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Cutty

Copyright© 2019 by bokkey

Chapter 22: The Caribbean

Erotica Sex Story: Chapter 22: The Caribbean - The mysterious ms Brendan wants a lesbian relationship with Donna, and more...

Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft   Fa/ft   Blackmail   Coercion   Slavery   Lesbian   Heterosexual   Fiction   Slut Wife   BDSM   DomSub   FemaleDom   Rough   Spanking   Group Sex   Oral Sex  

Aaah, the Caribbean!!

From the moment Donna stepped out of the plane on to the steps she was in heaven. The bright sun, the soothing wind, the open space, the palm trees. She almost immediately stopped worrying and knew this was what she had yearned for for a long, long time.

Her daughters were equally enthusiastic, taking up the surroundings with a big smile just like she did.

The walk from the plane to the gates across the landing strip in the open air was odd, but totally fitted the vacation feeling. They strolled together with the other passengers over the runway looking around, inhaling the fresh hot air.

In the distance even the blue see could be seen, and everywhere the small picturesque tropical buildings. Would people really live in those small wooden houses?

Everybody took the long wait at customs for granted, as well as the baggage check, where the old rusty belt’s noise filled the hot hall, as it deposited the luggage one ... by ... one...

Yet all the local people were friendly, and assisted everybody, be it at a Caribbean pace.

And the ladies started immediately to make plans what they would do first. It was already in the afternoon, so they figured the beach was out of the question, but there was so much more to do they saw as they went through the leaflets distributed.

After customs came the fight for a taxi, and next they found themselves in a minivan being driven across the island to the hotel. The trip itself was an adventure, with the small roads, the cars cramped on it, and the holes in them.

The driver excused himself for the inconvenience, but the December rain had done its work on the state of the roads, and it was high season, so the roads were bad and crowded.

They didn’t mind as the enjoyed the views. Especially when they went over a hill the view was breathtaking. The green valley, the sea in the distance, the shadow of a small single cloud gliding over the island.

And the special moment for Donna when Lisa laid her hand on her shoulder from behind and said: “Look how beautiful, mom. That hill with the big houses, and those trees blossoming!!”

Donna smiled back and looked her eyes out too, but above all she was happy as she knew Lisa had forgiven her. This trip started fabulous!

Next big surprise was the hotel. A beautiful large colonial building in between two steep hills, with the sea in the back. The women got out of the taxi and just stared at the surrounding.

“Is this for real, mom?” Trixy asked.

“How could you afford this, mom?” Lisa added.

Donna herself was dumbstruck too by the grandeur of the hotel. She knew it was high class, but this surpassed her expectations by far.

“It’s a good hotel.” The taxi driver understated as he got their bags.

The ladies looked around. The hotel had a large green garden in front of it, with a few large trees, and green grass. Flowers blossomed everywhere.

A friendly bellboy came outside to pick up their luggage, and escorted them into the lobby, where Donna and her ‘s daughters jumped from joy again. It was so overwhelming.

Big fans hung down from the roof, and gently swayed, causing a gently flow of air in the hall, creating an acceptable temperature. The decoration inside was done in the colonial style of the building; large old wooden chairs, heavy wooden tables, paintings of various historical figures on the walls. Even the employees were dressed in a colonial like attire, and all very polite.

After the quick check-in they were led to their rooms, were the final surprise awaited them; they had sea view, and not just any sea view!

Their adjacent rooms shared the same large balcony, from which the back garden, the white sandy beach, and the see could be seen, with in the distance small islands sticking out of the water. It was picture perfect!

They just glanced at the view, and at each other, not believing they actually were there, in the Caribbean, in such a luxurious hotel.

They drank their complimentary fruit punch, loaded with rum which Donna allowed for once, right there on the balcony, as they giggled, laughed and just enjoyed the moment.

Donna walked into her room and opened her suitcase on one of the beds. She wanted to shower and get out of her travel clothes as soon as possible. She went through the clothing in her suitcase and was amazed, no appalled, by what Ninon had packed.

All skimpy dresses, shorts, and underwear. Everything way too revealing to wear, even on the beach. She rumbled through trying to find a decent piece of clothing but really couldn’t find any. She had packed only clothing she wore when she had to fuck her or Ms. Brendan.

“They want me to dress like a filthy slut.” She figured with a smirky smile on her face, as she held up a ‘night dress’ which was no more than a few straps of cloth.

She shook her head.

“But that is not going to happen...” and she threw the item back into the suitcase.

“Ladies!” she shouted at her daughters, “We gotta go shopping right now!!”

Enthusiastic cheers were the response, and soon the three ladies were in a cab heading to a local mall.

By the time they arrived back at the hotel it was already dark, and they again were marveled by the view of the hotel and its surroundings. This time the garden was lit beautifully with torches, and people were dining in the garden under the stars.

You could hear the sound of their talking, together with the soft clattering of the plates. The hotel itself was lit by some beamers and stood majestic between the dark hills on each side. In the back the moon shone, lightning the see dark blue. It was like a dream come true.

Donna and the girls hurried into the hotel to shower and change, as they were hungry.

Donna had bought a whole new set of clothing so she could dress normal. She had no intention of using the clothing Ninon had packed for her.

“If they want some pictures of me in them, well we’ll dress up one night and give them some.” She figured.

The whole vacation already had a good effect on her mind set she found: “But let’s enjoy dinner first.”

And enjoying they did! The food was excellent and the service impeccable. They all ate their belly full, and Donna enjoyed a few glasses of wine during and after, as they sat in the garden. A soft breeze was cooling them down, and the stars twinkled up above.

The soothing atmosphere had healed her relationship with her daughters completely. They chatted, gossiped as they used to do, and they planned the next coming days.

A happy, very happy Donna went to bed that night. Gone were all her worries, and she fell asleep in the soft clean bed almost instantly.


The next days went by in pure bliss. They visited the beaches by day, did some shopping in the afternoon, ate at picturesque restaurants, preferably with see view and when the sun was setting, and at night they partied.

Donna forgot all her worries and enjoyed life to the max once again. She and her daughters bonded, and they became close again. So much happened on the vacation that they just didn’t talk about what happened back home anymore.

And Donna was content to see her daughters acting normal. Her fear her tormentors were on to them too seemed unjustified.

They contacted Robert every night just before they went out to party. He was obviously lonely and a little jealous, but they all said they were missing him, and proud that he was doing such a great job. It usually cheered him up, and with the reminder that they would be together at the end of year, and would party all together, he was content.

Of course, men approached them often, but she was used to that by now. She taught her girls how to fend off men in a nice way, or how to haul the nice ones in. Her daughters knew a few tricks, but Donna was amazed how much more experience she now had and could share.

After the weeks of flirting in bars and other dubious places these men were a piece of cake to her. She could size them up one time, and tell her daughters what to do, what to say. And every time her tricks worked.

As a result, they could dance at night, swim at a beach, and no one bothered them too much if they didn’t want to. Donna was kind of proud she could help her daughters like this.

She loved the role of the mother who watches over her daughters as they flirted. On the beach she usually just took a beach chair and let the girls swim and meet boys. When she didn’t like the guys they hung out with, she called them over for a ‘drink’, and explained her worries.

In the disco at night it was just the same. Be it she drank a bit herself and therefore was less sharp. As there were so many boys around, they followed her advice usually, meaning they dumped the guy and just waited for the next one.

Donna herself never had such a freedom as she gave her girls. But she had always yearned for it during her teenage years. Though she never really wanted to have sex, the attention was something she had craved. But her parents never really had let her go, up until she went to the university, at which time she needed to study to secure her future.

True Robert came in between, but she had been very serious about her study up to that point. Thus, she wanted her daughters to have a different life. Enjoy the teenage years some more, and what better place to be a bit wild than the Caribbean? And also, she knew if she held them on a tight rein, they would rebel anyway.

As for her own sex-training as a whole, with its schedules, its exercises, she did keep to it as much as possible. That is, she did watch what she ate, as she knew every pound she added would be noticed and would cause problems. And she loved her figure.

Also, she went together with the girls to a spa one day, doing the works as she was used to, manicure, pedicure, massage, waxing, the works. She basically watched she wouldn’t go too far off from her current shape. And the spa was the one thing she loved from her new life anyway.

However, the specific slutty clothing was totally abandoned. No more ridiculous high heels, no more extremely short dresses. Her new wardrobe had taken care of that. But she did choose clothing that showed her new figure off. She hadn’t endured so much hardship to get it not to flaunt with it. And it was the tropics, so the average clothing was short anyway. In other words, she made sure she looked hot, but in an acceptable way.

She did acknowledge to herself her clothing was more daring than she would previously wear, but she didn’t mind. Her old self had been a bit too careful. As far as her ‘itch’, the medicine did work. The ointment she had gotten ‘cooled’ down the itch, although it came back full force when its healing work faded after a few hours.

Luckily, she had a bunch of tubes with her, and she carried one always with her. Also, in that respect, she did still give herself an enema, be it every other day. She had been embarrassed when she went through customs and the officer saw the bags, but he hadn’t known what it was, or just politely ignored it.

She was Ninon actually grateful she had packed the kit, as it helped with the itch which went deep inside her asshole. The cooling liquids of the enema had a softening result, and it was impossible getting the ointment there. And she felt the enema cleaned her better anyway. She was used to it too, just like brushing teeth.

A bit of a problem was the side effect of the ointment with respect to alcohol. She couldn’t drink too much when she used it. After just a few drinks she would feel herself getting drunk, if not wasted, so she had to take virgins in between her normal cocktails. Problem solved.

Ninon had packed a few dildos too, but Donna had thrown them away in the garbage bins in the toilet, determent to be her old self during this vacation. It was another act of defiance she was very proud of. Be it, she was a bit embarrassed when the cleaning lady was busy, but she showed no sign she noticed the dildos when she cleaned the bins.


As the days passed, she became more and more resilient at the scarce moments she thought about her situation. She cursed herself for being so weak. Especially for her acts at the beginning, going to Ms. Brendan’s house and getting the cut in her vagina.

But also the weekend, where she was practically raped, infuriated her. She should have stopped it right then and there. How could she let her house be remodeled to the wimps of a lesbian bitch? And she even worked for her to make the payments!

But she did realize she had turned a point when she signed the contract, making her a willing prostitute, or call-girl. She figured that was her only real problem right now, as she could face legal charges, and probably would.

But she needed to get things in the open with Robert next. Together they could handle all the problems they would face eventually, she figured. And if they lost everything and she had to do time, so be it. Especially as the vacation reached its end she was more and more convinced she should stop it, she could stop it.

In addition, Donna came up with a plan for the pictures she needed to make for Ms. Brendan. First of all, she wanted her daughters left out. She knew Ms. Brendan wouldn’t approve, but she was determined to protect her daughters.

Indeed, her girls had gotten sexy bikini’s just like hers, but they didn’t wear them either, obviously because they were just too skimpy. Even for these beaches full of topless European women and girls. The design was just too much focused on sex. She would be less inviting if she just wore nothing.

She couldn’t believe they could make bikinis that small, or that people would seriously consider wearing these. And she had like 5 pairs, with two of them being nothing more than a bunch of strings knitted together, covering nothing at all.

As far as the pictures, Donna figured she had to model them in different places, so it would look like she had taken them at different days. She couldn’t possibly explain her actions if her daughters were there, so she had to get rid of them for one day.

So, she planned to party all night, so they would sleep the whole morning, and she would then cruise the island and make her shoots at various locations. No one was to see her somehow, so the shoots had to be early in the morning, when the beaches were still rather empty.

Also, she had found several locations near the hotel where rocks or trees prevented the surrounding to see her, and the spots were usually rather empty as they were difficult to reach. They themselves only had went there because she was looking for a place for the shoot, although her daughters thought she was just being adventurous.

As for the other sexy attire she had, she figured she would stay at the hotel the remaining of the last day, and wear them in her own room, and maybe in the garden too. If she sat in a corner with a towel nobody would see too much.

And the girls could go out on their own for a day. She trusted them by now, and, also, she trusted the island. She figured she had not much to worry about them by day.

And the last night on the town she would wear the evening dress Ninon had packed for her. It was way too revealing, but Donna figured if she wore it only the last night, and they went immediately into one of the clubs it would be too dark to see anything anyway.

And she knew one were some girls from the nearby adult club came too, and they wore similar clothing, if not more revealing, so she wouldn’t be the only one. Or better, people in that club were used to girls, ladies dressed skimpy.

All in all, she had it figured out. She even had bought a new camera, tax free, for the shoot. The night before the shoot she told the girls she was planning to tour the island early in the morning, while they slept. The girls agreed and thought nothing of it.

They knew their mother wasn’t partying as much as they did, so she always woke up before them. Whatever she did before they woke up wasn’t really important to them.


Late in their night out, as they were about to leave, Lisa came with a couple of local boys to their table. Donna knew them, as they had met before on several occasions. They seemed to party as much as they did but had never bothered them too much.

“Mom, look this is Dalmar, a nephew of Dwayne. He is from the states too.” Lisa said.

Donna looked at the new boy in the group.

“And guess what; he is even from the same city!”

“Cool!!” Trixy said.”Come sit down with us.”

Lisa invited the group. And the whole bunch of six to seven boys sat down.

“So, you are here every vacation?” Lisa started to chat with Dalmar.

Donna saw she obviously had the hots for Dalmar. And she had to agree he was good looking. He had muscles, obviously he worked out a lot, and he had a cute face. He was light dark and had beautiful dark eyes.

“Well, not every vacation, I am not that rich.” Dalmar answered politely, “But as much as possible, yes.”

“And where are you from, I mean, which district?” Trixy asked.

She was obviously also impressed by his looks.

“The Bashenee part.” He said.

As he saw their reaction he smiled and continued as he saw her looking doubtful; “Yes, yes, I know, it is a bad part of town, a ghetto. But my parents aren’t rich, so they had to settled there. And the neighborhood went down while we grew up. I’m making the best of it to get out of there.”

“Okay, sorry for our reaction.” Trixy said, saving the situation. “Let’s drink on meeting each other here on this beautiful island!”

And another round came. And after that another one. And the mood got better, the music got better, and they all danced and had fun. As the night passed Lisa and Dalmar became closer and closer. She begged Donna and Trixy not to leave her, and wait for her, and thus Donna and Trixy were stuck too. There was no way Donna was going to leave her daughter behind anyway.

But staying longer as planned meant also drinking more as planned. The medicine- alcohol combination, the long day in the hot sun, it finally got to Donna and she became drunk. Really drunk. She kind of lost control of time, and just vaguely saw, understood what was happening around her. As if her life passed by like a stroboscope.

She remembered leaving the disco-bar early in the morning. Lisa and Dalmar were an official couple at that time holding hands and making out. Both seemed to be totally in love with one another.

Donna heavily leaned on Trixy, who was pretty much under the influence of alcohol too. Even though she had not been allowed to drink by Donna. They decided to grab something to eat at a local bar. Most of the local boys didn’t go with them, but Dwayne, Dalmar and another friend stayed with them.

Next thing Donna recalled was driving home to the hotel. She sat in the back of a car, together with Trixy, and Lisa was in another car with her Dalmar. Trixy was looking at her kind of worried, but as Donna had a clear moment, she explained her she needed to drink a lot of water, and she needed a shower.

And next everything became a blur again.

They were brought back to the hotel, and Donna found herself being undressed and pushed into her shower by Trixy. She didn’t know how long she stayed under the soothing spray of water, but she did sober up a bit. Enough to start worrying.

At first about her shoot she had planned, but then it occurred to her three local boys were in their rooms, and she had no idea what was going on. She quickly grabbed a towel and stumbled to the balcony. She even had problems walking straight.

As she walked up the balcony, she saw Lisa heavily kissing Dalmar, and Trixy was being fondled by a boy she didn’t know. Dwayne was looking on and smiled as he saw her entering. He obviously hoped to get his girl tonight too, and that was her.

Lisa got up when she finally saw her mother struggle with her balance. She walked up to Donna and together with Dalmar and Dwayne brought her back into her living room.

Donna felt the boys feeling her up a bit but was to slow to fend them off.


When she came through again, she was being dressed by Lisa. She looked at Lisa and saw her dressed in her micro bikini.

“What?...”

“Shhh, mom. We are going for the beaches with you. You rambled to us about taking pictures wearing bikinis, and we all liked the idea.” Lisa said.

Donna slowly looked at herself and saw she was wearing one of her bikinis too, just like Lisa. By that time she was told to stand up already and some high heels were fitted on.

“You look great!” Lisa said enthusiastic as they both posed in front of the mirror.

Donna wanted to object but was still too drunk. She saw herself wearing the bikini, a loose short t-shirt, and a wrap around her middle. She was standing in high platform wedge shoes. She recalled Ninon had packed these. Her face was made up with thick layers of liquid foundation, her eyes were done heavy with black eyeliner, her lips a bright red, and her hair was combed and looked wild.

“You looked awful.” Lisa explained, “So, I just bathed you quickly, and quickly applied this make up, a bit the way you do when going out with Ninon.”

She turned the face of Donna to meet her eyes.

“Look mom, I really, really like Dalmar. He is nice, makes good jokes, is very sexy, actually he is fucking hot. You mentioned pictures, and I want to seduce him with those, so he never forgets me, and we’ll meet again back home.

“He was totally taken by our bikinis once we showed them what you bought us, and he wants me to show it for him. I don’t dare to do that alone, but I already convinced Trixy to participate, and I figured you would too. You mentioned the picture shoot, and you bought this stuff.”

Lisa looked her mother pleading in the eye, “ ... And you actually owe me a favor still, right? After that hit on my nose?”

Donna slowly nodded yes, and she felt herself being taken onto the balcony. The mentioning of her hitting Lisa had broken whatever resistance she had left.

“My mom is ready!” Lisa said to the waiting boys. “Let’s go for the shoot!”

Donna vaguely saw the look of the boys as they eyed the women before them, but next thing she knew she was sitting in a car driving towards a beach. Warm wind was blowing into her face, and the sun was definitely up.

By the time they were settling on the beach she had recuperated enough to be present, be it she felt lightheaded still, and a bit sick. She was taken by Lisa to a palm tree on the beach and told to strike a pose. The shoot started immediately.

The boys cheered them on, and her girls became more daring. Better, Lisa became more daring, and she instructed her sister and mother to get rid of the T-shirts, and the wrap.

The boys kept on taking pictures and told them they looked beautiful.

Even in Donna’s state she knew this was wrong, but she was still too out of it to act against it. She just went along and posed alongside her daughters under the palm tree in just the micro bikini. The girls had to help her several times from falling, which was a sign to her she was still pretty out of it.

When they got a break, she asked for water and drank a whole bottle immediately. She was back now and considered her situation. There were three boys horny like hell taking pictures of them, urging them on to be more daring.

The beach they were on wasn’t one she had chosen, and though it was early, people started to appear. She looked at her daughters. They were dressed similar to her, be it Trixy wore a larger yellow top which covered her whole nipple and areole and a matching bottom with a flap in front and behind of it, hiding the extreme small thong underneath. She was the one dressed most decently.

Lisa wore a blue bikini, but the top covered only her nipples and part of her areole. Her bottom was without a flap, and small and tight. Donna could see the outline of her lips clearly and knew they would show on the pictures too.

She herself was in and identical bikini, be it her breast were larger and hung more. It meant she had to constantly adjust the top as she moved into a different pose. Her nipples were showing constantly, and the small top didn’t cover near enough.

They all three wore the same beach shoes, the platform wedges, and in matching colors. She knew Ninon had bought them for the girls, of course saying Donna had.

She found the situation they were in frightening, and they had to get out.

On top of that she felt her itch come back full force, as the string bottom scratched her gently as she moved her legs, making her vagina react like crazy. She felt her juices stream inside already, and it would only be a matter of time before her bottom would be soaking wet.

“Let’s do some shoots in the sea.” Donna said as she finished the bottle of water.

She just had to hide her wetness fast. She figured they were less exposed in the sea also. And she could even scratch herself.

“Good idea!” Lisa said, and she stood up. “Let’s go!”

Trixy got up too, and the both of them ran to the sea chasing each other playfully.

Donna had to admire the way Lisa flirted with Dalmar. She made sure she played the innocent girl. Laughed a bit overdone, but not too much, and of course she made sure she touched herself nicely as she brushed off sand when she got up. Even giving him a seductive smile when she continued her chase after Trixy.

Donna walked quickly to the sea too, but for different reasons. Even her ass was on fire now, and she hurried into the warm Caribbean sea.

“Come on, group picture!!” Lisa shouted to Donna, as she already posed with Trixy as they stood halfway in the sea.

The strong waves pushed them forward and backwards all the time giving Lisa ample opportunity to flaunt her assets once more. Trixy joined her game, and started to pose sexier too.

The boys complimented them, howled at them, and told them they were amazed at such beauty, and dared them to show more. Donna joined her girls and tried to calm them down.

But she was herself distracted by her itch, and embarrassed when she heard Dwayne shout: “Trixy, grab your pussy just like your mom does!”.

She was just scratching herself, and a big wave had sucked up the water, exposing her actions. Donna stopped immediately, and not knowing what to do just smiled and hugged her girls playfully, trying to distract the attention from her back to them.

The next embarrassment was when she noticed the bikinis where see through when wet. And thus the boys could clearly see their nipples, and the outline of their pussy lips. They were all three practically naked, parading in the water.

In addition, the coldness of the water had hardened their nipples, adding to their exposure. She saw the boys zooming in with the camera, and laughing at each other.

“They must think we are three dumb bitches.” Donna thought. “If we just get it over with, and I can scratch myself, we can get out of the water, and dress up, at least put towels around us.”

But Donna hadn’t counted on Lisa, who was determined to seduce Dalmar. She kept on pushing the boundaries.

First, she touched her nipples as a joke, but soon she was seriously caressing her nipples through her bikini and smiling at Dalmar. She encouraged Trixy to do the same, who didn’t want to look too prudish, and followed her behavior somewhat.

Donna had lost control, and all she could do was smile, and pose as if she didn’t see, mind, her daughters’s actions. Her own mind was busy with her itch which was even worse in the sea. The saltwater burned into her outer lips and asshole rim. She just had to scratch herself.

And the stupid waves kept on pushing her from side to side and pushed her breast from under her bikini exposing them. She had to constantly adjust her top, or better, the small piece of ropes. She cursed her sagging breasts.

If they had been a bit stronger like her girls she would have had less problems. Now they just flopped out of position every time.

Luckily it finally ended when the boys ran in the water too, to playfully catch the girls. Donna figured they were just too horny to continue and had to touch what they had seen. She herself used it to swim deeper into the sea and pretended to relax taking up the surroundings.

Actually, she was scratching herself like crazy, standing up to her neck in the water.

“What a relief!!” she thought as she entered a few fingers in her ass and gently scratch her bowels.

Her other hand worked on her vagina, scratching her outer lips, also going inside.

“Hello lady...”

Donna opened her eyes wide and looked around. The unknown boy had swum up to her while she was scratching herself. She knew he must have seen her as he was pretty close.

“I see you can’t wait.” The boy said with a big smile. He had seen everything alright “Mind if I help you?”

“No thank you.” She said angrily, “I can do it myself.”

It was an odd thing to say, as it confirmed she was masturbating herself, which she actually was not. But Donna saw no point in denying her actions. She just wanted the boy to leave her alone.

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