Cruising the Caribbean Pt. 01

Story Info
Kimmiann discovers all the pleasures of kinky sissy cruising.
2.9k words
4.35
6k
6

Part 1 of the 1 part series

Updated 02/15/2024
Created 02/05/2024
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

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

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

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

Click here
M_Suzanne
M_Suzanne
27 Followers

I've never been on a kinky cruise, but I certainly hope this is exactly what they're like. Thanks for reading and enjoy!

Things were progressing nicely for kimmiann and her Mommy Mistress. At home, kimmiann was often the sissy femme gurl her Mistress wanted. She only wore her 'male' clothes occasionally now and was always in panties and chastity.

Mistress Suzanne embraced her true Dominance and kimmiann's submission has become second nature for both of them. Even in vanilla settings, the subtle signs of their D/s relationship are there for people who know what to look for.

M Suzanne is formidable when the strong, powerful woman she truly is, emerges. kimmiann has found peace and happiness in the submissive role she always wanted, but rarely found, in her previous vanilla life. Their D/s is built on their profound love and respect for each other and that's why it endures.

kimmiann found a cruise line that offered kinky swingers cruises and M Suzanne booked them on an upcoming trip. It was a Caribbean cruise with a BDSM component and dungeon and other playrooms.

Mistress had been training kimmiann to be a slut for alpha men. kimmiann's slutty cum holes were made to be dominated by a Daddy, but so far most of the Grindr hookups, Fet dates and SilverDaddies meet ups had flaked and/or ghosted them. It had been frustrating so they were very excited for the action they hoped to see on this cruise. They were ready to meet other safe, like minded people, and maybe connect with another couple or two.

The cruise had costume nights so there was alot of packing to do. M Suzanne told kimmiann that she was only allowed to pack femme clothes, as she would be femme for the entire trip. She picked out kimmiann's travel outfit of black leggings, a tight white t-shirt with a pink bra underneath and pink sandals.

She allowed her to wear her pink plastic cage in order to get thru the airport metal detector. kimmiann was excited and humiliated but like always, she did as she was told. Mommy Mistress knows best. M Suzanne packed a play bag that, if TSA opened it, would be the topic of conversation in the breakroom.

As usual, they barely got a second look from the other travelers. They had come to understand that once they confidently embraced and owned who they were, without apology, that most other people followed their lead. They got to Florida and were soon boarding the ship, bound for the Caribbean. Mommy Mistress, having never been on a cruise, didn't know what to expect, but was glad that her first cruise was a kinky one.

As they made their way to their cabin, they greeted other couples and were pleased to see many were older and in their age group. They talked with their neighbors in the next cabin and everyone seemed to get along well. Their dynamic wasn't D/s but the husband was bi and Mommy Mistress and kimmiann were hopeful for some exciting adventures.

M Suzanne always wanted a MMF threesome and it seemed possible on this trip. She wanted to look into the eyes of the man penetrating her pet as kimmiann licked her to orgasm. And she wanted to feed kimmiann another man's cum from her pussy.

She craved sharing a bed with kimmiann and another bi male, watching them kiss and enjoy each other sexually, but also having the attention of them both on her. The mere thought made her pussy drip. M Suzanne and kimmiann fully supported each other's kinky desires and they couldn't wait to see what this trip would bring them.

The cruise had about 1000 couples aboard. There was a meet and greet starting in an hour so they had some time to get ready. Mommy Mistress told kimmiann to put on a new floral sundress with her pink collar while she wore a black maxi dress. She put a cute blonde bob wig on her pet and some light makeup. Her legs were always shaved now and nicely toned and tan, so Mistress ordered her to just wear low kitten heels.

When they got to the banquet room, people were mingling and kimmiann got her Mistress a drink and stood quietly by her side. kimmiann had learned to walk like a lady and M Suzanne proudly watched several men eyeing kimmiann as she walked across the room. Soon one came over.

He was an older man, nice looking and his female partner was talking with another couple. He respected their dynamic as he spoke directly to M Suzanne.

"Nice to meet you, I'm Ted and I'm admiring your sissy gurl and look forward to getting to know her better this week."

Mistress responded, "I plan to have my pet taken by a dominant Daddy on this trip, one who will show her how to truly be a woman. I want to enjoy watching her get fucked like a slut by an older, dominant man who will control her. If you're interested in something like this, we really should talk later."

As the meet and greet went on, M Suzanne had several other similar conversations with potential Daddies for kimmiann and she was very pleased with the attention her pet was getting. There weren't many other sissies onboard that she noticed and about half the couples seemed to be into D/s and BDSM.

kimmiann knew that the decision of who would use her this week belonged only to her Mistress as she continued to stand quietly beside Her, head down. Knowing that her opinion didn't matter and that she had no say whatsoever was very exciting for kimmiann as she imagined what she'd be doing this week.

The meet and greet was over but M Suzanne had information from several alpha men and they arranged to have dinner later with one of the couples they'd met. Mistress wasn't bi and wasn't interested in playing with other women and she was clear with the couples they spoke with. She hoped to find another couple in a FLR like theirs that they clicked with.

They went back and changed into swimsuits to check out the pool. Mommy Mistress was in a black suit with a black cover up and kimmiann was wearing a pink floral tankini. She was also ordered to wear a plug. Her cage was visible as was the plug, and she wasn't sure how she felt about this. M Suzanne told her this is what She wanted and there would be no further discussion.

When they got to the pool they saw quite a few people had already removed their suits and were in the pool or lounging in the nude. Mistress wasn't ready to remove her suit just yet, so she laid on a lounge chair and told kimmiann to apply sunscreen to her, making sure not to miss any spots. She loved how it made her feel when kimmiann served her like this, even more so out in public this way. It was so arousing. She told kimmiann to lay on the chair beside her.

An older man caught M Suzanne's eye and she took kimmiann over to talk with him. He said he was a bi, switch type and enjoyed topping sissy gurls. Mistress told kimmiann to turn around so he could inspect her and he liked what he saw. She told her pet to take off her swimsuit for their new friend. Mistress noticed his cock stiffen in his trunks and she suggested they go somewhere a little more private.

She told kimmiann to remain naked as they walked to a playroom. When they got there, Daddy removed his trunks showing off his impressive cock and Mistress told kimmiann to get on her knees. She asked Daddy if he liked his ass eaten. In response, he turned around and bent over. kimmiann was ordered to do what she does, like the whore that she is, and eat his hairy asshole. Daddy groaned as kimmiann licked and probed with her slutty tongue. Mommy Mistress told kimmiann to lick his balls and stroke his cock. A few minutes later, Daddy turned around and shoved his long, hard cock in her mouth.

kimmiann was a well trained mouth slut and Daddy was very aroused as she teased the head, then swirled her tongue around, gagging on the length of him. He grabbed her head and fucked her face going deeper and deeper with every thrust, grunting and moaning with pleasure. M Suzanne held kimmiann's head in place and told her to take it all.

"Be a good gurl for Mommy and our new friend, pet. Relax your throat and take his whole cock, baby gurl. Do it for Mommy. You're my little cocksucking pet and I want you to deep throat Daddy's cock."

She pushed her head on the cock as kimmiann choked and gagged but she took it all. Mistress was very wet and touching herself. Daddy gave one last grunt, pulled out and sprayed his load all over her pet's face. Mistress told kimmiann to lick his cock clean. She fed some of the cum from kimmiann's face to her from her finger, but left most of it on her face.

Daddy put his trunks back on and said he hoped to see my pet again and left. kimmiann felt used and objectified and she loved it. She knew this was who she was. M Suzanne ordered kimmiann to finger her to orgasm then told her to walk back out to the pool, face covered in cum, so everyone could see what a whore she was, barely 3 hours into their vacation.

As they walked back to the pool to get their things, kimmiann felt the sting of humiliation as she walked naked, cum drying on her face, mixed with streaks of mascara. It was obvious what she had just done and even though it was a kinky cruise, she still felt humiliated and embarrassed.

M Suzanne was enjoying this greatly. She wished kimmiann wore her collar and leash so she could lead her around the ship like this. Her slutty sissy pet on display showing everyone what a whore she really is. They picked up their things and went back to their cabin to rest and get ready for dinner.

After a quick nap and a shower, they dressed for dinner. It was a casual dinner and not a costume night. Mommy Mistress had on a black cocktail dress and black heels. She picked out kimmiann's outfit, a tight rainbow colored mini dress, matching hot pink lacy panties and bra, with white thigh hi hose and pink hi heels. She also set out her metal chastity cage and anal plug.

She did kimmiann's makeup more heavily for dinner, focusing on her eyes. She put on a long blonde wig and lastly, spritzed her with perfume. They met their dinner companions, Diane and Mark, the couple from the meet and greet, and headed to the main dining room.

Diane and Mark were swingers but not D/s and like most of the men, Mark was bi. Diane was too but she understood that Mistress wasn't playing with other women. This was Diane and Mark's 10th kink cruise, and they knew quite a few people. Mistress was glad they had met them early on. They introduced them to several other couples at their table and happily, another FLR couple. M Suzanne was looking forward to spending time with them.

Everyone got along well during dinner and afterward, they headed to a club for some music and dancing. They drank and danced and dirty danced and grinded on each other and a few of them decided they wanted to go to a playroom. There were only a few people there and the six of them headed to secluded spot in the corner and got comfortable in an extra large bed.

Mommy Mistress and kimmiann joined Diane and Mark and Sonya and Bill, the other FLR couple. Bill wasn't a sissy, but he was bi and he crossdressed on occasion, when he was told to. But it wasn't their main kink. He wasn't in chastity tonight.

Sonya began making out with Diane and Mark and M Suzanne told kimmiann to strip to her lacy bra and panties. She had talked with Sonya earlier and had permission to Domme Bill so she told him to strip naked, then remove her shoes and worship her feet. MIstress loved when kimmiann licked her feet and sucked her toes and it felt different having another sub do this.

She glanced over at kimmiann watching them and thought she saw a hint of envy or sadness. M Suzanne had a gleam of sadistic satisfaction in her eyes.

"kimmiann, you're not needed here, Mommy wants you to go kneel down on the floor and just quietly watch."

M Suzanne told Bill to remove her dress as she glanced over and noticed Mark was fucking Diane and Sonya was sitting on her face grinding her pussy on her, moaning in pleasure. M Suzanne told Bill to remove her panties and make her cum with his mouth. He was good with his mouth and his tongue and M Suzanne held his head to her wet slick pussy and rubbed her cunt on his face.

She was so close but she pushed him off and ordered him to lay down, hands at his side.

"I'm going to use your dick for my own pleasure now, subby. Lay still, don't move and don't cum. You're my fucktoy right now, just a dildo I'm using to cum. This is for me."

His submissive dick was hard and thick and Mistress rode it to an explosive orgasm. Bill was obedient and did not cum but after she was finished M Suzanne gave him a ruined orgasm and smiled.

"kimmiann, come over here and lick this dildo clean for Mommy. It's my pet's job to clean my toys once I'm done using them."

The playroom started filling up and one of the alpha men she had talked with earlier came toward them. He spoke to M Suzanne.

"Nice to see you again. Is your pet free tonight?"

"She's free at the moment and I want a Daddy to fuck her right here, right now. Are you the one?"

She glanced over at kimmiann, who was back in her submissive pose, and smiled.

"Yes Ma'am, I'd love to fuck that little slut right now. I want her face down, ass up for me."

M Suzanne grinned.

"Do as he says kimmiann. Take off your panties, take out your plug, then face down ass up. You're Mommy's little slut tonight."

Daddy removed his pants and kimmiann got into position beside Mommy on the bed. She had some lube in her bag and Daddy warmed up kimmiann with the lube and his fingers. After a few minutes of warm up, he stroked his cock a couple times and entered her pet.

Just a little at first, then he slowly went deeper and deeper. kimmiann gasped and Mommy told her to relax and open up.

"You're my slut, kimmiann, this is what you're for. Your purpose is for other people's pleasure and my new friend wants to fuck you. He's going to pound your tight little hole because I say so, do you understand?"

"Yes Mistress Suzanne."

"You're anyone's toy I tell you to be, you don't get to choose. You are mine and I'll use you however I want."

"Yes Mistress."

Daddy was going in and out now, slowly but he was in balls deep. kimmiann was taking it well and Daddy started to find his rhythm. He started going a little faster and kimmiann was moaning. Her clitty was dripping from its cage and Mommy wiped up the precum and put it to kimmiann's lips.

"Look at you, look how excited you are being violated and penetrated like this in front of all these people. Such a fucking whore. Such a faggot."

Daddy was pumping faster now. kimmiann was dripping harder and moaning louder. Her clitty was so swollen in the cage. The scene and kimmiann's moans were making Mistress' pussy drip just like her pet's. She heard Daddy's breath change and he was going to cum.

She started rubbing her pussy and came in just a few seconds. She heard Daddy grunt and cum inside her pet. He pulled out and kimmiann got her first creampie. Mistress intended to make her eat another man's creampie from her divine Goddess pussy later this week and this made her look forward to that adventure even more.

ATM was a hard limit so Mistress gave Daddy a towel to clean up with. She took a picture of kimmiann face down, ass up, cum oozing from her hole. She uploaded the picture to Fet and couldn't wait to use it on Grindr when they got home.

By now it was getting late and it has been a really long day and M Suzanne said it was time to go back to their cabin. They told everyone goodbye and agreed to meet up for breakfast in the morning. Mommy told kimmiann to get up and put her plug back in, so she could hold her Daddy's cum inside like a true dirty whore.

kimmiann was definitely a slut at heart and Mistress was so excited to see her being her authentic self. It was only night one, they couldn't wait to experience all the adventures they knew they were going to have on this trip.

M_Suzanne
M_Suzanne
27 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
AnonymousAnonymous23 days ago

VERY GOOD WAITING FOR PART 2

WoldermanWolderman2 months ago

What a gorgeously slutty story

Share this Story

READ MORE OF THIS SERIES

Similar Stories

A Sissy's First Wedding Anniversary A Sissy Girl getting ready for her Black Husband.in Transgender & Crossdressers
Masculinity Lost How a straight guy was forced to become a sissy.in Transgender & Crossdressers
A Sudden Change A sissy real life tale... the coming out process.in Transgender & Crossdressers
Damon's Growing Family Damon and family love black cock.in Transgender & Crossdressers
A Cuck Returns to the Church Ch. 01 A cuck is born; then, a chance meeting with an old friend.in Fetish
More Stories