Family Trip to Jamaica - Cover

Family Trip to Jamaica

Copyright© 2024 by Robdcruz

Chapter 2

Incest Sex Story: Chapter 2 - A mix up leads to a revealing trip for a family to a Jamaican resort. Several chapters with a slow initial build

Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Teenagers   Consensual   Reluctant   Heterosexual   Fiction   Sharing   Incest   Mother   Son   Brother   Sister   Father   Daughter   Group Sex   Exhibitionism   Oral Sex   Voyeurism   Nudism  

We followed Amelia to our room, and with each nude guest we saw I could see my dad turning bright red. He seemed to be the only one, as mom was chatting energetically with Amelia about the amenities and activities, and Lily was meeting each guest with a smile.

“If I didn’t know any better, I’d guess you were excited about this little mix up,” I whispered to her.

“As if you aren’t. I saw you sporting a half chub staring at that guy and girl in the lobby. What do you say, should be find them so you can finally fuck?” She was teasing about my virginity again but this time it felt different. She wasn’t angry ... it was more playful. Even flirty. I decided to play right along.

“Let’s do that,” I joked back. “And you can come along since you couldn’t take your eyes off that huge dick. You think you can take that whole thing?” I was internally cringing that I was going too far. But as I said it, a look of hope or eagerness quickly passed over Lily’s face.

“Did you hear that kids,” my mom shouted back to us,”They have plenty to do. There’s even an art class you can take where you can do some live figure drawing. Maybe that will be a nice ice breaker before we all brave the beach. So many bodies right away might overwhelm you two!” My mom is incredible. She is really trying to just go with it and not lose her mind.

“Sure mom.” I shrugged at Lily whose expression assured me that taking a class on vacation was the last thing she wanted to do. “Come on,” I assured her. “Let’s just do that class to give mom and dad time to figure stuff out.” And to continue our flirty game, I added, “There will be plenty of time for you to ogle all the cock you want.” Phew, I got a smile from her. Shit, was I flirting back? If she wasn’t my sister, you’d think I was trying to fuck her. Come to think of it, if she wasn’t my sister, I would be trying to fuck her. There have been plenty of times I heard her and Derek fucking in the room next to mine, and I’d be lying if I said I didn’t jerk myself to sleep hearing that.

“Here we are,” Amelia said, stopping at the end of a hallway with two adjacent huge doors. To the right are the parents, and to the left the young ones.” She used her key to enter the room on the right and ushered us all in.

The heaviness in dad’s shoulders seemed to drop immediately as he took in the room. “Well at least there is this!” He was right. The room was huge and split into two. There was a kitchen area that looked over a decent sized lounge with a giant tv, comfortable couches, and a full wall of windows that looked over the beach area. Through a door brought you into the bedroom that held a king sized bed, in-room hot tub, and a bathroom suite with a giant glass shower with marble bench seating on one side. The glass of the shower went all the way to the ceiling, and Amelia informed us that it could be used as a steam room as well. Back in the bedroom, Amelia opened a door that connected to the lounge area of my and Lily’s room.

“As requested, the rooms are identical, save for the two queen beds rather than the king bed.” At a knock at the door, Amelia said “Ah, here is your luggage,” ushering in a young male porter. “If there is nothing else, I will give you some privacy. Please do not hesitate to call the front desk for any of your needs, no matter how personal. We do try to make your stays as comfortable and pleasurable as we can. Also for a list of activities and resort map, you can press the “information” button on the tv remote. And with that, she handed us the keys with an extra set so we could get into each other’s rooms, and left

“What do you think kids!” Dad was excited again. He was hoping the rooms would make up for his lack of research into the hotel.

“It’s wonderful, honey,” my mom said, stroking his arm. Always the supporter.

“It’s amazing dad. Good work. Hey, check out the view. I think I can make out some naked folk running around on the beach from here!” Lily loved to tease dad. They were definitely closer, and I was closer to mom. While Lily’s teasing was meant to be lighthearted, it brought all the redness and worry back to dad’s face.

“Oh, sweetie. I’m so sorry. I ... I didn’t know...”

“It’s fine honey!” Mom to the rescue. “I’m going to take your father to the room to unpack and settle him down a bit. Why don’t you kids get comfortable and look for that class. We’ll meet back together for dinner.” And with that she pushed my father through the joining door and locked it.

“Nice one, sis,” I said as I immediately cracked open a beer from the mini fridge.

“Already?” She said looking at my beer.

“Hey, it’s all inclusive and it’s vacation. You take one too and loosen up. I want my nice sister, not my stuck up one.”

She caught the beer I threw her. “I’ll have to make it a shower beer. Your nice sister doesn’t smell nice ... shit the class thing is in an hour. Not enough time for us both to shower and get ready. Tub time then?”

Tub time is what we called it as kids when we would bath together because our parents were too exhausted to give us individual baths.

“Aren’t we a little old for tub time?”

“Shut up and just put on your board shorts, then meet me in the shower. Bring your beer.”

Something about her the way she was ordering me around I enjoyed in that moment. “Alright weirdo. We’re missing the rubber duckies though.”

Lily disappeared into the bathroom with her bathing suit in hand, while I rummaged through my stuff to find my suit. I heard her turn the shower on and took that as my cue to enter.

“Ah, what the fuck Jason!”

Apparently I came in too soon and as a reward was treated with a gorgeous view. My sister was standing there in one of her bikinis but had not had a chance to get her top on yet. Her hair was tied up in a scraggly, red mass and obscured nothing of her upper body. Her breasts were so pale and perfectly sized. Not a hint of sag, and her nipples stood out as tiny and pink on nickel sized areolas. The steam building up in the shower behind her made it all feel like a dream. I felt like I stood there for an hour at least, taking in everything I could before I could stammer out, “ssssorry!” I turned to the wall so she could finish.

“Ugh, its fine, turn around. You’ve already seen them and if we are going to be staying at this resort, you should probably get used to not reacting to every pair of tits you see.”

“Are you sure?”

“Don’t be so timid, dork.”

And with that I turned around to get my second view, almost as good as the first. Nothing beats the first.

“Like I said, you have to get that under control if we are going to be walking around together. You won’t be able to get a girl if you are constantly sporting a hard on.”

I blushed. I hadn’t even realized the effect she had had on me. Sure enough, my dick was straining against the edges of my suit, giving a nice outline of my manhood, circumsised head and all. I tried to play it off as a joke. “Hey, I’m topless, your’e topless. Only fair right?”

“Ha ha perv,” she said, not taking her eyes off my bulge. “Let’s hurry up and shower and get dressed to go. Mom will be annoyed if we don’t take her suggestion and get to the art class.”

We entered the shower, which had ample space, and soaped up our bodies. I couldn’t help stare as she soaped up her tits, making little effort to turn her body away. Watching her lather her thick ass almost made me bust my load right then and there. I’m pretty sure I barely washed up, instead choosing to tortured myself with views of her body.

As we dried off, Lily suddenly turned to me with a devilish look in her eyes. “You got your eyeful and I’ll get mine. You owe me, perv.” Again we were playing some game, but I didn’t know the rules. I just knew enough not to cross her.

“Fine, I owe you, whatever.” I was beginning to enjoy when she called me a perv.


On our way to the class, we passed by our parents bedroom, and I could have sworn I heard muffled moaning, but I didn’t have time to check it out.

In the class, there were 8 easels set up in a circle around a stage. Lily, now dressed in her bikini, and I, in my suit and with no shirt, sat down beside each other in the last two available easels. I took a look around and to my embarrassment Lily and I were the only two people wearing clothes, including the resort’s indoor activities coordinator. He was a man in his 50’s, maybe Puerto Rican, medium height, slender body and an uncircumcised penis hanging between his legs. His face seemed kind and serene.

“Welcome everyone. I’m Paul and as a break from the beach going and partying, its nice to sometimes sit still and put our hands to creative use. Everyone help yourselves to some drinks and we will begin once the model arrives.

“Bottoms up,” I cheers with Lily and drank the provided chilled wine in one gulp.

“Uncultured slob,” Lily jokingly sneered, but knocked hers back just as quickly. Looking around the room, we were definitely the youngest, and it was a mix of men and women. Two girls caught my eyes as they seemed to be a couple. As they drank they stayed close, and one gently circled the others lower back with her finger. Such as small move, but while naked, so erotic. (Yes, I’m a horny kid perving on a nice lesbian couple).

“Well, it appears we may have to postpone,” Paul announced. “Our model isn’t coming. Unless we can get a volunteer.”

I looked over at Lily expecting disappointment, but was met with the same devilish eyes from the room earlier. “Remember, you owe me” is all she said before announcing “My boyfriend would be happy to chip in” while raising my arm in the air.

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