Family Trip to Jamaica Part 3

“Hi kids! How was the class?” My mom was as cheerful as ever.

All I could do was blush, but Lily came to the rescue, “It was great. Seeing everyone do a normal activity like painting while nude made us a lot more comfortable with being at the resort.” Phew. I don’t know what I expected her to say, but I’m glad she just kept it to that. She almost sounded like she was playing it up to make my mom feel better.

Lily then turned her attention to dad and added, “Jason even volunteered to be the nude model we all used to paint from. Just standing up there with hard on to demonstrate strength and vigor.” She said it so casually, but the way she was directing it towards dad, I know she was trying to get a rise out of him. She’s insane.

After a short pause, dad barely flinched and said “Oh, well that’s nice darling. Jason, did you have a good time?”

Well that was surprising. Lily seemed annoyed that she couldn’t get dad to react. I was just shocked he was taking it so well.

“Umm, yea it was kind of fun. It wasn’t so bad to be naked since no one else was making it a big deal. And Lily really helped make me feel comfortable too.” There was so much in there I didn’t say. Like the fact that it wasn’t only “not so bad” but incredibly arousing to be naked with others. And also the small fact that my sister unintentionally jerked me off.

“That’s great. I know I was a little worried about everything when we first got here, but hearing that makes me feel better. And your mom spent a lot of time convincing me to relax too while you guys were in the class.”

For some reason, my mom was blushing, and shifted on the couch. “Oh, honey. It was nothing. I’m glad everyone is feeling better. Should we brave the beach and get some drinks?”

“I’m game,” Lily chimed in. “Jason, are you going to be wearing a suit, or embracing your newfound naturist lifestyle?”

“Ha ha, very funny.” I was not amused. But what came next I can only assume is the mysterious effect that this resort has had on everyone to loosen inhibitions.

My dad looked at us both. “You might have been joking with your brother darling, but actually I want you two to know its OK. Your mom and I talked about it and decided that this is part of what we meant by giving you freedom.” His face suddenly turned professorial the way it does when he wants to teach a big life lesson. “You see, for young folks like yourself, its important to test the boundaries….”

Mom swooped in as quickly as she could, “Ok, honey. We don’t have a half hour to spare for a lecture on the philosophies of freedom and choice. Bottom line is. Want to be naked? Go for it. And as a heads up, your dad and I will probably be taking advantage of this freedom as well, so don’t be shocked it you see us suddenly in the buff! It’s something we have wanted to try anyway. Understand?”

I couldn’t believe what I was hearing. It was enough that my parents were giving the green light to let me explore the growing exhibitionist in me, but they’d be doing the same! I had resisted sexualizing my mom, but of course couldn’t stop myself from peaking at her over the years. Especially with my friends’ relentless efforts to try to see her undressed over the years, and their recent tendency to go into graphic detail of what they would do to her if they had the chance. I’d protest, but weakly as I secretly enjoyed the attention she got. Thats right, I’d think, my mom is a MILF. I’m pretty sure my mom was aware of my her reputation, because she would play dumb and announce how pairs of her underwear seem to go missing each time my friends were over.

I side glanced Lily to see her reaction to my parent’s decision, but she was playing it cool.

“Very progressive of you guys. Dad, are you really OK with seeing your little ones naked?” There was something almost babydoll coquettish in the way Lily was talking to dad. Mom noticed too, and gave a knowing smile.

Dad blushed a little, adjusted his shorts, and said “Yes its fine. Like I said, your mom made some really convincing arguments for it. Besides. It’s a choice. You don’t have to if you don’t want to. Now, your mom and I are going to get changed. You and your brother go get a spot down at the beach. We’ll meet you there. And easy on the booze. I can smell the rum on your breath from here Lily.”

——–

We headed out to the beach, passing a pool full of nude swimmers. Again, it was shocking to see how few people took the option of keeping their clothes on. Lily and I got the most stares as we were one of the few clothed ones. Though Lily could draw plenty of attention even not naked. Her pale skin and red hair always made her a lightning rod for attention. She had chosen to wear the one piece bikini she modeled in the store for me, and I couldn’t help glancing at her ass as it moved when she walked and at the valley between her nearly exposed tits that I had pooled with my cum earlier.

“Hey, its the stud from earlier!” someone called out. I recognized it as the guy in class who was doing more stroking than painting. I waved, not knowing what else to do.

“Ha. Not exactly the island babe you were looking for I assume. But you seem to enjoy the attention.”

In such a short time this resort had helped me feel closer to her and like I can be more open. What’s the point of keeping secrets from someone whose had your cum on their chin, right?

“Honestly, I think I really do. It’s nice to be noticed and desired. Even from him.” I waved again to my admirer.

The beach, much like the pool, was speckled with beautiful (some less so) bodies, glistening with sweat from the pleasant heat. The water looked inviting. Shining shades of blue as far as you could see. The resort was set far enough away from any other place that it made the beach feel more exclusive and private. It wasn’t overwhelmed with tourists and peddlers selling cheap junk Like places we have been to in the past. As soon as our feet touched the sand, a young hotel employee named Sean, who couldn’t be more than 15, rushed over to assist. He helpfully offered to have us brought some chairs and an umbrella, as well as any drinks or food we might want. We ordered some salads and sandwiches, realizing how hungry we were. And of course, this being vacation, I ordered 4 margaritas and 4 shots of rum. Lily looked over at me disapprovingly.

“What? It’s vacation and Im embracing the freedom. Plus relax, some of those are for mom and dad.” We found our spot and waved over to Sean who quickly brought us our chairs and umbrella Soon followed another employee with drinks. Lily decided to go down to the water, but I chose to hang back and relax. Really, I wanted a chance to see if there was anyone I would want to flirt with. All over the beach people lazed, sunned, or played in the water. Dad’s repeated mantra of “freedom” really started to make sense. I felt so relaxed. Still as horny as ever, but unlike at home, there was a missing tension. Resort magic again, I guess.