Chapter 1

Nothing exciting ever happens in this town. I know I know. This is what every 16 year old boy complains about, but seriously it’s the same routine, day in and day out. Go to high 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 at school.

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.”

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.

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.