The start of a new year when the holidays are over means it’s time for the Lair men to meet and discuss our remaining cruises. I pour myself a glass of Macallan 64 from the decanter and soak up the sunshine while I wait for Kassius, Alistair, and Valentine to arrive. I head toward the reversed shaped bow of my yacht and stand overlooking the marina. I leisurely sip on the amber liquid of the refined scotch as I watch my guests begin to board on the second level. A line forms as security vets each person. Every other month, starting with January, my yacht either traverses the Atlantic or cruises to Caribbean destinations for a month. Each cruise has a theme, that is sexual in nature, for like-minded individuals. The Lair men host these coveted sexcapades. My waitlist is ridiculously long, and my selection criteria are calculatingly specific. Many have been on my waitlist since I introduced this unique experience three years ago. I have several sexually oriented businesses, but most are run by my chief executive officers. This yacht, The Playboy’s Lair, is my primary domain when I’m not traveling to check on my other entities. It is by far the hardest to get an invite on, and I only entrust the proprietary make-up of the cruises to Kassius, Alistair, and Valentine.
The chuff of a helicopter interrupts my people watching. The guys are finally here. My t-shirt flaps against my chest from the wind vortex created from the chopper touching down on the helipad in front of me. My three cousins immediately get off, already discussing some woman they shared in an orgy last night. The details are muffled, at best, because of the noise from the helicopter, but they are supplying a pretty animated visual of the event. The three of them live in different states but met up in Chicago last night for some fundraiser hosted by one of my uncles—Alistair and Valentine’s father.
“Sounds like you guys had a good time last night,” I say once they’re close enough to hear me over the helicopter’s slowing rotors. It will remain here until it’s time to take them back.
“Understatement, man. I may have to break my one-night stand rule and look her up next time I visit Chicago.” Kassius elbows me for emphasis. He never sleeps with the same woman more than once, so this one must have had some magical unicorn pussy.
“I’d love to hear all about this miraculous woman, but first, let’s get down to business.” The guys follow me to the lounge area just outside my suite and pour themselves a drink. Neither bats an eye at my exquisite choice of liquor. Macallan is our drink of choice, and the older, the better.
“So what do you have planned for this cruise?” Kassius asks. The entire planning and execution of this first cruise were solely handled by me. In previous years, the themes have been handled by these guys. I haven’t been hands-on since the very first one. “Are you doing the introduction to erotic spanking again?”
The guys know that I’m an ass man, and my kink involves leaving my mark. The belt is my favorite, but it depends on my partner and the sensation she can most tolerate. The belt is for the more experienced. Last time, my focus was too narrow. I led a class for people to experiment with long-range tools, such as the belt, but a majority of them preferred to stick with short-range tools, such as the paddle—less impact.
“Something like that. You fuckers know me well,” I chide. “I’m broadening it to impact play for the mostly experienced. I’ve accepted ten novice members, though, who have little or no experience with this type of play. I couldn’t take on more than that because I don’t want to be in teaching mode the entire cruise.”
The premise of this cruise is that thirty guests (half men and half women) thoroughly versed in the world of impact play have been matched based on their profile and preference. Each man chosen has experience in both thuddy and stingy impact play to better offer variety for the woman they are paired with. Sting is high velocity, has a smaller impact area, and is felt on the surface area of the skin. Thud is more of a penetrating blow, has a wider impact area, and is felt deeper than the skin. I have selected ten guests (again half men and half women) who are complete novices to give them an opportunity to explore their curiosities and discover which realm of the spectrum of impact play they prefer.
I explain the focus of this cruise in depth before we move on to discuss their plans for the upcoming cruises. Valentine has decided to bring exhibitionism and voyerism together while Kassius will host an orgy. No surprise there. Alistair is still undecided and is playing with a few different themes. He will need to report to me with a final decision by the time I get back in a month. His cruise isn’t until August, but we need ample time to select from the waitlist and give notice for invites. Any unavailability by those selected moves them to the bottom of the list. I don’t hold spots. My guests pay handsomely for the privilege to be included on one of my cruises, so I don’t play favorites.
The familiar sound of stilettos approaching causes the guys to pause midsentence in distraction. Only one woman has the key card capable of accessing my personal space, and that’s Tory. I wasn’t expecting her arrival until much later. She’s part of my senior leadership team, but more importantly, my fuck buddy whenever I’m aboard. Busy with a new startup in Arizona, I haven’t been on board for the last four months.
Her step slightly falters when she sees us all sitting here. She pulls at her fiery red tube dress that barely contains her tits. Her attempt to add a little more length to cover her ass nearly has them falling out. We watch in apt fascination. It’s no secret that she’s fucked us all. I may not make every cruise, but one of us is always on board. The only person her legs haven’t spread for is Kassius, and that’s because, up until now, he’s been in a serious relationship. That same relationship is responsible for his aversion to anything more than a one-night stand. I know the feeling all too well. While I don’t partake in that commitment shit, I don’t see the harm of keeping a casual fuck around if she serves a purpose. I outline my expectations and what I’m willing to offer ahead of time, and those who oppose get the boot.
Tory started as a housekeeper on my staff two short years ago. She made it very apparent that she was willing to serve more than just my cleaning needs. I’ve never mixed business with pleasure until her—my only exception. Her contributory fuck keeps us from being tempted to play with our guests. She ensures we’re well satisfied for the month we’re out at sea.
She slows her stride even more as she gets closer, unsure if we’ve discussed our time with her. She runs a nervous hand through her silky blond hair, attempting to tame the flyaways.
“Sorry, Silas. I wasn’t aware you had company. I can come back later,” she offers.
“Oh, we’re company now?” Alistair speaks up. The other two look just as amused. Kassius leans back against the chair and crosses a muscled leg over his knee. Her eyes follow before darting back among us, unsure.
“Why the formality, my dear Tory? Every single one of us has been ball’s deep in you with the exception of Kassius here.” I pat him on the chest for good measure.
“No fret, sexiness. Sharing is what we’re into, so you’re in luck. You have nothing to fear or be ashamed of. Your pussy is an exquisite unicorn that we all enjoy,” Valentine assures.
She is not at ease, and I know why. She is waiting for me to weigh in—for my approval. I wink in her direction and give her my genuine “I don’t give a rat’s ass” smile. She’s not mine. I don’t do mine. She visibly relaxes as she pushes those fake tits out in pseudo confidence. Kassius perks up at the gesture. He loves tits.
“Don’t just stand there. Come have a seat,” he suggests.
I can see the wheels turning in that mind of his. His devious thoughts are paper thin. We all give each other the look because we know where this is heading. When Tory attempts to sit beside him, he pulls her onto his lap. She doesn’t stop him.
Kassius slides a dubious hand inside her dress to cup one of her breasts, looking for any indication that she doesn’t want this. She licks her lips in anticipation, and that’s all it takes. He slides her dress down to her waist and catches a taut pink nipple between his teeth. I sip on my Macallan, happy to look on. A low moan slips from her pursed red lips as he buries his other hand between her legs. Valentine gets up and joins me on my side of the sofa. He refills his glass and settles in for the show. Apparently, he’s sitting this one out too.
Alistair isn’t sitting out, though. He stands and frees his cock before joining the scene. Kassius extends him the invitation to join by first lifting Tory enough to slip on a condom. He then wastes no time impaling her on his shaft while Alistair inserts himself in that skillful mouth of hers.
Moans and the slapping of flesh pierce the air in a hedonistic flair. My own cock stiffens to a semi from the sight and sounds. I don’t play well with others, though. I’m a selfish son of a bitch. The guys know this about me because they’ve tried to get me to join their orgies before. Besides that, I’m into some way kinkier shit, and I prefer to explore with her later, once they’re done having their fun.
I know my reasons for sitting out, but Valentine’s reason is unclear. “Had too much fun last night, fam? That mystical cunt gotten to you?” I nudge him, and he laughs.
“Impossible, fucker. No, I have plans tonight once we leave here. It’s going to be a long night, so I’m giving my dick a break. That, and sometimes I just like to watch.”
This from the guy hosting the exhibitionist-voyerism cruise. Again, no surprise there. That’s his kink. He likes to watch and be watched. No more words between us as we watch Alistair and Kassius bend Tory like a pretzel. They leave no hole unexplored, stuffing her full of their cocks. Her face flushes in an orgasmic glow as she takes everything they offer her. Every stroke has her cries of passion reaching new heights until she’s literally stuttering out the word fuck. They’ve worked her into a position of double penetration now as all three chase their impending orgasm.
Tory’s legs begin to tremble just before she falls over the edge. I knew she would be first. Neither man would allow themselves to come until she did. It’s in our guy code. Kassius and Alistair piston their hips in effortless synchrony until they both give in to the nut that was waiting to explode. They ease out of her slowly, and I feel like I should applaud that performance. They help her to her feet as she tries to make sense of the dress that is still coiled around her waist. I should have known she wasn’t wearing panties underneath. She’s sort of a freak like that. They escort her off—to shower together, I’m sure. That’s their other MO. That way they can get her to suck them off for round two. In return, they will get her off with their fingers. Once the condom comes off, no more dick is involved. I know my cousins well.
“I guess our meeting is adjourned; wouldn’t you say, cousin?” Valentine has always had a penchant for stating the obvious.
“I would say so. I would offer for you guys to stay for dinner, but as you’ve already stated, you have plans.”
We hold these meetings as more of a formality than a necessity to make sure we’re on the same page. Often, they also give us some time to catch up. Pussy has shortened this trip, but I’m confident we’re on track. I’ll get my tech guy the client list based on what we managed to discuss. Using his patented algorithm, he’ll match the guests from the waiting list per our criteria and their preferences for our upcoming cruises. I’m planning to ask Kassius to hang back for a bit longer than the other two. He is the perfect suitor for what I have in mind—for the task I omitted discussing during our brief meeting.