Cruise Doubledate With My Sister

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Şub 20, 2023 // By:analsex // No Comment

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This is a long, slow story so a quick summary – Thomas and Caitlin are brother and sister and they go on a cruise with their significant others, Rebecca and Jacob. The first part of the story is introducing those four characters and their relationships. Rebecca and Jacob exit stage right together, leaving Thomas and Caitlin crushed. They console each other, sexual tension starts to build and you can guess the rest.


A Saturday in April, Miami


My sister waved to me then made her way through the crowded atrium of the cruise ship to where my girlfriend and I had been waiting for her and her boyfriend. I hugged her.

“This is Rebecca,” I said proudly.

Rebecca and Caitlin hugged.

“Thomas had sent me pictures of you. You’re even prettier in person.”

Rebecca blushed. She was pretty, easily the prettiest girl I had ever dated, with wholesome cheerleader/girl next door looks – blond hair down to her waist, deep blue eyes, full lips and a radiant smile.

Caitlin was the first member of my family to meet Rebecca. I felt the urge to put my arm around Rebecca’s shoulders to show Caitlin how proud I was to have her as my girlfriend, but Rebecca was uncomfortable with any public displays of affection beyond holding hands.

“So you two work together?” Caitlin asked.

“We’re on the same floor,” I said. “But we have never done any work together.”

“How long have you been dating?”

Rebecca and I looked at each other.

“Well, we’ve never dated,” said Rebecca. “We were friends for a long time then went to boyfriend-girlfriend.”

“How long have you been boyfriend-girlfriend?”

Rebecca and I looked at each other again.

“What, a month now?” Rebecca said with a laugh. She had a bubbly, contagious laugh.

“You called me your boyfriend for the first time a couple of days after I called Caitlin about the cruise, so less than a month.”

Caitlin had a confused look on her face. Rebecca laughed lightly.

“We haven’t had a straightforward romance,” Rebecca said. “When we met, neither of us wanted to date the other. I was looking for a devout Christian…”

“And I didn’t want to date someone so short.” As I’m 6’3″ and Rebecca is 5’1″, I tower over her and we frequently draw stares.

“We met when Thomas was chasing the other new Marketing hires.”

“The single guys in the company look forward to when the new college hires show up in Marketing. They seem to hire only pretty women.”

“People paired up quickly and Thomas missed out. I wasn’t interested in any of the guys who flirted with me. Thomas saw that I was lonely. I’m from a small town in Texas near Amarillo and didn’t know a soul in Boston. Thomas offered to do some things with me as friends. So we did things as friends, and did some more things, and here we are!” Rebecca finished with a big smile.

“Where’s your boyfriend?” I asked.

“He misplaced his passport and was searching for it. I know he has it. He should be here any…there he is!” She waved and a guy moved in our direction. He was very good looking, something like a young Tom Cruise with a dark, thick mustache. He looked a little taller than Caitlin, who’s 5’8″.

“Oh my God!” Rebecca cried as he approached. “Jacob!”


They gave each other a big hug.

“Well, you two obviously know each other,” said Caitlin.

“This is incredible!” said Rebecca to Jacob. “I thought I’d never see you again!”

They hugged again, then Jacob hugged Caitlin while Rebecca moved to my side and took my hand.

“We dated our junior and senior years at OU”, said Rebecca. Rebecca had gone to the University of Oklahoma. “We split when we graduated and we haven’t kept in touch. This is amazing!”

Rebecca had mentioned Jacob a few times, but I never would have guessed her boyfriend at OU was Caitlin’s boyfriend in Wichita.

“I told you God would bring us back together,” said Jacob.

“Jacob, this is my brother Thomas,” said Caitlin. She sounded a little pissed.

Jacob and I shook hands.

“We might as well explore the ship,” said Caitlin. “Our luggage won’t be in our cabins for a while and just before we depart, we’ll have to muster on deck to make up the lifeboat teams and get safety instructions.”

As we headed off, Rebecca asked Caitlin, “Have you been on a cruise before?”

“A year ago during spring break with three of my girlfriends from college. We all came down with norovirus.”


“Food poisoning. Nasty as hell. Most of the people on our cruise came down with it. My friends and I were sick as dogs for days. We had spent lots of money on shore excursions but couldn’t go on them because we were constantly running to the bathroom.”

“Did the cruise line refund your money?”

“No. They gave us a voucher for another cruise. My friends didn’t want to go so I bought their vouchers. Those vouchers are what we are using for this cruise.”

Caitlin had left istanbul escort out that it had been her idea to go on the cruise and that her friends had been furious when they got a voucher instead of a refund. To save the friendships, Caitlin had bought their vouchers and had borrowed money from me to do it.

The cruise ship was huge with so much to see. Rebecca was like a little kid on Christmas, rushing ahead of the rest of us to see the next new thing then laughing in delight. We were looking over the shops when a voice on a loud speaker announced it was time to go to our muster stations for the passenger safety drill. After the safety drill, we went to our adjoining cabins to change into our swimsuits.

Once in the cabin, Rebecca asked me with a saucy smile, “Shall I give you a little show?”

“Please do!”

I started singing the stripper song. Rebecca kicked off her shoes then turned her back to me and made a circle with her cute little ass. She turned back to face me, reached behind her to unsnap her bra, then reached through her shirt sleeves to grab it. She slowly pulled it out of her shirt and tossed it aside. I had my shorts and underwear off and stroked my cock as she stripped for me. She slowly pulled up her shirt, revealing her toned stomach. When the bottom of her shirt reached the bottom of her tits, she spun around. As she shook her ass, she slowly pulled her shirt above her shoulders and then over her head. In high school, she had played a lot of sports and water skied. Her back still had good muscle definition.

Rebecca dropped the shirt down so that it was covering her tits. She twisted to look back at me so that I could see her shirt-covered tits, then spun around to face me. I kept singing the same few bars over and over again as I stroked in rhythm. She pulled the shirt back and forth in front of her tits, gradually dropped it down so that I could see them, then tossed the shirt aside. Her body was thin with her waist just a little narrower than her chest and hips, but her tits were large in proportion to the rest of her. They were a fine size for me to fondle and suck.

The strip tease wasn’t long enough or stimulating enough to make me cum. It was long enough and stimulating enough that stroking my cock gave me a lot of pleasure.

Rebecca spun around again and put her hands on the counter that a TV was sitting on. She did some big circles with her ass in time to the song. She reached back and slowly slid her shorts down her legs, revealing bright blue cotton French-cut panties. After she had kicked her shorts aside, she looked over her shoulder at me. “Like what you see so far?”

“I love it.”

She’s so damn good looking. I considered myself above-average looking with light brown hair in a business cut, brown eyes, broad chest and a narrow waist, but I was definitely “dating up.”

She grabbed the counter again and did some more big circles with her ass. She reached back and slowly slid her panties down, revealing her firm, cute ass. I kept up the song, even though my voice was getting tired. She made the descent of her panties last twice as long as her shorts, then she kicked them aside as well. The only thing she was wearing now was a chain around her neck with a cross on it. All but her arms, her legs and the top of her chest were very white. She stood upright and twisted her upper body to look back at me. She looked straight and then twisted a little more, exposing more of her body to me. She made bigger and bigger twists until finally I could see all of her naked front.

She gave me a big smile, then bounded over and jumped into my arms. She was so light that I easily held her off the ground as we kissed.

“That was wonderful.” I wanted to tell her that I loved her, but when I had told her that a few weeks ago, she had gotten very defensive and had told me that though she really liked me, she didn’t love me. “I wish we could do more.”

“They’re probably wondering what’s taking us so long as it is. We have the whole cruise.”

That’s the way it was with Rebecca – she would do what she was willing to do and no more. Asking for more just made her angry.

We put on our swimsuits. Rebecca’s was a conservative one-piece suit in a blue color which almost matched her eyes. Once we had our swimsuits on, we exited the cabin to find Jacob and Caitlin waiting for us.

“Still wearing one-piece suits, I see,” said Jacob.

“My parents had me wear one-piece suits growing up,” Rebecca explained to Caitlin, “and that’s what I’m comfortable wearing now.”

When I saw Caitlin in her orange bikini, it took my breath away. I had forgotten how great of a body she had. She was built like an Amazon with broad shoulders and thick legs. She had been a terror at field hockey in high school, sending other girls flying without noticing the contact. Her tits filled out the bikini top quite nicely. She obviously worked out regularly as her body was very muscular. As we walked to the pool, I checked out her firm ass which looked şişli escort like it was meant to be grabbed. I was envious of Jacob for a moment.

The pool area was a big party with lots of people our age and we hung out there for a long time. I wasn’t comfortable around so many new people and struggled to make small talk. Rebecca loved making so many new friends and had the gift of making strangers quickly comfortable. Rebecca had been in a bad mood all week and I was happy to see her enjoying herself so much. Jacob enjoyed meeting new people much like Rebecca. Caitlin was somewhere between Rebecca and me.

I got bored listening to Rebecca, Jacob and occasionally Caitlin talk with people who, frankly, I wasn’t interested in. I had made a lot of friends in Boston by just hanging out with Rebecca, but I didn’t see the point of getting to know people that we wouldn’t be spending much time with and we wouldn’t be seeing again once the cruise was over. I zoned in and out of the conversations. When I zoned out, I checked out the women in the pool and decided that Rebecca and Caitlin were the best looking. Caitlin had gorgeous Italian looks – dark brown hair which came down to below her shoulders, dark eyebrows, almond-shaped dark brown eyes and a diamond-shape face. She had fuller lips than Rebecca, but not as nice of a smile. We weren’t Italian, but the family joke was that the milkman had been. Rebecca occasionally caught me checking out the other women and when she did, she’d roll her eyes then give me a tight little smile.

Around nine, Rebecca could tell that I was hitting my boredom limit and asked, “Would you like to go for a walk?” One of the things that had brought us together was our mutual love of walks.

“I’d like to stretch my legs,” said Caitlin. “How ’bout I go with Thomas?”

“What do you think, Thomas?” asked Rebecca.

“Rebecca, you stay here and I’ll walk with Caitlin.” She was having such a good time that I didn’t want her to stop just because I was bored. Also, I wanted to have some time alone with Caitlin.

Once we were away from Rebecca and Jacob, I asked Caitlin, “What do you think of Rebecca?”

“I like her. I like her a lot. Are you guys serious?”

“Yes. I think she’s the one. I expect we’ll be engaged within a year.”

“Is she from a fundamentalist family?”


Caitlin and I had grown up in a small town outside of Wichita. In our town, most of the families went to fundamentalist churches. Our family was Methodist. The kids who didn’t go to a fundamentalist church tended to stay away from the kids who did. The fundamentalist kids came across to Caitlin and me as zealots whose faith kept them feeling guilty. The fundamentalist kids had turned me off of religion and I had stopped going to church when I had started high school.

“I thought you wouldn’t date a fundamentalist kid?”

“Rebecca and I haven’t really dated.”

“That was weird. It threw up a lot of red flags for me.”

I raised my hands up in a what-can-I-say gesture. “Neither of us took the other seriously. We had a lot in common, both being from small towns in the middle of the country. We became friends, then friends with some benefits, then I was in love. Are you serious with Jacob?”

“No. When we first went out, he totally wowed me. He’s great looking, funny and always has a story to tell. It took me a while to notice his flaws but once I did, I cooled on him considerably.”

“What does he do?”

“He’s an assistant manager for a truck stop on 35 halfway between Wichita and the Oklahoma border.”

Big whoop-de-do

I had gone to the University of Kansas and had graduated almost two years ago with a major in Economics and a minor in Math. After graduation, I had gotten a job with a big corporation in Boston. I’m 21 months older than Caitlin but because of when we were born, she had been one grade behind me in school. Caitlin had wanted to go to KU, but hadn’t had the grades and instead had gone to Wichita State University. She had graduated last May with a degree in General Business and had gotten a job as a bank officer in Wichita.

As we walked, almost every guy turned to check Caitlin out. I could tell they liked what they saw.

“What are these big flaws?” I asked.

“He’s lazy and self-centered. He wants his way all the time. He’s always suggesting things to do and if I don’t want to do what he suggests, he gets bent out of shape. He’s very sensitive about his height and gets upset if I wear a shoe which makes me taller than him. I’m getting tired of all the drama. We fight regularly. I wouldn’t be surprised if we break up soon.”

“If he’s that much of a loser, why are you doing a cruise with him?”

“To get the best possible travel deal, I had to make the reservations two months in advance. Two months ago, I was still pretty high on him. But if I had known then what I know now about Jacob, I probably still would have invited him. When I made the reservations, I had four vouchers, remember? I was mecidiyeköy escort sick of getting nothing out of all that spent money. I wanted to shut up my three girlfriends who go on and on about how rotten cruises are. I wanted to go on this cruise so bad that I told Jacob that all he would have to pay was the airfare. He’s struggling financially like me. If I had waited to go on a cruise until I was in a strong relationship that I knew would last, I might have waited for years.” Caitlin as usual had a practical reason for what she did. “Oh, and thanks again for buying the other two vouchers.”

“No problem. I’m glad I did. Going on this cruise with Rebecca is a big step forward in our relationship. I wish I could have bought them back when you made your reservation, but Rebecca and I were just friends then. It was only a month ago that I felt she would be comfortable taking a cruise with me. If it makes you feel any better, Rebecca also only paid for her airfare.” I knew she would feel guilty about taking a vacation with me and if she had had to pay her full way, I had thought she would have said no.

“Don’t worry about Jacob and me. We should be able to get along well enough to do the four things I want to do on this cruise – drink, dance, fuck and have fun on the shore excursions. If I do those four things, then I’ll consider this cruise a success. And if I have a successful cruise, I can tell my girlfriends to shut the fuck up.”

Caitlin was having a tough stretch. She was struggling financially. Her job wasn’t satisfying. Now her relationship with Jacob was close to finished.

“It’s crazy that Rebecca and Jacob used to date,” said Caitlin. “What are the chances of that happening?”

“One hundred percent.”


“Once something has happened, the chance of it happening is one hundred percent.”

“Don’t go all nerdtastic on me,” she said playfully.

“Improbable things happen every day. People make too big of a deal about them when they do happen.” It boggled my mind that people would buy books on “hot” lottery numbers. “Probability was my favorite subject in college. I think they should teach it to everyone in high school as it has such great day-to-day applications. Once you understand probability, you don’t do stupid things like buy scratch-off tickets.”

We walked along quietly for a while. There wasn’t much to see – empty ocean and a few stars.

Caitlin and I hadn’t been close growing up. Once she had gotten to seventh grade, she had gotten her curves and had gone boy crazy. She had then spent as much time as possible with her boyfriend du jour. I had been a tall, scrawny, socially-awkward nerd. The only time we had spent time together was on summer vacations and we had gotten along decently on those. After her freshman year at WSU, she had changed. She had gotten a 2.2 GPA for the year and had realized that if she kept up the partying and the boy-chasing then she wasn’t going to graduate. We had enrolled in three general requirements classes together at the local community college. I had helped her with her homework and had wound up teaching her lots of basic academic skills. We had done a lot of other things together that summer. We’ve been close ever since.

I was tired of the quiet. “What are my flaws?” I asked.

“You’re too passive and avoid conflicts.” Ouch! “Does Rebecca avoid conflicts too?”

“She’s worse than me. It has been a big problem for her at work.”

“I’d guess when the two of you have a serious issue, neither of you will address it.” Double ouch! “Are you two thinking of living together?”

“She’s said no whenever I’ve asked her to. Normally, I’ll ask once about something and accept whatever she says, but I’ve asked her several times about living together. Rent is so expensive in Boston. Our leases are due to be renewed on the first. I don’t want us to renew our leases then a few months later have to pay through the nose to get out of one of them.”

We had finished our lap around the deck. “Let’s get back to the pool,” I said. “We’ll grab Rebecca and Jacob and go dancing.”

“Sounds great.”

* * * *

I was having a great time dancing with Rebecca. It was the first time we had ever danced together. I love to dance and I wanted to dance for hours. However, I could tell Rebecca wasn’t have a good time. After a half dozen songs, she was ready to leave the dance floor. Jacob and Caitlin followed us out.

“I don’t like it in there,” said Rebecca.

I sighed.

“I don’t!” She looked angrily at me. “Let’s do something else.”

“How about blackjack?” Jacob suggested.

“Anything would be better than this,” said Rebecca.

“Let’s not and say we did,” I said. Rebecca gave me a dirty look. “Gambling is stupid. On average, you lose money with every bet.”

“If you’re lucky, you can win money,” said Jacob. He clearly felt lucky.

I looked at Caitlin.

“We could gamble for a while then come back later.”

Three against one, I gave up. We went down to the casino and found a blackjack table with a five dollar minimum bet. Jacob charged $25 worth of chips to his cabin and bet five dollars. The rest of us watched.

Jacob was dealt an eight and a two. The dealer turned over a six.

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