Read Story: SEASON 1 EPISODE 1

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."