Family trip to Jamaica Part 2 by robdcruz

“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.

Before I could say “Boyfriend!?” the rest of the class gave appreciative claps, and Paula came my way.

“Come come, let’s hurry. Thank you so much. If you would please disrobe and take a set on the stage before I direct you in your pose.”

Before I could protest, Lily had undone my suit’s tie and “helped” me out of my shorts. I said “helped” because she really just pantsed me. I think she was enjoying the prank a bit too much, because she didn’t think through what would greet her while bending down to pull off my pants. No sooner had she got them off than she had come face to face with my semi hard (but confused) penis. A look of shock registered, before an expression of quick desire.

Paul pulled me onto the stage, and posed me. “Lean this way please, and move your leg like so,” Paula directed, not being shy to grab any part he pleased and move it where he wanted. I was posed with one arm resting atop my head, the other to the side, while leaning half an ass cheek on the chair. Totally exposed. “In the next 30 minutes I want you all to try to capture this young man’s vigor and strength.” Paul turned to whisper in my ear, “I need you to show some more strength, please.” As I clearly did not understand him, he sighed, said something about “tricks of the trade” and surreptitiously gave my dick a few quick pumps. My flaccid 5 incher, became a straining 8 inch dick in no time. Although Paul was definitely not my type, his taking charge and making me feel dominated had an arousing effect on me.

I looked over the Lily to see if she was regretting her prank yet, but she was staring at me in the same way she had stared at the guy in the lobby. When we made eye contact, she shifted here eyes away and pretended to become absorbed in painting.

“Have fun everyone and grab some more wine. Remember, it doesn’t have to be perfect, but make sure to get his *ahem* strength to full effect.

30 minutes is a long time, but it went by surprisingly fast. Each time I would start to lose my erection, Paul would dutifully give me a few professional pumps and I would be good to go again. He seemed to really love his job as I got a few pumps when I was still pretty hard. I had to hold myself back from cumming each time, not so much from his touch, but what it felt like to be touching while being watched. All around the room, most of these amateur painters were here not for love of craft, but because they enjoyed nudity. They were staring at my fit chest, the muscles in my legs, and at the length and thickness of my cock. It made me feel strong and desired. I imagined they were just as turned on as I was. And in the case of one painter, a man in his mid 40’s with gray but fashionably styled hair, I knew he was turned on by how he couldn’t help but give himself and idle stroke now and again. Between this and the cam sessions, I’m realizing I’m a bit of an exhibitionist.

I rejoined Lily when the time was up, and surprisingly didn’t feel the need to immediately put my shorts back on. “Well I owed you, so there it was. Let’s see what you drew,” I said, trying to be as casual as possible.

Lily was blushing but trying to play it cool. I could tell she didn’t want to betray that she actually might have enjoyed watching me up there in the nude. “I’m not much of an artist so I could only guess what Paul meant by capturing your strength.” She turned the canvas to me, and it was pretty clear what she thought strength was. While you make out out my form, the one clearly defined part of the image was my dick coming out of a mess of black hair.

“Oh man. Is that what people see when they see my dick? Is the hair that bad?”

“I don’t think it’s bad. I actually…thought you have a nice di…penis.” Lily said shyly, blushing the whole time.

“He does, and you’re a lucky girl to have that to play with” said one of the lesbian women with a funny wink on the way out of the room.

The whole way back to the resort room I felt really uncomfortable. A mix between feeling a horny high from being on display and getting stroked for half an hour without release, and feeling self conscious about having so much pubic hair. All this time being single recently has made me forget the importance of manscaping. Lily noticed that I was off when we got in the room, and in what seemed like a sudden rush, poured herself a doubleshot of rum from the minibar and started furiously rummaging through my things. “Where is it?”

“What the hell, where is what!?”

“Ah ha!” Out came my electric shaver, and I started to put two and two together. Lily offered: “Listen, I think it looked fine, but if you are going to be so annoying about it, then let’s just shave it off. Get in the shower.”

Let’s? I was about to tell her I could do it myself, but the tension in my balls stopped me and forced me to follow her to the bathroom.

“Ok, it’s no big deal right? Just drop your shorts and I’ll make sure to make your dick something you can be proud of.” Lily seemed determined to cheer me up, and I do think a little buzzed from the art wine and tequila shots. It was probably the tension built up all day, but I offered no protest.

I slid my shorts off, revealed my semi hard dick to my sister. Her face was stern with concentration as she approached with the shaver, but her nipples were hard as rocks, and made my dick twinge. “Ok, good,” she said noticing the movement. “I think it will be easier if you are hard.” Again, she was approaching this like we were solving a problem together, but I was beginning to feel like she was getting into this. I decided to push my luck.

“Well, can you help with that?”

My heart stopped and it felt like an eternity of dead silence. When I looked up, Lily’s face had changed. Her eyes softened and her face exuded desire.

“Oh. Does my little brother want his big sister to make his cock hard? Mmmmm. I couldn’t take my eyes off you giant dick in class. Come on, can you show me your strength again or should I call Paul?”

My stomach turned with anticipation. “Why don’t you make it hard for me.”

“Does my little bro like this?” And with that she toyed with the string on her bikini. Although I had already had an eyeful of her tits earlier, the way she was speaking was making me feel hungry for anything she would give me now. I was instantly rock hard as she slipped her top off, revealed her stiff, tiny nipples on her perfect pale breasts.

“Knew that would work!” She laughed. “I was pretty good at talking dirty with Derek, and he liked some kinky role play stuff. Not the first time I’ve been the slutty sister.”

“What the fuck? Was that all an act?” I was a little hurt, not going to lie. Not hurt enough not to still be turned on by her bare breasts that she was now covering with one arm (somehow this was also super hot).

“Hey man, just getting the job done.” And with that she walked over and turned the shaver on to start trimming my balls. “Not the first time I’ve helped someone shave either.” With the penis out of the way, she made quick work of my balls. “And now for around the shaft. “

There must be something int he water (or rum) in the resort because without a moments hesitation, my sister put her hand around my dick and moved it down and out of the way to facilitate her work. An electric shock ran through my entire body. I couldn’t believe my sexy sister was holding my dick, while topless. I tried to keep still, but could feel my body instinctively trying to rock my hips and pump myself in her hand.

“Lily…I….”

“Shush. I’m almost through.”

“No, I…” More waves of pleasure rippled through me as she shifted her grip and gave my dick an unintentional squeeze. The warmth and pressure of her grip and she intense eroticism of being touched by your sister. I couldn’t stop it. Before I could utter another word, streams of pent up cum shot onto my sister’s chin and chest, pooling between her perky, perfect tits. I don’t think I’ve cummed so hard or felt so fantastic in my life. My knees buckled and I held onto a towel rack to keep from falling. After the waves of pleasure ended and I settled into the after-cum drowsy feeling I always get, I was suddenly reminded of how this happened. With sudden guilt and fear I looked down at my sister, still topless on her knees and who seemed to be frozen. The look on her face was of shock to be sure, but not disgust.

She slowly stood up and, careful not to drip any cum on the floor, walked into the shower. “Well come on and help me clean up, little brother.” It was as if those words were now a command I couldn’t disobey and I dutifully joined her in the shower and helped her wash the cum from her tits. She seemed to enjoy the command she had on me, and I enjoyed the work. When we were done, we dried off and she looked at me , saying “You owe me another one, little brother. Now get dressed.”

Of course I listened. The girl just gave me the orgasm of a lifetime. In my drowsy stupor, I’d kill someone if she asked me to. We got dressed and didn’t say much for about 15 minutes.

Lily spoke first. “Lets see what mom and dad are up to. Hopefully dad is in a better mood than before and mom will be happy we are getting along so well.” We knocked on the door and mom let us in.

Sure enough, dad had a big smile on his face and looked just as contented as I did in that moment….

Part 3 to follow.