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Adventurous Sheryl

She wanted to lead, he was excited to follow
Adventurous Sheryl

The day dawned in a splash of color and clouds. Warm sunlight glinting off the river bounced rays of color along glass canyons. It would be a hot day. The brisk walk down Wacker Drive already caused a trickle of sweat to run down his back as he hurried along. He was heading to his office and work, but his mind was far from there. It had been several months since he and Sheryl had seen each other. She lived in another city, traveled occasionally to Chicago. They met while he was working on a project in Kansas. The relationship began as a casual greetings in the halls, though from the first moment Steve felt attraction. For months they passed each other daily, or shared an elevator, rarely saying more than "Hi."

Sheryl took the first step. It was just another morning walking to work when Steve came up next to her and said good morning.

"Hi there, how are you today?" she replied.

"Great, another day in paradise," he joked back.

"So you travel here every week?"

"Yeah, fly in on Sunday night then back out on Thursday"

"I bet hotel rooms and restaurants get old."

"They sure do. As nice as a hotel may be, it's still a hotel room. I enjoy good food and wine, but I sure get tired of dinner alone."

"Yeah, that’s no fun." Sheryl said glancing at him. She’d been attracted to Steve as well. He was average height, in decent shape for his age, impeccably dressed. His platinum hair was short and his piercing blue eyes seemed always attentive. He was someone she could enjoy, intellectually and physically.

"If you ever want some company for dinner, let me know."

"Thanks. That would be great. I'd love company. Is there an evening that works for you?"

"How about tomorrow?" she replied and they made the date.

Sheryl was an Irish beauty, blessed with a flawless complexion, stunning red hair and curves where a woman should have curves. She had a compelling aura, a sensuous, fun-loving spirit simmering just below her refined surface, tinged ever so slightly with sadness. You don't reach the midpoint of life (whatever that means) without experiencing sorrow along the way. Perhaps it was a shared sense of promise and loss, expectations and disappointment that drew them together.

Steve was the naïve one. Though older he'd lived a subdued life, burdened for years by self-imposed morality and religious restriction. He'd left that world a decade before with anticipation and excitement. Determined to taste pleasure and joy, he'd flirted with life and hungered for experience, but was still reserved. While they didn't know it yet, there would be a balance between them, a Ying and Yang that would offer mutual fulfillment.

Dinner began comfortably enough, good food and a nice French wine in a quaint atmosphere. Sheryl led the way that night, gradually and gently unveiling the thought that they might share more than just good Bordeaux. Initially surprised by her liberated expression of desires, Steve was flattered and aroused. Thoughts of Sheryl in his arms, her firm breasts pressed against him, had more than once filled his imagination. She opened the door to satisfy mutual longings and he gladly crossed the threshold.

Their love-making that first night was intense. His tender caress and hungry kisses were matched by her confidence and raw sexual energy. She knew how to touch him, to take him in her mouth, consuming him with warmth. As she drew his hard cock inside, his kisses and impassioned thrusting urged her toward orgasm, while she squeezed, pulled and teased him. Their simultaneous climax engulfed their entwined bodies in waves of unbelievable pleasure. He collapsed against her then rolled to her side. Gently playing his fingers over her still swollen nipple, he said "Now that's a first."

"What do you mean?"

"Well, it's the first time I've had an orgasm at the same time as my partner."

"Really? It's all a matter of muscle control", she said with a wicked smile, "and I like practicing my control. Want to try again?"

"I'm going to need a little recovery time" he laughed, "but I bet you don't, and I know why God gave me a tongue." With that he kissed and licked down her breasts over her belly to taste the sweetness of her smoothly shaved pussy.

Months had passed since that first evening together. During that time their getting together had been infrequent with the duties of work and travel often interfering. When they did get together Sheryl was the adventurer, leading Steve to new and different sexual territories. Each episode was etched in his memory, a delightful place to revisit in quiet moments, usually leading to self-pleasure.

Then his project had come to an end and he returned home. While they talked occasionally and exchanged notes via e-mail, today would be the first in months they'd see each other. So as he walked into work that morning, enjoying sunshine and the river, his mind was already wondering what unique pleasures lay in store that afternoon. Just then his cell phone buzzed. "Hello?"

"Hi sexy, just wanted to let you know I got in OK this morning."

"Great!" he replied, "Does your day look crazy?"

"I've got to make a few calls, but I should be back to the hotel by 4:00. I can't wait to see you."

"Me too!" he said. "I'll pick up a bottle of wine"

"Yummy! See you then."

As you can imagine, Steve was not quite 100% work focused that day. He attended meetings, completed reports, but his mind strayed often to what lay ahead. He didn't know what Sheryl had in store, only that she had promised to surprise him. Anticipation was sweet and as morning waned into afternoon he savored each advancing minute.

Sheryl's hotel was not far from his office, so at 4:00 PM he left the office to walk over. The day had grown hotter, the pavement sending shimmering heat waves back to the sky. The rush-hour crowd hurrying to commuter trains and busses had not yet reached gargantuan proportions and for a moment Steve walked alone, lost in reverie of a prior rendezvous.

That time Sheryl had arrived at his hotel room, rushed from the day but ready to relax and enjoy. Steve poured the wine to let it breathe and held out a glass to her, wearing the white cotton hotel bathrobe and a smile.

"That is so nice!" she said, kissing him softly after taking a sip of the wine, reaching down to stroke his cock through the open robe. "Let me go rinse off a little."

As she was in the bathroom, Steve lost the robe and stood naked by the window, savoring the wine. He looked out on the city, the traffic rushing by, and wondered whether others were rushing home to lovers, or whether their hectic lives left time for lovers or wine. Even husbands and wives should be lovers, he thought.

Sheryl came out of the bedroom, tiny droplets of water glistening on her alabaster skin. Steve sensed her approach from behind then felt her nipples brush his back as her arms encircled his waist. He reached behind and pulled her to him, her pubis mound pushing against his firm butt. She kissed his shoulder as he leaned back against her and she grasped his rising cock. As he turned around she held him, teasingly stroking as his mouth met hers. His hands moved to her nipples and gently teased them to hardness, the skin of her areola rising with goose-bumps as testament to her excitement. Breaking their embrace she said, "Come over to the bed. I have something for you."

He hesitated, not wanting to let her go and bent down to suckle her nipple. She pulled his head against her breast and leaned back a little as his hand moved down to stroke her pussy. "Come over to the bed," she repeated and led him across the room. "Lie down on your stomach."

Steve smiled and did as she asked. Her hands began to stroke his back and down his legs. She touched along his inner thigh, gently spreading his legs in the process. Her hands moved up to his butt cheeks and she massaged, sliding her fingers up his back as well. The movements stopped for a moment, and then she was massaging his skin with scented oil. Her fingers moved along the crack of his ass. The oil was warm and wet as her finger played along his butt. Slowly, tentatively, she slid a finger into his butt hole, feeling the tightness. His moan of pleasure brought a smile. "Is this OK?" she asked, as she continued to stroke her finger in and out of his ass.

"Yes – different but nice" he replied.

"Get up on your hands and knees" she said. "Move down towards me."

Again he did as asked. Now she had access to his balls and cock. She straddled his legs, slipping one of hers between. She put more lubricant on her hands and stroked from his bottom, along his scrotum and up his cock. Her hand moved in a gliding, turning motion, caressing and pulling the length of his hard shaft.

Distracted by the sheer pleasure of her manipulations, Steve was only slightly aware of her other hand playing with his anus. She continued to probe and stroke him. Then, with his butt hole relaxed and wet, she slowly slipped a small butt-plug into his ass. He felt the insertion and pushed back against her, allowing his butt to take all of it.

"How does that feel?" she asked.

"It all feels good," he replied.

She continued stroking his cock and balls, while slowly moving the butt plug in and out of him. As she pleasured him, her breast brushed across his ass and back and she would push her pussy against his thigh. All of this was incredibly arousing for Steve.

"God," he said "my cock feels like it's huge! If you don't stop I'm going to cum!"

"It's OK baby, you can cum. Or do you want to cum inside me?"

"Yes, I want to be inside you"

She stopped her manipulations and slid up on the bed next to him. Spreading her legs she guided his throbbing cock into her hot pussy. From the tension in his body she could feel it wouldn't be long. He loved the way she wrapped her legs around him and pulled him into her, the walls of her vagina squeezing and sucking on his hard penis. In seconds his orgasm erupted and he poured himself into her.

"I'm sorry – I should have held on longer"

"Never apologize for an orgasm," she said. "I love it when you cum. I love to feel you pulsing inside me. I enjoy giving you pleasure, you enjoy giving it to me – it's not about perfect balance or equal orgasms, it's about sharing our bodies and great sex!"


That vivid memory slipped to the forefront as he drew closer to her hotel. What is it attracts two people? Why do we see tantalizing beauty in one, so often hidden from view, but can't find it in others? What comprises beauty? Steve chuckled at his inclination to wax philosophical. Perhaps that capacity to ponder, to feel the child-like wonder at newness and play were what Sheryl found attractive. It certainly wasn't physicality. Middle-aged, slightly over-weight, a face lined by the years, he would not be gracing the cover of GQ soon. And as desirable as he found Sheryl, it wasn't only her body that aroused his passion. Even now walking through the growing crowd of commuters and shoppers, it was her complete embrace of her sexuality, her pure delight in taking and giving pleasure that aroused his spirit, titillating like ice pressed to hot skin. And not just the spirit, he laughed.

Walking through the lobby of the hotel, he paused to admire the striking cut flower arrangement of lilies and roses, their scent stirring the air with whispers of sensuality. He took the elevator to her floor, opened his bag to retrieve the bottle of Cabernet, and walked to her door. He knocked twice and she opened the door. His eyes widened as he took in the scene, and she chuckled and pulled him in.

"Like it?" she asked. She was wearing a black leather & lace boustierre with half-cups that pushed her rosy hard nipples out for him, a garter belt and fishnet stockings that led to stiletto heels, but left her shaved pussy and round bottom naked and tantalizingly touchable.

"WOW!" he said not taking his eyes off her, and set the wine down on the chair by the door. "You look incredible," he said as he moved to kiss her. She allowed his kiss, but then gently pushed away and went to the cocktail table, returning with two flutes of champagne.

"I know you were bringing wine, but I wanted some bubbly to celebrate since we hadn't seen each other for so long. Are you enjoying your surprise so far?

"Oh yeah, this is great"

"Well, remember how said you wanted to try new things?"

"Sure," he replied.

"Then we're going to do this my way; but first, cheers, lover. It is so nice to see you." They clinked glasses and sipped the cold champagne. "Now, take off your clothes."

Following her direction, Steve kicked of his shoes, pulled off the socks, then his shirt and dropped his trousers.

"Stop!" she commanded, as he was about to pull down his briefs. She was seated in an arm chair, casually holding her champagne while watching him, her eyes licking along his body as she fondled her nipple with her left hand. "Come here."

He walked over to her and stood, awaiting her wishes. She took some champagne into her mouth and set down the glass. She reached toward him and pulled him forward. Then she peeled down his underwear slowly to reveal his cock, rising in eagerness. With a smile, she closed her lips around his cock head and let the cold champagne tickle him. Slowly taking him deeper into her mouth, she held him, running her tongue along his shaft as the bubbles intensified the stimulation. He ran his fingers into her hair, but she pushed his hands away and slapped him on the ass. He let his arms hang at his side and just enjoyed her teasing. She lifted away from him, leaned back and swallowed the champagne.

"Now," she said, "take the champagne in your mouth, get down on your knees and suck my clit."

Without a word he followed her orders. Leaning forward as she spread her legs, his mouth holding the bubbly effervescence, he placed his lips against her wet pussy. Finding her swollen clitoris, he took it in his mouth and let the bubbles caress while his tongue flicked over her. She moaned and pulled his head against her, pushing herself forward on the chair and spreading further to give him access. His hand reached up to touch her nipple, but again she slapped him, harder this time. He knew not to take his mouth away and continued to suck and tease her clit with his mouth, the champagne dribbling slightly from his mouth, along her thigh.

"Swallow the champagne," she said, "and lick it off my legs."

As he did, she steered him with her hands. He finished cleaning along her left thigh and she pulled him back to her pussy, lifting her hips to meet his hungry mouth.

"Lick my pussy all over then down to my butt," she said. He obeyed, savoring her taste as he swirled his tongue along her labia, inserting it gently then pulling back. He licked down to her ass hole and again circled with his tongue, then pushed it in feeling the tight pressure of her anus. Her moans grew more insistent as she pulled his mouth back to her throbbing clit. He could feel her cresting, rising toward climax and furiously sucked and licked hoping to bring her there, when she suddenly pushed him away.

He was taken by surprise and wondered if he'd done something wrong, but her flushed complexion and dreamy smile said otherwise. Still holding his face, she bent down and kissed his mouth, pushing her tongue to play with his, licking the outside of his lips. Then she pulled his mouth to her nipples, first one then the other, enjoying his gentle bites and kisses. She put her hands on his shoulders and moved him away as she stood in front of him. He stayed on his knees as she moved to the dresser and opened a drawer. Reaching in, she pulled out an unusual looking device.

"You said you wanted to try more toys, right?" she asked.

He nodded and watched her body sway as she walked back to him.

"This is one I like. You see, this part goes inside me and then I put this inside you as well." The strap-on cock was about 7 inches long and realistically veined. Behind it protrude two more phallic devices, one clearly to penetrate the vagina, the other for her butt.

"Sit on the chair," she commanded, "and stroke your cock. I want to watch you." As she said this she touched herself, rubbing her inflamed pussy, running her fingers down to her crack. She took some lubricant and spread it on her end of the toy, all the while watching Steve move his hand up and down the length of his cock. Its head was purple and shining, a tiny drop of pre-cum glistening on the tip. Sheryl licked her lips and inserted the device into her waiting holes, strapping it around her waist.

"Now move to the bed and get on your hands and knees."

Steve went to the bed, still holding his cock.

"That's right," Sheryl said, and moved next to him, leaning over so her nipples brushed along his bottom and up his back. She reached between his legs and ran her hand across his penis, swiping the droplet of per-cum with her finger. She licked it then ran her hand along his ass as she whispered, "I like the taste of you too."

He felt the cold, hard dildo stroke along his thigh as she leaned forward. Then she planted kisses along his ass, down to his crack, while stroking his pulsating cock. She toyed her tongue at his butt hole and gently spread his cheeks with her hands. The butt plug and dildo in her ass and pussy felt so nice, so filling, and each time the large black frontal cock pressed against Steve she could feel their pressure inside her as well. Taking the lubricant she lavished it along his butt crack, down to his balls and erection. She returned to his anus and slipped a finger in, gently probing and stretching, sliding it in and out. He knew what would follow and the anticipation alone was almost enough to make him cum.

"I'm going to be very gentle with this," she said, "and if at any point you want me to stop just say so. But I have to tell you, when I start to move this in and out of you it will feel so incredible for me too!"

"While I never thought I'd say this, but fuck me baby!" Steve replied and reaching up touched her hand as it held his cock,

Sheryl put lubricant on the long black dildo and moving forward began to push the head in Steve's ass. He tried to relax his sphincter and receive, but it was really tight. True to her word she was gentle. Slowly the bulbous head disappeared in his gaping hole. Now she could rock slightly and feel the movements stroking the attachments deep in her pussy and ass. The one teased her clit as she continued to apply gentle pressure inserting the cock in his ass. Every few second she would let her fingers dance along his cock and squeeze him as she watched his face for signs of pain.

The plastic cock was now three inches inside him and he felt like his dick would explode. Contracting his keegle muscle he succeeded in calming his twitching penis. He wanted to prolong this experience.

"Is this OK?" she asked as another inch of the shiny black cock slid inside him.

"Yes, it feels good," he groaned and leaned back against her.

She began to ease the tool slowly in and out of him, one hand touching his butt while the other stroked his penis. Each movement increased her pleasure as well, and she felt her own orgasm, earlier forestalled, rising up again. Her movements became longer and deeper, with each thrust pressure building inside her pussy, each stoke rubbing her throbbing clit while her fingers wrapped around his rock-hard cock.

"Oh! This is so good!" she breathed lustfully, "Another two seconds and I'm going to CUM!" she whispered, her body shaking as wave after climactic wave pulsed through her. She stopped her thrusting, aware Steve might not be able to take more and collapsed over his arched back, her arms reaching around to pull him to her.

"God, baby! My cock is ready to explode!"

She lifted herself slowly, slid the glistening dildo from his ass and said, "Cum in my mouth."

Pushing him on his back she took his hard, arching cock in her hand. The grimace on his face betrayed unadulterated pleasure and she knew he was almost there. Bending down she ran her tongue from his balls to the tip of his cock and closed her mouth over him. Stroking his cock with her tightened grasp once, twice, she sucked hard as he convulsed and exploded in her mouth. He thrust up to her, his cries of pleasure filling her ears. She sucked and licked along his cock while his body quivered in the throws of orgasmic delight. Finally, his hands lifted her head from his still throbbing cock and pulled her up next to him, wrapping his arms around her, his thigh between her legs.

"So, did you like that?"

"I'm not sure like is an adequate word," he replied.

With that she snuggled against him, her smile beaming and let his fingers play with her nipple while she teased his relaxing cock.

"Now I'm ready for a glass of red wine," she said with a laugh, and kissed his mouth.

Another memory, he thought, another experience I would never have without her. He could only hope the rest of life would prove near as pleasurable.

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