WBDP - Caribbean Cruise

"Is that how you know Brianna? From the auction?" I asked.

"No, I met her a few years ago when I had my piercings done."

"That's how we met her," I said. "Marcia had her piercings done by Brianna." I remembered how Marcia had her piercings done and wondered if Gigi's were done the same way. Mr. Happy started to make an unwelcome appearance.

"The reason I made contact with Brianna and asked to meet is I'm shooting in St. Barths this week, but I have the rest of this evening and all of tomorrow off. I was hoping I might impose on you and Marcia to get together and have some fun, like Bella."

"Aren't you dating that musician guy, Zayn something?" I asked.

"Zayn Malick and it's been kind of an on again - off again romance. It's off at the moment."

I looked at Marcia and she shrugged her shoulders.

"You're not on my free pass list," I said.

"Bella mentioned something about that. She said she wasn't initially on your list either, but you removed someone else and added her."

"Wouldn't it be kind of awkward at Thanksgiving, Christmas, some of the other family togethers?"

"Awkward how? What are you talking about?" Gigi asked.

"Knowing that you and Bella both fucked the same two people. I mean, I suppose you could compare notes and all, but you don't think there'd be some issues."

"I don't know. It's never come up before."

"I know if we should see you both together sometime, it would be weird. Not that I'm expecting to meet all your family together, but just strange, you know. Let's say we were somehow able to get together in the future, and both you and Bella met us somewhere, like at Brianna's. What if you want to get together again, and Bella says, 'hey, I'm in to. I had a good time'. Do we fuck each of you separately, or both together, and if you were both there, isn't that technically incest. I know I'm talking lightning strike probability here, but that's definitely at the weird end of the strangeness scale. You see where I'm going with this?"

"I suppose. Does that mean you don't want to get together now? I could contact Bella right now and both of us could agree never to meet you again. Future weirdness goes out the window."

I laughed. "I suppose it would. Gigi. You're a lovely woman and I can safely say if we both hadn't been with Bella first, I'd willingly throw someone off my celebrity list and spend time with you. Right now, I'd have to say no. Not sure I can get past the sisters angle. I'm pretty perverse, I think everyone at this table would agree with that, but I don't know if Marcia or I could ignore that." I turned to her for confirmation.

"It is Gigi Hadid, Master. It is strange, but if you really want this, I would march down the path with you."

"Gigi, I deeply thank you for your offer. I really do. This has been an unusual time for us. A lot has happened on this cruise I never expected to happen. I believe it's best if Marcia and I decline at this moment and give ourselves time to process all we've gone through. My relationship with Marcia is the most important thing in my life. While I may kick myself in the morning, I will regretfully pass on this opportunity. I realize this may be a one time offer and I can't call you in two weeks and tell you I've changed my mind. Given that, perhaps you'd like to join us for dancing and drinking tonight. I'll understand perfectly if you'd like to decline. Believe me when I tell you this has absolutely nothing to do with you. Considering what I know about everyone else at this table, I'm sure there's not another person here unwilling to spend time with you. Let's say I don't think this is the right time for us to make this decision."

"That might have been the nicest and only rejection I've experienced when I offered to have sex with someone. If you're declining my offer, I'd prefer returning to my room and drowning myself in ice cream. I'm unaccustomed to rejection." She laughed to show that she really was okay. "Thanks for the invitation though."

"You have a great evening. Who are you doing the photo shoot for?"

"The French edition of Vogue."

"I'll keep my eye open for it so I can look at you and tell myself again what a fool I am."

"You do that," she said, laughing. "Good night everyone. Have a good time. Chantelle, tell Brianna I'm sorry I missed her. Give her my love. Mr. And Mrs. Thornhill, can I expect to see you at New York fashion week this fall?" I just realized that given Bill's money and Evelyn's clothing budget, they were probably honored guests at fashion week.

"That's still up in the air," William replied. "We haven't made up our minds yet."

"Nice leash and collar, Mrs. Thornhill. You missed a spot," she wiped a glob of cum with her finger which Evelyn missed, licked it off, waved goodbye and left.

"Damn, she's hot," Grant said.

"She most certainly is," I agreed.

"I can't believe you turned her down."

"She's not the most important person in my life and I was reminded of something Marcia told Evelyn about our free pass list a couple days ago."

"Which was what, Master?" Marcia asked.

"That fucking someone, even on our free pass list, without the full knowledge and consent of our spouse would be cheating."

"But she had knowledge and was willing to consent, Sam" Evelyn said.

"I wasn't lying when I said a lot of things have happened on this trip, not all of it expected. Bill was unexpected, Chantelle and Monique were unexpected, Dina was very unexpected. We haven't taken time to process any of it. We've had no chance to talk about it. Communication is the key to our success. There might have been consent, but neither of us has full knowledge because we don't know how much this affected us. I prefer to slow down and ensure we're both good in all possible ways without throwing another variable in the equation."

"Thank you, Master. That was very thoughtful. I love you so much."

"And I love you, my little slave. What say we all go out and get drunk because I'm a fool?"

"You were telling the truth about being with a celebrity," Evelyn said. "I didn't believe you. Fantasies of Grandeur, I thought. But you were with Bella Hadid. Who was the other one, I wonder."

"At least Gigi didn't give her name away. I'll never tell. Please, everyone, honor Bella's request for privacy. Don't talk about this shit, okay?"

"And you arranged for your husband to be with Bella?" Evelyn asked. "He didn't even know it was going to happen?"

"He didn't know about either of them. Remember, Bella wasn't on his list. She just came with the person who was. It was a fortuitous circumstance, nothing more."

Marcia took my arm as we walked down the street. William and Evelyn walked in front of us and occasionally, she would look back at us thoughtfully. She was a smart cookie and I could almost see the gears turning as she processed the information she'd learned.

We went to what the cabbie had told us was the hottest place in town. I had to admit that the drinks were fine, though pricey; the DJ was tearing the place up and the joint was filled with the young and restless. I managed to dance several times with all of the ladies of our party. Marcia's outfit was a huge success. Lots of people talked to her about it and everyone wanted to dance with her. She tended to dance with the lonelier, nerdier set sitting on the sidelines and stayed away from the chic clique. She put a lot of smiles on the faces of those who appeared to have limited success with the ladies. She danced with a few girls who were friendly and polite, and of course any in our group who asked. Winning friends and influencing people all over the Caribbean. Dina stayed on the sober side as she was our boat ride back to the ship, but everyone else was pretty snockered before we left.

When we got back to the ship, Marcia whispered to me, "Tomorrow night, I'm all yours again, Master," before going with William back to his cabin. Chantelle pulled me into our cabin and undressed me, then shed her own clothes. Brianna and Monique were sleeping in a loose sixty-nine, looking like they could be ready for more amour at any moment. Chantelle rubbed her body against mine, dropped down to her knees and caressed and sucked my cock to delicious hardness before pulling me down on top of her and accepting my cock into the liquid velvet smoothness of her cunt. I fucked her hard until her first release, then she turned me over and rode me slow, her hips rocking over mine in a motion as old as time. Eventually, the sensations of her lovely cunt contracting and squeezing my cock overcame the sedative effects of the alcohol and I spilled my seed in her heat. When she felt my pulses cease and my cock shrink, she licked and cleaned the accumulated fluids from my prick. I held her close, our legs intertwined, until I fell asleep.

In the middle of the night, I felt a mouth on my cock and expected it to be Chantelle, but when I opened my eyes, I saw Monique, giving a creditable blow job. It turned out that Chantelle was licking her pussy instead as she satisfied me. I watched her service my shaft in the light of the moon through the cabin window until I felt the cum stir in my sack. I whispered to her that I was about to cum in case she wanted to finish me with her hands as unaccustomed as she was to swallowing male seed. She shook her head and sank her mouth lower on my cock as I exploded in her mouth. She drank my cum, swallowing every drop. When she was finished I pulled her up and kissed her. "Thank you," I whispered again. "You didn't have to do that."

"I wanted to, Master Sam. Perhaps you could do me a favor tomorrow," she whispered back.

"What favor would that be?" I asked quietly.

"I haven't been spanked for a week. Would you be so kind as to use your hand on me tomorrow?"

Chantelle came wriggling up between us. "Me too. I require a firm hand on my ass."

"I'd be happy to spank both of you tomorrow."

"Thank you, Monsieur Sam."

I fell asleep again with both Monique and I wrapping Chantelle in our arms and legs. I know that Chantelle got up around 5:30 to start breakfast. I felt her leave, but Monique just burrowed deeper into my arms and we both drifted back to sleep before we fully woke up. The breakfast bell rang and I turned and stretched, finding Brianna sleeping on my other side. I nudged her awake with an elbow and a kiss.

"Time to feed the baby. We wouldn't want the little rascal starving to death now, would we?"

I flipped over and nibbled Monique's neck.

"Rise and shine, sleepyhead. It's time to eat. You know Chantelle's been cooking up a storm for the last hour. You wouldn't want it going to waste."

She pushed against my head with her hand, mumbling, "It's too early."

I smacked her ass hard.

"Ouch, that hurt."

"Someone's spanking can start early if she doesn't eat."

"I'll get up. I'll need sustenance before you start smacking my ass some more."

"See, it's all a matter of perspective. What can seem like too early to eat becomes a perfectly wonderful time to eat when faced with other alternatives."

Brianna and Monique kissed each other good morning.

"Ugh, morning breath," Monique muttered.

"Double ugh, cum breath," Brianna answered.

We all brushed our teeth before going for breakfast. Chantelle made smoked salmon frittatas for breakfast and once again, a fabulous meal. I asked for a couple aspirin to go with my orange juice. I had a small hangover. I think every one else who'd gone out last night but Dina suffered the same fate. After breakfast was eaten and the table cleared, Sandy asked me if she could borrow the paddle.

"Who's in need of correction, Mrs. Edgerton?"

"My husband, of course."

"And what has your husband done or failed to do that requires a paddle?"

"It is my contention that he is merely adequate when it comes to eating pussy. I would like him to receive lessons from one of our pussy eating experts and I want him to be paddled while he's eating me out until I find his abilities substantially improved from where they are now."

"It may be kind of hard to concentrate on the job at hand if he's being paddled at the same time."

"That may provide the incentive he needs for rapid improvement."

I turned to Grant who stood there rather sheepishly as this conversation went on.

"You agree to this?" I asked him.

"I did whip her yesterday and had no real reason to do so other than I wanted to. It's only fair for the tables to be reversed. If she gets a better pussy eater in the process, I have no reason to complain."

"Good. Well, Monique is widely acknowledged among her peers to be the best rug muncher in the bunch. Brianna says she's never had anyone better. Now, in order to give you proper direction, she may be required to demonstrate the techniques for you on Sandy. Do you think that you would have a problem with that, either of you?"

They looked at each other for several moments. They came to a silent agreement and both answered "No" at the same time.

"Monique, are you willing to instruct Grant on the proper methods of pleasing his Mistress?"

"The more qualified rug munchers there are in the world, the better is is for all womankind," she answered, laughing.

"How long do you think that it should take for Grant to learn what he needs to learn, Sandy?"

"Hmm. No more than a half hour I would think. By then he should either be very good or have an ass ready to go up in flames."

"Monique, Sandy expects a much better pussy pleaser in a half hour. If she does not have one, I shall hold you responsible and you can expect your own spanking of fifty swats with that selfsame paddle. If you do your job well, I will reduce your spanking to twenty-five. Are you ready to accept your challenge?"

"Yes."

"Chantelle. It will be your job to encourage Grant to learn. As Monique will be busy demonstrating said rug munching, you must apply the paddle to Grant's ass. If he fails to learn within a half hour, you also will be responsible and will get 50 swats with the paddle. If he's a quick learner, you will get twenty-five instead. Will you accept the challenge?

"Oui, Monsieur Sam. He will learn quickly or he will not sit down for the rest of the day."

"Hey, before this little contest starts," George asked, "what beach should I head to?"

"Anse de Grande Saltine," we all shouted. "Full nudity."

"I should have known," he muttered.

"Where were we? Ah, yes, not sitting down for the rest of the day. That's the spirit. The challenge is set. Everyone take your positions. Sandy, lie down on the mat and spread your legs. Grant, get between those legs and pay very close attention to Monique. Keep your ass in the air. Chantelle, get behind him and provide him all the encouragement he needs to properly service his Mistress."

They quickly took their positions. "Beginning time, now!" as I set the timer on my watch. Of course, everyone else wanted to watch. Nothing like a good contest involving acts of sex to get everyone's attention. Chantelle immediately brought the paddle down on Grant's ass. I almost think he missed what Monique was saying to him as the pain penetrated to his brain, but he quickly brought his attention back to Sandy's cunt. After listening to Monique intently, he started licking Sandy. She would critique what he was doing, sometimes stopping him and demonstrating herself before allowing him to continue. Every thirty seconds, Chantelle delivered another smack to Grant's ass. Sandy had her first orgasm after six minutes. Monique would demonstrate another technique and Grant would immediately try it. Sandy had her second climax after five more minutes. Monique pushed him aside and using her fingers in conjunction with her tongue, had Sandy cumming again in four minutes. Grant followed her direction and had her going again in 4 1/2. Monique pointed out other erogenous zones accessible with his tongue, fingers, lips, and hands while he licked her cunt. He cut the next one down to four minutes. When fifteen minutes had passed, Chantelle started spanking his hairy buttocks every 15 seconds and with five minutes to go, was spanking him once every 10. The amount of time that it took him to get Sandy off steadily grew lower, but still hadn't gotten down to three minutes when I called time.

"Now, the matter of whether Grant is better than before is probably subjective and I'm sure that Sandy would say Grant is better now than thirty minutes ago. But is he substantially better? It took him just over six minutes for Sandy to have her first orgasm. I think Grant can objectively prove he is a better pussy pleaser if he can give Sandy her next orgasm in three minutes. That would be half the time of her first. I know that Sandy has been warmed up by the orgasms she has enjoyed for the last thirty minutes, but he had not gotten one as quickly as three minutes before time was called. Monique, step away, Grant you are on your own. You have to bring Sandy to orgasm in three minutes without assistance. Grant, I suggest you put all that you learned together. Chantelle, don't spank him while he attempts this. I'm timing this. Get ready, get set, go," starting my stopwatch.

Grant went at Sandy with a vengeance. One hand was squeezing and mauling her breasts, twisting and teasing her nipples. His other hand was engaged in putting fingers in her cunt, her ass, and sometimes both at once as he licked every square inch of her cunt, sucked and licked her clit, while nuzzling her liquid folds with his lips. He could feel the seconds ticking by and did everything in his power to bring her to orgasm.

"Fuck!" Sandra screamed. "I'm cumming. Oh, you cunt licker you. You're making your Mistress cum."

I stopped the watch as soon as she said the word 'cumming'. When her orgasm settled down and she quit shivering and moaning, I announced, "One orgasm in two minutes, fifty-three seconds. We can safely say that Grant has moved closer to lesbian territory with his cunt licking. Would you agree Sandy?"

"God, yes. That was fucking fabulous."

"There you have it, boys and girls. One more accomplished rug muncher added to the population. All women may now stand up and cheer." Of course, they all did.

"You did a fine job, girls, in getting Grant to this point. As previously promised, you will only be subjected to twenty-five swats of the paddle. Bend over the table, please. Monique on the left and Chantelle on the right."

I took my place right between them.

"Make it a good one, Monsieur Sam. I would not want to be disappointed in your spanking."

"I concur," Monique added. "I almost wanted to lose I needed this so much."

"I don't think you'll have to worry about the quality of my spankings, ladies. Just ask Marcia."

I smacked Monique hard and she jumped, squealing.

"Just like that, Master Sam," she said, grimacing.

I applied the next one to Chantelle's athletic hind quarters, if anything harder than Monique's.

"Merci, Monsieur."

Back and forth I went from one to the other. I had to admit to a certain amount of curiosity. I know what would happen to Monique's ass as she was spanked; it would go from pink, to red, to redder. I had no idea what would happen to Chantelle's ass. Could it get red? Would it get blackish red, would it just get darker, would it get lighter? I had no earthly idea, never having spanked a black ass before. I would soon find out. I'd spanked Monique with my hand before, out by the pool on Brianna's estate, but this was the first time using a paddle on her. In ten strokes, she had a healthy dark pink tone to her skin. Chantelle's skin got reddish undertones to start, but then got darker as the flood of blood rushing to her ass mixed with her skin tone. By twenty strokes, both of them were dancing on the balls of their feet. Monique was moaning, half in pleasure, half in pain. On the twenty-second stroke, she climaxed and I gave her the last three immediately. Chantelle's ass was more muscular, and I think she suffered more from the same spanking, but she was holding back her groans, merely grunting with each stroke as she danced.