Uncharted Territory Pt. 04

"Ah. The little lady from the organization?"

"Yes," Ron answered hesitantly.

"So, it's getting serious?"

"So, it seems."

By now, Chelsea was returning with the plates and food and another glass of wine for Debi in time to hear the latter's response.

"I had a feeling about you two," Debi remarked with no emotion in her voice, certainly no sadness.

"Oh, why is that?" Ron asked, wanting to make certain she accepted it.

"You were just so full of life after your first weekend with her." Debi frowned as she accepted the glass from Chelsea and took a sip. "There is one thing, though, that puzzles me."

"What?"

"Why are you here fucking Chelse? No offense, dear," Debi said to her co-worker, "but I didn't think you had it in you."

"Does it bother you?" Chelsea wanted to know.

"Not as long as I can play too."

"You can play," Chelsea consented.

"But seriously," Debi went on, "if you're becoming serious with this other woman, Ron . . ."

Chelsea spoke up. "You know Ron and I have worked for the company for quite a few years, and in that time, we've become close, confidential friends—"

"Yes, I would say this qualifies as close," Debi commented.

"What I mean is that, like you and I, he and I have confided in one another. He was telling me about his two weekends with Jenna and, well . . . it—"

"Made you horny?" Debi said for her.

"You could say that."

"So, this was really just . . . relief?"

"That's a very apt description," Chelsea agreed. "I'm starved. Let's eat," she added to change the subject.

* * *

It had to be one of the oddest meals Ron had ever partaken. Not the food, but rather the dining experience: three naked people sitting on the floor around the coffee table, legs crossed, eating Chinese food with chopsticks. Chelsea looked a little uncomfortable, but not so much that she said anything or covered up. Debi, on the other hand, seemed just as content as could be.

"So, it must not be too serious with—Jenna, is it?—if you're here naked with us," Debi persisted.

"Well, we're not to the exclusivity stage yet," Ron explained, "if that's what you mean. Although, with Jenna, I'm not sure it'll ever get to that."

"I don't understand," Debi said with a frown.

Ron glanced at Chelsea, who nodded for him to go on. "Jenna apparently enjoys sex with more than one person." He told her about the past weekend.

"Oh, dear! I can see why that got you horny, Chelse. Is that what you like also, Ron?"

"Well, I haven't disliked anything I've done with her so far," Ron admitted, "but, truthfully, I don't know how far I'm willing to go."

"I know what you mean. Group sex is fun, but not all of the time." Debi said it with a devilish look in her eye.

The conversation then migrated to the office and various employees and other goings on there, even some talk about their boss, Peter, and carried them through the remainder of the meal.

A short while later, as the discussion was winding down, Ron felt a foot press against his cock. He quickly glanced at Debi as the likely suspect, and the roguish grin on her face gave her away. He could also see the movement of her body from her leg and foot activity. Casually, he switched his attention to Chelsea to see if she noticed anything. Her eyes had gone wide, but she wasn't staring at him, her gaze was fixed on her co-worker. Ron's sudden suspicion was correct when he craned his neck to see Debi's other foot playing with the other woman's pussy.

Chelsea's face further reflected a mixture of pleasure and discomfort, until the latter won out and had her rising under the guise of picking up the leftover dishes and food. Ron and Debi made moves to assist but she insisted that they remain where they were.

Becoming quickly aroused, Ron slid the coffee table further out of the way and helped Debi to sit on the edge of the sofa where he had his dessert: her sweet-tasting pussy. As he nibbled away and sucked on her clit, Chelsea came back and sat at the end of the sofa, watching intently. As Ron's tongue explored every fold of Debi's vagina, his eyes met Chelsea's and they remained locked on each other the entire time. There was something singularly erotic about that.

With his right hand, he reached over, spread Chelsea's legs and played with her pussy, causing her to break their eye contact to close hers in delight. When she opened them again, an even more exciting idea occurred to him. With his mouth still firmly attached to Debi's wet hole, with his left arm, he reached up and guided her to a supine position with her head coming to rest on Chelsea's right leg.

Now, without the two fingers buried ever leaving the senior executive assistant's snatch, Ron eased onto the sofa himself between Debi's legs, where she reached for his engorged cock and steered it into her waiting pussy. The junior assistant wrapped her left leg around his back as he went to work fucking her with his dick and Chelsea with his fingers.

Debi reached up and pulled Chelsea's left arm, which had been resting on the back of the sofa, across her chest in hopes that the latter would play with the former's tits. Chelsea did so, at first, uncomfortably, having never touched another woman's breasts, but as the heat of the moment took over, she started kneading the mounds and twisting the nipples.

Ron opened his eyes for a moment to take in the scene: Chelsea sitting on the sofa with Debi's head in her lap and him plowing away. That alone was enough to push him over the edge. "I'm coming," he groaned.

It started a chain reaction. Debi threw her arms around him, moaning as her orgasm took hold, while Chelsea's hand grabbed Ron's neck to engage her climax. He continued to pump both women until each forced him to stop when she could no longer take it.

Ron collapsed on top of Debi, withdrawing his hand from between Chelsea's legs, which Debi intercepted and sucked her co-worker's juices from his fingers, while Chelsea leaned over on Ron's shoulder. Thinking Debi was pushing to get up from being smothered, the other two allowed her to get up, but only so she could lick the mixture from his cock.

When she finished, the three sat back on the sofa, relaxing.

"What do you call that, Ron? Uncharted territory? That's what this was for me," Chelsea noted. "My first threesome."

"Did you like it?" Debi asked.

"It was interesting. I didn't dislike it."

"Well, that's a start."

"But I'm worn out. I'm ready for bed."

"Now, you're talking," Debi said, enthusiastically.

"I meant, to sleep."

"Aw, just give Ron a few minutes to recycle, then we can do it again."

"You kids wear me out," Chelsea lamented, rising. "You two, stay as long as you like. Feel free to use any of the bedrooms. Just lock up when you leave." With that she trod off to bed.

* * *

"Are you in a hurry to leave?" Debi asked Ron after pouring them each another glass of wine.

"No, not particularly. Why?"

"I was hoping we could, you know, do it again so I'll have something to remember you by."

"What does that mean?" Although, he thought sure he knew.

"Well, you're going to be embarking on a new relationship, and so, there won't be any more evenings like this and last week."

"Does that bother you?"

"Well, as I told you last week, I'm really not looking for a relationship, and even though we both joked about maybe it would be nice to enter into one, I truly do not want one. Having said that, I would have enjoyed more evenings like this and last week; just fun, companionship, great sex, with no commitment."

"I told you about Jenna's sexual preferences," Ron reminded her. "If you're into threesomes, I'm sure there would be opportunities for you to join us."

"Really? I wasn't certain how much you were into that."

"It seems the more I do it, the less it bothers me." He shrugged. "I think the bigger problem I have with it is doing it with complete strangers."

"Well, then, I would really like that from time to time."

"Great. Now, you know what would really be nice?" Ron said, turning to Debi and easing her down on the sofa. "Just a nice, slow, loving fuck."

"Oh, please, love, let me have it."

Ron was kneeling on his haunches about to lean forward. But Debi couldn't wait and, with her legs spread, her pussy glistening, she raised herself up with her arms, her thighs resting on his. Seeing that was how she wanted it, he grabbed her by the waist and pulled her to him, his cock easily sliding into her yearning hole. He leaned forward and sucked each of her nipples, then pulled her to him. She started riding his slippery rod, putting her arms around his neck to hold on.

"Oh, God, this is good," she muttered.

"You've got that right." But now, he wanted her on her back, so he eased her down, his head going all the way to hers, their lips meeting in a loving kiss. He stretched his legs out and continued to pump away. There was just something about kissing while fucking that made it all the more special. To enhance the mood, they slowed their pace to enjoy the sensation of his cock sliding in and out of her warm, wet pussy.

After a few minutes, Debi whispered, "Can I get on top?"

Without a word, they switched positions and she was impaled on him with her arms out and hands flat on his chest. She didn't bounce up and down, but rather slivered back and forth, which caused his cock to seemingly rotate around the inside of her vagina providing an incredibly sensuous feeling. She stepped up her pace for a minute or so, then slowed to a crawl for a bit before settling on a more moderate speed. He reached up to play with her tits and she put her hands over his pressing them hard into her breasts.

Debi started moaning, but Ron cautioned her that Chelsea might be trying to sleep so she bent down to muffle her sounds with a kiss. He wrapped his arms around her and the closeness of their bodies mashed together was the final inducement to begin their climaxes. They each had a gentle climax that was no less satisfying than any other they'd had together.

A few minutes later, Ron's cock eased out of her as it went soft. She rolled off against the back of the sofa with her leg draped across his mid-section.

"God, fucking you is simply divine," Debi bemoaned. "If it means having to do it with your new girlfriend then I gladly submit."

"I couldn't think of anything more pleasant than being with the two of you."

They laid together for a few minutes in each other's arms before Debi got up and started dressing. "I should get on."

"You need a lift?"

"No. But do call me."

"Count on it."

Ron dressed, picked up the wine glasses, turned off the lights and departed.

* * *

Last week, Ron had been lucky enough to have three nights of unexpected great sex from three different women. This week—in only two nights—he again had unexpected sex from three different women, two of whom he expected would be good—he was not disappointed—and the third had been unpredictably good.

To be sure, all of that had been . . . well, good. But unlike last week's trysts, which collectively had produced a dilemma for Ron, this week's had actually also provided solutions—so far: get to know the women better and look for compromise.

Chelsea had steered him toward Jenna—a direction his subconscious had apparently been leading him anyway—because the senior executive assistant was unsure about Debi, and because he was not certain about Mary. Chelsea had been correct; the junior assistant had effectively taken herself out of the running.

That left Mary.

What to do about Mary?

Only two courses of action came to mind. One, since he now realized he seemed to be leaning toward Jenna, he could just forget Mary, or to be considerate, talk to her and let her know. Second, don't write her off so easily, contact her to see if there is still a spark, and if so, then decide what to do, or who he really wanted.

It took little thought to know that the second solution was the logical one.

It wasn't late so he dialed Mary's cell phone. She answered on the second ring. "Hey, Ron," she greeted in a sexy, whispery voice. Ah, for caller ID!

"Hi, Mary, how are you?"

"Fine, and you?"

He thought he detected something in her voice. Hesitance? Uncertainty? "I'm good. Am I catching you at a bad time?"

"No, not at all. What are you up to?"

There was still an odd tone in her voice. Maybe he should just cut to the chase. "I've been thinking about you quite a bit since last week and I was wondering if you still wanted to get together again."

"Oh, yeah, that would, uh, be uh, great. When did you have in mind?"

"I'm open. How's your schedule?" Ron was not getting a good vibe about this, and for an instant, he thought about just blowing it off. But maybe she was just nervous.

"Well, is tomorrow too soon?"

On the other hand, he didn't expect that. "Oh. No, tomorrow would be fine."

"Okay, good. You want to come here?"

"Sure. Can I take you to dinner?"

"Actually, I was thinking I'd like to cook. You used to love my lasagna."

He did. "What an unexpected treat. I'll bring the wine."

"Then, it's a date."

Mary gave him her address and directions, and then they hung up.

Okay, well, the conversation had started off shaky, but, at least, ended on a high note.

* * *

Still, Ron inexplicably had the nervous jitters all day. At least while at work he was mostly occupied and didn't really have time to think about it, but during the drive from the office to Mary's apartment was when he really started to feel it. The trouble was, he wasn't really certain what he was anxious about. Maybe it was just the fact that he was going to see her again. Back in the day, his heart did always beat a little faster in anticipation of seeing her. And while that might be part of it, he knew that was not all of it. Did he fear possibly having to end it before it even started, or was he frightened because he was leaning toward Jenna, and because he was, he might just discover that Mary was really the one? Was that a discovery he really wanted to uncover?

His fist actually trembled and his knock on her door was hesitant. He had also tried to anticipate how she might greet him, as though perhaps it might be a sign of things to come or what to expect. How would she be dressed; still in work clothes, changed into something sexy or . . .

Certainly to his dismay, he heard her yell from inside, "It's open!"

So, he entered and found her flitting around the kitchen in a T-shirt and her panties.

"Hey, Ron. Sorry I couldn't come to the door. I'm just finishing layering the lasagna."

"No problem."

"You brought wine? Pour us some."

She'd already set out a bottle opener and he positioned himself such that he could watch her while he uncorked the wine. What an ass! She turned slightly and he thought her nipples looked like they were going to rip right through the sheer shirt. Well, this attire was either very good or very bad.

"Sorry, I'm not dressed yet," she was saying as she worked. "I was changing and realized I needed to get this meal going, and without thinking, I came into the kitchen. But that's what happens when you live alone. I guess you know that."

"Well, you know me. I've never been one to stand on formality. If your comfortable, I am."

"I'll bet you are," she said stealing a quick glance at the bulge in his crotch. Mary opened the oven, slid the pan in, closed it, grabbed her wine, took a swallow, then headed for the living area. "Come sit."

So, Ron followed. There was a sofa and love seat in an L formation with an end table in between. She sat at the end of the sofa nearest the end table. Not certain whether to sit next to her, he opted for the end of the love seat next to the end table.

"I still can't get over us running into each other last week," Mary said.

"Yeah, that was something," he agreed. "Still glad we did?" Might as well take the bull by the horns.

"Oh, sure."

He couldn't be certain, but that did not sound definitive. Or was he just looking for a reason to end it—or not restart it? "It was good getting . . . together again." He was, of course, referring to the great sex, but he was intentionally vague to see what her response would be.

"Yes. It was always good with you."

A buzzer sounded, so she arose and stepped over to the kitchen counter that separated the cooking area from the living area. Ron turned to watch as she switched it off. She was standing on tip toes revealing full calves that gave way to muscular but not grossly shaped thighs and that beautifully round ass. Her trunk was bent over the counter and her big, globular tits hung down, the nipples just touching the counter top. His cock pulsed, and though already rock hard, he could swear it grew more. Mary apparently was resetting the timer before returning to her seat.

"Now, did you say you were seeing someone?" she asked, as though not remembering where their conversation had left off only minutes ago.

"Not really."

"What does that mean, not really?"

He shrugged. "I've gone out a couple of times with a woman I know from the organization." He instantly decided against more detail or further explanation to again see what her response would be.

"Could it get serious?"

Concern in her voice? "I guess if I let it. What I mean by that is the sense I get from her is that she would like it to get serious."

"Do you want it to get serious?"

"Honestly, I don't know."

"Because of . . . us?"

Here we go, Ron thought. "Well, last week you said you wanted to resume our relationship, pick up where we left off."

"And you said you wanted to take it as it comes," Mary noted.

"So, the question becomes, was that just heat of the moment talk, and a week later, is the sentiment the same?"

"Or, did something happen during that week?"

Ron took that to mean she was trying to tell him something did happen. "What happened?"

"It seemed to be the week my past kept catching up with me," Mary said, being vague.

"Meaning?"

"I ran into my ex-husband at the mall," she nervously explained. "We ended up having lunch. We actually had a decent conversation."

"He wants to get back together," Ron filled in.

"He said I never gave our marriage a chance." Pensively, she added, "I realized he was right. It also made me realize I didn't really give yours and my relationship a chance, either."

"And now your dilemma is to whom to give the second chance," Ron surmised.

"Just as yours is whether to go with the old girlfriend or the new flame."

"Seems we're at an impasse."

"Seems we both need to be patient enough to allow each other to make a decision."

"And mature enough to accept the decision the other makes."

"Even if they're not the same."

"I agree," Ron said. "So do you have any ideas on how to make a decision?"

"Well, I have a slight advantage in that I have a history with both of you and that means photos of our time together." Mary went back to the bar, assuming the same position as before. "Come see."

He did as she asked, but approaching her from the rear with her legs extended and her inviting ass poking out, he molded himself to her position—to her approving purr—looking over her shoulder at the two stacks of photos. He spotted an old picture of himself on top of one from a party years ago. But the clean, floral scent of her skin arrested his attention more so than the snapshots. He couldn't help burying his nose between her shoulder blades and deeply inhaling the arousing aroma. Kisses to her back and neck naturally followed.

"Mmmmm," she moaned.

His hands snaked their way around her ribs, gently caressing the sides of her breasts and lightly rubbing the very tips of her already hard nipples. His cock pulsed against her rear and she ever so slightly leaned back against it. This was all the encouragement he needed to slide his hands under her T-shirt and raise it to expose those wonderful globes so he could fondle bare skin. He cupped each, massaging them, kneading them.