Lennie and Samantha
Copyright© 2025 by dawg997
Chapter 7
Erotica Sex Story: Chapter 7 - 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
Tears fell openly from Lennie’s eyes. The story from her past was difficult to listen to.
Cindy realized she was staring off into space as she related her story, then looked as if her mind had returned from somewhere else. She made eye contact with Lennie, returning mentally to the present from that horrible place so long ago.
“And then I had my first client. It was one of Dwayne’s regular customers, and he wanted it to be a gentle beginning. The guy actually treated me kindly. It was some white guy, about 50, who was bald and fat. I just gave him a blowjob and then got on top of him and rode him for a few minutes until he came in his condom. Then another guy, and another. I did eight guys on my first day. At first, Taylor was in the room while I performed, but after a while, men would come to Dwayne’s condo when she wasn’t there. I had to make sure they gave me the correct amount of money that Taylor told me to charge. One time I didn’t count correctly, and when Dwayne found out the next day, he beat me again.”
Hearing about the abuse was difficult for Lennie to fathom. Imagine how hard it was to take it, actually, he thought.
“I’m so sorry, baby. I’m so sorry you went through that.” He paused for a while and said, “Nobody should be abused as he did you. I’m so, so sorry for you,” he repeated.
She looked at the gray-haired man, appreciating the sympathy he was affording her, and took a deep breath to regain her composure. She returned to the story of how she became who she is today.
“Maybe a quarter of them were only blow jobs, and maybe another quarter of them had my ass as well as my pussy. I made over $6,000 in the first week. Of course, it wasn’t mine, and I did some quick math. If I could continue to make 6 grand a week, that means I would pay him back in seven months, not a year and a half.”
“I was still 21 years old for a few more months. It was a lot of money to me. And the sex with clients wasn’t that much different than what my uncle had done to me, mostly.” The look on her face noticeably darkened as she said the last sentence. She glanced at Lennie, then looked down at the floor, closing her eyes and remembering more than she wanted.
After a long pause, Cindy opened her eyes again.
“So that’s how I became a whore. Dwayne spent three days teaching me how to be a prostitute. Jerome violently raped me. Taylor was Dwayne’s top girl; Taylor was known as Dwayne’s bottom bitch. A bottom bitch is the woman who is in charge of the other women when he isn’t around. She was with or near me any time men were around, making sure I did what Dwayne or the men wanted. He chose my birth control to be an implant, which lessened the number of days I was on my period. More days to sell me, you know. I learned how to strip the way men want it to get them hot for my body, lap dances, how to give a good blowjob, how to have intercourse in different positions, and the worst was taking a cock in my ass. He set everything up.”
“At first, it was mostly businessmen visiting Seattle for a night or two, looking for a whore to entertain them or, later on, an escort to accompany them to dinner or an event. But that didn’t last too long.” There was no smile on her face.
“After a while, it got more graphic and nasty. Dwayne started setting me up with two guys simultaneously. Then three guys. Many were black. So many of them simply hated white people. They would call me cracker bitch, and yell stuff like “I’m taking my reparations up your ass, whore!” I’d never experienced that before, being hated because of my race. It was so degrading, and sometimes they hurt me pretty badly. Later, I was able to disconnect emotionally when I was working. Then, maybe two months in, I started doing bachelor parties. I would do one nearly every Friday night or every Saturday night. Sometimes back-to-back nights. There were usually at least six, or up to a dozen guys, sometimes a lot more. If there were, say, twenty guys or so, Taylor or Amber or another girl of Dwayne’s would be there too.” She paused for a moment, remembering what had happened long ago.
As she told her story, the normally positive look on her face was gone. Instead, she kept looking at the floor, back at Lennie with a disturbingly hollow look for a few seconds, and then, when Lennie looked into her eyes, would turn away to stare at the floor again. These memories were painful. She continued.
“I was completely ashamed of myself. I had no friends, the only women I even talked with were other whores that Dwayne owned. I had dropped out of school, and it really hurt not to be in class anymore. Dwayne owned me and used me to provide sex to men. We would do anything he told us to do. I had no free will. And it hurt, it was painful, at least until I got used to it. During the sex, I just remembered my dad’s face and his operation being successful.”
“By now, I was making on average over ten thousand a week, so I mentioned to Dwayne that I was making such good money that I would be paying him back in a lot less time than a year and a half. I was working 70 to 80 hours a week, and the rest of the time was for sleeping. I had no life. I went to Dwayne and said, I had already made over $60,000 for him, and at this rate, he would be paid back in another nine or ten weeks, because I had included my expenses in that. He just stared at me and laughed.”
“He yelled, ‘You stupid whore. I don’t give a shit about you breaking even. Do you think I run a charity ward? Fuck you’re dumb. Eighteen months and not a day less, you stupid cunt.’”
She paused for a moment to control her emotions and gather her thoughts. She hadn’t actually spoken to anyone about her starting days in many years, except to Lori or her therapist, and found it harder to talk than she thought she would.
“The bachelor parties continued, getting cruder by the week. I would commonly have sex with three guys at once. It’s called being airtight.” She still couldn’t look at him directly, instead staring at the floor. After a long pause, she let out a deep sigh. Lennie felt horrible listening to her story, but she was proffering it, like a confession. He wasn’t going to stop her.
“And then, believe it or not, it even got worse. Months later, Dwayne flew me to Los Angeles, and I was forced to start making porn movies. I made about 40 scenes, maybe more. It was usually two scenes a day, with different guys each time. I didn’t know anybody except for one man, whom Dwayne said I had to do whatever he told me to. It was about three weeks of work. After the shooting finished for the day, I also had to have sex with the cameraman and the sound man. A few times, I would also have sex with the makeup lady. Dwayne got paid for me making those movies.”
She took a long breath, paused, and continued her story.
“A couple of weeks after I returned, Taylor told me that I’m a ‘star’. I watched those movies as they were posted on the internet a few weeks later. They weren’t really movies but rather just sex scenes that lasted about half an hour or a bit more. Dwayne would send links to those movies to customers so he could sell me to them for more money. I was a ‘porn star,’ and he sold me that way so he could get more for me.”
She paused for a moment and then stood up. “I’ll be back in a minute, I have something to show you.” She walked down the hall and into her bedroom. Lennie stared at her naked, gorgeous body. Her ass and legs were breathtaking, the soft curves of her back and shoulders the definition of femininity.
After hearing drawers being opened and closed from her office, she returned and sat back down next to Lennie. She held a small, spiral-bound notebook and handed it to him. He opened it.
Each line contained a string of coded characters separated by commas. Lennie started deciphering it. The first was g or c. Hmm, girl or customer? After the comma, the next letter was w, b, l, a, or o. Lennie guessed that was their race: White, Black, Latino, Asian, or other. The next was o, v, a. Oral? Vaginal? Anal? The next characters were two numbers. The first was a random two-digit number, anything from 18 to 73. The next was a larger number, at least 100, but most were at least 300, some 1,000 or more. The first one must have been their age, and the next must have been how much they were charged.
“When I started, I had kept track of how many times men had sex with me. I recorded their race, age, the sex acts I performed, and the amount they paid. This is the spiral-bound notebook that I hid from Dwayne.”
Lennie looked at it, thinking that for each line, the gorgeous woman next to him performed a degrading sex act. He turned to the back of the notebook and saw a large number at the end, which was underlined twice: 1,540.
“There were 1,540 transactions. I serviced 1,540 men with my body. Five or six Johns a day, six or seven days a week. And at least one dozen-or-so-man gangbangs every weekend. In a single year. That’s the original spiral notebook.”
She stopped and shuddered at her memories coming back, as it was the first time she had looked at it in years.
Cindy started repeating herself and got emotional, but carried on with the story.
“In the last four months of my commitment after the porn shoots, Dwayne got two new girls. I had to help him turn them out and force them to do what I was doing. I had to watch and help Dwayne break them in as Taylor did to me. Jerome showed up and did to them what he did to me. Both of them, one at a time. The other one was in a back room and had to listen to the slapping and screaming happening to the first girl, so it was still a surprise what he did to her.”
The look on her face was one of sadness as she recalled her horrible memories.
“I had to watch the entire thing, even participate once in a while. They were both barely eighteen, Lennie, one still in high school, and one who had dropped out. I had to take them on dates with me and make them do all the sex acts. If they refused anything, I had to tell Dwayne, and he beat them with his belt. Then he would beat me in front of the girls, blaming them that he had to beat me. That happened at least four or five times, until the girls figured out the beatings were guaranteed if they didn’t follow orders. I used a lot of makeup to cover my bruises. And those poor girls.” Cindy paused, closed her eyes in remembrance, and slowly shook her head.
“They were so innocent until Dwayne got his hooks into them. A few weeks later, one of the girls killed herself. I found her in his apartment when I got back from a trick. She was naked in the bathtub, her wrists slashed, and an empty bottle of sleeping pills on the floor. The pills had her mom’s name on the bottle; she stole them from her. The bath water was beet red and at room temperature. Her body was ghost-white and cold. She was just lying there, her skin was this ominous pale white, the look on her face was in complete peace.”
She started sniffling, and her body shuddered as she took a deep breath. She paused for a long while before talking again.
“I called Dwayne, and he showed up maybe a half-hour later. He made a phone call, and in an hour, some men showed up, and her body and every bit of evidence about her was gone, like she never existed.”
Lennie just stared at her. Tears were rolling down his cheeks. His mouth gaped open, not knowing what to say.
“But the worst was yet to come. Dwayne had a new scam. He would force me to pick up married men and businessmen whom he had already identified somehow as marks that could be blackmailed with sex. I’d come on to them at a bar, lie to them, and get them to take me back to my hotel room and get them to fuck me. Sometimes we would go to their room, Dwayne always told us girls where we needed to go to perform. I was supposed to get as nasty as a whore could, making it as salacious as possible. We would get them to say stupid stuff like ‘my boss is a dumb shit’, or ‘my wife is a stupid frigid cunt’, stuff they would be particularly ashamed of when they saw it on video.”
“What they didn’t know was that there were hidden cameras already set up. Dwayne had this guy who set up all kinds of electronic recording devices, and they were blackmailed.” She paused as if she couldn’t speak the words, but finally continued.
“Dwayne made more money off of his blackmail scheme than his girls getting turned out for whoring. The unsuspecting marks all had a lot to lose if they got turned into their wives or the companies they worked for. And that was when my world was completely upended.”
Lennie saw she was beginning to shake as tears continued rolling down her face. How could this get any worse? She finally took a deep breath and continued.
“This scheme was making Dwayne a lot of money, as I said. Taylor was in on it too, getting four or five guys a week sometimes, even better than me. Amber refused to do it because she said she couldn’t live with herself, blackmailing innocent married men like that who were alone, horny, and just wanted a little company. She got away with not doing it because she had a different arrangement with Dwayne.” Lennie absentmindedly nodded.
“He had someone, I think, in the hotel business, who identified these men. The slimy guy would set up the cameras beforehand and take them away after. All of this sex happened in two different hotels, which is why I think that was a partner from the hotel business. They were two of the most expensive hotels in Seattle, so the men had money. And no, it wasn’t the Four Seasons where we first met.”
She looked up and gave Lennie a weak but honest smile for a few moments as her thick eyelashes fluttered at him, then resumed.
“He would easily make $20,000 or more off each mark, some of them, I think it was as much as $50,000. Somehow, Dwayne could run a credit check on each one and figure out how deep their pockets were. Five to ten men a week, each paying 20 to 50 thousand in hush money. It averaged at least a couple of hundred grand a week, or more. One week, he cleared almost half a million. If they didn’t pay in cash, their wives or employers would see the tape. They all paid up. But one day, shit hit the fan for Dwayne and me.”
She paused and looked in Lennie’s eyes. Pain showed in each of their faces for different reasons. One reason was hearing the story for the first time. The other was because it was so difficult to recall it once again.
“One of the guys I had set up and blackmailed had found me a couple of months later after conning another guy. After I was done with the most recent guy, I had a couple of drinks in the bar downstairs, mainly to try to forget what I had done. He waited for me to leave the hotel bar and snuck up behind me, sticking a pistol in my back while grabbing me. He told me I would bring him Dwayne, or he would kill me. It was way past midnight, and I was all alone on the street. I didn’t have a choice.”
Lennie moved over to the couch and wrapped his arm around her shoulders, supporting her. She was truly shaking now, her voice unsteady. In her mind, she could still feel the cold steel of the pistol pressed against her neck.
“He took me to a cheap hotel room up on Aurora Avenue North and made me call Dwayne.”
Aurora Avenue North was also the track where the low-level street whores worked, and many seedy hotels were located.
“He told me to tell Dwayne a guy was in my room and was hitting me. The guy slapped me on the face while holding the phone near my mouth, so the slaps were loud and very real. I yelled the hotel name and the room number and screamed at him to save me like I was ordered to, and then he hung up.”
“He told me to sit at the small table in the back of the room. He tied me up completely naked with a gag, put a pillow case over my head, and I sat and waited. I couldn’t warn Dwayne if I tried. Anyway, he kept the door ajar, expecting Dwayne to crash in and take charge.” A tear fell down Lennie’s cheek. Her pain was obvious and was affecting him more than he had first suspected it would.
“Dwayne showed up and crashed the door as the kidnapper expected. But the kidnapper stood in the bathroom with the light off, and when Dwayne ran by, he hit him in the head with a gun and knocked him unconscious. He zip-tied him on the floor and then kicked him a dozen times in the head, face, and mid-section with stiff, leather-soled shoes.”
She was somehow regaining energy as the story continued.
“He kept yelling at him, saying things like “this will teach you not to fuck with me, you piece of shit!”, and stuff like that. He called Dwayne a dumb asshole a half dozen times as he continued to kick him in the head and gut. Dwayne’s head and face were bloody. Then he untied me, pulled off the pillow case from my head, and told me to get down on my knees above him. I was stark naked. I still had the gag in my mouth and couldn’t speak. He was pointing that pistol at my face. I was trembling. He pulled out a second gun and told me to take it and point it right behind Dwayne’s ear, touching his skull with it. He then said there was only one bullet in it and I have ten seconds to pull the trigger, or he would kill us both.”
Cindy paused, starting to cry openly, and looked directly into Lennie’s eyes, the fear of that night alive in her recollection. She began her final confession.
“He pointed his gun right in my face, Lennie, and slowly started counting down from ten. Dwayne was awake by now, gagged, but we could hear him screaming, “NO! NO!” The man looked right at me and coldly said, “Listen, you whore, if you hear the number one, I’ll shoot you. You’ll be dead before you hear zero. Asshole is dead regardless, the only choice you have is if you want to live or die.” So when I heard the number “two”, I squeezed the trigger and shot Dwayne. The sound was deafening in that little old motel room, and the blood gushed from behind his ear. It was horrible. Some spattered on my hands, arms, and face. He wouldn’t let me clean up. He immediately took my now-empty gun and told me to get dressed and leave before the cops came.”
She was shaking. “I m-murdered him, Lennie. I s-shot and k-killed another human being.”
Cindy was now sobbing and shaking uncontrollably. Her body went limp, leaning against Lennie’s. For the first time in her life, she confessed her most horrible secret to another person.
Lennie held her and let her cry for a long, long time. After she slowed down and was able to breathe, he cradled her and kissed her on the cheek. She slowly regained her composure.
“When I left, I was able to grab Dwayne’s phone when the guy wasn’t looking, leaving it off for a week. When I turned it back on, it was full of messages, and the calls came in incessantly. I started taking dates to survive. Not only that, but Dwayne’s other girls kept calling the number, too. I knew most of them; they were out of money and looking for work. Nobody knew what had happened to Dwayne. I set up most of Dwayne’s girls with dates and took some of their money for the connection. That made me a pimp.”
Lennie just nodded. This wasn’t the time to disagree with her, only listen.
“I’ve never told anyone else that story, except for Lori and my therapist. And that was years later. In fact, nobody knows I killed Dwayne. My therapist knew I was holding something back, but I couldn’t tell her because I think they are required to report first-degree felonies to the cops. Lori or Taylor still have no idea.” Lennie looked into her reddened eyes as he tightly held her.
“Now you know it all. I’m a whore, a porn actress, a pimp, and a murderer.” She looked drained, her body limp, the look on her face sad, emotionless. Her confession about her dark past was complete.
Lennie just held her and didn’t say anything. A tear fell from the corner of his eye, and then another. Her face was red and puffy. Her mascara ran down her face, making her look like a sad raccoon or a sloppy clown.
“I can’t be alone right now, Lennie. Please don’t say anything. Don’t leave me alone. Please, will you mount me and fuck me for all you’re worth? Please? I need your touch right now. Show me that I have value as a human being. That’s all I know.”
Lennie said nothing, but eased her down on the couch, dropped his pants and boxers, and kissed her passionately. He moved down her body, licking it sensuously, getting an occasional twitch when his tongue or finger hit a special spot. He lowered his face between her thighs and slowly, methodically began a light and steady licking. He performed fantastic cunnilingus on the despondent woman until her breath started to get shallow and her gasps told him she was close to a giant climax. Her legs locked Lennie’s head into her core as she stiffened up and started coming. She came on his face and on his tongue, her creamy center a special dessert for Lennie. He kept his tongue on her clit until the shaking stopped and then pulled his body on top of hers.
He got on top of her, slowly sliding his hard cock into her wet pussy. She was soaked after the emotionally draining confession. He slid it in with a single, slow push. Starting slowly at first, Cindy grabbed him by the neck while her legs wrapped around his back, locked together. She wasn’t going to let go.
They lasted nearly 30 minutes, starting very slowly to maximize friction out of every stroke. The goal wasn’t sex but emotional and physical bonding. As Lennie continued, they embraced in a long, wet kiss while he was humping her faster and faster as time moved on. As their intensity increased, Lennie was frantically pounding Cindy for all he was worth. She had cum three times already, groaning and mumbling, until there was a fourth climax. Lennie couldn’t hold back any longer and blasted a load of white into her depths.
As they held each other in their arms, the talking stopped. Lennie could hear and feel her slow, deep breaths; she could hear his heartbeat with her ear against his chest. After a while, it was too difficult to keep my eyes open. They fell asleep in each other’s arms.
The early-morning sun was shining directly into Lennie’s eyes. He awoke and looked at Cindy’s clock on the bedside stand. It said 5:05. He could smell the fragrance of a woman’s hair a few inches below his nose, her head on his chest, and her arm around his torso. He had actually slept better than any of the past seven nights. His back was a bit stiff, probably because he hadn’t moved all night with Cindy lying partly on him. No matter. A new day had begun, and there was a lot to talk about.
Lennie slowly pried himself away from Cindy and wandered into the bathroom. He peed like a racehorse. Washing his face and hands, he found some mouthwash, swished, spat, and rinsed. When he returned, Cindy was lying there, completely nude, with a sheet up to her waist and her perfectly shaped breasts in plain view. Her eyes were barely open. She looked angelic, except for the mascara that smeared her face and her tussled hair that unveiled her humanity. Catching Lennie in the corner of her eye as he entered, her eyes opened wide and stared at him. She looked scared and unsure of what was next.
Lennie resumed his previous position next to her, leaning against the headboard, and Cindy adjusted her head and arm so her cheek rested on his chest again.
There was silence for a long while, and then Cindy meekly said, “So, Lennie, would you tell me what you are thinking right now?” There was no urgency waiting for his response. She knew Lennie would speak when he was ready, and it would come from his heart.
“So many different things, Cindy.” Then, nothing else was said for at least ten minutes, when he spoke again. They continued to hold each other tightly.
“Cindy, let me first tell you that your secret is safe with me. I want to assure you of that. And it wasn’t murder, it was killing. There is a big difference. Murder is premeditated and an offensive act. Killing can be a defensive act to protect yourself and others. That’s what happened to you. That bastard who pimped you out took advantage of you in so many ways. Honestly, I’m glad he is dead. I’m just sorry you had to do it and have that scar in your memory. Other than me, how many people know?”
“Like I told you, nobody knows about the killing or the truth about how I was able to get Dwayne’s phone. Only Lori knows my backstory about everything else. Oh, and my therapist. Nobody knows what actually happened to Dwayne. The story I told everyone was that he just went crazy and left town one day. You are the only person I’ve ever admitted to killing another person, Lennie.”
“Yeah, okay, I have a lot of other questions, but I don’t want to press you. Are you up for talking, or maybe we should make some coffee first? What do you say?”
“Coffee would be nice, Lennie.” Before she got up, she hugged Lennie and pressed her lips into his, generating a warm embrace. Lennie smiled when he realized he even enjoyed the taste of her morning breath. She walked into the bathroom and took care of her basic duties for the first time that morning. Her bladder relieved and teeth brushed, she looked in the mirror and decided to wash her face of last night’s makeup. She pulled her hair back into a long ponytail after brushing it for a while. She walked naked into the living room and lay down on the sectional. Lennie joined her with a French Press of hot coffee, two mugs, and a tiny pitcher of cream.
For a good half-hour, not a word was spoken as they sipped on their brews. They sat on the living room sectional, arms around each other, completely naked with a throw blanket on them, enjoying the view of the Lake.
A single water skier went by, being towed by a fast powerboat on the still, glass-like lake below the large picture windows overlooking the Lake. He was an expert level, using a single ski and carving his turns, lying almost flat, his shoulder just inches above the water. He went side to side, making the difficult moves look easy. In another hour or two, the water conditions would make that kind of skiing impossible. Cindy let out a deep, long sigh.
“I know that killing Dwayne wasn’t my fault,” Cindy blurted out of nowhere. “I had no choice.”
“How often do you think about that moment?”
“Honestly? Almost every day. I’m numb to it by now, but I can’t get it out of my head. His head exploded, and all the blood splattered all over me. I’d never seen somebody die like that. It was by my hand, right? I’ve never actually seen a person die before, and I killed him. I saw my mom slowly waste away, my dad get sick, and that poor girl who killed herself in the bathtub, but not an actual death like Dwayne. All that blood everywhere, and his body shaking and then still. What I can’t get out of my head is how his body kept twitching as he died. After a few years, when I had some money again, I was in therapy for almost three years. I did it myself, without anyone else recommending it to me. I am so glad that I did.”
“Was there anyone you had a relationship with in your life? Or just abused by your uncle and those johns of Dwayne’s?”
“No, I’ve never had any kind of relationship other than my boyfriend after prom in my Junior year, except for a guy I thought I had a chance with in a relationship about a decade ago. That failed spectacularly.”
“So, except for your boyfriend in high school and me the last month or so, you have never had sex with anyone who wasn’t paying you or raping you?”
“Other than Lori or my girls, that’s exactly correct, Lennie. The closest thing happened about ten years ago after I tried to start dating a few times, but there was no real romance or connection. There was this one guy, and we clicked at first. I thought he could be the one, you know? The feelings I had for him were like no other man, ever.”
The look on her face soured.
“Our dating went on for a couple of months, but he didn’t know what I did to make money. I thought we were getting close. I took things slow, so we only slept together twice in the last two weeks of the relationship. I thought I had to come clean with at least the sex part of my past. It was terrible.” She was talking in a steady voice, much more confident than last night.
“We were lying on my bed. After I had told him that I was an escort, but nothing more, he immediately started ripping my clothes off. The next thing I knew was that he was banging me like a hundred-dollar street whore. Then, after he came in me, he got up and got dressed without saying a single word. I was still naked, and he leaned over and spit in my face, called me a dirty whore, and left. He never answered any of my calls, and I never saw him again.”
A single tear fell from the eye closest to Lennie. He saw it fall. He shuddered. No wonder she never dated again. There was another pause for reflection.
“What happened to your dad? How did the surgery go for him?”
“It went well, actually. He lived for another 14, no, 15 years. He died about 5 years ago. It was a heart attack and not cancer again, so at least it was quick.”
Silence. Lennie hugged her again in a long embrace.
“Tell me about your sister.”
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