Junior Year Part II
Chapter 21: Cheeseburger in Paradise

Copyright© 2017 by G Younger

Coming of Age Sex Story: Chapter 21: Cheeseburger in Paradise - Hollywood has been an entirely new experience, but David has enjoyed it - so far. That is, until his movie comes out and he finds out the real price of fame. David struggles with trying to be just a high school student when he is in the public eye. The real problem may be how it affects his love life. This is the continuation of the award winning Stupid Boy saga.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   mt/Fa   Humor   School   Sports   Slow  

Saturday March 26

The change in weather was welcome. We left fifty-degree weather to arrive to a high of eighty-five today. I stopped at the hotel gift store, bought sunscreen, and then met everyone for breakfast. A couple of preteens wanting autographs stopped me on the way to our table. The Star Wars effect was still in force, no pun intended.

“I just got a text. All our gear just arrived at the boat,” Brook said.

Brook had arranged for most of our stuff to be shipped ahead of time. Neither of us really wanted to lug our dive gear and a week’s worth of clothes. Her forethought had allowed us to pack just enough to get us to the boat today.

“Isn’t it nice when our kids are finally old enough to organize our vacations?” Ava asked Mom.

Mom gave Brook and me a big grin. If she was playing nice, I wasn’t about to say anything to get her out of her good mood. I was optimistic she would distract Brook’s parents enough that we might get some quality time together.

I noticed that Cassidy was being awfully quiet during breakfast. I looked at Brook and she shrugged, so on the ride to the boat, I sat by Cassidy in order to find out what was bothering her.

“What’s up, Buttercup?” I asked, and waggled my eyebrows at her.

“I’m not sure I should be here. This seems like it was intended to be a family vacation,” she said.

I knew everyone could hear us, so I decided to take advantage.

“Actually, this was intended to be a dive vacation for Brook and me, but the parental units decided to horn in. Brook wanted her best friend to join us, and I fully agreed that I wanted you to come too. Rumor has it Brook brought some bikinis along, and she’s worried they’ll attract so many men that I won’t be able to fend them all off by myself. I hope you’ll help me protect her,” I teased.

Ava’s eyebrows went up, but my mom shook her head to let her know I was goofing around.

“Who’s going to protect me?” Cassidy asked.

“Good question. I’ll have to think on that. Maybe you both should model all your swimsuits so I can be prepared. I might have to break out the Bo staff if they’re too scandalous.”

That seemed to satisfy her. I gave her a hug for good measure.


When we were dropped off at the marina, Ian and Dad went in to figure out where we needed to go. Dad led the way and I immediately recognized the yacht from the website. It was a 69-foot catamaran named Cheeseburger In Paradise. It held up to eight guests and had two crew, Sophie and Captain Eric.

They looked smart in their matching white shorts and polo shirts. Sophie was in her early twenties, while Captain Eric had to be around our parents’ age. There was tropical music playing to get us in the mood. Captain Eric took the older crowd to show them their rooms while Sophie led us to the other side of the boat to ours. The berths were in the two hulls, so we actually had to go downstairs to get to our rooms.

“I put you girls in this one, and David, you’re down the hall. David, why don’t you join us so I can tell you all about the amenities together?” Sophie asked as we walked into the girls’ room.

There’s was a queen-size berth, and I could see that someone had already unpacked for them. There was also an en-suite shower and head. I smiled when Sophie used the nautical terms for a bed and toilet. There was music piped into the room, and Sophie showed us how to select different internet stations. There was of course Wi-Fi, or I think we would have all gone insane on this trip.

My room was exactly like the girls’. I was amused to find a pair of Speedos laid out with a t-shirt. I think Sophie thought I might take the hint. Oh, well, we wouldn’t really be out in public, so why not? If I wanted to see Brook and Cassidy in tiny bikinis, I could at least play along.


While we changed, they cast off and began the first leg of our journey. Our first destination was Culebra, a small island off the east coast of Puerto Rico that offers some great water-based activities: beautiful beaches, great snorkeling and SCUBA diving, and awesome fishing, according to the itinerary. It would take us until about one to get there, so I planned to get some sun.

The main deck was split up into three separate areas. The center, called the salon, had the galley, a lounge, and a folding dining table, plus comfortable weatherproof Italian-style sofas. A separate sailing cockpit with an outside steering station was forward of the main salon. There was a covered area aft decked out in teak; it was an open area that could be used for lounging, entertaining and outdoor dining. Forward, there was a netting-like material stretched between the hulls that you could use to lay out. It was a little bouncy, like a trampoline, but when you laid down you felt you were in a hammock. You could see the water rush by under you.

Brook and Cassidy joined me on the netting. Mom and Ava were in the salon, Dad and Ian were lounging on the aft deck; I suspected they were all having cocktails already.

Sophie came out to check on us.

“I’ve done these trips many times, and something that will ruin your vacation is getting sunburned the first day,” she warned. “We’re closer to the sun than you’re used to, plus the sun reflects off the water. I’ve seen more than one person burn their back because the sun reflects through the netting.”

“How long should we stay out here?” Brook asked.

“You’re going to be out in it all afternoon, diving and snorkeling. I would suggest you come inside until you at least get a base tan,” she suggested.

I reluctantly went in.

“Put your shirt on,” Mom said when she saw me walk in with just my Speedos on.

I saw that Ava had about choked on her drink. I didn’t need to give Brook’s mom a show. I stuck my head outside.

“You guys want to play some poker while we travel?” I asked.

We ended up having a fun morning playing cards. Sophie made us snacks and served us fruity tropical drinks. It turned out no one was actually drinking alcohol. We followed the coast of the main island of Puerto Rico as we traveled east. We were soon past the island and headed to Culebra. Sophie told us that it was part of Puerto Rico and there was ferry service that brought people from the main island to the beaches for the day. Around Culebra, there were several small islands, and we were going to visit one of those.


We dropped anchor in the middle of a group of five small islands. The water was crystal clear and smooth as glass. We all decided to go snorkeling because the water wasn’t that deep, and Brook and I decided not to abandon Cassidy just yet. Everyone joined us but Mom. I’d have to ask about that later.

They’d picked the perfect place to snorkel. It was only six to twelve feet deep, and the protected area was teeming with different varieties of fish. If you got tired, it was an easy swim to the sandy beach or you could go back to the boat. Brook and Cassidy wanted to check out the beach, and there they found seashells. I was sent back to get them net bags for their shells and flip-flops for their cute feet.

It was the perfect no-stress day. The girls and I spent our time in and out of the water goofing off. I worried a little that Brook would push the sexy fun a little too far, but it was Cassidy that went way over the line. I’d pulled Brook to me and gave her a kiss. We were standing in water up to my chest so I wouldn’t embarrass myself if anything came up.

Cassidy swam up behind me and pressed her body to my back. Brook giggled as she kissed me harder. Cassidy reached around and pushed her hand into my Speedos. I think they planned this because Brook grabbed my head to keep me from dealing with Cassidy. In a coordinated effort, I found Mr. Happy free and Brook sliding onto my pole. I decided they knew best and just went along with it.

Sex in water isn’t the best, but it’s much better than no sex. Once we were joined, Cassidy came to my side and pulled my head to hers so she could kiss me. Then I completely lost it when Brook stopped us kissing and she kissed Cassidy. Were they more than friends? Mr. Happy got overexcited as he tried to wrap his nonexistent brain around what it all meant.

“What was that?” I asked as I stuffed my cock back into my Speedos.

“You do know that Cassidy is into you?” Brook asked.

“Yeah, yeah, and I’m into her. That’s not what I was talking about and you know it,” I said, and could tell they were going to make me say it. “The kiss?”

They both gave me mysterious looks and swam back to the boat before I could ask any more questions.


Before I could explore my Brook-and-Cassidy fantasy, my dad grabbed me.

“We need to talk,” he said cryptically.

Had they figured out that we’d just had sex? I followed him down to their cabin.

“We’re not allowed to come down to this side,” I tried, as Dad opened the door.

“You do know we’re going to be doing bed checks,” Mom said.

“I knew Ava was a perv. She just wants to see me naked, doesn’t she?”

I think Dad would’ve left, but he’d called this meeting.

“Maybe I should get her to help me check my tan lines. She’s a mom, helping, after all,” I continued.

Me and my big mouth. Mom made me go over and let her check.

“If you two are done? We need to talk about your mom’s doctor’s visit,” Dad said, taking all the fun out of the room.

I sat down by Mom, and she took my hand into her lap.

“I went to the doctor on Monday and he did a complete checkup. He called Thursday and my blood work showed that cancer hasn’t come back. He did find some skin spots he was worried about, so I went to a dermatologist on Friday. He found a couple of spots on my back that he removed. He thinks it’s skin cancer, but we won’t know until Tuesday for sure,” she said.

“But skin cancer is no big deal, right?” I hoped.

“People get it all the time and have it removed. Most are okay, some will get it again, but for some, it can become serious,” Dad said.

I suddenly felt sick to my stomach. My mom had been through enough. I was glad I listened to Jeremy Pike’s psychic advice to have her get checked. Coincidence or not, I needed to thank him.

“What’s the plan?” I asked.

“We won’t know until Tuesday, but for now I stay out of the sun for the most part.”

I just nodded.

“I need to check your dad’s tan line,” Mom said.

That was my cue to leave.


I went to my cabin to take a quick shower to get the saltwater off and found Cassidy in my shower. I squeezed in behind her.

“David,” she complained.

“Why are you in my shower?” I asked, as I grabbed the shampoo and used it on both of us.

“Brook got to ours first, so I figured I’d just use yours.”

I then used a conditioner on both our heads. Salt water can be hard on hair if you don’t take care of it. When we were done, I dried her off and then combed her hair out. She had a contented smile and her eyes were closed as I worked on her hair. To this point, I’d been the perfect gentleman, and even Mr. Happy had cooperated.

I stopped combing, and Cassidy’s eyes opened and locked with mine.

“Make love to me,” she said.

I let her lead me to the bedroom and we got on the bed. She pushed me back to check me out. I came to realize that I was in trouble. Cassidy wasn’t just any girl. It felt like after Tami had broken my heart, I’d been working to create a hard shell around it for protection. While I cared about Halle, Zoe and Brook, I’d never let them past that shell. Cassidy seemed to know and touched my chest. I felt the hard shell melt away and my heart open up to Cassidy Hope.

In the back of my mind, I knew this couldn’t last past this week. It was time to invoke vacation rules and just let this happen.

“Come here,” I told Cassidy.

We kissed and I growled and rolled onto her, pinning her to the mattress. Cassidy spread her legs and my cock was suddenly hard and at her entrance. With a little push, we were joined.

“I knew it,” Cassidy hissed.

“Knew what?”

“That your cock would fill me up. Jesus, you feel good.”

I gave my hips a little twitch, and Cassidy almost purred like a satisfied cat. Once we got started, Cassidy was Cassidy. She was vocal and gave as good as she got. When I came, I swear Cassidy emptied my balls. I was in a dazed stupor when she hopped out of bed.

When Cassidy opened the door, Brook about fell into the room.

“You dirty little slut,” Brook said.

I heard them both giggling as they went to their room. I just nodded off.


I woke with a start to find Sophie staring at me. Her face went red when she realized I was awake.

“Uh, Brook said you had gotten some sun and asked me to bring you some cream,” she blurted.

Mr. Happy seized control of the body, and I reached over and pulled Sophie into bed with me. She didn’t resist me as I undressed her. Someone didn’t have any tan lines. I flipped her around and got her into a sixty-nine position. She knew exactly what to do. She had a nice athletic body with larger breasts than I’d first thought.

When she’d gotten me fully hard, I grabbed a condom and put it on.

“We have to hurry,” she ordered.

Fine by me. I got her into a doggy-style position and filled her sex. I just went to pound town, which was what Sophie seemed to want. She came quickly, which caused me to redouble my efforts. By the time I came, she’d had another.

“Thanks. I needed that,” she said.

She got dressed and left. I took another shower and put on board shorts and a t-shirt.


Sophie displayed her cooking skills at dinner. She grilled steaks to perfection, made a huge salad and baked potatoes. I was worn out from a day of swimming, sun and fun. It was a good tired and much needed. I grabbed a big pillow and went forward to watch the sun go down as we set sail for our next destination, St. Thomas in the US Virgin Islands.

Dad and Ian had booked a tee time at a golf course on St. Thomas. Mom, Ava and Cassidy planned to go shopping, while Brook and I were to dive a wreck. We would reassemble for lunch and then sail to St. John. They were having a Blues Festival, and the plan was to stay and enjoy that. Then we would sail to the British Virgin Islands where I would get to go surfing. Sophie told me that we could also try kiteboarding. Both Cassidy and Brook were eager to try it, so I agreed to include that on our bucket list of ways we could try to kill ourselves.

Everyone left me alone as I watched the sun go down. They’d all gone aft and were listening to calypso music and drinking fruity concoctions. It gave me a chance to think about Alan.

What he’d done to Lisa was childish and mean. He obviously hadn’t thought through the possible implications. First, the school wasn’t a hundred percent happy that he and Lily had set up a lot of the school’s new websites and communication tools. By abusing his power, he could get his access shut off. After seeing what he did to Lisa, I would be inclined to pull it. Second, my image could have been damaged by his stunt. All it would have taken was a leak to an unfriendly reporter and the story could have been slanted in a negative way. I spent a lot of money on Frank and his team to make sure that didn’t happen. Finally, if word got out that Alan was behind the hacks, people might shun him in fear of what he would do to them.

I called Tami to get her advice.

“I don’t want to hear about your trip. They say we might get down to thirty degrees tonight,” Tami said.

“I really should start taking pictures.”

“Don’t worry about it. Between your mom, Brook and Cassidy, I’ve seen you in your Speedos.”

“As long as I look good,” I teased.

I needed to make sure Frank was aware that pictures would be on certain people’s Instagram accounts.

“I have something serious to talk to you about, and it could affect you,” I said.

“What now?” she asked, getting serious.

“Alan was the one that hacked Lisa’s private blog and posted it on the Lincoln chat board,” I said.

“Are you sure?”

“I had Frank Ingram’s team take it down and track who posted it. He assures me it was Alan.”

“What do you plan to do about it?”

“I’m actually contemplating whether I should distance myself from him or not. Alan hasn’t really acted like a friend for a while. He’s gotten a mean, snarky edge to him, and I can’t really see a good reason for what he did to Lisa.”

“Without Jeff around to cushion him, I’ve been wondering the same,” Tami admitted.

“I thought it was just me. What do you think we should do?”

“I don’t have to do anything because I don’t have to deal with him at Wesleyan,” Tami said.

“You’re such a pussy. You’ll be sucked into this as soon as I do anything. Alan is nothing if not a tattletale. You’ll be his first call,” I predicted.

“Okay, ‘stupid boy,’ this is what I would do. First, you need to tell Lisa it was Alan. Instead of letting her kick his ass, talk her into telling the school. He used school resources to bully her. Alan won’t stop unless there are consequences.”

I liked the idea of Lisa taking the lead. It would be good for her to be in control. I was confident that with help and support from Tracy, Pam and me, she could do it.

“What scares me is that Alan might pull out the nuclear option. He was there on the recruiting trips and was there for some of the stunts we pulled growing up. While it wouldn’t be the end of the world, I’m not proud of everything that happened,” I admitted.

“That’s your best argument for not getting me involved. I can be the voice of reason and warn you if he decides to do anything rash,” Tami said.

I could then show up at his door and bring my mom with me. Alan may not be afraid of me, but my mom scared the shit out of him. She could have a five-minute conversation with his parents and Alan wouldn’t see the light of day until he moved away for college.

Then my conversations with my mom and Coach Haskins pushed their way into the front of my brain.

“Does this really matter?” I asked Tami.

“What do you mean?”

“When I was deciding what to do about my future, I had a talk with Coach Haskins. Actually, I had a similar conversation with my mom.”

“What was it about?”

“He told me that when he was my age, he was given a chance to play baseball. He grabbed that opportunity and never looked back. I asked if he ever regretted leaving all his friends behind, and he told me that he honestly hadn’t ever thought about it, so he guessed not. Mom said something similar about her high school friends. She only kept in touch with Mrs. A.

“Coach said that while high school had been an important time in his life, it was just a moment in the larger scheme of things. That he sometimes wondered how everyone turned out, but I guess his point was that I was too focused on it. That once I put high school behind me and start to live the life I’m supposed to live, that will become my focus.

“I look at Alan, and he’s been one of my best friends since we were in grade school. I guess the real question is, why? I look back and realize it was because of Jeff. The longer Jeff is gone, the more it’s evident that he was the glue between Alan and me.

“You and I were different,” I admitted.

“How’s that?”

I smiled.

“When you walked into my class, I could see you needed a friend. I think I knew that I also needed a friend. What I found was someone that had my back no matter what. That was why I let you boss me around.”

“It was, was it? It had nothing to do with you being a lazy sack?”

“Maybe,” I admitted.

“So what’s your point?”

“I guess I’m asking, is Alan worth the effort? If in ten years from now my life is completely different, and Alan won’t be in it anyways...” I trailed off.

“That’s kind of a harsh way to look at it,” Tami pointed out.

“But is it the wrong way?” I asked.

Tami went silent. I smiled again.

“You know, I almost did the Star Wars movie. I almost did like Coach and just stepped into my life. I knew that if I took that role, I would never look back.”

“What stopped you?”

“Something my uncle taught me. Being a man of your word means something. If you give your word, it doesn’t mean ‘until something better comes along.’ I’d given my word to Chubby Feldman that I would do his movie, and the Star Wars movie would have overlapped it. When it came right down to it, I had to be able to wake up in the morning and look at myself in the mirror.”

“You’re a better man than I deserve,” Tami said.

“You’re just now figuring that out?” I asked with a nervous laugh.

I heard her take a deep breath. Was she crying?

“You okay?” I asked.

“I guess I’m just realizing what a truly terrible decision I made last summer. When you talk like this, I feel like I’m the one that needs to grow up. I hope you realize that it was never you not being enough. You’ve always been enough if I’d been honest with myself. I see now I was so unfair to you. I just hope there’s a time we can actually have a ‘someday.’”

“The one thing I’m starting to see is the long game. If what Mom and Coach Haskins said is true, then we should focus on having fun in high school. If that means you go out and find a boyfriend, so be it. If we’re meant to be, it’s not going to happen anytime soon. I look at what you did to me over the summer as a favor. We would never have survived what I’ve gone through the last few months. I’m actually glad not to have a serious girlfriend right now. I’m still trying to get used to what it means to be famous.”

“What do you mean?”

“A good example happened today. I slept with a girl who has to be six or seven years older than me.”

“Slut.”

“Yeah, that too. The point is most teen boys would never have a twenty-something girl offer to have sex with them.”

“You’re right. We would never have survived all that.”

I laughed.

“Why did I just tell you that? What were we talking about?” I asked.

“Alan,” she said, and then sighed. “I really am trying to not tell you what to do. I need to trust you to make your own decisions.”

“Then do, but that doesn’t mean I don’t want to hear your opinion.”

“Point taken. Look, Alan has changed, and not for the better. The night Brandon drugged us, Alan was all over me. At the time, it felt wrong. I actually thought he might have raped me. I’ve had my doubts about his friendship. I think we’re both hanging on to the ten-year-old Alan and ignoring who he is now. I don’t plan to not hang out with him now and then, but I also don’t plan to make a point of it.”

“What about the talk I had with everyone at Monical’s? Do I still include him?” I asked.

“I think you care enough to help him achieve his dreams. I just don’t think you have to bend over backward to help him get there. Point him in the right direction and set him free.”

“I can do that.”

“Also, he needs to learn shit has consequences. Stop covering for him. He needs to learn to stand on his own.”

“What if he gets his ass kicked?” I asked.

“How long has he had that coming?”

“Wow.”

“Well, don’t let them kill him.”

“Got it.”

“Go have fun. Tell Brook that she needs to take some pictures with your face in them.”

I could only imagine.


Sunday March 27

“David Allen Dawson!” Mom barked.

Ava jerked her hand back. I’d told Mom I would show her my butt.

I’d gotten up early and swam to shore for a run on the beach. When I came back, Ava was checking me out, and no one was around. I told her I was worried I might be getting too much sun and pulled my shorts down on my left buttock so she could see my tan line. I’d asked her if my skin felt hot. That was when Mom showed up.

I decided not to try to explain, based on the look Dad gave me when I came up the stairs. I went and took a long shower. When I came back up, everyone was gone except Brook, who was eating an omelet.

“You have to stop teasing my mom,” Brook said.

I just shrugged and grabbed a glass of orange juice. Sophie brought me a bacon and Swiss omelet. While we ate, Captain Eric sailed us to the dive site. All our gear was laid out. I’d brought my surfing wetsuit jacket. The water was eighty degrees, but as you went deeper, it got colder.

We were diving at Cow and Calf Rocks. It was a maximum of thirty-five feet, so we didn’t have to worry about it being a hard dive, but it was deep enough to cut our teeth on. The attraction of the spot was that there were tunnels and some large caves.

Captain Eric put out a dive flag to indicate we would be in the water. There were a couple of other boats around because this was one of the prime diving spots around St. Thomas. Brook and I jumped in, made sure everything was working correctly, and then headed down. The first tunnel we found was more of an arch. Being claustrophobic, I’d not really been thrilled about diving tunnels, but Brook seemed excited.

All the fish and colors made up for any discomfort I had. Then Brook spotted another tunnel and shot into it. We’d been taught not to leave your dive-buddy, so I gamely entered the mouth of the tunnel. This one was a little different. It was much more narrow and dark. You could barely make out a light at the other end. This passageway reminded me too much of a death trap, and I tried to grab Brook’s fin to stop her, but just missed.

The other problem was there was a current pushing through the tunnel which seemed intent on pushing me against the walls. Unlike the rocks on the surface that were smooth, these were rough. I ended up using my hands to keep me off the ever-closing walls, and I noticed my hands were bleeding. Great! I was also about to become shark food.

I saw Brook shoot out into the light. The tunnel had narrowed down to the point where I found I was stuck. I mean, seriously, I was stuck! Ever have your vacuum cleaner suck up a sock? The engine begins to whine and seems to lodge the sock in the tube. In essence, I was the sock that the current was suddenly pushing against. Brook saw my dilemma, and her solution was to pull on my arm. That just hurt.

I calmed my mind and remembered what we’d been taught. If you were in a tight place and got stuck, the first thing you tried was to take off your tank. I pushed back just enough to get room to unlatch my harness, wiggle it over my head, and hand it to Brook. Next, I took off my weighted dive belt. That was enough for me to worm through to freedom.

Brook asked with hand signals if I wanted to head up, but I figured this was just part of the fun, so I got everything back on. We then found a group of sea turtles and followed them to another rock grouping that was alive with fish. It made me appreciate the allure of a salt-water aquarium. Out of nowhere, what seemed like a wall of baitfish surrounded us. There had to be thousands of them. It took my breath away as they darted around us; then suddenly, like a cloud front, they passed. I decided right then we had to get an underwater video camera.

We started to get low on air, so we went back to the boat. Captain Eric let us borrow his camera that also took video under water. We went down three more times. We dived some old wrecks from World War II, which was fun. Brook respected my fear of tight places and didn’t make me go inside the boats. Soon it was time to go meet our families for lunch.


“What’s with the glasses?” Ava asked me.

“My security people gave them to me. It’s a body-cam,” I explained, then took them off and showed her where the camera was.

“Didn’t they have something more attractive?”

“They gave me several different items, but this was the easiest to grab. I’ll show you my other options when we get back to the boat.”

The girls had picked a place on the beach to eat at. Dad and Ian had suggested the country club, which I thought sounded good, but we were outvoted. I was glad we were. I had a grouper jerk sandwich that was out of this world. The grouper held up well to the jerk seasoning.

Cassidy was the wimp of the group and had a hamburger. I did get her to try a bite of my sandwich. That was a mistake because she wouldn’t give it back. I didn’t feel up to fighting her for it. That, and I didn’t want to be seen in public getting my ass kicked by a little girl. The burger wasn’t bad, either.

After lunch, we sailed to the next island over, St. John, where they were having a Blues Festival. Sophie went with us because she wanted to meet some of her friends. We had a blast. They had a main stage with different bands all day. If you got bored or didn’t like the band, there were little bars and restaurants that had other bands. There were also booths selling anything and everything. I bought a bunch of different souvenirs for people back home.

Brook found a place playing authentic zydeco, and she and Cassidy talked me into dancing with them. The good news was that everyone was pretty lax about the drinking age, so we indulged in a few island beers. We hooked up with the parental units for dinner. I had the best fish tacos of my life. This time I made Cassidy get her own.

 
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