Jackie of the Caribbean By TrackJim


Jackie of the Caribbean By TrackJim

Part One

Jackie was thrilled as she read the letter from Nuclear Cosmetics. She had entered a jingle contest for their line of sunscreens and had won a fully paid trip to the Caribbean for two. Not being involved with anyone at the moment she decided to see if her cousin Jenny would be interested in joining her. It would be a nice break from the winter's cold.

As Jackie prepared to call Jenny, she hesitated. The events of Thanksgiving which left them both naked on a parade float briefly rekindled Jackie's memory of other embarrassing situations. After she and Jenny had finally been rescued, they had sought refuge in Jenny's home. Jenny had told her of some of her unplanned naked experiences. Jackie was ashamed to find she was aroused by Jenny's situation. Jackie hadn't wished the experiences on Jenny happen, but Jackie's own loss of control and humiliation left her stimulated. Maybe Jackie could help Jenny and determine if Jackie's own feelings were unique.

Jenny responded to Jackie's offer enthusiastically. She told Jenny she would have many opportunities to get a good tan. Jenny said she wore only one-piece suits as they tended to be safer. Jackie said not to worry. Nuclear Cosmetics promised to provide bikinis, sunscreen, and other leisurewear. Part of the trip's deal with Nuclear Cosmetics required a photographer to shoot photos on one of the days as part of their 'Winner's Coverage' for use in future contests. They agreed on the second week of February as the perfect time.


The next two weeks flew by with dreams of palm trees, ocean breezes, and sandy white beaches.


Jackie and Jenny flew into Miami International Airport on different flights within minutes of each other. Jackie rushed to the gate in time to greet Jenny. The likeness between the two was great. Jackie looked to be Jenny's younger sister. Jackie was a bit longer-waisted with slightly shorter legs and reddish-brown hair, but they could have been sisters. They were both dressed for the colder climates they'd come from and wanted to change into polo shirts and shorts more appropriate to the warm Miami and warmer Caribbean. Their suitcases were already being forwarded onto the flight to St. Justin Island, but they had both carried a change of clothes in their carry-on bags. Jenny had a momentary chill as she remembered her last visit to the airport, but they proceeded to the ladies' room and changed. They left the women's wearing almost identical white tops and shorts that did little to hide their curves and endowments.

Forty-five minutes they boarded their connecting flight to St. Justin. They arrived on time and were whisked to their hotel by a limo provided by Nuclear Cosmetics. They were joined by a representative from Nuclear Cosmetics and led to their fourth-floor room. From the open balcony doors, they saw a beautiful beach with crashing waves from a deep blue sea. The NC representative spoke.

"My name is Amanda. We have an agenda set up for you. Today is yours to get used to the surroundings. Tomorrow the photographer will meet you on the beach at 9 AM for your photoshoot. Bring all the bikinis in this bag, they are your wardrobes for the shoot. There is also sunscreen in the bag. For the next two days, we have arranged for a charter sailboat to cruise around the islands under your direction. The remaining three days are completely open for anything you want to do. I'll be here at 8:30 AM to take you to the beach. Here is my card with my cell phone number. If you have any problems, call me any time. I hope you enjoy your stay."

Jackie and Jenny had no questions so Amanda left. They opened the bag of bikinis. There were twenty-five different bikinis in the bag and several bottles of NC sunscreen and lotion. Jenny's modesty made her ask if she could change in the bathroom. Jackie said okay and that she would also change into one. Jackie picked a bright blue wet-look number that exposed most of her cheeks and snuggly covered most of her firm breasts. The material stretched over her breasts into an attractive 'shelf'. Jackie was looking at her image in a full-length mirror when Jenny stepped from the bathroom. Jenny wore a tiny top that covered little more than her *******. The bottom was cut more like a g-string that crawled up her crack, leaving her ass very exposed. Jenny's stood next to Jackie and blushed a deep red as she saw her own reflection.

"I can't wear this in public," exclaimed Jenny. "I feel naked."

"You look fantastic, Jenny. If you're uncomfortable we can trade suits. You obviously don't need the support of this stretchy top, but it'll give you more coverage. Let's see what the other suits are like."

Jenny returned to the bathroom and they both changed again. Each suit was **** and revealed a lot of feminine flesh. Jackie chuckled and said that was the object of bikinis, but Jenny was still modest. Jenny ended up choosing the wet-look blue suit Jackie had first tried on. Jackie picked the tiniest of the bikinis in hot pink with side ties on the bottom. They wrapped themselves in large towels, grabbed sunscreen and their bags, and left for the beach.

The beach had only a few sunbathers and swimmers. They walked down the beach to a secluded section. Finding themselves out of sight of the others, they spread their towels, applied sunscreen, and lay on their towels. Jackie rolled onto her stomach and pulled her top over her head.

"Jackie, do you think that is wise?"

"Jenny, we are on vacation. You've got to learn to relax. Besides, I did not say you had to remove your top. I want to start a nice tan without any strap marks on my back."

Fifteen minutes passed and no one came by. Jackie rolled onto her back.

"JACKIE! Don't you feel you have to put your top back on? You are *******."

"I'm just so relaxed. Why bother?"

Jackie felt the hot sun on her breasts and sighed. She loosened the string ties on the side of her bottom and moved them so that her crotch was covered, but her thighs and waist were fully exposed to the sun. She became drowsy and drifted into a light sleep. Jenny watched Jackie and wondered. She thought Jackie was almost as modest as herself and dreaded being caught naked in public. Jackie must trust Jenny enough to protect her. Jenny rolled over on her stomach. Within minutes Jenny had drifted into a deep sleep.

Jackie woke with a start as a wet tongue washed her right cheek. She sat up and found a beautiful golden retriever panting in front of her. Jackie held her arms over her chest and looked around her. It was just her, Jackie, and the dog.

"If there is a dog, there must be an owner and he might be coming along soon." Jackie reached over to grab her top. The dog, thinking this was an object of play, scooped the top-up in his mouth and backed up a few steps.

"Here, girl. Please come here." pleaded Jackie. The dog maintained its distance. Jackie stood and grabbed her towel. Her bikini bottom dropped between her legs, forgotten. "If I throw the towel, maybe the dog will drop my top and go after it" thought Jackie. She balled the towel and threw it to the right of the dog. The dog trotted over to the towel and scooped it up without dropping Jackie's top. Jackie, now thoroughly frustrated, took off after the dog. The dog galloped about fifty feet before Jackie realized she wasn't going to catch it, it was just too fast. It slowed to a trot and disappeared around a rocky outcropping away from the hotel.

Jackie, now realizing she was **** ran back to where she had laid. As she approached her spot the dog zoomed past like a rocket. The dog scooped up Jackie's bikini bottom before disappearing the way she had come. Jackie sat next to the sleeping Jenny with her bare bottom on the hot sand. Jackie started crying and Jenny stirred. Jenny looked over at Jackie. Jenny's squinted sleepily at Jackie and then her eyes opened wide.

"Jackie, what happened?!?"

Jackie explained about the dog. Jenny now knew what it had been like when others heard her own stories. Jenny would have laughed if not for the expression on Jackie's face.

"Here dear, let's wrap my towel around you and we'll head back now. The towel is large enough to cover you." Jackie stood as Jenny passed the towel to her. Jackie quickly wrapped it around her naked body. It was fairly large and covered her like a sarong. She should be able to get back safely.

Jackie and Jenny needed to cross the crowded pool area to get back to the elevators that led to their room. As they approached the pool area the golden retriever reappeared and closed his mouth on the bottom edge of the towel. Jackie clinched her left hand at the towel where it was knotted between her ample breasts. Her right hand attempted to hold the towel together at her crotch. Jenny grabbed the towel near the dog's mouth and pulled against the dog. Jackie was screeching in horror as she felt she was about to be stripped naked. Jenny was groaning as she pulled with all her might against the dog. The dog dropped the end of the towel and lunged at Jenny. The nails on the dog's right paw caught on the material between Jenny's heaving breasts.


Jenny's torn top fell open and the dog dropped back to all fours. His jaws closed again on Jackie's towel. Jackie was pulled off balance and forward into Jenny who had her arms around her chest. Jackie lost her grip and fell back toward the pool. By reflex, she reached toward Jenny for support as the dog raced away with the towel. Jackie's right hand caught the back of Jenny's bikini bottom. As Jackie fell into the pool Jenny's legs were pulled out from under her and the bikini bottom was pulled down and off her legs.


Jackie fell into the water in a three-quarter belly flop which stun her naked breasts and knocked the breath from her. She came up sputtering in time to see Jenny's naked bottom bouncing as she jumped into the elevator. The elevator doors closed. Jackie was left pressing her breasts against the side of the pool. There were shouts, laughter, and even applause as Jackie's face and shoulders turned beet red. Moments later, when she got her breath, she pulled herself out of the water, to more applause, and ran for the elevator. Her hair clung flat to her head. As Jackie ran the water shook from her luscious curves. She stood dripping water at the door for what seemed like forever until the elevator returned.

The elevator rose to the fourth floor with no stops. As the door opened the naked Jenny greeted her with a frown.

"I dropped our room key at the pool when the dog attacked. We have to go back down to get it" Jenny exclaimed. The blush on both women had extended down over their breasts as Jackie ran through the pool area and retrieved their key while Jenny held the elevator.

As the two finally fell on their beds, neither could believe what had happened in their first two hours here. And there were seven days left.


Back on the beach, a man walked, calling for his dog. "Ashley, where are you girl? The dog appeared around an outcropping and trotted to her owner. "What have we here?" The dog dropped a bikini top and bottom from his mouth. "What have you been up to?" he exclaimed as he held up the bikini, smiling at his own imagination. "Up to your old tricks again? Ever since I got you from that old stripper, you can't seem to break the habit of getting into the act?" He chuckled as he petted the panting dog. "Maybe I should follow you on your romps. Come along now girl".




Jackie and Jenny in the Caribbean - Part Two



With some concern, Jackie and Jenny met Amanda the next morning for the photoshoot. As the day wore on and no mishaps occurred Jackie and Jenny grew more comfortable. Amanda and the photographer were patient and courteous. A cabana had been provided for Jackie and Jenny to change in and they were joined by Amanda who also changed into some **** bikinis. The bikini, sun wraps, and short robes revealed all three women's **** bodies, but there was no hint of being ******* or bottomless. Amanda also reminded them to keep applying the sunscreen "You don't want to burn that healthy skin of yours."

The photographer was very professional. He complimented Jackie and Jenny on their figures and helped them with their poses. At the end of the session, he gave them his card and said that he could use them as paid models on future shoots. Jenny modestly declined but Jackie said she might take him up on it as long as there were no ******* or **** requirements. They were told they could keep the assortment of bikinis for themselves. Amanda gave them each a bag of leisurewear: an assortment of shorts, slacks, and tops. The photographer and Amanda said bye and wished them a pleasant vacation. Jackie and Jenny returned to their room and changed into light slacks and polo shirts.

The two women spent the rest of the day wandering the nearby villages and seeing the island sights.

The next day Jackie and Jenny went down to the peer where the chartered boat was waiting for them. Following the written instructions from Amanda, they found the 28-foot sailboat, "The Wet Dream". Jackie and Jenny chuckled at the name. They were delighted when the charter captain turned out to be a petite, attractive woman of about forty. Her small breasts did nothing to detract from her long dark hair and complexion. The captain introduced herself as Ellen and immediately set the women at ease. Ellen said she had been captaining the boat for six years after she bought it from the former owner. Ellen was licensed and "hadn't lost a passenger, yet". She suggested a course taking them past some uninhabited islands that day. They would drop anchor that evening in a small cove that was very private. The next day they would visit a quaint little island that had not gone commercial where visitors were still greeted in a truly friendly manner. Jackie and Jenny said the agenda sounded wonderful. Ellen said she would occasionally need some help with the sailing, but that she would usually be able to handle the boat by herself.

Using the motor they left the harbor. Once out of the harbor Ellen hoisted the mainsail and they slid along the quiet seas so the sound of the waves and seagulls. Ellen had Jackie take the wheel for a few minutes on the open sea while she went below. Ellen reappeared a few minutes later wearing just a white bikini *****. Her small firm breasts showed no signs of any tan lines and none were visible around her *****.

"Is that your usual naval attire," asked Jackie.

"No, but with just you two aboard, it'll do. I like the feel of the sun and the wind on my body. I'll put something more on if we are approached by another boat." Ellen took the wheel. "Why don't you two join me."

Jackie smiled and went below. Jenny blushed deeply red when Jackie reappeared wearing their tiniest g-string bikini *****. Jackie stood next to Ellen and they talked as Jenny stood silently to the side.

"Jen" asked Jackie "why don't you join us. The sun feels wonderful."

Jenny answered, "No, I just couldn't". Jenny's blush deepened as she went to the foredeck and laid down on a towel. The sun did feel wonderful and there was no one around. After a few minutes, Jackie dropped next to Jenny on another towel.

"Jackie, how can you just lie there exposed like that?"

"Jen, it is such a wonderful day and it is just us girls. What could happen?" Jackie rubbed sunscreen on her breasts and worked it over her body. "Could you help me with my back?"

Jenny took the sunscreen as Jackie turned over. Jackie's hands worked the sunscreen into Jackie's back. With Jackie's back now covered, Jenny worked her way up Jackie's legs. As she got to Jackie's upper thighs Jackie said, "Wait a minute." Jackie stood, removed her bikini bottom, and lay back on her stomach. Jenny hesitantly finished Jackie's upper thighs and started on Jackie's back. Jenny realized how good this must feel to Jackie as Jackie uttered several relaxing moans. After finishing with Jackie Jenny decided to re-apply her own sunscreen.

Jenny sat on the foredeck and worked the sunscreen down her own shoulders to the tops of her breasts. After pausing a few moments Jenny untied her top and worked the sunscreen into her pale breasts. Her ******* were very erect and moaned as she rubbed extra lotion over them. She looked around and saw no other boats or land anywhere close. She pulled her bottom down her legs and passed her hands over her lips. She moistened, responding to her own touch. She became very aroused, but she was not going to ********** in front of Jackie and the world. She lay back on her towel and felt the sun on her outstretched body. Within moments she was asleep.

Ellen came forward to check on her two passengers. She smiled at the two sleeping nudes. Ellen scooped up their few pieces of clothing and took them to her own cabin.

She locked the door to the cabin area and returned to the wheel. Ellen steered to the uninhabited island where she had planned to stay the night. Forty-five minutes later as Ellen was easing the boat into a cove on the island, Ellen heard a scream from the foredeck.

"Where's my bikini?" It was Jackie's voice. There was the sound of bare feet running down the port side of the boat. "Ow. Help!" Jenny, after stubbing her toe, had lost her balance and fallen over the low railing.


There was a giggle and Jackie shouted "Nude overboard". Jackie walked more carefully along the port side and dropped a life jacket down to Jenny who was treading water. The boat was at a standstill. Ellen dropped the anchor from the starboard side and walked over to stand above Jenny. Jackie, wrapped in a towel, was giggling as Jenny pulled the life jacket over her head and loosely tied the front of the jacket over her chest.

"You find that funny?" asked Ellen.

"Yes, Jenny is so modest even when there is no one but us to see her" answered Jackie.

"Well, in that case..." Ellen pushed Jackie over the side, grabbing the towel and holding it. Jackie was taken totally by surprise and fell naked into the clear water. Ellen laughed and said "You two head for the beach. I'll join you with the dinner picnic basket." Jackie was laughing too and set out for the beach. Jenny was a bit mad and followed after a few moments.

As Jackie walked out of the water, she found herself stimulated by the fact that she was **** on an island. Her clothes were back on the boat. Jackie sat on a log and felt one with nature. She was reminded of some of her old college exploits as she stared at the clear sky. She unconsciously held her left arm in front of their breasts and closed her legs. Jenny walked out of the water with her left arm over her breasts and her right hand over her *****. Jenny's blush was very obvious.

"Come on, Jen. There's no one to be embarrassed in front of. It's just Ellen and me."

Jenny was clearly not relaxing as they saw Ellen had inflated a raft. With the picnic basket in the raft, Ellen swam behind the raft pushing it to shore. Ellen emerged from the water still wearing only her bikini bottom. After beaching the raft Ellen walked up the sand with the basket and spoke.

"I see at least one of you is still not comfortable in her birthday suit. Here."

Ellen reached into the basket, pulled out two long t-shirts, and passed them to Jackie and Jenny. Jenny thanked Ellen and quickly put on her T-shirt. Jackie pulled on her T-shirt and found it reached a foot over her knees. Jenny visibly relaxed in her own T-shirt. The three women eat and chatted. Jenny was drawn into the conversation.

As they finished eating Ellen asked, "I see from your tan lines that you must not get much opportunity to do any **** sunbathing? Why don't you two relax as I clean up and get the basket back on the boat? Give me your T-shirts."

Jackie giggled and pulled hers over her head. Jenny did not move.

"Come on Jenny. It's just us. You've got to relax," said Jackie.

Jenny stood and reluctantly removed her T-shirt. Ellen placed the t-shirts in her basket and headed for the raft and said "I'll be ready to set sail in about thirty minutes. I'll sound the boat's horn and you can swim out." Jackie and Jenny settled down on their towels under the bright tropical sun.


On the other side of the island three rubber rafts filled with the local militia were practicing their landing and raiding techniques. The drug traffickers were using these small islands to exchange money and goods. The militia needed to practice so they could surprise the traffickers. They worked in silence as their electric motored rafts approached the beach. The sixteen men quietly stormed the beach. They were to work their way across the island to the cove and hide in a practice ambush. They had been warned special agents disguised as tourists would be their targets. They were to take them into custody as if they were the real thing. No bullets were to be fired, but all standard procedures were to be used.

Approaching the cove the men took up their positions behind the foliage near the edge of the beach. The lieutenant commanding the men edged forward to take in the situation. A "charter boat" was anchored in the harbor. A figure was visible moving on the boat.

"Duckling to Mother Goose. A sea approach must be timed to take the boat. Plan your approach for thirty minutes from now. Mark!"

"Confirmed Duckling. Mother Goose out."

Using the binoculars the lieutenant slowly scanned the beach. He froze as he saw two nubile bodies laying stomachs down on blankets. "What a disguise! This was planned well by headquarters. Men, move forward but do not expose yourselves to view. We will be storming out in twenty-eight minutes. Prepare yourselves. Remember no ammunition in your guns. This is just a simulation."

The other men moved up to take in the view. And what a view it was. One of the women turned over. Her **** body was delicious. The second woman turned over and sat up. Some of the men were uncomfortable with the exposed female flesh. Suddenly a horn sounded from the boat.

The lieutenant, thinking they had been seen, ordered "Charge now, now, now!" Sixteen camouflaged figures burst from the foliage as the two women stood up. Jackie and Jenny turned as they heard the lieutenant shout. Jenny muttered "Oh no, oh no" as they were surrounded.

"Stand still with your hands behind your backs" ordered the lieutenant.

Jackie and Jenny were terrified. Were these men terrorists or what? As Jackie tried to ask what was going on, cuffs were snapped on their wrists and gags placed in their mouths. The lieutenant shouted to the boat "Stay where you are." Without boats and no ammunition of their own, the men were unable to do much as they saw the anchor hoisted and heard the motor start. Jenny and Jackie watched as Ellen took the boat (and their clothes) out of the cove.

"Lieutenant," said one of the men "our seaborn assistance is still twenty minutes away."

"We'll just have to be satisfied with what we got." The lieutenant turned to see his men staring at the two naked "traffickers". "You get busy. Search the area and confiscate all belongings."

"Sir, there are only these two towels. There is nothing else of any significance around here. Should we do a search of the prisoners?" A smile crept onto the face of the militiaman.

"Well, the strip is needless. We will let headquarter perform any invasive procedures. We'll take them back with us." Grabbing the radio he continued. "Mother Goose, this is a duckling. Seaborn assistance is now pointless. Return for debriefing."

"Acknowledged, Duckling. Mother Goose out."

Jenny and Jackie had to trudge back to the militia boats, gagged and handcuffed. Their blushes reached down to their toes as the men helped them walk. The occasional "assistance" is often handed to the breasts and asses. Jenny was totally humiliated by the situation. While wearing cuffs there was absolutely nothing she could do to cover herself or even protect herself from the frequent touch of the men. Jackie was embarrassed too but found herself surrendering to the situation and getting a thrill from it. She shamefully admitted to herself that she was aroused. Only the sweat pouring down her torso and onto her legs hid the fact that she was secreting between her legs.

Once at the boats they were helped in, still ****. The boats met a small cutter. The women were escorted on board and placed in a windowless room by themselves. After about twenty minutes they heard and felt the cutter dock. They were escorted back to the foredeck. The cutter was docked on a pier in the middle of the harbor. Civilian craft and people stared from the dock and boats as the two bound **** women were forced to stand on the bow of the cutter. The lieutenant stood between these prisoners. Suddenly the radio on his belt chirped.

"Lieutenant Largos, here." There was a pause as he listened to a voice. "What do you mean where are we? We conducted the raid and have prisoners right here" shouted Lieutenant Largos." A few more moments passed as Largoes listened. He was clearly upset and a blush formed on his face. He clipped the radio back on his belt and ordered "Get these women below to the captain's cabin right now." Several eager men helped Jackie and Jenny to a much larger cabin with portholes. A few minutes later Largos entered the room.

Largos spoke. "I'm sorry ladies. There has been some error in our orders." The gags and cuffs were removed. As Jackie and Jenny tried to cover themselves Largoes continued. "We were ordered to exercise on the wrong island and took you to be agents acting as drug traffickers. We are getting clothes for you now. You'll be escorted back to your hotel with our sincerest apologies." There was a knock on the door and clothes were handed into Largos. The women quickly donned the pullover tunics that covered them to their thighs. "We are very sorry for our mistake. If there's anything we can do, just ask."

Jackie, still blushing, smiled and said, "Well, you could leave us the cuffs and keys."

"Jackie" exclaimed Jenny. "What do you want them for?"

"Jenny, I was remembering my college days. Did I ever tell you about our Halloween ritual?


Jackie and Jenny in the Caribbean - Part Three

After a good night's sleep and Jackie were ready for another day. Jackie did have to do a little convincing Jenny that they should not just stay around the hotel where it was safe. A call to the marina and Jackie spoke to Ellen who assured them she was still available for their charter. Ellen said that the militia had contacted her and insisted they cover the charter cost (plus a generous amount to keep quiet) since the militia had made the mistake. Ellen said she would give them part of the generous money that the militia had given her and their charter was still free to Jackie and Jenny. Jackie said they would meet Ellen at her boat and discuss their options.

Jackie prodded Jenny until Jenny finally agreed to meet with Ellen. Jackie stuffed a bag with some clothes and swimwear while Jenny got dressed. Jackie had put on a halter-top and Bermuda shorts when Jenny emerged from the bathroom. Jackie looked at Jenny's attired and shook her head. Jenny was covered from neck to ankle in a jumpsuit. Jackie did not try to talk Jenny into cooler attire, but grabbed Jenny's arm, and off they went to the marina.

Ellen greeted them with a smile and hugged Jackie and Jenny. "You dears had such a bad day yesterday. If you are game, I'd like the three of us to do something together. If you want I can get a friend of mine to take us para-sailing."

"Para-sailing... What's that?" asked Jackie.

Ellen answered. "You wear something like a parachute. We have you standing on the back of a motorboat. You wear a harness attached to a wench on the boat. As the boat speeds up the para-sail lifts you into the air. It's like skiing on air. You can easily get 200 feet up when the boat is going fast. I've done it and it's a lot of fun.... quite relaxing. It doesn't require any effort as you hang in the air like a kite."

Jenny remembered her last experience with a kite and became quiet, but Jackie spoke right up. "That sounds like fun. Let's do it." Jackie grabbed Jenny's hand and the three walked farther down the pier.

Ellen went first so Jackie and Jenny could see how safe it was. Ellen changed into a bikini. Once Ellen was up it was obvious that Ellen was enjoying herself. Jackie saw Ellen's smile through the binoculars she used. After about thirty minutes Ellen hit the release and the cable harness slipped from Ellen's body. She used the directional pulls on the para-sail to drift back toward the boat. As she floated down to the water the cable was wrenched in. The boat circled back and picked up Ellen.

Jackie was eager to go next. She pulled off her halter-top and Bermuda shorts revealing a skimpy string bikini with side ties that caused Jenny's face to blush mildly. Jack, the owner of the boat, spent extra time to make sure the harness was properly on Jackie's body. No one noticed when he tied the side ties into the cable harness. Jack declared Jackie ready and off they went. Jackie felt wonderful as she glided a hundred feet above the water. The warm breeze caressed her flesh and seemed to hold her in an airy embrace. The boat was making a slow 180-degree turn when Jackie checked her watch. She had been para-sailing for over forty-five minutes. She hit the release and felt the harness jerk free from her body. She noticed that the wind was now brushing across her *******. She looked down.

"Oh my God, where is my bikini." Jackie wanted to reach down and cover herself but she was afraid to let go of the directional pulls used to steer. If she let go she thought she would drift right down onto the beach. She pulled the ties and performed a slow 180-degree turn away from the beach. She seemed to just hang **** in the air with her arms above her head. An updraft caught her and lifted her another fifty feet into the air.

In the boat, Jenny was shocked and embarrassed as the naked Jackie seem suspended in full view. "We have to get her down."

Ellen slapped Jack on the arm and gave him a dirty look, but the corners of Ellen's mouth turned up. "I'll have to double-check my own harness when I go up again" whispered Ellen in Jack's ear.

Jack said "If she would just let go of the directional pulls she would drift right down, but she has turned away from the beach. With the hot off-shore breeze and the thermals from the beach, she could stay up there until evening." Jack was keeping the boat almost under Jackie so as to help her when she eventually hit the water. Besides, it made for a better view.

Jackie felt like a naked yo-yo. She would drift down to about fifty feet and then be lifted by an updraft to almost 200 feet. She looked over her shoulder and saw a crowd was gathering on the beach. She could hear cheers each time she was lifted up. By now Jackie was holding her legs together in an attempt to preserve a bit of modesty, but her **** was aimed straight at the beach. As she looked out to sea Jackie noticed a few boats had gathered and were also witnessing her plight. "At least there are fewer people out there than on the beach," thought Jackie. She looked at Jack's boat below and was appalled as she saw Jenny trying to hide a smile. Jackie's breasts quivered as she tried not to cry.

It took over an hour for Jackie to drift down to the water. The motorboat pulled alongside and Jackie climbed in. Jackie wanted to rush to put on her shorts and halter-top, but Jack said he needed a moment to remove the para-sail harness. Jackie stood trying to cover herself as he released the straps around her waist, shoulders, and thighs. Once free Jackie quickly pulled on her halter-top and shorts. She did not say a word but just sat at the back of the boat blushing beautifully.

"Well, Jackie, you were right. It was better to get out today," Jenny said with a smirk.

Under her breath, Jackie muttered, "Just wait for tomorrow."



Jackie and Jenny in the Caribbean - Part Four

Jackie and Jenny returned to the hotel after Jackie's rescue from the para-sailing. Jenny was in a good mode, but Jackie was quiet.

"Jackie, I'm sorry I laughed at you. I know how humiliating that must have been. It's just after all the times I've been the victim, I guess it was relief that it wasn't happening to me that made me see the humor in the situation."

"Humor?" fumed Jackie. "I've just don't see it."

"Look, I'll make it up to you. Tomorrow we'll do whatever you want. I'll really try to relax."

Jackie seemed to cool off. "Okay, cuz. There's a party Ellen told me about. It's very festive with colorful costumes. I wasn't going to bring it up, because it sounded rather wild, but it is an island custom. If I can pick out the costumes, we'll have a good time."

"Okay. I'll really try to have fun, Jackie."


Ellen had told Jackie about the party and it had interested her. It was a little like the old college days. And who was to know? They were down here by themselves. If things got a little carried away, so what? Jackie made Jenny stay while she went to arrange for the costumes.


"Come on, Jenny. Pass out those clothes and I'll pass in the costume."

Jackie stood outside the stall in the ladies' room at the pavilion where the party was to take place. Jenny had hesitantly gone along with Jackie on her choice of costume. Jenny had gotten nervous when she saw Jackie's floral wrap dress as Jackie had emerged from the stall first. Jackie's dress was strapless. It wrapped her snuggly around her torso covering her breasts and extended snuggly down to her waist. At the waist, the wrap was somewhat looser and hung down to mid-thigh. Jackie's deeply tanned thighs and calves were plainly exposed. The open-toed sandals with two-inch heels made Jackie's calves curve nicely. Now that Jackie was insisting that Jenny strip completely, Jenny was getting cold feet.

"Come on, Jen, stop stalling. Besides, you have no choice now. You have already given me your shorts and halter-top. If you don't get moving I'll just leave you here in the restroom in your underwear until the party is over."

Jenny had heard Jackie had been somewhat wild in college and was afraid she was getting wild again. For as much as Jenny shared with Jackie, Jenny realized they were still miles apart in some ways. Not wanting to be a complete party-pooper Jenny finally removed her bra and lace *******. Jackie handed in a strip of cloth that Jenny first thought was a dress like Jackie's. As went she started to wrap it around her Jenny realized it was far too narrow. Jenny wrapped it around her waist twice and tied it off at her right hip. It was even shorter than Jackie's dress.

"Jackie, dear, there is not enough here to be more than a short skirt. Where's the rest of it?"

Jackie giggled. "What rest of it?"

Jenny gasped. "I'm *******. I can't go to the party like this." Jenny's voice was almost pleading.

Jackie laughed. "Now you almost know what I felt like yesterday. Here." Jackie passed in a floral string top. Jenny sighed in relief until she pulled the top over her. It was very tight. While it did cover her *******, most of the rest of her breasts were exposed.

"Now hand in my ******* and blouse."

There were a few moments of silence. Jenny peeked out of the stall and found the restroom empty. Swallowing hard Jenny walked slowly to the restroom door. As she peeked out she saw Jackie returning from their rented car with a huge smile on her face.

"Come on out Jenny. You better get used to your costume. It's all you are gonna have until we return to the hotel. Look around you. Everyone else is dressed like us."

Jenny looked around the sandy party area on the beach. Everyone was dressed in skimpy attire. The men were wearing Speedos or equally revealing leisurewear. The women were is bright floral dresses, tops, short shorts and string bikinis. Everyone was revealing a lot of skin, but no one was ****. Island music had started and people were dancing, drinking, and laughing. Jenny realized that everyone else was having a good time. She looked at Jackie and sheepishly walked over to her.

"You are right. I've been at pool parties that showed more than this, but can I at least have some *******. I feel very nervous without any."

"Gotcha," thought Jackie.

"Okay, I'll give you mine to wear, but you have to agree to give them back if I really want them."

Jenny smiled and thought, "Jackie's really a great gal."

The two stepped into the restroom. Jackie removed her ******* and handed them to Jenny. Jackie chuckled as she thought about how she had snipped more of the elastic strands at the waist. Jenny was going to lose those ******* without any other help before the evening was out. Jackie was sure Jenny did not have a clue as to what was in store for her.


The party was already in full swing. Jackie sat at a table flirting with a young attorney from New York, Robert Walkens. Jackie watched as Jenny, with a few drinks in her, was finally out dancing with some blond California hunk named Tad. The way Jenny was shaking her hips, Jackie knew there couldn't be much left of the elastic strands of the *******' waistband. Moments later Jackie saw something peek out from under Jenny's skirt. Another few steps and the ******* were around Jenny's ankles.

Jenny was feeling very relaxed and enjoying the dancing when she suddenly tripped and fell forward into her partner. The blond guy just smiled and helped her up while he kept dancing. Jenny felt something around her ankles. She kicked her left leg to try to free it. As she was being held tightly by her still gyrating partner she could not look down to see what was tripping her up. She now felt something only at her right ankle and flipped her foot to free the ankle. Had Jenny looked down she would have realized she was now dancing away from her ******* that were being pushed into the sand by other dancing feet. Within seconds the ******* were swallowed up in the sand.

Jackie had witnessed the fall and loss of the ******* and was now laughing her head off. She was so distracted that she did not notice that the attorney's hand was slowly working on the knot of Jackie's wrap dress. The knot was now very loose. The attorney asked Jackie to dance and the two joined the others. Jackie, Robert, Tad and Jenny converged and were dancing recklessly to the island music.

Robert went to twirl Jackie and (accidentally?) grabbed the knot at Jackie's hip instead of Jackie's hip. As Jackie spun away the dress unwrapped leaving Jackie stark naked in the middle of the dancing people. Jackie, losing her balance as her shock of being suddenly naked hit her, toppled into the back of Jenny. Jenny felt Jackie's hand fall across her back and snapped the strap of her top. Jenny's top fluttered forward into Tad's face. Tad stopped dancing and smiled as his eyes centered on the two beautiful ******* that bounced in front of him.

Jenny clasped her hands over her breasts and ran toward the car. The wrap skirt climbed up Jenny's running thighs and exposed the bottom half of her ass for all to see. Jackie stood and "Eeked". She made a mad dash after the running figure of Jenny. As Jackie got to the car Jenny was trying to open the door. Of course, it was locked. Jackie realized that the keys were back in her purse at the table in the middle of the party. The two raced now for the restrooms.

Breathing hard, but relieved that they were out of sight in the restroom, the two looked at each other. Between them, they only had Jenny's short wrap skirt.

"One of us has to get our keys," Jenny finally said, looking pleadingly at Jackie.

"Oh, for Christ's sake, give me your skirt and I'll get my purse."

Jenny, as much as she tried, could not come up with a better solution. She unwrapped her skirt and handed it to Jackie. Jenny hid in the stall. Jackie wrapped the skirt around her waist and faced the mirror. She took several deep breaths and smiled.

"Well, it is a little like those college days," Jackie thought. She proudly squared her shoulders and walked from the restroom. "I think I might just stay for a dance or two. Maybe I'm just in a party mood tonight."

Jenny waited for forty-five minutes before Jackie reappeared. Jenny saw Jackie had her purse and the torn remains of Jenny's wrap dress.

"Hi Cuz. Thought you might like this."

Jenny grabbed the dress and wrapped it around herself. She asked, "Where have you been for so long?"

"The guys insisted on an encore dance before they would hand over the purse. What choice did I have?" Jenny was shocked by the broad smile on Jackie's face. "Besides, who's to know? We are down here by ourselves.


The next morning Jackie found out who was to know. She picked up a copy of the NY Post. A picture of her dancing (with very little airbrushed out) appeared in an AP photo in the New York Post as part of the Leisure Trends section.

March 28, 2022 8:30 PM