where to touch me.

“It’s okay, Gary,” I whispered, guiding his hands to my hips. “Touch me. Feel how much I want you.”

He hesitated for a moment before his hands slid up my dress, his fingers grazing the lace of my thigh-high stockings. I moaned softly, pressing my lips to his neck, my breath hot against his skin. “You’re doing so well,” I murmured, nipping at his earlobe. “Now, take off my dress.”

His fingers trembled as he pulled the fabric down my shoulders, the dress pooling at my feet. I stood before him in nothing but my lingerie—a black lace bra that accentuated my C-cup breasts and matching panties that hugged my curves. His eyes devoured me, his desire undeniable.

“You’re so beautiful,” he breathed, his hands reaching out to cup my breasts.

“Thank you, Gary,” I said, stepping back slightly to undo his belt. “Now, it’s my turn to explore.”

I pushed his pants down, revealing his boxers, already tented with his arousal. I smirked, kneeling before him to trace my fingers along the outline of his cock. “You’re so hard for me,” I teased, my voice dripping with lust. “Does my older body excite you, Gary?”

“Yes,” he groaned, his hands tangling in my hair. “Please, Madeline.”

I hooked my fingers into his boxers and pulled them down, his cock springing free. It was thick and long, pulsing with need. I licked my lips, looking up at him through my lashes. “Such a beautiful cock,” I purred, wrapping my hand around his shaft. “Do you want me to taste it?”

“Yes, please,” he begged, his voice cracking.

I leaned forward, taking him into my mouth, my lips sliding down his length. He gasped, his hands gripping my shoulders as I sucked him deep, my tongue swirling around the head. I hummed, the vibrations sending shivers through him. “Fuck, Madeline,” he moaned. “That feels so good.”

I smiled around his cock, pulling back to tease the tip with my tongue. “Do you like that, Gary?” I asked, my voice husky. “Do you like my mouth on your cock?”

“Yes, yes, yes,” he panted, his hips bucking slightly.

I chuckled, taking him back into my mouth, my hand stroking the base in rhythm. I sucked him hard, my cheeks hollowing as I swallowed him down. He groaned, his fingers tightening in my hair. “Madeline, I’m close,” he warned.

“Cum for me, Gary,” I urged, quickening my pace. “Fill my mouth with your hot cum.”

He cried out, his body tensing as he erupted, his cum shooting down my throat. I swallowed greedily, milking him until he was spent. When I finally pulled back, he was trembling, his eyes glazed with pleasure.

I stood, pressing a gentle kiss to his lips. “That was just the beginning, Gary,” I whispered, leading him to the bedroom. “Now, it’s my turn.”

The bedroom was dimly lit, the air thick with anticipation. I pushed him gently onto the bed, his eyes wide as I climbed on top of him. “Madeline,” he breathed, his hands roaming over my body.

“Shh,” I soothed, capturing his lips in a deep kiss. I ground my hips against his, my pussy aching for him. “I want you inside me, Gary. Now.”

He nodded, his hands guiding me as I positioned myself over his cock. I lowered myself slowly, his thickness stretching me deliciously. “Fuck,” I moaned, my head falling back as I took him all the way in. “You feel so good.”

He groaned, his hands gripping my hips as I began to ride him, my breasts bouncing with each thrust. “Madeline, you’re incredible,” he panted, his eyes dark with desire.

I smiled, leaning forward to kiss him, our bodies moving in perfect sync. I rode him harder, my pussy clenching around his cock as pleasure built within me. “Gary,” I gasped. “I’m close.”

“Cum for me, Madeline,” he urged, his hands squeezing my ass. “Let me feel you squeeze my cock.”

His words sent me over the edge. I cried out, my body shaking as I came, my pussy flooding around him. He thrust up into me, his own release following moments later, his cock pulsing deep inside me.

We lay tangled together, our breaths slowly returning to normal. I pressed a kiss to his chest, my fingers tracing lazy patterns on his skin. *”That was…” he began, his voice trailing off.

“Incredible,” I finished for him, smiling. “You were incredible, Gary.”

He blushed, pulling me closer. “Thank you for showing me… everything.”

I chuckled, running my fingers through his golden hair. “Anytime, Gary. Anytime.”

As we lay there, the city lights twinkling outside the window, I felt a deep satisfaction. Gary had been the perfect cub—eager, passionate, and utterly enchanting. But as much as I enjoyed our encounter, I knew this was just the beginning. The world of younger men was vast, and I was ready to explore every inch of it.

For now, though, I was content to savor the moment, my body still buzzing with the aftermath of our passion. Gary’s hand rested on my hip, his touch gentle and reverent. I smiled, closing my eyes, knowing that this was exactly where I was meant to be.

The night deepened, and as sleep began to pull me under, I whispered, “Goodnight, Gary.”

“Goodnight, Madeline,” he replied, his voice soft and full of wonder.

And in that moment, I knew that this was just the first chapter of many steamy adventures to come.

The Neighbor’s Son

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I stood in my dimly lit living room, the curtains drawn to keep prying eyes at bay. The unmarked box sat on the coffee table, its contents now scattered across the plush carpet. Vibrators of various shapes and sizes lay beside dildos, their smooth surfaces glinting under the soft glow of the lamp. My heart raced as I picked up a sleek, silver bullet vibrator, its hum buzzing softly in my hand. I couldn’t shake the image of Shane, my neighbor’s son, from my mind. His rebellious smirk, his lean, muscular frame—he was the last person I expected to catch me in such a compromising position.

I had been so absorbed in my own pleasure, lost in the throes of orgasm, that I hadn’t heard the creak of the back door or the soft footsteps approaching. But there he was, standing in the doorway, his dark eyes wide with surprise. For a moment, neither of us spoke. The air crackled with tension as I stood there, half-naked, my cheeks flushed with embarrassment and desire.

“Miss Meredith,” Shane finally said, his voice low and husky. “I, uh, I didn’t mean to interrupt.”

I swallowed hard, my pulse pounding in my ears. “Shane, I—”

“It’s okay,” he cut in, stepping closer. “I won’t tell anyone.”

His words hung in the air, heavy with unspoken implications. I felt a flush creep down my chest, settling between my thighs. Shane’s gaze lingered on the toys scattered around me, and I saw the hunger in his eyes. He wasn’t just a rebellious teenager; he was a man now, and he wanted me.

“You like these, huh?” he asked, his voice dropping to a whisper.

I nodded, unable to find my voice. Shane’s presence was intoxicating, his youthful energy filling the room. He knelt in front of me, his hands brushing against my thighs as he picked up a vibrator. “Mind if I watch?”

My breath hitched. “Shane, you shouldn’t—”

“I want to,” he insisted, his eyes locking onto mine. “Please.”

The word was a plea, a command, and a promise all at once. My resistance crumbled. I sank back onto the couch, my legs parting slightly as I gave him silent permission. Shane’s gaze devoured me, his lips curling into a mischievous smile. He sat cross-legged on the floor, his attention fixed on my body as I reached for the bullet vibrator again.

I pressed it against my clit, the vibrations sending shivers through me. Shane’s eyes darkened, his breath quickening as he watched me. I moaned softly, my fingers tracing patterns on my stomach, teasing the edge of my panties. “Do you like that?” he murmured, his voice thick with desire.

“Yes,” I whispered, my cheeks burning. “Oh, yes.”

He leaned closer, his hand reaching out to brush against my thigh. “Let me help.”

Before I could protest, Shane’s fingers were sliding beneath the waistband of my panties, his touch electric against my sensitive skin. I gasped, my body arching toward him as he traced the curve of my hip. “Shane, what are you doing?”

“What do you think?” he replied, his lips brushing against my ear. “I’m making you feel good.”

His words sent a jolt of desire through me. I was a woman in her fifties, and here was this young man, barely out of his teens, touching me with a confidence that belied his age. It was wrong, so wrong, but it felt so right. I closed my eyes, surrendering to the sensation of his fingers sliding between my folds, his touch firm yet gentle.

“You’re so wet,” he murmured, his breath hot against my neck. “You like this, don’t you?”

“Yes,” I moaned, my head falling back against the couch. “Oh, Shane, yes.”

He grinned, his fingers delving deeper, his thumb pressing against my clit. The vibrator buzzed against my skin, the combination of his touch and the toy’s vibrations pushing me closer to the edge. I was drowning in pleasure, my body on fire as Shane explored me with a hunger that matched my own.

“Tell me what you want,” he whispered, his lips brushing against my collarbone. “Tell me, Mrs. Meredith.”

“I want you,” I gasped, my voice hoarse with need. “I want you to touch me, to make me feel good.”

Shane’s eyes flashed with triumph. He leaned forward, his lips capturing mine in a kiss that was both tender and fierce. His tongue slid into my mouth, tasting me, claiming me. I moaned into the kiss, my hands tangling in his hair as he deepened the embrace.

He pulled back, his breath ragged as he trailed kisses down my neck, his hands roaming over my body. “You’re so beautiful,” he murmured, his lips brushing against my breast. “So fucking beautiful.”

His words sent a rush of heat through me. I was no longer just Meredith, the mature woman next door. I was his desire, his fantasy, and he was mine. Shane’s hands cupped my breasts, his thumbs teasing my nipples until they pebbled beneath his touch. I arched into him, my moans filling the room as he lavished attention on my body.

“Do you want more?” he asked, his voice a low growl.

“Yes,” I whispered, my body trembling with anticipation. “Oh, yes.”

Shane reached for one of the dildos, a sleek, black one that seemed to pulse with promise. He positioned himself between my legs, his eyes never leaving mine as he guided the tip to my entrance. “Ready?”

I nodded, my breath coming in short gasps. Shane pushed the dildo inside me, slow and steady, his fingers curling around the base as he watched my reaction. The sensation was overwhelming, the fullness of the toy stretching me in ways the vibrator couldn’t.

“Fuck,” he muttered, his voice thick with awe. “You’re so tight.”

I moaned, my hips rising to meet his movements as he began to thrust the dildo in and out of me. The rhythm was hypnotic, each stroke sending waves of pleasure through my body. Shane leaned forward, his lips brushing against my ear as he whispered filthy words, his hands roaming over my skin.

“You like this, don’t you?” he growled. “You like being filled up by this big cock.”

“Yes,” I panted, my body on the brink of orgasm. “Oh, Shane, yes.”

He quickened his pace, his fingers digging into my hips as he fucked me with the dildo. The room was filled with the sounds of our passion—my moans, his grunts, the slick wetness of my body responding to his touch. I was teetering on the edge, my orgasm building with each thrust.

“Come for me,” Shane commanded, his voice a harsh whisper. “Let me see you come.”

His words were the final push I needed. My body convulsed, my cries echoing through the room as I surrendered to the most intense orgasm of my life. Shane watched, his eyes dark with desire, as my body shook with pleasure. When the last shudders subsided, he leaned forward, his lips pressing a tender kiss to my forehead.

“That was fucking amazing,” he murmured, his breath warm against my skin.

I smiled, my heart still racing as I pulled him into a hug. “It was,” I agreed, my voice soft. “But Shane, we can’t—”

“Shh,” he interrupted, his fingers brushing against my lips. “Don’t think about it. Just feel.”

And so I did. I let go of my inhibitions, my worries, and my age. In that moment, I was just a woman, lost in the arms of a man who desired me, who made me feel alive. Shane’s lips found mine again, his kiss hungry and demanding. I responded with equal fervor, my hands roaming over his body as I explored him with the same passion he had shown me.

He stood, pulling me to my feet, his hands sliding down to grip my ass. “Let’s take this to the bedroom,” he murmured, his voice a low rumble.

I nodded, my body still buzzing with pleasure as I followed him down the hall. The bedroom was a blur of soft light and tangled sheets, the air thick with anticipation. Shane pushed me gently onto the bed, his eyes raking over my body with unbridled desire.

“You’re so fucking sexy,” he growled, his hands tracing the curves of my body. “I’ve wanted this for so long.”

His words sent a rush of heat through me. I reached for him, my fingers tracing the contours of his chest as I pulled him closer. Shane’s lips crashed against mine, his kiss fierce and possessive. He moved with the confidence of a man who knew what he wanted, his hands roaming over my body with a hunger that left me breathless.

He pushed my legs apart, his fingers sliding between my thighs as he teased my already sensitive flesh. “You’re still wet,” he murmured, his voice a low growl. “Still ready for me.”

“Yes,” I whispered, my body arching toward him. “Oh, yes.”

Shane reached for another toy, a strap-on this time, the dildo thick and veined. My eyes widened as he fastened the straps around his waist, the sight of him wearing it sending a jolt of desire through me. “You like this?” he asked, his voice a challenge.

“Yes,” I breathed, my pulse pounding in my ears. “Oh, Shane, yes.”

He positioned himself between my legs, his hands gripping my hips as he guided the tip of the dildo to my entrance. “Ready for me?”

I nodded, my body trembling with anticipation. Shane thrust into me, slow and steady, the dildo filling me in a way that left me gasping for breath. He moved with a rhythm that was both tender and fierce, his hips snapping forward as he fucked me with a passion that matched my own.

“Fuck,” he groaned, his voice thick with desire. “You feel so good.”

“Shane,” I moaned, my nails digging into his shoulders as I met his thrusts. “Oh, Shane, don’t stop.”

He quickened his pace, his body moving with a primal urgency as he drove the dildo deep inside me. The room was filled with the sounds of our passion—the slick wetness of our bodies, the creak of the bed, our moans and cries echoing through the space.

“Come for me,” Shane commanded, his voice a harsh whisper. “Let me feel you come around my cock.”

His words were my undoing. My body convulsed, my orgasm crashing over me like a wave as I cried out his name. Shane followed, his body stiffening as he thrust one final time, his release echoing mine.

We lay tangled in the sheets, our breaths ragged as we came down from the high. Shane’s fingers traced patterns on my skin, his touch tender and reverent. “That was…” he began, his voice trailing off.

“Incredible,” I finished, my smile soft. “But Shane, we can’t—”

“Shh,” he interrupted, his lips brushing against my forehead. “Don’t think about it. Just feel.”

And so I did. I let go of my worries, my inhibitions, and my age. In that moment, I was just a woman, lost in the arms of a man who desired me, who made me feel alive. Shane’s lips found mine again, his kiss tender and sweet.

“Thank you,” he murmured, his voice soft. “For letting me be a part of this.”

I smiled, my heart full as I pulled him closer. “Thank you,” I replied, my voice just as soft. “For making me feel desired.”

We lay there, wrapped in each other’s arms, the world outside forgotten. The toys were still scattered around us, evidence of our passion, but in that moment, they were just props. What mattered was the connection between us, the forbidden desire that had brought us together.

As the night deepened, Shane’s breathing slowed, his body relaxing against mine. I stroked his hair, my heart full as I watched him sleep. What we had done was wrong, so wrong, but it felt so right. And as I drifted off to sleep, I knew that this was just the beginning. Our secret encounters would continue, each one pushing the boundaries of our desire, each one reminding me that age was just a number, and passion knew no bounds.

The Leap of Faith

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I shifted uncomfortably in my seat, the leather creaking beneath me as I gathered the courage to speak. Dr. Ava Collins, my psychologist, sat across from me, her hazel eyes warm and inviting behind her glasses. Her shoulder-length brown hair framed her face, and her intelligent gaze seemed to see right through me. At 54, she had a presence that was both calming and commanding, her great body and C cup breasts hinting at a confidence that made me feel safe yet intimidated. The office was cozy, with soft lighting and the faint scent of lavender, but my mind was anything but at ease.

“Carter,” she began, her voice steady and kind, “you’ve been quiet today. Is there something on your mind?”

I took a deep breath, my heart pounding in my chest. This was it. I had to say it. “Yeah, there is,” I admitted, my voice barely above a whisper. “It’s… it’s about my girlfriend. And me. There’s something I’ve been wanting to try, but I’m scared to bring it up.”

Dr. Collins leaned forward, her elbows resting on her desk, her fingers intertwined. “I’m here to listen, Carter. You know that. What is it?”

I swallowed hard, my throat dry. “It’s about… pegging. I’ve been fantasizing about my girlfriend using a strap-on on me. But I’m terrified of how she’ll react. I mean, it’s not exactly a typical thing, right?”

She nodded slowly, her expression neutral but understanding. “Sexual exploration is a deeply personal journey, Carter. It’s natural to feel hesitant about sharing your desires, especially when they’re outside societal norms. But communication is key in any relationship. Have you considered just… asking her?”

I laughed nervously, running a hand through my hair. “Easier said than done, Doc. I mean, what if she thinks I’m weird? Or worse, what if she laughs at me? I’ve been using prostate massage toys on my own sometimes, and it feels amazing, but sharing that with her? It’s a whole different ballgame.”

Dr. Collins smiled gently, her hazel eyes softening. “Carter, the only way to know how she’ll react is to ask. It might feel scary, but think about the potential for growth—both for you and for your relationship. And remember, if she’s the right person for you, she’ll be open to exploring your desires with you.”

Her words resonated with me, but the fear still lingered. “I guess you’re right,” I mumbled, more to myself than to her. “But what if she says no? What if I ruin everything by even bringing it up?”

“Carter,” she said, her voice firm yet compassionate, “a relationship built on honesty and trust can withstand these conversations. If she’s not open to it, that’s her choice, but at least you’ll know. And if she is… well, think of the pleasure you could share.”

I sighed, leaning back in my chair. “I know you’re right. It’s just… it’s hard to put myself out there like that.”

Dr. Collins stood and walked around her desk, sitting on the edge of it, closer to me. Her presence was grounding, her scent—a mix of lavender and something uniquely her—filling my senses. “Carter, I’ve been a psychologist for decades, and I’ve seen countless people struggle with this exact fear. But I’ve also seen the incredible things that happen when they take that leap. You’re not alone in this.”

Her words gave me a sliver of courage. “Okay,” I said, nodding slowly. “I’ll think about it. Maybe… maybe I’ll bring it up with her.”

She smiled, her eyes crinkling at the corners. “That’s all I’m asking. Take your time, but don’t let fear hold you back from something that could bring you both closer.”

The days that followed were a blur of anxiety and anticipation. Dr. Collins’ words echoed in my mind, urging me to take the leap. Finally, one evening, as my girlfriend and I lounged on the couch, I decided it was time. My heart raced as I cleared my throat, my palms sweating.

“Hey,” I began, my voice unsteady, “can we talk about something?”

She turned to me, her brow furrowed slightly. “Of course. What’s up?”

I took a deep breath, steeling myself. “There’s something I’ve been wanting to try, sexually. It’s… it’s a bit out there, and I’m scared to even bring it up, but I trust you, and I want to be honest with you.”

Her expression softened, and she took my hand in hers. “You can tell me anything, babe. What is it?”

I paused, my throat tight. “I’ve been fantasizing about… about you using a strap-on on me. I know it’s not typical, and I’ve been using prostate massage toys on my own, but I’d really like to experience it with you. If you’re willing, of course.”

The room fell silent, the weight of my words hanging in the air. I held my breath, my heart pounding in my chest, terrified of her reaction.

Then, to my astonishment, she smiled—a slow, knowing smile that sent a jolt of excitement through me. “You’ve been holding onto that, huh?” she teased, her voice gentle. “I had no idea, but… I’m flattered you trust me enough to share it.”

Relief washed over me, but it was quickly replaced by a surge of hope. “Really? You’re not… weirded out?”

She laughed, a warm, infectious sound. “Not at all. In fact, I’ve always had a bit of a dominant side, and the idea of taking control like that… it’s kind of hot.”

My breath caught in my throat. “You’re serious?”

She nodded, her eyes sparkling with mischief. “Dead serious. I’ve never done it before, but I’m more than willing to explore it with you. It’s about pleasure, right? And if it brings you joy, I’m all for it.”

I felt a rush of gratitude and desire, my fear melting away. “Thank you,” I whispered, pulling her into a tight hug. “I was so scared to bring it up, but I’m glad I did.”

She kissed my forehead, her lips soft against my skin. “Communication is everything, babe. And now that we’re on the same page, let’s make this happen.”

The following weekend, we set aside time to explore this new territory. I had purchased a strap-on harness and a realistic dildo, my heart racing as I laid them out on the bed. My girlfriend entered the room, her eyes widening at the sight.

“You really went all out, huh?” she teased, her voice laced with amusement.

I shrugged, feeling a mix of excitement and nervousness. “I wanted it to be perfect for us.”

She smiled, walking over to me and taking my hands in hers. “It already is perfect, because we’re doing this together. But before we start, I want you to know that I’m in control tonight. You’re going to submit to me, and I’m going to give you the pleasure you’ve been craving.”

Her words sent a shiver down my spine, my body already responding to her dominance. “Yes, ma’am,” I murmured, my voice submissive.

She guided me to the bed, pushing me gently onto my back. “Stay there,” she commanded, her tone firm yet playful.

I watched as she undressed, her body confident and alluring. She slipped into the harness, adjusting the straps until the dildo sat snugly against her hips. The sight of her standing there, her hazel eyes smoldering with desire, made my breath catch in my throat.

“You like what you see?” she asked, her voice low and husky.

I nodded, unable to speak, my cock already hardening at the sight of her.

She climbed onto the bed, straddling my chest, her weight pressing me into the mattress. “Good,” she purred, leaning down to kiss me deeply. Her lips were soft, her tongue teasing mine as she ground her hips against me, the dildo pressing firmly against my stomach.

“Turn over,” she whispered against my lips, her breath warm. “It’s time for your lesson in submission.”

I did as she commanded, flipping onto my stomach, my heart racing with anticipation. She positioned herself behind me, her hands roaming over my body, her touch both gentle and commanding.

“Relax,” she murmured, her lips brushing against my ear. “This is for your pleasure, and I’m going to make sure you enjoy every second of it.”

I felt her fingers trace the curve of my hips, her touch sending sparks of desire through me. She spread my cheeks, exposing my hole, and I shivered as her breath ghosted over my sensitive skin.

“You’re already wet,” she observed, her voice laced with satisfaction. “Eager, aren’t we?”

I moaned softly, my body trembling with anticipation. “Please,” I whispered, my voice desperate.

She chuckled, her fingers teasing my entrance, circling it slowly before pressing a single digit inside. I gasped at the intrusion, my body tightening around her.

“So tight,” she murmured, her voice thick with desire. “But we’re not rushing this. I want you to feel every inch of me.”

She withdrew her finger, replacing it with the tip of the dildo. I felt it press against me, the girth stretching me open, and I whimpered, my body arching slightly.

“Shh,” she soothed, her hand resting on my lower back. “Relax for me, baby. Let me in.”

I took a deep breath, focusing on her words, and slowly, she pushed the dildo inside me. The sensation was overwhelming—a mix of fullness and pleasure that made my toes curl.

“How does that feel?” she asked, her voice gentle but commanding.

“So good,” I moaned, my voice hoarse. “More, please.”

She smiled, her lips brushing against my shoulder as she began to move, thrusting slowly at first, giving me time to adjust to the size of the dildo. With each stroke, she went deeper, her hips snapping against my ass, the harness creaking with the force of her movements.

“You’re taking it so well,” she praised, her voice laced with pride. “Such a good boy for me.”

Her words sent a rush of pleasure through me, my body responding to her dominance. I felt the dildo hit my prostate, and I cried out, my cock leaking pre-cum onto the bed.

“That’s it,” she encouraged, her pace quickening. “Let go for me, baby. Feel every sensation.”

I moaned, my body tense with pleasure, my muscles quivering as she reamed my ass with the strap-on. The sensation was indescribable—a mix of fullness, pressure, and release that had me teetering on the edge of orgasm.

“Please,” I begged, my voice broken. “I’m close.”

She chuckled, her breath hot against my ear. “Not yet, baby. I’m not done with you.”

She reached around, her hand wrapping around my cock, stroking me in time with her thrusts. The combination of sensations was too much, my body overwhelmed with pleasure.

“Ava,” I gasped, my voice a plea. “I can’t hold on much longer.”

“Then don’t,” she commanded, her voice firm. “Let go for me, Carter. Give me your orgasm.”

Her words were my undoing. With a cry of release, I came, my body shaking as waves of pleasure washed over me. My cum shot onto the bed, my cock throbbing in her hand as she milked every last drop from me.

She continued to thrust, the dildo filling me completely, her dominance absolute. “That’s it,” she murmured, her voice satisfied. “Feel how good it is to surrender to me.”

I moaned, my body boneless, my mind reeling from the intensity of the experience. She slowed her movements, eventually withdrawing the dildo, leaving me feeling empty and satisfied.

She collapsed beside me, pulling me into her arms, her lips pressing against my sweat-dampened hair. “You did so well, baby,” she whispered, her voice filled with affection. “I’m proud of you for sharing this with me.”

I smiled, my heart full, my body still buzzing with pleasure. “Thank you for being so open to it. It meant the world to me.”

She kissed me softly, her hazel eyes meeting mine. “This is just the beginning, Carter. We’ve only scratched the surface of what we can explore together.”

I nodded, my excitement building at the thought of what the future held. “I can’t wait to see where this takes us.”

As we lay there, entwined in each other’s arms, I felt a sense of peace and fulfillment I hadn’t known was possible. Taking that leap of faith had been terrifying, but the reward—the pleasure, the connection, the trust—was worth every moment of fear. And as I drifted off to sleep, with Ava’s steady heartbeat lulling me into dreams, I knew that this was just the first chapter of our journey into the depths of desire and dominance.

Unexpected Caller

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I stared at the screen, my heart pounding in my chest. The cursor blinked mockingly, waiting for me to input the payment details. My fingers hovered over the keypad, trembling slightly. It couldn’t be. But the address was right there, staring back at me in black and white. 123 Elm Street. Tommy’s place. My nineteen-year-old neighbor with the lazy grin and jeans that hugged his ass like a second skin. What the hell was he doing calling my phone sex line?

I’d started this whole thing as a last resort. Desperation had driven me to it. The bills were piling up, and my job at the bookstore wasn’t cutting it. I’d seen an ad online, promising easy money for women with “a voice that could seduce.” I’d laughed at first, but then I’d thought about it. I’d always been told I had a husky voice, a voice that could make men melt. Why not use it?

The training had been surprisingly thorough. They’d taught me how to modulate my tone, how to whisper fantasies into the void, how to make strangers on the other end of the line believe I was everything they’d ever wanted. I’d been good at it, too. Maybe too good.

But this… this was different. This was Tommy. The boy who mowed my lawn sometimes, the one who always flirted shamelessly, his eyes lingering on my cleavage a little too long. The one who made me feel things I hadn’t felt in years.

My finger twitched towards the “end call” button. I should hang up. Pretend this never happened. But curiosity, that damnable, insatiable curiosity, held me back. What did he want? What kind of fantasies did a boy like Tommy have?

Taking a deep breath, I steadied my voice. “Hello, darling,” I purred, my usual professional tone slipping into something more personal, more dangerous. “Tell me, what brings you to my line tonight?”

There was a pause, then a nervous chuckle. “Uh, hey. I didn’t think it’d actually be… someone like you.”

Someone like me? What did that mean? I bit my lip, a thrill coursing through me. “Someone like me? And what kind of someone is that, sweetheart?”

“Someone… experienced,” he said, his voice dropping to a whisper. “Someone who knows what she’s doing.”

Experienced. The word hung in the air between us, heavy with implication. I leaned back in my chair, crossing my legs. My silk robe fell open slightly, revealing a hint of lace. I wasn’t on camera, but the act of seduction was as much for me as it was for him.

“Oh, I know exactly what I’m doing,” I murmured, letting my voice drop to a sultry growl. “Now, tell me, what are you looking for tonight? What do you need from me?”

Another pause, longer this time. I could almost hear him squirming on the other end. “I… I want to be dominated,” he blurted out, his voice cracking slightly. “I want you to tell me what to do.”

Dominated. Interesting. I’d played the role of the dominatrix before, but never with someone I knew. Never with someone so young, so close to home. The taboo of it sent a shiver down my spine.

“Is that so?” I drawled, letting a hint of amusement creep into my voice. “And what makes you think you can handle me, sweetheart? I’m not just any woman, you know.”

“I… I know,” he stammered. “That’s why I called. I’ve seen you, around the building. You’re… you’re beautiful. And I know you’re older, but that just makes it hotter. You’re so confident, so in control.”

Older. The word stung, but only for a moment. He was right, of course. I was older. But I was also experienced, and right now, that was a weapon I could wield with deadly precision.

“Flattery will get you everywhere, darling,” I purred, leaning forward, my breasts straining against the silk. “But talk is cheap. Are you ready to put your money where your mouth is?”

“Yes,” he breathed, his voice thick with desire. “Anything. Just tell me what to do.”

I smiled, a slow, predatory smile. This was going to be fun.

“Alright, Tommy,” I said, letting his name roll off my tongue like a promise. “First things first. I want you to stand up. Slowly. And tell me what you’re wearing.”

There was a rustling sound, then the creak of a chair. “I’m… I’m wearing jeans and a t-shirt,” he said, his voice shaking slightly.

“Jeans, hmm?” I murmured, picturing him in my mind’s eye. “Tight ones, I hope. I like a man who takes care of his body.”

“They’re… they’re pretty tight,” he admitted, a hint of pride creeping into his voice.

“Good boy,” I cooed. “Now, I want you to unbutton your jeans. Slowly. And tell me how it feels.”

There was a long pause, then the sound of fabric sliding against skin. “It’s… it’s hot,” he whispered, his voice hoarse with desire. “I can feel the air on my skin.”

“That’s it,” I encouraged, my voice low and hypnotic. “Let the air caress you. Imagine it’s my breath, teasing you, tantalizing you.”

“Oh God,” he moaned, his voice cracking. “That’s… that’s so hot.”

I smiled, a wicked gleam in my eye. This was too easy. Too delicious. “Now, Tommy, I want you to slide your hand inside your jeans. Slowly. And tell me what you feel.”

Another pause, then a sharp intake of breath. “I… I can feel myself,” he stammered, his voice barely above a whisper. “It’s… it’s hard.”

“Hard for me, darling?” I purred, leaning back in my chair, my robe falling open further, revealing the swell of my breasts. “Tell me, how hard are you?”

“So hard,” he groaned, his voice thick with need. “I’ve never been this hard before.”

“Good boy,” I repeated, my voice dripping with approval. “Now, I want you to stroke yourself. Slowly. And tell me how it feels.”

The line went silent except for the sound of his ragged breathing. Then, “It’s… it’s amazing. I can feel my cock throbbing in my hand. It’s so big, so hard.”

“Big, hmm?” I murmured, a smile playing on my lips. “I like a man with a big cock. Makes me wonder what else you’ve got going for you.”

“I… I don’t know,” he panted, his voice desperate. “Just tell me what to do. I’ll do anything.”

Anything. The word hung in the air, heavy with possibility. I leaned forward, my breasts spilling out of my robe, my nipples tight with arousal. “Anything, hmm? Even if it’s a little… taboo?”

“Yes,” he whispered, his voice barely audible. “Anything.”

I smiled, a slow, dangerous smile. “Alright, Tommy. Here’s what I want you to do. I want you to go to your window. The one that faces my apartment. And I want you to stroke yourself while you watch me.”

There was a sharp intake of breath, then a frantic, “You can see me?”

“Oh, I can see you,” I purred, standing up, my robe falling to the floor. I was naked now, my body on full display. “And I want you to watch me, too. Watch me touch myself while you touch yourself. Let’s see who can make the other one cum first.”

“Oh fuck,” he moaned, his voice breaking. “I’m already so close.”

“Not yet, darling,” I teased, walking towards my own window, the sheer curtains billowing slightly in the breeze. “We’re just getting started.”

I could see his silhouette now, a dark shape against the glass. He was stroking himself furiously, his movements desperate, needy. I smiled, a wicked gleam in my eye, and began to touch myself, my fingers tracing slow, deliberate circles around my clit.

Valentine’s Delivery Surprise

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I had given up on the idea of finding love, especially on Valentine’s Day. At my age, 48, I knew the chances of meeting someone special were slim, so I decided to indulge in a little self-care instead. I ordered a delicious meal from a local restaurant, a fancy three-course dinner for one. It was my way of treating myself on a day that seemed to be all about couples.

As the snow began to fall outside, creating a romantic winter wonderland, I settled in for the evening, lighting a fire in the fireplace to chase away the chill. The soft crackling of the flames provided a cozy backdrop to my solo celebration. Little did I know that my quiet night was about to take an unexpected turn.

The doorbell rang, interrupting the peaceful atmosphere I had created. I opened the door to find a young man, probably in his early twenties, standing on my doorstep, his breath visible in the cold air. He was the delivery boy, holding a large bag containing my dinner. His handsome face was framed by messy brown hair, and his eyes sparkled with youthful energy.

“Happy Valentine’s Day, ma’am,” he said with a charming smile, his breath forming little clouds in the freezing temperature. “I’ve got your order here, and I promise it’s worth the wait.”

I couldn’t help but return his smile, feeling a little flutter in my stomach at the unexpected greeting. “Thank you, it’s certainly a welcome surprise on a night like this.” I stepped aside to let him in, already feeling a little warmer just from his presence.

He entered, brushing snow off his dark jacket, and I noticed his tall, lean frame and the way his jeans hugged his slender legs. “It’s really coming down out there,” he commented, looking back at the snow-covered street. “I’m glad I made it to you before the storm hit hard.”

“Indeed, it’s a blizzard now. Come, let me take your jacket and get you a warm drink. You must be freezing.” I led him to the kitchen, feeling a strange mix of maternal instinct and something more primal stirring within me. There was an undeniable chemistry between us, an electric current that made the air crackle.

As he sipped the hot coffee I offered, his eyes met mine, and I saw a flicker of something there, a spark of desire that mirrored my own. “I’m Kate, by the way,” I said, my voice a little hoarse as I tried to hide my sudden nervousness.

“I’m Ethan,” he replied, his voice deep and smooth. “I’m a college student, doing deliveries for some extra cash. This is my last stop for the night.”

“Well, Ethan, I’m glad you’re here. It’s not often I get such a handsome visitor on Valentine’s Day.” I felt bold, saying those words, but something about this young man made me want to shed my inhibitions.

He laughed, a warm, infectious sound that filled the kitchen. “I’m glad I could be of service, Kate. And I must say, you’re not what I expected when I took this job.”

“Oh? And what did you expect?” I asked, leaning against the counter, feeling a playful smile tug at my lips.

“To be honest, I thought I’d be delivering to lonely hearts, maybe some older folks who wanted a nice dinner without the hassle of going out. I didn’t expect…” He trailed off, his gaze roaming over my body, taking in my shorter blonde hair, green eyes, and petite frame.

I felt a rush of heat at his words, knowing he found me attractive. “And what do you think now?” I asked, my voice low and sultry.

Ethan’s eyes darkened, and he set his coffee mug down with a clatter. “I think you’re beautiful, Kate. And I’ve always had a thing for older women. There’s something so alluring about their experience, their confidence…” His voice trailed off as he stepped closer, his body invading my personal space in the most delicious way.

I could feel his warmth, his youthful energy, and I found myself drawn to him like a moth to a flame. “And I’ve always had a soft spot for younger men,” I confessed, my heart pounding in my chest. “There’s something so invigorating about their passion, their hunger…”

Without another word, Ethan closed the distance between us, his lips capturing mine in a kiss that took my breath away. His mouth was warm and demanding, and I responded eagerly, my hands threading through his hair, pulling him closer. His kiss was hungry, and I could taste the coffee on his tongue as he explored my mouth, sending shivers down my spine.

Breaking away, he trailed kisses down my neck, his hands roaming over my body, igniting a fire within me. I moaned softly, my head falling back as his lips found the sensitive spot just below my ear, his breath hot against my skin. “You’re incredible, Kate,” he murmured, his voice hoarse with desire.

I wanted him, needed to feel him inside me, but I also wanted to savor this moment, to tease and torment us both. “Let’s take this to the living room,” I suggested, my voice breathless. “I want to enjoy the fire while we make love.”

Ethan’s eyes lit up at my words, and he took my hand, leading me back to the fireplace. The flames danced, casting a warm glow over our bodies as we stood facing each other, the heat from the fire mirroring the heat between us.

I reached for the buttons of his shirt, my fingers deftly undoing them one by one, revealing his smooth, muscular chest. He was lean and fit, his skin taut over defined abs. I couldn’t resist running my hands over his chest, feeling the contours of his body, the ridges of his muscles.

“You’re so beautiful,” I whispered, my lips brushing against his skin as I kissed my way down his chest, tasting the salt of his sweat.

Ethan groaned, his hands sliding down my back, cupping my ass through my dress. He lifted me onto the nearby couch, his mouth never leaving mine. I straddled his lap, feeling his hardness press against my core through our clothes, a delicious torture.

With nimble fingers, I unbuckled his belt, my hands sliding into his jeans, grasping his thick, throbbing cock. He was hard as steel, and I stroked him slowly, feeling his length twitch in my hand. “Oh, Kate,” he gasped, his head falling back as I pleasured him.

I wanted to taste him, to feel him in my mouth, so I slid off his lap, kneeling before him. I unbuttoned his jeans, freeing his rigid shaft, and took him into my mouth, sucking gently at first, then with increasing fervor. I loved the way he filled my mouth, the way his taste and scent overwhelmed my senses.

Ethan’s hands tangled in my hair, guiding my movements as I deep-throated him, taking him as far as I could. I gagged slightly, my eyes watering, but I loved the sensation, the way it made me feel so deliciously used. He was calling me his filthy little cock-sucker, his dirty whore, and I loved every filthy word.

I sucked and licked, swirling my tongue around his head, tasting the salty pre-cum that leaked from his tip. I wanted to make him lose control, to feel him explode in my mouth. I quickened my pace, my hand pumping his shaft in time with my mouth, my lips sliding up and down his length.

“Oh fuck, Kate, I’m gonna cum!” Ethan cried out, his hips thrusting forward, his hands gripping my head, holding me in place as he erupted.

I took him deep, swallowing every thick rope of his hot cum, milking his shaft with my mouth and hand until he was spent. I savored the taste of him, the way his essence coated my tongue, and I looked up at him with a satisfied smile.

Ethan pulled me to my feet, his lips crashing against mine, kissing me fiercely. I could taste myself on his lips, a heady mix of his cum and my desire. He picked me up, his strong arms holding me effortlessly, and carried me to the soft rug in front of the fire.

Laying me down gently, he kissed his way down my body, his hands pushing my dress up, revealing my lace-clad thighs. He hooked his fingers into the sides of my panties, sliding them down my legs, his breath hot against my sensitive skin.

“You’re stunning, Kate,” he whispered, his lips brushing against my inner thigh, his breath tickling my sex. “I want to taste you, to make you cum with my mouth.”

I moaned, my back arching as he spread my legs wide, exposing my glistening pussy to his hungry gaze. He bent his head, his tongue flicking out to tease my clit, sending jolts of pleasure through my body. He licked and sucked, his tongue delving deep into my folds, finding all the right spots.

I was on fire, my body trembling with need, my hands gripping the rug as he ate me with abandon. His fingers joined his mouth, one sliding inside me, curling and rubbing my G-spot, while his thumb circled my clit, sending me closer and closer to the edge.

“Oh God, Ethan, I’m gonna cum!” I cried out, my hips bucking against his face, my orgasm building to an explosive peak.

He sucked my clit into his mouth, his fingers pounding into me, and I came undone, my body shaking with the force of my release. I screamed his name, my juices flooding his mouth, my legs trembling as the waves of pleasure washed over me.

Ethan didn’t stop, his tongue and fingers working me relentlessly, drawing out my orgasm until I was sobbing with pleasure. He wanted to taste all of me, to drink in my essence, and I was more than happy to oblige.

After my body stopped trembling, Ethan crawled up my body, his hard cock pressing against my wetness. He looked into my eyes, his gaze intense, and I nodded, giving him silent permission to take me.

He entered me slowly, his thick length stretching me, filling me in a way I hadn’t been filled in years. I gasped, my hands gripping his shoulders, my legs wrapping around his waist, pulling him deeper.

“You feel so good, Kate,” he groaned, his voice raw with desire. “So fucking tight and wet.”

He began to move, his hips thrusting in a slow, steady rhythm, his cock sliding in and out of my hungry pussy. I matched his pace, my body rising to meet his, our skin slapping together as we fucked in front of the fire.

“Yes, Ethan, fuck me harder,” I begged, my nails digging into his back, leaving marks on his smooth skin. “Make me yours, claim my body.”

He obliged, his thrusts becoming more urgent, his cock pounding into me, hitting all the right spots. I could feel my orgasm building again, my body coiling tighter and tighter with each thrust.

“I’m gonna cum again, baby,” I panted, my breath coming in short gasps. “Make me cum on your cock, fill me up.”

Ethan’s eyes rolled back as he pounded into me, his own release building. “I’m close too, Kate, so fucking close,” he grunted, his jaw clenched with effort.

I felt his cock swell inside me, his hot cum filling me, triggering my own orgasm. I screamed his name, my body convulsing around his shaft, milking him as he emptied himself into me.

We collapsed in a heap, our sweaty bodies entangled, our hearts racing. I looked into Ethan’s eyes, seeing the satisfaction and contentment mirrored in his gaze.

“That was incredible,” he whispered, his lips brushing mine. “I never expected to spend Valentine’s Day like this.”

I smiled, my heart full. “Neither did I, but I’m certainly glad you delivered more than just my dinner.”

As the snow continued to fall outside, we lay there, sated and content, our bodies entwined, and I knew that this Valentine’s Day would be one I’d never forget.