Island Vacation by Mr.Lover420

As he came out of his bedroom he saw his younger sister, by a year and a half, still in her pajamas on the couch watching tv. Jennifer, or Jen as she liked to be called, was about 5’1 100 pounds. She was a cheerleader for their high school and was a flyer because of her small size. She had decent tits a good B cup and a tight little ass. With long blonde hair and dark green eyes all of the older boys wanted her but they knew better than to try because of her older brother.

As Jason was getting ready to leave he snuck up and scared his little sister by tickling her. When she jumped and tried to get away he noticed she was only wearing a long tshirt and nothing else. He had seen her naked before, his parents never much cared about modesty in the home, but seeing her young little pussy up close and slightly spread surprised him.

“You’re such a jerk!” Jen yelled and threw a couch pillow at her brother.

“Yup” was all Jason said back and threw it back at her as he left the house.

Jason was hanging with some friends when he got a text from his dad.

“Need you home for dinner. There’s some stuff your mom and I want to discuss with you and your sister.”

Jason knew it was about his parents yearly trip to his dad’s bosses private island. His parents have gone every summer since his dad became a board member for the company about ten years ago. They were usually gone two weeks and Jason and his sister usually stayed with friends. Jason wanted to stay home this time, he was old enough now and Jen wasn’t hard to watch.

After dinner was cleaned up their parents asked them to wait in the living room. Their parents took a few minutes to come into the living room and when they did both kids looked shocked. Jason and Jens mom, Amber, was wearing a red see through negligee. Amber was 40 with blonde hair just passed her shoulders and brown eyes. She had a beautiful face. She had big DD tits that sagged a little without support but we’re still pretty firm. She had a slight pudge in her middle but no one would ever say she was even chubby. She had wide hips and a decent size ass with just a little cellulite on it. It always swayed and jiggled a little when she wore anything other than jeans. Both kids also noticed their mom was completely smooth everywhere.

Dad was Hank. He’s 42 and his dark hair was receding a little but was very handsome. He wore a short goatee and also had piercing blue eyes. He had a stocky build at 6ft even and about 230 pounds. He had a bit of a beer belly on him but he also had a lot of muscle. Hank was wearing a pair of silk shorts that barely covered the bulge inside.

They’d seen their parents in very little before, but this was somehow different. They were dressed to be sexy. And they were.

Jen was the first to speak, “Wow! You guys are hot! But why are you dressed like that?”

“Well hun we wanted to talk to you about our annual trip to the island.” Amber started out. But Jason quickly interrupted.

“Don’t tell me we have to go stay with someone while you’re gone. We’re old enough to not need a babysitter anymore.”

“Don’t interrupt your mother.” Hank said as he motioned for his son to be quiet.

“Well that’s one of the things we wanted to talk to you about.” Amber continued. “You’re right. You’re both old enough now and just going off your reactions to your father and I, you’re both mature enough now too.”

“Oh thank god.” Jason said out loud.

His dad scowled at him and he quieted down.

“You’re both ready but not to stay home while we’re gone. You’re both ready to join us.” Amber informed them. She was smiling but looked nervous.

“What do you mean by going off our reaction to you?” Jen asked for the both of them.

Hank spoke up, “Well you know the island is owned by my boss. But not everyone from the company gets to go. In fact out of the hundreds of employees only about 50 get to go. That’s because it’s more than just a little vacation. It’s an adult themed resort.”

“I’m confused,” Jason said, and Jen shook her head in agreement.

“The island is where certain employees and their families go once a year to engage in whatever adult activities they want. Whether it’s something taboo or group oriented or just watching.” Hank was trying to make it sound innocent but knew he wasn’t doing a good job.

“So it’s a place where you go to have sex?” Jen asked accusingly.

“Well yes but it’s more than just sex. It’s a freeing experience. You can wear as much or as little as you’d like. You can do things you’d never do here at home without any judgement. And yes there is a lot of sex. But you never have to do anything you don’t want to. That rule is written in stone and breaking that rule is very harshly dealt with.”

“So you want us to go to this island with you and just have a bunch of sex?” Jason asked more rudely than he meant to.

“No we want you to come and enjoy a place where there’s no judgement and you can just let loose. No one says you have to do anything with anyone while you’re there.” Amber was doing a much better job explaining it than her husband. “We wanted you to see us like this because if you decide to go you will see us naked, a lot, and most likely having sex with each other and other people. We wanted to make sure you could handle it.”

Jen was smiling ear to ear, “I can’t wait to go with you guys.” She exclaimed.

“It does sound fun.” Jason admitted.

“Oh I’m so glad to hear that.” Amber was beaming with excitement.

“Now it’s time for some honesty,” Hank said, “there’s no wrong answers, the only wrong answer is a lie. Jason are you a virgin?”

“Umm umm ya.” Jason said as he slumped his head down in embarrassment.

“There’s nothing to be ashamed of son. I’m only asking so we can get you prepared for trip.” Hank tried to ease his son’s embarrassment.

“What about you Jen?” Hank asked.

“Well umm no I’m not.” She answered and everyone looked at her in surprise. “I only did it once and it hurt and was over really fast. It wasn’t very fun.” She said trying to defend herself.

“No need to get defensive, you’re practically in the same boat as your brother.” Hank said reassuringly.

“I think the two of you need some practice before we leave. We can’t have our kids not knowing what they’re doing at the island. Not with our last name.” Hank chuckled and Amber giggled while the kids looked very confused.

“Why don’t you both go upstairs and put on something more comfortable and maybe a little more revealing?” Their mom asked.

The went upstairs and we’re back down in a flash. Their parents were now completely naked and Amber was on her knees with Hanks cock in her mouth.

“Woah! I wasn’t expecting that!” Jen said watching her mom bob up and down on her dads cock.

Jason was right behind her, “Expecting what? Wow!” Was all he could get out.

Jen was wearing a thin tshirt that went just below her ass. It was obvious she wasn’t wearing anything underneath.

Jason just threw on a pair of basketball shorts, and judging by the bulge growing that’s all he was wearing.

“Now remember this only goes as far as you’re comfortable with. There’s no judgment and that goes both ways. There’s no judgment for what you don’t want to do and there’s no judgment for what you do want to do.” Hank talked to the kids while Amber continued to blow him.

“Ok so what do we do?” Jason asked.

“Since you’re both pretty inexperienced let’s start off slow.” Hank said pulling his wife up. As Amber moved off of Hanks cock, Jen gasped at the sight . Her dads cock was big. At least eight inches and really thick. “Jen come sit on the love seat with me, and Jason you and mom take the couch.”

As Hank and Jen sat down her breathing was beginning to speed up.

“Remember hun we don’t have to do anything you don’t want. Even if that means we do nothing.” Hank meant what he said.

“That’s not it daddy. I really want to, but you’re my dad. It just feels weird.” Jen wasn’t completely sure but her wet pussy was telling her otherwise.

“If it helps just pretend I’m not your dad right now. Close your eyes and tell me when to stop.”

Jen closed her eyes as Hank ran his hand up her legs to her inner thigh. When she didn’t protest he went up a little further until he was just shy of her young pussy.

“Are you ok?” He asked lovingly.

Jen shook her head yes and spread her legs a little to allow her dad easier access to her. Hank slid his hand to his daughters pussy and began slowly rubbing her lips and clit. He reached around her with his other hand and began feeling her tits through her shirt.

Jen was soaking wet now and breathing hard. Hank leaned in and kissed her, not a fatherly kiss but one that sent shockwaves to her pussy.

On the couch Amber had taken off Jason’s shorts and was stroking her sons cock while he played with her huge tits.

“I see you take after your father.” Amber said while stroking Jason’s cock. He wasn’t quite as big but he was close at about seven inches and almost as thick as his dad.

Amber leaned down and took him into her mouth.

“Holy… wow mom! That feels amazing!”

Amber began deep throating her son. Jason threw his head back and when he looked to the side he noticed he had a great view of his moms big ass. He reached over and started rubbing her wet pussy. This drove Amber to suck harder and Jason knew he would cum soon.

“Slow down mom. I’m gonna cum!” Jason tried warning his mom but she didn’t let up.

“Aahhh ahhh oh shit I’m cumming mom!” Jason began shooting his load down his moms throat and she swallowed every last drop. When she came up she stuck her tongue out to show him she’d swallowed it all.

“Well now that the first ones out of the way, I think we can have some fun.” Amber said to her son as she layed down on the couch and spread her legs wide open.

“I want you to eat my pussy until you’re hard again son.” Amber was fingering herself as Jason got into position.

Hank now had Jens shirt off and was sucking her nipples while he fucked her with two fingers. She was moaning in pleasure and he knew she’d be cumming soon. Hank grabbed her hand and led it to his cock. She instinctually started to stroke it. As she jacked off her dad she began cumming on his hand.

“Uuhhh uuhhh uuhhh oh god, oh daddy don’t stop I’m cumming. Oh god daddy uuhhh uuhhh it feels so gooooood!” Jen was shaking a little, but never stopped stroking her dads cock.

“Do you want to suck on it hun?” Hank asked his daughter.

“I really do but I don’t know what I’m doing.” Jen answered with her dads cock still in her hand.

“Hey babe, will you come over here and help Jen out?”

Amber stopped her son from eating her pussy, which she needed a brake anyway, she had cum three times from her sons tongue.

Amber knelt down alongside her daughter and showed her how to give a blow job.

As Jen was sucking her dads cock she couldn’t believe how wet she was getting.

Amber noticed too and positioned herself under her daughter.

“Is this ok hun?” Amber wanted to make sure her daughter was comfortable with everything.

Jen shook her head yes with her dads cock still in her mouth. As soon as Ambers tongue touched Jens clit she let out a moan. Within minutes Jen was cumming on her moms face. Amber kept eating her daughters pussy, licking her virgin asshole occasionally.

Jason was rock hard again and knelt down between his moms legs.

“Mom. Can I fuck you? I want you to take my virginity.” Jason was so aroused by the sight of his little sister sucking their dads cock while their mom ate her pussy.

“God yes son. Do whatever you want to me.” Amber answered before going back to her daughters pussy.

Jason eased his cock into his moms wet pussy. It was the greatest thing he’s ever felt. He began pumping in and out of her. Amber was now moaning into Jens pussy.

Jason began fucking his mom hard and fast, and she knew it wouldn’t take long for him to cum. When she felt him tense up she clenched the walls of her pussy tight around his cock and he exploded inside her.

The sight of his son filling his wife with cum was too much for Hank. He pulled his cock out of his daughters mouth and came all over her neck and tits. Amber jumped up and licked off as much of her husbands cum from her daughter as possible and then gave her a long slow cum filled kiss.

“So this is what we have to look forward to at the island?” Jen asked still out of breath.

“This and a whole lot more if you want it.” Her dad replies.

“We don’t leave for a couple more weeks. If you want we can get some practice in everyday until then so you’re good and ready for the real fun.” Amber said to her kids while she was rubbing her pussy.

Jason and Jen both replied with an enthusiastic “Yes please!”