Fast Beginning

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Chance online connection leads to remarkable rendezvous.
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HighFly
HighFly
3 Followers

Author's Note: This is a first submittal for me, one of many I hope. Please let me know what appeals, and what needs more work. Your feedback, positive or negative, is very important to me!

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It was completely random, really. She was traveling from the south to Washington for a conference, reaching out to find a companion. He was browsing the personals section of an erotic literature website for the first time.

*****

CATHERINE: I'll be in Washington September 15-16 and would love to meet a sexy silver fox for dinner, maybe dancing, and maybe more. I'm looking for an attractive, articulate, well-dressed man in his 50's or 60's with silver or salt-and-pepper hair for an enjoyable evening or two but nothing serious. If you're under 50, bald, or looking for more, please don't reply. Check my profile and send me a PM if you're interested.

CHARLES: It's unlikely that I'll be in Washington for your rendezvous, but there is nothing that I would like more. I'm in St. Louis, but fly privately with great flexibility. I'm 55, 5'11", 175#, fit and attractive, with a full head of hair (lol) that is graying but also light brown. I fly a personal airplane, often from the Midwest to the South, so I may be in your neighborhood...

*****

Thus it began. There was a flurry of online messages, moving quickly to email, and then phone calls. Experiences and fantasies were discussed openly, sensually, hotly. Sexually-laced teasing became the norm. They exchanged erotic short stories designed to communicate desires and elicit conversation. A few explicit videos were shared, increasing the heat and accelerating the learning about activities of interest, and those to avoid. Within a week a rendezvous was scheduled in her home town -- nine days after first contact - with her giving only a 50/50 chance of it leading beyond the public setting. In the days just prior to the visit, the communication became even more personal, and concrete in the planning, and the odds improved to 65/35.

*****

CHARLES: I'm thinking of a trip that would involve an overnight, making lunch or dinner possible on Wednesday, or lunch on Thursday. Interested? I suppose breakfast Thursday would also be an option. How do you taste with melon?

CATHERINE: My preference is a long, leisurely lunch on Wednesday. I can meet for a late lunch then take the rest of the day off. As for how I taste with melon...there's only one way I can think of to find out! It's certainly a delicious thought though....very sensual...very sexy....mmmmm.....I'll be thinking of that image all night.

I'm SO aroused by you, by this, by the plans for Wednesday. I'm starting to wonder if lunch will be enough. I'm getting greedy for you now. Can I have you for lunch AND dinner? If I do decide to join you in your room, I will not be able to bring all the toys in the toy box. So you might bring an extra tie or two. I have a small fantasy regarding a man's tie...

*****

She shared her fantasy, and listened intently to his. Accepting his invitation to visit a website devoted to sensual, erotic massage, she began to be drawn into his hope for an afternoon of exploration and increasing pleasure.

And the day arrived...

It didn't seem possible. Nine days before, they each had no idea of the other's existence. Yet now, at 1pm on a bright afternoon in Memphis, they were about to meet after a torrid correspondence. He traveled to her this time, intent upon discovering the possible "chemistry", but knowing full-well that the heat was there, at least online.

Charles arrived early, checked into the historic Peabody Hotel, freshened a bit after the trip, and then wandered down to the restaurant. Catherine was due to arrive any minute. He hesitated at the maitre'd station, but elected to be seated. Reaching the table, he turned as he heard her approach, his eyes lighting up as he caught her beaming smile. While the polite kiss of each other's cheek was chaste, it was clear that the smoldering online heat had just been stoked.

The initial tension was thick. Neither of them had experience with online dating. They were married, but not to each other. That he had just traveled a couple hundred miles for this lunch, in the hope that it would lead to "more", was the table's centerpiece. Yet they worked through the tension, toying with their salads as they became more comfortable, laughing at the absurdity of the situation, and letting the strong mutual attraction take over.

Catherine had decided some months before that she would seek a lover. Happily, Charles personified her fantasy -- fifteen years older with sandy/silver hair, tan and lean, wearing a navy blazer with a starched white shirt and club tie. As she watched his blue eyes sparkle behind frameless glasses, she knew immediately that she would spend the afternoon in his room, living out some of the steamy scenes they had teased one another with online.

Her beauty had somewhat surprised Charles. The only picture he had seen was of a demure professional in a smart business suit, her face framed by bold glasses. The woman across the table, wearing a red silk dress, enticed him with a warm smile and a wicked twinkle in her brown eyes, unmasked by the contacts that had replaced the glasses. She appeared much younger than her forty years. He found himself adjusting his trousers, clearly affected by the increasingly overt sexuality of the conversation and the anticipation of what might be, waiting for the right moment to suggest a trip upstairs.

"I'm going to give you my key to Room 829. I'd like you to go there, freshen up, and I'll see you there in ten minutes," he said, wondering if he had moved too soon as he slid the hidden keycard across the table. Catherine lightly caressed his hand as she discreetly palmed the card, "If you'll excuse me, I have someplace to be," she purred. He arose as she did, accepted her kiss on his cheek, and watched admiringly as she walked away, her hips swinging saucily in the curve-hugging dress, her three inch heels making her 5'1" frame appear taller.

Catherine stepped behind the door as she opened it for Charles, using it as a shield to prevent anyone else in the hallway from seeing that she stood there only in red lace panties and matching bra. That was the signal to Charles that this opening act was to be the fantasy she had shared online. Taking his cue he closed the door and slowly removed his jacket, placing it on a nearby table. Looking deeply into her eyes as she stood before him against the wall, Charles deliberately rolled up his sleeves and removed his tie. He unbuttoned his shirt, and slid out of his trousers, which had been spotted over lunch as a result of his arousal and a consequence of removing his shorts before.

Departing slightly from the script she had offered, he looped the tie behind her neck, pulling her to him. They kissed passionately, enjoying for the first time the touch of lips and tongue, greedy for one another after a week of building arousal. And they stayed like that for longer than each had intended, mouths slanted across each other, her breasts pressing against his lower ribs, his cock against her stomach, hands roaming over both of their bodies.

Eventually, though, he recalled his role, raising her arms above her head and loosely wrapping her hands together in the tie, before leading her to the tall mirror at the entrance to the suite. There he gently but firmly pressed her shoulders down, causing her to sink to her knees. "Now, suck my cock, you sexy little vixen."

She moaned at his words, feeling her pussy clench with arousal, in wonder that she had found the man to help her live out this fantasy, determined to make it terrific for him as well. The mirror was a bonus, for she could watch herself taking him deeply inside, watch the bulge of her cheek as she changed angles, and see the touch of her small hands as they fondled his balls. She focused her efforts this first time on the circumcised head of his cock - licking, sucking, nibbling -- gliding her lips repeatedly over the ridge. Her fingernails lightly raked the sensitive skin beneath his balls even as she felt the gentle reminder of the binding tie on her wrists. Soon her skill and determination overcame his will to prolong the pleasure. "I'm going to come, Catherine." Redoubling her efforts, she accepted it all, as he released spurt after spurt into her mouth. Hungrily, she coaxed the last from him.

Charles helped her to her feet as she wiped some leakage from her chin with the back of her hand. Pulling her to him once again, he kissed her softly, tasting himself on her lips, fulfilling another of her fantasies -- sharing his cum in a deep kiss. "Charles, that was sooo hot...everything I had imagined. Thank you," she sighed as she folded against him.

They made their way to the king-size bed, losing his shirt and her remaining clothes before tumbling onto the spread, continuing the kiss started so passionately just before. After a few moments, though, Charles rolled away to prepare for her massage, a promised sensual experience that was to begin with an overall body massage, but lead to an extended genital massage. Both had eagerly anticipated this opportunity, and now it was time.

Charles had arrived with massage cream in two different scents. After choosing "lavender,", Catherine lay front-down on the bed, the cover having been pulled back, exposing the cool white cotton sheets. Charles had made certain earlier to adjust the thermostat, so the room was slightly warm when clothed, but comfortable when not.

Standing next to her, Charles began with long strokes from her buttocks to her shoulders, thumbs on either side of her spine and his hands two fans, finishing along her sides. This was repeated several times before he moved to gentle massage of her neck, and then on to each arm and hand, in turn. Catherine, who loved professional massages, was nonetheless in heaven, trading the seasoned pro for the eager amateur intent on providing "focused" pleasure.

"Charles, your touch on my palms, my fingers, feels wonderful."

From there he went to her feet, individually stroking her toes, lingering over her feet, his thumbs working the soft hollow beneath the arch, reveling in her soft sighs. Eventually he moved on, adding enough cream to her legs that his hands could glide over her shapely calves, the tender flesh behind her knees, and on to her toned thighs. Although he was careful to stay away from direct contact of glistening pussy lips, they were clearly visible as she reflexively parted her legs, inviting more personal contact. He did discover to their great pleasure, however, the sensitivity of the crease where her thigh joined her buttocks, stroking there with thumbs sliding from inside outwards, tugging open her moist pussy lips with each stroke. "Oh, there, right there, just like that," she breathed.

But Charles continued on, taking his time massaging her soft but shapely cheeks, varying his touch from light caresses to deep, relaxing pressure. Catherine hoped that this massage had moved to the next stage, about to fulfill its intimate promise. While new territory for her, she was lost in the sensuality of the moment, relaxed and trusting of her new friend, but eager to experience more direct stimulation.

"Turn over, please," he asked softly, eager to continue, but cognizant of the delicate moment this represented. Although Catherine had already been involved in great intimacy with him, she would be completely exposed to his view and touch, without benefit even of the customary towel for modesty. It was a moment of developing trust, so critical to the activity to come. Catherine complied readily.

Charles began by standing at the foot of the bed, gently lifting Catherine's already-slick leg. Looking deeply into her languid eyes, he bent to take her left big toe into his mouth, sucking and working his tongue much as she had in front of the mirror earlier. It was another first for Catherine, a new recognition of yet another erogenous zone, and nearly orgasmic in effect.

Though relaxed, Catherine was eagerly anticipating the next steps. Charles had invited her to view some videos of erotic massage prior to their meeting, which she now recalled vividly. She remembered the soft moans, the deep sighs, and the hungry eyes of the women in those videos, craving those sensations for herself. She recalled also the steamy conversations with Charles of the past week, wanting it all.

Well-oiled hands began by surrounding her left breast - gently, slowly pressing the sides inward, riding higher toward the erect nipple, squeezing the pliant flesh up and in - and then repeating. Five times he did this, never quite reaching the nipple, but causing it to grow happily with the building pressure. Her needy nipple, swollen and ready for more direct stimulation, reached out to him, but Charles avoided it, taking care now to reverse the gentle strokes, cupping his hands over that soft flesh and pressing downward and outward, repeating that stroke also, again and again. Catherine's right breast received the same tender treatment, to her enormous pleasure.

"Are you ready for more?" he asked as he applied a copious amount of lubricant to his hands, warming it by rubbing them together. He began petting Catherine's vulva with long, slow, gentle strokes from bottom to top, alternating hands so that the sensation was of a continuous massage. Catherine moaned softly as she opened her legs a bit more, signaling her assent and giving Charles better access to her increasingly wet pussy.

Charles was sitting alongside, half facing her feet, settling in to fulfill his promise that this was going to be "all about Catherine." His right thumb glided outside of her outer lips, slowly tracking from bottom to top, applying slight pressure inward, first her right, then left -- repeating the process again and again. As Catherine's arousal increased, and the lips became more swollen, he placed his fingers on one side, and his thumb on the other, squeezing as he moved his hand up and down, his left hand brushing her inner thigh as he asked, "How is the pressure? Too much?" He understood "just right" in her sigh, and continued the process, now adding his other hand in the same way, subtly adding a bit more pressure as his fingers soothed past her clit, feeling its hardening length massaged by her own folds.

Catherine's legs opened further when he moved his hands left and right, still sliding up and down the compressed lips, increasing the blood flow to them, feeling their increasing size and firmness. He finished this beginning with flat hands on either side, gently pressing her into the mattress, feeling her soft inner thighs, moving his hands in and out, the sides of his fingers pressing against her lips, mimicking the effect of the earlier squeezing. Catherine, lost in the erotic sensations, had a dreamy look in her eye as she breathed "More."

Judging that Catherine was now able to take more direct stimulation, Charles dragged his fingertips from below her lips upward, fingers spread from left to right, letting them nestle within her soft, wet folds -- teasing her lips and sending electric sparks as he touched her clit for the first time. His hands moved continuously, but very slowly, one following the other. "That feels wonderful, but it might be even better with more pressure, "she softly instructed. Catherine's hips began to move, trying to press against his fingers. Without warning, though, Charles softly slapped her right thigh, then her left, her belly, and her pussy, time after time, playfully engaging her with new sensations. Catherine had confessed during one conversation that she responded to soft blows when excited enough. Her deep moan confirmed for Charles that he had waited enough for the welcome change of pace.

Building on that, Charles brought more intense stimulation to the moment. He again carefully pinched her lips, trapping her clit luxuriously, pulling it sensually, focusing especially on its root. "Oh, Charles, just like that," she cried as her hips moved into his hands.

He turned toward her, allowing his left hand to slide over her right breast, thumbing the hard nipple, while his right thumb pressed easily against the bottom of her clit. Holding it there, he asked, "Is that too hard?" "Nooo," was the soft, energizing reply. Moving around her clit, he continued the periodic pressure, from six o'clock to eight, then ten, each time pressing, vibrating his thumb, releasing pent-up tightness, and in that relaxation creating a special comfort that Catherine had not known. So many times, through the years, her partner had been clumsy, harsh in his caresses. This was healing, for in her trust she found relaxation of the tightness routinely born of anxiety. He reached two o'clock, where she found a special feeling, moaning her approval and need, writhing in her pleasure, and felt some letdown as he moved lower.

"May I enter," he asked, cognizant of the importance of that consent. "Oh, yesssss," she replied, eager to feel more, and to hasten her release. Charles proceeded slowly, thoroughly lubing his fingers, placing his index finger at the entrance - teasing, stroking, until her pussy drew the finger inside. He moved quietly, deliberately, thrilled with the warmth, the moisture, the flexing of her internal muscles. Wanting to connect more fully, Charles moved his left hand to her right breast, even as he was feeling her heat within. Kneading her soft breast, teasing her nipple, he felt surprisingly connected to this vibrant, special new friend. Charles began a slow massage of her inner walls, learning from her response those areas that felt particularly good, encouraging her feedback. "Is that too much pressure?" he asked when he felt just inside, at the top, toward her throbbing clitoris. "Ummmm....no, just right," Catherine moaned. Charles proceeded to slowly move around the "clock", pressing and holding each "hour", just an inch or so inside, one knuckle, gauging her reaction at each spot, just as he had outside of her warm and wet pussy.

"Breathe deeply, Catherine," he instructed, helping her relax and stay focused on the delicious feelings, yet keeping her growing arousal in check for the moment. He found that she particularly liked it when he pressed down at "six o'clock" while at the same time gently squeezing with his thumb from the outside, rubbing the dripping skin there between his finger and thumb. By the time he got back to the top, he found her even more responsive. "Oh, that's it...right there," she exclaimed at his returning finger now pressing a bit harder against her g-spot, which was becoming firmer, and its ridged surface more pronounced. "How does that feel," he whispered as his finger slid deeper, still pressing against the length of her g-spot using his right index finger, his left hand lightly massaging her right breast. "It's just wonderful," she sighed.

Charles drew his finger back toward the opening, using a "come hither" motion to stay connected to her hardening g-spot while his thumb began gently stroking the side of her clit. Soon Catherine was ready for more, and he inserted a second finger to join in the g-spot massage. Her heels dug into the mattress now, her hips lifting, pressing against his welcome fingers, wanting more. "Patience, Catherine," he nodded, "we have more work to do.". Charles was intent now upon building her arousal, wanting her eventual release to be "memorable" as he later described it to her. So he moved his left hand from her breast to her nearly-bare mound, cupping it, enjoying the feel of the soft "landing strip". He pressed her back into the sheets, easing her body's tension, yet also trapping her g-spot between the new outside pressure and his insistent fingers within. "Oh, Charles," she purred, "that's heavenly."

HighFly
HighFly
3 Followers
12