tagAnalChloe's List

Chloe's List


Chloe was an inquisitive little thing.

From the moment they met he could see that about her. On their third date, she told him she had a list of things she'd always wanted to try. Different kinks and fantasies, positions and locations. James hadn't been surprised, but the enthusiasm with which she presented him with the list was more than a little appealing.

They'd explored a great number of items on that list in the six weeks since; the variety was both impressive and daunting. They'd been to a sex club, had a threesome, tried every position James could think of in bed and out- even more he'd never dared to try. They fucked in a community park, a stranger's house, his office, and a bookstore. They had taken turns going down on each other in different restaurants and Chloe had even tipped their Uber driver with her sodden panties after he'd carefully ignored her not-so-subtle masturbating in the backseat.

Tonight, they were ticking off #28 on her list of sexual exploration: anal.

James was no stranger to the act, both in giving and receiving, but Chloe was nervous and it showed. Tension radiated from every line of her body once they retired to her her bedroom after dinner. James had reassured her that it didn't hurt when done correctly and she had been experimenting with plugs of varying sizes all week, preparing for this very night. Nevertheless, she gulped audibly when he held out his hand and led her towards the bed.

She sat on his lap, making soft, gleeful sounds as he ran his hands up and down her arms, soothing her as much as enjoying the feel of her body pressed against him. Her warmth was addictive, wrapping around him with a familiarity that was as soothing as it was electrifying; stirring a fire that was always on the verge of consuming him, should he let it.

He knew she had a plug in right now; the largest of the set. In the car earlier, he'd teased and stroked her until she'd been panting with need, sliding it into her ass before they'd entered the restaurant. Watching her flush, the desire coloring her with an irresistible blush every time she shifted in her chair, had driven him insane over the course of the evening.

It seemed like years, not weeks, since she'd come into his life. Years at least since he'd been able to control himself. She did something to him- lit up his veins with an undeniable desire. If James was in her presence, he was almost always hard and ready for her. Looking at her wide eyes now, he chuckled softly to himself.

"You are the most curious, fearless, sexy woman I have ever met. Why does this scare you so much?" he asked.

"I'm scared it'll hurt, James," she whispered.

Soft rose hued light bounced off the glossy ringlets of her pale hair. As he stared into into her eyes, he could see her trepidation. Past that, though, was the deep chasm of eagerness and longing that he knew so well. If there had been true fear in her gaze, he would have denied her striking this act from the list . It might have killed him to do, so but he could no more hurt or force her to do something she was deeply afraid of than he could force his own hand into a fire.

"Maybe we should have a safe word, like when we played with the ropes," she suggested softly.

James shook his head. Taking her chin between his thumb and forefinger, he turned her face to look him directly in the eye. "There will be no safe word, Chloe. This is not a game of submission and control. If you say stop or slow down, that is exactly what I will do. Do you understand me?"

She smiled then, her face lighting up in an expression of trust and relief. She nodded and just like that, her uneasiness faded from her gaze, replaced with a lusty anticipation that made his cock swell and his pulse race.

James held her gaze, sliding his hand across the top of one smooth thigh and under the short flowing skirt she'd worn to dinner. He traced the junction of her legs, grinning as she parted them, allowing him access to her pussy. It was molten hot, soaking his fingertips with the faintest brush against her slick folds. He pet her leisurely, teasing the plump lips and making lazy circles around her clit.

Chloe closed her eyes, resting her head against his shoulder as he probed her entrance. He slid the tip of one finger inside her, leisurely pumpking it back and forth . Her thighs quivered, legs falling open desperate to take more of him inside her. Replacing one finger with two, he slid in to the furthest knuckle, his cock going hard as granite at how easily she took him inside her dripping, pulsing cunt. He added a second finger and cupped her with his palm, pressing it hard against her clit while strumming her with the two fingers deep inside her.

"Please, James..." her breath gusted hot against his neck, hitching with the slightest pant- as she neared climax her breathing became labored.

With her release seconds away, he pulled back, keeping her on the brink. He knew she desperately wanted to be filled, could feel the desire radiating off of her; for all James knew, his need to satisfy her was just as dire. His blood raced, echoing in his ears and making his head swim. His only thought was how bady he wanted to give her the pleasure she needed.

He resisted the urge to hike up her skirt and take her until neither of them could walk. There would be time for that. For now he wanted her to ache for him until it drove her mad.

He raised his hand and pressed the two fingers that had been been inside her to her lips, tracing them lightly and smearing clear gloss down toward her chin. Her lips parted on a sigh as he pushed his fingers past them, stroking her tongue, urging her to suck them clean of her own arousal.

Withdrawing his hand, he grabbed her by the chin and pulled her in for a deep, feverish kiss. He took to her mouth like a starving man, seeking out every crevice of her mouth. He mimicked what he wanted to be doing with his cock, thrusting in and out rapidly, only to slow down and trace the lines of her cheeks and lips with his tongue.

He sucked her bottom lip into his mouth, biting it softly. Her taste was heaven and his hips moved of their own volition to grind his erection against her pillowy ass. Pulling back with a groan, he urged her to stand in front of him. She was beautiful and as he positioned her facing away he slowly slid her skirt down her hips. The miniscule slip of fabric pooled around her ankles and he raised each of her feet gently to help her step out of it, massaging her calves, thighs, and the sweet swell of her ass.

Grasping each cheek in his large hands, he kneaded their roundness, cock jumping in his pants every time they gave him a glimpse of the large plug buried snug inside her. His fingers flexed, digging deep towards the lower crease of her ass, pulling apart her cheeks to expose her fully.

Chloe moaned, her back arching as he grasped the base of the plug and twisted it slowly before giving it a gentle push deeper inside her. He teased the clearly hungry flesh with his proximity, blowing softly on her swollen labia, reminding her of how achingly empty she was there. Taking the plug's base firmly in hand, he pulled it free with a deliberate slowness, groaning as her body relinquished its hold on the dark treasure in a smooth slide.

"Are you ready for me Chloe?"

"I'm so ready, James," she purred. "Please take my ass, I need you right now!"

He smiled at her eagerness, only too happy to oblige, he stood and quickly undressed, pausing only to help remove Chloe's blouse and bra. He bent for a moment to lavish fevered, wet kisses to each of her small breasts, sucking each of the peachy buds into his mouth and giving them a quick bite. Her gasps shot straight from his ears to his cock; her vocal enthusiasms making him harder than steel.

Lying her down on the bed, he massaged a small shapely hip with one hand and cradled her to his chest with the other. Taking pleasure in her form, he touched every inch of her soft skin, kissing and nibbling her neck and shoulders. James loved the fresh lemon scent of her body wash and the way it mixed with the darker smell of her arousal. She was like a drug to him and he wanted to spent a lifetime treasuring her with his hands, his mouth, and his cock.

"I promise to go slow baby," he murmured in her ear. "This will feel so good."

Chloe nodded, Her eyes glittered with anticipation in the soft light. Her body quivered against him, hips moving against his body in a sensual motion. She wanted this, he could tell. The way her head lolled back against his shoulder making it obvious she was still riding the high- if not frustration- of being kept on the edge of orgasm.

He ran a hand down the length of her delicate spine and spread her ass cheeks wide. Reaching for a bottle of lubricant, he liberally applied it to her small puckered hole, laughing when she tried to squirm away as the cool liquid coated her sensitive flesh.

Fingering her gently, he spread the lube around and in her untried opening, allowing it to warm and cover her completely. Sliding one finger inside her, he traced the ring of her entrance, coaxing the tight hole to accept first one then a second finger. He scissored them, back and forth, stretching her with a careful determination, adding more lube to make sure she was slick and prepared for him. He did the same to his cock, making sure his entire length was coated in the slippery liquid.

Fisting himself in a tight grip, he tapped at her playfully with the swollen head, taunting her slit for a long moment before allowing the full length to rub against her. He pressed his cockhead to her asshole and pushed forward gently, easing it past the tight ring of muscle and then stilling, allowing her to become accustomed to his girth. He knew he was larger than the widest flare on her plug and where that tapered off, he was thick and broad all the way to the base of his shaft. Taking him would be a different experience entirely.

Despite every cell in his body screaming to take her and take her hard, he waited. His muscles tense, on fire with the desire to bury himself in her tight hole. When Chloe began to squirm, working him another inch inside her, he grit his teeth and waited still. James let her wiggle and grind her ass on his length, swallowing him deep with a maddening slowness. She set the pace and soon, he was buried as far as he could be inside her, his testicles resting snug against her weeping, soaked cunt from behind.

"Christ James, I'm so full! I can barely stand it," she cried out.

He would have worried she was in pain, until he noticed she had moved her hands to cup her breasts. She pinched at her nipples, pulling and stretching them while undulating her hips against his body and moaning loudly. Unbelievably, he felt her pussy grow even wetter for its lack of attention while she lie with her ass impaled on his shaft.

"I wish you could see how beautiful you look with your asshole stretched around my cock," James whispered against her ear. He held her close to his front in a tight embrace.

She trembled as he began to thrust inside her, feeling her inner muscles milking him in a vise grip. He wrapped an an arm around her delicate frame to part her thighs and gain better access to her clitoris. The position also provided crucial leverage as he increased the speed of his hips.

Chloe surrendered completely to him. Her body bucked and shuddered like a woman possessed as she came once and then again. James continued stroking her clit in furious, tight circles, gently pinching the tiny tight bud of nerves between his fingers as she crested her second climax. She screamed in pleasure, her face contorting and her eyes staring into the distance, wide and unfocused. James knew she was past the capacity to articulate, swept away on a raging tide of sensation.

He slowed his hips to give her time to recover from the two back to back world shattering orgasms. Pulling his hand away from her oversensitive pussy, he continued fucking her in languid, unhurried strokes, taking his time while her breathing calmed. She turned her head to kiss him deeply.

James knew what she was trying to convey with the intimate kiss. He could feel her gratitude in the slow way she nibbled his lips. Could taste how badly she still wanted to come again in the way she sucked at his tongue and clashed teeth with him. Her hips began setting the pace for a faster rhythm once more.

He tried to communicate the same and more to her in that kiss. His own gratitude for the gift of this experience with her. How fast he had fallen into fascination- and perhaps even love- with Chloe rocked him. He hoped she knew how precious she was to him and vowed silently to tell her every chance he could.

"You're perfect to me Chloe," he whispered. "I want to be inside you every second of every day and when I'm not, it's all I can think about."

"James...I need more!"

Her moans grew louder and as she begged for pleasure, he rolled her onto her stomach, giving in to her demand for more. She ground her hips back against him and he met each thrust with a surge forward of his own. He fucked her hard and fast until they were both crying out in release. James pumped his hot semen deep inside her, groaning as her tight hole tried to milk him for more.

Slipping gently from her, he leaned forward to kiss a trail from the base of her neck down her back, leaving a lingering kiss on the two dimples just above her behind before getting up. Chloe sighed with contentment and was still lying in a boneless heap, a small grin splitting her face, when he returned a moment later with a hot wash cloth.

James pressed it against her sensitive flesh, soothing her doubtless aching body and wondered to himself, what was next for the two of them? Both now and in the future. He wanted more of this woman- wanted as much of her as he could get. Would she tire with him soon? Would she want to keep exploring her list of sexual curiosities?

He didn't have to wonder long.

Chloe gave him a brilliant smile, eyes darkening with desire and a unique glint of humor he was beginning to know well.

"So about #29 on my list..."

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by Anonymous

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by Anonymous12/06/17

Great writing

You're a great writer! I'm sure your stories will score much higher with lengthening them. Great work and I look forward to more!

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by AlexSlaine11/22/17


Yes! I will be releasing more stories featuring these characters. :)

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by Anonymous11/21/17

Will there be any more Chapters for Chloe and James?

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by Anonymous11/19/17

Good Story

Like the detail.

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