St. Croix Vacation

That evening we had a most enjoyable meal with Sharon and her adult daughters, Amanda and Connie, on their boat. They prepared a great meal, certainly a challenge considering the small size of the galley. We had brought a bottle of wine with us as a gift and this, along with 2 others that they had, lubricated the conversation.

They gave us a tour of the sailboat and explained a bit about how they cruised the Caribbean. Liz seemed particularly intrigued. My sailing experience was only on small craft in the lakes of our home state of Minnesota. Liz and never been sailing before.

"You guys have been so kind to let us use your shower, how about if we return a favor," said Amanda. "We're taking a day sail over to Buck Island to the national park and stopping in Christiansted on the way back to top off our fuel tanks. Why don't you join us for the day. That way you can help sail the boat and Liz can find out how much fun it is to sail."

Sharon and Connie chimed in their approval of this plan. That settled, we agreed to be ready on the beach early, at 6am, so they could pick us up in the dingy for the adventure.

With this plan in place we decided that we should not stay out too late and made ready for our return to our house.

Sharon decided that she would stay on the boat to clean up after dinner while Amanda and Connie would ferry us back to our villa.

Amanda cut the engine as we drifted the last few yards to the beach and I swung my legs over to step out and hold the boat. I could hear music coming from the pool deck next door. Connie heard it too.

"Sounds like they're having a party."

"Those are our friends and neighbors, Karen and Jerry. We only just met them this week but have enjoyed getting to know them."

Connie looked toward the sound and laughed. "We've seen them a couple of times as we've past by. I take it they appreciated the privacy that you all enjoy given how much of them we've seen."

"You know, they told us to offer an invitation to swim if you wanted. Do you want to be introduced?"

"That would be great," said Amanda. "A swim in fresh water would be great."

We started toward the steps leading up to the pool deck. Liz went a little ahead of the rest of us, I'm sure to check to see if we might be interrupting anything.

"I guess you're already aware that they, like us, have adopted a clothing optional attitude here in our little bay. I hope that doesn't dissuade you."

"Jeez, Jack," laughed Connie. "I don't think that will be a problem since we've already been naked together."

Since Liz continued her ascent of the stairs I took it to mean that Karen and Jerry were just relaxing on the deck. Karen was getting up from her lounger as we got to the pool deck and came over to greet us. She had snatched up a towel from the seat as she stood.

"Don't' worry with that," said Liz. "These are the young women we told you about earlier from the sailboat. They're okay with the whole nudity thing. In fact, that's how we were all dressed or undressed when we first met."

Shaking hands, Karen introduced herself. "Jerry is playing cabana boy and went in to make some drinks. He should be out in a second. I'm glad you all stopped by. Please, make yourself comfortable. The pool is perfect temperature so feel free to jump in. Jack, be a dear and see if you can give Jerry a hand and bring something for everyone. We've been enjoying some gin and tonics if that's okay with you all. Good? Excellent."

I turned to go into the house while the women continued to get acquainted. I found Jerry in the kitchen.

"Hey man, Karen sent me in to help."

"Good to see you. Let me grab a couple more glasses."

"Better make it 4 more, I brought guests, Amanda and Connie are the two young women from the sailboat we told you about earlier."

I found the ice while he opened up another bottle of tonic water and got some more lime slices from the fridge. Jerry poured everything into a pitcher and I carried the glasses on a tray back out to the pool deck. The women were still standing together talking.

They turned as we came out of the house and I could see Amanda and Connie both stop and stare as Jerry approached, his dangling prick swinging back and forth.

"I don't know about you all," said Liz, "but I'm going to jump in for a second and cool off."

She was out of her dress in a flash, made easier by the fact she wasn't wearing anything underneath. I set down the tray of glasses I was carrying and stripped down too.

The two sisters looked at each other inquisitively then with smiles, shrugged t-shirts over heads and shimmied out of tight shorts to join in our little band. Both Jerry and Karen gave approving nods.

I introduced the girls to Jerry since he'd been inside with me. I found it interesting that, rather than shake hands, he leaned over to each to give European style cheek kisses to both. He did the same to Liz, his long dick swinging against her upper thigh.

It felt great to get wet in the pool since it was somewhat muggy outside and soon all 6 of us were in the water but I was also ready to enjoy a cold libation and the G and T's were calling. I climbed out to act as the drink waiter. Having filled the glasses I carried them over to the pool edge on the tray to serve the others who waded over to the pool side. Karen would reach onto the tray and pass one to one of the others while reaching back for the next glass. The tray was virtually in my lap as I squatted on the pool deck and, as she reached for the next glass, Karen's hand missed and ended up wrapped around my cock.

"Oops," she quickly laughed. "I'd better pay more attention to what I'm doing."

I tried to be nonchalant and shrug it off but my cock had a different idea and started to become engorged my the unexpected touch. By the time the last drink had been passed out, it was pointing straight up. I jumped in the pool to hide it and cool it down. I'm sure the women had seen my predicament but at least no one made any comment.

We paddled and dunked while we drank and talked. The drinks seemed to go down very quickly and no too much later Amanda and Connie pulled themselves out to head home.

"Now be ready early," advised Connie. "We want to get out on the early side so we'll dingy to your place at around 7am. Karen, you and Jerry are welcome to join us for the day sail if you'd like."

"Thanks for the offer, but we've got some bank meetings in the morning and the way things move down here we can afford to try and reschedule it."

Both women gathered up their clothes but ended up just carrying them in their hands and walking down from the pool deck to their dingy in the nude, a most pleasant sight.

"One more?" asked Jerry, rattling his glass.

"I think yes," answered Liz, "then we need to get to bed if we're going to be ready for the morning.

As Jerry went inside again, Karen moved over to the shallow end of the pool where Liz and I were standing.

"I'm sorry if I startled you earlier when I grabbed your cock."

"No problem. You were doing a couple of things at the same time. I'm sure it was just an accident."

"Maybe it wasn't," she whispered, mainly toward Liz. "I hope this doesn't make you angry or hurt our new friendship but I kind of did it accidentally on purpose. You've seen Jerry, he's particularly well endowed but sometimes its almost too big. It makes it difficult to go down on him and when he fucks me there's not a whole lot of change in the position and stimulation."

I looked Liz directly in the eyes to see her reaction to this unexpected shift in the conversation.

"Karen, you're right, Jerry has one of the biggest cocks I've ever seen and I've never touched one that size ever. We need to be honest, we watched you going down on him the other night in our hot tub and then I was coming up to your pool yesterday and saw you guys screwing on the deck lounger. We've gotten pretty hot watching you guys and trying new things." She glanced back at me. "I've wanted to wrap my hands around that cock on your husband since I first saw it just to see what it feels like and I'm sure Jack, here, would appreciate the same attention from you."

Karen agreed. "Let's go for it."

Jerry had come back out to the pool with the drink tray and Liz got out to go help him.

"What's everybody looking at?" he asked.

As he stood with the tray in his hands she reached out to wrap her fingers around the meat hanging between his legs, her thin fingers barely able to encircle it girth. I thought he was about to drop the tray of drinks. She led him by his prick over to the lounge chairs and after setting down the tray she had him lay back on the chaise. Kneeling to the side Liz began to methodically stroke and fondle Jerry causing him to engorge to massive proportions. I was frozen in place at the sight of my wife stroking someone else.

"Why don't you sit up on the edge of the pool?" Karen said to me.

I hoisted up, knees hanging over the edge in the water and she moved over between them and pushed my chest indicating that I should lay back. I was hard in an instant, her wet hands stroking the length of my cock. I looked over to watch the action on the lounger. Liz's eyes were transfixed on the python in her hands. One hand worked up and down the shaft while the other played with the balls in his shaved nut sack.

Feeling Karen's hair over my cock I look down in time to see her mouth envelop the purple swollen head on my own organ. Her mouth was silky smooth and her tongue lapped and explored around its head. Liz glanced over to see what was happening by the pool and with a wink from me opened her mouth to try to take in his monster. It was almost too big for her to engulf. She ended up just licking up and down the shaft while rubbing it against her cheeks and lips.

Meanwhile, Karen was giving me a memorable blowjob. She expertly probed with her tongue and applied just enough suction to stimulate without causing me to spew too quickly. Her hands continued to work the shaft and fondle my balls. The feeling on my cock combined with the vision of my wife wrestling with Jerry's monster prick sent me over the edge in no time at all.

"I'm cumming," I grunted to Karen and began to shoot my hot jizm across her face and hair. From the sounds that Jerry was making I could tell he was about to go off too and Liz's hands began to fly up and down his dick as he also ejaculated. The globs of sticky cum landed on her chest and she used his big cock to rub it across her boobs.

We all got back in the pool to wash up a bit and I'll be honest there was some tension in the air as we had stepped across a previously unchallenged boundary. Since we were due to get up early for our sailing trip we gave our thank yous and goodbyes and headed back to our villa.

"That was unexpected," said Liz as we strolled back along the beach still nude.

"I guess we need to talk about what happened," I said. "I just need you to know that I am totally dedicated to you and to our wonderful relationship. I've never wanted to be with anyone else but you. Even though what we just did was with other people I couldn't help but think about being with you."

"I have those same feelings. Honestly, now that I've seen and touched a cock that size I've had my fill, so to speak. It would be more than I could be comfortable with. What I like is right here."

She stopped in front of me and reached around my back with one arm while the other reached down to my own cock which began to swell again. Her lips met mine and we kissed and hugged passionately on the beach in front of the house.

"We'd better get to bed if we're going to have any fun tomorrow."

Even with the late night and alcohol, we both woke the next morning excited about our sailing trip with Amanda, Connie and Sharon. We packed a couple of bags of snacks and drinks to share with our new friends and I put my camera into its dry bag to take as well.

Liz wore a tropical print sarong over one of her more brief bikinis and I slipped on a speedo style swimsuit and some surf shorts over top of that. I knew we'd be stopping in town on the other side of the island and wanted to be able to wander about some of the shops. Liz had taken our stuff down to the beach awaiting the dingy while I grabbed towels and sunscreen. Amanda pulled up to the beach just before 6 am. She had on a white hooded cover up that came down to just below her hips. Rather than have her take more time to pull up on the beach we waded out to meet her in about 2 feet of water. Amanda leaned over to give Liz a hand up into the boat, bracing one leg on the side of the inflatable. It was impossible not to notice that she was bare beneath her cover up. Her shaven pussy was only a couple feet away from my head as I held the boat steady. I jumped on board and we were soon motoring to the yacht.

After boarding I helped Amanda secure the dingy and hoist it up on the davits. Connie, dressed in a colorful bikini, was forward working on the anchor line. Sharon, I presumed, was still below. There was hardly a whiff of breeze here at the anchorage and Amanda moved to the cockpit and started the engine to move us ahead so her sister could pull up the anchor. I went to the bow to help out.

"The weather report is for fair skies and light winds," she informed me. "I hope we'll get some wind early so we can put up some sail. I really don't feel like I'm doing the right thing if we're just motoring but, since we've got a bit of a schedule, we need to get things going."

The movement of air from our forward motion was a relief. It was going to be a very hot day and I was already drenched with sweat from the little bit of exertion I had done. Connie had me help unzip the sail bag for the main sail and, with her guidance I cranked the halyard to raise the sail.

Amanda was at the helm, "There's not much wind yet but we can motorsail and be ready if something does blow up."

We settled into the cockpit while Amanda gave us a tutorial about sailing the yacht and monitoring the engine. Connie was busy moving around the boat straightening lines and securing hatches.

"Where's Sharon?" Liz asked.

"Oh, I'm sorry I forgot to tell you," said Amanda. "Mother decided to stay back at the marina to do some laundry. She said she needed some private time which, you can imagine, if nonexistent on the boat. She also said she might take advantage of your hospitality to go back to your villa for the shower."

"Oh, I wish we'd known to let her have free run of the house. She's welcome to go inside, use the deck and hot tub or anything else she needs. Is there any way to contact her?"

"I'll try her on the cell phone and let her know," said Amanda. "I told her she'd get bored sitting at that marina all day."

We were successful finding Sharon on the phone, glad to know that she'd have a place to hang out for the day.

The boat was pointed toward the mouth of our little bay and Amanda changed places with me giving me the wheel.

"Just keep us on this heading," she instructed, pointing toward the compass. "We're headed directly through the channel and we'll go a ways out before we turn back along the coast."

She grabbed Liz's hand and together they moved to the bow to join Connie. I kept us on course while they worked on lines and stowed some other gear. Connie knelt down into a forward locker and pulled out some padded mats which she then spread out on the deck and snapped into place.

All three girls sat down facing forward enjoying the early morning sunshine. There was hardly any chop to the water as we passed the point of land marking the mouth of the bay and as we headed toward the open water I watched Amanda slip her white cover up over her head. As I had guessed she was completely naked under it. Connie immediately followed her lead, her bikini off in a flash. I had to smile as Liz did the same, stripping off her own suit. Connie gathered up all their clothes and walked back to the cockpit to stow them below deck.

"I'm sure you don't mind," she smiled at me as she passed. "It's not like you've haven't see it all before. Since we've got to get dressed again when we get to town I don't want to risk having something blow overboard on the way."

A smile spread across my face watching her walk back to the front of the boat to join her sister and my wife where they sat together applying sunscreen. I kicked off my own bathing suit and tossed it down into the cabin. It was hard to imagine a more idyllic setting, sailing on the crystal clear water of the Caribbean with a crew of beautiful naked women lounging in front of me.

After a short time, Connie and Liz stood up and worked themselves along the edge of the deck to join me in the cockpit. Connie came to relieve me at the wheel.

"There's a little wind coming up and we need to set the genny sail up front and better set the mainsail. We're going to do a course change too so if you want to move up by Amanda she'll tell you what we need you to do."

Scrambling up to the bow I took my place by Amanda as she handed me a line.

"We're going to quickly raise the genoa sail. Together we'll pull this line with the hand crank winch as it unfurls from the forestay line then I'll tie it off."

We took hold of the winch handles on each side of the crank and with a nod from my teacher began to crank the line out. Watching the sail deploy was difficult since the view of Amanda's tits shaking from side to side while she cranked vied for my interest. Once tied off she directed me back to the cockpit area where we prepared for a tack to starboard. The boat came around as Connie turned the wheel and, with a hand controlling the line to the mainsail, the boom slowly swung around. Together, Amanda and I trimmed the sail and tied off the line.

"Excellent job, rookie," said Connie. "We've got some decent wind now so I'm going to shut off the engine and we'll just be pure sailors."

She stayed at her position at the wheel and Liz and I followed Amanda back to the front of the boat. Since it was still morning we were able to get plenty of sun on the deck even with the foresail out. I stretched out on one of the mats to let Liz spread sunscreen across my back. I listened casually as the two women chatted, enjoying the sensation of my wife's hands spreading the liquid across my skin. I gave a start when I felt two more hands sliding across the lower part of my back. Peeking through my nearly closed eyes I found Amanda kneeling next to me across from my wife helping with the lotion.

Liz's hands continued to spread the lotion across my skin as she moved down and massaged the oil into my butt. I wondered if Amanda was going to follow suit and , after hear my wife say "sure, go ahead, I think he'd like that" a second set of hands did the same thing to the other cheek.

When I laid down I had tucked my cock into a position where it was pointing down. With the sensation of two beautiful naked women massaging my own bare ass it began to swell and extend further down between my legs. I could feel Amanda's fingers as they spread the lotion between my legs and a moment later she was running them along the underside of my now rigid prick.

"Don't you think he should turn over so we can do his other side?" my wife asked Amanda.

"Most definitely, he's got a great tan and we wouldn't want him to burn."

I think Liz was initially just teasing me knowing that I was now sporting a huge hard on. I don't know if it was the tropical environment or the chance to respond to my wife's challenge but I decided to just go with the flow. Rolling over, my cock was pointed straight up, laying against my belly.

"I looks like someone's enjoying the attention," said Amanda with a smile.

The excitement of this blatant exhibitionism made me swell even more. Liz placed her fingers around the turgid shaft and lifted it up and out of the way so that Amanda could spread the lotion across my lower belly. A smile spread across Liz's face as she let the swollen member slip out of her hand, bouncing against the back of Amanda's.