The Castaway Hotel - 8 - 39. Chapter 39 - Many Firsts

Once Sammy and Ted were alone, Sammy got out the condoms and lube I had each of the older groups take and keep in their room. He took his time lubing Ted up and made certain Ted was loose, before he slipped on a condom and lubed it up as well. Once both of them were ready, Sammy had Ted get on his hands and knees, so he could enter him from behind. He knew this was the easiest way for a first-time experience, at least as far as Ted would be concerned.

Slowly, Sammy eased his way inside Ted, while taking all precautions to avoid hurting him. However, Ted had practiced by inserting items with a greater girth into his rectum, and because Sammy did not possess a thick penis, Ted accepted the intruder without any difficulty. When Sammy was seated completely within his love canal, Ted urged him to continue.

Without needing further encouragement, Sammy began to rock back and forth, so his penis slid in and out of the warm tunnel. Sammy started very slowly, until he was convinced Ted was feeling no pain and enjoying the encounter, and then began to speed up. It didn’t take long before Sammy started to feel the familiar tingling sensations radiating from his loins, so he knew his release would be close behind. For a brief time he was able to resist the urge to speed up, so he could experience the ultimate high, but he delayed it for as long as he could. When he could no longer deny his sexual fulfillment, he quickened his pace, and within minutes spewed his seed into the condom’s reservoir. At that point, he collapsed on Ted’s back and they fell, prostrate, onto the mattress.

After regaining their wits about them, Sammy rolled off of Ted and looked into his face. “Well, how was it?” he wondered, since he also wanted confirmation he had performed adequately. “Was it as good as you’d hoped?”

“Oh, yes,” Ted gushed. “It was wonderful. I figured it would be good, but it made me tingle all over, especially back there.”

“But you didn’t cum,” Sammy observed.

“No, but I feel as good as if I had,” Ted confirmed.

“That may be,” Sammy confirmed, “but I want you to enjoy that part too. That’s why I’m going to let you make love to me now, so you can cum too.”

“You don’t have to do that,” Ted responded, since he felt Sammy felt obligated to return the favor.

“I know that,” Sammy acknowledged, “but I want to do this for you. It’s the least I can do, after you let me be your first.” Teddy blushed after Sammy pointed out the fact that Ted had just lost his virginity.

“Okay, if you’re sure,” Ted agreed. “I won’t tell you I don’t want to do it too, but I just don’t want you to feel you have to do this for me.”

“I don’t,” Sammy confessed, “but I do want to.”

Ted rapidly accepted the offer, as well as the condom and lube that Sammy held out to him. Ted eagerly prepared himself, while Sammy did the same, and then they got in the same position they had used earlier. Ted’s penis was as hard as a diamond, but he still had a bit of difficulty entering Sammy, until Sammy told him to hold the base of his penis, as he inserted it. This seemed to help, so before long Ted penetrated Sammy’s tunnel of love.

Ted was so aroused that he nearly spewed as soon as he entered, but he held steady for quite a few seconds, without moving a muscle, until he felt the urge subside. As soon as that happened, he began easing back and forth, until he built up a rhythm. Since he had already been on the brink of his orgasm, it didn’t take long for Ted to reach that point again and he filled the condom with his seed. Emotionally spent, Ted collapsed on Sammy’s back, which forced Sammy to collapse onto the mattress.

It took more than a few seconds for Ted to realize Sammy was uncomfortably pinned beneath him, but when he did, he rolled off and thanked him for what he had just experienced. He was now satisfied and sated, at least for the time being. Once they recuperated, Ted and Sammy showered together, before emerging from their room and locating the rest of the family. I was just returning with a group, after we finished our tour of the bridge, and Jake was ready to take the next group up. As soon as I saw them, I could tell by the expressions on their faces that the experience had gone well, so I didn’t question them about it. However, Sammy did fill me in about how things went a little later and I was pleased Ted’s first experience at anal intercourse had gone so well.

Getting back to other matters, all of the boys enjoyed their time on the bridge, especially since the Captain allowed each of them a chance to steer the boat briefly. I surmised they weren’t actually in control of the vessel, although most of them believed they were. I felt the ship was more or less on autopilot at that point and the ship’s computers were responsible for its progress, rather than any of us. Regardless, it was a memorable experience and we thanked the Captain profusely before we left.

This was our last Fun Day at Sea until the return voyage and the next three days would be spent enjoying one of our three tropical destinations. Tomorrow we would arrive at St. Maarten, Nassau, where we would stay for several hours. I spent the evening discussing our itinerary with Jake and we ironed out the details of what we were going to do. I had changed my plans slightly, after listening to the Captain’s suggestions about what we should do, but now we were ready for fun in this exotic location.

We disembarked at 7:00 the next morning, since we were among the first allowed to go ashore. I had told the boys to wear their swimsuits under their shorts, because we’d probably have a chance to go swimming in the ocean, and they were all eager to go along with my suggestion. We then began our time in St. Maarten with a tour of the beautiful French/Dutch Island and quickly discovered the charms of both cultures. We started our excursion in Phillipsburg, the capital of the Dutch side of the island. As we traveled along Perimeter Road, we were able to view many of the historic homes and businesses located there, as we headed to our objective, lookout point. From there, we enjoyed some spectacular views of both the island and the ocean and I even contemplated what it would be like to live there all year long.

Once we grew tired of taking in the scenery, we went to the French capital, Marigot. We spent quite a bit of time exploring the quaint little shops lining its main thoroughfare and discussed how the various businesses hadn’t changed much over the past couple of centuries. Sure, they had electricity now and added indoor plumbing, but the overall appearance was basically the same. The main difference was in the type of items they offered, although quite a few of them were the same as well, except for the fact they were now packaged differently. During this time, the boys bought some souvenirs, to remind them of their time here. Once we finished up our little spending spree, we walked past the resort areas and luxury hotels, when the boys began to tease me about going swimming. I thought it was a good idea, so I stopped a couple of the locals and asked where we could find a nice secluded strip of beach.

I did this because I wanted the boys to totally enjoy themselves, without worrying about making too much noise or bothering other tourists. I quickly learned there were a couple of locations close by that would meet our needs. In fact, both locations were only a short walk away and I was intrigued by the descriptions I was given about them. After hearing the locals out, I thanked them for the information and took the boys on a quick walk to one of these spots. When we arrived, I told them they were on their own for a while, before I disclosed the fact that this particular stretch of beach was clothing optional. The boys quickly began to look around, to verify my statement was correct, and beamed when they noticed a couple of other people sunbathing nude.

A few of them immediately began shedding their clothing, although most were in no hurry to do so. They did strip down to their swimsuits and began to head toward the water, while I helped Andrew cover his cast, so he could also share in the fun. Dustin, Barry and Jesse had all agreed to stick close by and watch over him, so after making sure his cast wouldn’t be damaged, I sent them on their way. Now, Jake and I could also enjoy the beautiful surf. The water was very calm and crystal clear, and the white sand seemed to extend forever. The mountains loomed up in the background and created an exquisite backdrop to this lovely setting, and we spent the next half hour or so thoroughly enjoying the sun, surf and beach.

A few minutes after we arrived, I scanned the area to make certain everyone was doing all right and enjoying himself. That was when I noticed nearly all of them were naked now, including Ted and the three youngest. The only ones still wearing their swimsuits, beside Jake and I, were Carlos and Cole. I understood later that Carlos was a little shy about exposing himself to the other visitors on this beach, so Cole kept his suit on so Carlos wouldn’t feel he was the only one who wasn’t participating. Cole told me Carlos had admitted to him that he felt self-conscious, since he didn’t think the size of his penis measured up to that of everyone else, especially after he’d been in the water. I could understand why he felt this way, since some of the boys were quite well endowed. Even Jesse and Barry were nicely hung for their age.

Once we finished up our swim, the boys air-dried, by lying on the beach or just walking around in the sun, before putting their clothes back on. Once they were all decent again, we made our way back to the Dutch side of the island. After enjoying a quick lunch, I led the boys to where we would start our next outing. It was called the ‘Rhino Rider & Snorkel Adventure.” I had to do a bit of persuading to get the person in charge to allow me to include Andrew, since it was a requirement that all participants be adequate swimmers. Seeing Andrew was sporting a walking cast, it was deemed he didn’t meet that requirement. Since I didn’t want everyone to miss out, if I opted to bypass this activity, or Andrew to feel badly because he couldn’t participate, I tried to negotiate. After some pleading and agreeing to sign a waiver of liability to protect the operators of this site, Andrew was given permission to go. However, that wasn’t our only problem.

The next situation arose because we had an odd number in our group. There were twenty-three of us and there is a strict limit of two persons and 400 pounds per boat. Besides making it clear that Jake and I couldn’t go together, it also meant someone would have to go alone. We were discussing this problem when a couple we met on the ship offered a solution. They wanted to go on this adventure too, but if they rode together, their son would have to go alone, so they had hurriedly decided to have the mother and son ride together, while the father went by himself. However, after hearing we had a similar problem, they thought we could help each other out. After discussing the situation with everyone, Pat offered to go with the couple’s son, who immediately agreed with the arrangement. In part, his rapid consent was due to the fact that he was feeling badly that he was going to be responsible for splitting up his parents for this activity. Since he knew they really wanted to do this together, his going with Pat meant everyone was now satisfied with the arrangements.

Since I had promised the organizers I’d keep Andrew with me, when I vouched for his safety, Dustin said he’d take Jesse and Jake agreed to have Barry ride with him. Since Jesse also met the minimum 10-year old limit, we had no other problems. The rest of the roommates had agreed to stick together for this outing as well, so now that those details had been seen to, I turned my attention to something else. Quickly, I checked to see that Andrew’s cast was still wrapped up and wouldn’t get wet during the ride and then we set off.

Each pair quickly decided who would pilot the ten-foot Rhino Ride motorboat, since whoever operated it had to be at least sixteen. When all of those details had been seen to, we took the short ride from the pier to Simpson Bay Lagoon, where we were given a brief orientation and safety briefing. After everyone agreed they understood what they’d been told, we navigated the water and dodged the private boats and mega-yachts that were anchored in the area. Once we had cleared those obstacles, we exited the lagoon and rode along the picturesque coastline, until we reached our final destination, Happy Bay.

Upon arriving there, we were given the choice of hiking, swimming, snorkeling or just laying on the beach for the next hour, before making the return trip. The vast majority of the boys wanted to go snorkeling, so I gave them my blessing, after advising them to be careful and no horseplay. Once they agreed, they followed the guide for a quick briefing. Some of the others went swimming, which left only the three youngest, Jake and I. We had decided to take a short hike, to look around the area, since the boys felt they had done enough swimming earlier. Andrew insisted he could walk, but Jake and I offered to alternate carrying him, piggyback, so we could go farther and see more. Andrew seemed to like the idea, so we took off.

It was quite lovely, as we hiked along the trails. The path was surrounded by thick tropical vegetation and we also took our time and stopped to look at whatever creatures we encountered along the way. We spotted many different types of birds, a few lizards, spiders and various insects as we traveled along, and we also spotted a couple of turtles. Fortunately, though, we didn’t see any snakes. The boys were disappointed about that, but I insisted it was probably for the best.

The hour went by quickly, especially for the group that went snorkeling. After a brief safety lecture, they followed their guide to Shipwreck Cove and investigated the wide variety of vessels that had sunk there. Of course, when snorkeling you can’t go very far below the surface or the breathing apparatus would become filled with water and you wouldn’t be able to breathe, so the boys couldn’t dive down and investigate the wrecks. However, they were able to spot several of them.

During this outing, the group spent some of their time treading water, so they could listen to their guide when he shared many details about what they had seen. He told them about the various wrecks and pointed out the different species of fish swimming around them. He also provided the boys with packets of items they could feed the fish, and surprisingly, the fish seemed eager to approach them and accept the handouts. In fact, some of the fish became quite bold at letting the boys know they wanted something and each of them was thrilled the fish weren’t shying away. Once everyone tired of doing these things, they spent the rest of their time investigating the rest of the area, before returning to shore. From there, they moved to a sundeck, where they were encouraged to make themselves comfortable. During this time, they listened to Calypso music and sipped the rum or fruit punch that had been provided, depending on their age. From the looks on their faces when we returned to join them, I’d say they experienced a truly memorable time.

A short time later, we all boarded our motorboats and made the journey back to our starting point. Although it seemed as if we had just begun, nearly three and a half hours had passed since we set out on this portion of our cruise. It was now time to head back to the ship, so we could set out for our next port of call, which would be Barbados.

We had dinner on the ship that evening and the boys eagerly discussed the day’s experiences with each other. I merely sat and listened in on their joyful recounting of what they had done. I was pleased to note this vacation was meeting their expectations and earning their approval.

It was a very quiet evening, after we returned to our rooms, because everyone was fairly exhausted from the day’s activities. While we slept, the ship sailed to the next port and we arrived the following day, around noontime.

Sunday morning started out with a quick breakfast and a non-denominational church service, before we docked at Barbados. We disembarked shortly after noon and immediately went to our first activity. I was taking the boys for a ride on the submarine, Atlantis, and it worked out that Jesse exceeded the minimum height of three-feet, which was required to be able to go on this adventure.

As we entered the sub, we took up nearly half of the available spots on this forty-eight-person vessel. While we settled in, I noticed Jesse and Andrew were carrying on a very animated conversation. When I inquired if there was a problem, Andrew informed me Jesse was concerned about traveling underwater. I was about to try calming Jesse down, but Andrew started speaking instead.

“I know it’s a little scary when you think about going under so much water, but they do this all the time,” Andrew explained, but Jesse didn’t look convinced.

“It’s really safe,” Andrew continued. “People have been using submarines for over one hundred years and we aren’t going to be going very far down, so it’s all right.” Jesse still looked skeptical and I was ready to jump in and assist him, but Andrew spoke again, before I had the chance.

“Do you believe Dad loves us?” he asked. Jesse sat stunned for a couple of seconds, as he looked between Andrew and me, but then he began to nod his head energetically.

“Then do you think Dad would let us do this if it wasn’t safe?” Andrew followed. Jesse only took a second to think about this, before he began shaking his head in response.

“Then relax and enjoy the sights,” Andrew advised him, while glancing over at me. I was very proud of the way he handled this and smiled in approval. What he had said seemed to do the trick, so our journey began a few minutes later.

The cabin was surprisingly spacious, as well as air-conditioned, so the time we were aboard was quite pleasant. I think we all felt a little giddy as we looked out the observation windows, when the submarine began its descent to fifty-five feet. This was so we would be able to view a coral reef, along with the multitude of colorful fish and other aquatic life that thrived here. Afterward, we dropped to somewhere around 150 feet, so we could view a shipwreck that was lying beneath the crystal clear water, before we leveled off. That was as deep as we were going to go.

When we surfaced later, the boys couldn’t stop talking about everything they had experienced and Jesse was just as excited as anyone else. Although he had initially been hesitant about going, he was probably more impressed than the others and couldn’t stop thanking me for letting him go. I was thrilled to see him so animated about this experience and enjoying himself so much that I bent down and picked him up. I gave him a big hug and kissed him on the forehead, before I set him down again. It was a truly wonderful moment.

Later, as we were enjoying our dinner, I announced that I was going to give everyone a choice for his next activity. They could either take a tour of Barbados, with Jake and I, or try their hand at scuba diving. I knew only the most adventurous would select the latter option, so I wasn’t surprised when I heard their responses. It ended up that only eleven of the boys opted to try the scuba diving, but making this choice didn’t happen without some problems. As it turned out, some of the couples didn’t have the same interests and selected different options. Dion wanted to go scuba diving, as well as Kevin, but Trey and Vinnie weren’t eager to try it. It also split up some roommates, because Little Ricky wanted to give the scuba diving a go, but Graham was reluctant.

After some discussion, Trey and Vinnie agreed to become partners for the tour, so their lovers could go diving, and Graham said he’d spend time with Andrew, Jesse and Barry, so Little Ricky could go too. I was happy they had worked this out for themselves, without getting me involved.

About this time, I began to also feel Jake wanted to try the scuba too, since Shannon was in the group that wanted to go, so I urged him to join them and I’d take the others on the tour. After some slight reluctance, he finally agreed it might be best if he went, so he could keep an eye on those who wanted to do it. I merely smiled, nodded and gave him a good-bye kiss, before I watched him lead Danny, Brandon, Dustin, Shannon, Nick, Pat, Dion, Kevin, Little Ricky, Ricky and Peter to where this would happen.

Barry had been eager about trying this too, but I was hesitant about allowing him to go, without his parents’ expressed consent. Since Jesse was opposed to trying it and Andrew couldn’t, Barry finally gave in and agreed to go along with them. In addition to the three little one, Trey, Vinnie, Graham, Sammy, Ted, Cole and Carlos would also be going with me.