Family Trip to Jamaica Part 6

As mom and I walked over to the pool, I thought over how much life had changed. This resort had brought out sides of my parents and sister I never knew existed. Lily was actually attentive and cared about how I felt. Dad was actually relaxing and trusting us. And mom had gone from mom jeans and PTA, to bikinis and T&A. I glanced over and watched her breasts soak up the sun as she walked. They were so perfect in shape and size. Walking next to her I felt proud, rather than annoyed, at the stares she was getting. This was part of my change too. I was getting more used to accepting my desire and enjoying putting myself out there on display.

As we passed the pool I made eye contact with the same guy who was a fan of my work when I modeled in the art class. He was like my one man fan club and I guess he couldn’t help himself from calling out to me.

“Hey stud! Another girl!? No surprise with what you’re packing down below!” He laughed to himself and rejoined his confused friends.

I waved back then caught mom’s baffled look.

“What was that about?”

“Oh, he was just in the class that Lily and I went to. I guess he really liked what he saw,” I answered, trying to sound casual so as not to invite too many questions.

“I guess he did. He certainly was enthusiastic. I guess I’m proud my son is becoming what it takes to turn on the guys and the girls,” she said with a laugh. “Well they’ll have to compete with me today while we spend some quality time together.” As she said this she put her arm around my shoulder and pulled me in for a side hug as we walked. Her naked breast pushed into my bare torso and a jolt of excitement went straight to my dick.” My mom held on as we walked down to the beach.

On the way, my mom flagged down a beach boy and ordered a few drinks and chairs to be delivered to us on the beach. We found a spot and sat in the sand while we waited for our lounge chairs and drinks. I scanned the sand for the beautiful girl I had seen the day before, or for Jane in case she wanted to go for round two.

Soon our drinks and lounge chairs arrived and we relaxed. My mom sat up quickly when she realized she had forgot her sunscreen. She asked a beach boy to get some. When he returned I braced myself for her to request me to put it on again. Maybe I wasn’t ready to accept that I want what I want yet after all. To my surprise, she instead turned back to the young beach boy.

“Could you lather me up, please? Im really worried I’ll get a burn.”

“The boy looked overjoyed. “Yes, of course ma’am,” he responded enthusiastically.

Relieved I wouldn’t have to risk having to deal with a hard on turned to jealousy. There was a part of me that wished she would have asked me.

My mom laid on her stomach on the lounge chair as the boy went to work. I watched out of the corner of my eye as he started at her back and made his way down. He massaged the lotion into her well-defined back, making her pale skin glisten. He moved slowly down to her mostly visible ass with the disappearing string. The boy must have been an expert at his because he took no hesitation to really massage her ass and spread the lotion between each cheek. His dark hands were in strong contrast to her pale skin. My mother, as she had done with me, spread for the boy, and he dove up her thighs with no guilt or shame. As the beach boys and other food service staff were some of the few partially clothed hotel staff, I could see a tent forming in his shorts. I watched on as he smiled but kept an air of professionalism.

This has to be the luckiest kid in the world, I thought to myself. I thought back to that age and fantasied about what it would have been like to lotion up MILFs at the local pool as a summer job.

“You may flip, ma’am,” he said. My mom flipped to her back and I could see the redness in her fair cheeks, no doubt a little turned on from the rub down so far. I turned my body so it wasn’t obvious I had been watching everything with interest so far.

As he lotioned up her legs, he again made no effort to avoid her bikini line. His fingers traced her bikini line, at times it seemed like he dipped a little below. He moved to her tight stomach then up to her breasts when my mom called to me so that i was forced to look directly at her rather than side eye.

“Jason, honey. Make sure you put some lotion on too. How’s your drink…” she asked several mundane questions that could have waited. All the while, the boy moved the lotions in circles, lovingly ensuring my mother’s breasts received ample coverage. Her nipples were rock hard as they met his hand and her tits moved slightly from the pressure. My mom thanked him when he was done, and he left to attend to other guests, making no effort to hide his erection. Lucky bastard.

My mom, seeing the straining on my own tight swim shorts urged, “Honey, why don’t you get those shorts off and relax. Try to enjoy the beach like everyone else. Besides, people are going to think you’re the waitstaff wearing those shorts.

“I don’t know mom,” and looking for any excuse I said, “besides, you still have yours on.”

This had the exact opposite effect than I had intended. My mom looked serious and said, “My gosh, you’re totally right. I can’t ask you to do something I’m not willing to do myself.” From her seated position she lifted her ass, then her legs and slipped off her string bikini. My dick went into overdrive and I feared it would burst through my shorts as I sat there looking at the mother’s bald pussy. Mom made no effort to cover herself or close her legs out of modesty.

I was completely unable to move, battling the old desire to look away, with the even more ancient desire to look. “Honey,” my mom said concerned. “Are you worried because you have an erection? Is that why you don’t want to get naked?”



“Yea, that’s part of it,” I muttered. I just was not at the place yet where I could show off my raging hard penis to my own mother. Even if a part of me wanted to so badly.

“Oh, well that’s OK. I don’t want you to do anything you aren’t ready for.” Mom then smiled, “Even if it means your poor old mother is the last one to see you naked. I mean, should I have that guy back there from the art class come and tell me all about it instead? Or even your sister?” she said jokingly.

“Ha ha. I don’t think I’m sober enough for these jokes,” I said. I recognized her efforts to try to make things easy and fun, and I appreciated them.

“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.