Ron's Cheer Girls Ch. 02: Cruise

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The top five of the poker party plus June get to the cruise.
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Part 2 of the 4 part series

Updated 04/06/2024
Created 04/03/2024
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DirtBoss
DirtBoss
139 Followers

Disclaimer: This is purely a work of fiction and none of this should happen in real life without full consent. Most of the characters in this story are committing criminal acts. If the idea of human sexual slavery, blackmail, nonconsensual sex, animal play, spanking, flogging, forced servitude, kidnapping, rape, incest, or other such illegal activities bother you. Please don't read this story. Please spend your time reading something you enjoy as this may not be it! All characters are over 18 even if acting like a little for a Big.

Ron had the six poker players assembled on the fetish cruise. They had each gotten a packet on what the expectations were for passengers and how to resolve any breaches of etiquette for the dominants. The cruise would only make landfall in two locations, and both were clothing optional destinations in the Caribbean.

Ron had Red with him in black dress ballet boots that came up to midcalf. The tendons in Red's legs had begun to shrink and it was now painful for her to put her heels on the floor when barefoot. It wasn't happening to the other two he used as servers due to their height and sexual bodies. They were still spending most of their time in cheer shoes. Becky and Rue were spending the vacation time with Pam and her family.

Ron was carrying one over the shoulder duffel and Red carried the other. The trunk with their things had been loaded into the ship before they were allowed to board. It would be waiting inside his cabin. He had purchased a luxury suite with a custom oversized heart shaped bed that could easily sleep nine. Finding the cabin, he closed the door and locked it.

Ron and Red tossed their duffels onto the bottom of the bed and opened them to unfold Kit and Kat from the interior. The two tiny women were naked as usual, he sent the two to get his cabin in order and unload the trunk, getting it organized.

Nancy was boarding in a floral print sundress. She had dieted and attended hot yoga for the last two months so she would look good in her skimpy swimsuits. The 39-year-old MILF had moved her waist from thirty inches down to twenty-seven inches. She was afraid of losing what little she had of an ass and to her surprise the exercise and stretching had increased her hip measurement from 34" up to 36" while hour glassing her waist. It did not affect the 34 strap for her bra or the F-cups for her large tits. It did firm them up in her opinion though.

A small dark young woman followed in a matching dress, carrying a large beach bag for her Mistress. Being in the cat suit had tightened her core down to a 22 waist. If you saw with the light just right you could see the rings through the black nipples of her D cup breasts and if she bent too far you would see the large gold ring behind her bright pink clit, holding back the bicolored onyx and pink hood. Mistress had a short black haired Pixie wig on her with a matching sun hat to her Mistress.

Before Nancy would have used the elevator to go up the seven decks to the Presidential suite, she earned by winning the finals of the poker season. Instead, they took the stairs and Nancy received plenty of appraising glances to her hips swaying in the dress and even the small dark-skinned woman dressed the same as her.

The door said, "Presidential Suite" and a purser was at the door to open it for the two women. "I will be available to provide anything you desire Ma'am" he said.

Nancy looked the mid-twenties aged man. I would request a massage while we get underway, maybe give me a half hour to get organized and then I would have a deep tissue massage. I prefer a man with strong hands.

Before the purser even turned to leave Kitty was naked and, on her hands, and knees. The wig, hat, dress, and shoes were next to the door. The dress was folded neatly on the rug. The wig and shoes were on top of the dress. The shoes were soles up next to the wig. Turning to close the door quietly, the purser could see a tattoo of a white kitten on the lower back of the girl, a gold ring hanging in her crotch and a gold ring through her left nipple. He loved these fetish cruises. You never knew where it was going to go.

Bill walked up the gang plank, hand in hand with his wife that was twenty years younger. He was wearing a pair of slip-on canvas shoes, cargo shorts and a tropical shirt. Wendy was ten years older than the girl that walked behind the two. Wendy had on a lightweight summer pattern dress even though it was mid-December. She wore white six-inch heels and a sun hat. It was obvious that Wendy did not have a bra to hold up the very large fake boobs her previous husband had bought himself. The one following was in a pinafore that went to her knees. She had on a pair of pink Mary Jane shoes, white tights. Her hair had started to grow out, but she still wore the Shirley Temple wig with a small sun hat covered in flowers that matched her pinafore.

Bill's was two suites down from Rons across the passageway. Bill's had no view outside, and Ron's had a door and balcony. He stepped in to find the same large bed dominating one end of the stateroom. A stocked wine cooler had a nice selection of wines and champagne. Bill went to the trunk and turned to the two females.

"Get dressed and get Penny out of her diaper. I want my maid here to serve me and my little girl." Bill demanded, still treating the 18 year old girl like his little girl.

Wendy quickly removed her shoes, hat, and dress. Her 34H breasts came into view she was smooth across her groin, if it would not have been lasered before she met Bill, he might have allowed her to grow back some of her natural blonde fur. Bill had teased her about ringing her like Ron's servers and using Pam's chastity device on her instead of the cable belt he currently kept her in. He had not fucked her pussy since Penny came home with him, preferring the tight 18-year-old Penny, over the well used 28-year-old. When Penny was on her period Bill used Wendy's asshole and mouth, letting his little toy rest.

Amanda had her auburn hair down in loose natural waves and curls. She had a sun hat that matched her yellow knee length cotton dress with a white belt around her 28-inch waist. She had done the same diet and exercise program as Nancy. They started together the day after the poker tournament and were in the same class. They had struck up a fantastic friendship. On Amanda's arm was a cute strawberry blonde in a pink sun hat and pink cotton dress of the same cut as Amanda's and pink Mary Jane shoes.

Following the two dressed so sunny was a taller slender woman in an ankle length black wool dress. She had black knee length lace up women's Victorian boots. The dress was tight around her wrists and came up her throat to the bottom of her chin. She wore white elbow length gloves under the dress. Her makeup might be slightly over done if someone looked closely. The plucked eyebrows may still be a little thick in the center.

Amanda's suite was right between Ron's and Bill's and hers like Bills had the balcony out over the ocean. As soon as her door closed the demeaner changed quickly.

"Francine, I want the chests in there and organized. The contents of our three chests need to be in the closet with your outfits on the right at the back. Buffy's should be the same side at the front. Mine will be on the left side. Little Buffy and I are going to be relaxing after the trip." Amanda asked, while she was lifting the pink dress off her delicate toy.

Buffy had improved a bunch. She could now carry-on high-level conversations if she was stimulated slightly. For a trip like this she had to wear the inserts that Robert had broken her mind with on at least level two with the light shocks to keep her from orgasming. There was nothing Buffy liked more than worshiping the woman's body that had been helping her slowly get some normal in her life.

Buffy loved how firm her mistress's waist had become since she started her workouts with Mistress Nancy. Mistress Nancy was nice, and her Kitty was fun to play with. The pussy serving abilities the small black woman showed on Buffy made her shudder in pleasure with the memory. Amanda removed the belt and two inserts, after the dress and Mary Janes.

"Sweetie, go and clean up your messy crotch for me. On the ship, the bathroom is called the head. So go into the head and wash that mess from my crotch." Amanda instructed while she was removing her dress.

"Yes, Mistress." Buffy said, hurrying across the room to the bathroom, she giggled as she called it the "Head" in her mind.

Amanda went to check on Francine's progress. She had one of the chests mostly cleaned out and hanging in the closet. Amanda noted most of Francine's clothes were in the back right of the closet already.

"Since your things are mostly unpacked, I want you in the pink and lavender maid's outfit, in the pink ballet boots before you come out to attend myself and Buffy." Amanda told her maid.

Amanda opened a bottle of champagne and waited on top of the heart-shaped bed for her freshly cleaned slave to come out and worship her.

Ezra was dressed in khaki shorts, a cream button down silk shirt, a pair of light tan strap sandals and a pair of high-end sunglasses. The woman holding his hand was eight years his junior had given him her maidenhead on the morning after the poker tournament. She was in a pair of four-inch heels. Her pale skin showed at the top of the thin dress, covering her E cup tits with the thin red material of the dress that went just about five inches down her thighs. She had styled strawberry blonde hair to the center of her back. The firm natural breasts had just enough bounce to let anyone looking know they were not held against gravity by a bra and natural.

Ezra and Paula had been on a serious workout regime since that loving morning when instead of in the those of Ezra's teasing and a couple of hard seltzers, Ezra had softly, slowly, and lovingly taken the small woman's virginity, finishing with a nice orgasm for her and a vagina full of seminal fluids for him. Paula had turned into an absolute nymphomaniac since that morning.

Ezra had even gotten one of the make your own dildo kits to make an exact replica of his hard cock for her to use on nights that he was too tired or busy. She could now put her chin on his scrotum and hold it in her throat until she started to go into pin vision and eyes roll back. Ezra had never had a girlfriend like her. She had made him promise to take her anal virginity on this trip since he already owned her other holes.

Ezra, being last on the cruise with his fourth place, had paid the difference and gotten the suite next to Bill and his wife. Walking into the suite both were naked on the bed immediately and petting each other. Ezra spun the girl on his chest to access the core of her with his mouth and tongue while she got him ready to bang her guts with his thick cock.

June had bought her way on. She had been first out of the tournament but wanted to be invited next season as well. Her ex-husband's estate had made it, so the woman did not need to work. She had taken the assistant job at the university so she could meet people and make friends.

June had hired a personal trainer to help her get ready for the cruise. The forty-year-old felt like the woman had done a good job. She was down two inches on her waist, back how it was in her mid-twenties at 28 inches. Her hips hadn't changed measurement but the cellulite in her thighs was gone, and she was toned enough to see the muscles in her legs. The best part in her opinion was that her bra strap went from a 36" back to the same as it was when her waist was 27 to a 34F. Her breasts were much firmer and sat up higher on her chest. Her little Mollie kept telling her Mistress through the process to stick with it, Mistress was lovely.

Mollie at 5'0" was eight inches shorter than her much larger Mistress. June had more than once threatened to get her breasts reduced and have the doctor put the excess into her little 18-year-old, Mollies 30A chest. It was an empty threat as June loved to play with the small cones on the tiny woman's chest and Molly loved to become lost worshiping her Mistress's chest, covering it with soft licks, sucks, and nips.

The two walked up the gang plank June wore a white silk blouse with a visible white bra under it. Her long peasant dress hid the Victorian short boots on her feet in black leather. It also hid the white thigh high leggings with a garter belt and hooks on the stockings. One of Mollie's responsibilities was every morning before Mistress went to work was to carefully shave her Mistress's crotch and keep the thick v shaped hair directly above June's cleft.

Mollie wore much the same outfit but sans bra. Her pink nipples could be seen though the silk blouse and her skirt only came to the knee showing her Victorian leather boots and white stocking disappearing up her skirt to the garter and clips on the much smaller woman. June loved the look and anyone closely watching could catch June running the back of her arm across the nipples of the strawberry blonde or sneaking a hand up the side of the skirt and rubbing on the bare pussy of her toy.

June led her mini me to the suite right on the other side of Ron from Amanda. This put the group in three ocean side balcony, Fore to aft was June, Ron, then Amanda. On the other side of the passageway was Bill and Ezra. One deck up on the same area of the ship was Nancy and her Kitty.

The ship's horn blew as the mooring lines were removed from the dock davits and pulled onto the ship with winches. There was a knock at Nancy's berthing door. Kitty was in her new white leather outfit. On the bed between Nancy's legs, doing one of Nancy's favorite past times. Kitty was cleaning up after a particularly hard orgasm by her owner.

"Come in!" Nancy yelled.

The man coming in looked like one of the models on the front of women's softcore novels. He had olive tan skin, black hair that flowed to his shoulders. A white silk shirt that was open between his pectorals and dark grey shorts. His white deck shoes were canvas and had no laces. He carried a large beach bag around his shoulders and a massage table folded under his right arm.

With a thick accent he said, "I am Omar your masseuse. I was told by the purser that you wished for a deep tissue massage as we set sail. Would you like to look out on the harbor as we leave, and I work the tension out of your muscles?" Omar asked.

Omar was fascinated at the odd fetishes some of the people on this annual cruise had. He watched as the naked woman lifted the small woman in the leather cat outfit to the floor. The three tiny bells attached to the three rings tinkled as the girl walked on her elbows and knees. Not only did the woman have large breasts, but the kitty did also.

Omar set the table up looking out the balcony sliding door. Omar guessed the woman in her early to mid-thirties by her tone and firmness of her body. He had just turned twenty-eight a few weeks ago.

"I assume you are comfortable without a cover?" Omar asked the naked woman.

"Oh, yes and don't leave a muscle untouched. I expect thorough and your tip will reflect it." Nancy said, as Kitty explored the cabin without sight.

Kitty felt the warm sun on her leather covered back and lay in the sunlight coming in the window where she could hear her Mistress grunt or groan occasionally. Kitty heard her Mistress stirring and Omar spoke.

"Ok, please lie on your back and try to relax. Now if I am doing something that makes you uncomfortable just let me know as I am not trying to be sexual but massage the tissues of your body." Omar said.

"I already told you "Every Muscle" if I feel like you're taking advantage of the situation I will let you know. I am not some prude that won't let you do your job." Nancy said.

Omar started on her scalp and worked his way down her face to her neck. Nancy could feel the tension leaving her body. Her shoulders, and out each arm. The feeling of him massaging the muscles of her hands was erotic. She could feel it in her core as she relaxed even more.

"I need to get the pectoral muscles under your breasts then I am going to break up the crystals of hormone that have collected in the ducts of your breasts, sometimes it will be painful but once done you will feel much better." Omar said.

If that was his excuse to play with her tits she did not mind. As she felt after what he did to her hands, she could use a little breast attention. He started below her armpit with both hands and pressing hard with his middle and index fingers. He was right about the pain. He worked around the circumference of each breast and occasionally he saw her wince.

"You need to relax, if possible, Ma'am, these muscles are the ones that are the main supports for your breasts, and they seem to be full of toxins. I would recommend a mammogram when you get home. I know it is early in your life for that but the amount of toxins I feel are going to make you feel like you have the flu the rest of the day, about an hour after I finish." Omar explained moving up onto the slope of the breast continuing the same pattern of working the circumference of the organ.

Nancy swore she could feel things like crystals shattering in her breasts as he pressed with his fingers and continued the circles of her breasts. Fluids started to evolve from her nipples, and he would wipe them off.

"If it would help get the toxins out, I don't mind if you suck them to get that out." Nancy said, joking.

"Thank you, Ma'am, it will make it better for you, but I don't ask women for that as it embarrasses most enough to have me pushing on the tissues like this." Omar said.

It took four complete laps around the breasts to cover the size of them with his technique. He estimated he had swallowed ten to fifteen milliliters of fluid evolved from the ducts of her breasts. He worked his way down her now toned abdomen getting to the lower abdomen. He started on the pyramidalis muscle below her belly button and move to her hip flexors and sartorius that went up the inner thigh near the connection between the thigh and the outer vagina.

Omar worked his way down the left leg first and when he got to working on her foot, Nancy almost orgasmed with the manipulations. Lucky for her he started back at the hip flexors and sartorius on the right leg. He worked down to her right foot with the same reaction as the left.

He took his hands off and asked, "How do you feel Ma'am?"

"I feel like there are a few muscles you have missed. There are also some tissues in deep that need to be massaged. Kitty come find Omar and get him ready for your Mistress." Nancy ordered. "The muscles from here to here were not massaged, also inside my vagina that tissue needs a deep massage. Feeling this, I am ready now I just need you ready." Nancy said dipping her two fingers into her sopping vagina.

"Here Kitty," Omar said as he pulled his shorts off and lay on the deck.

Kitty was amazing how she could get his cock up and into her mouth without hands. Omar was quickly hard and standing at the foot of the table. He pulled Nancy to the foot of the table. Taking his fingers he began to massage from the belly button down to the opening of her cleft. Where he sometimes saw it, as he massaged the muscles between the vagina and the ovaries Nancy orgasmed in a soft way.

"Fuck me, god fuck me, Omar." Nancy began to beg.

Omar lifted her knees into a birth position, exposing the wet arousal to himself, "Hold these here." Omar instructed.

Nancy followed the direction and was rewarded with Omar's thick seven inches sliding slowly into her core. He continued to massage the muscles of her lower abdomen as he stroked her vagina with his cock. As she was panting and nearing her summit, he pushed down on her abdomen in four locations with his fingers and thumbs. Nancy had the most shattering orgasm of her life. Omar at the same time shot his seminal fluids against the inside of her contracting vagina.

DirtBoss
DirtBoss
139 Followers
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