Changing Times
Copyright© 2026 by dawg997
Chapter 19: The New Reality
Erotica Sex Story: Chapter 19: The New Reality - 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 NonConsensual 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 next morning, Lennie awoke later than usual, about 8 a.m., and felt a warm, soft body wrapped around him. Tenderly clinging to him, her arms were around his torso, one hand on his shoulder and the other down between his legs, gently fondling his soft cock as her warm breath rhythmically exhaled on his neck. A few long wisps of brunette hair were lying on the side of his face. As his consciousness became aware, he nuzzled back into her, his Cindy. It was such an amazing, warm feeling. He couldn’t help but smile happily, contentedly.
Slowly waking up, his mind started working, and he realized they didn’t go to bed together because Samantha had three dates the night before: two two-hour encounters with regulars and a six-hour engagement with that older, sweet guy, Harry Bridgewater. The next thought was how much Samantha had been seeing old Harry recently. It seemed he was in Seattle for the last month or so, and she was with him most late evenings, with a full overnighter a couple of times a week. And every encounter was at the Four Seasons, he thought again. Damn, he must have one helluva hotel bill. I’ll bet Greg was getting some good tips when Harry visited the bar.
Couldn’t blame him, being with the sexiest and most beautiful woman who would do anything physically or mentally for him, Lennie thought. If I were old, alone, and worth over a billion dollars, I probably would be, too.
Unlike Lennie, who was 67 and had followed a disciplined workout routine under the guidance of a professional trainer for the last two years, Harry was a small man who had not engaged in any physical workouts for decades and had never really paid attention to his fitness. Harry, on the other hand, was frail and a shadow of what he was decades ago. His health was nowhere near Lennie’s, Cindy had told him more than once, and he looked like all of his 70-something years.
During the dates with Harry, instead of getting pounded for hours, Cindy told her pimp and the notes in the SES app that Samantha would make slow, passionate love to him for hours, slowly kissing and fondling in the hopes that he would come at least once. Instead, his desires were met by Sam acting as his late wife, Ruthie, with her magnificent breasts and her ability to let Harry nuzzle into them while softly whispering sweet nothings and fantasizing about her being his late wife. Harry and Samantha would spend hours doing this.
Lennie was now awake and moved just enough to be able to watch Cindy softly sleeping. Her quiet inhaling and exhaling seemed louder than they were, and Lennie was finding solace in simply observing her.
She’s so fucking perfect, he thought. She shares herself with other men for gobs of money, but she always comes back to my bed. I guess that is the important thing, his fuzzy mind thought. She honestly enjoys being a whore to her stable of men, and they truly seem to love her, at least most of them, his thoughts wandered. I am sharing her body, but her heart and loyalty are reserved only for me. That’s the important thing. He felt a surge of happiness inside him as he thought it. Cindy was his: her mind and her heart.
His eyes now open, he stared at the sleeping beauty and smiled to himself. She is so consistently trustworthy to me. She cares for me and what I want and thinks as no other woman has in my life, ever. And if that wasn’t enough, she has delivered another half-dozen of her sisters to me, who think I’m their hero and will do anything for me.
He racked his mind thinking about anything similar and could think of only two couples who had been together for decades and loved each other so completely. Soulmates, he thought. Yeah, those two couples are soulmates. I guess that my soulmate is an experienced, successful prostitute who loves me unconditionally. He snickered to himself and thought, In what world would a prostitute be my soulmate? Whether or not I wanted it to be, I finally found my soulmate after all these years, and she is a prostitute. He grinned a bit at himself. Okay, then. Guess that’s the way it is.
He looked down to see the peaceful look on her face, and the warmth inside him grew immensely. Her naked breasts were uncovered, the sheet around her waist, showing off her perfectly formed nudity. He couldn’t hold off. He had to touch her. His hand softly slid from her shoulder, down the side of her body, and rested on her curvy thigh. Still sleeping but responding, she flipped and pushed her butt into Lennie. Her curvy butt cheeks wiggled back into his groin, and finding his limp dick, she nudged it between them as if to lovingly capture her prize.
“Good morning, baby,” Cindy purred, still mostly asleep. “I got in late last night, and you were fast asleep, so I didn’t wake you. Ummm, spooning with you feels so good; let’s lie here for a while. I love you so much, baby,” she whispered. Even in her whispering voice, she was so damned sexy. She was perfect, absolutely perfect.
Lennie couldn’t keep his hands to himself and slowly, sensuously touched and softly fondled her perfect skin and feminine curves as if he were reading braille. His hands were reading her every letter, every word. He was reading a masterpiece and couldn’t stop.
“Umm, that’s nice, baby. I love the way your hand is exploring my body. You have such a nice touch, and your hand has the confidence of knowing it owns this body. My body is for you, baby, and it feels so good when you explore it,” she whispered.
Lennie kept fondling her curves, and even if he couldn’t see which ones they were, memory reminded him of how great each curve looked. Cindy, still sleepy but now sensing Lennie’s libido rising, gladly made herself ready for her man to take her any way he wanted.
Cindy, now awake enough to respond, turned over and faced Lennie. He moved to kiss her, but she turned her cheek to him. “Babe, my morning breath. But I douched after my last date, so my pussy is clean for you,” Cindy softly spoke. He shook his head and softly turned her face back to his. She received Lennie’s first deep, soft kiss of the morning. She reveled in the feeling, warming to the fact that her man was with her and letting her lie there with a sense of peace. Eyes closed, she soaked up the love and passion her man was extending to her.
This is perfect, she thought. I am so lucky that I found Lennie. He accepts me for what I am. Lennie lets me be me.
After the last of the long kisses ended, she wrapped her arms around his back to hold him tightly. Lennie was now awake and peacefully staring at the brunette beauty, her hair mussed and her makeup gone, removed the night before when she went to bed. Even without the makeup, she was flawless. Lennie kissed her again with a bit more passion and then moved slowly down, his lips grazing her neck as his tongue tasted the nape of her neck.
“Ummm, ohh, yeah, Lennie, ohh fuck, that’s so nice,” Cindy softly whispered. “Yeah, baby, just like that. Enjoy this body; it’s yours. Oh yeah, you are so good, sooo gooooddd,” she softly moaned as his fingers found her moist smile between her legs and gently zeroed in on what gives her pleasure.
He moved down her body, slowly licking and softly fondling all of her curves, until his mouth reached her pubic strip above her pussy. He continued down to her prize, the scent of her pussy leading him to heaven. His tongue, wet from the tasting spree on the way, licked her hole from below and, passing through it, found her little, hiding clit.
“Ohh, Lennie! Ohh, yes! Right there, baby! God, your tongue is so fucking good!”
Lennie now knew she was waking up as well because she had said “fucking” in her compliment, for emphasis. If she were still asleep, she would have said much less and maybe just purred. Good, he thought; she’s awake enough now to come. I want her to gush all over my face. I want that taste, that smell, that wet feeling of her explosion. I want it now.
He continued his masterful pussy-eating skills, slowly and softly, building passion as he continued. She was tangy, a bit more concentrated than when she just stepped out of a bath, but still so desirable. Her passion from the evening before with Harry had generated a wetness that had dried hours before, gaining a certain character like a fine red wine that had been properly aged. Harry never came inside her, and the scent was a result of her passion. Instead of years like wine, her pussy taste had aged for the evening, which gave it a seasoned taste. It was a bit strong but glorious and satisfying, which led Lennie to explore even more.
Her eyes still closed, Cindy’s awareness took over as she turned onto her back and spread her legs.
“Oh, Lennie, oh yeah. Right there, baby. Oh fuck, your tongue. Oh yeah, just like that. Lick me, baby, lick your pussy. Make her wet, baby. Oh fuck yeah. Ohh! Those fingers are, oh, god, oh, yeah! Just like that! Lick me, stroke me. Oh fuck yeah, you are sooo good at that!”
He kept going, now with her approval, and his passion kicked in. He wanted, no, needed to taste her wetness. Now he was on a mission, licking, stroking, lapping, and fingering with curling fingers inside her. The prize was close and getting closer with her short, gasping, stunted breaths. White girl-cum was forming on his fingers and leaking out onto her labia. His lips were lapping up her sweet tang as his face was being soaked. The scent pulled him in with even greater frenzy.
Oh God, Lennie! Oh God! Yes, like that! Just like that! Oh God, I’m gonna come! I’m gonna come! Oh Lennie! Oh God, YESSSS!”
She squirted as she shuddered, locking Lennie’s head between her silky thighs. Holding him tight, she started to gush as her body shook.
“Ohh FUCK YEAH!” she screamed as her body shook uncontrollably. Lennie’s face was soaked as she squirted, making Lennie’s face and some of his hair a mess. She didn’t let go until her tremors subsided, seemingly long ago. After the final couple of grunts finished her off, her thighs slowly released Lennie’s head from between her legs.
“Come here, baby, let me kiss you. I want to taste myself,” Cindy muttered, her body now in a peaceful and satisfied state. Lennie moved up to her, and their lips collided, her arms around his neck. Their tongues slowly and softly danced as she tried to enjoy every drip of her satisfaction, the skills of her man, and the reason it occurred. God, this is perfect, she thought to herself.
“Lennie, can we stay in bed awhile?” Cindy asked. “I feel so content right now, and I want you beside me.”
“Sure, sweetie. Let’s just lie here and enjoy each other’s warmth.”
“Thank you, baby.” Both of them fell asleep again and woke a couple of hours later, her scent still saturating Lennie’s satisfied face.
Lennie woke up first, feeling Cindy’s nude body next to him. Am I having too much sex? It never stops around here, his foggy mind told him.
Lennie stopped for a moment and realized the absurdity of what he was thinking about. He was complaining to himself that there were simply too many incredibly beautiful women that he had to have sex with. All he was doing anymore was screwing these willing beauties one after another, and yet he was complaining. At his revelation, he wondered why he felt that way.
Then it hit him: his body couldn’t keep up with his imagination. He wanted to please them all, but there was no way he could keep up with the demands. He was bedazzled at how willing and creative these women were to ensure he experienced every sexual fantasy Lennie ever had. And having continuous sex with amazing women was wearing him out. For the first time in memory, he was admitting to himself the limits of aging.
It wasn’t like he was ready to be tossed out with the trash, but he realized that he didn’t have the sheer sexual appetite he had three decades ago. Another thought hit him. He loved a juicy ribeye steak, but these days the portions were less than half of some of the crazy-huge cuts he grilled at his own barbecue 30 years ago—no judgment, simply a point of information.
And then he thought of his girlfriend and her six work sisters who lived with him and watched over him like a hawk, catering to his every desire. He truly enjoyed making slow, sweet love, eating their sweet pussies until they cream all over his face, pounding any of them hard into the mattress and hearing them wail, and anything in between. Just not as much as in his younger years.
Something was missing in his thoughts, and then he realized that just being around these women, one or all of them, was so fulfilling that he could simply be with them to talk or just stare at them and their beautiful bodies. While that may be good for him, he knew these women needed sex of all kinds much more than he ever could deliver, and they needed to continue to work their behind-the-scenes profession to fulfill their physical and emotional needs he could not meet.
It wasn’t fair to his stable of gorgeous girls, all with crazy-high libidos. They could quit their profession; after all, the younger girls were working on their second million, while the seasoned workers were worth five million. Or in the case of Taylor and Samantha, well over ten million each. Also, they also invested it well, owning expensive condominiums and stock portfolios, managed by smart investment firms.
No, it wasn’t only about money. It was about how the girls wanted to live their lives. Escorting and girlfriending had, over time, become the centerpiece of their lives. All of them loved sex, especially when they controlled the environment. When Lennie accused them of being nymphomaniacs, they simply giggled and laughed. They were not only happy to turn trick after trick with their rich johns, but also proud of the stature of the men they serviced. Safety and sex for profit. Controlling all variables is how SES was built.
Lennie smiled to himself and realized he wasn’t dead yet. He could still perform with his collection of feminine riches, making them happy while he drowned in their charms. The girls would always deliver beyond his wildest dreams. His women still sexually want more, a lot more than he could ever give, and that is why being professional girlfriends for the upper crust makes so much sense for their relationship, as unusual as it was. If that’s true, what could he do to help the girls attain as much as possible? Samantha created her own marketplace, not just her own company. There was no reason, Lennie thought to himself, to hinder her in any way from realizing what she was building before they met.
What a conflicting set of ideas, he pondered. My financial success is beyond my wildest imagination. I’m living in the home of my dreams with an incredible view of the Sound, driving the car I want, eating at the finest restaurants, and increasing my bank account by many millions each year. And now, for the last seven months, I have loved an active and highly sought-after prostitute. Her friends all live with me, and they are expensive prostitutes as well.
He looked down at the still-sleeping brunette and had a warm feeling as he stared at such magnificent beauty.
Cindy means so much, and she is so special, not just to me, but to many men who are more powerful than I am in controlling huge corporations and have more money than I do. For many of Samantha’s clientele, Lennie’s entire net worth would be viewed by them as a poor week for their investments.
The irony was too gigantic to ignore.
He then remembered what Cindy, or DJ, or one of the girls told him: they may have bank accounts and assets that dwarf Lennie’s, but Lennie is richer. Lennie is the man with seven gorgeous women who do whatever he wants, whenever he wants, not their clients. No, they have to pay thousands of dollars an hour for their presence and access to their charms. Even then, they usually have to wait until one of the girls becomes available. With Lennie, it took nothing more than a wink of the eye or the crook of his index finger to get any one of them naked and pleading with him to perform the dirtiest sex acts he desired.
It hit him: Lennie was the richest man in the world. Not only did he have everything he could want and complete freedom to do anything anywhere, but he had seven beautiful women who lived with him and considered him their lover and confidant. And their leader, the woman who created the entire sexual ecosystem, the one who was the smartest, yet kindest woman he had ever met, was his girlfriend and devoted to him in every way.
No man could claim both, especially not any of the SES clientele. While they had more money than he did, they had to pay for the company of the same women who would fall all over themselves to get Lennie’s attention at home, much less happy to perform any sexual act with him or for him at the snap of his fingers. And what he wanted to do was to honor these women, his girls, for getting him there while respecting them for what they do.
It was Saturday afternoon, and Lennie walked downstairs to the office. Whose ownership it was, that was now questionable, but it was getting full use in any case. He walked to the door, and a smiling DJ looked up from the desk, typing notes on the computer while talking on her Bluetooth headset.
“Let me see, Cal. I’m checking their schedules now, and it’s tough to find a time you requested when both Sam and Trinity are available for at least a month. Are you sure that you can’t substitute one of them for another girl? I can pair you with Kaylani and Samantha on Tuesday evening, or Trinity with either Kaylani or Maria on Wednesday at the same time.” Lennie silently watched her as she waited for him to finish speaking. “Uh-huh, yeah, that’s all I can do until next week, and you told me you are in Florida for business then.” She looked up and saw Lennie at the door. He was moving his hands to signify he wanted to talk with her.
“Just a minute, Cal, I have to talk to someone for a bit. Can you hold?”
She looked up at Lennie, smiling at seeing the gray-haired man for the first time today. “What is it, Lennie?”
“Did you run those reports I asked you to print out?” He was acting not just as a man, but as the girls’ business manager. He was taking his role as their pimp seriously.
“The revenue and the body count skin reports—yep, here they are.” She handed him the two long reports. He perused them while DJ continued talking to a client about arranging a threesome with him and his desired girls, Sam and Trinity.
“Ahh,” Lennie said to nobody in particular. “Look at that!”
DJ looked up at him and said, “What?”
“The girls, and your amazing efforts scheduling them, of course, have exceeded their goals! Look at the skin report.”
The skin report was a count of how many men each woman had pleasured, as well as a brief recap of the acts they performed. The girls used it as a measure of how well the clients thought they were performing. It was much more detailed than the one last summer, when Lennie first learned of the report, the one that had the girls working as much as they could to counteract the negative customer response to being unavailable.
“All the top 50 clients of the last two years have had multiple dates in the last three months, and the top ones have had weeks of skin time with their favorite girls.”
Lennie had started using the same phrases the girls used in their work.
“Skin-to-skin” time, or simply “skin time”, was a phrase that meant the same as face-to-face time, but in their world, it meant they were naked and actively having any sex or other paid encounter the client wanted. Skin-to-skin time meant they were naked and fucking any way the client wished. It was the best way they could quantify whether the client was getting what they wanted, measured in sexual or sensual acts, not just money. In the last three months, it had become the focus of the girls’ professional activities.
“Cal, can I call you back in a few minutes?” DJ spoke into her headset. “I have to talk with my manager about something new that came up. I will call you back in ten, alright?”
“I hadn’t had a chance to review these reports yet, Lennie,” DJ said. She continued. He handed her the reports, and she quickly perused them.
“I didn’t realize the girls had made so much money the last three months, Lennie. And, wow, look at that! The skin time has, of course, gone up dramatically. Look at Jackson Haggarty; he has had over thirteen weeks of skin time, a little over four with Sam, over two weeks with Maria, and ten additional encounters over a few months. He had a 48-hour double overnighter with Michelle, and more than a full week when added up, each with Lori and Fiona, too. And look, he has been using Alexis and Summer more than ever before, as well as trying out the three newest housewives, Kit, London, and Courtney, multiple times,” she stated. Adding up the times, DJ was surprised as she told Lennie, “Shit, that’s over eighty days in the last four months.”
“Yep,” Lennie answered, “and because of Cindy’s successful desire to recommit to the client base, the girls are all caught up now. Everyone has been so busy, they forgot the goal in the first place.”
DJ smiled, pleased at being a part of the shared success. Lennie continued.
“So, what we are going to do is have a mini-vacation for three days, starting Monday morning. You too, DJ. I expect you to leave a message for callers explaining that the service will be unavailable for a few days and will be back on Friday, and that clients should leave any desired requests for girls as a voice message, but you won’t be available until Thursday afternoon to confirm. Got it?” It wasn’t a request but an order: an order from a pimp to one of his girls. Lennie was starting to take charge in the role he had been given and now began to understand exactly what that meant.
“But Lennie, what about the housewives? They already have several dates, and I spend the most time on the phone scheduling them. What will I do about them if I am offline?” DJ was concerned about the reputation of the service. She didn’t want to be unable to respond to a call any time of the day or night.
“DJ, have you thought about who would back up your position if you got sick or were otherwise unavailable?”
She had a confused look on her face. “No, Lennie, I haven’t had a down day in nearly five years.”
“A good organization always has a backup at any critical position, and that describes yours perfectly. If you were to have a housewife as a backup, only for emergencies, who would you recommend?”
DJ thought for a moment and said, “Probably Michelle or Dani.”
“Think about teaching one of them your job. For the training period, pay them their regular rates, too.” He paused for a moment and then added, “You know what, bring them both in for training. Your job is critical, like being the catcher on a baseball team. That position needs more than just one backup for the good of the team. Now, I want you to cancel any appointments after Sunday evening. No overnighters, either. I want all the girls to be done working by about 9 o’clock or so. Can you do that?”
DJ was a bit startled. “Why, Lennie? I mean, sure, I will do anything you ask, but I was not aware of anything else going on. Should I be aware of something on the schedule?” She scanned the large calendar on her screen, which showed every appointment for the upcoming week. “I’m looking now, and there are only three dates so far from Monday through Thursday evening, by the way.”
“Good,” he said, “then free up the girl’s schedules Monday, Tuesday, Wednesday, and Thursday until the late afternoon. Give those dates to the housewives.”
“Why?” DJ asked.
“Because I said so?” Lennie retorted, not wanting to sound demanding or give away the surprise he had planned.
“Okay, Lennie, you’re the boss,” DJ answered. She tapped a button on her headset, and her phone redialed the last number she had talked to. On the second ring, he picked up, and she spoke. “Hi Cal, thanks for waiting.” She paused and nodded at the words over her headset. “You want Trinity, Kaylani, and Maria? All three? Starting at 8 p.m. on Wednesday and going until noon the next day? Done. Cal, the blonde, and both brunettes are yours,” her voice warm and smiling.
As the sun set and Sunday afternoon morphed into Sunday evening, Maria walked in the door. Lennie, Taylor, Lori, and DJ were sitting around, reflecting on the previous few weeks. A lot had happened in that time. Lori had found her new man, who was actually a client that all the girls had entertained in the past seven years. Each girl knew Roger well and approved of the new relationship with their sex-sister when they found out. At one time, months ago, Roger had asked Samantha for marriage, not even knowing her real name, but was politely turned down. Cindy knew that while he was a great person, they were incompatible. An evening of paid pleasure with Lori found the two bonding, and now a true relationship was blossoming.
Roger was in Europe doing what CEOs of large international corporations do: growing the business he ran. That required constant meetings with customers, financiers, employees, and government officials. He had told Lori that he had hoped to be back in the US, with a free schedule, by the middle of the upcoming week, but he had said that a few times already when emergencies arose and he had to cancel his plans. Lori was hopeful but also practical. As the new(er) CEO of a multi-billion-dollar company, his time, generally, wasn’t his own, and she respected that. Still, it made for some lonely nights that Lennie was quick to fill in as her alternate man and still her pimp, as she had gotten back into the game a month ago, nearly full-time, with at least ten dates a week. In fact, that decision made her available for an evening with Roger, and the resulting fireworks had given her a new lease on life and a new man, after her sugar daddy had died a few months earlier.
Taylor was also boyfriend-free, as Mike was participating in an IT installation for his employer’s biggest customer and was in Los Angeles, overseeing a massive system upgrade of the client’s information system.
DJ was waiting for Fiona to come home and knew she would have an evening alone with her redheaded lover without their shared man, Dan, who had left earlier in the day to fly out to Chicago for business.
The door of the home opened, and Cindy walked in to the combined greetings of her friends and her man, Lennie. She had finally returned after a long overnighter last evening and all day with one of her regulars, Harry Bridgewater. Harry thought that Samantha walked on water and didn’t care if his mind confused her with his late wife and confidant, Ruthie.
Even though Fiona and Kaylani were still on dates and not expected home for an hour or three, Lennie decided to make the announcement. He couldn’t keep it in and already wanted the girls home to hear the good news. He stood up from his chair to speak, which got the attention of all the girls.
“Girls,” Lennie began. “All of you, listen up. Starting now, for the next three days and into the afternoon of the fourth, everyone is off from work. All of you are going to take a break, and we’re going to have some fun.”
“But baby, our clients,” Cindy started, but was cut off by Lennie.
“Our clients,” he repeated the beginning of her statement, “have been dealt with appropriately. I had DJ run some reports, and all of you have been stellar businesswomen and magnificent whores, attending to our most important client’s needs.”
At that moment, Fiona walked in the front door, having finished up her third and final date. She wore a body-hugging dress that showed off her rocking body, while her red hair was down, covering her shoulders and most of her perfectly proportioned breasts. She saw that the others were in a meeting.
“What’s up?” she inquired.
“It’s a house meeting,” DJ whispered. Fiona walked over to DJ and gave her a long kiss, her arm reaching into the small of DJ’s back to pull her close before sitting down beside her. Lennie continued.
“The backlog of date requests is back to normal, and the responses in the app from reading client reactions confirm your collective skills have pushed client satisfaction over the top once again. The skin report shows that you are all giving the men what they want. It is proven by the record tips they are giving you. Your average tip amounts have never been higher since the app began collecting information. And I don’t have to tell you all that you’ve been busy. The total number of encounters per week is higher than it’s ever been. Collectively, you girls have earned more money in the last three months than during any similar time period in the last three years. All of you are reaching personal records with your income. You should all be proud of how you have responded: once you realized you were slacking off and needed to do something about it.”
“Really?” Maria asked.
“More money than ever?” Fiona queried.
“All of the clients are happy now?” Lori questioned.