her-generous-gift
FIRST TIME SEX STORIES

Her Generous Gift

Her Generous Gift

by madobsession
20 min read
4.42 (14800 views)
adultfiction

It was a late afternoon, and the library was hushed as always, a haven of solitude and well-worn books. Jamie hunched over his stack of notes, earbuds tucked in as he struggled to focus on the chaos of equations splayed out on his laptop. The shy, nervous nineteen-year-old had barely left his seat all day, pushing through with dedication and discipline that bordered on compulsive. After all, who else would willingly spend a Saturday afternoon here? He was an obvious mark--the kind of boy who never looked up, kept to himself, his cheeks always tinged pink around strangers.

And she saw him.

Lena was there to research for her latest project--at least, that was the intention. But her attention had shifted the moment she spotted Jamie buried under those books, his dark lashes casting shadows over his cheeks, biting his lip as he studied. She had an eye for these types, the quiet, overlooked ones with untapped intensity simmering beneath the surface. He seemed so absorbed, and Lena knew how to shake that focus just right.

She eased her way down the aisle and stopped right in front of his table. For a long, pregnant moment, she simply watched him, letting her shadow fall over his screen. When he finally looked up, she was there, leaning with casual elegance, one brow arched in playful curiosity.

"Oh, sorry," she murmured, not moving an inch. Her voice was a little too smooth, her smile a little too knowing. "Didn't mean to interrupt. You looked... focused."

His mouth opened, then closed, and he swallowed, glancing away like he wasn't sure if he was allowed to keep looking. "Uh, no, it's-- it's fine. I was just, uh, studying," he stammered, his words spilling out in a clumsy heap. She kept her gaze steady, letting him fumble and flounder.

"I could see that. You looked... dedicated," she purred, eyes catching the way his hands trembled slightly as he adjusted his earbuds, which he'd abandoned now, all attention on her. Her long, manicured fingers traced an invisible line on the table's edge, every movement slow and deliberate, like she was savoring the effect she was having on him. "Calculus?"

He nodded, flushing as if ashamed to admit it. "Yeah. Exam next week."

"Figures." She chuckled softly, the sound warm but laced with a hint of something almost predatory. "You don't get out much, do you?"

He swallowed, his eyes darting to the side, that blush deepening as he muttered, "I-- well, I do, sometimes, just... I'm busy with school and..." He trailed off, clearly flustered under her gaze. Lena tilted her head, feigning sympathy, but her eyes glinted with amusement. She let her gaze linger a touch too long on his lips, then on the nervous bob of his throat.

"Pity. All work, no play. Such a waste," she murmured, her tone low, rich, brimming with unspoken possibilities. She straightened, stretching slowly, the fabric of her blouse straining over her curves. His eyes flickered over her figure before he could help himself, but he quickly looked away, his blush now reaching the tips of his ears.

"Maybe," he muttered, sounding both embarrassed and eager. His gaze kept darting back, as if drawn despite himself, each glance betraying that desperate curiosity he was trying so hard to hide.

Lena leaned in, her voice dropping just for him. "If you ever feel like taking a break, Jamie, just let me know. I think you'd be... fun to loosen up." The way she said his name, drawing it out, felt like a touch in itself, smooth and warm, coiling around him. He stammered out something--she couldn't even make out the words, only the shy desperation laced through them. That was enough for her.

Her fingers brushed over his hand as she pushed his notebook toward him. "Just don't study too hard," she whispered, her breath warm against his ear, savoring the way he stiffened, his lips parting as she lingered close for a moment too long. She pulled away with a smile, leaving him in a haze of confusion, his chest heaving, his thoughts scrambled.

Lena's hips swayed as she walked away, her presence like a challenge in the air, inviting him to follow. And damn it if he didn't want to, his body suddenly aching, his mind unable to shake the images she'd painted with her words, with those looks that promised much more than an innocent invitation.

Jamie spent that entire night trying to shake her from his mind, but it was hopeless. No matter how hard he tried to focus on equations or read the same line of his textbook, he kept seeing her sly smile, those knowing eyes, that subtle roll of her hips as she'd walked away, every step leaving him more entangled in her web. That face, that mouth--he'd seen her before. But where?

It clicked suddenly, around midnight, as he lay in bed, eyes wide, blood surging hot with the realization. That smirk. That voice. Lena. No wonder she looked so familiar--she was the very woman he'd been jerking off to for months, the same woman he'd found by accident one night on a quiet, cam site that had rocked his entire world.

In her streams, she was playful, unattainable, yet somehow...intimate. He remembered her seductive glances, her curves wrapped in silk or lace, how she would run her hands down her smooth, peachy thighs, lips parted as she teased her viewers, her every move steeped in an unhurried, simmering confidence. Every time she positioned herself on all fours, her lush, round ass arched high, he'd lose control, his fingers fumbling as he tried to keep himself steady.

Now that same woman knew his name, had stood close enough for him to breathe her in, leaving him dazed, burning with want. The thought alone was enough to have him gripping himself under the covers, imagining that she knew, that she'd somehow orchestrated it, that her teasing looks were all part of a plan to leave him hanging.

The next day, he couldn't concentrate, barely ate, barely moved from his bed, replaying that encounter over and over. He tried to tell himself that he'd made a mistake, that it was too absurd to be true. But then, two days later, she appeared again, like a storm rolling in. He was back in the library, almost hoping she wouldn't come--but dreading more that she wouldn't.

"Miss me?" She sauntered up to his table, dressed in a leather jacket over a low-cut top that hugged every curve, her jeans perfectly framing that same unforgettable ass. Her eyes sparkled as if she'd guessed every wicked thought he'd had. Jamie's face burned, heart racing, his mind tumbling into chaos.

"I--um--" he stammered, caught in her gaze, unable to look away, certain she could see every secret he'd ever kept. She laughed softly, low and velvety, her lips curving in that smile he'd memorized.

Lena leaned forward, her fingertips grazing his notebook. "You know, I noticed how you looked at me last time." Her words were a quiet murmur, barely audible, each one laced with daring confidence, like a cat teasing a cornered mouse. "And I could have sworn I've seen you before. Tell me, Jamie...have you seen me somewhere?"

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He swallowed hard, eyes fixed on her mouth, heat pooling low in his gut. He tried to answer, to explain himself, but the words just tangled in his throat.

"Hmm," she purred, almost thoughtfully, tapping her lips as she studied him. "You seem like the kind of boy who's spent a few...lonely nights. The kind who'd like a little attention." Her hand slid down, skimming along the side of her thigh, stopping just as his gaze followed, her tone a whisper made of heat. "Or maybe I've been giving you that attention already. Does that sound right?"

Jamie felt the room close in, the warmth of her body a smoldering presence. She leaned closer, the scent of her perfume dizzying, her voice melting through his nerves. "Next time I'm on," she murmured, "why don't you watch real close?" Her eyes narrowed, her gaze dark and steady, leaving no room for him to hide. And with that, she walked away again, that unforgettable ass swaying just as he'd dreamed of countless times, leaving him frozen, pulse pounding, desperate to see more.

Lena wouldn't just give it away. She was clever, deliberate, and she'd spent years perfecting her ability to pull people into her orbit, drawing them close without ever seeming to try. A quick approach would have bored her. Besides, she could sense the nerves on Jamie like a scent, knew the quiet boys like him needed a nudge, some coaxing. They wanted to be devoured, even if they'd never admit it.

The next time she saw him in the library, she didn't make her presence obvious right away. She watched him for a few minutes from a few tables over, her back turned, casually scrolling on her phone, catching glimpses of his fidgeting hands, the way his fingers tapped his notebook in distracted beats. She felt his glances, shy and stolen, like he wasn't even aware he was looking.

Eventually, she made her move, sliding into the chair across from him with an easy grace that caught his attention immediately. She tossed her bag onto the table, giving him a quick, casual smile that might as well have been a private confession.

"Jamie," she greeted, sounding like they'd been friends for years. "Didn't expect to run into you here again."

"Oh, uh, yeah. I just, um... study here a lot." He tripped over the words, eyes darting away from hers, hands automatically adjusting the edge of his notebook like it was a lifeline.

She laughed, soft and genuine, and leaned forward a little, giving him just a hint of that view he knew so well from her streams. He noticed, she could tell, but he kept his gaze fixed downward, cheeks flushed.

"You always this shy?" she asked, pretending to be preoccupied with a nonexistent spot on her phone screen, letting the question hang in the air just long enough to make him squirm.

"Not--no, I mean, sometimes. Just...not used to people talking to me out of the blue, I guess." He forced a tight smile, fiddling with the edge of his notes again, fingers trembling slightly.

She didn't push him, not yet. "That's fair," she said, her tone easygoing, like she wasn't sizing him up with every word. "I like places like this, too. Good for thinking, getting away from people. You seem like you're the kind who needs that sometimes."

He nodded, his mouth twisting in a little smile at her understanding. She was letting him relax, drawing him out slowly. And, just when he seemed to settle, she dropped her next line.

"So... Jamie. What do you like to do when you're not studying?" Her eyes flickered with something just a touch darker, enough to have him stammering again.

"Uh... you know, I just--I game sometimes, read, I guess. Not much," he mumbled. He didn't even realize he was leaning closer, drawn in by her quiet intensity, wanting more of her attention.

"Reading, gaming...all that time alone," she mused, each word soft but deliberate. "Don't you get... lonely?"

The question struck him hard, his face burning. He shrugged, trying to shrug it off, but he couldn't deny the way his stomach flipped, that gnawing, hot pull. "Not really... Well, maybe sometimes," he admitted, his voice quiet. She could see he was trying hard to keep his cool, to stay composed, though his fingers still fidgeted with the corner of the paper.

"Hmm," she hummed, letting the silence do half the work, her gaze lingering on his mouth, his hands. "I think you're lying. But that's okay. Shy guys like you? You're always trying to act like you don't need it." Her voice had a lilt to it, and his face went scarlet, unable to meet her gaze.

He swallowed, eyes dropping, and then, as if caught in some current he didn't understand, he looked back up at her, meeting her eyes this time, half-challenging, half-curious.

"Maybe..." he murmured, barely audible, his pulse a hammer in his throat. "Maybe I am."

The spark in her gaze flashed hotter. "Good. I like honesty." She leaned back, giving him that smile again, a little reward, the sort of look that said she knew exactly what she was doing to him. And she didn't stop there.

"Tell you what, Jamie," she murmured, her voice soft and intimate. "Why don't you prove to me you're more than just a quiet boy with a pile of textbooks?" She let her words hang, a dare that curled around him, her gaze steady, teasing.

He blinked, struggling to process, his thoughts a flurry. He wanted to ask how, what she meant, but all he could do was stare, his mind racing, caught between confusion and excitement.

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"If you figure out how," she added, her lips curving, "maybe I'll give you a little... incentive. Just between us."

With that, she stood, giving him a lingering look over her shoulder, her hips swaying as she walked away. He watched, entranced, her words sinking in, realizing she was leaving it up to him to find out what that "incentive" might be.

Jamie barely slept that night. Her words looped in his mind, that teasing promise of something he'd never dared imagine in real life. The next few days blurred together, a torturous blend of his classes and his attempts to study, but he couldn't focus, not when he kept seeing her face, her figure, the way her voice had wrapped around him. She wanted him to prove something, but how could he? A part of him wondered if it was all just a game to her, if she was toying with him for fun, enjoying the sight of him squirming under her gaze. But another part knew better. She was selective, careful--she didn't give out attention for nothing.

On the fourth day after that meeting, he gathered his nerve and messaged her, managing to find her social account. The text was simple, polite, but with a hint of desperation he couldn't mask. Hey Lena, it's Jamie...from the library. Not sure if you remember me, but...you left me curious about that "incentive."

It was hours before she responded, and by then he'd all but convinced himself she'd forgotten him, that he'd misread the entire thing.

When Lena saw Jamie's message, she had to stifle a grin. She knew he was probably agonizing over every word, second-guessing himself, wondering if he'd made a mistake reaching out. It wasn't exactly the sort of message she usually got, especially from the guys who regularly hit her up online. She had plenty of followers who weren't shy about what they wanted, who didn't trip over their words or send these awkward little texts. But Jamie? He was something else. She could tell he wasn't just looking for a cheap thrill; he wanted something more, even if he was too shy to admit it.

She took a few moments to consider, tapping her nails on the side of her phone. He was cute, in a pitiful, endearing way--the kind of boy she'd never usually go for, but also the kind that she knew would never forget her if she gave him half a chance. A pity fuck, she thought, but one she could enjoy on her terms, keeping him wrapped around her finger. And maybe he'd enjoy the attention--she could tell he wasn't the type to get it often, if ever.

Finally, she messaged him back, keeping it light, almost breezy. Hey, Jamie. I remember you. So, curious, huh? I like a curious mind. What exactly are you hoping to get out of this...incentive? She could imagine him now, reading her words, turning them over in his head, wondering how much to admit. It was fun knowing she had him spinning with just a few lines.

His response came after what she guessed was a solid ten minutes of nerve-wracking typing and deleting. I don't know, really. I guess I just wanted to get to know you better. You seem...interesting.

She laughed softly. Interesting? She wondered if he had any idea who he was talking to, if he'd pieced it together yet, or if he was still in the dark, just thinking she was some friendly girl with a mysterious air. She decided to push him a little further, letting him stew in that mix of nerves and anticipation she knew was driving him wild.

How about this, Jamie, she replied, fingers flying over her keyboard. Why don't we hang out this weekend? A drink, maybe some conversation, somewhere casual. I'll even let you ask me whatever you want.

She was half-surprised when he agreed so quickly, but it only confirmed what she already suspected. He was a little desperate, a little lonely, probably used to his own quiet little bubble, and this was his way out of it. She smiled, a wicked glint in her eyes as she imagined how much he'd blush when they finally met up outside of that stuffy library. She could already see herself drawing him out, getting him to loosen up, coaxing him with teasing touches and wicked smiles until he was melting in her hands.

When Saturday came, she kept her look just shy of provocative, just enough to make his jaw drop but casual enough to keep him on edge. A soft, clingy sweater that hugged her curves, jeans that accentuated every dip and swell, and a touch of lipstick, just enough to make him notice every word that left her mouth. When she met him at the little bar just off campus, she could tell he'd spent hours getting ready, though he still looked as unpolished and anxious as ever. She had to resist the urge to pat his cheek.

"Hey, Jamie," she greeted, all warmth and sweetness, like she wasn't keenly aware of every flicker of his gaze.

He stammered out a hello, his eyes darting to her sweater, then down at his own drink, blushing already. She could practically feel his pulse from where she sat, leaning in just enough to keep his attention rooted firmly on her.

They chatted for a while, her questions gentle, almost motherly, drawing out his interests, his dreams, his lonely weekends. And Jamie, for all his bashful stammering, was eager to share, his face lighting up as he talked about his favorite games, his goals for school, that quiet fire in his eyes that people like him always kept hidden. He had such a soft, earnest quality, the kind of pure-hearted sweetness she rarely saw in her line of work.

At one point, when he was nervously looking at his hands, she leaned closer, resting her chin in her palm, eyes sparkling as she watched him. "You know, Jamie," she murmured, her tone a little more intimate, letting a hand rest lightly on his arm, feeling the muscles jump under her touch. "You're cute when you talk like that. You don't get told that enough, do you?"

He looked like he'd stopped breathing, his eyes wide, cheeks flushed. He shook his head, trying to keep his gaze anywhere but on her, like she might disappear if he looked too long. She could almost hear his heart pounding, feel the way his nerves tangled and tightened under her fingers.

She leaned back, pretending to sigh, letting her fingers trail slowly from his arm. "Pity," she murmured, shaking her head with a small, knowing smile. "Someone should be giving you more attention. You've got...potential."

He was speechless, his fingers wrapped so tightly around his glass his knuckles went white. He mumbled something she couldn't quite hear, but it didn't matter; she had him exactly where she wanted. Her eyes softened, and she gave him a little smile, one that said he was special, that maybe she could be the one to make up for everything he'd missed out on.

Maybe, she thought, she'd give him a night he'd remember for the rest of his life.

Lena watched him, lips quirking in amusement as Jamie spilled more of his thoughts, his words loose and free from the drinks. There was something almost endearing in the way he rambled, eyes bright and soft as he relaxed into the seat across from her, his awkwardness fading, replaced by a boyish charm she hadn't expected. He'd confessed to seeing her on that site, a blush blooming high on his cheeks as he fumbled his way through the admission, too drunk to manage the embarrassment that came afterward.

"Oh my God, I'm so sorry--I shouldn't have..." he muttered, his words stumbling over each other, but Lena waved it off with a laugh, one eyebrow arched in playful curiosity.

"It's fine, Jamie," she said, letting her finger trace the rim of her glass. "Honestly, I'm flattered. I don't exactly do those streams for my health, you know?" She shot him a wink, watching him squirm, a shiver running through him as her words sunk in. "Besides, it's good to know you've got taste. I mean, if I'm your 'hottest girl you've ever seen'...well, that's not a bad title."

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