Changing Times
Copyright© 2026 by dawg997
Chapter 7: Successful Business versus Good Business
Erotica Sex Story: Chapter 7: Successful Business versus Good Business - 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
Samantha took a deep breath before knocking on the door of the downtown hotel room. This was her second appointment with a client this evening and her final one until early tomorrow evening. A few hours ago, she made sweet love to a client she had known for nearly a decade. The encounter wasn’t earth-shattering, but it was pleasant, and she left her client happy, with a content smile on his face and a flaccid cock.
The hotel room opened, and a smallish, brown man in his late 40s opened the door, pleasantly saying, “Hello, Samantha. So good to see you again. It’s been ages.” However, he gave a lukewarm smile, not the warm, friendly greeting she regularly received from most of her highest-paying clients. She walked a few steps, and as he closed the door behind her, he turned to her to give a nice but insincere hug. They didn’t even kiss.
“So good to see you, too, Ashok. Yes, it has been quite a while.” She thought for a quick moment and realized she hadn’t been with him since before she met Lennie, and since then, her life changed for the better.
“Was it April the last time we were together? If I remember, the NCAA Final Four championship game was playing in the background.”
“Always the mind with a steel trap,” he chuckled, again with no sincerity. “Yes, that’s right. It was early April. Why have you not been available, dear?”
She knew her client, Ashok Kumar, a naturalized Indian who, after attending Harvard in Boston, relocated to Silicon Valley and founded what has now grown to be a ten-billion-dollar software company. She had no intention of telling him any real reason for the absence, the new man who was now the center of her life.
Ashok wasn’t very sociable; he had been a nerd all his life. Nerd was okay. Samantha was used to nerds. Most were harmless and socially awkward, but were kind or at least civilized. Now worth billions, he didn’t want to acquire social skills in his middle age. After all, now he could buy the finest women to carry out his darkest, dirtiest thoughts. Samantha had some idea what was about to happen, as he had been a client for years. It wasn’t going to be pleasant, but there wouldn’t be any permanent damage or rules broken. Not all clients were charming or even likable, like Ashok.
“Just busy, baby. You know me. So, where is the bathroom? Let me go and change into my lingerie for you.”
“It’s right over there,” he said, pointing to the small hallway in the suite. She got up, grabbed her large tote bag, and walked in to change and prepare herself. A fat white envelope lay near the sink, in plain view. Ashok didn’t like to pay by credit card or bank transfer, like most of the clients. He seemed to enjoy paying cash, it made the transaction more sinister in some way. She picked it up and counted eighty bills of the same one-hundred-dollar denomination.
Another five-digit night, you go, girl, she thought to herself as if it were a pep talk before a sporting event. She shoved it in the inner zipped pocket with the earlier envelope and zipped it shut. But then she had another thought. The tip was double what it usually was. That meant only one thing: she would earn that extra two thousand by working hard for it. She closed her eyes briefly to clear her mind in anticipation of the upcoming unpleasant encounter.
In about ten minutes, the costume change was complete. She took another deep breath, opened the door, and walked out of the bathroom. She knew exactly what to expect with Ashok.
He looked up to see her in the dark-red, see-through demi-bra with small bows tied above her areolas to hide them. Otherwise, the demi-bra completely failed to cover her perfect breasts. The matching stockings and garter hugged her sexy body with grace. Her tiny panties were over the top of the garter belts, holding up the stockings for easy removal. It was easy to see her landing strip through them, as well as the top part of the lovely, symmetric lips of her pussy. She walked up to be in front of him, sitting on a large chair, for inspection.
“How do you like this, Ashok?” He stared but didn’t smile and said nothing. His stare rapidly turned into more of a glare, and an unfriendly one at that.
He held out his hand, and she walked to it to be touched. He pulled her in and turned her around to plop her nearly naked body down on his lap. With his other hand, he roughly grabbed her breast, fondling it mercilessly, like a drunken sailor in a bordello on shore leave. He began speaking in a new tone that was very different from the one he used just minutes ago.
“Give me these tits, bitch,” he growled as he roughly fondled the left one with his right hand. He pulled one of the demi-cups aside and, baring her nipple, said, “Your fucking tits, these motherfucking tits. I love playing with these tits. You fucking whore, you love it when a man fondles these whore tits, don’t you?” he said with a new meanness in his voice. His demeanor had completely changed. This new man was cold and unforgiving.
“I said,” he paused, still callously mauling her boobs, growling, “you love it when a man fondles these whore tits, don’t you?” This time, his voice was a bit louder and more intimidating.
“Yes, yes, I love it when a man fondles my whore tits,” Samantha said, with a tiny streak of fake submission in her voice.
“Yeah, bitch, you fucking whore. You love to suck dick, don’t you, whore?” He didn’t wait for an answer, continuing with, “I said, whore, you love to suck dick, don’t you, whore? Big dicks, small dicks, fat dicks, tiny dicks, white dicks, Black dicks, Asian dicks, Latino dicks—it doesn’t matter, or does it? You’ll suck any dick, like my brown Indian dick, as long as someone throws you money, isn’t that right, whore?” His voice was darker, meaner, and even sinister.
“Yes, yes, I love to suck dick. I’m a whore.”
“A whore? A whore? No, bitch, you are not just a whore. You are a nasty, dirty, slutty fucking whore. Tell me what you are, bitch.” He grabbed her tit hard and uncomfortably squeezed it, and then pinched her nipple.
“I’m a whore, a nasty fucking whore,” she moaned submissively, her answer leaving out some of his words on purpose to show him he wasn’t fully in charge. “I love to suck dick, any dick. I’m a slut, a fucking slut.” She got off his lap and spun around to her knees, kneeling down between his spread legs.
“Get these fucking pants off me, whore. Get my socks and shoes off, bitch.” She responded like a geisha, silent and quickly responsive to the order. He was naked in seconds. Samantha was efficient at her job. After stripping her client, she returned to her knees in front of him as he sat in the chair. She looked into his eyes. There was no warmth or anticipation in them, only a hollow stare. He grabbed her hair from the top of her head and pulled her down within inches of his cock.
“There you go, bitch. A cock. A motherfucking cock for you to suck like the whore you are. Look at that cock, bitch. Look at my cock. It’s magnificent, isn’t it? Do you like my cock, whore? Well, do you?” The tone was degrading now. Samantha knew her encounter with him was going exactly how he wanted it to go. Nothing unexpected so far.
“Oh, baby, I love your cock. It’s a great-looking cock,” she moaned. For once, she didn’t have to act because it was true. Seven and one-half inches of a symmetrical penis, uncircumcised and perfectly proportioned. The head was smooth and helmet-like. When the foreskin was pulled back, the flare of the crown tapered slightly smaller as the cock got closer to his body. For some women, it might even be a bit too big, but for a woman who has taken literally thousands of cocks in her body over the two-plus decades that cocks have been entering her body, it was indeed a perfect specimen.
“Get that cock down your throat, bitch,” he grumbled. “I said, ‘Suck it,’ you fucking whore.” She pushed the helmet in her mouth and quickly dived down, taking half of it on the first plunge, getting it wet with spit, and then shoving it all the way down her gullet, a perfect deep throat.
“Yeah, cunt, that’s it! Take it, bitch, swallow it whole, just like that!” The sensation was so great that he stopped talking and moaned. Samantha held the cock deep in her mouth and started swirling her tongue on the underside of the shaft, where most of the nerve endings were located. His forceful, angry moves caused tears to drip down her cheeks, smearing her carefully applied makeup.
“Oh yeah, bitch, just like that! Goddammit! You are the best cocksucking whore on the planet! Gag on that cock, bitch!” He moaned as he forcefully held her head down on his stiff unit.
Samantha started sliding the cock in and out of her mouth. “Glug-glug-glug-glug,” she moaned. The deep throat blowjob was indeed world-class, and after a while, he forcefully pulled her hair hard to pull her mouth off of his dick before he shot his wad.
“Say it! Tell me that you like to sell your cunt for money! Say it! Say it, bitch, now!” Ashok was getting out of control, working himself into a frenzy, repeating the nasty phrase again and again.
“I like to sell my pussy for money!” Samantha finally screamed, mostly to get him under control again.
“Of course you do, skank! You fucking bitch! Do you think that you are going to get off that easy, whore? No, bitch, stand up!” He pulled her head as high as he could while sitting down. She completed the action, and with her hair free of his grip, she stood up before him.
“Look at this beautiful body. Look at this beautiful face,” he growled as he grabbed her face to pull it to a wall mirror so she could see herself.
“A man could appreciate this gorgeous body of yours, a successful man, a man of means. But no, you aren’t a woman of class; you are nothing more than a nasty whore that sucks and fucks cock for money. You show off this beautiful body to any man who tosses money at you. Such a beautiful female, such promise,” he spat, shaking his head, “yet, such a waste of a fine specimen. You aren’t worth a relationship; you are nothing more than a cum dump, a fuck pig,” he growled.
She shuddered at the meanness, yet could take the slander because she was used to it with him. It was getting worse with every interaction however. The disrespect, the degradation of his words. She rationalized that there were whores elsewhere on the street who were going through far worse with their johns and for a lot less money than she was. Sam knew from her prior experience to accept any man as long as they didn’t break the rules of no blood, no scat, and no hard beatings. Assholes weren’t limited to Ashok; there were a few others, if one really wanted to know. But Ashok was, if not the worst, close to being one of them.
“Turn around, whore.” Samantha turned her naked body around to show him her nude backside. “Now, bend over at the waist.”
She followed the instructions.
“That’s it, skank. Now, pull those ass cheeks open. Show me your holes.”
Samantha pulled her tight buns apart. Her tightly closed asshole and her beautiful pussy were open and available, giving him what he wanted. She held the degrading pose for at least three full minutes as his hand drifted to them. He roughly slid a finger into her pussy, then a second, then a third. His fingers harshly poked her femininity without passion, only disgust. He continued, and now he was pushing a finger into her butthole again, without any mercy. After a half-dozen plunges into her butt, he changed to pushing a finger into her ass while pushing two fingers of the same hand into her pussy.
“Two in the pink, and one in the stink,” he moaned. “Just like a whore likes it. Isn’t that right, whore?”
“Oh yeah, oh yeah,” she fake-groaned at the vile man. Most women would have already left the degrading scene, but not Samantha; she was a professional. The act was uncomfortable and demeaning, but she kept up her part in the sexual charade. “Poke my holes, baby, use my holes.”
“Now turn around and get on your hands and knees, bitch. You need a good fucking.” As her knees hit the carpet, he got up, and with his massive hard-on, he aligned himself to her pussy and slammed it in.
“Ugh,” Sam moaned. One hard push sank his cock deep inside her. Her pussy was soaking wet after Ashok’s manipulation, so it didn’t hurt when he slammed his cock inside her. A small part of Samantha enjoyed the degradation some of her clients subjected her to. It turned her on in that portion of her brain where darkness simmered. He began to pound her pussy as hard as he could.
“You fucking whore! You’re nothing but a fuck pig, bitch! Take my dick, bitch! You piece of shit whore! Take it, goddammit, take it!” He continued to slap his balls on her ass as he pounded her pussy as roughly as he could. He would slap her bare ass with his open palm. Back and forth, cheek to cheek, as red hand marks started appearing on her beautiful bum. For a few seconds, her mind wandered back to her early days, the Dwayne days, when being abused was more the rule than the exception.
SLAPWHACKSMACK
The sounds were loud, and she felt her butt cheeks burning.
“Oh, you fucking bitch! You want me to come in your pussy, don’t you, bitch?” The merciless pussy-pounding and ass cheek slapping continued.
“No, bitch, you aren’t going to get off that easy. Reach back and pull your cheeks apart again.” She was getting into the hard pounding and wasn’t listening to him. The sex was rough, but once in a while, she actually liked it. To enjoy it, she had to turn off her brain and be nothing but a piece of meat for her john.
“I said, fucking PULL YOUR BUTT CHEEKS APART, BITCH!” He was now commanding her to perform new sex acts. She realized he was talking and pulled the buns apart, exposing her asshole. He pulled out of her pussy and shoved his wet dick into her bung.
“Ohh!” she groaned again. Used to being ass-fucked, her butt ring gave way relatively easily to allow the intruder to enter. He hit bottom again on a half-entry with the first stroke and completely with the second. His balls bounced on her pussy as he viciously stroked his cock in and out of her ass. The climax didn’t take long. He groaned mightily as he blasted his load deep into her ass. After finishing, he collapsed on top of her, his still-stiff dick deep in her stink.
After a minute or so, he moved off of her and sat up on the floor.
“Lick my cock clean, whore. Taste your ass on my dick. You like to eat your own shit, don’t you, whore?” His nastiness was only partially sated after he came. He pulled her head by her hair again and pulled her face above his softening, wet cock.
“Suck it, whore. Suck it clean. Clean your shit off my cock, bitch.”
Without a wait, she immediately moved and lowered her mouth on the dirty cock. Licking and sucking it, she cleaned it of its juices. It didn’t taste like shit because Lennie had given her the first enema as he normally did before leaving the house to begin her nightly sex encounters and a second enema after her first clientcame in her ass to finish their round-the-world fuck session. She smiled to herself thinking about the care and patience Lennie had shown her when he administered her enema compared to the rude, nasty treatment from Ashok.
Finally, the nasty, degenerate client pushed her head away, off his dick. Samantha looked at the digital clock on the small table. It had been an hour and five minutes since she had arrived, well short of her two-hour minimum appointment. Did that mean she still had fifty-five minutes of this continued degradation?
“Get yourself dressed and then get that nasty cunt of yours out of here, whore. You make me sick. Such a beautiful woman, yet you are such a filthy fucking whore, a fuck pig. You make me sick. I don’t pay you for sex; I pay you to leave. Get the fuck out of here,” he snarled,, still panting as he lay naked on the bed.
She picked up her lingerie and silently walked into the bathroom, closing the door. Putting it back into the tote bag, she looked in the mirror, seeing her makeup a mess and drops of white in her hair. She showered in silence, taking the time to clean her most private parts. She washed the smeared makeup from her face and then her hair to get the drops of semen out. A small enema bag helped her clean her butthole of semen. She had planned for every degradation. She dressed, putting on a fresh bra and panties, a plain blouse, and denims from her tote bag. The four-inch black heels returned to her feet, and she walked out of the bathroom door and, without even looking back at him, walked out.
After the lowlight of her depressing evening, Cindy needed to unwind before she drove home. The last thing she wanted to do was to take her bad attitude home to her boyfriend or any of her housemates, for that matter. A thought popped into her mind, and she turned her Audi down the side street. Just a few blocks away was Goldfinch’s, and being a Tuesday night, the crowd was sparse. Turning the keys of her Audi over to the valet and walking in the door and through the lobby, she saw the bar had a man at the far end, and only two tables had pairs of people sitting at them. Her naturally seductive walk did not match the pensive, even melancholy look on her face. Greg was once again behind the bar and, looking up, took note of her attitude immediately.
“Hello, Cindy, or is it Samantha this evening?” Greg asked in a neutral tone, letting her lead the conversation.
She smiled a half-smile and, with a weak grin, said, “I’m trying to transition back into Cindy, Greg. Although nights like tonight don’t make it easy.” Their eyes locked together, and Greg saw the somber attitude reflected in her eyes and defeat in her body language. “Maybe one of your amazing Cosmos will help me get out of this funk.”
Greg immediately went to work, not missing a single step in creating one of his signature drinks. His professionalism was a performance, something to appreciate, and watching his effort helped Cindy forget her nasty encounter, if only for a short while. In under two minutes, he was sliding the drink towards her on a monogrammed cocktail napkin.
“There you go. Now, I can tell that something has you down a bit. Want to talk about it? If you want someone to talk to, I’ve been told that I’m a pretty good listener. Some tell me that I’m better than their psychiatrist. And hey, your only bill is your bar tab, so there’s that, too.” Greg gave her a caring grin.
Her smile grew as she realized coming to unwind at Goldfinch’s was the correct move. She quickly glanced around and realized she could talk in relative privacy, as nobody was near them.
“Greg, you know what I do, and most of the time, the men are appreciative. But sometimes, there are some really nasty people in this world, and tonight, I had an appointment with one of them. It could hardly be called a ‘date.’ It was a shitty encounter that makes me think that people are so fucked up, you know? I mean, not just imperfect like we all are, but awful, bad people. How can those people become so successful and then treat others like used tissue? Sometimes, however, the guy is so fucking rude. Tonight, I heard a new one.”
“What was it, Sam?”
She looked around to ensure nobody could hear them. “I don’t pay you for sex. I pay you to leave. And this was after he enjoyed degrading me completely.”
Greg paused for a few seconds, staring back at the beautiful brunette.
“You don’t seem to have any marks on your face or body, and you walked in here in the sultry and empowering way you always do, so I’ll guess it was what your client verbalized to you more than what he did physically, correct?” She slowly nodded.
“Of all the women I know, you are as aware of the human condition as anyone. Cindy, we both see so many people in our professions. It may be a simplistic answer and one that isn’t insightful, but unfortunately, there are simply some shitty people out there. At least a few of them have bundles of money, more than they could ever spend in their lifetimes. They think that having all that money means they no longer have to be decent to other people. Trust me, it isn’t you, it’s them.”
Cindy stared at Greg, hanging on every word.
“There are a lot of miserable people in this world, I’m afraid to say. And it isn’t necessarily because of not having money. A few of those jerks stay at this hotel, one of the more expensive in Seattle. I know, because I serve them, and they are similarly rude to me. Of course, you don’t have the benefit of being in a public crowd to regulate bad behavior like I do. But I see it all the time. It’s sad, really, for them, I mean. They have all that money and still have a shitty outlook on life and mistreat other people.” He shook his head. “There is simply no reason to be shitty to other people, especially when they haven’t done anything to you.”
Samantha slowly nodded as she tasted the sweetness from the sip of her Cosmo sliding down her throat.
“Sam, don’t let someone else’s shitty attitude affect your outlook on life. Just accept there are assholes, and try not to associate with them.”
“That’s easy to say, but when they are clients, I have to let go of a lot of stuff.”
Greg looked directly into her eyes. “No, Sam, you don’t have to let a lot of stuff go. You’re smart and financially successful. I don’t care how much money you made from that guy. If he made you feel like this, follow those famous words from the late First Lady of the United States, Nancy Reagan.”
He paused for effect and her stare.
“Just say no.”
The words sank in, and she nodded slightly in agreement.
Cindy’s smile grew a bit more.
“You’re right. I’m gonna dump his ass and ban him from SES.”
Greg slightly grinned, but it was obvious he liked what the blue-eyed beauty said.
“I see once again why Lennie always tells me you are the smartest bartender in the world.” She took a deep breath and said, “Thank you, Greg. I needed those words of wisdom.”
“Aw, heck, you just came in for one of my famous Cosmos,” he grinned.
Cindy smiled back, now having left Samantha in the dust for the evening and her poor experience behind her as well.
“Maybe your delicious Cosmo makes your words a little bit wiser,” she chuckled for the first time in hours.
“Probably, but let’s keep that a secret between us, or people will figure out I’m not as smart as they think I am,” he laughed. “After all, I want to keep those good tips coming.” Cindy giggled out loud, so the few men at the tables looked up and stared at the beautiful woman at the bar.
They made small talk for the rest of the hour, with Greg making one more of her favorite drinks as she slowly sipped it down. Greg gave her a favorite hors d’oeuvre, on the house, to help absorb the alcohol. Feeling and looking noticeably better, she smiled at him as they walked to the end of the bar, where she leaned in and gave him a big hug before driving home.
Cindy gave Greg one of her signature thousand-watt smiles. “Thanks, Greg, you’re the best. I really mean that.”
Lennie was again thinking about his girlfriend. She was so busy, and his day schedule did not align well with her mostly night schedule, so he wasn’t able to talk with her too much. He began reviewing the session notes in the SES app to stay up-to-date with her activities. He read the notes she had written about her first encounter, the old man with limited physical skills, the careful lovemaking, and the giggles and laughs.
“That sounds nice. I don’t like her screwing other men, but if that is what she likes, I’m glad she had a good time doing it,” he reasoned to himself, talking out loud with nobody around. “And it sounds like it was a good time for all.” Then, he read the notes from the second encounter.
“Another night with Ashok, just like all the others. If another girl has him for a date, remember to simply ‘go with the flow’ when his degrading words and acts start. His acts aren’t really meant to hurt a girl. No, he does them because he has some deep resentment against women. I think he has the social skills of a twelve-year-old. Just keep telling yourself that it’s his kink, and he doesn’t hit harder than a slap on the ass or tits. Just prepare your mind to be sexually humiliated by a disgusting man, and don’t let it get to you. He will pay you well and then discard you like a used tissue. But he will always let you clean up and shower afterwards. My last piece of advice is that when you leave the room and let the door shut, don’t look back at him. Write up your session notes and forget what happened. Heck, I got a fifty percent tip and got kicked out 45 minutes early.”
Lennie’s eyes opened. What he was reading was disgusting. The disrespect is what bothered him more than the sex. His girlfriend wasn’t lying; it was against her own rules. It nearly made him sick to read what the john had done with her. He slowly shook his head in disgust. With nobody around, he mumbled, “Obviously, this is the downside of what Cindy does. It’s so disgusting. What a sick bastard.”
By the time Cindy returned home, he was fast asleep, snuggled up and spooning a naked Lori. His arm engulfed her body, and his palm was comfortably covering her breast. Cindy stripped, hung up her clothes, and then slid in behind him, forgetting her evening and appreciating the warm body of her boyfriend and her girlfriend sleeping together.
For the next five days, Taylor had either two or three clients each day, all of them meeting her in Las Vegas. She checked into the hotel, which most of her clients used, so she didn’t have to leave the property frequently when going from client to client. There was no convention she had to attend, although if pressed, she could name one, as there were business conventions of some kind in Las Vegas nearly every week of the year. All but one of her clients were high rollers, and they were comped free suites because they were such big gamblers. The casinos referred to them as “whales” due to their spending habits. As they were all worth at least half a billion dollars, they paid normal SES rates without a discount and tipped very well. Taylor considered them “whales” as well.
It was the second consecutive week that Taylor found herself in Las Vegas, meeting with clients. Taylor talked with Mike every day, and Mike now knew why she was leaving town, but he didn’t want to know the details. In fact, after the scene at the Mexican restaurant and her belated confession, she would go out of her way to discuss any related topics with Mike immediately. Mike told her specifically that he didn’t want to know the details for now, only when she had a full schedule and when she would be free to talk, or when she would be returning home so they could be together.
He had accepted her profession, albeit with some uncertainty. He figured that he didn’t have to like sharing her, especially when they would get together for an evening of unadulterated sexual pleasure. Her outstanding blowjobs were a result of lots of practice; that was for sure.
She had worked in Vegas for years, and every time she was there, she was amazed at how much the skyline had grown. After all, she had been a sexual pro for 30 years and first visited Vegas in the mid-90s. Most of today’s finest hotels hadn’t been built yet. When she started, she had even worked in a few of the original hotels from the 1960s and 1970s on the original Strip, as well as some from Old Downtown off Fremont Street, most of them now long gone and replaced by bigger, more extravagant properties.
This time, she was staying at Encore at Wynn Las Vegas. While there had been even more extravagant hotels, many high rollers still stayed at Encore at Wynn Las Vegas. Every room was a suite. She had eight appointments in four and a half days, one or two each day, and an overnight date for four nights. The clients were from all over the country, and Las Vegas was the perfect place to meet. None of the clients ever had any idea they were sharing the same woman for exclusive personal entertainment of the caliber Taylor delivered.
She knocked on the door of room 3462. The door opened, and an elderly, diminutive man answered.
“Taylor! Oh, I missed you so much! Glad to see you again!”
“Barry Crawford! How are you doing? You are looking good. I have been thinking about you a lot recently.”
She was two inches taller than he, even without heels. Barry liked his SES girls to wear heels, no matter how much they towered over him. They passionately hugged and kissed, her DD breasts smothering his face. He loved seeing Taylor, although Samantha was his top favorite. If he couldn’t have Samantha, he was happy with Taylor. Or Maria. Or her friend, who didn’t escort much, Lori. In fact, all of the SES girls were fantastic.
To read the complete story you need to be logged in:
Log In or
Register for a Free account
(Why register?)
* Allows you 3 stories to read in 24 hours.