The Cruise Day 04

On Day 4 of the cruise, the ship docked in St. Thomas. The island was stunning, with ancient mountains overlooking the crystal clear waters of the Caribbean. The four of us had decided to book a sailboat, and it was our idea to sail to a quiet cove called "Secret Harbour".

Since it was clearly labeled on the maps, I am not sure about the 'Secret' part, but the pictures certainly looked breathtaking. I had sailed a lot during college and after, but I wasn't sure I could handle a big sailboat by myself, so we hired a captain from the charter company, and planned to set sail within a few hours of the cruise ship getting into port.

Christy wore a black bikini with a white beach wrap over it that was just see-through enough to show off her body. Her daughter Lisa wore a bright pink bikini top with running shorts and running shoes.

I had recently started dating Christy after her divorce, and my son had started dating Lisa. Since everyone seemed to be getting along, John had traded rooms with Christy. Since Christy and I had the balcony room, we got the better end of the deal. John didn't seem to be complaining, though.

At one point, when Christy was alone with her daughter, they traded stories, and Christy admitted to me that Lisa and John were both sore from two days of pretty much nonstop sex.

Christy and her daughter both had dipped into exhibitionism on the balcony, and as a result, we had each caught the other couple at least once. The sailboat seemed like another opportunity for a great adventure, but we were a little worried about having a captain on board.

When we got to the boat, we were pleased to see that the captain had brought his own girlfriend, so that he wouldn't be trying to "steal" one of ours. The boat was a Hallberg-Rassy 46 named "Current Address". The HR is a well-made Swedish sailboat, and it might have been a little small for three couples for a whole week, but for a day cruise it was plenty big enough.

The captain was named Dave, and his girlfriend was named Jen. She apparently was a local hottie who was a fuck buddy of his, but was also a good enough sailor to help Dave whenever he had a charter that couldn't (or wouldn't) share any of the work. She had a dark complexion, and exotic features that hinted of a mixed race background. She seemed to speak English and Spanish equally well, and looked stunning in a small T- shirt and cargo shorts.

As we set sail, we were not even out of range of the port when Lisa asked Jen if it was OK to take her top off.

"Sure," Jen replied. "But you may want to wait a few minutes. People on shore with big-ass cameras can still see us pretty well."

"Fair enough," Lisa said, as she took her top off. Lisa was athletic and muscular, and almost as tall as John. She had girl-next-door good looks, and a quick smile. Her breasts were larger than Christy's, and she had that particular form of "hotness" that comes with being fresh out of high school.

When I first met her, I had not thought of Lisa as being super sexy. It might be because she was so athletic, or it might be because I was dating her mom, but the way she casually took off her clothes had an effect on all of us.

Dave and John and I all stared at Lisa's body as she made her way toward the front of the boat, and started putting on sunscreen. Jen laughed and poked Dave in the ribs, but he made no attempt to stop looking until Lisa laid down.

"You can all go naked if you want," said Dave. "Especially you." He poked back at Jen, although not nearly as hard as she had poked him.

Jen poked her tongue out at him. "I thought you invited me because I am such a good cook."

Dave smiled at me. "She is, too. The rental includes a sandwich lunch, but Jen said she would make us some grouper."

John had been standing next to us, but he headed up to the front of the boat to lay down next to Lisa. Before he laid down, he made a point of getting a handful of sunscreen and rubbing Lisa's breasts carefully.

The boat was really not designed for sunbathing. The area where they were laying was off to one side a bit, but the headsail was a relatively small jib, and it was raised from the deck just enough that it allowed people to sunbathe.

"Your kids?" Dave asked.

"Lisa is my daughter, and Johnny is Jack's son," Christy explained. "They aren't related."

"Sorry, I didn't mean to sound like I was judging," Dave apologized. "They are a cute couple."

"Yeah," Jen followed up. "You were staring at her cute couple as soon as she took her shirt off."

Christy had been standing behind me with her arms around me, giggling, but let go and said: "Well, I am going to go change then." Christy had been showing a lot of skin to start with, so the idea that she was "changing" might leave her completely naked.

Christy retreated below deck while Dave and Jen and I talked about Secret Harbour. When Christy returned, she was wearing just her bikini bottoms and deck shoes, and came up and hugged me and asked me to help her with sunscreen.

The Hallberg-Rassy 46 had a soft dodger that provided great shade in the cockpit, but it had a wide stern behind the cockpit that had been fitted with two comfortable stainless steel "railing" chairs, as well as a couple of foam mats for sunbathing. Christy spread a towel on the foam mat, and stretched out to give me the best possible view of her body.

I sat next to Christy, and rubbed sunscreen on her body, starting with her breasts. I was careful to make sure she got sunscreen all over, but I returned to her breasts repeatedly. Jen busied herself below deck, and Dave split his time between staring at Lisa, staring at Christy, making sexual innuendo with Jen, and occasionally sailing.

Since Dave seemed to be enjoying himself, we went ahead and put on a show. When Christy rolled over, I started by rubbing sunscreen underneath her bathing suit, and when she seemed to respond to my touch, I went ahead and removed her suit completely.

Christy's body was tiny and firm. Even though Jen and Lisa were many years younger, Christy had what I felt was the hottest body on the boat. Lisa was more athletic, but something about Christy's body was always wildly sexy to me. Christy played it up too. Instead of laying passively, she moved her body in response to my massage, and even turned and talked to Dave occasionally to make sure he had a clear view of her nearly shaved pussy.

Up on the front of the boat, John and Lisa seemed to be enjoying the feel of the open water. Lisa was laying sideways with her head propped up on John's chest, and her hand down his pants. John had his arm loosely by her side, but with his right hand, he would reach up from time to time and feel Lisa's breasts.

When Jen came back up from the cabin, she smiled to see Christy completely naked, and without saying a word, she took off her shirt and shorts, leaving her wearing a white speedo that looked beautiful against her dark skin.

During the winter months, the winds around the Virgin Islands are from the Notheast, and are usually steady at 15-20 knots. The winds start to change in February, and by June the winds have slowed and shifted to the southeast. Although we were expecting 12 knot winds that day, the wind gauge was holding steady at 22 knots. (This was the "apparent wind", which included the speed of the boat, but it felt like a million miles per hour.) The boat had an air conditioner below deck, but it was not needed. The breeze easily filled the inside of the sailboat.

Dave asked if I wanted to take the helm, and I definitely did. Dave had skillfully maneuvered the sailboat out of port, and he would be around later to do the hard work of getting it back in, but out on the open ocean, the boat practically navigated itself. In fact, it was outfitted with an autopilot that could function in several different ways. The autopilot could simply keep the boat on course, or if needed, it could follow a complex set of instructions based on the GPS.

Both the main sail and the jib were equipped with automatic reefing, which in this case was a switch that allowed the main sail to be rolled into the mast (to reduce the amount of sail exposed to the wind). The main sail was rolled about halfway into the mast, and the jib was rolled about halfway around the foil. The result was that the boat was not moving very fast, but it wasn't heeling over very far either. I desperately wanted to let the sails out and build some speed, and I told Dave my plans.

He went up front to let Lisa and John know that the ride was about to get a lot more exciting, and they decided to move. First I let out the main sail and adjusted it, and then I let out the jib, while Dave adjusted that. Jen had volunteered to adjust the main sail, but I wanted to get a feel for it. Once the two sails were set, the boat heeled over and started picking up speed.

Sailboats actually sail faster when they lean over, because they get a better angle on the wind. There is a compromise as to how far you can go before it gets uncomfortable, but a boat this size can lean way over without being in any danger. The GPS said our speed was only 15 knots but it felt like we were flying. The wind was steady enough that we sliced through the waves, and the water was calm enough that we were not constantly drenched with salt spray.

Lisa and John went below to get out of the wind, but the rest of us stayed on the deck. After a few minutes, Christy put her bikini bottoms back on, along with a life vest. Her breasts were smaller than the other two girls, but that life vest had never looked better on anyone.

Jen went below deck to check on the kids, and came back with a smile on her face. "Well, they are enjoying the day cruise."

The HR 46 has two beds ("berths") downstairs, with a U-shaped galley and a sitting area in between. The front area is a V-berth that they call the "VIP berth" because it makes into an oversized bed, and has a private head.

Even though there are curtains and walls to provide privacy, Jen said that John and Lisa had made no attempt to close the curtains. She had peeked up front, and seen Lisa riding John, even though the angle of the sailboat had rolled them up against one wall.

Jen had brought four beers from the cooler, and she handed one to each of us. I offered a toast, and we all drank to "fast sailboats and naked women."

After what seemed like too short a time, we adjusted the sails for a slower pace, and resumed our journey at about 5 or 6 knots, which was still plenty fast enough to arrive at the cove before lunch time. Once the sailboat flattened out, Christy removed her life vest and her bikini bottoms, and told Jen that she should do the same.

Jen hesitated, and Christy could tell she just needed some encouragement. Christy walked up to her and just casually started helping her remove her swim suit. Jen put up no argument, and got completely naked, except for her deck shoes.

"This isn't fair," she said. "Christy and I are naked, but the guys aren't."

Dave got up from the chair, took off his suit, and sat back down. He we younger than me, and taller, but his skin was wrinkled, especially around his eyes, from all the sun. I was still paying attention to the boat, but I took at least one look at him before turning back to the helm. He was already erect, and his dick was longer than mine, but not too much.

When he sat down in the stern chair, Jen immediately walked over and stood in front of him. The chair was attached high on the stern railing, and so his dick was already level with her boobs. She reached out and grabbed his member, and started rubbing it and teasing it as if they were the only people on board.

Christy came up to me and said "Now it is your turn..." I put the sailboat on autopilot and stood in front of the boat's wheel while she helped me take off my bathing suit. When the suit came down, my erection sprang up, and Christy laughed. "So you are enjoying the day cruise too."

We glanced back at Dave and Jen, and she had leaned over and was already giving him a blowjob, as he sat back in the stern rail seat. As soon as she saw it, Christy pushed me back into the captain's chair and got down on her knees. She started running her hands over my body, but there was no way I could get more excited.

After teasing me for a few minutes, she took my dick in her mouth, and started to slowly run her lips up and down my shaft. Although it felt amazing, I had been watching her ass all morning, and wanted to have my dick deep inside her.

As I pulled her to her feet, I could tell she was thinking the same thing. She crawled into my lap, raised her legs on either side of me, and lowered her pussy slowly down onto my cock. As good as it felt, I was nervous. As she was adjusting herself to me, I looked up at the controls to make sure the autopilot was still on course, and looked around to make sure there were no other boats nearby.

The island was far off to our left, but it was still visible in the distance. There were other sailboats visible from time to time, but none were close enough that they could see the sex going on. As I looked down the companionway, I saw John and Lisa looking up at us.

I waived them off. For some reason, letting Dave and Jen watch us did not feel weird at all, but letting our kids watch still seemed odd. John gave me the "thumbs up" sign, but they both seemed to get the message.

Christy had completely impaled herself on my dick, and she was limber enough that having her legs propped up against the seat back didn't seem uncomfortable. She was rocking back and forth while she ran her hands over my shoulders and back.

Although she did not have a forward view, she had an "aft" view, and she kept me appraised of what Dave and Jen were doing. "Now she is leaning over the railing, and he is fucking her from behind," Christy whispered.

The idea was incredibly sexy to me, and I strained my neck to turn around. Unfortunately, I had more of a view of Dave's ass than Jen's tits.

"Hey, pay attention to what you are doing," Christy laughed.

Christy and I gradually built up to a pretty strong pace, and I was pounding my dick into her so hard that she was coming up off the chair on each stroke. Although usually she was quiet during sex, this time she was moaning and grunting, and even added "Harder..." once.

I did my best to keep up with the jackhammer strokes, and was rewarded when I felt her orgasm approaching. Her breathing grew rapid, and suddenly she held her breath as her body tensed up around my dick. I slowed my pace, but let her grind deeply against my dick as much as she wanted. She pulled me toward her so she could wrap her lags around me.

Her orgasm lasted a long time, and she slowed down afterward, sweaty in spite of the strong wind.

While she was coming down, I felt my orgasm approaching, and started pushing into her again. She wrapped her arms around me and pulled me close again, and pushed her pussy down on me so hard that I could feel her pubic bone. I no longer had to push into her, as she was supplying all the energy. As she bounced up and down on my dick, I leaned back and unleashed my orgasm.

As she felt me pumping my cum into her, she gasped, tensed up, and rode me harder, as if she was having another orgasm. She might have been faking, but who cares. I came for what felt like forever, and I felt my dick pushing a huge load deep inside her.

When we were done, I finally put my attention back on the sailboat, but there had been no need to worry. Not only was the boat completely safe on autopilot, but Dave was keeping an eye on everything from the stern rail chair, while Jen leaned over him with his dick in her mouth.

Christie and I stayed in the captains chair, but turned our attention to Dave and Jen. Dave could see us watching, but Jen had her back to us. As I watched her head bob up and down on his his dick, I admired the shape of her ass. When she leaned down, I got a slight view of her pussy, and also a side view of her boobs.

"Wow, this view has improved since last time I turned around," I told Christy.

"Shhh," she replied. "I don't want Jen to get self conscious."

If Jen knew we were watching, she didn't seem to be bothered. In fact, Dave didn't seem bothered either. Dave had taken the base of his dick in his hand, and was jerking off into Jen's mouth. Jen had just the tip of his cock in her mouth, and would lean her head up from time to time so she could make eye contact with him.

After a few minutes, Dave let go and leaned back, and Jen changed her position so she could take more of his dick down her throat. The view of her body from the side was erotic and casual at the same time. She was thin and young, and had the muscles of someone who worked out a lot, or maybe did physical labor for a living.

"Oh fuck..." Dave moaned. He closed his eyes for a minute. The only sign that he was coming was Jen getting suddenly still, and leaning forward. I couldn't see her swallowing, but clearly there was a lot of action going on that was not completely visible. She held her breath for a long time, and when she finally came up, Dave's dick had already started to grow limp.

Christy was aroused just from watching them, and had been stroking her own pussy. My dick had also started to get hard again, but I knew from experience that I wouldn't be able to have sex again for about an hour at least.

Jen smiled at Dave, and leaned in to kiss him. Dave kissed her back, and I got the distinct impression that she let him taste some of his own semen on her lips. We she separated from him and walked back toward us, she had the look of someone who was entirely satisfied with her sexual nature, and maybe her whole life. She gave us a 1000-watt smile as she walked past us and went below deck.

Jen came back up a few seconds later and brought a towel to us. She smiled again as she reminded me: "Don't forget to clean the Captain's chair." I hadn't thought that it might be rude to fuck on the captain's chair, but we hadn't exactly been subtle.

I got some clean wipes and some water from the cockpit and cleaned the captain's chair carefully, while Christy stepped outside the cockpit and took a shower on deck. The sailboat had a "solar shower" hanging on the rigging outside the cockpit. It is basically a large bottle of water with a shower attachment on the bottom. The water heats up in the sun, and you can stand under it for a warm shower later in the day.

The water must not have been completely warm yet, because Christy didn't shower for long, and her nipples got hard and erect in the breeze. Still, she seemed to enjoy putting on a show, and when she was done, she wrapped a towel around her, and sat next to me again in the cockpit.

As we approached the harbor, John and Lisa joined us on deck, and we admired the clean white sand and the crystal clear water. As we got close to the other boats, we realized that some of the other boats might have kids aboard, so we all hastily put our bathing suits back on.

We spent the day swimming in the harbor, and we even went to the beach for a while, but we had no need to eat at the beach restaurant, because Jen prepared a meal of seafood salad, fried grouper, and fresh fruit.

On the way back to the cruise ship, the girls all quickly got naked again, but they seemed content to let the guys keep their bathing suits on. While the guys took turns steering the sailboat, drinking a few beers, and just generally having an amazing time, the girls chatted for a while up near the bow of the boat, and laid out in the sun in various poses that had all the guys horny again.

As we got out in open water, we ran the sails out again for a long sprint. While Christy steered, Jen stood behind her and gave her a neck rub. The girls had grown close very quickly, and sat together for a while and whispered, and shared e-mail addresses.