Family Trip to Jamaica Pt. 03

"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. Pretty soon, a girl about my age caught my attention. She seemed to be with her family as well, and was standing casually, chatting with her father while sipping on a colorful drink.

She was about 5'0" tall, with black skin, afro'd hair that was pulled back to reveal a gorgeous face. Her lips were plump, and her nose stood out as longer than average (I like a good, healthy nose). Despite her short stature, she was stacked. Her breasts stood out, almost a D cup I would assume, with small, dark nipples. When she moved, her breasts swayed from their own weight in a mesmerizing way. Her stomach was toned and flat, but still thick somehow. I think this is what people mean by "slim thick." Her ass, while smaller than my sister's, was healthy and toned as well. Kind of reminded me of my mothers ass. Did I just think that? My god, whats happening? The girl seemed like the most important, delicious thing in the world at that moment. I was instantly sucked in. It was amazing that her father could stand there, both completely nude, and not have a hard on with a daughter like that. I watched her apply sunscreen to her body, making her tits move and sway, and her skin shine in the sun.

"She's cute, and what a rack!" I heard my mom's voice from above my head. "Are these drinks up for grabs?" As she said this, my mom moved from behind the lounge chair to stand in front of me.

I nearly spit out my margarita. My mom seemed to glow with the sparking ocean water behind her. She had on a lime green bikini that was so small I felt like I could see all but the most intimate bits of her. Two small triangles covered what seemed like just beyond her nipples and the strings from each went up and met around the back of her neck in a bow. Her bottoms were equally tiny. The bathing suit lay flat against her pussy, and I could see the ocean between her slender thighs. As she sat on a lounge I caught a glimpse of her ass. This was no ordinary bikini. The string disappeared between her toned ass cheeks. Sitting in the sun, just like Lily, my mom's red hair and pale skin shined bright. I reflexively put up a knee to hide my growing erection.

"Mom, did you own that suit?" I couldn't believe she had this hiding in her closet (my friends would have found it by now, I'm sure).

"No. All the suits I had felt too frumpy all of a sudden. I found this in the gift shop and figured it would help me fit in better. Is it ok? Does it look nice sweetie?"

Something about the mix of the intense sexuality of her bathing suit and her maternal use of the word "sweetie" was too much and I had to change the topic before I erupted.

"Where's dad?"

"Your dad is going to spend all day at the bar, I'm sure. He's better now, but some rum will help him recuperate from the shock of this place." As she explained this, my mom knocked back two of the shots, and started sipping on the margarita. "Ooo that's nice sweetie. Thank you for ordering it."

I looked back and sure enough, Dad was sitting at the swim up bar at the pool, drink in hand. He was talking to the guy who had been on the shuttle with us with his daughter when we first got here.

We spent the afternoon lounging on the beach. My mom stayed under the umbrella for the most part, afraid her fair skin would burn too easily. Every now and then, Lily would come back and apply some sunscreen (watching her lotion her ass was enough to make me temporarily distract from staring at my Nubian goddess) before running out again to talk to some of the boys on the beach. We ordered drink after drink, and more snacks every now and then. It was fun just hanging out with mom and drinking. When we went on vacation in the states, I was usually left to fend for myself when my parents were drinking, but here I felt like more as an equal. Mom chatted about her work and friends and the continuous stream of alcohol and sunshine began to loosen our inhibitions.

"Jason honey, can you put some sunscreen on me please? I don't want to burn and ruin the rest of our vacation." My mom was laying on her belly in the lounger, and lazily reached back to hand me a bottle of sunscreen. "Really rub it in honey."

"Um yea, no problem." I squirted some in my hands and started at her shoulders. Although she is so slender, her shoulders were surprisingly strong. Her gymnast background really did still come through. I worked my way down her bare back and realized, to my horror and delight, that there was a big issue. I was approaching her sexy, firm, ass. The ass covered by nothing but a tiny string. Even from this close, I couldn't see where it disappeared to. I got my answer when my mom felt me getting lower and suddenly relaxed her legs a bit. They split apart just enough for me to see the string passing over her asshole and broadening into the thicker fabric right before I would get a glimpse of her pussy. Boozy urges threatened to take over as I wanted so badly to bury my face in her ass and to rip her thong off with my teeth. My poor mom. If she knew what her request was doing to her boy, she'd feel so guilty.

I had to calm down. I skipped over her ass and moved to her legs, thinking I could get away with it. My mom didn't flinch and I continued rubbing her down. While Lily's body seemed to be built for fun, with her PAWG ass and healthy sized tits; mom's body exuded strength and grace. As I massaged the lotion into her legs, I kept my eyes on the fabric over her mound and imagined the treasures beneath. I was too horny to care that I was lusting over my mother. In my head I justified it a bit as just an enjoyable view, and I would take that sexual energy elsewhere.

As soon as I was finished with her feet, my mom felt me start to get up and gave a "tsk tsk." I looked at her face to see a smile. "You missed a spot, and I definitely cant have that burn," She said this as she wiggled her ass in the air. My mom, who worked full time, while simultaneously always being the mom who brought the cookies to parent-school conferences, was wiggling her ass at me. Resort magic, I thought to myself again. Without a word, I dutifully rubbed lotion in her ass. It was so firm and gorgeous. I could have spent all day there. I wanted to take a bite, but I forced myself to finish and quickly get back to my chair before she noticed my hard on.

"Thank you. That was nice." She flipped over and did her front side herself.

We chatted for a while longer and eventually my mom asked me about my relationships.

Looking over at the girl with the massive breasts I was lusting over, my mom suddenly asked "What happened with you and your last girlfriend, Sarah? She was such a nice girl. And very sexy too."

I was too buzzed to be overly shocked by my mom's definition of my ex as sexy at this point. "She just moved and it was too hard to keep things up. We just bickered a lot toward the end. Also I wasn't getting everything I needed from her," I said, looking over at the naked girl.

"I'm sorry, Jason. Relationships are hard work. You'll be OK. A handsome boy like you. Look how you've grown into such a man." As she said this, she scanned me over and I could have sworn she emphasized "man" when looking at the slightly obvious bulge in my board shorts. I assume the alcohol was taking effect, because her eyes linger and she didn't speak for longer than you would expect mid-conversation. "You know, your father and I went through rough times. But now we really support each other."

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. I 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."