Richie hung up the phone. A huge smile formed on his face. He picked back up his phone, but paused, not sure who to call first. He couldn't believe he had won.
Richie, a small-framed, brown-haired kid, who had just turned 19, tapped his mom's contact.
"Mom, I won," Richie exclaimed. "I have the best job in the world!" Richie quickly jerked the phone away from his ear to protect from his mom's screams of delight.
Richie had been chosen out of thousands of applicants to watch a private island for its owner. His main duties included keeping a daily blog and watching over the island with its small group of caretakers. And before Richie knew it, he was landing in his new home.
Richie watched as the plane that had taken him to his paradise island, taxied on the runway and took off. He watched knowing that it would be a full two months before it would return.
"Hi," a voice said from behind. "I'm Geoffrey."
"Hey, I'm Richie."
"I'm one of the caretakers, let's go inside and I'll introduce you to the others."
As Richie followed him inside, he thought of how Geoff had the look of an island caretaker. Light brown skin, tall, thin and fit, even wearing loose, and slightly baggy clothing.
Once inside, Geoff introduced Richie to the two other island inhabitants: Dante and Shelby.
Shelby was average height and had a more medium build. He was white with light brown hair.
"Hey," he greeted, "I'm an outdoor caretaker, with Geoff."
"He's my assistant," Geoff interjected.
"We're equals," Shelby countered.
Richie turned his attention to Dante. Dante was thin with sideburns that connected to his goatee. Somehow the look worked for him. Dante was white, but had some ethnicity...maybe Italian...
"Hi, I'm Dante," he started, "I keep up the house."
"He's the maid," Geoff added, with a smile. Richie smiled, it was clear they had a fun working relationship.
"Geoff's just mad because he lost at basketball," Dante explained.
"Rematch," Geoff said, pointing in Dante's direction.
"You guys play a lot?" Richie asked. He had always been decent at basketball, although he wasn't real tall.
"Yeah," Dante informed, "we usually play a game or two every afternoon."
"Cool," Richie supported.
"Dante," Geoff ordered, "Why don't you show Richie to his room?"
"Yes, master," Dante said with a smile, as he motioned for Richie to follow him.
Once they were out of ear shot, Richie asked, "So is Geoff, like, the boss?"
"No, we just let him think he is," Dante said with a smile.
***
At dinner, the four guys sat around the table, eating grilled chicken, prepared by Dante.
"I'll admit," Shelby began, "that we had been hoping a girl would win the contest. But you seem okay."
"Thanks," Richie responded, noticing Geoff grin at Shelby's comment. Richie paused, he wanted to say something, to take a leap. One voice in his head pointed out that he barely knew the three other guys, while another voice countered he might as well be honest since they would be housemates for a while. By the time Richie worked up the courage, the conversation had taken another path.
"After the grass, the boat docks need some repairs," Geoff was saying.
"No problem," Shelby responded, "I'm almost done with painting the fencing."
Richie decided to redirect, "So you guys have girlfriends back somewhere?"
"I do," Shelby was first to answer, "Long distance relationships suck."
"I'm single," Dante answered next, "this job does have drawbacks."
"I'm single too," Geoff responded, "you?"
Richie took a deep breath, "Well, I'm bi, but single right now."
"Bi?" Dante asked.
Geoff and Shelby starred, as they waited for his answer.
"Yeah, bisexual," Richie clarified, "basically, I'm not picky when it comes to sex."
"Gotcha," Dante said. Geoff didn't say a word, but Shelby looked curious.
"So," Shelby started, "you've had sex with guys?"
"Dude?" Geoff interrupted, only to have Shelby gesture for him to buzz off.
"Yeah," Richie answered, "A few times."
"So what," Shelby continued, "are you like the pitcher or the catcher?"
Geoff put his food down nosily, and Dante looked increasingly uncomfortable, but Shelby wasn't being denied.
"Well, I've done both," Richie answered, "But I guess my preference is catcher."
"This is sick...I'm trying to eat," Geoff said, raising his voice. "Look," he said, looking at Richie, "whatever you're sexually into is fine with us, but we're all straight. And Shelby, if you want to quiz him then fine, but not while I'm trying to fucking eat."
With that, Geoff got up and left the dining room.
***
Richie laid on his bed, in a pair of blue pajama pants, and a white t-shirt, reading a book when there was a knock at the door.
"Come in," Richie yelled, as Shelby walked into the room, closing the door behind him. Richie looked him over, wearing a pair of worn blue jeans, boots, and a short-sleeve polo shirt.
Richie thought of Shelby as the more outgoing of the three, but at this moment he actually looked at little nervous. "You're probably getting pretty horny, being here for four days now, with all straight guys."
"I guess," Richie responded, not sure what to say, "I'll manage."
"Yeah," Shelby continued, "I'm sure horny. I haven't seen my girlfriend in almost a month."
"That sucks," Richie said. Richie started to connect the dots, but he needed to be sure he wasn't crossing a line. "Is there anything I can help you with?"
Shelby paused. "I think you know what I need help with."
Richie watched as Shelby dropped his hand down and grabbed at his crotch. That was more than enough of a hint for Richie. Richie reached out putting a hand on each one of Shelby's butt cheeks, and then pulled him to the edge of his bed.
Shelby's crotch was just inches away from Richie's face, as Richie moved a hand towards his fly.
"Wait," Shelby stated, stopping Richie as he had just unzipped Shelby's jeans.
"I'm not sure what you expect from me," Shelby quietly explained. "I mean, like, I'm not so sure about returning the favor."
"No problem," Richie assured, as he reached into Shelby's fly. Richie's hand reappeared, with Shelby's mostly soft dick in it. Richie didn't waste any time in playing with it, running his fingers over its smooth shaft and plump head. Richie used his other hand to rub Shelby's balls and ass crack through his jeans. It wasn't long before Shelby's dick started to expand.
"Yeah, jerk it," Shelby softly moaned, as he pulled off his shirt, exposing his solid chest.
Within a minute, Richie found himself looking right at a hard seven and a half inch pole. Besides the length, Shelby had a considerable thickness, it was definitely a meatier cock.
"Kiss it," Shelby stated, as Richie's small, soft hand worked up and down his rock hard shaft.
Richie glanced up at Shelby's wanting eyes, and then back to his rocket. Pointing it straight ahead, Richie leaned in giving the head a gently kiss. Before Richie could react, he felt Shelby's hand on the back of his head and his mouth pushing forward over Shelby's hard cock.
"Yeah," Shelby moaned as his pushed Richie down six inches worth of his dick, before letting go. Richie retracted his mouth to Shelby's head, and then to Shelby's surprise, he gulped down all seven and a half inches.
"Oh, Fuck!" Shelby moaned, as Richie buried his nose in his pubic hairs. Shelby didn't have the slightest idea that between his length and girth that Richie was barely able to keep from gagging.
Richie kept swallowing the better half of Shelby's cock, as Shelby rolled his head back moaning. Shelby could feel his cock filling with warm giz, as he looked down towards his new friend. His shaft glistened in Richie's salvia, as Richie greedily sucked on his meat.
Richie's soft, wet lips slid up and down Shelby's rod for about five minutes, before Shelby yelled out, "I'm gonna cum!"
Richie pulled back, allowing Shelby's ready cock to drop out of his mouth. Then Richie wrapped his hand around Shelby's shaft and started jerking.
"Oh, oh!" Shelby moaned, loudly, "Fuck!" Shelby's load gushed out, landing on the hardwood floor beneath him. After half-a-dozen shots of thick cream, Richie wrapped his mouth around Shelby's head to catch the last of the drizzle.
"Wow," Shelby said, catching his breath, "That was great."
Richie took one last gulp of Shelby's softening cock before pulling back. "My pleasure."
"So," Shelby started, "we're cool?"
"Definitely," Richie confirmed.
"Cool," Shelby responded, as he shoved his dick back into his jeans. Shelby quickly threw on his shirt and was out the door.
Richie watched him shut the bedroom door shut. Richie thought to himself how Shelby has a near perfect dick. It was big enough to satisfy his urges, yet it didn't hurt his jaw to suck on. Richie smiled, as he thought of something else Shelby's dick was perfect for.
"That would probably hurt a little," Richie said, quietly to himself. Then Richie looked down to the floor at the puddles of warm cum.
***
Shelby opened the screen door and walked into the house. He turned down the long hallway towards the bedrooms. Now done with painting, he had to retrieve his tool chest and get down to the docks. Of course, he had left it in his bedroom.
As he moved into the doorway he noticed, Dante sitting at his computer. Shelby couldn't help but smile. Dante was watching porn, and clearly hard at work.
"She has nice tits," Shelby commented about the porn.
Dante quickly turned, just enough for Shelby to get a glimpse of his hard-on. Then he turned back towards the computer, as he forced his rocket back into his pants. "Sorry," Dante murmured.
"I know where you can get a great blowjob," Shelby offered, as he walked into his room and grabbed his tool chest.
"Where?" Dante asked, turning to face him, zipped up this time.
