Uncharted Territory Pt. 01

She looked up from her papers and glanced at him. He caught her gaze, and suddenly, it was like seeing her for the first time. She was seated about three-quarters of the way down the long conference table to his right. His chair was on the end. There was something in those sweet, sexy eyes that captivated him, and he wondered why he had not noticed it before.

Jenna and Ron were officers of a statewide non-profit organization and had known each other for a year or so. They lived in different parts of the state, so they only saw each other at the organization's quarterly board meetings. Their interaction had never been more than casual, so he knew little about her, except that he found her extremely attractive. Though she dressed conservatively, in clothes that were less than revealing, he had observed her enough to believe that beneath her modest garb was a body that could launch a serious erection on the most timid of men.

If her gaze was not enough, the brief smile she flashed him had him smitten in seconds.

"Ron, can you handle that tonight?"

Despite it all, the sound of his name did manage to arrest his attention, but only because he thought it came from Jenna.

"Ron, you still with us?"

With the harsh realization that it had come from the chairwoman, Ron forced his attention to Carol at the head of the table. "Yes?" He had no idea what she had just asked him to do.

"I asked if you could handle that tonight?"

Ron stole a glance at the papers in front of him in a desperate effort to recall the topic of discussion. No such luck. He had no choice but to answer: "Yes, I think so." Regardless of the task, there was virtually nothing in this organization he couldn't do. "But I might need some help." Maybe she would assign Jenna.

Even though his attention was aimed at Carol, Ron's head was still pointed toward Jenna. The chairwoman picked up on that. "More than you and Jenna?"

So that's why she had glanced at him. He pretended to reconsider. He and Jenna working on a project together—what more could he want? Certainly no one else. "Okay, we'll take a stab at it."

* * *

"Your room or mine?"

Still suffering from smite, Ron was taken aback by the question from Jenna after the meeting ended. Could she be suggesting what he thought, hoped?

However, he took too long to answer so she asked, "Are you okay? You seem distracted."

Ron looked into her deep, blue, mesmerizing eyes. If only she knew. "Well, you know, sometimes these meetings are not the most exciting . . . it's easy for your attention to wander. I guess I am just distracted."

"I'm sorry if I volunteered you without first consulting you," Jenna explained. "You're the only one with a laptop. If you'd rather me not use it . . ."

It was beginning to come back. She needed to do a proposal for . . . for . . . for something to present to the board tomorrow during the second half of the meeting. "No, not at all. I look forward to it"

She beamed, her smile lighting up the hallway.

"Which room would you prefer?" Ron asked, disguising his disappointment over her reason for the room question.

"Well, I'm rooming with Beatrice. I don't know what her plans are for the evening . . . you're alone, aren't you?

Ron nodded. The organization required board members to room together to save money. If a member wanted to room alone, as Ron usually opted to do, he or she paid for half the expense.

"Then your room would probably be more convenient."

How right you are, Ron thought devilishly. "My room it is. After dinner? Or do you have plans?"

"I'm yours for the evening," Jenna purred with the same sweet, sexy eyes and smile that got him into this in the first place.

"Do you realize the implication of that offer?" he asked, toying with her.

"Do you realize the offer that was implied?" she shot back with a smirk as she walked off.

* * *

The problem was, Ron did not have a clue what offer was implied. And that made him very nervous.

Ron loved women: loved to look at them, loved to talk with them, loved everything about them. He generally preferred the company of a woman to a man. In fact, he had more female friends then male, a point that his soon-to-be ex-wife hated. Ironically, his impending divorce had nothing to do with that feature of his character. He had never cheated on his wife. And therein was the root of the problem and the cause of his nervousness.

By most accounts—that he was aware of—most women found him an attractive, likeable man. He loved sex as much as the next guy, but good at it—he knew he was not. He had only had sex with one woman before marrying Dana, an encounter he still remembered fondly to this day.

But Dana had never been—and still was not—very fond of sex. He was lucky to have it with her once a month. And that act required very little talent: stick it in and try to hold off cumming until she did, which frequently took some time, if it occurred at all. She didn't much like foreplay (not that it helped anyway), loathed oral sex, and although she would occasionally allow it him to perform it on her, her mouth had never come anywhere near his cock.

As a result, his friends wondered why he had stayed with her as long as he had, and what was even more of a mystery was why the sexual issue was not the cause of their break-up. However, sex aside, Dana was a good woman, and in most other aspects, a good wife. Ron had simply grown apart from her. They had no friends, nor was she particularly interested in making any, content was she to consider her mother and sister as the only real friends she needed. Ron, on the other hand, wanted to meet people, particularly women, and have other interests beside wife and family. That was what led him to this non-profit organization. He had a talent for technology that they needed, and their need enabled him to use that talent in areas beyond the scope of his regular job. So, the further into the organization he got, the more distant his relationship with Dana became, to the point where he realized he had no future with her.

What he had not realized—a realization that was abruptly surfacing—was that he was not equipped (emotionally, not physically) to be on the market again.

It also occurred to Ron that he was getting ahead of himself. Despite their little repartee, there was no real guarantee that anything sexual would occur. And he belatedly reminded himself that Jenna was also married—to a much older man, if memory served. On the other hand, maybe the old guy couldn't satisfy her . . .

Ron shook his head to clear it. He had to stop tormenting himself. He needed a drink, so he headed in the direction of the hotel's bar.

* * *

Even the alcohol, untrue to its usual good work, did nothing to calm the anxiety Ron was feeling as the appointed hour arrived. The knock on his hotel room door only served to stimulate that anxiousness, and he forced himself to take a deep breath as he reached for the handle.

But neither alcohol nor the deep breath could have prepared him for the vision that greeted him. This was certainly a Jenna he had never seen before and only the word goddess came to mind. Elegant, yet simple; enticing, yet not trashy. She had undoubtedly touched up her make-up, though not so much as to make her seem on the prowl. She had changed into clothes obviously meant to tempt, though not to appear tawdry: an off-white button down shirt unbuttoned to mid breast, a mid-thigh length denim skirt and flat espadrille shoes that matched the color of her shirt. Breathtaking.

Ron knew in an instant he was in deep trouble.

"Should I come in or just continue to stand here?"

He stepped aside, not wanting to utter something unintelligible. She walked over to the table where he had already set up his computer. Watching her from the rear was almost as delightful as viewing her from the front. What a beautifully round ass!

"Can I get you anything?" he finally had the presence of mind to ask.

Jenna reached into her tote bag and pulled out a Diet Coke and some papers. "I came prepared," she noted, holding up the drink.

"I was going to offer a glass of wine."

"Oh," she said with raised eyebrows. "What kind?"

"I have a nice Russian River Valley—"

"I meant, red or white?"

"Which would you prefer?"

"White."

Reaching into his ice chest, Ron pulled out a bottle of her desired color. He had already uncorked it in anticipation. He didn't have any stemware, but fortunately, the hotel was classy enough to have glass glasses in the bathroom. He poured three fingers for her, then a glass of red for himself and carried the two over to the table where Jenna had already taken the chair behind the computer. She hadn't pulled the chair in yet so he was treated to an alluring view of her crossed legs, little of which were covered by the ridden-up denim skirt.

Handing Jenna her glass, he observed, "You look very nice."

Glancing down at herself as though she didn't remember what she was wearing though in all likelihood she had carefully chosen the outfit, Jenna casually explained, "Oh, I just wanted to be comfortable. Hope you don't mind."

While making me uncomfortable, Ron thought. "Not at all. So, do you really need me to do anything, or is it just the computer you want?"

"Of course, I need you to do something. But that will come later. I'm just going to type out some ideas first, then we can refine them after."

This woman sure had a way with words. The trouble was, were they just double-entendres or would something really come later, no pun intended. Or was she merely toying with him? Had she caught him ogling over her too many times and this was payback, or was that which would come later simply refining her ideas? He waited with growing anticipation to find out.

The fear was, what would he do if she did intend more?

* * *

Being careful what he wished for, Ron would have liked to know Jenna better at this point. Specifically, to have a sense as to what her motive was. Was she cruelly having a little fun at his expense; a teasing bitch? Or was it personal: did she need the esteem that making him want her provided? Or could it be genuine: she was truly attracted to him and displayed it through dress and demeanor? Or was it simply she really was just comfortable in the outfit, she was here only for his input and to use his computer, and she just was not careful in her choice of words?

He needed to just allow the evening to run it's course. However, that was not as easy to do as it was to think. Particularly, as he sat next to Jenna on her left, his chair turned to observe both her and the laptop. Interestingly, as an aside, she was an extremely fast typist. But it was hard to pay any attention to that with her perfectly tanned and shaped legs still within his scope of vision, not to mention the sculpted cleavage that tormented him from the unbuttoned portion of her shirt and hinted of an unbelievable pair of tits. Imagining what was beneath the rest of her clothing produced motion beneath is belt.

Ron abruptly noticed the silence; no rapid clickity-click of the keyboard. He looked up quickly, embarrassed that he had probably been caught.

Jenna was grinning. "Did we take another little trip?"

"It would appear so, but I'll never reveal where."

"We have ways," she remarked slyly.

Having no retort, Ron just smiled and nodded.

"Okay, I'm done. Wanna read it and tell me what you think?"

"Love to." And so he did. Then, though it was difficult because he had to look at her, they discussed it. This turned out to be beneficial because he actually got into the subject matter and was able to push all the other tortuous notions aside.

And so it went for an undeterminable amount of time: trading ideas, agreeing on concepts, refining her notes, converting it into an attractive slide show with much speed and professionalism, which she had not intended but which he was able to accomplish, to her surprise and awe.

In fact, so swept up had be become in what he was doing on the computer, it took him a while to realize that he had basically tuned out Jenna—or had she merely stopped talking to allow him to work? Regardless which it was, when the realization occurred to him he stopped and glanced at her, but actually did a double take.

Jenna was staring at Ron. He started to glance down as though his fly was open or something, but slowly became aware that she was not actually staring, she was . . . gazing? Not quite. There was a look in her eyes he wasn't certain he could describe. Almost as though . . . no, it couldn't be. No way. If he didn't know better he would have said there was a dreamy countenance . . . like she was gazing dreamily at him.

With no other course of action in mind, he continued peering into her hypnotic eyes. Within his field of vision, her hand went inside her shirt, ostensibly to scratch an itch. With great difficulty, he refrained from redirecting his attention. Still, it seemed her hand lingered longer than it should have.

And there was more stirring in his groin.

Nervously clearing his throat, Ron turned back to the computer. "Perhaps if we change this graph to a pie chart, it might have more effect."

As he was saying this, Jenna leaned in as though to have a closer look. The result of this seemingly calculated move was her thigh rubbing against his, her breast pressed against his biceps.

Her ulterior motive was becoming increasingly apparent. Only his own perceived shortcomings prevented him from going further.

Easing his chair back slowly so she wouldn't think he was uneasy with their closeness, Ron rotated his seat to face Jenna. She did likewise, and the movement caused the hem of her short skirt to ride even higher on her uncrossed legs. He could almost see the promised land. She lifted one foot and hooked her heel on the rung of her chair further enticing him. He also now noticed, not having seen when it happened, that another button on her shirt was undone. If he thought he'd seen cleavage before . . . this view made him wonder if she was actually wearing a bra.

Ron squirmed and grimaced because in his sitting position his poor cock had nowhere to grow inside his pants and he didn't want to be so blatant as to adjust himself.

To his surprise, that problem was taken care of when Jenna casually reached over and gently placed her hand on his bulge. Her eyebrows shot up in amazement at his size. "Let me take care of that for you," she said softly. And with the lightest touch, she manipulated his boner comfortably upward. Predictably, she did not remove her hand, instead lovingly running her palm along its considerable length from pulsing head to quivering balls.

For an instant, Ron thought he was dreaming. But her continued electrifying touch convinced him otherwise.

Despite considering himself unskilled, instinct took over. His computer-like mind searched its data banks for similar situations he had read about in Literotica stories. Pulling her chair to him, he cupped her beautiful face in his hands and leaned in to kiss her succulent lips.

"Finally," she uttered.

Ron halted within inches, studying her for a minute and accepted her remark not as criticism, but definitive encouragement to proceed. A second later, their lips were pressed together and Ron knew instantly, regardless how long it lasted, that this would be the most sensuous kiss of his life. Though the touch of her lips was pillowy soft, the feel and effect on him engulfed his entire body in a warmth of emotion he had never known. Their tongues danced in blissful choreography.

Ron became lost in time and space, and if it ended now, the pleasure he felt would have carried him for weeks. But Jenna's roaming hand had unclasped his pants, latched onto the tab of his zipper and was ever so slightly inching it down. Her caressing his cock delightfully continued on top of his underwear. She fumbled with the opening in his jockey shorts, giving up quickly to yank the waistband down. A breathy moan escaped her lips and his own when her hand grasped his rock hard flesh.

Jenna broke the kiss long enough to gasp, "My God, it's big!" then devoured his lips again.

Thinking he should be making further advances, the inexperienced Ron, whose Literotica memories had faded, was spellbound by Jenna's decadent kiss and stroking his cock to do anymore than hang on to her lips for dear life.

Then her thumb kneaded the head of his cock, felt the ooze of pre-cum, and she couldn't drop to her knees quick enough to inhale his rod. When she had it in far enough to reach the entrance to her throat, she came up slowly moistening every inch of his taut skin. Down she went at the same measured slow pace until she had a rhythm going. Within a few strokes, she was able to swallow him completely. He thought he might pass out from the incredible delight she was bestowing on him. No one had sucked his cock since before he married Dana. He had never forgotten that amazing experience. Jenna's skill was light years ahead of that. As pleasurable as it was, he had a moment's doubt about Jenna, who normally came across as demure and proper. Now, she was a tiger in sheep's clothing. He did recall a number of Literotica stories about women who had hidden desires that the right man was able to bring to the surface. However, he didn't fancy himself one of those men and he tried hard not to let any of these notions about her ruin the mood.

Of more concern at this point was not cumming too soon. He and Dana had sex so infrequently that when she would finally consent he had so much built up desire he had to fight to hold it in until she seemed to be ready. It was difficult, to be sure, but as she provided no stimulation, it was not impossible. Jenna was so talented, he was afraid the dam would burst any second. But as his breathing quickened and his muscles tensed, she sensed he was ready, so she calmly urged, "Come on, baby, it's okay. Let me have your delicious sperm."

And that was all it took for him to blast her tonsils. She had blown more than his cock—she had also blown his mind. Ron had never experienced anything so pleasurable. At first he couldn't even open his eyes. But his cock was still pumping away so he forced his lids open to glance down. Jenna's lips were still locked around the mushroom head of his penis and he could see her throat moving in swallowing motions. It felt as though he had unloaded gallons and he expected to see streams of cum oozing out of her mouth and down her chin. But not even a drop escaped her lips.

As he finished and started a slow deflation, Jenna let his cock slide from her mouth, but only after giving the head one final cleansing lick. She returned to her chair and swirled her tongue around the inside of her mouth. "Mmmm," she moaned. She then had a sip of wine. "That was fantastic!"

"You're telling me?"

They regarded one another momentarily, neither knowing what, if anything, to say.

"Would you like more wine?" Ron asked as a stall tactic, but also noticing she had drained her glass.

"Sure, why not."

He fixed his pants, replenished both of their glasses, adding more than the first time, and resumed his seat before her. His mind was a mixture of conflicting thoughts, but it couldn't seem to get past the overwhelming afterglow.

Jenna mistook his expression as something negative. "You must think I'm awful."

"No, not at all. Why do you say that?"

"I'm sensing you might think I was a little too forward."

"For the record, that was way beyond forward. But I have no problem with it. I guess I'm just surprised. Your public persona did not lead me to expect that."

"Are you disappointed in me?"