Caribbean Contract Ch. 01-03

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Was Jessica there to work or to be pleasured?
8k words
4.71
23.6k
6

Part 1 of the 3 part series

Updated 10/20/2022
Created 01/15/2011
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30 Followers

Jessica stared out the window of the private jet as it flew over the island of St Lucia. She still could not imagine who had requested her and why all the secrecy. The only information that her boss had disclosed was that she would be working in St Lucia for two weeks with a new client developing a website for a new resort.

The plane touched down on the tiny airport runway. The view was spectacular, lush green tropics and white sand beaches with the most beautiful water Jessica had ever seen. The pilot emerged from the cockpit to open the door.

"Miss Sanders, I hope you enjoyed your flight. Marcus, your driver, is waiting for you at the bottom of the stairs. I will get your bags and load them into the car for you."

"Thank you, David, everything was wonderful!"

Jessica exited the plane to find herself standing next to a grey limousine. Marcus opened the door and she climbed in, as if she was accustomed to this kind of treatment. Truth was she had never dreamed that something like this would ever happen to her. Inside the limo was a bottle of champagne and chocolate covered strawberries.

Marcus leaned his head in the door, "JP is sorry that he could not meet you this evening. He is wrapping up some business, so he will be available tomorrow to show you around and explain why you are here." Marcus opened the champagne and poured her a glass, as he gave her a brief history of the island. "Miss Sanders, we have a half hour drive to the resort, if you are ready..."

"Marcus, please call me Jessica. What is the name of the resort?"

"Fantasy Falls, named for the thirteen waterfalls on the grounds."

Jessica sipped the champagne as she took in the beautiful landscape. Her mind tried to imagine the resort and the waterfalls. Her face flushed as she thought of the waterfalls. Jessica had a fantasy of experiencing a sexual encounter behind a waterfall. An image of a tall waterfall entered her mind; she closed her eyes and pictured herself there. She could almost feel his hands on her hips; feel his breath on the back of her neck as he whispered the ways he wanted to pleasure her. Jessica did not know the identity of the man in her dreams, she felt as if she knew him, but never saw his face.

Jessica's eyes flashed open as the front tire plunged into a hole in the narrow road. Champaign splashed out of her glass all over the front of her white satin blouse.

"Damn!" the expletive shot out of her mouth.

Marcus quickly rolled down the window that separated them. "Sorry, Miss Sanders, are you okay?"

" I am fine, Marcus, just putting on a one girl wet see-thru shirt contest back here," Jessica chuckled.

"I do apologize; I did not see the hole before it was too late. I will check the tire and get out your bags if you would like to change."

"The carry-on bag would be great, Marcus, this is kind of awkward."

Marcus stepped out of the car. One look at the tire told him, his boss was not going to be happy. He opened the trunk and retrieved the small navy blue carry-on bag. Marcus tapped on the window and Jessica rolled it down.

"Miss Sanders, Jessica, there seems to be major damage to the tire's rim. I will have to call someone from the resort to come get you and then wait for a tow for this car. I have your bag, so you can change out of your wet blouse, and again, I apologize."

Jessica changed into a pink v neck tee that she had packed in her bag; she figured it was the best thing in her bag to match the black skirt that she was wearing. Stepping out of the limo, she caught the last of Marcus' conversation. The call must not have gone well, by the look on his face.

"How far out are we, Marcus?"

"Only about ten minutes from the resort, "he sighed.

"Everything okay?"

"JP was pretty upset, and you might want to change out of that skirt"

"Why is that?"

"The remainder of the ride will be on the back of a moped," Marcus shrugged his shoulders. JP gave him strict instructions not to reveal any more information to her.

"Just great, I despise those things!"

"Sorry, JP told me to tell you that this is not how he planned your arrival and he will make it up to you."

"It's not your fault, Marcus, you have been very kind. I guess I will change into the shorts that I packed in my emergency bag too," she chuckled. She figured she still had it better than he did; at least she would be at the resort while he waited for a tow.

Dusk was approaching quickly. She could hear the hum of the moped as it approached. The driver was male, wearing tan shorts and a white shirt. He pulled up beside her, handed her a helmet and said, "Get on."

Jessica did as he instructed and could not help but let out a sigh of disgust at his rudeness. She certainly hoped this was not typical of most of the employees at the resort. As she settled behind the rude guy in the dark helmet, she was quick to notice his tanned and well toned legs. The moped jerked and her arms instinctively wrapped around his waist. He let out a small growl as her breast pressed tight against his back. He was not ready to see her again, he had a plan to win her over, and this was not in his plan. He would surprise her in the morning at breakfast and if she held a grudge over his absence for so many years, he could always play the "business card"; after all she was under contract to design his website.

As much as Jessica despised mopeds or motorcycles or other "two wheeled death mobiles", as she called them, the vibrations between her legs combined with the drivers masculine scent was having a nice affect on her. The road was rough causing the bike to bounce, which in turn, had her breast rubbing against his back. Sure, she could loosen her grip around his waist, but then her fear of falling off would ruin the moment. She closed her eyes and her senses were heightened. The lace on her bra lightly scratched against her nipples, causing them to stiffen, the drivers musky scent filled her nostrils and the vibrations of the bike added to both of those was causing her to become very aroused. She could feel her panties starting to get wet. 'First order of business...a nice long shower,' she thought.

"Damn!"

"What's wrong?" the driver asked as he slowed down at the resort's driveway.

"Nothing major, just my luggage," Jessica sighed.

"Your luggage should be outside your room within the hour."

The moped stopped and Jessica wasted no time getting off of it. The driver pulled away before she could even thank him. Shaking her head, Jessica walked inside the reception building. A beautiful, dark tanned young lady with an interesting Caribbean accent welcomed her. Tondra was the name on her nametag.

"Welcome to Fantasy Falls, are you Miss Sanders?"

"Yes, I am Jessica Sanders."

"Miss Sanders, we have been expecting you. How was your flight? Is Marcus bringing in your bags?"

"Thank you, my flight was wonderful, and I am not sure who is bringing my bags. There was a problem with the tire on the way here."

"Oh, my...Let me drive you to your cabana, you must want to get settled...well as settled as you can get until your bags arrive."

Tondra drove Jessica to her cabana on one of those large golf carts. The cabana was a larger one bedroom with a seating area and a large bathroom with a separate shower and garden tub. The rooms were decorated in a tropical theme with muted reds, yellows, oranges and shades of green. The large king sized bed had a canopy with billowing white net on all sides. Jessica paused for a moment just taking it all in. On a small table in the sitting area, there was a huge vase of fresh tropical flowers and a note...

Miss Sanders, I hope the room is to your liking. I have also set up a small office for you in the Conference Building. I apologize that I could not arrange to join you for dinner and to welcome you this evening. Room Service will bring your Dinner at 8:30 this evening. I have scheduled the day off tomorrow to show you around the resort, and nearby shopping areas. I will have Marcus pick you up at 7:00 in the morning for breakfast.

Please call Tondra at the front desk if you need anything this evening.

Enjoy your evening and I will see you tomorrow. Wear comfortable clothing and walking shoes.

JP

Jessica looked at her watch. She had about half an hour before her bags arrived and almost two hours until dinner. A bath seemed a perfect way to spend her time. She walked into the bathroom and noticed a small basket of assorted bath gels, powders, soaps and one very odd bottle in the assortment.

"Baby oil," she laughed. "I have not taken a bath with baby oil in so long!"

Jessica thought back to college, she loved to soak in a hot bath with baby oil. Her skin would be so slippery; she loved the feeling of gliding her hands across her slick skin. Not to mention the wonderful lubricant it served as, for a good self satisfaction session. "Mid-term stress relief" she called it.

Just thinking back was making her hot. 'Why not,' she thought. Reaching over she turned the hot water on full blast and poured about three tablespoons of oil into the water. While her bath was filling, she went to the refrigerator in her small kitchen area. There all chilled and waiting was a bottle of wine. She poured herself a glass and proceeded back to the bathroom. The water was a perfect temperature and height in the tub. Jessica pulled her hair up into a clip; she thankfully had in her purse, stripped off her tee and bra, then eased down her shorts and panties. Carefully, she stepped into the tub and eased her body into the warm oily water.

"Mmmm," Jessica moaned as she rubbed the oil across her breast.

Jessica sipped her glass of wine as she let one hand explore her own body. Funny how something different in your bath can make such a difference in how your body feels. She glided her hand over her legs, her abdomen and her chest. She playfully pinched at her nipples, the oil making them too slick to get a grip, but how good it felt. She took turns working each nipple into a fully erect, tingling nub. Her glass was soon empty, so it freed up both hands. Jessica slid one hand down between her legs and rubbed her fingers through the small patch of hair just above her clit.

"Oh, yes," she whispered.

Her middle finger slid across her clit. She closed her eyes and imagined the strong hands of "rude moped guy". He may have been rude, but he just oozed sex appeal. She imagined his strong hands rubbing her clit and sliding between her swollen lips, back and forth slowly before exploring the depths of her canal. Her hands were performing the actions that she was imagining him doing. One middle finger was rubbing her clit while first one finger of the other hand slid in and out, then two fingers were fucking her slick pussy.

Breathlessly Jessica stated, "I wish my damn vibrator wasn't in my suitcase about now"

Pumping her fingers faster, Jessica started to feel her muscles tighten around her fingers. Her clit started to tingle, the muscles started to spasm, and her fingers were drenched in cum.

"Oh Yeah! Oh fuck yeah, yes, yes, yes!" Jessica cried out through clenched teeth, as her orgasm rocked her body. Her hips were bucking and her ass was sliding on the bathtub bottom.

Her orgasm subsided just in time for Jessica to catch herself before she slid down into the oil filled water. She took a deep breath and slowly exhaled.

"Wow, I can't believe I forgot about the baby oil baths," she laughed.

Glancing over at the clock told her playtime was over and dinner would arrive soon. She drained the water and put on the fluffy white robe that hung from the back of the door. A quick peek out the front window showed her bags had arrived safely. Jessica began to unpack her things for her two week stay. She really hoped this would not be all work and no play. Her work would begin on Monday morning, but already her Saturday was arranged for her, surely she would have some free time tomorrow and Sunday. Just as she finished unpacking, a soft knock at the door announced her dinner had arrived. She opened the door and a young man stepped inside, put the tray on her table and promptly excused himself. Jessica was surprised and relieved to see Chicken Alfredo, steamed broccoli and garlic bread. One of her concerns was the food, she was not one for exotic food and she did not eat a lot of fish. Her research showed St. Lucia was known for both, but she had to admit, she was curious to try the "Banana Catsup" she read about.

After dinner, Jessica figured it was in her best interest to get a good night's sleep. She brushed out her hair, brushed her teeth and slipped into a short cotton gown. The bed, with the netting all around it gave her a very safe feeling. She was not concerned about insects, which was the netting's original use in the islands. In modern times, the fabric was simply for decorative purposes. The sheets were made from high quality cotton that felt like silk against her skin. With her alarm set for 6:00 am, she settled into bed. Jessica was quickly lulled to sleep by the sounds of a small waterfall somewhere just outside her cabana.

Jessica writhed between the sheets. She was deep into one of her explicit, erotic dreams. Her faceless lover had disappeared behind a massive waterfall. Jessica frantically searched for a path to follow him. She could hear him call to her, "Come to me Jess, come to me." The water parted and she stepped inside a secret cave. The only light was a flicker from a candle down a long, narrow shaft. "Come to me," the voice said again. Jessica walked down the long narrow path; suddenly the candle went out, causing her to freeze in place. Her body went rigid as she felt his hands upon her hips. She wanted to scream, but no sound came out. The only sound was the water from the fall crashing on the rocks. His hands slowly moved up her rib cage stopping just below her breast.

The sound of rushing water faded as his voice whispered in her ear, "Relax Jess, this is your dream, you have the power to awake at any time you choose. I can not, nor do I desire to hurt you. I am here to pleasure you and give you the opportunity to play out your fantasy."

His smooth voice made her tension slowly fade. He felt her slowly relax, her muscles eased beneath his hands, her breathing became less labored. His fingers gently moved across the undersides of her breast, working their way to her areolas. With an ever so light touch, his fingertips circled her nipples. Her little nubs were reacting to his touch, becoming quite rigid. Slowly they started to point straight out from her tits, allowing him to softly roll them between his thumbs and index fingers.

Jessica let out a small moan, "Mmmmm"

His hands slid back to her waist, turning her to face him. He could see her clearly in the darkness, her body a vision of perfection. He lowered his mouth to her breast, and very gently kissed each tight bud.

"Jess, I am going to move you over to a special table, just remember, I can only bring you pleasure."

Her body was lifted and placed on a very soft table. The unknown surface felt warm against her backside. She let her mind and body become enveloped in the warmth. He lifted her arms above her head and into two loose straps. Her legs slowly spread open as he guided her ankles into similar straps. Jessica had never experienced any form of bondage in reality, so her dream took a gentle approach.

A tiny squeak broke the silence, as a portion of the table between her legs was lowered. A chill of excitement ran up Jessica's spine.

"Let your mind go sweet Jess, you are the one guiding me."

His velvet smooth voice flowed through her brain. Jessica relaxed and guided his lips to her breast. The heat of his mouth exceeded the warmth below her body. His tongue flicked at her stiff nubs, the tightness causing a tingling sensation. Gently his teeth started nipping at each taut bud. Jessica started to feel the warmth moving to settle in between her legs. His mouth opened wider to suck in her entire areola and nipple, increasing suction, each time he would alternate between each tit. His hands pushed her tits closer together as his pace increased.

Her chest heaved as her breathing became more rapid. His mouth and hands left her breast and traced a path to her lower abdomen. His hair tickled across her skin as he lowered his head between her legs. She could feel his warm breath as he paused inches away from her awaiting pussy.

"I want to turn over," Jessica whispered, "I want you to lick me from behind"

His soft laugh filled the room, "Dear Jess, you are already turned over."

It was true; Jessica was now on her knees with her chest and head resting on the table. A tiny vibrator was positioned atop her clit humming softly. His hands gently spread open her backside. A tiny drip of liquid dropped onto her crack and tickled along her slit, followed by another, then several others. The cool liquid made her shiver. A clicking noise broke the steady hum of the vibrator, as the hum got louder and the vibration more intense.

His mouth watered as he waited, until she willed his mouth in closer. His tongue started just under her clit and ever so slowly worked its way through her moist slit, stopping just outside of the entrance of her very core. This maneuver was repeated several times before he flattened his tongue and began to lick her outer lips with long strokes. Every third or fourth stroke, the tip of his tongue would dive into her canal. Her hips swayed slightly and her pussy was emitting a sweet aroma that filled his nostrils. His taste buds loved the sweet and slightly tangy flavor of her secretions. The flavors swirled across his tongue like a fine wine. He let out a guttural sound of approval that echoed in her head.

His sounds heightened her arousal. The tip of his finger was pressing against her tight hole, waiting patiently for her to relax and grant him access. Her inner wall muscles relaxed and his finger easily slid up into her.

"Oh, yes," Jessica whispered, as she tightened around his finger.

His finger glided in and out rubbing against her smooth, velvety walls. Her juices soaked his finger and allowed another to slip in beside it. Her clit was tingling with vibrations as her pussy was being filled by his thick fingers.

"Faster and harder," she moaned.

His palm pressed firm and rubbed back and forth as his fingers plunged deeper inside her, her body writhing with pleasure. Her knees started shaking as his fingers sped up, his palm rapidly slapping her wet lips.

"Oh, Yessssssss," she screamed. The echo resounded through the cave.

As her orgasm rocked through her body, his thick penis slipped up into her, causing her orgasm to prolong. Somehow she was now sitting on his lap, his cock buried deep in her pussy. Her ass was grinding against his legs as he sat upon a flat rock. The head of his thick cock was rubbing a spot that she had never felt before. This level of pleasure was unknown to her. She seemed to stop breathing, she heard no sound, and all she could do was feel... feel the orgasm, that only could exist in a dream.

Chapter 2

Jessica's eyes fluttered open, as she slowly emerged from her dream state. Her lightweight cotton gown was tangled around her waist from thrashing between the sheets. As she unclenched her thighs, a pool of liquid flowed from deep inside her, and tickled her ass as it flowed down her crack onto the sheets. Her eyes shot open as she realized what was happening. She had similar dreams often, but never before had she experienced an actual orgasm as she awoke.

"Who are you?" Jessica said aloud to the faceless man in her dreams.

Jessica lay in bed for a few minutes trying to replay her dream, large portions of it already disappeared. What had not disappeared was the wetness between her legs and the aroma that now filled the air around her. A quick glance at the clock told her she had just enough time for a shower before Marcus would arrive to take her to meet her newest client, her boss for the next two weeks.

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30 Followers