Chapter 15: Entertaining the Remaining Housewives and The Orgy

“Wow, Lennie, you’re up kind of early today, aren’t you?” DJ walked out of his office, now considered her office by the girls, as she spent more time in it than he did. Lennie was working out in the gym a full half hour before his trainer, Matt, was expected to arrive. He was running on the treadmill at a faster pace than he usually did, and sweat was pouring from his brow. She had her Bluetooth headphones set on. Lennie looked at her for a second, thinking only half-jokingly, Does she wear that thing when she sleeps?

“Yeah, DJ, I couldn’t sleep, so I figured I’d get some extra work in today. It can’t hurt.” He realized how early it was, did a double-take at the dressed and awake DJ, and asked, “Me up early? What about you? Heck, it’s 6:30 in the morning, and you look like you’ve been up for hours.”

“Yeah, I had to get up early this morning because Maria wanted to talk, and she is in Hong Kong right now. She had an all-nighter, and it started at 10 p.m. local time, so I just finished talking with her a few minutes ago. She had scheduling conflicts coming up, and I needed to know her preferences. After all, she’s the superstar, and what she wants is more important than what the clients want, right?”

“Yes, the girls should get what they want. Hell, who am I kidding? They always get what they want,” Lennie scoffed at his own comment. DJ smiled and nodded in agreement, but the look on Lennie’s face was nothing like hers.

“Why the sour face, Lennie? Oh,” she said, answering her own question, “Cindy is gone again, isn’t she? It’s the semi-annual get-together with the Dollar Brothers. I’m not sure if you’re aware, Lennie, but until you joined, the Dollar Brother meetup always lasted at least five days, sometimes a full week. This time, it’s only for two and a half days. They were kind of pissed when I told them, but Cindy was adamant about cutting it short.”

“Really?” Lennie was surprised.

“Yeah, she is balancing her time between clients so she can be back home with you and us girls; she told me that.”

That made Lennie feel a bit better, knowing that she was trying.

“She said she is combining that event with another one of her regular events, a three-day session with Jackson Haggarty. She cut that one short as well. He wanted her for a full week again, but she had me be the fall girl and tell Jackson I had messed up and double-booked Samantha, so he only got half the time he wanted with her. Of course, he figured I was lying to him, but he didn’t question me, other than muttering a mumbled word I thought I heard was ‘bullshit.’ She didn’t say anything specific, but I have a hunch it was to get back here to be with you more than she has.”

Lennie was surprised at her comment but still confused.

“I thought she was just in the Mediterranean with that Haggarty guy for a week and a half, and now she is getting with him again?” Lennie was pissed when he said it. This fucking Haggarty guy has been with her more this month than I have, the bastard. I’ve never met him, and I already despise the guy.

“Lennie, before you were around, we all thought that she was finally going to break her own rule and marry the guy, especially after she and Lori broke it off. Taylor, Kaylani, and I speculated that Cindy didn’t marry Lori because she was going to marry Haggarty instead. It’s like she had this biological clock inside her that said she had to get hitched. But she didn’t, of course, and less than a year later, she meets you, and BOOM!, she changes her feelings about him just like that.”

“You’re kidding, right?”

“Not at all. I’m only speculating, but when talking with Jackson Haggarty, I think he resents you for sweeping her off her feet.”

“Really?” The comment caught Lennie off guard.

“Yeah, it’s just a vibe I’ve picked up in the last six months from him when he calls and sets up time with her. He’s still nuts for her. In the last couple of years, she has been with him far more often than any of her other clients. Samantha has made at least a few million off him in that time, maybe more. I’d have to check to know the exact amount. Sometimes, she would be gone with him for a couple of weeks at a time. You should see her passport. She has two standard 28-page passports, both fully used, with a hole punched in them to indicate they are no longer valid. She keeps those in her desk at her condo as souvenirs. A couple of years ago, she applied for the larger, 52-page passport she uses now, and until you came on the scene, we thought that it would be full by next year. My girl likes her traveling, you know. It’s almost always by private jet, and she stays at some of the most amazing villas or beachfront properties when she isn’t on one of her client’s yachts.”

“That sounds so very upper class,” he scoffed.

“Lennie, I don’t think you realize just how rich many of her clients are, and therefore, the girls of the escort service get paid. I think one has a private island in the Caribbean. I mean the entire fucking island, and it has a small airstrip where a smaller jet can land. It features a huge villa with white sandy beaches and year-round servants. It comes with its own marina with a breakwater for year-round use and dock space for a dozen big yachts, as well as another dozen good-sized sailboats. I’ve seen pictures and videos Sam made, and they’re impressive.”

Lennie was rethinking his earlier comments.

“Others have giant waterfront estates on the Mediterranean, in Hawaii, and in other locations where the rich and the famous hang out. Some have literally thousands of feet of beachfront. Not to mention, I think she said that combined, our clients have at least six giant yachts, Haggarty’s being the largest. All of them either have their own private jets or are provided with one by the company or companies they run. Do you know that Haggarty has just purchased a new Boeing jet? A 737 custom configured for business executives? Cindy sent me a few pictures of it a few weeks ago, and it’s amazing inside, complete with fancy leather seats, couches, and sleeping pods only found in the international-sized 777s. It even has two bedrooms with queen-sized beds. Upper-class, you say? Lennie, I don’t think you have a real idea of how upper-class her clients are.”

DJ’s response didn’t make him feel any better. His mind drifted, and he thought that compared to them, his net worth was a pittance. Suddenly, he didn’t feel as rich as he had felt just yesterday. DJ saw the look on his face.

“Lennie, you’ve got to stop comparing yourself to them. You are incredibly successful, so take pride in that. I mean, with that new big contract Dan landed, you are in the top one-tenth of one percent now, and after a couple of years, you’ll be in the top tenth of the top tenth. That is pretty amazing, Lennie. I mean, just a few years ago, you were driving for Uber to pay your bills, right?”

He nodded and smiled, but still, it bothered him. Until now, he had never thought this way about his net worth, even years ago. Then it hit him: it wasn’t the money. He was comparing himself to the man whom he had beaten out of the race for the affections of the woman they both loved. He was worried about keeping her affections, not his growing wealth. Lennie only wanted money so he could buy anything for himself or his friends, not to keep score with the rich and famous.

He stopped pacing on the treadmill, his routine finished. It was like DJ could read his mind.

“Lennie,” DJ said as she stared directly into his eyes, “you make plenty of money. Cindy doesn’t compare your balance sheet to others. She wants you because of who you are.”

Lennie paused for a moment and then, looking into her eyes, said, “DJ, how, at 27, did you get so smart?” He smiled as he said it.

“I learn things quickly, Lennie. That’s just who I am,” his compliment graciously accepted. DJ changed the subject to more immediate matters, knowing that Lennie would dwell on the current one, to the detriment of his and, therefore, the girls’ attitudes.

“So Lennie, what did you think of Melody and Candy?” she said, her voice upbeat and naturally cheery.

“What a pair!” he replied. “They really like to push that twins thing, don’t they?”

“Sure, why not? It is something that can’t be duplicated, and for a lot of men, having twin girls for a roll in the hay is a fantasy they can seldom enjoy in the real world,” she said. “Tell me, when you saw their videos, you were intrigued, weren’t you?”

“When I saw Melody’s, I had to immediately watch Candy’s, and I was hooked. I can’t imagine hiring one and not the other after that.”

“Which is exactly why they created their videos that way. It was Sam who thought of that. She’s so smart,” she added, and then realized using her name could get Lennie back in his funk.

“So what did you think about the other thing?” she quickly asked.

“What thing?” Lennie asked, not changing his attitude.

“The thing about them being heterosexual but cleaning each other up and snowballing your cum,” she answered, “you know they don’t really like to do that very much. They told you, right?”

“Yes, they did. The twin thing, though, sets them up in the client’s mind to do it, because having two beautiful women at the same time almost assumes they are bi, at least to me. I guess they got used to it, though, because they sure were convincing.”

“They are performers, Lennie, and they perform. Whatever the client wants, that’s what they do. All of Sam’s girls are the same way.”

Late in the afternoon of the next day, DJ silently walked up behind Lennie, who was reading his laptop, and said, “Lennie.”

He jumped and said, “DJ! FUCK! Don’t do that!” He balked, perturbed that she got him again.

DJ giggled, once again successful. “So, Lennie, in a couple of days, you have your final meet-up with the rest of the housewives. I think you’ll enjoy being with them.”

“DJ, I’ve enjoyed every encounter so far. These women are all different but also beautiful and are very sexual beings. Never in my life have I had so many young, beautiful women want pleasure and please me like these girls have.”

“Of course, Lennie. And none of them have ever had a pimp, either,” DJ responded. “A Romeo pimp, one who loves all of his girls, is special.”

Lennie nodded and smiled.

“When Cindy and I set this schedule up, we wanted you to meet the girls in a kind of order. We think we’ve saved the best for last. You want to know your stable of girls, right? I mean, that’s one of the main reasons you are doing this.”

“Of course, I do. I’ve learned a lot already.”

“That’s great! It means everything has gone as planned. You know the rule, that other than us girls who live with you, everyone else has to be married?”

“Yeah, and I’ve been told that it is because single girls have boyfriends, and in the past, there have been problems with boyfriends trying to control them and causing other problems.”

“Exactly. It was before I was here, but I’ve heard some stories. Anyway, these girls are the first, second, and fifth housewives Sam ever hired. The first one started twelve years ago. They not only love their work but can offer you history and perspective about the escort service, and Sam, for that matter, that none of the other girls could.”

Suddenly, Lennie dropped his thoughts about Haggarty and felt better. DJ had a special talent for changing men’s minds.

“So, Lennie, the last three girls are Michelle, Shelly, and Danielle, but everyone calls her Dani. Fiona manages Shelly, and Maria manages Michelle and Dani,” DJ said.

“Wait a minute. Twelve years, you say? Maria has only been with Sam for five years, and Fiona has been with Sam for a bit over two. That doesn’t make sense.”

“It does when you understand Samantha’s thinking. Because they were single and the three housewives had been here for years and were experienced both physically and emotionally as prostitutes, Sam figured a sort of ‘reverse training’ would work well. And it has,” DJ said.

“What do you mean by ‘reverse training’?”

“The students taught the teacher, so to speak. When Sam found Maria and Fiona under less than ideal circumstances, both were messed up and had no idea how to control their encounters because of their extreme abuse and their young ages. I’m referring to how your stable acts with a client, the basics of being a high-end call girl, like all of Sam’s. Those two were literally raped thousands of times under the control of pimps in their teens and early twenties. They both thought that rape was normal sex. You know their histories. They’ve never even had a regular sexual encounter. God, can you even imagine growing up like that?”

DJ shuddered as she said it and paused for a few moments when she saw the saddened look on Lennie’s face. She stared at him until he nodded for her to continue.

“When Cindy first met them, they mostly just lay there and became numb, waiting for it to be over. Neither girl even knew that during sex, their pussies normally self-lubricate. They were always dry.”

“Ow! I’m not a woman, but I can only imagine how much that could hurt,” Lennie blurted out.

“Yeah, Maria told me that one of her pimps would use cooking oil as lube sometimes. Can you imagine how horrible that was?” DJ had a sour look on her face to match Lennie’s wincing.

“They would turn their minds and senses off to shield themselves from the pain. Good sex, as you know, is an explosion of the senses and a great way to communicate with your partner, verbally and non-verbally. It provides an emotional and physical reset. For them, they had no idea sex could be fun or exhilarating. And as for communication, who wants to know about a different john once every half hour? It was really sad, to be honest. Those pimps mentally beat them down and abused them. How men could be so evil as to destroy the kindness they had inside of them—there is a special place in hell waiting for them,” her voice snarling as she said it.

“Damn,” Lennie responded, “when I heard of what happened to them as teens, I always wondered how they somehow turned into the exciting, dynamic, sensual women they are now. So, it was those three that changed them from beaten-down young women to the sexy babes they are today?”

“Yeah, and it took a long time for them to finally understand how different rape was from real sex and all the benefits that come with it. Neither had any idea of how to provide a sensuous encounter with a man. These three experienced women, having become skilled lovemakers over the years, taught them the ropes. In a way, they literally saved the Mexican and the Irish women to find their inner selves and become loving adult women. The three wives had the experience. It took a long time, but the transfer of knowledge went well. I mean, look at Maria and Fiona; they are amazing whores providing incredible sexual encounters to men, right?”