Charlotte's Web

Gary and Charlotte had sat inside his cramped Honda for over an hour. The discussion -- all the reasons they shouldn't kiss. First and foremost, Gary's girlfriend Lynn, who was also Charlotte's new friend. Yes, Gary's relationship with Lynn was sputtering after three years, but this was no way to end it: a heartbreaking hookup between the only man she'd ever loved and her new beautiful friend who she'd so quickly let into their lives.

Another unspoken reason was Charlotte's reputation as a serial seductress, moving through men as predatory as a shark. With her shoulder-length red hair, creamy white skin, and generous curves, she could sink her teeth into nearly any prey. When she'd fucked one too many boyfriends (or girlfriends) in a group, she'd latch onto the next unlucky community. She was, if pressed, a homewrecker down to her core, getting off throughout her day of every real or imagined illicit glance at her body from off-limits men, each one the possible beginning of an illicit affair. A married teacher, a taken doctor, and especially, a friend's boyfriend. She loved the rush, the conquest, even the drama. Living in chaos was a way of life for Charlotte, and sucking unsuspecting men into it got her off.

Of all the men she'd ever targeted, she wanted Gary the most. He was quick, funny, and seemed like he was going places. He was surprisingly athletic and competitive, which turned her on. She'd once watched him win a fierce street basketball game in front of a crowd, and seeing him grow more and more determined to win drove her wild. When he'd made the winning basket, crowd cheering, they'd locked eyes, and that was when she knew she had to have him.

So even though they'd talked themselves in circles over all the reasons Charlotte should step out of the car, which was flashing in a fire zone, she was still sitting in the passenger seat, her sundress creeping higher, inhibitions creeping lower.

"I like you," Charlotte stated obviously. "What do you think of me?"

Gary hated this naked fishing, but her pretty face compelled him to answer, "You know you're beautiful."

"I don't know that."

"You're crazy. You are so gorgeous that when I first met you at Elaine's party, I was looking at everyone else being like, 'We're all seeing how beautiful this girl is, right?' "

Charlotte beamed. Yes, that was just what she wanted. And the twitch in her pussy reminded her that his girlfriend Lynn was at his side that night.

"That's very nice, Gaaary." She always dragged out his name like he was a little boy. "Anything else?"

Gary had tread cautiously for the first hour of her interrogation, but she'd worn down his resistance. "I like you too."

Charlotte thumbed her shoulder strap. "You're obsessed with me."

Gary's eyes were drawn to the smooth, alabaster skin of her shoulder, the slope of her neck, her model's jawline.

"Maybe a little," he croaked.

"Yeah?" she whispered encouragingly.

Gary's eyes met hers. "Yeah."

Charlotte leaned, pressing her forehead into his. "I'm a little obsessed with you too."

Gary placed his hands gently on her shoulders. He lowered his face, nuzzling her neck. "Yeah?" he asked as he took a deep breath of her. God, she smelled good.

Charlotte gripped Gary's head with both hands, raising his mouth to meet hers. But he didn't kiss her. Instead, they stayed suspended in limbo for excruciatingly long, until at last Charlotte broke the silence.

"Kiss me," she commanded. Gary gripped her wrists and tried to pull his face away. "I can't..."

Charlotte reeled him back in, lust boiling. "Kiss me." This time it was Gary who pressed his forehead into Charlotte's, silently establishing a new, intimate language. "I can't do that to Lynn," he spelled out.

Charlotte tried to pull his face to hers, but he bashfully pushed it into her neck instead. She laughed at his bold evasion, then lifted his head up by his chin. She dove for his mouth, but still he resisted, turning his cheek so she kissed his dimple instead.

"Kiss me," she breathed, letting her lips linger against his stubbled skin. With them clutching each other, with Charlotte's lips already on him, it seemed silly to Gary to deny what was happening any longer.

"Fine. One kiss." Charlotte's smile was met by Gary's tentative lips, which took their time delicately exploring their new territory. Charlotte's lips were plush, like his girlfriend's. but more delicate, more wanting. He slipped his tongue between them, and was greeted by a sweet sigh. Charlotte's tongue met Gary's, and the night's tension finally found a release valve.

Gary held Charlotte close, relishing the kiss, feeling his ego grow as this gorgeous young woman picked him. He knew her reputation, but in this moment, he swelled with pride. This moment alone would be enough to fuel his sexual fantasies for weeks.

Gary pulled away, smirking. "There. You happy?"

Charlotte was now flush and damp and in no mood to talk. She kissed him again, gently coaxing his lips apart, sliding her tongue around his. Gary ran his hands along her shoulders, near the swell of her breasts. He gently caressed the edges of her mounds, enjoying how relatively chaste this had been, believing it could end here.

His first major warning sign came when Charlotte entwined their fingers and dragged them from the edge of her tits into their soft centers. Gary gasped at their size. Charlotte smiled into Gary's mouth, knowing he'd just encountered her secret weapon. The rest of her tight body was enough to tempt most men, her pretty face and wanton smile ensnaring nearly all the rest. The remaining few who thought they could resist her were felled when they discovered that encumbered underneath her tight bra was a magnificent pair of size Ds. "For your troubles," she'd sometimes laugh as she revealed them to a new lover, knowing these weren't anyone's idea of a parting gift. These were the prize.

Charlotte massaged her tits with Gary's hands, then boldly began kissing his neck, his jaw, and back to his lips, confident of her sway over him while his hands were sunk into her soft flesh. She luxuriated in their makeout session, wishing someone they knew would walk by the car and see. See her claim another taken man before their eyes, this man who all their mutual friends knew to be a devoted boyfriend in a loving relationship. The power they'd know she wielded then. They would know she could fuck them too, if she wanted. She could have anyone, she really believed, and that made her feel like the center of the universe.

Lost in thought as she filled Gary's mouth, Charlotte was snapped out by brake lights. The car parked in front of them had moved. "This must be fate," Charlotte convinced Gary as he pulled into the vacant spot, hoping he'd forget that Charlotte had occupied over two hours of his time until now. He was supposed to be home with his girlfriend soon, but instead he was being led up a three floor walk-up by a woman intent on burning his relationship to ash.

_____

Gary and Charlotte collapsed on an old blue sofa in the living room, one of the only items of furniture in this transient 23-year-old's apartment. As they kissed and ground into each other, Gary reasoned that as long as they kept it in the living room and clothed, he wouldn't actually "cheat." He'd cheated in other relationships, but not with Lynn, and he wanted to keep that streak intact.

Charlotte's sandals fell off her feet as she and Gary writhed, her dress hiked up past her thong. Gary's hands roamed freely, caressing her tight ass. her narrow waist, all the way up to her delicate cheeks. Their smacking lips filled the room under the dim light, so much so that her roommate, whom she'd of course also fucked, felt his own cock stiffen at the prospect of Charlotte claiming another victim. She reached for Gary's belt, and he grabbed her wrist.

"We can't," he whispered into her wanton mouth. His resistance sent a jolt through her. Now atop him, she ground her pelvis directly into his rock hard cock. Gary moaned and involuntarily gripped Charlotte's ass cheeks, getting lost in their suppleness.

"You're fine," she assured him ambiguously, leaving Gary falsely comforted as Charlotte worked off his jeans. Once she'd freed both legs, she peeled off his socks. For some reason this act felt intolerably intimate to Gary.

"No, really, we can't," he said, leaning up on his elbows. Charlotte flashed a toothy grin, smugly knowing her success at bedding a man once he had him in this state was perfect. The real key would be to flush his girlfriend from his mind and heart once he was inside her. That, she admitted to herself, might take some doing. But one thing at a time.

Charlotte silently placed her thin fingers on the hard lump pulsing inside his green boxer briefs. She sighed -- he was a wonderful warm handful. Her mouth watered at the prospect of what he'd look like uncovered. But instinctively, she knew she had to show patience.

Instead of diving beneath the tempting elastic of his waistband, Charlotte clutched the hem of her own garment with both hands and pulled it over her head in one swift motion. She sat on her heels for a moment, letting Gary take her in. Clad in a tight black luxury sports bra along with matching thong, Charlotte showcased her fit, youthful body, both tighter and curvier than his girlfriend's gawky frame. Lynn was actually quite alluring in her way, with dramatic eyebrows, long limbs and a large, ripe ass. But Charlotte knew her body was her most undeniable asset, and she basked in Gary's newfound awareness of the true power she possessed.

"We can't stay out here like this," Charlotte whispered, "My roommate." She knew full well he'd happily join in if he'd opened his door, but Gary didn't. Chastened, Gary stood up, scrounging for his jeans. But before he could reach them, Charlotte effortlessly took Gary's hand and led him to her bedroom.

_____

Charlotte's room was dark, and she didn't bother to turn on the lights. She pushed Gary onto her rickety brass bed and slithered her body to completely cover his. She knew he'd be disoriented in his new, dark surroundings, so naturally, his focus would be even sharper on her, just the way she liked it.

Gary rolled on top of her, clinging to her with his strong arms, ravaging her mouth and neck and anywhere else his lips landed. All the while he stirred his turgid manhood against her flimsy cotton thong, using the divot of her pussy for torturous ridged pleasure. His eyes adjusted to the darkness, and he saw Charlotte's eyes shimmering back at him in the moonlight. Though he was on top, he suddenly felt helpless. He kissed his way to her ear.

"I need to go," he whispered as he licked and sucked her earlobe.

"Shut up," she responded dismissively as she slid her hands up his shirt, delighting in his toned abs and hard chest.

"Hands up," she demanded, and Gary did as he was told. Charlotte bunched his shirt over his head, throwing it into the darkest corner of her room.

"I'm serious..." Gary said desperately, hoping she'd show him and his relationship mercy.

Charlotte clutched Gary's neck and licked straight up to his ear. "Just some fun," she assured, planting slow, sensuous kisses back down his neck and onto his exposed chest as she reached behind her back and unhooked her bra. She sat up and closed her eyes as she let her bra fall away.

In darkness, she listened to Gary's breath catch. Felt his hands slide up her belly, inch along each rib, and close around her breasts. She kept her eyes shut, relishing in the power of her tits alone.

Gary had never seen a better pair, large, round, and proud, with beautiful pink nipples jutting toward him like soft arrowheads aimed straight for his heart. He marveled at their size and firmness as his hands closed around their circumference, causing them to bulge. Charlotte placed both her hands on Gary's chest as he worked her tits, encouraging him with soft moans. As he rose toward her breasts, she ran her hands through his hair, ensuring there would be no turning back. She squeezed her arms together, creating even deeper cleavage for him to lose himself in, then dug her nails into his scalp, directing his face into her valley.

Charlotte held Gary there, letting him bury his face in her softness and fill his lungs with her scent. But soon she steered his mouth toward her nipple, and as his lips closed around it, wet tongue flattening against her hardened nub, his will to escape left him with a sigh. He began to suck.

Charlotte snapped her head back at the thrill of his capitulation. She squeezed his face into her chest with both arms, jamming her tit into his suctioning mouth. Gary's tongue lashed her nipple like it was a prisoner, slurping so hard at her intimate offering that the lewd sounds embarrassed them both. His lips attacked her other tit, desperately slathering it with his saliva, hungry for her flesh like he'd never been for anyone else's, including his girlfriend's.

He grasped Charlotte's wrists and pulled her arms behind her back, presenting her tits for him. Under the dull moonlight, they were the most perfect sight he'd ever seen, fit for worship. So he did. He ritualistically licked, sucked, and bit every inch of her glorious breasts, taking special care to suckle and stretch each of her distended nipples with his nimble tongue and teeth.

Charlotte finally broke her hands free to run them over her spit-covered tits, using the lubrication to rub her moistened fingertips around her nipples, which spread honied warmth through her torso. She smiled down on her prey benevolently. "You're fun."

Gary grinned. growing harder knowing he'd pleased her. She laid herself over him, covering his mouth with hers, smearing her big tits into his hard chest. With her nipples practically penetrating his flesh, Gary wrapped his arms around her, running his hands up and down her perfectly toned body. They landed on her ass cheeks, split by the thong now buried deep between. But as he furiously kissed her, his passion made it impossible for his hands to stay still, so desperate were they to drink in every inch of her silky smooth skin.

He gripped and regripped her, squeezing her close as they kissed, so turned on it scared him. Charlotte could sense Gary short-circuiting, and that's exactly when her systems signaled, "Now now now!" Diving her tongue deeper into his mouth than it had been all night, she simultaneously snaked her hand down his chest, flattening it so that her fingers slid seamlessly under the elastic of his underwear, grasping his cock in one surgical motion.

Guy's eyes widened. For some reason, he didn't see this coming. For some reason, he'd still felt in control until the moment her fingers curled around his rock hard member. This, suddenly, felt very much like cheating.

"Wait, wait..." Gary choked out, though he couldn't say exactly what he wanted her to wait for. She ignored him anyway, smiling with delight as she practiced a few gentle jerks on his manhood. She studied his changing expressions as she worked his cock like a joystick, which is exactly how she thought of it. His cock controlled him, and she was learning to control his cock. Charlotte loved this part, opening a man up, seeing what really got him off, giving it to him, then reprogramming him to her liking. Now that she'd accessed his pleasure center, she would take her time to learn just how to make him hers.

Charlotte kissed him with her eyes open so she could watch his tortured pleasure, giggling into his mouth as she jerked a little faster, then a little slower, then a little harder, then a little softer. Gary couldn't think straight, the thoughts in his mind scattering with each of Charlotte's varied tugs. He could only feel, and the guilt in the pit of his stomach for cheating on Lynn was currently no match for the overwhelming lust coursing through his veins.

Charlotte kept her eyes glued on Gary as she began to crawl down his body, planting small kisses on his chest, stroking him to keep him docile. When her lips and tongue reached his abs, the fluttering wet sensations caused him to gasp. "Charlotte, n-" she silenced him by sliding her middle finger into his mouth. Gary reflexively sucked it, and as he did, Charlotte pulled his cock free from his boxer-briefs.

"Charlt..." he slurred as she added another finger. She stared at his trembling dick, seven inches and thick, and knew she'd stolen right. Lynn didn't deserve a dick like this, but she sure did. And nothing was going to stop her from taking it now. Just as Gary lowered a hand to her head to try to stop her, Charlotte shoved her fingers deeper into Gary's throat while taking his shaft into her mouth.

She quickly slid him as deep as she could, his groan of pleasure cracked by Charlotte's plunging fingers. Gary's eyes rolled back as he let her fingers penetrate him and her mouth consume him. Once she felt his hands abandon trying to stop her and instead run through her red hair to help her bob on his cock, she knew he was subdued enough that she could release his mouth -- any words he spoke now would obviously be futile. She pulled her wet fingers out and used them to twist the bottom of his shaft.

Gary couldn't believe the sight beneath him. Charlotte, the mysterious girl he'd met at a party only a few weeks ago, the one whom he'd fantasized about fucking every day since he'd laid eyes on her, even when he was fucking his girlfriend, was now sucking his cock. It was a dream come true, and a nightmare. How had she even gotten him like this? Hadn't they just met for drinks and to talk? Hadn't he resolved to not even kiss her, let alone cheat with her? How did he wind up flat on his back, cock in her mouth?

None of that really mattered now, he knew, as the undeniable fact was that he was getting blown by someone who wasn't his girlfriend, without his girlfriend's knowledge or consent. He was cheating, even if it wasn't as bad as it could be. Charlotte pulled his underwear down to his knees, then flexibly used her foot to slide them off. Gary didn't want to be fully nude with her, but he was in literally no position to stop her.

She then worked his balls as she sucked his dick, swallowing him slowly and sensuously, building up his load from deep within. Gary truly hoped she'd make him cum soon. If he came now, he'd have a clear enough head to leave, drive back home, and have dinner with his girlfriend. She'd probably already texted him asking when he'll be home.

"Shit," he thought, "why does that turn me on?" Regardless of the answer, if the thought would make him cum, it would get him back to Lynn sooner, so he illicitly allowed himself to repeat the thought and expand on it.

She's probably already texted me asking when I'll be home. She's probably sitting on the couch, watching Friends, zoning out. Not wanting to consider that the love her life might be out with another woman. Might be fucking another woman. Might be falling for another woman...

"Gaaaaah..." Gary whimpered, thrusting his hips wildly into Charlotte's open mouth, gagging her. Though her eyes watered, there was a hint of a smile in them, as she could feel she'd reached a new level with Gary. He was positively desperate to cum. He may have thought her the slut because her mouth was being jammed, but she knew the naked way he was chasing his own pleasure meant that a new intimacy had been achieved. He was okay with letting himself go in front of her. He was okay with showing her through his body how much control over him she, a woman eleven years younger than him and not his girlfriend, possessed. He was okay with giving her what was rightfully his girlfriend's, his most precious, intimate gift, his seed. A fresh wave of wetness coated her already-soaked thong.

Only a few strokes from release, Gary cried out involuntarily when Charlotte suddenly pulled her mouth off his cock. "Ahhhh, please...." he gasped. Charlotte stayed on her knees as she peeled her thong off one leg at a time. Gary watched, captivated, as she looked back, stretching the thong taut from her big toe to her thumb, then slingshotting it into the darkness.