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Family Trip To Jamaica - S01 E22

Story 1 year ago

Family Trip To Jamaica - S01 E22

Read Story: SEASON 1 EPISODE 22

"Oh, I see Mr. Grown Man. I'm glad you are really embracing this freedom to drink." Mom signaled to the beach boy and ordered some food and some more margaritas. We sat in the shade and enjoyed the beach while sipping the strong cool drinks. I did my best, of course, to reign in my peaking as much as possible.

Eventually I grew more comfortable, or more buzzed, and relaxed. From one corner of the beach near the resort we heard the bass sounds of club music and looked over to notice some people had gathered. "What do you think that is?" I asked.

My mom looked slightly disinterested, "I'm not sure. But it looks like a lot of young people. Why don't you check it out? It'd be good for you to see people your age feeling comfortable." Out of politeness, I asked if she would be coming, but she said no, as she preferred to just relax.

I stood up, thankful my erection had gone down, and headed toward the noise. It'd be helpful to get away from mom for a little bit. Maybe she was able to be comfortable with nudity so quickly, but to me it still, at least with her, seemed to signal sex. What am I thinking? I'm admitting to myself more openly that I couldn't stop thinking about my mother in a sexual way. I really did need some time apart.

As I approached the crowd, I noticed they were standing around a stage and seemed to be waiting for a show to start. I stood around and helped myself to one of the drinks the hotel staff were passing around. Suddenly, I felt a tap on my shoulder, and turned to see Paul, the coordinator from the art class.

"Hi, Jason right? Oh thank goodness. Listen we are looking for some people to play a little game on stage. It's going to be recorded for an ad for the resort, so we are trying to find some people who would look good and presentable. You were so helpful stepping in for the model before, and I already know you look good. Would you mind?"

I was a little lost. "Ummm, sure I guess. What's the contest?"

Paul laughed, "Oh it's nothing. It's a silly little game where we pit couples against each other. Is your girlfriend here?"

Again I was lost, until I remembered that Lily and I pretended to be together in the class. "Oh. No, she's at the spa right now." I don't know why I felt the need to keep up the charade, but I went along.

"Oh, well, if you don't think she'll mind, I can set you up to be part of a fake couple, just for the game. It would be with Alex over there." Paul pointed to the side of the stage where the black girl I had been lusting for on the beach yesterday was standing. She was looking at beautiful as ever. Instead of pulled back, her hair was out in a full, slightly parted afro. She stood talking energetically to another girl next to her. Her massive tits hung in front of her and entranced me immediately.

"Yea, sure sounds like fun. Lead the way.' Paul took me by the arm and lead me up to the side of the stage.

Paul made the introductions. "Alex, darling. This is Jason. He's going to be your pretend boyfriend for the game. Thank you both so much for agreeing to this. It's a big help. Alex, can you explain the game to him? I have go find another guy and girl to be the other couple."

"Hi, I'm Alex...but I guess you knew that already from Paul. Alex smiled in a bashful way. Her voice was sweet, and at her height she had to bend her head back to look up at me.

"Hey, so do you have any idea what this game is about?" I asked, trying to act casual. This was no easy task. Up close, she was even cuter than I thought. Her lips were full and glistening, almost pulling me in to kiss her. Her skin was smooth and dark brown, and up close I could see that her eyes were round and green. Her eyes gave her an innocent appearance that might also have had to do with how open and engaged she seemed. Nothing about this whole experience had any of the tinge of the insecurity or shame that I still held with nudity.

I tried to avoid outright staring, but looking down, I was in awe of her amazing chest. Her breasts were at least a D cup and stood out prominently from her fit and thick body. I wanted nothing more than to smother myself between them.

Alex laughed. "Oh yea. They put this on all the time. It's pretty simple. We are going to compete against another couple to see who can make the best outfit made only from whipped cream," She gestured to a giant bowl of whipped cream I hadn't noticed before that had been set on the side.

"Seems simple enough, I said. There was a part of me that felt slightly relieved that I would be partially covered by the cream.

"Yea, it's just for fun. Then there's the performance, but thats really on me I looked at her confused. 'What performance?" Oh god. I didn't have it in me to put on some kind of show.

Alex laughed again, seeing my hesitation. "You have nothing to worry about. You basically just get to sit in a chair the whole time. I'm the one who has to give you a sexy lapdance."

My mouth dropped slightly and my dick twitched in my swim shorts. "You're going to give me a lap dance?" I couldn't believe my luck. I had been lusting over her and working myself up just to talk to her. Within minutes of meeting we were going to be doing something I'd have to pay good money for back home. This was just further evidence that the resort was some sort of magical place.

I realized my shocked question probably made me seem deeply uncool to this girl who was unaccustomed to being bashful around nudity and sexuality. I tried to sound confident, "Well alright, should we get started then?"

Alex's smiled broadened and her eyes narrowed slightly. "I would love to, but we have a small problem." She brought her gaze down to my swim suit.

"Oh, right, I guess should ditch these."

"Listen, I can tell this is kind of new for you. It's no big deal, but I'll turn around to give you some privacy" she said.

Her turning around did nothing to improve my ease. All it did was give me a nice view of her ass up close. As I had suspected before, it was not as big as my sisters, but it was still gorgeous. It stood firm and matched her smooth complexion everywhere else. I could imagine myself thrusting my cock deep into her, but had to push these thoughts away to avoid getting fully erect. I took a deep breath, hitched my thumbs into my waistline and dropped my shorts.

Hearing the thud of my shorts on the floor, Alex turned around to take me in. She smiled approvingly. "Not bad," she said. She turned and walked over to the whipped cream bowl. "Alright, you first. That way we can touch up' any areas that need it after you put my whipped cream on and inevitably get hard."

"Oh, you're so confident, I joked. I had to lean into a more confident persona to match her lack of insecurity. I walked to her and stood up straight in front of her.

Previous Episode

Family Trip To Jamaica - S01 E21

Next Episode

Family Trip To Jamaica - S01 E23

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