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Family Trip To Jamaica - S01 E09

Story 1 year ago

Family Trip To Jamaica - S01 E09

Read Story: SEASON 1 EPISODE 9

They really love each other. It was a nice feeling to still see that in them. 'I noticed. He was having a hard time before and you must have said something right, because he seemed totally fine when Lily and I came back."

"Oh, hun. That's easy. My mom started chuckling a bit. "I did what I always do when your dad needs some convincing or cheering up. I sucked and fucked him until all the worries just cum right out of him." And with that she burst out laughing. Did she just say what I think she said? With all the laughing, I couldn't tell if she was joking or serious. Either way, my dick lurched to attention at the thought of my mom on her knees, draining my father. I knew I heard moaning before!

"Mom! Are you serious?"

"Of course dear. When he was good and tired, I just reminded him of all the good that might come from letting you two enjoy your time." We both looked over at Lily at the same time for some reason. Lily was laughing and flirting with a tall and very naked young man. My mom chastised me, "Oh Jason, don't be such a prude. Your mom and dad have a healthy sex life and you should be proud. Plus," she said while gesturing to her body, "wouldn't you be convinced of anything if you had this. Again, she bent over laughing. She could really crack herself up. My mind was too blown to enjoy the sight of the string up her ass when she was bent over laughing like that. Yes, I eventually thought. She could convince me to do anything.

"Anyway, I'm going to go rescue that nice man from your father and make him get in the pool with me. Go find your sister. Better yet, go find a girl!" And with that she left, laughing to herself.

Sadly, the girl I was hoping for was gone. I sat for a while longer, confused and horny, when finally Lily came up. To my surprise, she wasn't with the boy she was talking with before, but with a cute girl.

"Jason, this is Jane. She's form Brazil and here with her guy cousins. She was getting bored so I thought she should meet you."

Jane was about 5'4", with brown, shoulder length hair, blue eyes,

tan skin and an inviting smile. Much like everyone else, she was completely nude and unashamed standing in front of me. Her pussy was shaved completely, giving me a full view of her sandy slit. She had a tiny bit of a belly, and round, full tits. Her figure reminded me of what in the past they advertised as the ideal figure of women. A soft and supple body.

I invited her to sit down, and got her a drink. To my surprise, Lily stayed. I expected her to go back to her boys. I shot her a look, but she only winked back at me. We all made small talk and I tried hard not to just oggle Jane's body the whole time. Jane's accent was incredibly sexy, as was the way she laughed at all my dumb jokes. Lily laughed along and kept the drinks flowing. Eventually, talk turned to the resort and nudity.

"I've been coming here for years with my family. We always find the best naturist friendly places," I asked her what she thought about being so open and free with her family. Jane smiled that smile people get when you say something naive and said "my family has always been close. We actually spend a lot of time without clothes in our home in Brazil. It's been that way since I was young and I never felt self conscious about it."

The way she described it was wonderful. don't know if it's my years of porn or the fact that I don't live in nudist community, but it was hard for me to separate being nude and sex

"That's so beautiful Jane," Lily said. "I want to enjoy the freedom, but I have to say, being around all these bodies does really make me want to grab the closest penis and go to town."

Jane laughed. "Oh, there are definitely times when I can't help myself. But you two should try being nude while you are here. See if you can enjoy. And with that she put her hand on my leg and looked at me encouragingly.

"Sure, let's give it a try.' Lily said. And with that, she stood up and removed her top to unleash her beautiful tits. Several men around us turned to look, as if this is what they had been waiting for. Jane looked on approvingly and then turned to me.

"What about you?"

"I don't know." I could tell she was interested, and I realized that Lily was fulfilling her promise to be a great wingman for me. Jane was right there, and if I went along, I'd probably be able to seal the deal tonight. But the butterflies kicked in, and seeing Lily's tits again made me feel guilty for what happened before. 'Im actually pretty tired. We just got in today and I've had a lot of sun. I'll see

you around." And with that I got up and left. I could tell I screwed

up royally by the look on Jane's face. I could hear Lily trying to make excuses for me, but I moved quickly. As I walked past the pool, I saw my mom and dad, practically intertwined as he carried her around the water with his hands on her ass.

I stretched out in the bed and beat myself up for screwing up a sure thing once again. I barely heard the door open, and soon Lily was sitting on the bed, still topless, looking at me with a sad expression.

"You know you fucked that up right?"

"I know. I told you, this always happens. I get in my head and it all falls apart.

"Well, I told you I would be your wingman, and I'm about to show you the lengths I'm willing to go to help out my little bro. Jane?"

I looked up, and in walked Jane from the living room. They had come back together. Lily explained," I told Jane about your little problem and she thought it was really cute. She wants to help you."

Jane had such a sweet and affectionate expression. She said, "Your sister really cares for you. She reminds me of how we look out for each other in my family. I have two brothers, and we've helped each other grow sexually over the years. I couldn't imagine growing up without them." I started to speak, but she lay next to me and began to kiss me.

Lily looked on. "I think she wants you to shut up before you fuck it up again. Just let us help you, little perv." There was that phrase again - "little perv - it was so arousing. And her use of the word "us" did register before I felt Jane's tongue snake into my mouth.

We kissed passionately and I explored her curvy body. Her skin was smooth and her tits felt full and perfect in the palm of my hand. She lifted her body up, while pushing me down, and began to remove my shorts. My dick sprung into the air and she looked at it hungrily. "Mmm, you were right Lily. So big. How dare you hide this from me. She bent down and I felt the tip of her tongue trace the shaft of my dick from tip to base and back up again. My hips bucked as my dick begged to enter her mouth. She smiled and continued to tease me, at times just letting her breath excite my member. I looked over and noticed that Lily had moved to the other bed. As she watched us, I could see her hand had moved under her bikini and was moving rapidly, while the other hand was circling her nipple.

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Family Trip To Jamaica - S01 E08

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Family Trip To Jamaica - S01 E10

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