Changing Times
Copyright© 2026 by dawg997
Chapter 14
Erotica Sex Story: Chapter 14 - Lennie and Samantha continue their unique relationship, along with the other girls in the story. But nothing stays the same, and things are changing. Does Samantha remain loyal? Can Lennie, worth only a fraction of those other men, handle his emotions about his girlfriend's many billionaire suitors, many of them in love with her?
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Mult Consensual Romantic BiSexual Heterosexual Fiction High Fantasy Gang Bang Group Sex Orgy Polygamy/Polyamory Swinging Black Male White Female Anal Sex Cream Pie Double Penetration Enema Exhibitionism Facial Oral Sex Voyeurism Prostitution
The Home Front - Helping DJ and More Housewives
“So, Lennie, are you rested and ready for your threesome with Melody and Candy?” It was about 1:30 p.m. DJ was sitting beside him in the overstuffed chair, having snuck up on him and surprised him with her presence.
“Oh shit, DJ, I didn’t even see you!” the startled man said, his body jumping. Lennie had been looking at his laptop and reading posts on X.
“So what are you doing, reading that website X again?” she mocked.
“With Cindy gone again out of town, I have to do something to keep busy,” he stated, a bit of anguish in his voice. DJ, an expert at reading people, even at the young age of 27, realized he missed her and tried to change the mood.
“Lennie, reading that all the time is going to rot your brain,” DJ teased.
“Not with what I read, DJ. Why, just in the last three days, I was reading one of the accounts called ‘unusual_whales,’ with the underscore in between the words.”
“Is that an account about marine mammals or something?” DJ asked, curious.
“No, it’s a site that follows unusual activity on the stock market. Three days ago, I read that someone had bought $10,000 worth of options on a particular stock, and, just two days later, the stock dropped by nearly 40% after some bad news came out that Congress had defeated a proposal to open up mining in an area where they had owned a lot of land in and had expected Congress would approve it. Congressional approval would have meant the mine would have generated over a billion dollars in mineral sales for them.”
“Okay, so far, that makes sense,” the perky blonde said.
“The stock had been rising steadily for weeks, and then suddenly, ‘poof!’ the bottom fell out of the price, and it was back to a one-year low, just like that. This investor bet big on the stock crashing, despite most news reports proclaiming the vote wouldn’t happen for months. But whoever it was who bought the options made about $630,000 on their $10,000 option in just two days.”
“So the person who bought puts on the stock just before the vote and then made bank? Shit, Lennie, that sounds illegal. Somebody knew something about how that vote was going to happen before it happened. They got out in front of the vote and bought options? That sounds like insider trading. What a crock,” DJ complained.
Lennie was impressed that DJ knew what the futures market was and the difference between a put and a call.
Lennie nodded, surprised at DJ’s knowledge of the subject.
“You know about options? And when you ought to buy puts and when to buy calls? How do you know that, DJ? I wasn’t aware that you had been a stockbroker or investment advisor,” Lennie joked.
“Lennie, do you think I just sit on my ass all day in the office between client and provider calls? No, I would go nuts. About three years ago, I started day trading. Been doing it ever since,” she said with pride.
“Day trading? Isn’t that risky?”
“Well, duh, of course. However, back then, I found a company that offered real-time stock investment advice. The owners created their own custom algorithm that searches the stock market and identifies specific stocks they recommend purchasing. It’s continuously updated in real time to reflect changes in market conditions whenever they discover new information that may improve the accuracy of their suggestions.”
Lennie had never heard of such a service, but new opportunities utilizing new technology were constantly emerging.
“They charge $50 a month to be a member, and after you sign a release saying they aren’t responsible for your trading, that gets them off the hook legally. If a customer loses their butt by not following their trading rules, they turn you loose, and they offer up anywhere from four or five stocks to as many as a dozen stocks at any one time. It is simple. The algorithm shows the stock price in real-time as either a red down arrow or a green up arrow. As long as it is green, I buy it and hold it. The minute it turns red, I immediately sell.
“Wow! That sounds too easy. What’s the catch?”
“There is no catch, Lennie, but if I turn away from the computer screen and a stock turns red and I don’t get out within a short time, I start losing money. The real-time price doesn’t equate to the color of the arrow in a minute-by-minute sense, but if I don’t get out within the hour, I usually lose some of the profits that on paper I had gained. If I really mess up and ignore it until the next morning when the market opens, I can lose all my profits and even some of my capital. The key is to be watching the screen in real time if I have money in any of those stocks. If I am not going to be in front of the screen, then I cash out everything, even if it is still green, and go back in the next day or when I have the time again to watch the arrows.”
“That’s interesting, DJ.”
“They have something like a 93% success rate. Now understand that many stocks only increase a point or two in a day or a week or two, and then it’s time to sell. Even after covering the trading fees, I still make money. It may be only 2% or 4%, but that is in a few days or weeks, not annually. As long as I don’t get greedy and don’t hold onto a green stock when it turns red because I’m trying to outthink the algorithm, the small profits add up. It really works. I have been following this program for almost three years now. I track the individual stocks they recommend and learn about their specific market conditions in my spare time. I have learned a lot about being a successful investor.”
“That’s great, DJ!” Lennie exclaimed. He was truly impressed by the 27-year-old blonde cutie, who was also the backbone of Samantha’s Escort Service operations. “So, how much have you made since you started this?” Lennie knew that traditional investment advisors, who manage portfolios for clients with large investments like his in a buy-and-hold situation, are considered successful in most markets if the annual return is in the low double digits. Occasionally, some of the best ones generate returns of 20 percent or more annually. With just under two months to go, Lennie was pleased with his advisors when they showed him his 23% return a month ago.
“I started with ten thousand, the amount I was willing to risk. After about three months, when I saw that it was working, I increased my capital to a total of fifty thousand. Including all transaction fees, I made a 52% profit before taxes in the first year. The following year, I made nearly 75%. This year, with two months left, I am at about 83% and am hoping for 100%.”
“Damn, DJ, that’s amazing!” Lennie said.
“Yeah, because the holding time is so short, the IRS considers it regular income. Combined with the $250,000 Sam—or, I guess, it is you now—I earn for running the escort service, the IRS charged me about $70,000 in taxes that year because it is taxed as short-term capital gains. The taxes were more than the stock profits, but it was worse last year and will probably be worse this year.” DJ seemed a bit dejected at her comment.
“DJ, my original CPA told me long ago something I will never forget. Mind you, I was making much less than your salary now. He told me to think about it as a victory and a privilege to pay taxes. It means that you are successful in what you do. It also means the country has the financial resources to run peacefully. I think about that every April 15, tax day, and you know, I wouldn’t have it any other way.”
“Wow! I guess that once you get into six figures, the government wants a big bite of that money,” DJ responded.
“Yeah,” Lennie said, “I don’t even want to mention how I got hit last year with my nine million in stock distributions. It was brutal.”
“Hey, Lennie, I’m not only a big girl with stock trading and tax ramifications, but I know about your most deviant sexual fantasies and your best sex moves with women,” she grinned. “So tell me, how much did the IRS tax you last year?”
Lennie looked up and to the right, his body language showing DJ that he was telling the truth. “Umm, it was about three and two-thirds million.”
DJ blanched. “Oh my god, Lennie! Shit! Are you for real?”
“Oh yeah, it’s for real. Welcome to America, sweetie. I paid about 40 percent of everything I had made last year in federal taxes. I am so glad that Washington State doesn’t have an income tax. All the other states do, except for five. I would never live in California, Hawaii, or one of the high state income tax states. I only visit them for a few weeks a year, or they would try to call me a resident. My CPA told me I would have to pay an additional $1.16 million in Cali or almost another million in Hawaii. Other states like New York and New Jersey are almost as bad.”
“Geezus fuck, Lennie! That’s a fucking rip-off!” DJ gasped. Lennie was taken aback at her ardent comment because DJ never swore.
“Call it what you want, DJ, it’s the law. So I can choose to pay it and live in peace, or try to dodge it, and before too long, I would have IRS agents knocking at my door and soon seizing my bank accounts and property and charging me with tax evasion. I’d be looking at a multi-year prison term. Again, like I said, welcome to America, DJ.”
DJ paused, her head spinning with thoughts in overtime. “Okay, now I see why Cindy says to be careful and keep the cash tips hidden if the girls don’t declare them on their taxes. I don’t know if you’re aware, but she has a fake ID to rent a bank safety deposit box where she hides the extra cash she doesn’t claim. She told me that if it ever hits a bank account, it is guaranteed to be known. Additionally, if you spend it on anything, especially in large transactions, they can also find you. Damn, I never knew it was so intricate.”
Lennie was surprised at what DJ knew about Cindy storing some of her cash secretly. It was only part of her tip money. Everything else that was paid via credit card was reported, as well as about a quarter of the cash. This was her rule of thumb, shared with her by an expert tax attorney years ago, who was also a former client—in complete confidence, of course.
Lennie already knew about Cindy’s safety deposit boxes in two different banks because she had obtained a fake ID and a disguise for Lennie to use when they went to the banks together, and had added him as an authorized user, allowing him to access the money at will. Cindy did that to show Lennie her complete dedication to him, but Lennie had never taken out a dime or ever planned to do so.
“So, DJ, I see you have your headset on: thus, I assume that you are wired into everything.”
“Yep, if a red arrow appears on any of my day stocks, I get a beep, and if a client calls, I pick up immediately,” she said with pride.
“Everyone in the escort service, Cindy and I, as well as all the girls, and the clients for that matter, are so lucky to have such a smart and dependable woman such as yourself, Dorothy Jean. I mean that,” Lennie said.
DJ smiled proudly.
“So, stocks and taxes aside, why did you come upstairs to visit? Believe me, I’m not complaining, not at all. I love seeing your beautiful face and gorgeous body and soaking in your positive attitude. Except today, I sense something else. You’re not depressed, I don’t think, so tell me, what gives?”
She paused for a few seconds, looking into his eyes and then down to the floor.
“Well, it’s just, umm, it’s just that I’ve been really horny the last couple of days, and, umm, since Fiona is always with Dan or with a client when he is out of town, I don’t have anyone to help me take the edge off of, you know?” She stopped talking.
“Horny, you mean. I thought that we figured out months ago that if you wanted to take the edge off, nearly any of the clients would love a spin in the hay with you.” Lennie asked. He remembered that it was he who figured out that Sharon kept the cock length of every tested client and that DJ, due to her shallow cervix that caused her great pain when penetrated by a cock over six inches, could just accept a date from one of the short-dicked clients and relieve herself.
“Lennie, there hasn’t been a single little-dicked guy in the last three weeks who has called for an appointment. Well, that isn’t completely true, though. There have been a few of them, but all of them are old, and the girls say in their session notes that they are lousy lays.”
She realized what she said about the older clients, and her eyes bulged.
“Oh, Lennie! I didn’t mean anything against you about being old! I know you’re a stud! The girls brag about your oral skills as being the best they’ve ever had!”
“No offense taken, DJ,” Lennie chuckled. “So, continue with your thoughts.”
“Well, Lennie, it’s just that sometimes, taking all the calls from clients and getting them excited about the girl they have chosen, the talk gets hot and heavy, and I get horny. The last few days have been really tough. You are aware that I have to persuade a client to switch to another girl when his first, second, or even third choice is booked. Sometimes they are happy with whoever I offer up, but sometimes I have to talk dirty and nasty to get them in the mood to say yes.”
Now Lennie was intrigued.
“A few months back, when you first arrived on the scene and your girls would take off all that time to party with you, it made for a difficult time for me. Honestly, I was rubbing one out two or three times a day,” she admitted. Her look was one of sexual frustration.
Lennie paused for a moment, taking in what his younger female friend had told him in confidence. It made sense, but he wanted to know more.
“Like what kind of talk is making you so horny, DJ? I guess I kind of understand it, but I would have never known it bothered you so much.”
“Oh yeah, Lennie, sometimes I get to talking dirty, smutty, and even nasty. Pretend you were me and talk about how sexy, say, Fiona or Summer would be the perfect escort for him because they were the only two girls available at the time he requested. Of course, he would never know they were the only two girls available; that would degrade the merchandise. I would talk about Fiona’s angelic face, her red-hot redhead silky hair, those deep emerald-green eyes, and her perfect body, and then I would talk about how sweet her pussy tastes. Or if I was trying to get the client to take Summer, I would talk about that long blonde hair, those giant boobs of hers, and how innocent and giggly she gets, almost like screwing a virgin.”
Lennie laughed out loud. “Damn, DJ, you nailed each girl’s unique assets perfectly. If I had to make a sales presentation like when I still worked, it would be almost exactly like that.”
“Yeah, Lennie, and those are just the descriptions.” She lowered her voice, making it sultry and almost mysterious. “I talk like this, Lennie,” she purred, pausing for effect, even breathing out twice before she began talking again.
“You know, mister client Lennie, that in your dreams, those giant breasts of Summer’s, you want to fondle them and lick them, and you will go crazy when you bite them and twist her nipples. Summer loves it when a man plays with her tits like that. And while you do that, Mr. Lennie, client, you get to stare into that innocent face of hers. If you do it right, she even makes a squeaking sound. That squeak is hotter than hell, and I’ll bet that you have the prowess to get her off. Sometimes, she even squirts when she squeaks. She needs that, you know. Summer is available for you, and I’ll bet you can get her to squeak. Should I sign you up to enjoy Summer’s charms?”
Lennie, only a few days after being drained of his essence by Taylor from his gangbang event, started getting hard, and his breath began to get shallow.
“Goddammit, that’s hot, DJ,” Lennie panted. “Holy fuck! Do you do that often?” Lennie’s mind turned to the time he had fucked Summer at Cindy’s condo, one of his housewives he was required to sleep with as part of Cindy’s request to know them all equally as their pimp.
“At least half of the appointments, I do something like that. A few months ago, when you were playing with your girls and they took off all that time, I had to do this almost every call to get them to take one of the housewives. With the girls going back to work full-time, it isn’t as bad. However, as I mentioned, I still have to do it maybe half the time because all of the girls and housewives are in such high demand. Cindy even mentioned that she was thinking of raising the rate from $2,000 an hour to $2,500. I told her that instead, she should hire more housewives, which is why we are hiring ten new girls for the Consumer Electronics Show in January.”
“Damn, I never understood how important you are to all of this,” he proclaimed. “You were going to ask me something, DJ. What is it?” Lennie queried.
DJ paused for a few seconds and looked into his eyes. “Well,” she slowly said, “Fiona is always gone now. You know, we were pretty close and had a lot of great times together physically. We were like two lost souls that balanced each other. We both knew it wouldn’t last forever, but now, after she is always gone, either working or with Dan, I had no idea that I would miss her touch so much.” She looked into Lennie’s eyes, a sad look on her face. “I never thought that I would feel so alone.”
Lennie was surprised and touched at the young woman’s confession. “So, I was wondering if you might help me out,” her voice stumbling at the words. She had never been like this before, so uncertain, so timid.
“Help you out, how?” Lennie queried, concerned that the girl, with her usually bright and positive attitude, was now so sad and gloomy.
“By servicing my needs,” she slowly said. “I need the touch of someone that I trust, someone I feel comfortable with. I mean, I know your cock is in timeout to rest and recuperate, but I had thought that maybe, well, perhaps, you could use some of your fine skills and go down on me to take my edge off.”
This was new to Lennie. He had never been propositioned as a sex worker before, even though this was entirely an in-house request without any financial compensation. He slowly smiled.
Lennie held out his arm as if to hold her and protect her. “Come here, sweetie. I’m so sorry to hear of the dilemma that you’ve found yourself in. I’d be happy to help. Why, just thinking of the fact you came to me to help you out, I’m honored.”
He pulled her close and immediately started showing her the passion she needed. Pulling her Bluetooth headset off of her and dropping it to the carpet below, his arms surrounded her as he kissed her, softly at first and then with more passion. Deep kisses combined with his hands softly rubbing up and down her back as they became closer, and the temperature increased. He continued to fondle her body as his hands found her palm-sized breasts, which he caressed and rubbed. DJ’s breath started becoming shallow, and Lennie could tell she was responding like he wanted her to. He moved her just a bit and silently signaled her to pull off her top, as her bra was now in his reach. His hands went behind her and deftly unhooked the three fasteners, letting it fall to the floor.
As their kisses became deeper and more passionate, his hand slowly slid down her side and to her hip, never letting it free of her skin. As their kisses got even hotter, his hand slipped between her thighs, continuing his steady pressure on her body. Getting closer to her prize, he sneaked his hand between her thighs and found her spot, rubbing it over her tights and panties that covered her flower.
“Ohh!” she gasped. “Oh yes, Lennie, oh god, yes!” she moaned. She
“You need this, baby. Let Lennie help you. You need this so bad,” he whispered in her ear between kisses, his hand continuing to explore her most private of parts.
Ohh, Lennie!” she moaned. “You found it! Right there!! Ohh, ohh!” she moaned, Lennie now taking full control of her pleasure and delivering beyond her imagination.
“You need this, girl. This is all just for you. Take it, girl, yeah, take it,” Lennie whispered as he continued to wildly rub her G-spot while licking her ear and the side of her neck. His upper body pressed against the side of hers. His manly scent and strength overwhelmed her senses. The sensation was overwhelming as his hand pushed faster and harder on her center. She was moaning uncontrollably now.
“Ohh, ohh, ohh!” she groaned, not being able to keep her groin still. She couldn’t help undulating back and forth, but Lennie’s strong hand restricted her movements. She started gasping for air, and finally, she started squirting and shaking uncontrollably. Squirting everywhere, on Lennie’s hand, on the leather sectional, and on the carpet below it. Her feminine liquid squirt flew everywhere, and DJ was completely out of control and groaning loudly. She tried to stop her groans, keeping them inside her, but then she burst, losing the battle inside her. She screamed at the top of her lungs.
“AAGGGGHHHHHH!” OHH MY GODDD!”
The entire area under her was soaked. Lennie pulled his curled hand from her snatch and quickly dropped back down between her legs. He forced two fingers straight into her pussy while tongue action licked and rubbed her clit and lips. The pressure and speed were unbearable to her.
DJ started gasping for air, making the sound of a wounded animal as Lennie kept up the sexual pressure. It went on for minutes, each second of that delicious and uncontrolled torture of the sexy blonde.
Finally, she got enough air in her lungs again, but only enough to weakly utter, “Lennie! Oh god, oh god! Lennie!” She collapsed back to her flat position, drained of any energy. Her body had surrendered to her lover and mentor, who knew how to eliminate the sexual frustration her job caused.
DJ lay there, weakly gasping to get air back in her lungs, while Lennie lay naked beside her in the wet spot that flooded the sectional. He pulled her to him, and she collapsed into his manly touch. Her body molded into his, releasing all tension. Despite feeling extremely content, she started quietly weeping after a few seconds.
It was the opposite of her angry outburst a while back when she admonished Lennie for not taking her job seriously. It was as if a dam had broken, and her emotions recklessly flowed out.
“Shhh, shhh, everything’s going to be okay,” the older man whispered in her ear as he slowly stroked her temple and ran his fingers leisurely through her hair. “It’s all going to be fine, just fine,” he purred, his voice calming her into a completely relaxed and content state. Sounds of her shuddering and lightly gasping for air continued until she broke down, continuing to weep, her defenses shattered. Lennie, realizing that she had become a bundle of mixed emotions, let her cry and shake as he held her for as long as she needed until she stopped and her breathing started becoming normal again.
“That was the most incredible experience I’ve ever had,” DJ whispered as if it were a meek confession.
“You needed that, sweetie,” Lennie whispered back, not wanting to break her afterglow spell.
“Thank you, thank you, thank you,” she repeated as she continued to experience the comfort of being in his arms and against his big body. She moved around to give him a long, passionate kiss. The Bluetooth started a faint beeping sound from the carpet below.
“I guess I’d better get that, Lennie.”
“Not yet, sweetie, just lie here for now and let your body and mind recuperate. Enjoy the glow,” he softly ordered. She snuggled closer to him, silently following his command.
Twenty minutes later, she finally moved and pulled away from her satisfying pose with the older man. She reached down, put the Bluetooth headset back on, and, touching a button, started hearing the message the caller had left.
“Thank you, Lennie, for being there for me. You are truly a special man.”
The next day, in what appeared to be a repeat of the previous day, Lennie was reading on his laptop as he sat in his living room during the early afternoon. DJ was not around. She was either in her office or running errands. The phone rang, and Lennie picked it up, and seeing the picture on his cell, answered with a “Hello, Mike! How is it going?”
Mike answered in a perceptibly downbeat voice. “Okay, I guess, Lennie, but I had to talk with somebody, and really, there is nobody on the planet who can understand how I feel other than you. How do I explain to the girl of my dreams that for the past two months, she has been a world-class whore who only provides her charms to some of the world’s richest men? I’m crazy for her, and right now she is in Hawaii with a billionaire at an estate on the north shore of Kauai.”
Lennie quietly listened to his friend.
“We talked for twenty minutes like college lovers until she told me she had to go because she had plans. Of course, those plans were to have an intimate and passionate paid encounter with that guy, something I will never know the details of. And I must accept it if I want to be with the most amazing woman I’ve ever met. Anyone else would think that I’m nuts.”
Lennie was caught a bit off guard but immediately understood Mike’s dilemma. He had often felt the same way, although more sporadically in the last few months after he had time to accept the lifestyles of his girlfriend and the others who lived with him. What was also different was that Lennie had regular access to all of them for his pleasure, even though it had been a lot less in recent months.
“Lennie, I thought that I knew what I would be getting into after that meeting we all had at the Mexican restaurant. I accepted the fact that Taylor would still have sex with other men who paid her vast sums of money and took her to high-end hotels and vacation spots. I mean, my god, she said she made over a million and a half last year! After all, expecting her to simply drop her professional relationships with the four or five dozen men whom she calls her ‘suitors’ ... honestly, I accepted that she wouldn’t. But this ... this is something else.”
Lennie paused and finished Mike’s sentence. “It’s the loneliness of her not being around, right?”
“Yeah, that’s exactly it, Lennie. How did you know?”
“Because I also experience that same loneliness when Cindy is working, too. When she is out of town, she texts me a dozen times a day, usually short messages about the things she is experiencing at that moment, such as the sunny weather, the local geography, or some event she experienced that I would find interesting. She doesn’t mention what she is doing with her client, so she is sensitive to me in that way. She, too, has on occasion referred to the clients as her suitors. But yeah, I miss her.”
“God, Lennie, you nailed it! I feel the same way. Taylor calls me at least three or four times a day so I can hear her voice and that goofy snort when she starts laughing too hard. I can always make her laugh, you know. It’s easy. It’s one of many things I like about her. You’re right about her not mentioning any other man. She only talks about us and how she can’t wait to come home so we can be together. Lennie, how do you do it, the realization that there are two worlds, one with your girlfriend and one with yourself, and you are only in one of them?”
Lennie felt bad for his friend, and while he often felt the same about Cindy, he had a different perspective. “Mike, I understand and feel the same way that you do. I only know that when I accepted Cindy, I accepted her life, her history, and her unusual career. I fight the negative feelings even to this day, and I don’t think they will ever go away. Then again, remember I am their pimp, and so I have to think on dual tracks about them all the time. You only think on a single track, and it must be more difficult for you than for me. I’m sorry if I led you down a primrose path. I only thought that you and she would be good for each other and make each other happy. I never thought it through, I guess, and for that, I’m sorry, bud.”
“No, no, Lennie, no apology needed. I’ve been thinking about this for the last month or so since she started traveling a lot, and I wouldn’t change it for anything. I love that gorgeous Aussie. She is as hot as hell, but her funny, goofy, and sexy attitudes, all mixed together, make her personality so special. I believe I love her so much now that I don’t want to share her with anyone else. And that is what her profession actually entails: sharing herself with many different men, both emotionally and physically. I suppose there is no easy way out, well ... except to break up with her. That is the last thing I want to do. Does this make me a cuckold, Lennie?”
“Cuckold? I think that labels are a waste of time and limiting, Mike. A woman puts a cuckold down, embarrassing him in front of another man while having sex with him. Taylor is the opposite of that. You haven’t changed, and she hasn’t changed. You know how she feels about you, and that hasn’t changed, has it?”
“Oh no, Lennie, not at all. She tells me that she loves me before she hangs up, every single time. I have never had a woman in my life be so interested in what I think or do.”