Island Vacation Ch. 17

Story Info
Jen goes sailing one last time.
5k words
4.77
7.1k
8

Part 17 of the 19 part series

Updated 12/14/2023
Created 06/25/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
imaging
imaging
309 Followers

She was surprised by the darkness. Jen wasn't sure what time it was, but she knew she was wide awake. There was an energy pulsing through her that shoved aside the idea of any more sleep. She listened to Tim's deep breathing. As much as she wanted to, she decided not to wake him.

Sliding gently out of bed, she stepped quietly to the bathroom, grabbing the plastic bag from the shop on the way. It was easier and quieter than rooting around in her suitcase.

5:02 AM. She wasn't sure what time she had gone to sleep, but it made little difference. She was awake. She turned the water on in the shower, relieved herself, then stepped into the warm water. Turning away from the controls, she laid her head back, letting the warmth massage her scalp and flow down her hair. This was a moment she would have a hard time repeating at home. Showers were rushed affairs. Baths were out of the question.

Leaning her head forward, the spray massaged her neck, and she could feel the cascade down her back and curving around her cheeks. She paused long enough to realize that it was making her tingle. Or maybe she was already tingling before she began her shower. She thought of Tim's cock, filling her and pounding some unseen barrier last night. The tingle elevated to a slight buzz.

She slipped a finger between her lips to find that she was getting wet. Or maybe she was still wet from last night. As good as it felt, she decided not to pleasure herself. Maybe the sound of the shower would wake Tim and he could finish where she had just begun. She took her time, lathering her skin, feeling every inch of herself, and even squeezing her stiff nipples as she spent extra time washing her breasts. The same breasts she had now shown to strangers. The same breasts that strangers had fondled. The same breasts that Kate had enjoyed in the hot tub.

The buzz found another level.

Even patting herself dry was arousing. Her skin was more sensitive. Her imagination more vivid. Her heart raced in her chest.

She peered out the bathroom door into the darkness. No movement. The slightest hint of light was peeking around the curtain in front of the patio door. Tim's breathing was unchanged.

She pulled the door closed again and reached for the bag. Two garments were held together by a small strand of plastic that was easily dispatched with her fingernail clipper. The shorts were snug, but they appeared to be designed that way. They were some sort of nylon that was supposed to look like silk. Green. Probably her least favorite color. The crease between her ass cheek and thigh was visible. She liked how they made her feel, both by the way they squeezed her and how they made her ass look.

The matching tanktop was white with a Jamican flag surrounded by the words "Jamican Vibes". It was the ultimate tourist get-up. But unlike a normal tank top, the fit was loose, and the "arm holes" in the top were so large that any movement at all revealed her breasts. It was clearly designed to be worn over something else, but she suspected that the guys at the shop would prefer that she wear it alone. She looked at the tacky outfit again, then looked past it, studying herself in the large mirror. At first glance, she looked a lot like the woman she had seen in the mirror on the airplane a week ago, but something was different. The outfit was an obvious change, but she wondered if she didn't see something in her eyes that wasn't there a few days ago.

"Not the time for self-reflection," she thought, amusing herself with the pun. That energy was still pushing her, and she needed to move. No one would be out at this time of the morning, so tacky, revealing, or otherwise, she was going out.

She found the keycard in the semidark room and slipped out the front door.

The smell of the tropics enveloped her as soon as she was outside. Sea air, the sweet smell of flowers, the aroma of someone getting an early start on breakfast. She rounded the building and made her way past "their" small patio. She noticed the chair and remembered the neighbor's wave. She stopped for a moment, looking at the large glass doors and considering the view that others had enjoyed from that very spot earlier in the week. The buzz was back.

She followed the walkway, down the path toward the gentle waves. The sun was rising behind her, dying the cloudless sky over the water with a deep blue luminance. She smiled as she thought about her first trip down this path. The chairs and chaise lounges were all empty now. Soon they would be filled with the semi-naked bodies that had offended her delicate sensibilities only a few days before.

She took a seat nearest the water's edge, letting her toes dangle into the sea as it moved in and out with small, gentle waves. The lapping of the warm water felt sensuous to her, too. She closed her eyes and enjoyed the sensation. Was it possible that even this feeling on her toes was somehow affecting the vibration between her legs?

A gull's cry to her left drew her attention in that direction. She lowered her eyes back to the beach, landing on the spot where she and Tim had made love. That had been an amazing day. Her mind drifted to the fantasy of her audience, stepping toward her, filling her.

She suddenly realized that her hand had slipped between her legs. She squeezed her mons through her tight shorts. The pressure did nothing to settle the vibrations she was feeling there.

Walking, she decided, was the better course of action. The sun was now up, and the ocean reflected its golden tones across the muted blue sky. She wondered if Tim was awake yet. She reached the top of the path, paused, and turned left rather than returning to her room. Soon she was crossing the cool grass. Mickey and Kate's room was up that hill. She looked toward it, wondering who was living behind that fence today. If they only knew what had just happened on that bed and in that hot tub!

Within minutes, she arrived at the other beach. Workers were beginning their day. A young man raked seaweed out of the sand. Another worked with a short, busty girl, arranging lounge chairs.

"Good mornin', Miss Jen." The voice called out from down the shore where three young men were lining up sailboats and paddleboards. "You're out early this mornin'."

The faceless form was walking toward her now. Oh, what was his name?

"It's Daniel, your captain from your sail the odder day."

"Of course, good morning. How are you?" She watched his eyes drop to her chest.

"Much better now, thank you!" His smile was completely disarming. "And where is Mr. Tim?"

"Still asleep, I think. At least he was when I left."

"Like he should be, it's vacation, yeah?" She could feel him devouring her with his eyes, but that smile made it all feel so innocent.

"Well, if you want, I take you out. This is my favorite time for a sail. The water is like glass. So peaceful, you know?"

Her heart skipped.

"Umm. That sounds nice. Let me see if Tim's awake. Maybe a sail before breakfast would be nice." She thought she might have seen a little disappointment in his face, but his smile and his tone never wavered.

"OK. I'll get it everyting ready for you."

Jen walked to the room quickly. Tim was in the bathroom when she stepped inside. The door, of course, was open.

"Where were you?" He asked over his shoulder. "I was about to come looking for you."

"Just on a walk. Brush your teeth and throw on your trunks. We're going sailing."

"Oh, OK," he replied. "I was actually kind of thinking that maybe we could..."

She interrupted him. "Did you really like what you saw yesterday?"

He looked confused. "Yeah." His response sounded more like a question.

"And the store, you liked that?"

"Very much." He flushed and turned to her.

And so if I... you know... did something else you'd be OK?"

"Like going sailing?" He was waking up now. "And where did that come from? Did you wear that out?

She giggled. "Ridiculously tacky, isn't it? It's from our friends at the store. And yes. And yes."

He narrowed his eyebrows as he looked her up and down. "And you want to go sailing in that?"

She nodded.

He spun on his heel and grabbed his toothbrush. "Find my trunks please".

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

Tim wondered exactly what Jen had been up to that morning. How long had she been gone? What did she do while she was out? Who was she with? He knew they had decided that she would do nothing unless he was there, and he trusted her. Still, this behavior was out of the norm. Hell, he thought, all of her behavior had been out of the norm this week.

He watched her ass as she led them back to the sailboats. That fabric seemed to glow in the early morning sunshine. It hugged her ass, revealing the cleft between her two rounded cheeks. He wondered what it revealed in front of her. The top, on the other hand, left nothing to wonder about. Every movement and breeze gave a generous peek at one breast or the other. Somehow it was even hotter than seeing her naked out here.

He was so focused on his wife that he was unaware that they had reached their destination so quickly. Daniel's greeting was warm and enthusiastic.

"It's nice to see you again, Mr. Tim!"

Tim suspected that Daniel could have cared less about seeing him. He saw the man's eyes devour his wife's exposed body.

"And Miss Jen, beautiful as always. Everyting is ready right over here."

Tim followed his wife, who followed their host. Again, his eyes dropped to see her tight butt, wrapped in that fabric. He could hear her telling him that she could never wear it at home. He doubted it would even make it into their overly-packed bags back in the room.

They took their seats on the left side of the boat, facing the sail in the middle. Daniel and a coworker pushed the craft into the water. Tim couldn't help but notice the man's eyes never left Jen. He turned to his left to see her and understood why. Her right breast was nearly completely exposed under the flimsy excuse for a shirt that she was wearing. He thought about the men who gave it to her. Too bad they couldn't enjoy the results of their generosity.

Daniel jumped onto the side across from them and pulled the sail into the wind. There wasn't much of it this morning, but soon they were gliding across the tranquil water into the deep. There was some lame attempt at small talk. Daniel learned that today was their last day and that this, other than brunch, would be their last activity at the resort.

Tim was aware that Daniel's attention was mostly on his wife. And she did nothing to cause him to look away. Unlike their first meeting with Daniel, there was no cap to hide her eyes. Nothing she did was subtle. She put her hands on the hull behind her, leaning back, causing her breasts to push up into the thin white fabric of her shirt. She stretched her legs, pointing her toes directly at Daniel as she did.

The silence was immediate. Only the sound of the water gently lapping at the hull filled the air.

"Tim," her voice startled him. "Wasn't Daniel teaching you how to sail before?"

Daniel laughed. "I tried to, but I think he was a little distracted."

"Well, you're not going to get another chance like this? Why don't you take his place and let him show you?"

"Um," he was slow to reply. "OK. If you're sure."

"I am. But it's up to you." The expression that he had seen last night was there again. Under the bright morning sky in the middle of open water. His dick stiffened at the thought of whatever might be in store.

"I guess I should move over there, then?" He asked Daniel.

"Well, it would be better if we changed places. Too much weight on one side."

Tim saw that the rod Daniel was using to steer the craft ran from one side of the boat to the other. He suspected that he could have simply rested his right hand on the tiller, but he wanted to see this man next to his wife as much as he figured the two of them did.

Sliding across the trampoline, he wondered if Daniel was going to get as close to Jen as the store clerks had. He wondered if maybe he already had.

It took all of two minutes for Daniel to explain how to steer the boat and keep the slight breeze in the sail.

Then the silence returned.

"Would it be a problem if I stretched out across there again?' Jen asked, gesturing toward the taught fabric in the middle of the boat.

"No ma'am," Daniel smiled. "Enjoy the sunshine while you can!"

Jen rose to her knees and reached for the bottom of that skimpy top. Tim felt an immediate lump in his throat. She paused before pulling it up.

"Do you mind?"

"Not even a little," Daniel beamed.

She slid it up, slowly, facing Daniel. Her back was mostly turned to Tim, but he could see the expression on the Jamican's face as his wife's breasts came fully into view.

"Mr. Tim, you are one very lucky man! But you know that, right?" He never took his eyes off her.

Jen dropped her head and Tim could imagine her blushing at the young man's praise.

"You say that about every woman that comes out here." Her tone was light.

"Well," Daniel grinned. "Maybe I do. But they don't all look like you. You are a beautiful woman. Truly."

She turned toward toward Tim, smiling, then crawled to him. He saw Daniel's eyes locked on his wife's ass. He could only imagine the view those shorts were giving him. He knew how much of her cheeks were exposed when she walked, so in this position, he was getting an eyeful.

Jen rose up and kissed Daniel on the cheek. There was an unspoken sentence in her eye contact as she leaned away from him. She retreated a foot or so and then turned to lie on her back, her head at her husband's feet, her legs pointed toward Daniel.

She closed her eyes and rested her right hand on her flat tummy. Her left rested at her side. She paused a beat before beginning to slide her hand upward, slowly, intentionally, toward her chest. Tim's erection was immediate. He glanced up long enough to see the young man was responding in the same way.

Daniel suddenly turned his head toward the front of the boat, then to the shore a few hundred yards away, then back to the front.

"Mr. Tim, do you see that large rock that looks like it has a ball on top?"

Tim saw something that roughly met that description.

"Go straight for that," Daniel said, now looking directly at Jen.

She caressed her left breast, cupping it as though she were getting a feel of it for the first time. Tim watched as her manicured fingertips found their way to her stiff nipple. She pinched it gently and the pleasure registered on her face. Within a minute, both hands were at work, squeezing, scraping, pinching.

She took her time and the men could see her chest reddening as she played with them. After a bit, her right hand slowly began sliding back down toward its original resting point. But she never paused as she moved past her belly button, finding the elastic waist of her shorts, She straightened her fingers and Tim watched those fingernails disappear beneath the shimmering green fabric.

Daniel quickly looked toward the front of the ship, then reached to loosen the sail. If there was a breeze Tim wasn't aware of it, but he could feel the slight momentum of the boat slowing, allowing him to fully turn his attention to his wife and her bold display. By now her waistband had worked its way down to her hips, revealing the back of her hand and the knuckles at her fingers. The top of her trimmed pubic hair was visible, and Tim was certain that Daniel could see the outline of his wife's fingers as she pleasured herself.

Her soft moans could be heard above the quiet sounds of the water licking the hulls of the boat. He watched as a small wave of pleasure rolled over her, creating what he was sure was a small orgasm. His dick pressed hard against his trunks and he quickly decided to lose them. Jen noticed the motion and opened her eyes to see his erection hovering over her. She smiled at the sight, nodding gently.

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

She wanted it. Right there in front of this stranger. Maybe his presence made her want it even more. She wasn't sure and she didn't care. Her fingers continued to dance through her warm slit, both for his pleasure and hers. She wanted her husband's dick for the same reasons.

Tim knelt next to her head and she turned so that he could feed it to her. It was a little awkward at first but they quickly found the right angles. Tim reached across the top and down the back of her head, holding her there as he found a gentle rhythm. Like the last time, she felt her body quickly respond to his control.

The shorts were in her way, so she pushed them down further, then tried to rid herself of them with a series of uncoordinated movements of her legs.

"May I help?" Daniel asked.

She couldn't answer with Tim's cock in her mouth, so she simply signaled a "thumbs up" and then put her hand back to work. Now with her knees spread wide, thrusting her sex upward to meet her fingers. She was completely aware that she was pushing her pussy directly at Daniel. She wanted him to see. She hoped he could peer all the way inside her. Honestly, she hoped he would do more.

The impact was abrupt and surprising. She was convinced that she had bitten Tim's cock as both of their weight shifted from the sudden stop. She rose to her elbows to see that the boat had collided with the shore. As it did, Daniel stepped off the side and pushed the craft onto the beach. Tim quickly moved to help him. She noticed that the location was desolate, marked by more of those large rocks they had seen the other day.

"Nobody gonna bother you here," Daniel smiled.

She narrowed her eyes at the young black man. "Take them off". Her voice was soft but demanding.

She watched as he released his member into the sunlight. It was erect and proud, the tip pushing toward the risen sun. A large stream of precum fell from its pointed tip. She scrambled to her knees and moved quickly to the edge of the boat, catching the suspended drop before it fell. She looked him straight in the eye as she rose on her knees cupping her palm to her mouth and licking it clean. It was sweet. She wanted more.

The smile was gone. Daniel's eyes were locked on her body. He studied her breasts, then shot Tim a glance. Maybe a question mark in his eyes? She could feel Tim nodding.

Again the young man's eyes moved to Jen's breasts, then back to Tim. Another unspoken question.

He turned to Jen, with a mixture of desire and uncertainty in his eyes. She smiled and nodded.

Daniel raised a hand, inches away from Jen's breast. He pointed with the other finger as he raised his eyebrows again.

Another nod.

He lightly brushed her right breast, causing her to gasp softly. Then she placed her hand on his, encouraging him.

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

Neither of them saw it, gratefully, but Tim came at the sight of this man touching his exposed wife in such an open setting.

He watched as the young Jamaican felt one tit, then the other, exploring the willing woman in front of him. At one point, he took both of her breasts into his hands and began to massage. Tim heard a faint coo from his wife.

Daniel got braver, leaning to kiss Jen's left breast. Then again. Tim noticed that his dick was as hard as it had been before his eruption a few minutes ago. He realized that he should have been jealous. Or protective. Even angry. But he was none of those things. Seeing a complete stranger give pleasure to - and get pleasure from - his wife was hotter than he could have ever imagined. He wondered what that meant for a second. Then the thought was overrun by what was happening right in front of him. He could think of nothing other than the man fondling his wife outside in broad daylight.

imaging
imaging
309 Followers
12