Island Vacation Ch. 18

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Jen rides back to the airport.
4.1k words
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Part 18 of the 19 part series

Updated 12/14/2023
Created 06/25/2023
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She double-checked her tote bag. The jeans and sleeveless button-up were there, right where she left them. Had it not been for Kate's trip to the horses they would have never come out of the bag this week. She hoped the jeans had aired out well enough on the patio to allow her to change back into them on the plane.

The sundress was the same one that had come out of that same bag a week ago in the tiny airplane bathroom. As Jen checked it in the mirror one last time, it looked very different to her now than it did then. It wasn't nearly as scandalous as she remembered it. It might make it back to her closet at home, after all. The rest of the look was largely the same as it had always been. Her hair was carefully styled. Her makeup was light and clean. Her skin was a shade or two darker than when they had arrived.

"And no tan lines," she smiled to herself.

......................................

Tim was hanging up the phone when she stepped out of the room.

"Everything is set. They arrive in a couple of hours. Ted and the others will take them to dinner and we'll meet them tomorrow..."

The phone rang, interrupting him. It was the front desk informing them that their ride was here.

They grabbed their bags, took one last look at the room, kissed quickly, and headed into the sunshine.

When they rounded the walkway toward the entrance, Tim was surprised to see Richard waiting for them at the van.

"Well, hello, my friends! You not gonna stay with us forever?" His smile was broad and warm.

"That would be great, but someone has to go home to feed our kids," Tim joked.

"Hello, again, beautiful lady. I am glad I get to see you again!"

"I bet," Tim thought.

"Okay, nobody else goin' with us today, so you can sit up close," Richard said as he slid their bags toward the back of the van.

"Nobody?" Jen asked, remembering how many hotels they stopped at to drop passengers off when they arrived.

"Nope. Nobody go home on Saturday. So we have plenty of time to enjoy the ride."

Tim thought he noticed something extra in those words. Or maybe it was the tilt of Richard's head as he said it. Or maybe his imagination was just running away with him.

He did not imagine Richard's hand on his wife's ass as he "helped" her into the van. Nor did he imagine her less-than-subtle smile as she turned to him while they took their seats. Both Richard's boldness and his wife's reaction caught him by surprise. He sensed that he had already begun to return to "reality mode."

Apparently, Jen had not. As they pulled out into the road, she took his hand in hers. He thought the action was sweet. Maybe romantic. Then she laid it on her left thigh. Just below the hem of her dress. He looked up to see her smiling at him. She moved her hand away, leaving his there.

"Will we be stopping again on the way to the airport?" she asked Richard.

"We have time, pretty lady. If you want to stop somewhere we can. You wanna see the market and buy something for your boyfriend?" he laughed.

"My boyfriend is right here," she patted Tim's leg. "And I don't think there's anything else here that I haven't already given him."

Richard laughed knowingly.

Tim enjoyed seeing his wife bantering with the driver. It probably shouldn't have by this point, but the tone and the topic surprised him. He had never heard any sort of innuendo from her. Not even when it was just the two of them. His dick heard it, too, and was beginning to respond.

It also surprised him to see that Richard still had things to point out to them on the return trip. As he pretended to listen, he slid his hand into the crevice between Jen's thighs and began to gently massage the left one. For the next ten minutes, he slowly moved upward, sliding the fabric out of the way as he did.

Jen's response was just as subtle. Little by little, she opened her legs. It was almost imperceptible at first. He noticed that Richard looked up into the mirror often, but unless he could see their laps, he would have been unaware of what they were doing. Jen looked out the window to her side, her face largely expressionless.

..................................................

Was she teasing Tim or Richard? She wasn't really sure. And she didn't really care. The only certain thing was that she was enjoying herself. Her pussy was still on high alert. Even after a shower and a delicious brunch and tossing the rest of their things into their suitcases, she was still thinking about that boat ride. She still wanted more. She just wasn't sure how much more.

When Tim finally reached his target, she gasped at the same time that he did. For different reasons.

"Forget something?" he whispered.

She just smiled and raised her eyebrows at him, then turned her attention back to the passing scenery. She was wet and grateful for the complete access she had given him. Panties would have just gotten in the way.

It was harder now to keep her composure. Her pussy was on fire and even the slightest touch sent jolts through her entire body. She looked up at Richard's mirror to find him looking directly at her. She started to break eye contact but then thought better of it. She smiled as she spread her legs wider, allowing Tim to dip a fingertip into her wet hole.

Emboldened, she stretched her hand across his lap, finding his erection through his pants. She squeezed his shaft, coaxing a sigh from him.

She caught the motion out of the corner of her eye. When she looked back to Richard's mirror she could no longer see his face. He had redirected it. Lower. Improving his view.

She spread her legs even wider now, slipping her own fingers to her clit while Tim worked his way deeper inside. She wanted to turn toward him, giving him better access, but she didn't want to ruin Richard's view.

She continued stroking Tim's dick the best she could through that fabric. Finally, he reached down and released himself for her. He was slick with pre-cum and after a couple of fingertip strokes, she moved her hand to her mouth and licked them clean.

Suddenly, Richard hit the brakes hard. Two horns blared from somewhere close and the couple were shaken out of their stupor.

"Sorry." he apologized. "I was distracted. It was very stupid."

Now or never, she thought.

"Maybe there's a place where we can stop?"

Tim raised an eyebrow at her.

"Um. Maybe 10 minutes," Richard replied.

It seemed like two hours.

He turned into a dirt road that led them through a large grove of broadleaved trees. About a hundred yards in he turned again, stopping in a small clearing. Jen noticed small bananas growing on the tree out her window.

"OK. Now we're safe." Richard shut off the engine. 'You want me to wait outside, or maybe you want to enjoy nature again." He winked at Tim. Jen felt herself blush.

Tim looked to her. Before he had a chance to speak, Jen responded, "No, it's fine right here. And you can stay. I mean, it's not like you haven't already seen me ... you know."

She looked at Tim again. He looked as though his eyes were going to pop out of his head. Like him, she wondered what had happened to his wife over the last week.

"See what you started?" she teased him, then leaned over to kiss him. He was a little slow to respond, but soon his passion matched hers. Their tongues reached for one another, hungry and impatient.

She felt his hands on her breasts and stopped kissing only long enough to pull the straps off her shoulders and push the fabric down to her waist, revealing her boobs to her husband's eager hands and the driver. Exposing them made her heart race. They clutched and grabbed at each other like horny teenagers. Tim eventually found his way between her legs again and flicked at her knob. The feeling was electric. She laid back against the window, turning sideways on the bench seat, her left leg over the back, her right foot on the floor. Tim dropped to his knees and buried his face in her soaked crotch. She knew that in this position, Richard could see everything.

And she wanted him to.

It took less than a minute for her to cum. She held back nothing. Digging her fingers into Tim's hair, she ground into his face, savoring every sensation: his stubble on her inner thighs, his tongue trying to fuck her hole, his nose pressed against her clit, her opened pussy, completely exposed to another stranger, allowing him to see her at her most vulnerable.

When it subsided, they changed places. She glanced at Richard and saw the glazed lust in his eyes. She took her time, leaning in slowly to kiss the head of her husband's dick before finding that spot she discovered last night with her tongue. Finally, she opened her mouth and took him as deep as she could, savoring the taste and smell. She sucked his cock not only for his pleasure and Richard's enjoyment but for herself. She loved every part of it: the taste, the nastiness of doing it in this van, in this place, in front of another man. She loved the fact that she was the center of it all. In her mind, at least, this was all about her, and she couldn't have been happier.

..................................................

Richard moved out of his seat, working his way around Jen, and sitting in the bench behind them. As he began to sit, he opened his pants.

Apparently, he dropped them on the way down, releasing his cock. Tim saw Jen turn to see it. She stopped sucking him, pausing long enough to take in the view before turning back to Tim, her mouth gaping and eyes wide. Tim's view was restricted by the back of his seat, but he had a pretty good idea of what she must have seen. After all, stereotypes get started somewhere, right? It was only reasonable that a tall, lanky black man would be well endowed.

Tim tried to get a look, but all he could see was Richard's head and shoulder. There was something about his body language that caused Tim to think that he must have been playing with himself.

Since Jen was so clearly distracted, he sat up, dropping his eyes to Richard's lap. His suspicions were confirmed. Long, thick, and not even completely erect yet.

Jen looked up to her husband with an unspoken question in her eyes. He simply shrugged, but he was eager to see his sexy wife suck a second stranger's cock today - especially one that looked like this!

She slid over to him, pulling herself tall on her knees, leaning over that growing black column. She wrapped her fingers around it, almost as though she were getting the measure of it. It looked weighty in her tiny hand. She surprised him by beginning at his balls. A tentative lick, followed by another. Then a subtle suck, pulling one testicle into her mouth. Then she stroked his shaft. First with one hand, then with two as it stiffened fully. Even with two hands wrapped around it, the head extended beyond her grasp.

When she finally tried to take it into her mouth, she could do little more than stretch her lips around the tip. Her attempt was valiant but unsuccessful.

"Maybe I could taste you," Richard suggested. Looking at Tim he added, "If that's alright."

There was a quick glance between the two of them. Their silence indicated their mutual consent.

Richard slid off the bench, sliding to the side to make room for Jen. She yanked off her dress, handed it to Tim, and set her bare ass down on the seat. She laid back, resting on her elbows, allowing Richard to lift her legs into the air. He studied her slit for a beat, then dove in. All that Tim could see was his nose pushing into her slit, but he could hear the work he was doing with his tongue.

Jen seemed tense at first but soon she relaxed and Richard found the spot and a technique that began to increase her breathing. Soon she was moaning softly and reaching for his head. Her free hand pinched her nipple and Tim reached over to play with her other breast.

The first orgasm came quickly after that.

Richard changed his technique, pulling his nose out and letting the tip of his tongue find a rhythm on her clit. He fluttered it from side to side, stopping occasionally to suck or nibble, then returning to the fluttering action, this time up and down. He pulled Jen's right leg toward Tim, nodding toward it. Tim took the cue and held his wife's leg, allowing Richard to slide a slender black finger into his wife's cunt. Soon a second followed. Then a third. The orgasms were slight, but frequent. And it seemed that Richard was playing it that way on purpose. He knew how to bring her gently to the edge, but never let her go completely over it.

"More?" he asked softly.

Jen nodded immediately and Tim could feel her trying to spread her legs wider.

He looked at Tim. "I have a condom in my bag." He jerked his head toward the driver's seat. Tim turned to see a small backpack lying on the console. He didn't hesitate.

He thrust the bag into Richard's hand, then looked back down at Jen. Her eyes were closed as she played with her pussy, waiting for Richard.

Tim's brain was caught up completely in the moment. He was unable to think. Or to react. Later he would wonder exactly how this moment passed with no conversation between the two of them. No questions. Nothing in him could imagine any outcome other than the one that they were hurling toward.

He took in the sight of his aroused wife. Jen's pussy was drenched and swollen and red. Her nipples were as stiff as he had ever seen them. Her body was completely ready to be taken by another man.

And he was absolutely ready to watch it happen.

Richard stretched the jumbo condom down his erection. The rubber ended well before reaching the base of his dick. Taking both of Jen's ankles into his hands, he quickly pulled her toward him, sliding her ass across the seat, allowing him to spread her legs even wider. Now with her completely open to him, he aimed his impressive member at Jen's opening, pausing when he made contact. Her eyes opened wide and she seemed to be holding her breath. Lowering his hips slightly, Richard slid his dick up the valley of her slit, across her clit, and stopped only when his balls hit her opening.

"Don't tease," she begged.

He smiled; those white teeth shining across his lean face. Shifting his stance slightly, he pressed at her opening. The tip forced its way into her. Jen gasped at its fullness.

He pulled it back out and reentered -.a little more forcefully - but only getting another inch or so deeper. Jen moaned her approval, trying to slide her ass cheeks closer to him.

Without taking it out again, he began to slowly work it in and out in small movements. Tim could see her juices coating the condom. Bit by bit he watched it disappear. It may have taken a full minute. Perhaps more. Tim was mesmerized. His own cock was rigid and he could feel the cream escaping from its tip. He pulled it out of his pants, almost afraid to touch it.

Richard worked his hips in a circular motion now, causing his shaft to burrow into Jen's tight opening. Her moans grew louder with each new centimeter of Richard's turgid dick. Then they became gasping whimpers. Her eyes tightly closed. Her hips rising and thrusting toward her silent aggressor. She bit her bottom lip with pleasure.

Richard stopped his motion when his cock was about halfway up Jen's cunt. He leaned forward and kissed her on the mouth. It was deep and passionate, and Jen moaned and sighed as he worked his tongue between her lips. Then he sat up, smiled again, and with one intentional movement began to remove his dick. Tim noticed the white goo from his wife's cunt marking it's depth. Then, just before pulling it completely out, he suddenly changed course and buried it completely in her.

Jen's shrieked now, louder. "Oh, yeah! Oh my God, yes!"

He seemed to bottom out, then shoved his hips forward, jabbing her, as though to be sure that she had taken all of it.

"Like that?" He smiled.

She nodded, her mouth open wide, gasping for air. "Fuck me," she whispered.

And so he did. He started gently, sensuously gliding from tip to base, where he added that extra "push" and back again. The first few strokes were slow and deliberate. Tim couldn't look away. He watched the long black shaft disappear into his wife, heard Jen's grunt at that push, and then watched the process repeat itself. It was on the third or fourth repetition that he noticed the bulge moving up and down her flat tummy; that big cock tunneling in, finding its spot, and retreating.

Bit by bit Richard picked up the pace. Spreading her legs wider he began to fuck harder. Faster. Each thrust was more fevered than the last. Jen did her best to match his rhythm, but in the end, she could do nothing but close her eyes and take him. The sounds found their own rhythm, too. The slapping of Richard's thighs on Jen's tight ass cheeks, matched by his grunt and immediately followed by Jen's sexy whimper. He leaned forward, pushing her legs toward her chest, which caused her pussy to pivot upward. Now he bore down into her, banging even harder. Jen began to moan, interrupting herself with little gasps of encouragement.

"Uh huh... there.... Yeah... like that.... O God..."

She opened her eyes and met Tim's.

Bliss. That's the only word he could think of. The lower half of her body was being assaulted by a long, thick, insistent staff that would have appeared to have been painful, had it not been for that look on her face.

She smiled at him gently and closed her eyes again.

Her orgasm grew from somewhere deep within. Like a distant train, the sounds were soft, but certain. It took little time for both the volume and the intensity to grow. By the time the inevitable was near she opened her eyes again and looked directly at her husband.

"Yes. Fuck. YES! Oh my God, Yes! Fuuuck!"

Tim had to release his grip on his cock. He looked away, hoping that might help him maintain his "composure", but the sounds coming from the seat behind him wouldn't let him escape.

Richard pulled out as she finished her climax. He watched with Tim as her breathing slowly came back toward normal.

"Oh, pretty lady, you are damn hot. Mr. Husband, do you want some, or should I finish?

Tim wasn't ready for the show to be over. "Finish," he said, his voice barely above a whisper.

He saw Jen smile.

"Then turn around."

Jen sat up and turned to face out the window, pulling her knees onto the seat. Her pussy was puffy, red, and gaping. Tim saw her juices escaping to coat her thighs. He pulled himself back into the seat in front of her, his head at her ass so that he could watch that black cock drill all the way into his wife's sweet pink pussy. Richard took less time now, getting up to full speed quickly. He pounded her so hard that Tim was concerned she might hit her head on the side of the van or the window, but Richard's strong arms held her hips tightly, keeping her in place.

After another orgasm - and another streak of words that still shocked her husband - Richard slowed his pace. Now, somehow, his thrusts seemed to be deeper as he worked his hips down and under her with every forward thrust.

Tim watched as he pulled his thumb to his mouth, licking it with his long, pink tongue, before wrapping his lips around it. He never took his eyes off Jen's ass as he took that thumb and placed it at the puckered opening of her asshole.

Before Tim could speak, he pushed it forward slightly, eliciting a new sound from Jen. He continued to tease her hole while he fucked her gently. The thumb seemed to disappear all at once. First, it was there, sideways, the fleshy part pushing at her hole. Then it was gone, entirely, buried up the webbing that joined it to the hand. Jen seemed to push back harder into it.

Tim was trying to mentally record every image. He was certain that these were moments he would never live again, so he desperately wanted to remember every detail. He felt detached, somehow, even though the scene was playing out inches away from him. He could smell the sex. He saw everything, but it seemed distant from him.

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