Uncharted Territory

Author's Note: Please read Uncharted Territory Part 01 first, if you haven't already.

Part 02: The Test

The week started exceptionally well. Ron felt he was on top of the world. His coworkers noticed he walked with a bounce in is step, he was more cheerful, more friendly, more talkative. He felt strangely free of stress, as though in addition to all the immense pleasure he had derived from all the intense and incredible sex, his body had also been purged of tension and worry. He even slept better.

And all because he had gotten laid.

Jenna had been correct: the mind was an incredible device.

He thought about her constantly her beautiful face and body, her perfect tits and ass, and that lovely flower with its dainty petals between her legs. And of course, there was her stellar, easy-going, likeable personality and intellect. What a package!

Naturally, Ron relived every moment of their time together, especially the spectacular sex. It was still almost surreal to think it had all really happened. It was his own Literotica story. But best of all, he had performed in a manner that made it

worthy

of a Literotica story.

Ron rode that cloud for a couple of days until—like all clouds—it began to evaporate, then the storm of doubt rolled in and he started questioning what happened. Oh, the memory of it was still there, but he began to view it through a fog.

No longer certain was he that his sudden sexual prowess was so keen. Face it, he had been so sexually frustrated for so long that any woman could have probably gotten him off so well. Hell, it was likely that even Dana could have done it—if she had actually participated instead of just laying there as she always did.

Had it really required someone as skilled as Jenna?

On the other hand, maybe it actually was her talent. Maybe he hadn't really performed that well. Maybe she made him think he had. Did she really have all of those orgasms? He wondered. That was the curious thing about a woman's climax. Could a man ever really be sure that it occurred? Or was it merely good acting? Guys were ever so much easier to tell. Ejaculation couldn't really be faked.

Oh, why all this doubt, this confusion? Why couldn't he just accept things at face value? Why did he have to analyze everything? Although, that was part of his job, and therefore, part of his nature. He worked with computers. If it was a hardware issue, you analyzed it, determined the problem, and either fixed or replaced the faulty part. With software, you analyzed the program, determined the cause and fixed or replaced a line of code.

But this situation wasn't so clear cut. What was he to do?

Perhaps he just needed another weekend with Jenna to revitalize himself, remind himself that he could satisfy a woman. But is that what would really happen, or would it just be her letting him

think

it was happening. Or was it that he really could satisfy her and the real question was could he satisfy another woman? Were he and Jenna just that compatible or was she just so sexually attuned that anyone could make her come?

So now, what was the solution? Did he have to start sleeping around to prove to himself he could satisfy other women? If so, how many before he would be convinced? But if he was so uncertain of himself as to wonder whether he could please other women, what made him think he could even get another woman to sleep with him to even attempt to satisfy one?

Damn you, Dana, you did this. Ron had always been a person who was confident in his abilities. Now, he was turning into a sexual neurotic.

He needed a relaxing cold beer to break out of these tortuous, self-defeating thoughts. Fortunately, it was closing time.

* * *

On any given day after work, a number of people from the office could be found wetting their whistles at the lounge down the street. Prior to his breakup with Dana, Ron had rarely visited the popular watering hole. Now, he was a more frequent participant. On this Tuesday, it was where he headed.

He recognized a number of employees who were bellied up to the bar, but none he was particularly close to, although there were one or two with whom he could at least shoot the shit. After he got his beer, but before he could head in their direction, he heard someone call his name.

Sitting alone in a booth was Chelsea, the senior of two administrative assistants to the president of the company. She summoned him over. "Join me."

Ron did so without hesitation, primarily because he really liked her. She was also a good person to have on your side with the boss (he always made sure her computer was in top shape with the latest updates and software). She either liked you or she didn't, and it was said if she didn't you would never know it. She had told him that she liked him, and he had the sense she would only say that if she really meant it. The further evidence was in her invitation.

Chelsea's other appeal was that—aside from being a dozen or more years older than he; late 30s, early 40s he guessed—she was a very attractive woman. She took very good care of herself, was dark complected with almost black hair, average female height, and her best feature was her large, but thankfully not huge, breasts that she liked to show off with tight, low cut shirts. Best of all, she could get away with it.

"So, what brings you here?" she asked conversationally. "You're not a regular."

"I was going to ask the same of you?"

"Shall we just say that some days the job is more tedious than others and a little attitude adjustment is needed before the trip home?" Chelsea held up her martini glass in a mock toast.

"Understood." Ron likewise lifted his beer bottle. Translated, she meant the boss had been a bigger asshole today than usual.

"And you?"

Ron shrugged. "Nothing to go home to."

"The divorce not going well?"

"No, no. No problems there."

"Still a small flame for Dana?"

"Long extinguished. I'm over that."

"So, there's another woman." Chelsea posed it as a statement rather than a question—as though she already knew.

"What makes you say that?" Ron played it cool, but underneath, not so much.

"Womanly intuition."

"You know I volunteer for a non-profit organization?"

"You had a board meeting this weekend as I recall."

"Yes."

"You met a woman." Another statement. Did she really have him pegged?

"I actually already knew her."

"And you got to know her better."

Ron wanted to say: Why don't you let me tell the story. But then it might have been obvious how little he wanted to say. "Yes."

"And then?"

"You seem to have the conversation all figured out," Ron said lightheartedly. "You tell me."

"She wants a relationship, but you're not sure you want to be involved again so soon."

"That's partly correct."

"Ah," Chelsea said, leaning back in her seat, "it's sexual." With that, she placed her hand in her cleavage, rubbing up and down as though scratching an itch, but more as a gesture one might do while lost in thought. With her other hand, she sipped her martini.

Ron had yet to do any more than give her breasts the occasional quick glance, but with her touching them, she was almost calling full attention to them. Now, it was difficult to look at anything else. He also now noticed that her nipples had begun to make their presence known as the imprint in her shirt grew—as though the mention of the word sex had had an effect on her.

He didn't know how to respond to her last comment. Did he really want to get into that subject with her?

"No comment?" she prodded.

"That subject is part of the equation," Ron explained, uncomfortably, "but it is rather complicated."

It evoked a snicker from Chelsea. "Are you afraid to discuss sex with me? Am I too old for you?"

"No, no, no. Not at all. To both questions. It's just . . . as I said . . . complicated."

"Okay. Well, I won't pry. But just know that if you change your mind, I'm a good listener."

"Thanks. I appreciate that."

"You're sure it's not because I'm older?"

"Absolutely not," Ron replied honestly. "That's not even a consideration. I don't even think of you as older."

"That's very sweet of you," she smiled warmly. Again her fingers toyed with her cleavage. The nipples had never faltered and were still at full attention. "You ever had an older woman?"

The question should have caught him off guard, but it didn't. He wasn't sure why. The beer was kicking in, and because of her tits, he was viewing Chelsea not as the boss's assistant, not as a co-worker, but as an attractive, sexy woman. So, why not have a little fun. "No, I have not."

"Because you didn't want to or just never had the opportunity?"

"Of your two choices, the latter."

"Buuuut?" She dragged it out to elicit further explanation.

"I never cheated on Dana."

"Oh, you doll," Chelsea said in genuine appreciation. "Are you telling me you've only ever had sex with your wife?"

"No."

"Oh, and the new girl."

"There was a girl before Dana."

"Three, then."

"You act surprised."

"You're a good looking, hunky guy, Ron." She became diplomatic. "I wouldn't have been surprised if there had been more. But it's nothing to be ashamed of."

"I never said I was." He swallowed the last mouthful of beer, and noticed Chelsea's glass was empty. "Can I get you another?"

"Please. This is getting interesting."

Standing at the bar waiting for their second round, Ron was able to see their table. He was surprised to notice Chelsea touching up her make-up and wondered why. Perhaps this would be her last drink before she headed home to her husband. Stupidly, nothing beyond that occurred to him, even as she tugged her shirt down a bit to show a little more cleavage. On the walk back to the table, drinks in hand, he was able to see her shapely legs under the table, of course crossed, and revealing a fair amount of thigh. If she could see herself through his eyes, age wouldn't even cross her mind. This was a real woman.

"Thank you, sir," she said, accepting the martini.

Before she could jump in with more questions, Ron asked, "Did you come alone?"

"Yes. Is that bad?"

"No. Just not many women do."

"You mean, women my age."

"I didn't say that."

"Well, I'm a bachelorette tonight. No hurry to get home."

Ron nodded. "Hubby out of town?"

"Yes. Although it's not much different when he's home."

"Sounds sad."

Chelsea shrugged. "After a few years, things become routine."

"You seem to have a hang-up about age."

"As you'll eventually see, it becomes a factor."

"Age is just a state of mind," Ron quoted.

"Easy for you to say. You're still young."

It was his turn to psychoanalyze. "So, your husband is not so attentive." He took her tack and offered statements instead of questions.

"Not so much."

"So, it's a sexual issue with you, as well."

"Touché."

"Want to talk about it?"

"Nothing to talk about. It's a tired old tale. Operative word: old. You can probably figure it out."

Ron let his eyes fall to her chest and the greater expanse of breast available to his eyes. He thought he could almost see the upper curve of an areola. He felt a hard on coming. "Would it help if I told you what an attractive woman you are? And I remind you this is coming from a younger man."

"It doesn't hurt. But it's not enough."

"What would be enough?"

"Well, right now, a ride home."

"Of course."

"Let me go ahead. I don't want anyone to see us walk out together."

* * *

Déjà vu is what it was.

Driving along with Chelsea in the passenger seat, legs crossed, dress up exposing thigh and the reflection of passed street lights highlighting the tops of her boobs was not unlike the ride home with Jenna; except that the administrative assistant was more refined, more elegant than the wildcat from the organization.

Ron attempted to keep the conversation generic since sex and relationships seemed to be off limit subject for each. "Not that it matters, but how else would you have gotten home?"

"Any one from the office still in the lounge would have been happy to give me a ride. Too many want to be in with the boss's secretary."

There was a sadness in her voice that touched him. "That had a rather lonely sound to it."

"Because of my position, I can't get too close to many people," Chelsea bemoaned. "I won't let anyone use me to get to the boss. Unfortunately, that's what too many want to do."

"Not me."

"I know. You're one of the rare few I would call a friend." There was a genuineness in her voice.

"Thanks. I'm touched."

It was a short ride to her home.

"Come in," Chelsea offered when he pulled up to her address. It was actually more of a command. Once inside, she said, "Open a nice bottle of wine from the rack in the kitchen. I'm going to get out of these clothes. Be back in a minute."

Ron uncorked a nice Pinot Noir, hoping a light wine might lighten the mood that was growing somber by the minute.

Chelsea returned wearing a short negligee, not quite see-through, covered with a matching robe. She looked stunning, and his expression reflected that feeling. He didn't see this coming.

Seeing the shock and awe on his face, Chelsea commented, "You obviously didn't see this coming. You really have been off the market."

It all instantly fell into place for Ron: the invitation to her table, the attempted discussion about sex, the more than usual display of tits, letting him know not only that her husband wasn't servicing her, but that he was also out of town, the ride home, the invitation inside, changing into something more

comfortable

. After all of this time, he should have been worrying about more than just being able to satisfy a woman in bed; he should have realized he didn't recognize the signs—just as had happened with Jenna.

Okay, well, this was another trip into uncharted territory. But it was not going to be a wasted one.

With strains of Simon and Garfunkel playing in his head, in his best Dustin Hoffman imitation, Ron said, "Gee, Mrs. Robinson, are you trying to seduce me?"

Chelsea had been standing there waiting a few moments to see what he was going to do, but she couldn't help busting out laughing. Yet it was confirmation that she had made the right decision. She went to him intending to wrap her arms around him, but he was holding two glasses of wine so he took evasive action to prevent spillage. They unintentionally worked against one another, collided, sending a splash of wine onto her chest that cascaded over the top of her breasts funneling down her cleavage.

Thinking quickly, and now knowing what he was about, Ron set the glasses down on a nearby counter, and before Chelsea could react, he started slurping wine from between her tits.

At first mystified by Ron's actions, Chelsea was quickly swept into it when his tongue action turned to kisses. "Oh, yeah, baby, clean me up!"

Ron's penis took over thinking for him, and it couldn't get enough of those marvelous mammaries. Without his mouth ever leaving her skin, he slipped her robe off, then eased the thin straps of her nightie off her shoulders. Inadvertently, the entire garment also slid down her body to the floor—not his plan, but it worked nonetheless.

Now, onto the piece de resistance: those pointy nipples that had been teasing him all evening. He sucked on them, giving each equal attention, like a baby long overdue for a meal.

It felt so wonderful, Chelsea had to take a step back to lean against the wall or she would certainly collapse. But she dragged him with her.

With intensifying passion, Ron lifted her to raise her breasts even with his mouth, then carried her to the nearby couch. He set her down gently, kissing a trail south to her shaved pussy. When his talented tongue made contact with her drenched clit, she screamed: "Oh, my god!" then grabbed his head to keep it affixed to her burning pussy. He alternated flicking her button, then bathing it in circular motions. Her breathing was a combination of quick breaths and whimpers. He sucked the juice flowing from her like delectable candy. She came in a series of jerks and shudders, reveling in the ecstacy until her clitoris became so sensitive she had to push him away.

Upon lifting his head and seeing the combination of his saliva and her juices smeared all over his face, she roughly pressed her lips to his both kissing and licking at the mixture. Coming up for air, Chelsea stammered, "Oh, Ron, you are incredible. Make love to me, darling."

But before he could even stand to remove his trousers, she was grabbing at his belt to do it for him. When she had his clothes open enough to pull his pants and jockeys down, he stood and motion caused the garments to slide to his ankles. It also resulted in his rock hard boner springing free and whacking her in the face. Momentarily stunned, her eyes widened and assumed a wanton expression as she viewed the symbol of pleasure before her. Strangely, she did not take him into her mouth, as he might have expected, but instead she grasped it and pressed it to her chest between her tits—a gesture equally as appealing—and continued to hug it as though absorbing warmth from it.

Ron was going to lay her down on the sofa, but she halted him. "Not here. Let's do it right." Chelsea stood and led him down the hall to her bedroom. He had a brief, creepy feeling at the thought of fucking a woman in the bed she slept in with her husband. But she had already laid down with her legs spread and was pulling on his cock, so the weirdness passed. She yanked his rod almost as if it was not attached to him and guided it right to her yearning, sopping pussy.

Once inserted and enjoying Ron's trademark slow plunging, Chelsea wrapped her arms and legs around him as though holding on for dear life. Her pussy felt totally different from Jenna's, smaller and tighter, the obvious result of little use. Another difference was the look of pure lust on her face. And where Jenna was a moaner, Chelsea was quite verbal. She was enjoying it positively: "Oh, yes; oh, yes; oh, yes!" negatively: Oh, no; oh, no; oh, no!" and even spiritually: "Oh, god; oh, god; oh, god!" And most importantly, she was loving the one she was with: "Oh, Ron; oh, Ron; oh, Ron!"

Of course, it was no less pleasurable for him. Her tightness was maddening, and that coupled with the licking he'd already given her had him ready to explode. He held back, waiting for her, and within seconds, she was screaming: "I'm coming! I'm actually coming!"

"I'm right with you," Ron groaned.

"Oh, yeah, darling, come with me. Come with me. Come

in

me. Oh, fuck yeah!" She kept up the stream of expletives and was still coming long after he had hosed her inside. She wouldn't let him stop pumping, and he could feel his semen being plunged out with each stroke. Just as he was about to lose his erection, she came again.

When she was completely finished, Ron pulled his wilted stick out and rolled over onto his back beside her, completely spent.

Chelsea turned her head to face him, seemingly in a fog. "My, god, Ron, that was the best sex I've had in years. I've

never

come three times in one night. You are incredible!" She rolled her head back taking a deep breath, basking in the afterglow, a dreamy expression forming on her face.

He took a few minutes to catch his own breath, and when he looked back at her, she was asleep. He frowned. That was supposed to be

his

job, he thought, wryly. Easing out of the bed gently so as not to awaken her, Ron stepped into the bathroom to clean off. She was still sleeping upon his return so he took a minute to admire her body as this was the first opportunity he'd had to really see all of it unclothed. There were a number of hot looking twenty-somethings that flitted around the office in clothes designed to show off their great bodies. But not one of them had a thing on Chelsea. She could stand up to any one of them. Why would a husband not be proud (and not chronically horny) with a wife like that? Unless, of course, there was a side of her that was a total bitch.