Family Trip to Jamaica Pt. 01

Nothing exciting ever happens in this town. I know I know. This is what every 18 year old boy complains about, but seriously it's the same routine, day in and day out. Go to school: walk home with my sister; mom and dad come home from work later; eat dinner; jerk off; go to bed. Rinse and repeat. Don't get me wrong, I love my family, even my stuck up sister, but I need more.

So leading up to summer I made sure to drop hints to my parents that we needed to do something grand. My mom and dad are never ones to shy away from a challenge, and dutifully set out to shut me up. A little before school was to let out they called a family meeting (yes, those don't just happen on TV) and announced they'd booked a vacation to a luxury resort in Jamaica.

I couldn't stop myself from exclaiming, "Holy shit!"

"Language, Jason," my dad said with a smile.

"Yea, relax dork," my sister chimes in. " Don't act like you've never been anywhere before. You'll sound like a yokel."

"Be nice to your brother, Lily. He's just excited. We know how you guys have worked hard this year and deserve a good time."

"Yea, be good you two. Your mom and I talked about how we want to start trusting you, and this vacation is part of that. We plan to give you guys a little more freedom there, so you have to look out for each other. From what I hear, they are pretty relaxed on their drinking age, but step out of line and you'll be stuck with mom and dad and virgin Shirley Temples the rest of the trip."

"Virgin drinks for a virgin boy," my sister sniped.

"Screw you, Lily. You're just sour since you're not getting it on the regular since Derek broke up with you?" I regretted it as soon as I said it, but she's been a real bitch since she walked in on Derek going to town on a mutual friend.

My dad let out a sigh of exasperation. Or was it something else?

My mom chimed in, "Both of you stop. Lily, drive your brother to the mall and pick out some vacation clothes. We'll be beachside for much of the vacation but we might do some hiking too. Get along."

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On the drive over to the mall I felt a little bad about what I said to Lily in the heat of it. Truth is, we are usually pretty close. Mom shot us out in quick succession so Lily is only about a year and a half older than me. The family joke is that my dad waited the exact amount of time the doctor recommended before pouncing on mom again after she had Lily, and poof, here I am.

"Sorry for being a jerk," I murmured.

"Sorry for the virgin jokes."

After an awkward silence, she asked, "What's the deal with that by the way? Shouldn't you be living it up and knee deep in girls. What's the hold up?"

"I don't know. It just never works out." And that's the truth. I'm confident enough to say, I'm a pretty good looking guy. I'm 5'11", with black hair, hazel eyes, and I've been told, a nice ass. I keep in shape, and am quite proud to show off my 8 inch cock where I can. What I couldn't tell my sis was that I'd been close so many times. Something just gets in the way. With my last girlfriend, we did everything. Handjobs, blowjobs. Hell, even titjobs (she had massive tits. It was fantastic). And don't think I didn't give back. I eat a pussy like no other. I actually really love going down on girls. Having someone clamp down on your head with their thighs while you circle their clit with your tongue and the explode in rapture is incredible.

But as soon as it got time for the main event, her family upped and moved because the mom's job transferred her out of state. Jerking off together over video chat loses its allure pretty quick when you've almost had it all. And various hooks ups after that just haven't got there.

It's been so long since I've had any real sexual contact that I've developed a pretty involved cam2cam habit on Omegle. It's kind of fun to jerk off with some random girl. And to discover the thrill of having gay guys beg to see your dick and watch you cum was a nice bonus too. Like I said, I'm not shy about showing off my dick. But this vacation needs to go well. I have to fuck someone. Maybe I'll find some hot island teen who will let me fuck her on the beach. Just the thought was making me hard when my sister's voice brought be back to reality.

"Well, maybe in Jamaica I could be your wingman. I'll help you pop that cherry."

"Thanks..." It was kind of weird to see her be THIS chummy with me. Must have made her feel really guilty before. Hearing her talk like that made my cock stir even more. She wasn't helping my frustration in the least.

At the mall we hit up the regular spots for some clothes and decent hiking shoes. We headed to the bathing suit section and went to try a few things on. I chose some run of the mill board shorts and with my sisters encouragement for some more stylish short trunks that hugged my ass and junk. All the rage with the ladies now, she assured me.

What I wasn't prepared for though, was how incredible my sister looked in a bikini. It's been years since we went to the beach together, and sure around the house I'd see her in all manner of dress (and undress between showers- we can be pretty liberal in our house). But nothing compared to seeing her in a black suit, tied with a tiny string in the back and hugging her body. She was about 5'3", very fit from years of soccer, perfect C cup tits, and an ass that put her squarely in the category of PAWG. The suit wasn't a thong up her ass by any means, but there was just plenty of skin to see. For years, I have tried to resist the urge to stare at her ass while she ran up and down the field in soccer. Not to gild the Lily here (pun intended) but her body has even caught dad's eye on occasion. He'd never admit it, but I think he sometimes enjoys a peak at his beautiful creation. Seeing her like this also made me appreciate how sexy her red hair was when against her pale skin.

"Jesus!" I really couldn't keep my mouth shut. I had to work on that.

"What?" Lily seemed surprised. "It's a one piece. It's no big deal."

What she called one piece was technically true, but there were plenty of slits and cleverly placed open spots that left less to the imagination than any of Aunt Amy's one piece suits.

"Well glad you like it, perv. I got a few more that put this to shame. It's Jamaica after all. I assume the competition for attention on the beach is going to be fierce. I need some love too!" It was good to see my sister less stuck up, and back to her old attitude. Needless to say, that night I logged on to the camsite as soon as I could.

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The flight to Kingston, Jamaica was over 5 hours. Just long enough to take a nap and still wake up restless. Lily was back to her stuck up self and kept her head in her iPad most of the flight. Mom and dad sat separate from us and were extra cuddly in their business class seats. Vacation always brought out a lightness in them which was nice to see. I nudged Lily at some point to gesture over to what I assume was mom's hand at dad's crotch under the blanket. You couldn't tell from their faces, but I swear mom was expertly jerking dad off without being seen. Could have been my imagination though.

"Gross," Lily said quietly, but I could detect a hint of a smile on her face as she shifted in her seat. She enjoyed our parent's closeness as much as I did. We had relatively young parents. They were high school sweethearts and had Lily at 18 as a "happy mistake." My mom was 37 and I'm proud of how my friends talk about her as a "MILF." My sister and I must have got our athleticism from dad, because mom's body was more lithe and slender. She had the same pale skin and red hair as my sister, with at most B cup tits that still stand up firm and perky. Her ass was full and round, filling out her mom jeans nicely. She keeps in shape with periodic bouts of yoga like most suburban moms, which is enough to keep herself nearly as flexible as she was in her teen gymnastic days. Dad is 37 as well and has the kind of body you can tell used to be all muscle but is on its way to being a "dad bod." He's about 6'0", with black hair like mine, and a hairy chest. Together, they make a good looking pair.

The plane landed and we took a shuttle for what seemed like a good while to the resort, which was apparently on a beach set apart from the main touristy spots.

"Where is this place?" As I said this, I noticed that there was only one other set of people on the shuttle; a dad and his daughter.

"Told you kids, we spared no expense," my dad said. "This place is supposed to be pretty exclusive. A friend from work recommended it to me. Said he takes his kids here all the time. Honestly, I just looked at the 5 star reviews and trusted my friend." I could tell he was beginning to get a little nervous. Dad likes to take ownership and credit for our vacations, so it means that it's on him if it doesn't go well.

Pretty soon the road opened up and before us was a beautiful, modern looking resort, set among a background of shining blue water. Some of the worry started to melt away. If it's this gorgeous, what could go wrong? Lily, mom, and dad were all entranced with the water, but something else had caught my eye. It flashed by so quick that I could question what I saw, but I swear I just saw a naked man and woman walking to the resort on the side of the road. They must have been wearing bathing suites and I just couldn't tell.

The shuttle pulled up to the palatial entrance, and two porters rushed to take our bags and welcome us in. We walked in to the lobby to the front desk, eager to get to our rooms.

"Wait until you see the rooms your dad and I picked out. Two nice big adjoining suites. You and your brother will have your own suite as part of the independence we want to encourage. But your dad and I will of course have a key." That sounded awesome, especially if I was going to bring back an island babe to the room. Though I was beginning to get the impression mom and dad wanted the space for themselves too.

"Honey...?" I heard my mom say in a worried tone. I looked over to see her staring at the couple I had seen on the road earlier. Sure enough, they were stark naked! They were a black couple, tall and attractive. The girl had very dark skin, and melon sized breasts with the most perfect small dark nipples to top them off. The guy was bald, with a beard and sunglasses, a six pack and the biggest dick I'd ever seen. And from the looks of if, the biggest one Lily or my mom had seen. While mom's face was of shock, Lily looked like she was trying to soak it all in. The guy apparently noticed and shot a smile to my sister that made her blush.

I looked over to dad to see his reaction, but he was busy arguing with the concierge. As much as I didn't want to tear myself away from the image I would most likely be masterbating to later, I went over to see what was wrong.

"But I've got kids with me. I listed their ages when I registered," I heard my dad say.

"Yes, I see here, 18 and 19. That is not a problem sir. We allow any family to stay here, with only some restrictions on areas and activities for 16 and older. It is all here in the pamphlet. Now, please let Amelia show you your rooms as I have others guests to register." By that he meant the father and daughter who were on the shuttle and seemed eager to get to their rooms. The dad was holding her up on his back by her legs, giving me a nice view of her little ass as she wiggled excitedly. It didnt seem like their first time here.

"Family meeting!"my dad called, as he signaled for Amelia to wait. She shrugged and stepped back to give us some space.

"What did they say, honey? And did you see that naked couple. I mean his..." My mom stoped and shot my sister and I a look.

"I dont know how to say this, but apparently this is a clothing optional resort. Like I said, its well rated, but the norm here is to be nude in most of the areas, except the formal dining room. I'm so sorry kids, I think we might have to leave."

Surprisingly, my mom stopped him." Wait a second. We've come all this way, and I'm sure we wont get our deposit back. Lily is 19, and Jason is a very responsible young man. Plus, you and I have always talked about going some place like this." Lily's eyes worriedly shot back and forth between us and the black man's dick. It's as if she was worried it would disappear.

"Alone! Not with the family. Back me up here kids."

"Relax dad," Lily said. "Its optional right? Meaning if someone chose to they could keep their clothes on. I bet only gross old men will be letting it all hang out. And Jason sees plenty of tits on his cam sites, so its no big deal to him."

"Hey!" I shouted. She wasn't wrong about how much porn I've seen (though how did she know I visited cam sites), but it was very much still a big deal for my 18 year old mind to see glorious naked bodies. As they were arguing I was already building elaborate fantasies of what could happen here.

My mom spoke up again. "Honey, I really think we should give it a shot. We did say we wanted to give the kids more leeway and responsibility. Well, here is their chance for them to show us they can handle some adult fun."

I could tell my dad was not completely sold, but he always trusted my mom and often relented to her. She's always been more go with the flow. Thank god for that right now!

"Ahem," Amelia finally spoke. "Please, we must be on our way. Let me show you to your rooms. I am sure you are eager to get out of your travel clothes and begin enjoying the resort."

"Fine," my dad said. "Thank you. Please show us to the rooms."

"Right this way."

Hell yes, I thought to myself. All I had to do was get away from my sister, and a whole resort of pleasure was up for grabs. I could tell my horny mind was getting carried away, but I didn't care. As we were shown to our rooms, I saw the father and daughter from the shuttle making their way to their rooms as well. I guess it was no crazy surprise for them what this place was all about. They seemed especially comfortable, as the dad walked with his hand in the back pocket of her tiny jean shorts.

"Huh, close family" I thought.