Chapter 10: Yachting in Ibiza, Spain

Author’s note: A personal confession, my imagination enjoyed writing this chapter. A lot. I hope you enjoy it. And if you would be so kind, give my story a rating how you like it so far, it is at the halfway point with this chapter. Oh, and another big tip of the hat to my editor, Twins56. What a magnificent help she is! Thanks, N!

Lennie heard a knock at his bedroom door. He looked at the clock, and it said 9:45. Had he overslept that long?

“Uhh, come in,” he mumbled. Last night, he had participated in Taylor’s gangbang, and he was feeling all of his 67 years.

“Hi, Lennie,” DJ’s cheerful voice said. “You are normally up way before this, but you’re still sleeping, so I’m here to bug you. I just have to know what you thought of the gangbang with Taylor last night. Were we girls exaggerating her prowess?” The smile on her face was almost wicked, she already knew the answer from talking with dozens of men that had experienced a Taylor gangbang before and raved about it the next time she talked with them.

“Oh, god no. If anything, you undersold the insanity. Taylor was in charge of a dozen horny, Viagra-filled men that she drove to just this side of crazy.”

DJ giggled loudly. “So you enjoyed it, then?” she grinned at him with a devilish smirk.

“I didn’t oversleep for three hours for nothing. Taylor wore me out. Hell, she wore out a dozen men, all of whom were younger than me. She is so sexy and classy, too—well, as classy as a gangbang whore can be. She would go from cute and sweet to completely owning three naked, horny guys at a time.” He shook his foggy head. “And to think I doubted if she could drain a dozen horny guys so completely that none of them could get it up. Foolish me. I will never doubt that girl again when it comes to anything sexual.”

“That sounds like a testimonial, Lennie. Make sure you tell her,” she opined.

Lennie looked at the bubbly blonde who broke into his bedroom. “By the way, is she around? After the gangbang, she visited Ernie, her client, you know, Slurpy. She never stops!”

DJ laughed again. “Glad you enjoyed the festivities, Lennie. Yeah, she got back a little before sunup, and she will probably be up and about early this afternoon. Now, you can look the clients in the eye and tell them you were there. I get clients all the time who brag about being in one of Taylor’s gangbangs. Now, do you see why she wanted to experience one firsthand and not just by word of mouth?”

Lennie only nodded. He was still worn out. He slept naked and looked down at his feeble, worn out cock. He wondered if he would ever be able to get it hard again. DJ continued by talking about the reason she had come to see Lennie in the first place.

“I’m here to get you back on schedule with the housewives. You still have five of them to be with, you know. I was texting Cindy late last night. She’s in Ibiza, Spain, right now, and we agreed that it made sense to change the schedule so you could finish with them. After all, you are already behind schedule, and you still need to evaluate the finalists for the additional ten new girls for the Consumer Electronics Show coming up in January.”

Lennie moaned. “You know, DJ, never in all my days would I ever think I would complain about having to have sex with so many beautiful women. But listen to me. Frankly, I’m embarrassed by myself.”

“Don’t worry, Lennie. Cindy came up with a new idea that I agreed made sense. How about this: we schedule one session with two housewives, and then another with three of them. Two sessions, maybe four days apart, and no sex for three days to let you rest and recuperate from Taylor.”

That sounded good to Lennie. “Yeah, I like that, but what about the girls? You know I won’t be able to come in each one of them. I’m not Superman.”

DJ smiled. “Of course not, Lennie. Just do what comes naturally. Ha,” she said to Lennie, “get it, what comes naturally.” She giggled as Lennie groaned. “More than the sex, they all want to claim they have been with their pimp. Besides, your oral talents are what the girls all talk about. The ones that haven’t had you yet are looking forward to that tongue-and-finger action you have become famous for. I will personally attest to that.”

“Famous? Okay, if you say so. Yeah, I can do that. In fact, it sounds like a lot of fun. I have been with all of you girls quite a few times already, and I survived that, remember?”

“Yes, Lennie, I remember. I was there all of those times. So, it’s a plan, then?”

Lennie nodded and rolled back into the bed, sleeping for another two hours.

Samantha, Skylar, and Jackson had landed on the island of Ibiza, Spain, in the Mediterranean Sea. A playground for the rich, famous, and infamous, the party scene was at its height for the fall season. The three walked off Jackson’s new Boeing 737 Business Jet, which landed on the island, and walked over to a helicopter that took them to the yacht. In five minutes, it was landing on his giant yacht’s helipad, and the billionaire stepped out, his gorgeous personal assistant on one side and his magnificent paid girlfriend on the other. Both were wearing tiny micro bikinis, large floppy hats to protect themselves from the sun, and giant, stylish sunglasses.

“Oh, Jackson, this is perfect!” Samantha cooed. “The yacht is moored to overlook everything! Thanks, Jackson, I approve.”

San Antonio, the main town the locals knew as Sant Antoni de Portmany, was located on the western coast of Ibiza. Positioned along the coast, the view of the famous Sunset Strip—called Ses Variades by the locals—offered prime views of the Mediterranean facing west. It also provided great views of the action at the giant pools and sunny beaches, especially from the top deck and flybridge of Jackson’s giant yacht.

Jackson smiled. He was happy when Samantha was happy. “Let’s say hi to Captain Kirk, ladies. I’m sure he will want to see you two. And I’m sure he will be happy to see Maria as well. She will be here in two days, and then after a final day here, we will be sailing to Corsica for three days, an Italian island about two days’ cruising time from Ibiza, so we are going to take it slow. After another couple of days’ stay, it will be onward to Cannes, France, completing our week-plus vacation.”

“Oh, Jackson, this sounds great!” Sam enthused. They walked off the helipad and up a dozen wide steps to the flybridge of the giant 113-meter superyacht. Including the flybridge, the yacht had five different decks. It took 16 crew members and a very experienced captain to operate it. There was room for eighteen guests and a large sun deck for twelve people to lie in the sunshine, acquiring amazing tans, in addition to deck seating under shade to protect from the scorching Mediterranean sun. Of course, there were over a dozen separate berths, all with queen beds except for two king beds, and 16 separate bunks in 8 additional rooms for the crew.

The flybridge had a movable canvas top that allowed either sunshine or shade when the weather became too hot. For most of the trip, the canvas would be up, and either the captain or the first mate would be piloting the massive yacht. While it was in port, the canvas was stored away so the sun on the flying bridge could be enjoyed. From the hill high above that looked down at the marina, one could look down towards the bow and plainly see anyone sunbathing on the large deck directly below, especially the three world-class beauties that would be making the trip. They would be nude for the crew to enjoy, but only Jackson and Captain Kirk would get to enjoy their lovely bodies and nasty charms. At least, that was the way it was in the past. Jackson had an idea to thank his crew for consistently doing such a fine job.

“Hello, Captain Kirk,” Samantha demurely said as they stepped onto the flybridge. “How is my favorite starship captain?” she giggled. “This yacht of yours reminds me of the Enterprise. I’m a big Star Trek fan, you know.”

“Why hello, Samantha,” he greeted in his slow, Southern drawl gained from growing up in his native Louisiana, with a warm smile. “How is my favorite world-class beauty? I haven’t seen you since last year. Let me look at you for a minute,” he said, stepping back a few steps and giving her a long stare down her nearly naked body, and then slowly back up until he looked directly into her eyes.

“Come here,” he beckoned. Samantha stepped forward and gave him a deep, slow, wet kiss as his hands roamed aimlessly over her skin, feeling her tight ass, her back, up to her shoulder blades, and back to her butt again. She knew why she was there, and gave the captain anything he wanted.

Half an hour before, she checked the SES app to ensure that the captain had followed proper testing procedures. Sharon had contracted with several nurses and doctors in other parts of the world to perform her strict testing procedures. Kirk had one of those doctors visit him just a week before, a continuation of his constant testing regimen. As she expected, when she looked up his record, the background was green, indicating that anything sexual could be performed without protection, just like with the man paying for everything, Jackson.

“I’m so glad my owner lets me sample his precious merchandise. God, you are beautiful.” He glanced at Skylar, who was nearly naked with the new micro-bikini she had bought when the two women were in New York and visited an exclusive swimsuit boutique. Letting go of Samantha, he repeated his slow investigation of Jackson’s personal assistant. When he first became Haggarty’s captain of his mega-yacht, he was surprised that his owner was so free with him enjoying his women, but he didn’t question it. Captain Kirk could have had nearly any woman swimming in the resort pools of Ibiza. However, he preferred the absolute female perfection that the shipowner had brought with him on his needed vacation.

“And did I hear it right, Sam, that Maria will be joining us again, like last year?” he queried.

“Yes, Captain Kirk, she will be here in two days.”

“I can’t wait! The three of you have to be the most beautiful women in the world. Jax, you have to know that I get offers to pilot yachts all the time, and it is more than the money that keeps me working for you,” he chuckled, only half-serious. Kirk gave Skylar another smoldering kiss and then moved a step back to Samantha, where his hands freely roamed her semi-nude body. He kissed her as his hands explored her perfect skin, finally letting go and turning back to his owner.

“And Jax, I can’t wait for Maria to get here and watch one of the girls’ sexy shows. How they make love to each other is freaky. I like freaky, gorgeous women,” he drawled in his Louisiana accent.

Formerly an ensign in the US Navy, Jackson met the captain one day as a teen when he was a groundskeeper at his local golf course. He became his caddy and younger friend. Jackson, being rich and influential at age 30, sponsored young Kirk as a reference to get into the US Naval Academy. They remained friends for life. With the new yacht being built, Jackson lured him away to pilot his superyacht with a salary that was three times what his salary and retirement were in the Navy.

Jackson had to pull some strings with the Secretary of the Navy to ensure Kirk wouldn’t suffer negative consequences by withdrawing from his commitment to the Navy. The quarter-million dollars Jax had to repay for his naval education was covered with a simple check. One of Jackson’s companies built cutting-edge electronics for Navy ships, so he got to know every Secretary of the US Navy, as they changed after each presidential election. It was up to the Secretary alone to grant any early release of a senior officer class person before they retired from a complete career, as the Navy had a lot invested in each person at this senior level. The decision was informally granted after playing 18 holes one day with the Secretary of the Navy. It did cost Jackson something important: to willingly lose to the Secretary playing their golf game.

The Navy leader knew Jackson was a fierce competitor as well as a scratch golfer, and the Secretary was proud of his single-digit handicap, which he played to a 7. Jackson’s losing to an inferior golfer demonstrated that he was serious about wanting Kirk to captain his soon-to-be-launched megayacht. It still took a year for it to happen officially, as there were rules and procedures, you know.

“Captain Kirk, who says you have to wait for Maria to watch pretty women get their freak on?” Samantha purred. She looked at Skylar, and the two micro-bikini-clad women moved to each other and started to slowly and sensually kiss. Their hands roamed each other’s bodies, getting reactions like only another woman could know. Their kisses were slow and wet. Sam’s hand slipped to Sky’s breast and, after softly fondling it, slipped lower until her hand was between Sky’s legs. Her hand deftly passed inside the scrap of cloth and slowly started rubbing Sky’s pussy, already getting wet from anticipation. Sam flicked her hardening clit, causing Skylar to squeak and gasp, and causing Captain Kirk to groan.

“Fuck, Jackson, will you look at that? Fucking crap. I ain’t seen nothing that hot in a long time,” Kirk muttered, staring at the amazing scene.

“I told you, Cap, my women are dreams come true. Party as much as you want, and change to a confident girlfriend with brains and experience—these Sam girls are unique. The only problem is that none of them will leave their lifestyle and take my riches. So I take the next best thing: pay for more and more of their time. All of the girls, I should call them what they are, whores, are unique, but at the same time have the same high standards and expectations.”

Captain Kirk burst out in laughter at Jackson’s comment about the beautiful women.

“Yeah, it’s funny to use the words ‘whore’ and ‘high standards’ in the same sentence, but it’s true. I’ve never known a whore, much less a group of whores, to be trustworthy and caring of my personal interests. That’s why I will never get married again. Hell, I already have five kids with my three ex-wives. Only the first one didn’t have a prenup, but then I got smart. But still, comparing 100 days a year of Sam’s girls, the retail is $48,000 every 24 hours. That’s a little less than 5 million a year for all the loving pussy I can handle. That’s a helluva lot less than the alimony I pay to each one of my three babymaker ex-wives. Some, like Sam and some of her girls, are tried and true, like putting on an old jacket that fits perfectly with age, and others seem to get younger and younger. What a mix of heavenly beauty. That’s way cheaper than any of my divorces, and the experiences are divine.”

Being on the top of the flybridge, nobody on the yacht could see the women going at it. From some of the buildings high on the shore, however, they could be seen with the naked eye, and with a set of binoculars, they could watch the sexy show with amazing detail. To the women, it mattered not who was watching. Both of them were getting hot, and not from the outside temperature.