Family Trip to Jamaica Pt. 06

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. 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 I 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.

Alex gathered up a heap of whipped cream and spread it over my ass gingerly. Sure enough, my dick began to respond to her touch and rise.

"See that. We didn't even get to me yet." She continued her work. Though the whipped cream stopped her just short of making contact with my dick I couldn't help but be fully hard within a minute. She applied the cream to the underside of my shaft and pushed my legs open to connect it to the cream on my ass. "Alright, that should hold up nicely, even if you go soft. Which I doubt," she said, giving her ass a little flirty shake. "Now do me."

I put the cream into my hands and tried my best to act as 'professionally' as she had. Starting at her ass, I smeared the cream over her, and with a racing heart, tried my best to make it look like a bikini.

Sensing how I was covering her ass, Alex looked back. "No, no. Don't give me your grandma's bikini. Wipe it off and let's start over."

I scraped the cream off with my hand, feeling the heavenly feeling of her firm ass that when not flexed had a delicious bounce to it. After toweling her off, Alex handed me a whipped cream can. "Here, use this to give me a string bikini."

I started at her hip and as I got closer to the split in her ass, she suddenly spread her stance and pulled her cheeks apart. "Draw the cream right through there." My dick was in over drive. Did she really not get how insane this was making me?

I sprayed the cream in a line down her crack and over the other hip. Alex turned her body to allow me to keep spraying. I was focusing so hard on keeping the line straight that her bald pussy being directly in my face came as a surprise. I was so close that I had to actively resist the urge to shove my tongue into her.

"Hmmm, I'm thinking a triangle shape there. Give me some coverage, but don't travel too high. Keep it sexy."

I did as she commanded and met my cream line to the other hip to complete the bikini. "Not bad," Alex said, turning to look at herself in the mirror. "Now for these puppies." She said this as she grabbed a hold of both her breasts, giving them a squeeze, lifting them and dropping them. They bounced and swayed, almost hypnotizing me.

Out of self-preservation, I moved closer to her to start covering them with cream. Out of sight, out of mind. I sprayed on her bikini, remembering the style of my mother's. Two triangles with a string of cream meeting at that back of her neck.

"That's cute, good job," Alex said, looking down to admire my work. "Now let's decorate. We finished up by placing sprinkles and cherries in strategic spots. Looking in mirror I could see we did a pretty decent job.

Soon we could hear Paul hyping up the crowd. I guess he had found the other couple, but I didn't see them around. Soon enough, we heard Paul announce, "And let's hear it for our first couple. Alex and Jason are two very young love birds that have been heating up our beach recently. Some of you might have already got a preview of young Jason's assets yesterday. I know I enjoyed that view!" The crowd cheered at Paul lecherous calling. "Come on out!"

Alex scooped her arm into mine, careful not to brush against the cream bikini. "Let's do this. Don't be afraid to make it fun." We moved from back stage and into the bright sun. The crowd roared with cheers and seemed to have doubled since I was out before. A throng of mostly naked strangers, pressed up against each other and fueled by alcohol, were cheering us on. The energy was infectious and I couldn't help but smile.

Alex and I strutted together, and I could see she was having a good time. She smiled and made eye contact with the crowd, almost like she was in a pageant. I tried to match her energy and surprised her by taking her hand and giving her a twirl for the audience. They loved it and cheered with appreciation. As we walked, my dick, covered in cream, flopped around. Alex let me go ahead, and gave my ass a slap. I gave her a mock disapproving look, and we joined arms again, making our way to a chair.

"Look at these lovers's show each other off. Let's have our young buck take a seat and his beauty can stand right next to him."

I sat at the chair and Alex put her hand on my shoulder as she stood next to me. She suddenly squealed and called out, "Hi daddy!" She waved and bounced up and down making her massive tits jump. The crowd responded with more cheers and whistles.

I looked to where she was pointing and saw her father, who I had seen on the beach the day before talking with her. He had a big smile on his face and gave a thumbs up to his whipped cream clad daughter. I couldn't even imagine what it must be like for a father knowing he was about to watch his incredibly sexy daughter give her fake boyfriend a lapdance on stage in front of leering strangers. It was so strange, but a little hot at the same time.

I took in the crowd, and getting over the discomfort of sitting in a mess of whipped cream, enjoyed being on stage. I could see a lot of the girls in the crowd looking me over approvingly, nudging each other. I made sure to keep my back up and show off my strong torso.

Soon enough, Paul called out again. "Please welcome to the stage our next competitors. I found these two sexy beasts right here in the crowd. Diane is a fiery redhead who will absolutely burn up the stage. And she's brought her boy-toy I caught her flirting with to the stage to show off his big talent, if you know what I mean. Please welcome, Diane and Brad!"

If this was a few days ago, there's no way I would have made the connection with the name of the woman called and my mother. But a lot has changed and I knew what was coming. Sure enough, my mom, smiling huge, comes from backstage on the arm of a guy who was barely older than me. He was huge. At least 6'3'', incredibly muscular, and hung like a horse. Flashes of my mom applying the whipped cream to his monster cock flashed through my mind and a bit of jealousy surged up. Somehow my mom in a whipped cream bikini was hotter than her nude. More flashes of this Brad guy liberally applying whipped cream to my mothers luscious ass and perfect tits flitted across my mind. If it wasn't for the jealousy I'm sure I would be hard as a rock.

"She's pretty," Alex said, admiring my mother's beautiful body.

"Yea, she is," I acknowledged, not wanting to draw too much attention to my desire.

My mom walked with her graceful legs and bouncing ass across the stage and stood next to her adonis-like man. He sat in the chair that was about 10 feet to my left. Did Paul say something about her flirting with him on the beach? What would dad think? I projected my jealousy onto him to feel more justified in my feelings. My thoughts were interrupted by Paul.