Wanderlust Ch. 02

He massaged her pussy lips, even as his tongue and lips were eating her out. He slipped his fingertip inside of her, eliciting another moan.

"I need you inside me," she moaned.

He continued to finger fuck her, with two fingers and then three. He wanted to make sure she was good and ready for him. For his size.

When her body started to tremble and her pussy was dripping wet, he knew it was time.

His wrapped his strong hands around her hips and slowly guided her down, down, onto his massive cock. She was facing away from him and sitting, as if in a chair pose, onto his lap.

It was what she wanted, more than anything, but she was a bit apprehensive too.

She reached back, to slow her descent, flailing for something solid to brace herself. Her hands found his arms and shoulders. She felt his strong muscles tensing. It just added to her hunger.

And then she felt it. The head of his cock pressing against her pussy.

She closed her eyes and bit her lip. She gasped as the head spread her and popped inside.

To him, it was the feeling he had been longing for. To enter her. To feel her warm, wet pussy lips enveloping him.

He lowered her an inch further.

She lay her head back, moaning, feeling the water pelting her. Raining down on her.

She too was back under the waterfall.

Her hands moved to the tops of his thighs, gripping them, controlling her descent. His legs felt big and powerful.

He was still holding her by the hips, suspending her in air. She felt secure in his hands and yet at his mercy too.

What if he pulled her down suddenly? What if he impaled her all at once? He could if he wanted to. It would feel like he was splitting her in two.

He must have sensed her trepidation because she heard his deep, soft voice.

"Are you okay?"

She nodded.

"Not too fast."

He held her there, his cock only a few inches inside her, and let her acclimate.

"I liked that feeling when you first pushed inside me," she whispered.

He lifted her up and then lowered her again, so his head popped inside again.

"Like that?" he asked.

"Ohhhh, yeah like that," she moaned.

He did it again.

"Oh God," she cried. "You're gonna make me cum so hard!"

"I like it too," he said softly. "The idea of entering you. Of becoming part of you. I want to be one with you, Olivia. As close as two people can be."

She reached back and held his head, her fingers caressing his dark curly hair.

"Go deeper," she gasped. "I'm ready now. I want to feel you inside me. Deep inside me."

He began to lower her again. Despite what she said, he was taking it slow. She was so petite. And her pussy was so tight. He wanted to be careful.

When he had lowered her halfway down his shaft, he felt her body stiffen.

"OK?" he whispered.

"Yes, keep going."

When he got three quarters of the way, she bit her lower lip.

"More?"

All she could do was nod.

He lowered her all the way. To the hilt. She was sitting in his lap, impaled by his cock.

She let out a long, satisfied moan.

And she started to slowly rotate her pelvis.

She was loving it. That feeling of being completely filled. That mixture of pleasure and pain.

She leaned back and nuzzled her face against his neck.

He started to slowly thrust into her from below, rocking his pelvis so his cock slid in and out of her.

His hands slid up her body to her breasts, and he held them, her hard nipples sticking out between his fingers. He squeezed her breasts and pressed himself into her.

She lifted her elbows above her head and arched her back.

"Yes, do that! Oh, my God do that!"

She was rocking her pelvis, rubbing herself on him, as his hands caressed her big, beautiful breasts.

He gave her nipples a pinch and she let out a squeal. They were super sensitive and playing with them, while fucking her really deep, was a surefire way to make her cum really, really hard.

And that was exactly what he was doing.

She started to grind against him, arching her back and sticking out her chest. Her mouth was open and her eyes were closed. She leaned against him, her body trembling.

He twisted her nipples and, at the same time, thrust his cock deep inside her.

"Fuuuuuuuuuuuuuuuuuck!" she cried.

He began pulsing his cock into her, rhythmically, while one of his hands reached down to find her clit.

She was moaning now, with every thrust. She leaned against him, feeling the waterfall cover her body.

"Rub me fast, I'm gonna cum!" she gasped. "You're gonna make me fuckin' cum!"

He did as he was told and started to vibrate her clit with his fingers. He squeezed her nipple at the same time.

Her body began to spasm and convulse. He gave her a big, strong thrust and held it there.

He could feel her pussy contracting around his throbbing cock.

"I'm cuuuuuuummmmmmmiiiiiiiiiiiiiinnnnnnnnnnggggggggggg!" she screamed.

He thrust his cock into her again, lifting her.

"Yes! Yes! Oh God yes! Fuck me! Fuck me!"

She was screaming and gasping. With every thrust, it felt like another wave cresting.

He kept it going. Thrusting his cock. Squeezing her breasts. Rubbing her clit.

And she kept cumming. Again and again. Or was it one long, continuous orgasm? There was no way of telling.

When she felt she was on the verge of passing out, she turned her head and found his ear.

"I can't take much more," she gasped. "I want you to cum."

He was breathing hard.

"I'm really close. You've had me on the edge the whole time."

She touched his face with her hand.

"Then do it. Cum inside me."

"You want me to fill your pussy with my seed?"

"You can do it anywhere you want. In my pussy. On my tits. In my mouth. Whatever gives you the most pleasure."

He smiled.

"Decisions, decisions. Well, it felt amazing when you were sucking me. Care to do an encore?"

"I would be happy to do an encore," she smiled.

She slipped off of him and onto her knees, kneeling on the towel once again. She embraced his legs and took his still rock-hard cock into her mouth. All the while, looking in his beautiful, bedroom eyes.

He leaned against the shower wall and watched her. She didn't just give him a blow job, she used her lips and tongue and hands so expertly, it sent jolts of electricity through his body.

And she was watching him the whole time.

Her eyes were so entrancing, looking at him not so much with love but with knowingness. Like she was somehow onto him. Like she got him. I figured out what you want, and now I'm going to give it to you. Not because I'm obligated, but because I choose to.

It was becoming one of the main reasons he was attracted to her. She had a 'I'm not taking any shit from you' attitude that he rarely, if ever, encountered. He knew anything she gave him, whether it was a blow job, or a piece of her mind, would be 100% honest.

She released him from her mouth and began to lick the frenulum, the tender underside of the head. She was using her tongue like an artist's brush, tickling him, making him squirm with pleasure.

She wrapped her fleshy lips around the head, teasing him with her tongue. Then she released him with a smack and jacked him off her hand.

Back and forth she went. Changing it up so the pleasure grew and grew.

He was moaning and writhing now, using mini pelvic thrusts to press his cock into her fleshy lips, spreading them like a pussy.

"I'm gonna cum," he moaned, "I'm gonna cum."

She swallowed him deeply, her lips wrapped around the base of his shaft. Her mouth reminded him of her pussy, warm and velvety, wrapped tightly around him. Sucking the cum right out of him.

His cock exploded. Huge ribbons of cum shot sprayed deep into her throat. His eyes were closed and his mouth was open. Again, he shot his load. And again. And again. She swallowed every drop.

Even after he came, she kept at it. She tickled his frenulum, flicking the tender underside with the tip of her tongue, causing him to jerk and spasm. It made him feel like his orgasm lasted for minutes on end.

She kept it up until he was totally spent.

Wesley sat there, out of breath, wondering how in the world a woman as remarkable as Olivia could also make him feel like that.

After collecting their breath, Olivia wanted to check on Roxanne. They had left her in the hot tub, and while she wasn't falling down drunk, she was definitely feeling it. Olivia wanted to make sure she was okay.

She put on her cover up and went outside. Her cover up an above-the-knee shirtdress, and the outline of her breasts was clearly visible underneath. Her nipples were still standing up and pressing against the sheer fabric.

When she got to the hot tub, it was empty. The water was still and there was no sign of Roxanne. She checked the pool. Nothing. She walked back up the steps to the house.

"She's not in the hot tub. Or the pool. Could she be in the house?"

"Haven't seen her," Wesley said. "Well, she can't have gone far. Let's take a stroll, shall we?"

They checked the house first. She wasn't in any of the bedrooms, the media room, or the living room. They checked all the bathrooms. No luck.

"Let's try the garden," Wesley said.

They walked through the tropical plants and trees, including hibiscus, plumeria, and bird of paradise. Between two breadfruit trees, they found Roxanne laying in a hammock.

She was rocking herself with her foot against a tree trunk.

Olivia ran ahead to rouse her. She snuck up on her and said "boo!"

"Hey," Roxanne said, in a quiet voice.

"I was looking for you. I didn't know where you were."

"I was right here," she said, quietly.

"We were about to about to call missing persons," joked Wesley.

"I was just enjoying some alone time."

"No worries," he said. "I should have known you'd be here. It's one of my favorite spots."

Olivia could see that Roxanne was feeling subdued. She turned to Wesley.

"Could you give us a moment?" she said. "I want to try out the hammock with Roxanne."

"Sure," he said. "I'll see you back at the house."

Olivia crawled in the hammock, lying side by side with Roxanne.

"Everything okay?"

"Fine. Everything okay with you?"

"Yeah, I just took a quick shower..."

"Not that quick," Roxanne interrupted.

Olivia looked at her, and blinked.

"When I got out of the hot tub," Roxanne said, "I went in the house to use the bathroom. I went in Wesley's room. I heard you guys."

Olivia sighed.

"Yeah. We got together. Wesley and me."

Roxanne looked at her, waiting.

"That wasn't the first time you guys did it. Right?"

"Right," Olivia said, sheepishly. "We did it at the waterfall. Yesterday."

"I could tell," she said. "Why didn't you tell me? I thought we were friends."

She said it more in sorrow than in anger.

"I wanted to. But I was afraid of it getting out. And Wesley wanted to keep it secret."

"You can trust me, you know."

"I know I can," Olivia answered. "I'm sorry. I'm usually honest with my friends."

"I want to be your friend, Olivia. But then we come here. And I don't have the full picture. I made a fool of myself."

"I know. I'm sorry. That wasn't fair to you."

"And you made me feel cheap too. You sounded like my mother."

"I'm so sorry. I was feeling competitive with you. But I don't anymore."

Roxanne tucked a tendril of hair behind Olivia's ear.

"So, you guys going steady or what?"

Olivia chuckled.

"I don't know what we're doing. We've done it twice. We've barely talked about it. I have a feeling it's a flash in the pan, but I don't know."

"He was that fast?"

Olivia laughed.

"No, he was good. Really good. I just don't see it going anywhere. And he could decide just to cut me and be done with it."

"Who would ever want to be done with you?" Roxanne smiled, sweetly.

Olivia put her arm around her and nuzzled her face against her shoulder.

"Oh Roxie," she said, her voice cracking.

Roxanne laid her arm on top of hers.

"I like that nickname, by the way. Sounds like a glam rock band from the 80s."

They lay quietly in the hammock for several minutes holding each other tenderly. Then, they walked up to the house, holding hands.

Later, Wesley was in the kitchen, reviewing what was in the fridge, Olivia was sitting at the counter enjoying a glass of wine, and Roxanne was in the shower.

"I have the makings for a nice pasta and we can grill some fish," he said. "There's some broccolini too. Plenty for three. We can eat out on the deck. Al fresco."

He was pitching the idea of them staying for dinner. He was planning to cook.

Olivia enjoyed the idea of this wealthy CEO cooking dinner for them.

"We can open a pleasant sauvignon blanc and watch the sunset," Wesley said.

"Sounds good to me," Olivia said, agreeably.

In walked Roxanne, fresh from her shower. She was back in her coverup, but this time carrying her bikini rather than wearing it.

"I decided to go without. Olivia makes it look so comfy."

Olivia struck a pose.

"Wesley's invited us for dinner. He wants to cook for us. What do you think?"

"Heck, yeah."

"Sounded good to me too."

"I thought we could open a bottle of white wine and sit on the deck. If the sunset cooperates, it should be lovely."

He pulled two more wine glasses out of the cabinet.

"Might as well get started with these."

He poured out the wine and handed a glass to Roxanne.

"To high winds and mermaids!" he said, holding out his glass. They clinked glasses and took a sip.

"Why don't you two take your wine out on the deck and relax. I've got some cooking to do."

They headed out to the deck that adjoined the living room. In their mini cover ups, and with the afternoon sun setting behind them, Wesley could clearly see the silhouettes of their naked bodies.

"Just put your feet up and make yourself comfortable," he said.

The view from the deck was amazing, stretching up and down the coast. His house was well situated, with a wide-open view of the ocean yet complete privacy. They arranged their chairs so they faced the sun, put on their sunglasses, and settled in.

Both women hiked up their cover ups to expose their long, bare legs to the sun. Lounging in their shades, holding their wine glasses, they looked like models in a fashion magazine.

"Can't sunbathe like this at Kona Village," Roxanne said, taking a sip and pulling her cover up above her hips.

Olivia laughed.

"Workin' on our all-over tans!"

Roxanne laughed, pulling the fabric all the way up to flash her tits.

They both laughed.

"It'd be so great living here," Roxanne said. "You could nude sunbathe all day long and no one would know."

"Go for it," Olivia laughed, "I'm sure Wesley wouldn't mind."

"Mind what?" Wesley asked, setting down a plate of veggies, crackers and goat cheese.

"If we nude sunbathe," Olivia answered, matter-of-factly.

"Absolutely," he said. "This is a clothing optional resort. I often lay out here in the nude."

The women glanced at each other. Roxanne took a sip and waved her hand dismissively.

"Oh, I've already taken advantage of the no-clothes policy. Down in the hot tub."

"You did?" Olivia asked. "After we left?"

"Sure. It feels so much better when you're totally naked. And when someone tells you about the perfectly positioned jet, all the better."

Wesley looked at her with eyebrows arched.

"Ohhh, did you spend some quality time with our good friend Mr. Jet?"

She gave him a sexy smile and took a sip of wine.

"Well, let's just say your hot tub and I are practically engaged at this point."

Olivia and Wesley both laughed.

"Well, you're welcome to come over and use it anytime," he said graciously. "What you should really try ... no, never mind."

He started to get up to leave. She reached her hand to stop him.

"Wait. What were you going to say? What should I really try?"

"Forget it. Just a silly thing."

"No, you can't leave me hanging like that," she smiled. "You said I really had to try it."

Wesley sighed.

"I was going to say," Wesley said, "that you should really try a threesome - you, the jet, and someone doing you from behind. Especially someone who's well-endowed. Now that, I'm told, is truly mind-blowing."

Olivia howled as Wesley stood up and walked back to the kitchen.

Roxanne squirmed in her seat.

Wesley served them dinner al fresco. He brought out a candle and place settings and the sunset put on quite a show. It was quite lovely.

He kept their glasses filled with white wine. The warm night had them feeling relaxed and made the wine go down easily.

Over dinner, the conversation turned to work. Wesley let slip that ATI had a scoring system for evaluating all the guide candidates. Every activity, every exercise, every deliverable was scored.

"We have both qualitative and quantitative scores which we track on a daily basis. That way we can help ensure that hiring decisions are free of bias. That's part of the reason we have such a diverse team."

"So, we're being scored?" Olivia asked. "Already?"

"From day one."

The women looked at each other.

"So, how are we doing?" Roxanne asked.

"I can't reveal that, I'm afraid. It's confidential."

"Come on, just a hint?" asked Roxanne. "Are we at least on the right track?"

"I can definitely say that you're on the right track. Alexandra was very impressed with the way you handled the horseback riding. And I thoroughly enjoyed the waterfall hike with you, Olivia. I'll just summarize by saying you're trending positively across multiple metrics."

"Awww!" Roxanne said. "I've always wanted to trend positively!"

Olivia leaned in, a sardonic expression on her face.

"Please tell me there's a leaderboard! I can see our names up there! We want to be number one!"

"We're number one! We're number one!" Roxanne chanted with Olivia joining in.

The wine had indeed been flowing.

"Being considered for a new job is not an easy task," Wesley said. "I appreciate your patience."

"This is nothing," said Roxanne. "When I was acting, I'd go to auditions three or four times a day. Rejection was my middle name. I worked more days doing non-acting jobs than acting jobs."

"Like what kinds of jobs?" Olivia asked.

"You name it. Waitressing, paralegal, personal assistant. I even worked for a while as a masseuse. Or a massage therapist, if you please."

"Really? Did you work at a massage parlor?" Wesley asked.

"No, I mainly did outcalls. You know, go to people's homes, hotel rooms."

"Did it ever get scary?" Olivia asked.

"It sometimes got a bit dicey. But you learn how to handle those situations."

"Like how?"

"You know. You learn how to read people. And how to change their behavior, if needed."

"For example?"

"There was this one time. I was in a house in El Segundo. I'd brought in my table and was giving this guy a massage. He was a big, buff dude. About Wesley's size. Anyway, he's lying on his stomach and I got the towel on his butt and I'm working on his lower body. He's pretty muscular so I'm on top of the table, using my body weight, pressing nice and deep. And I'm sliding my hands slowly up and down his legs. Over the backs of his thighs. And then his upper thighs. And then I hear his voice. He asks me, would I mind massaging his butt. So, you know, he asked nicely, and he's a good-looking guy, so I say, okay. So, I'm kneeling on the table, between his legs, and I start rubbing his butt under the towel. You know, discreetly. And he seems to be enjoying it so I start sliding my hands over his ass cheeks, working his glutes. Then, when I go to get more oil on my hands, the next thing you know, the towel slides off. And I mean all the way off. Onto the floor. So, here I am, on top of the table, both my palms full of oil, and he's lying there bare-assed."