Pt 7: Lisa's Caribbean Holliday

Story Info
Pt 7: Lisa sails the holidays with her favorite men.
6.2k words
4.85
4.8k
9
0
Story does not have any tags
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
WyrdWilly
WyrdWilly
151 Followers

I was able to get us a forty-one foot catamaran for the trip, and arranged for boarding at the same marina Lisa and I used on our first trip. Now, having some experience with what to expect, I told the guys that we'd be landing and getting to the boat shortly before sundown, and that we'd spend the first night in the marina.

We arrived and all went mostly according to plan. We got snorkeling gear, food, water, ice, fuel, and other essentials at the market, and went to the same little restaurant we tried out the last time Lisa and I were there. It hadn't changed much, and the food was great.

We all retired to our boat, the Fanta-Sea, and by my insistence, we kept things calm and uneventful while still in the marina. There would be time enough for everything when we were sailing from island to island.

Morning came with fairly strong winds, and we had a hell of a time with so few experienced sailors. Several of the guys got a little sea-sick, but Lisa had become quite the sailor over the last few years. She gave them Dramamine and encouragement until we finally dropped anchor in a sheltered cove among other sailboats.

We all prepped the boat for the night, got our flippers and masks, and jumped in for some snorkeling. The magnificent clear waters and beautiful reefs were always exciting, and we swam around to enjoy the sights and relax from the sail.

It wasn't long before Todd swam up behind Lisa and pulled the tie of her bikini top free.

She laughed about it, took it off, and tossed it at him. "You have to hang onto it then." She said. "Don't lose it."

"How about the bottoms?" Eric asked.

She untied them and tossed them to him. "Yours now. Don't lose them. I mean it."

We swam some more, everyone sort of following my naked wife as she made an incredible mermaid. It seemed we had the reef to ourselves, but suddenly there was another couple swimming by. At first they were still just enjoying the reef. Then, the man of the pair realized Lisa was naked. He made a sort of doubletake, and Lisa saw him do it. She fluttered her fingers at him in a cute little wave, and just slowly swam by.

He followed her with his eyes, tentatively checking to see if his partner noticed. Eventually she did, and also did a doubletake, but she didn't seem to keep on following Lisa.

We made our way back to the boat, and Lisa was laughing about the encounter as the guys made imitations of the man's face and his efforts to look, without looking. It was a great start to the vacation.

Lisa, already naked, decided to stay that way. We had dinner aboard the boat that night and enjoyed some drinks in the evening. Then the fun started.

Henry caught Lisa by the hips as she was walking past and pulled down onto his lap. She pretended to resist at first, then allowed him to have her. He just held her for a while, then whispered something at her. She got up for a second, and he pulled down his swim trunks. She sat again, and he rocked her back and forth with his cock rubbing her pussy.

The rest of us just made idle comments about it and kept the conversation going. It felt completely natural and friendly. Nobody was trying to get in on the fun, no move to swarm her with hands and cocks. It was just all of us casually aware that Lisa was everyone's and anyone could have her. No pressure. No urgency. We had twelve days, and we would all have our time with my insatiable wife.

Eventually his cock teasing got her so wet and turned on, she shifted up, grabbed his shaft, and slid herself down on him. They fucked slow and sensual for a change, and Lisa seemed to enjoy it. She made soft cooing sounds that I've only ever heard during our slow, romantic sex.

"Oh, god Henry... that's so nice." His hands gently caressed her beautiful breasts, making her gasp quietly as she approached her climax. She came with her adorable love howl, and all the guys teasingly howled with her... especially Henry who came almost at the same time.

There were four bunks on the Fanta-Sea, so it was doubles for everyone. Of course, Lisa and I were together, and the guys made the best of pairing up. It was late, and sun and swimming takes a lot out of you, so Lisa and I were the first to head off to bed.

As soon as we were alone, Lisa came on to me and said, "It's our first night here. Don't you think we should start it right?"

I agreed and we had some nice, long, gentle love making. Lisa came in quiet gasps and soft moans, trembling like a leaf as she stared intently into my eyes. As her orgasmic high subsided, she kissed me and whispered. "This was a wonderful surprise... and I think this will be the best holiday ever."

She went to the head and cleaned up, then came to curl herself into my arms again. I awoke several hours later, no idea what time it was, but the sun hadn't come up, and Lisa was sucking my cock to life. I brushed my hand through her hair, and she lifted her smile at me that I could barely make out in the dark. "I hope you don't mind." She whispered. "I just really needed your cock."

It was one of those rare moments of intimacy laced with pure lust. Her mouth was nothing short of magical. Her tongue slid out under my cock, stimulating the most sensitive spots as she eased more and more into that silky heaven. Her lips kept getting higher and higher on my shaft, until she was pressed right against my pelvis. She slurped her way off and flashed me a victorious smile. "I did it!" she exclaimed. "I deep throated you!"

"Been practicing without me?" I asked.

She giggled. "Been forced to practice with these guys." She said. "For some reason, they don't understand that my throat has its limits."

A few minutes more of her expertise in deepthroat training, and she made me cum in her mouth, gulping it down with greedy little moans, then curled herself into my arms again and whispered, "Thanks. I needed a snack." We had a little laugh and fell asleep.

The next morning, she patted my arm to wake me in whispers. The pre-morning glow was just starting to light the sky, so I knew it was very early.

"Honey?" she said pleadingly. "Could I go wake a couple of the guys?"

"Of course, babe." I smiled. "Have fun."

She lunged at me for a kiss. "Mmm... best husband ever." And she quietly left our cabin, went to the forward cabin on the same side, and I heard the door open, close, and a couple surprised groggy groans. In a few minutes, Lisa's lusty moans began, and then were smothered. Someone just filled her mouth with a cock.

I got up, new swim trunks for the day, and went up to the main cabin. I was soon joined by Henry and Eric. They listened to the moaning and thumping against the bulkhead for a minute, then Eric just said, "Coffee?"

Eventually, my wife came up and joined us on deck. She was still naked, hair a bit disheveled, and just as stunning as ever. She got a cup of coffee and took a seat on Eric's lap as if it was the most natural thing to do. We all sat at the table, sharing a simple breakfast and coffee as the sun started to warm the day.

Lisa said, "Let's swim to the shore and find coconuts for tonight before we go to the next island. We can make drinks with them."

"I'll get the swim gear." Gus said and was off like a shot.

She got up from Eric's lap and looked down at him. "Bikini?" she asked.

He made like he considered it, then said, "Nah... you look great just like that."

She bent down and gave him a kiss, then wiggled her way to the aft and dove in. We all grabbed flippers, masks, snorkels, and a few nets used to collect things while diving, which we thought should hold a bunch of coconuts.

Dave and Gus helped Lisa get her flippers on, which they seemed less intent on doing than getting a little touching. Apparently, they thought they had some unfinished business from earlier that morning.

Eventually we all went ashore and wandered into the coconut grove. It was very impressive. They were huge, untrimmed, wild coconuts, and dozens lay on the ground, mostly rotten or homes for bugs and land crabs. We found a couple that looked fresh, then spent some time throwing things at some low hanging ones to knock them off.

I collected two in my hands and went to put them in the net. There I found Lisa bracing herself against a tree while Tom slowly screwed her from behind. She saw me and gasped a little smile at me.

"Sorry, baby." She panted. "It must be this Caribbean air and water. I just needed to be fucked."

"No need to explain, love." I smiled back. "Have fun."

I left them to their spontaneous sex and helped collect the rest of the coconuts. By the time we came back, Lisa was on her knees as Tom had a hold of her hair, ramming his full length down her throat. I was a little amazed at how skilled she was becoming at deepthroating cock. We all gathered around to watch the end and it was quite a show.

Lisa looked like she was being forced to suck his cock, but I could see the smile in her eyes. She was loving every minute of this. He shoved it in deep, drew back, shoved in again, then held her mouth there a moment. I could see her struggling not to gag as he pumped his cream right down her throat, and she let out a loud gasp when he finally let her go. Still ejaculating, Tom sent ribbons of cum shooting all over her face to some cheers by the guys. Lisa got cum in her hair, on her face and breasts. She remained kneeling there, panting and smiling. Finally, she took a sample of Tom's cum from her tits with a finger and licked it clean.

Still, it remained an almost relaxed, natural tone. None of the guys rushed to take her again. Nobody made any lude comments. They all just stood watching until I helped Lisa to her feet and we all swam back to the boat.

We got back on the open water and selected the next destination. The plan was to go through customs and head for a small neighboring island for the night. The town that had the customs office had a popular restaurant, and they weren't terribly expensive, which I thought the guys would appreciate since they were buying. As we arrived, the wind started to pick up. I knew our lightweight sailors would be seasick if we continued, so we dealt with customs and took a slip for the night.

After dinner, we sat on deck and made small talk until we heard music getting louder from somewhere. Tom and Henry decided they would go check it out, and came back to report a pretty wild bar.

Before I could even ask her if she wanted to go, Lisa was hurrying down to our cabin. "Give me twenty minutes to change and put on some makeup." She said as she went.

She emerged in a baby blue one piece bathing suit that was sheer but for her breasts and pussy. She tied a wrap around her hips, and flashed her stunning smile at me. "Ready!" she announced.

We had to walk the length of the boardwalk, and then part of the beach to a little shack of a place. It looked like something rebuilt from a ruin, or pieced together from shipwreck and drift wood. The place looked seedy on the outside, but when the door opened, loud music and purple lights poured out.

Lisa looked equal parts nervous and excited. She took my arm, and we went in.

The bar was a collection of surfboards assembled together. There were seats that looked like mini hammocks. Lights flashed and shifted colors as they panned around the room. There was an open space where people were bumping and grinding to the sensual island beat.

Lisa hopped on her toes with excitement. "Look at this place!" she squeaked.

"Wanna dance?" I asked.

"Of course!" She grabbed my hand and pulled me out there with her. She's at least six inches shorter than me, so I had to get low so we could grind properly. I had her rubbing her pussy to my bulge, and we were both really getting into it. Then a pair of hands came around her and cupped both her breasts.

She looked over her shoulder to find Eric smiling back. She turned to give him a kiss, then returned to grinding with me as he kept feeling her up.

After a while, I left them still dancing, went to the bar, and Tom took my place. Lisa was, once again, completely loving all the attention. This went on for a while, my lovely wife being groped and grinding away, while the others in the bar seemed to be slowly getting louder and more daring.

There was a cheer nearby, and we all looked to see a dark skinned cutie toss her bikini top to the bar and started dancing topless with a couple eager guys.

"Oh, of course." Lisa sighed. "The one place on the island where I could go topless, and I wore a one piece!"

"Don't let that stop you." I said, and she lifted a shocked look at me. "You have a wrap. Just... slither out of that bathing suit and wear the wrap around your hips."

She got that sexy smile I love so much and leaned in close. "You, sir, are a bad influence." She lifted on her toes and kissed me, then motioned for the guys to gather around.

We all made a circle, which wasn't all that effective, but it was something. Lisa looked around, decided it was close enough, and quickly stripped off her bathing suit as lots of heads turned trying to get a look. A minute later, she stepped out of our circle clad only in her wrap and tossed her bathing suit to the bartender. There came another cheer for her, and she was quickly surrounded by a dozen guys wanting to dance with the hot American girl.

Lisa kept her dances just for us, but the grinding became something much more intense. We were going at it hard, and Gus was feeling her up and lightly teasing her hard nipples, when another cheer rang out.

Some pretty redhead MILF hopped her ass up on the bar, and lay back. The big black bartender shouted, "Body Shots!" and everyone started to gather around.

The redheaded woman reached her hand to a guy who was probably her boyfriend or husband, and he moved up to her. The bartender asked, "Top, bottom, or middle?"

"Middle." She said.

The bartender nodded to the man she was with. "Ready, man?"

He leaned down and got his face right over the redhead's belly. The tequila poured, and he lapped it up with slurps and sucks as she laughed and wiggled around on the surfboards.

Another girl, closer to Lisa's age, whipped off her shirt and jumped up on the bar. Her tits were unimpressive, but she was enthusiastic. She grabbed a young guy who was with her, and then the bartender. "Top and you get Middle." She smiled, and wriggled herself flat as she waited.

The young guy looked a little intimidated, but he got into position at her tits while the bartender positioned herself over her abs. The tequila poured, running down her chest faster than the boyfriend could keep up, and the bartender lapped up the rest, making the girl squeal.

Lisa lifted her eager smile at me, and I didn't even need to hear her ask. "Of course, you can." I said, and she hurried to the bar.

This resulted in a surge for the bar. Everyone, it seemed, wanted to see my little wife get a body shot.

She turned to hop up, but I got her by the hips, and lifted her like a dancer on a stage. She sat up, and asked the bartender. "I assume bottom is..." and she glanced down at her pussy.

The bartender grinned and nodded.

She beamed a smile back. "Excellent." She scooted a foot or two toward the end of the bar so she could hang her legs over the side. Then she reached a hand for Gus, and said, "Top." He moved to her side over her firm breasts. "Umm... Middle." She took Todd by the hand and pulled him over. "And bottom." She smiled at me and pointed. "Darling, would you hold my wrap so it doesn't get wet?"

I removed her wrap, and the whole bar erupted in a raucous cheer as my hot little wife lay back, completely naked. The bartender got the tequila ready and checked that we were all in position. He started to pour over her tits first, and Gus dove in eagerly. The pour traveled down over her belly, and Todd lapped up what he could. Then the pour ran down her belly, and continued over her pussy. I engulfed her pussy in my mouth, sucking and drinking as I ate her out.

The cheers were deafening. This went on for about thirty seconds, and the bartender reluctantly stopped pouring. "Sorry, man. All I gave give ya on one pour."

Lisa reached up and gently turned his face to her. "Can I do another?" she asked sweetly.

He smiled back, and nodded. "Sure, baby. Same three?"

She shook her head. She reached out for the guys. "Henry, you're top. Dave, you're middle, and Eric, you're bottom."

Another cheer rang out when they realized this little hottie was doing three different guys. They took positions and Lisa cried out as they all licked and sucked at her. The bartender poured a bit longer than the first time, and Lisa was squirming and panting by the time it was done.

"That was the hottest body shot I ever poured." The bartender told Lisa quietly.

"One more?" she panted at him.

He grinned. "You have more?" he said, looking out at the crowd.

She nodded. "Tom, honey." He stepped forward, and Lisa sat up, leaned over to the bartender and whispered to him. He scowled and shook his head. She pleaded and whispered at him again. His eyes went wide, and he nodded.

Lisa swung her legs over and slid off the bar, then pointed at Tom to take her place. "Up you go, handsome." She said.

Tom looked confused, but he turned and hopped up. She looked down at his trunks, smiled up at him sweetly, and said, "Bottom."

The gathered crowd made a collective moan of anticipation. Was she really going to do this, right in a bar full of spectators?

Tom somewhat bashfully tugged his trunks down and lay back. The crowd gathered close as his cock sprang up.

Lisa got into position and nodded. The bartender poured tequila over Tom's exposed cock, and Lisa tilted her head sideways to catch what she could while running her mouth and tongue up and down his shaft. It was a sight to see, and the crowd was definitely getting ready to go crazy. When the pour ended, Lisa licked her tongue up Tom's cock, then gulped him into her mouth to the sound of cheers, gasps, and shouts of encouragement. I could tell by the way she was going at it, she really wanted to finish him off there on the bar, but the bartender whispered something and she slurped off Tom's erection with a reluctant final kiss on his swollen head.

With a tequila drenched crotch, Tom got up and Lisa licked her lips and grabbed Tom for a quick kiss before he left the bar.

I reached for Lisa, but instead of her coming to me, she pulled me to her. She reached up and wrapped her arms around my neck. "I'm sorry, love. I had to make a deal to get that last one. I know it was wrong, and you can punish me later if you want."

"What deal did you make?" I asked.

She looked back over her shoulder to the big black bartender, and he unzipped his fly letting a massive cock roll out of his shorts. Lisa gasped when she saw it and licked her lips. "Um, I sort of promised him a blowjob."

"Did you?" I grinned down at her. "You really are such a slut, you know that."

She nodded. "I am." She said. "Sorry."

I lifted her up and kissed her deep. "Have fun, love."

She beamed her smile up at me and rounded the bar with her adorable tiny steps. At first there were just a few guys following that hot babe with their eyes, then they saw her get to her knees behind the bar, and a shout rang out. "She's blowing the bartender!"

In seconds, a crowd had formed around the bar to watch. I couldn't see much, but I got a pretty good idea of what was going on by all the comments and the bobbing motion of the top of Lisa's head.

"Oh shit! Look at that ass. She so fucking hot!"

"She'll never fit that whole thing."

"God, what a sexy thing. She really loves cock."

"Oh my god, she's deepthroating him. Look at her neck bulging."

"She's gagging on it. Geeze, let the slut breathe!"

Another cheer went up and by some stroke of luck, I had a clear view of the finale. He grabbed Lisa by her hair, and rammed his cock down her throat a few more times, then pulled back and emptied such a huge load, it looked like she'd gotten a pint of cum dumped on her hair, face and tits.

WyrdWilly
WyrdWilly
151 Followers
12