Dares of Sailor's Creek

[Nick]

Been awhile since I've posted a story but I wanted to give it another shot. I wrote this story awhile ago and haven't finished it (about 7 1/2 parts in). So I figured I might as well start posting it and if people like it i'll attempt to finish it.
Enjoy

Day 1.1: The First Breath of Vacation

Rob threw his duffle into the trunk of his SUV, the over-stuffed luggage wedged oddly into the corner, but it was good enough. And then Rob waited. It was 6:54 am, early enough to be up on a school day. However, by the grace of God, he didn’t have school today. Today was officially the first day of spring break: the last vacation before high school was finally over.
“Hey!” A lazy, feeble voice called from next door. Kenny, Rob’s neighbor since he could remember and long time friend, was shuffling across his lawn, dragging a full suitcase behind him. He was clearly tired, rubbing his eyes as if somebody had kicked sand into them. He finally reached the car, wheeling his suitcase around with all lack of care and positioning it for Rob to lift into the trunk with zero idea of doing it himself.
“Glad to see you up and wide awake,” Rob said jokingly, not minding too much as he struggled to lift the heavy suitcase in without scratching his car. After all, this vacation wouldn’t be happening without Kenny’s parents who were funding almost half of the entire trip’s costs. It was conservative to say Kenny’s parents were rich. The only reason Kenny was even his neighbor was because Kenny himself didn’t want to move during his school years, so his parents put up with the large (modest in their eyes) sized house they had in New York while keeping their massive sized house in North Carolina ready for them to move in the second Kenny graduated. Kenny was a junior, they still had another year to wait.
“FREEDOM!” someone called from down the street. Rob knew who it was but couldn’t see them from behind the trees that lined the street. Then, sure enough, Ricky came jogging down the sidewalk with a duffle similar to Rob’s.
“I’ll get in the back seat, I need to sleep for a few hours more,” Kenny told Rob.
“No prob,” Rob replied as Kenny climbed in and Ricky ran up, giving Rob a rather goofy man hug. Rob took Ricky’s bag and threw it in the trunk, then slammed the trunk shut.
“Finally, Spring Break baby!” Ricky announced before screaming, whooping and yeehawing at the top of his lungs before getting in the car. Rob started the car.
“Sailor’s Creek, here we come,” Rob announced and threw it in drive. From the suburbs of New York, they were driving down to the little-known but growing tourist location called Sailor’s Creek, Florida. After a lot of research, Rob decided this would be a great spot to go. It was on the gulf coast of Florida. It wasn’t too crazy but still well known enough to have other springbreakers partying there. And, with the obvious help of Kenny’s parents, a few odd-end jobs and a whole lot of begging, they could rent a beach-front condo for the whole break. Usually meant for four people, it was the perfect place to relax and have an awesome Spring Break.

Day 1.2: The Long Drive

Rob had been driving for an hour, and they still had a long road ahead of them. If they were lucky, they’d arrive at their condo sometime tomorrow after driving through the whole night. They had three able drivers and Rob was the first shift.
“So,” Ricky started, deciding to strike up a conversation after becoming bored from his ipod, “who all is going to be in the area?”
“Uhhh, let’s see,” Rob stated, rattling his brain alive to think. “Well I know Jerry and Jay are going to be there.”
“Those two guys in our math class? They’re nerdier than Kenny.”
“Hey! He’ll hear you and he’s a good friend of mine!”
“I know, I know but he’s sound asleep and you know he’s a nerd.” What Ricky said was true. Kenny was considered one of those shy nerdy kids but Rob still liked him, he was really nice and would be fine if he wasn’t so shy. “Ok, who else?”
“Ben Killman and some other guys from the football team will be just a couple towns north for a football training camp. I know some girls from the soccer team are going to be renting a small place somewhere in town. And Anna, one of the cheerleaders, will be staying somewhere in town too with a few friends.”
“Cool, we’ll have to call all of these people up once we get there!”
“Heck yes!” Rob was even more excited now. Kenny and Ricky were easily his two best friends. Kenny had always been his neighbor and even though Kenny was a year younger, he was still cool enough to have fun with. Ricky was Rob’s friend from the varsity swim team. They had met in middle school and were instant friends since that day. Ricky was the funny, crazy, outgoing kid that everyone loved to have around. Especially on Spring Break, it would be a blast.
“And what are we doing on your birthday?” Ricky asked.
“Oh yeah, right, I don’t know.” Rob had almost forgotten his birthday fell during Spring Break. That was just an added bonus, he’d be turning 18.
“We should have a party,” Ricky was getting over-excited now and Rob just nodded at his endless ideas. “We should play some truth or dare too.” Rob shot a look back at Kenny from his rearview mirror to make sure Kenny was asleep.
“You and your crazy dares again huh?” Rob asked, trying to keep his eyes on the road. From all this talk of friends, parties and now dares he was getting excited. He never assumed Ricky would want to play truth or dare again; it was something they hadn’t done since they were sophomores.
“Yeah man, it’ll be great this time,” Ricky said. “I found all sorts of cool ones online. It’s always fun when you and me play. Kenny will love it too. Especially if we play with some other kids too.”
“Sounds like a plan then,” Rob said.

[Robbo!]

I know it's early to judge a story, but I like it (particularly your character's name choice). I really want to see how this one develops.

[Nick]

Thanks for the reply, now it starts to get a bit better.

Day 2-3.1: Arrival

After several stops for snacks or a toilet and after a few hours of sleep at a rest area along the way, the group finally made it to their condo at 7p.m. The first thing Rob noticed as they pulled up into the driveway of their temporary home, and the characteristic he liked the most, was that it was secluded. Tall bushes separated this house from the rest as well as gates in the front and, as they would soon discover, before the beach. They all unloaded their own bags and shuffled inside, happy to not have to be in the car for so long anymore.
The condo was very nice. It was lightly decorated and very open, just one story with 4 bedrooms, a full kitchen, three bathrooms, a living room and a small pool and hot tub outside under a screen. Rob quickly claimed the room that was closest to the beach that had a view of the pool as well while Kenny chose the room opposite of Rob’s and Ricky chose the room that shared a bathroom with Rob. They didn’t really talk much after picking their rooms and Rob fell asleep soon after deciding that unpacking could wait until morning and collapsing on his bed.

Rob woke up fully clothed on top of all the covers of his neat bed. Rob quickly realized how exhausted he must have been and decided it was time to start his first full day in Florida. This was the real spring break. He took another tour of the condo. Ricky was still asleep even though it was 11am and Kenny had left a note saying he was going to shop for groceries. Bless his heart. So, Rob decided it was time for a swim in the ocean.
He donned his board shorts, wearing the Speedo he wore on the swim team underneath and walked out to the beach, carefully locking the gate behind him. The sand was white and pure, the ocean quiet, calm and overly peaceful. There weren’t many people out, only a few elderly people taking a walk and some kids way down a ways. Rob laid out his towel and enjoyed the feel of the sun on his skin. He looked around carefully after a few minutes and saw nobody nearby so he stood up and removed his trunks, standing in just his Speedo. Nothing was wrong of course with wearing just these small black briefs but he felt weird wearing just them in public. In truth, this was all he liked to swim in.
With a leap into the water, Rob was swimming swiftly out towards the horizon. His shorts laid lazily on his towel back on the beach and his keys resting safely underneath the towel. He swam quite a ways out and after a few minutes he looked back at the beach to check his progress. He wasn’t as far out as he expected and he also spotted three girls walking down the beach towards his stuff. Paranoid as always, Rob decided to watch and make sure they didn’t steal anything. It was too far to tell their exact age and features but they looked young, all in their bikinis and all able to pull off their suits well. They paused when they passed Rob’s stuff and Rob swore she saw one of the girls point and laugh at his stuff on the beach. They all casually looked around, looking for the naked guy swimming somewhere out in the ocean. They didn’t see Rob and he wasn’t naked either. The girls kept going so Rob decided it was time to swim back and dry off.
Back at the condo and in his trunks Kenny was back and Ricky was awake, showering. Kenny was putting all sorts of food in the fridge and cupboards for everybody. So far, the break was working out great.
“This is awesome,” Rob said. “Without your parents none of this would have been possible!”
“No problem man, they’re happy to chip in every now and then.”


Day 3.2: Games

After eating a small lunch, Rob got a quick shower in one of the bathrooms. It was nice to wash the salt water off his body and the shower what much warmer than the ocean. He came out, fully dressed, to find Kenny and Ricky having a small argument over something.
“You can’t just have parties here every night! I wanted to get some studying done,” Kenny was saying.
“What’s going on?” Rob dared to ask as he walked into the kitchen.
“I was texting Anna and I invited her and her two friends over tonight,” Ricky said.
“This is just gonna turn into some crazy party! Besides, both of Anna’s friends are in my grade and I think they hate me!”
“Oh, who are her friends then?” Rob asked.
“Lexi Tamaya and Tasha Luxenburg, both juniors,” Ricky told him.
“Yeah, Lexi is in my band class,” Rob said and then turned to Kenny. “And they don’t hate you. At least they don’t show it!”
“Whatever, I still don’t want this place to turn into party central.”
“Okay, then let’s come up with a compromise. Anna, Lexi and Tasha can come over later to party. If it doesn’t work out and it gets too crazy for you, Kenny, then we won’t have any more parties here over break.” Rob was pleased with his idea. Ricky started booing at the plan but Kenny nodded and accepted.

By 6pm, there was a knock on the screen door to the pool. Rob was the first to get up from the living room and he walked quickly to answer the door.
“Hey,” Anna said as he walked around the pool towards the door. “You guys got a really nice place.”
“Thanks,” Rob replied as he opened the door, letting his guests in. Tasha and Lexi both greeted Rob as well. Lexi sounded oddly excited while Tasha sounded like she couldn’t be more bored. Anna walked in first, carrying a case a beer in each hand. She looked stunning in her jean skirt and tank top. Tasha came in next, quickly towing Lexi behind her. Tasha had dark skin and short black curly hair. Lexi had her light brown hair down; she was wearing her usual jeans with a t-shirt. All of them smelled like suntan lotion like they had been out sunbathing all day. Rob followed them into the condo where Ricky and Kenny greeted all of the girls as well.
By no means was Rob a heavy drinker. Ricky and Rob had been to enough parties together to know their way around alcohol. Ricky usually went a little crazy but it was nothing too out of control. Each of the teenagers now had a bottle of something whether alcoholic or not and some food. They sat in a circle, chatting about how their breaks were going so far. After awhile things got quiet and Rob and Ricky caught eyes for a moment, sharing a look for a moment before Rob realized they had to move this party along.
“So, what now?” Rob asked awkwardly. There was a pause as various ideas were thrown out from trying to find something in town to cards.
“Truth or dare Ricky?” the question halted all other conversations. Eyes gazed first at Anna, who had asked the question and then to Ricky. Rob shared the same look he had before with Ricky. Had he and Anna planned all this out? Had they played before without him knowing?
“Dare!” Ricky responded defiantly.
“Strip down to your pretty little boxers then,” Anna told him. Ricky rose and tore off his shirt.
“Wait, you’re really gonna do that?” Lexi asked, stunned.
“Yeah, a dare’s a dare,” Ricky responded as he undid the belt on his jeans.
“Now this is a game!” Rob said, cheering on Ricky to finish his strip as the others laughed along. Seconds later Ricky was standing in nothing more than some red and blue checkered boxers with the slightest hint of a semi-erect cock against the fabric. Ricky was a rather skinny kid, being just taller than Rob and a lot taller than Kenny. He was toned with muscle though from being on the swim team with Rob. His skinny legs, like Rob’s, had very little hair on them as they were just growing back from a swim meet they had competed in. Nobody else seemed to notice but Rob wondered what the girls would think of their boyish legs. Ricky quickly sat back down in his seat and continued the game.
“Tasha, truth or dare?”
“Truth,” she responded happily.
“Are you a virgin?”
“No,” she stated without any big fuss, and then she turned to her right over at Lexi.
“Truth or dare Lexi?”
“I’ll take truth too,” Lexi responded. Rob figured that nobody was brave enough to take dare after Anna had Ricky strip next to nude on the first dare. Nobody wanted to join him in his state of undress.
“Do you shave your pubic hair?” Tasha asked.
“Uhm, well, I have before and it is right now,” Lexi responded, blushing slightly at such a personal question. She gave Rob a quick glance which he caught and responded with a small quirky smile. She quickly turned away and moved along the game.
“Kenny, truth or dare?” she asked.
“Truth please.”
“Has anyone besides your parents ever seen you… naked?” Lexi asked, giggling a bit.
“Nope, nobody,” Kenny responded easily.
“Truth or dare Rob?”
“Dare,” he said and everybody held their breath in anticipation for the next dare.
“I don’t really know anything good,” Kenny said, shaking his head and laughing a little bit. He didn’t want to seem weird giving Rob a dare like the one Anna gave to Ricky. He had been a little nervous this whole game, and Rob’s desire for a dare wasn’t helping.
“Just give me whatever, I don’t care,” Rob said, trying to reassure his friend.
“Then I dare you to just, uhh, take your pants off I guess,” Kenny suggested nervously. Rob rose and dropped his shorts quickly, standing in his t-shirt and black boxer-briefs for a moment, showing off the tight undergarments, before sitting back down and continuing.
“Ok, so Anna, truth or dare?” Rob asked.
“I’ll have to take dare.”
“Ok, then let’s keep with the theme here. I dare you to strip down to your underwear too.” Anna nodded and got up quickly. Quickly pulling her shirt up and over her head easily and unbuttoning her skirt in one fluid motion so she stood in just her pink thong and bra. She spun around for the group once as Ricky wolf-whistled and Rob clapped. Then she sat back down.
“Ok, now it’s time to spice this game up a bit,” Anna suggested.

[Hunterman36]

Ok ok ok I like it so far keep it up

[Nick]

Day 3.3: Dared

“Alright,” Anna said. “Truth or dare Rob?”
“Truth,” he stated, smiling slyly.
“You suck!” Anna yelled and everyone laughed. She obviously wanted to dare him. “Okay, then how big is your erect penis?”
“Seven and a half inches,” he told the group with ease. He didn’t make direct eye contact with anyone, not wanting to know what they were thinking. But he turned to Lexi after a few seconds to continue the game.
“Truth or dare?” he asked her.
“Dare,” she said, getting into the game. Rob thought for a minute.
“I dare you to take off your t-shirt and bra. Go to the kitchen and use the whipped cream to cover your breasts.”
“Okay,” Lexi said with a slight stutter. She got up and took of her shirt and revealing her dark blue bra. Then she turned away from the group to take that off. The fabric fell to the ground and Lexi covered her chest on her way to the kitchen, never facing the group to expose herself. It was hard to see over the counters and into the kitchen so Lexi disappeared for a moment. A minute later she appeared in the hallway again with just enough whipped cream to cover her nipples and not much more of her breasts. Lexi looked great. She didn’t have as big of breats as Anna and Tasha but she was still well developed, skinny and overall very pretty. She sat down confidently with care, careful not to make the cream fall from her breasts to expose her. But after sitting, she was ready to get right back into the game.
“Truth or dare Ricky?” she asked.
“Truth.” There was a pause as Lexi thought of a question.
“Alright, how many people have you fantasized about in this room?”
“Uhhh, three,” he told the group, smiling lazily. “Tasha, truth or dare?”
“Dare.”
“Ok,” Ricky said, thinking. “Give Kenny a lap dance.” Tasha looked a little annoyed at first with her dare, eyeing up Kenny.
“Uhm, what?” Kenny asked, a little confused.
“Just go along with it!” Rob told him and so Tasha climbed over to Kenny and started. Tasha seemed to know what she was doing, getting very close and personal with Kenny who didn’t dare seem to move. In Tasha’s short skirt Rob figured her panties were rubbing right against Kenny’s jeans. After another minute Ricky told Tasha to stop who moved away slowly. There was a new bulge in Kenny’s shorts now.
Before Tasha called out her next victim Anna crawled over to Tasha and whispered something in her ear. She smiled and whispered back, nodding her head. Everybody else wondered what was going on now.
“I have a good dare,” Tasha began, looking around at each person. “But all the boys have to do it together.”
“As long as it’s not something too sexual,” Kenny said.
“And we get to give all the girls a dare to do after ours!” Rob suggested.
“Alright,” Anna said, agreeing to both of the terms. Then she motioned to Tasha to give out their dare. Rob was excited; it was going to be a pretty good dare if she wanted all the guys to do it.
“Ok, I dare all of you to jump into the pool naked,” Tasha told them.
“No!” Kenny immediately protested.
“Don’t be a spoil sport,” Lexi told him. Rob and Ricky were already up, heading for the pool, ready to do the dare. Kenny and the girls followed behind and with a little more nagging Kenny agreed to the dare. It wasn’t anything too bad but he must not have wanted to be seen naked. Rob took off his shirt, throwing it back to the living room and joined Ricky who was already at the edge of the pool. Kenny lined up next to them after taking off his shorts and shirt, standing next to them in his green boxers. The girls counted up for them and on three the guys ripped down their underwear and leaped into the pool together, the collective splash was large enough to even get the girls somewhat wet. The water was crystal clear and once the waves calmed Kenny immediately covered up under the water, not trying to expose himself at all.
“Alright, we dare you gals to do the same,” Ricky said. The girls looked at each other uneasily. They had given the boys a little modesty by staying behind them when they jumped in but now the guys were all gazing eagerly at the girls to get naked for them. So the girls turned their backs to the guys as they undressed. Lexi took a towel that was lying on the ground to wipe off her breasts. Anna was the first naked, her tanned back was beautiful and toned, tan lines around her firm butt. The others were naked as well and on three, they all turned around quickly and jumped in the pool too, covering themselves as they went.
Now that they were all in the pool the gang laughed together and splashed around like good friends. Even Kenny was enjoying himself swimming around freely. After a few minutes, Anna swam over to Rob and they smiled at each other. Then, suddenly, her hand grabbed his cock and she started to work up and down on the shaft. He was confused at first but it was so sudden and it felt so good, Rob grabbed onto one of her large tanned breasts and felt it. She must have tanned topless. Then Ricky suddenly splashed the pair, not noticing what was going on. They broke apart, Rob was suddenly embarrassed for what was going on but Anna seemed to be enjoying herself. Once Rob’s cock calmed down he was the first to get out of the water, not bothering to cover up his semi-hard penis, which was also bald since he had shaved it before the trip, as he walked back into the condo to dry off. He came out wrapped in a towel and watched as the others got out.
Anna was next to get out, her pubes were shaved as well and she gave Rob a wink as she walked past and into a bathroom. Lexi and Tasha came next. Lexi was bare as well and Tasha trimmed. They both asked Rob where they could get towels and he pointed to the nearest bathroom. Ricky was next, with very short trimmed pubic hair that Rob had seen before in the locker room. He didn’t bother drying off and just decided to sit down on a chair, clutching his boxers in one hand. Kenny was last, walking swiftly to his room to get clothes, covering up with his underwear.
After the group got back in the same room the guys offered to let the girls stay here for the night. They happily agreed and discussed that they should continue the game tomorrow or at least some other time. Tasha took the spare bedroom that wasn’t in use and Rob offered his room to Lexi and Anna. Lexi stated she was happy just sleeping on a couch so Anna took his room. That left Rob with the other couch which he was fine with. After gathering blankets and pillows for the two people left without beds, the group all wished each other goodnight and went to their respective sleeping areas before drifting off to a happy sleep.

[Hunterman36]

Great great great it was a great entertaining post can't wait for the next keep up the great work