The Cruise of a Lifetime Pt. 01

Story Info
Little sister convinces big brother to take her along.
5k words
4.36
43.6k
99
6
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

"Well, this just sucks!" I said, as I plopped down on the chase lounge next to my sister.

"What sucks?" She looked up from her book at me over the top of her glasses.

"The cruise I had booked! Genie and I were supposed to leave in 3 days, but that sure as hell isn't happening now, and it's too late to cancel the tickets and get my money back." Genie was my girlfriend. Well, she was my ex-girlfriend. We had just had a very public and very final breakup.

"Oh man, I forgot about your cruise. I'm sorry big brother. Can't you just go by yourself? Maybe it would do you some good to just get away by yourself for a little fun in the sun."

"Nah, it's a "Couples only", themed cruise. No singles or kids allowed."

"So, take someone else. Surely there's a girl you know that would love to spend a week cruising the Caribbean. What about Connie?"

"Connie has a new boyfriend. I've already gone through all the possibilities. All my exes are either in relationships, or I wouldn't want to spend a week on a boat with them. It's no biggy, I'll just cancel."

"Hmmm, I'd say, give me the tickets, but I'm in no better shape than you are." My just-turned 20-year-old sister was home from college for the summer and she had had an equally final ending to her first college romance just prior to arriving. She had caught her boyfriend sleeping around on her and it had put her off dating for a bit. She had always been the shy type and never really had a boyfriend in high school. To tell the truth, she had been downright mousey and introverted, hiding her flat chest and skinny frame behind her glasses and a stack of books. She'd pretty much been a loner through high school, and I had been happy when I heard that she had finally broken out of her shell. But that means she also didn't have any prospects around the hometown either. "Mark apparently has a thing for big boobs." she laughed.

"Well, he's an idiot. You're a great catch. Just because you aren't top heavy, doesn't give him the right to cheat on you. Besides, I think you're finally getting some cleavage...unless that's a push-up swim top."

"Colin! Stop it! You know I'm self-conscious about that!" she blushed and covered her A-going-on- b cups with her book. "Do you really think they're getting bigger? My bras are a bit tighter..." she mused looking down at them.

My shy sister had always been pretty, but most guys didn't notice it because she never wore tight clothes or much makeup. She has fantastic green eyes and a perfect cupid's bow mouth. She also has the best smile I've ever seen and with her slim 5-foot 8-inch frame, she could pass for a willowy runway model...except for her adolescent chest.

"Your ass is getting bigger too."

"Asshole!" she shouted as she threw her paperback at me. I was only teasing her, but in truth, she really was filling out her string bikini damn well when I looked at her with a man's eye. Her long dark brown hair was sexy and disheveled, wisps sticking to her face where she was sweating in the midday sun.

"Hey!" she exclaimed. For a second I guiltily thought she was pissed that I had been staring at her. But then she continued, "Why don't you take me?"

"What? Take you where?"

"On the cruise, you dolt! I'd kill to go on a cruise. There's no sense in wasting the trip. Let's you and I go and have some fun! It's not like I have anything to do this summer except stick around here and be bored. And the last thing I want to listen to is you mope around and sigh heavily for the next two months."

For a second, I couldn't think of anything to say. I mean, I hadn't thought of taking anyone else, because it had originally been a date, but looking at her lying there all excited and kinda hot, I hesitated. "But there's only one room and it's little. And it's a single berth..."

"Oh pish! We've shared a room and a bed before! "

"Not since we were kids..."

Waving her hand dismissively at my objections, "Oh, I already know you snore. Besides, it's paid for! Please? "

Laughing at her sad face I went on, "But remember, it's a couples only trip."

"So what? No one has to know we're brother and sister. It's not like you're trying to smuggle a couple of kids on board! We'll lay out and go to dinner and shopping and sightseeing....! Hey! Maybe I'll get lucky and meet a handsome rich plantation owner that will whisk me away from all of this", she said gesturing around the back yard."

"Yeah, but..."

"Please, please, please! I've never been anywhere! Come on!"

Looking at how happy she obviously was, my resolve melted. What the hell? It wasn't as much fun as taking a girl with me for non-stop sex, but it did beat sitting around with our parents for the rest of the month. "Okay, okay, okay, why not? Let's go!"

"Really!? You mean it? Oh my God, you're the best! This is going to be awesome!" She leaped on top of me and smothered my face with sisterly kisses and I tried not to notice her firm hot body on top of me. What the hell was going on with me? I'd never even thought of my 2-year younger sister as a real female, let alone as a sexual creature, but apparently, my cock had started to as I felt myself get instantly hard.

Pulling back and giving me an odd look, Jenni giggled. "We've always gotten along well and I'm sure mom and dad will be happy. They're always telling us to do more together." Bouncing up and grabbing her towel, she ran into the house. "I'm going to figure out what to take!" Holy shit, her ass DID look good as it rippled under her high cut bikini bottom. I wondered how frustrating this was going to be...

...

I should have taken it as a sign of how much of a fiasco it was to just get to the ship. One of our connecting flights had been delayed due to engine trouble and we had just barely made it to the dock in time as the last passengers were boarding. The worst thing was that our baggage hadn't made it to the new flight, and we almost didn't get out of the airport on time. We had finally been assured that our luggage would arrive at the airport later tonight and that the cruise line would pick it up just before they weighed anchor... or not. It would be close. All we had were our backpacks, our passports, and the rumpled clothes on our backs. I had no clue what we were going to do if our bags didn't catch up.

Looking at our papers, the purser said, "Ahhhh, Mr. and Mrs. Corland! We were afraid that you weren't going to make it. All the other passengers are on board. You'll have to hurry to make the safety briefing. The cruise-line office called about your luggage and wanted to let you know that it didn't look like it would make it by the time we left port, but they've arranged to have it forwarded on to meet you at our first port of call tomorrow."

I was about to open my mouth to correct him about our marital status, when Jenni piped up, "Oh thank you so much! What a way to start our Honeymoon! But at least we made it this far. We can always pick up new things till our bags catch up." Her enthusiasm hadn't been dampened in the least. She was like a kid at Disneyland even after the rough day.

Both the purser and I gave her an odd look. "Err, you two are newlyweds? We had no Idea. Well welcome aboard. Here's your berthing assignment and a map. You'd better hurry up to the Lido deck to catch the safety briefing." Jenni flashed him a bright smile and hugged my arm. "Come on honey, let's hurry!" and off we went.

"What was that all about?" I laughed as we hurried down the corridor.

"I don't know." She replied, "It just came out. So what? We're supposed to be a couple and I thought it would be fun to pretend that we were on a honeymoon. No biggy."

"Yeah, but what you don't understand is..." the rest of my explanation was cut off when we rounded the corner and merged with a large group of raucous couples heading our way.

Later, after briefings and a quick tour of the ship, we ate a light dinner in one of the many salons. I noticed that Jenni yawned more and more often and looked ready to go to sleep right there at the table. "Hey, let's hit the hay. It's been a long and eventful day and we'll have plenty of time tomorrow to have fun." With a sleepy nod, we made our way back to our small outboard cabin.

"First dibs on the shower!" Jenni chirped when we walked through the door. She stuck her tongue out at me and smiled as she headed into the bathroom. Soon, I could hear the water running through the door. I picked up the room phone and dialed the service to check on our luggage. The staff was busy getting underway, so after waiting while several departments looked in vain for our belongings, I finally just told them to not worry about it and prepared to go without fresh clothes for another day. Housekeeping offered to send someone to our room to collect anything that we would like to have laundered and returned in the morning. I happily agreed.

I had just shrugged out of my travel worn clothes and into a towel when there was a knock at the door. "Laundry service." They called out. "One second!" I yelled back. I hurriedly grabbed my things and without thinking, opened the door to the bathroom. Spying Jenni's clothes lying in a neat pile on the floor, I scooped them up and happened to glance at the shower. Through the semi-transparent glass, I could see a vague outline of Jenni soaping up under the spray while singing softly to herself. For a moment, I couldn't look away, it was so sexy. Then, coming to my senses, I looked away guiltily and ducked back out to give our things to the girl at the door who slipped every neatly into a bag and assured me that they would be returned clean and fresh in the morning. Thanking her, I closed the door and thought about Jenni.

Was it because I was tired? Did she seem...different? We had shared a bathroom as kids, and I had seen her through the shower curtain on more than one occasion. Maybe it was her talk of having fun where no one knew us, or the fact that I was on an adult cruise with a beautiful woman. Whatever it was, I needed to shrug it off. She was after all my baby sister, and I had never had any sexual thoughts about her.

Through the door I heard the shower turn off and a moment later, "Hey! Where are my clothes? Did you take my stuff, you ass?"

"Yes, I took your stuff! I sent everything out to be cleaned, so we won't have to wear dirty clothes into port tomorrow. You're welcome!"

There was a long pause, "But what am I supposed to wear to bed tonight?"

I hadn't thought of that.

"Uhhh, okay, maybe I didn't think this through all the way. Look, just trade places with me and you can climb into bed while I'm in the shower. It's not like we haven't seen each other naked you know."

No answer from Jenni and I was about to pound on the door, being tired and wanting a shower and bed, when she emerged wrapped in a towel, hair still damp. She looked like a goddess with the towel barely covering her small breasts and ending just below her groin. I would have bet that it didn't quite cover her ass cheeks. Blushing and not looking at me, she stepped around me and towards the bed.

"There's plenty of hot water. It feels nice." I tore my eyes away from her as she walked by, the towel didn't cover her entire ass.

...

Twenty minutes later, clean and feeling human again, I stepped back into the bedroom. All the lights were out except the one on my nightstand. I could see Jenni's form under the covers on one side of the bed, her dark hair fanned out over the pillow. She made no sound. Probably fast asleep.

I pulled back the covers on my side and turned out the light. Taking a deep breath, I dropped the towel onto a chair and slid into bed. Why was I so nervous? It's not like we were sitting around the room naked staring at each other. She's my sister, I told myself as I settled into the pillow and closed my eyes. Just as I was drifting off, I heard Jenni say, "Colin? Thank you for all of this. I'm glad you are here to take care of me."

"That's what big brothers are for."

...

The next morning, a persistent knock woke me from a dead sleep. Throwing back the covers I quickly crossed the room. Being used to sleeping naked, I didn't even think about it. I hid behind the door as I cracked it and managed to open one sleepy jet lagged eye.

"Good morning, sir! Here are your things. We tried to call, but no one answered the phone. If you are going into town, you'd better hurry, the last water taxi for Playa leaves from the departure area in 20 minutes."

"Err, okay, thanks." I managed to mumble and shut the door. I heard a rustling behind me, and I turned and said, "Hey, our clothes are back." I saw Jenni sitting up in bed, the sheets clutched to her breasts and noticed that she was staring rather south of my eyes. Following her gaze, I looked down to see my cock swaying between my thighs in full view. Hastily, I covered myself up with our folded clothes and turned my back to her, looking for the towel. Now where had I dropped the damn thing? I heard the bathroom door shut and the sounds of Jenni taking care of her morning routine.

Just like her locking herself in the bathroom first as I noticed that I had to pee so bad it hurt. Hearing the shower go on, I panicked and knocked on the door. "Hey, wait. I need to pee!"

"Hold it! I'm already in the shower."

Dancing around, nudity forgotten, "I can't! Hurry up!"

"Christ! Just come in and go." The door lock snicked open, and I barged in rushing to the toilet. Looking at the clock on the wall, I exclaimed, "Holy shit! Hurry up. We've only got about fifteen minutes to get to the boat!"

"What!? Why did you let me sleep in so late?"

"Me? It's not my fault!" Thinking about nothing now but missing our first day in port, I opened the shower door and stepped in next to Jenni.

"Hey, what the fuck! Get out!" she screamed at me, trying to cover herself up with her hands while soap dripped into her eyes.

"Oh, lighten up, I've seen a naked woman before."

"Yeah, but not me! I'm your sister!" she shot back.

"Take it easy. We used to bathe together."

"Yeah, when we were kids!"

"Jesus don't look if it's gonna kill you, but I'm not missing the boat. Now hand me the soap."

Turning to the wall, Jenni angrily continued to rinse the soap off and the shampoo out of her hair. "You're gonna pay for this!" As I quickly lathered up, I couldn't help but sneak glances at her naked back and butt. She really did have a great ass and such long legs. Her back rippled with lean muscle as she rinsed her long hair, and I could just see a slice of enticing side boob. As she reached down to wash her legs off, I caught a glimpse of one rock hard nipple.

Quickly finishing, I stepped out of the stall and grabbed a towel, moving back into the state room to dry off. I heard Jenni follow me quickly and do the same. I tossed her clothes over my shoulder and we both quickly got dressed without any further threats.

"Dammit! Where are my panties?"

"What?!" is asked.

"Panties? Underwear for women? Where are they?"

Looking around the bed and floor, I failed to find any. I was already in my shorts, jeans, and t-shirt, holding my socks in my hand. "I dunno." I smirked. "Guess someone in the laundry room wanted a trophy."

"Very funny! What am I supposed to do now?" she exclaimed. She had donned the same short summery sundress that she had worn yesterday, though now it seemed a whole lot shorter knowing that she was commando underneath.

"Go without! Come on, either hurry up or I'm leaving you behind", as I reached for the door.

Hesitating only for a second with a hand on her hip, she finally rolled her eyes, grabbed her sandals, and headed out into the corridor, twisting her hair into a ponytail as she went.

For some reason, I couldn't help but have a massive smile on my face as I followed her.

***

We arrived at the boat just as they were closing the gate. Rushing on and finding a single seat towards the bow, Jenni pushed me down and then plopped in my lap. Innocent enough for a sister to do with her brother but made erotic as hell by the knowledge that she had no panties on. Even though we were separated by two layers of cloth, I still imagined that I could feel the raw heat from her young smooth pussy on my leg and I struggled to keep my increasingly stiff cock away from her as much as possible.

Her mood seemed to be back to its bright and cheerful exuberance again and I reflected on the change that had come over my quiet shy little sister. Travel was certainly good for her, or maybe she had blossomed in more than just beauty in the past year.

We spent a wonderful day in town, sightseeing, shopping, and enjoying a nice lunch in a quaint little dinner just off of the tourist path. Jenni was happy and playful, twirling here and there in her short sundress. At one point I teased her about being panty less and suggested we find her some before she got arrested for public nudity caused by a stray gust of wind. In return she shrugged, briefly flipped the back of her skirt up, mooning me with her bare round bottom before laughing and grabbing my hand to continue down the street. I caught myself almost wishing that we were a couple. What guy wouldn't want to be attached to a young, beautiful woman. And that was how I was coming to look at Jenni, not as a sister, but a sexy woman.

Returning to the ship in the late afternoon, we were pleasantly surprised to find our missing luggage waiting for us on our freshly made bed. Jenni wasted no time in opening her suitcase and putting her clothes away. I happened to be looking her way when she turned towards the wall and casually grabbed the hem of her dress, pulling it up and off her naked body. I was stunned but figured that she was getting used to being brother and sister that shared a room again. She deftly slipped into a pair of sheer black lace thong panties and a matching bra.

As she suddenly turned around, she caught me staring at her and she stopped. "What? Too fancy?" as she looked down at her black undergarments.

"No" I replied with difficulty, "I just didn't expect to see you in something like...that."

With a rueful grin she shot back, "Why? Surely you don't think I'm still a little girl, like mom does. She was frowning when she saw them too."

"No, no I don't think you're a girl. I mean, a little girl. I'm just used to seeing you run around in boy shorts and a sports bra. That's all. You look great. That is, they look nice on you...err, never mind." She stood for a moment, with one hand on her hip staring at me with an unreadable expression on her face.

"Anyway," I said, "let's get around and go watch the sunset from the deck." I quickly turned away and stripped down to my boxers, thinking, I can't let her see me flustered. Just barely hiding my erection, I managed to get into shorts and a t-shirt before turning around to find her slipping into another silky short dress. "Ok," she said, let's go."

The sunset was spectacular and as the air grew a bit chilly, Jenni snuggled under one of my arms at my side and smiled up at me. "My God," I thought, "she is gorgeous!" as I leaned down to give her a hug and a brotherly kiss on the cheek. Jenni hugged me tighter and grinned bigger. It occurred to me that we looked like a regular young couple. In fact, that is exactly what Jenni had suggested we pretend to be. Before I chickened out, I bent down and gave my beautiful sister a quick kiss on the lips. Her eyes opened a bit wider in shock, but she didn't pull away. After a second, I did and said, "Let's go eat. I'm starved."

Colin and Jenni were just turning to search out dinner when they heard an announcement come over the loudspeakers. It seemed that there was to be a general meeting in the ballroom that all passengers were encouraged to attend. The short briefing would go over some of the weeks planned events and discuss various "rules" for cruise.

12