Lennie and Samantha - Cover

Lennie and Samantha

Copyright© 2025 by dawg997

Chapter 8

Erotica Sex Story: Chapter 8 - An older man, who found financial success later in life after enduring years of anguish, grief, and bitterness, unexpectedly meets a stunning, high-end escort at an upscale bar. Neither had sought love for over a decade, their pasts having long since closed that door. Yet, what they had both stopped believing in suddenly seems possible. Two very different worlds collide.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Coercion   Consensual   NonConsensual   Rape   Romantic   Lesbian   BiSexual   Heterosexual   Fiction   Uncle   Humiliation   Rough   Sadistic   Gang Bang   Group Sex   Harem   Orgy   Interracial   Black Male   White Male   White Female   Anal Sex   Cream Pie   Double Penetration   Exhibitionism   Oral Sex   Prostitution   Violence  

Cindy called Lennie early the next day.

“Lennie, some men would just be okay with my past and want to move on. They might have a question or two, but then forget it because they are banging a hot girlfriend. Others just want arm candy or a trophy wife, and it’s pretty much a given that they are immoral sluts or worse.”

“Not you. No, Lennie, you are the kind of man who has to know everything, at least see some real evidence that confirms your deepest fears, prejudices, or perversions. I know you keep thinking about what I do for a living. You don’t want me to escort, but you secretly want to see me in action. It will draw you in and repulse you at the same time. You have to see what I do to overcome your perversions. It’s the only way we have of creating anything close to what would be deemed a normal relationship. It’s just who you are.”

Lennie was dumbfounded and said nothing, his breath shallow and obvious. She was right.

“So, Lennie, I want you to come over to my home and show you something. Maybe this afternoon, okay?”

Lennie was at her place in a few hours. “Hi Cin,” he said as she opened the door and gave him a hug and a passionate kiss.

“Now what do you want to show me?” They walked hand in hand to the large sectional couch and sat down. She was wearing nothing but a thin, pink, body-hugging robe. It was untied, and her breasts and abs were exposed for Lennie to see.

“You know what I said yesterday about needing to see me in action. Sit down here and let me show you something on the screen.” She had a laptop connected to the wall with a long computer cable.

The 66-inch wall-mounted flat screen turned on with a click of the remote control Cindy had in her hand. The scene looked familiar. It appeared to be early evening, and Lennie was standing in her living room, his back to the camera, looking at the vista of the lake. Suddenly, Cindy appeared behind him, nude. She grabbed him with both arms and ground her firm breasts and hard nipples into his back as her mouth started nibbling on his ear. The angle was from her back, and her gorgeous naked backside was in plain view. He was aware of what happened next. It happened about a month and a half or so ago.

“You filmed us having sex for the first time? What the hell, Cindy?” She stopped the scene when he turned around and started kissing her. The scene ended before his pants were pulled down when Cindy typed a command on the computer, and another video started playing. The changes were startling.

“OK, now watch.” Lennie started to drift mentally, as if he were experiencing an out-of-body experience. It was like he was someone else who was watching the action on the big screen.

It was a video recording of the inside of her condo with the same camera angle as before. Something was different, though, he observed. The format was the old 4:3 analog TV format instead of the 16:9 HD format common today. There were black areas on each side of the picture, which confirmed it. That meant this had to be at least fifteen years old. Something else, it was the furniture! It was different from what he was sitting on. The walls were a different color. They were painted instead of the textured wallpaper they currently had. When he looked at the walls, some of the artwork in the video matched what he saw, but some had been moved to different places on the walls. And the view of Lake Washington was the same. So this had to have been many years ago.

Suddenly, a younger naked Samantha and three large, muscular black men were in the room, quietly laughing as the men’s hands roamed her hot body. Her skin was soft and perfect. Lennie gasped when he saw the younger Samantha’s incredibly firm breasts standing straight out instead of the gentle slope they had now. They were so magnificent that they looked fake, as if accomplished through the finest plastic surgeon’s efforts. The curves of her ass and waist were nearly identical to what Lennie had experienced that night, however. She was frantically unbuckling the pants of the men one by one as they fondled her. After the long black cocks were in the open, she dropped to her knees, sucking one of them while jacking the other two off using each hand.

“Fuck bitch, suck that black cock! You black cock whore!”

Between swallows, she yelled, “Yeah! Oh yeah! I’m a black cock whore. I love black cock! Fuck me with those big black cocks, I’m your Queen of Spades! Breed me like the bitch I am! Fuck a black baby into me!”

Lennie saw her left butt cheek, revealing a two-inch black spade tattoo with a capital Q inside it. He looked down at her naked left butt cheek and saw only smooth skin. He realized she didn’t have one now, so it must have been a temporary tattoo.

When she yelled Queen of Spades, the black men went crazy with lust. Each of them got rough with her, shouting obscenities as one cock after another was forced down her throat, her nipples getting pinched and twisted, her ass cheeks spanked, or three fingers jamming in and out of her wet pussy. The men took turns grabbing her roughly by her hair and forcing her mouth onto their cocks. Her mouth would go from face to face, her tongue seeking each male as they mashed lips. Once in a while, she would open her mouth, and one of the men would spit into hers. In a few minutes, her mouth went from the only orifice full of black meat, to having her pussy and then her asshole jammed with what looked like giant cocks, at least eight inches or more. She was being tossed around like a rag doll. It was so much more intense than any gangbang Lennie had seen watching porn.

The three men were tall and definitely athletes. The shortest one had to be at least 6 feet 5 inches tall; Lennie and the others were probably a few inches short of seven feet. Sam fast-forwarded the scene to get closer to the end. The three horny men kept sawing in and out of their chosen Samantha hole, and then changed after a few minutes and continued. They kept doing this for over half an hour and then worked up into a gang explosion. They pulled back, and all three holes had sperm leaking from them. From time to time, she would speed up the frames so Lennie saw the condensed version in about five minutes.

“These guys were visiting NBA players when the Sonics were still in town. I made a lot of money from NBA players until they left for Oklahoma City. Not all of them want groupies.”

Lennie recognized one of them. He had played for Los Angeles for many years. Lennie followed the Sonics until they left, well over a decade ago. The Sonics were Seattle’s first professional sports team and had been formed as an expansion team when he was in junior high school.

“After over a year with Dwayne and his black buddies, I knew what black men wanted. And damn, those NBA players could fuck for hours. Much longer than NFL players. Maybe it is their sport that does it to them; in the NBA, they are running all the time. Their stamina is amazing.”

She typed on her computer again, and the next scene was a middle-aged man walking to the old davenport. They started kissing and taking each other’s clothes off. There was no love lost; it was obvious the man was a client of a woman who was beginning an act of prostitution. In a matter of minutes, the younger Cindy was completely naked, and the man was fondling her body as his mouth crushed hers. It was strange seeing his girlfriend, completely naked and in a submissive sexual position, waiting to be entered by a stranger’s cock.

“This is about fourteen years ago, Lennie.” Lennie nodded but kept silent. “Look at the client, does he look familiar at all to you?”

Lennie was in a mild shock watching the big screen TV and a giant image of Samantha getting naked with a client. He never bothered to look at the man. But when he did, he was stunned again. It was Wallace “Wally” Fish, a local multi-billionaire who made his fortune in the PC software industry. In some years, Fortune Magazine had rated him the richest man in the world. Wally Fish was famous and had a clean, nerdy public image, too. Lennie quickly calculated that at the time of this video, he was in the national and international news nearly every week for some reason. If it wasn’t his company, it was his charity involvement. Usually appearing with his very public wife.

“Wally Fish was a client of yours? You’re kidding!”

“Yeah, for about five years or so. Other than Wally and me, nobody else knows that, except now for you.”

“What? Why are you doing this? Wouldn’t Wally be really pissed at you? Maybe do something bad to you? He’s one of the richest men in the world!”

“To be truthful, Wally is now going through a divorce, and his wife is taking him for something like a hundred billion. So the real reason it was kept secret is now water under the bridge. She still doesn’t know, Wally told me that recently.”

“Wait, you said recently? You still talk to him?”

“Oh yeah, we’re still friends, kind of. And he pays me well for those conversations, even though they are on the phone or Zoom. I’m more like a gentle ear for him over the past few years, as that bitch of a wife of his made his life miserable. He’s wickedly smart and nothing like his public nerd persona. Has a dry sense of humor; some like it, and some don’t. But the last decade or so, I saw playful and sexy drain from his eyes, replaced by darkness and drudgery as that bitch wife of his kept putting him down with her vicious digs and ridiculous demands. He would tell me about it for hours. Right here in this room, mostly. It’s not even thirty minutes from his office. He had his own code for the building door and my front door. I’d also be the flight attendant on his private business jet. A couple of times, his wife was on the flight, but she never knew about me. We spent hour after hour together in the bedroom. Discretion was critical. And let me tell you, he’s a pervert through and through.” Cindy giggled as she said it.

Lennie looked at the big screen and saw Wally as naked as Samantha, licking her butthole and rubbing two fingers in and out of her wet pussy while she moaned, kneeling on her knees and elbows as her boobs swayed back and forth. He kept being amazed watching them with her boobs firmer than now, in fact, they looked perfect, almost fake. He couldn’t get those perfect breasts out of his mind.

“But that bitch wife of his, she won’t even give him a blowjob anymore. Hasn’t in the last twenty years. She’s some prima-donna from Dallas or Atlanta or one of those southern cities with those sororities and that fake southern belle shit. Because she was from old money and a daddy with connections, Wally finally married her after he turned 30. He was pressured to get married back then. She dropped her first kid ten months after they got married. After the third kid, she cut him off sexually. And told him that if he ever cheated, she would take his money and kids away. Kids are in their teens now, and she has turned them against him.”

“It’s pretty sad, actually. He was and still is a good dad. But yeah, I talk with him from time to time. Says I’m one of the two or three people in the world he can confide in. And don’t worry, he will understand why I’m showing you this. Of course, you are sworn to secrecy. Even Lori has no idea I’ve videoed every person that’s been in here.”

“Every client? Aren’t you worried about being hacked?”

“Can’t hack an air-gapped system. See the long cable attached to my laptop? It’s not connected to the internet because the system has no Wi-Fi card. Come here to my office.”

They walked down the hall and into a room. A large monitor sat on a designer desk, a matching credenza behind the chair. She typed a code on a device in the wall, and a small hidden door opened from the smooth wall, revealing a computer server in a wire cage on a metal platform. A cable went from the computer up the wall and disappeared into the ceiling.

“Look at the computer, it’s hooked into the TV with a hard wire. And if someone were to find it and try to steal it without initiating the proper protocols, they would be electrocuted, and the entire drive array would burn to a crisp. It’s booby-trapped. Don’t worry, there are off-site backups on highly secured storage that others vaguely know of.”

Lennie was having trouble comprehending what his eyes were telling him. “Why ... why are you showing this to me?” They walked back into the living room.

“Because I mean what I say. Nobody really trusts a prostitute, so I have to show you in some other way that I’m dedicated to you, so you’ll believe me. I love you and everything I know, own, or can do is all for you, Lennie. I knew that if I ever found the man, I would have to give myself to you completely, including every secret and all of my assets. I want you to look at as many videos as you want. Here, look at the screen, and I’ll run a list of clients.”

“Hmm, let’s see”, she said as she typed in a search command on the laptop that displayed on the big screen. “Entertainers, politicians, sports celebrities, let’s take a look at who’s on that list.”

The inquiry took .0124 seconds and returned 2274 results. Cindy clicked DISPLAY, and a list appeared. Lennie gasped. Some names were listed many times, each with a different date beside it. “There are three former starting NFL quarterbacks here on the first couple of pages. And two of them are MARRIED! NBA players, MLB players! European soccer stars! All kinds of athletes.”

“Yeah, and guess what? None of them has ever been outed. Unless they are told, their wives will never know. That’s another reason why I get the crazy money I charge.”

“And look, that’s a US Senator!, and look there, that movie producer. Didn’t his movie a few years back make half a billion dollars or something like that? Geezus, Cindy, if it ever got out they were your client, they have the means to get rid of you!”

“Yeah, I’ve thought about it, in fact, have been told by a few of them similar threats. But they know I would always be completely discreet. It’s been that way since I started.”

“And they know if I mysteriously die, others whom they don’t know will spread this information to the world. I’ve had to drop a few hints that I could speak from the dead if I have to. I don’t threaten and have only said that after I was threatened. It was really just a power dance, and they knew I could play it with the best of them. Combined with benefiting from my superior pleasuring skills, they always back off.”

Lennie kept scrolling down the list and gasped as his brows raised again and again, reading famous name after famous name.

“I’m showing you this for two reasons, the first reason I already told you. You will either accept me or get rid of me after you see these videos. This is my last eighteen years for you to review. It’s my profession, it’s what I do.”

She turned to her iPad, typed another command, and the image on the big screen TV changed. A financial chart appeared showing transaction summaries. The names of all of the women who visited him, except for DJ, were listed with numbers over a million. The largest bar in the graph was labeled “House”. It was just short of $2 million. There were also ten other women’s names in a second chart, each with varying amounts, but all of them were six-figures and began with a crooked number. The largest bar on the graph by far had the name “Alexis” next to it. The bar representing her income was over $900,000.

“This is the last year of income the escort business made, and my cut of it. Now, none of the revenues I generated on my own are here, but they were well over a million in that time as well.”

She stopped typing and looked directly into Lennie’s eyes. She stared into his eyes until he realized she had something very important to say.

“Lennie, I want you to think about something. If we were together, I’d give you half of everything I own. I’d add your name to the title of my condo and my car. Your name would be added to my stock market accounts. We’d get you a fake ID and add your signature to the safety deposit boxes I have containing all the cash. Just like that.” Sam clicked her fingers. “Instead of thinking of yourself as a cuckold, if you owned half of everything I own, you’d be my pimp. A pimp gets half of his girl’s earnings. I would give you half of everything I own. You’d be my partner all the way, and that includes this business being yours - well, ours.”

Lennie was having trouble comprehending what Cindy just said. Half of everything she owns? For a guy whom she’s only known for such a short time? A pimp? Him? And half of all earnings? Just give all that money to him? Wait a minute! That sounded like marriage, right?

“I recognize Maria, Fiona, Taylor, and Kaylani, but who are the other women?”

“They all work part-time. Each one of my girls is the manager and mentor of two girls. And all those part-timers are married, too.”

Many questions hit Lennie all at once. Married? Was it true? Did the husbands know? Were they doing this against their will? He couldn’t see Cindy doing that to them. He looked at the chart and noticed that while all annual figures began with a 2, 3, 4, or 5, one of them had a taller bar graph and started with a 9. “Wow, nine hundred by one gal in one year?”

“Yeah, that’s Alex. She melts men’s hearts while taking men’s wallets. She’s relentless, too. I taught her everything she knows. She works all the time, and her husband supports her, even encourages her. The others all make low to medium six figures each year. My girls essentially supervise their activities and make sure no mistakes are made. The girls get a small percentage of each girl she manages, I think it’s currently 3 percent.” Once again, Lennie was speechless.

“We have a method we use to ensure the woman has a chance to try out working on her own so she can handle it, and then we make her tell her husband and get approval if she wants to continue. Most have some type of pressing money problem, and once the husband sees how much she is going to make, they consider it. A few of them are sex fiends, hotwife lovers, cuckolds, and such, and their wives escorting turns them on. Most of them don’t like what their wives are doing, but agree over time. If they agree, she can escort. We have an initiation, I guess you could call it, which every couple has to take successfully.”

Lennie didn’t know what to say; it was information overload.

“The first date that the husband is told of, and they are led to believe it is the first one when it is usually the third or fourth, my girl who sponsors her is with the husband when the wife goes out. My girl or I strips, teases, and gets the husband all hot, so when the wife comes home after her date, he’s sexually out of control and “reclaims” her. Then my girl joins in for a threesome to bond. It never fails. Well, rarely. If the wife thinks the husband is having regrets, my girl would aggressively intervene. It’s all about supporting the woman’s decision to be an escort for us. The husbands learn that what their wives are doing is just sex, and the wife brings a lot of money to their marriage. It’s not perfect, but we’ve only had three or four couples back out after he learns. And we have a waiting list of women who want to take their place.”

“Really? How many?” Lennie asked, expecting a few, maybe a half-dozen or so.

“Umm, at least fifty. And those are just the serious ones, who have escorted secretly already on a trial date at least once. I’m guessing three or four times that many have shown interest, but haven’t gone on a date yet.” Lennie couldn’t believe what he was hearing.

How do you find these women? And why don’t you get all hundred working, or most of them?”

“They find us. Why not all of them? Because Lennie, the girls and I are a family. We choose our clients and when we want to be with them. The housewives are there to handle overflow demand because the client base is huge. If one of my girls or I, myself, isn’t available, the client’s needs have to be taken care of somehow, or the business suffers. We five girls are the star attractions, and the housewives are there if we can’t. The client is always taken care of.”

Lennie just shook his head. This entire presentation was beyond his wildest imagination.

“We make plenty and keep it quiet and safe to protect us all. It’s simple. Our family of girls earns money by pleasuring men and women. Mostly men. We don’t want conflict in marriages, which is why we do it this way. And for the husbands, what they give up in pride and accepting they are being cuckolded, they get back money and access to one of my beautiful girls as a friend with benefits once in a while. Whatever financial problems they are having are solved.”

Lennie just stared at her, absorbing this new information.

“Oh, and a side benefit is that their wife learns how to be a true courtesan and a truly gifted sex worker. Their sex life explodes if they go along with it. From time to time, the couples come and go. Sometimes they can’t handle it, or more likely, they have exceeded their financial goals. All of them sign non-disclosure agreements about the escorting and imply it’s about prostitution, too. Of course, being illegal, prostitution makes the contract void, so that’s why we only refer to the legal escorting part. If they leave, they legally can’t talk about it. And we want to keep our family small and intimate.” Lennie slowly nodded.

“Oh, and one more thing. I’ve told you that my girls or I have never had a normal relationship with a man. In this case, occasionally, each girl gets to date two different husbands. Often they become friends, someone to be able to be with who understands them. After all, their wife is doing the same thing. It’s more than just sex. My girls win, too. It’s not a boyfriend, but at least it’s a man they can get to know, who knows what they do. Some friends with benefits, if you will. It relieves the guilt many of the wives are having, too.”

“Wow, just wow. There’s an entire communal system here that is self-sustaining, and you created it.” She beamed a big smile at Lennie, being recognized for what she built.

“Lennie, I could never split our new life and my existing life for the last 20 years. So I want to give it to you. It’s the only way I can prove my dedication to you, to us. Like that Foreigner song, I want to know what love is, I want you to show me.”

 
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