Lennie and Samantha
Copyright© 2025 by dawg997
Chapter 1
Erotica Sex Story: Chapter 1 - 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 Consensual NonConsensual Romantic Lesbian BiSexual Heterosexual Fiction Humiliation Gang Bang Group Sex Harem Orgy Interracial Black Male White Male White Female Anal Sex Cream Pie Double Penetration Exhibitionism Oral Sex Prostitution
An older man and an expensive escort accidentally meet at a bar.
She glided flawlessly into the lobby of the expensive hotel. Immediately, the three men standing in the lobby, conversing together, stopped mid-sentence and stared. It was impossible not to stare after she gave the three men that deep look. Her haunting beauty was more powerful than any will the men had to ignore it. In an instant, they were transfixed by the gorgeous woman walking by them.
She was breathtakingly beautiful. Classically female. Tall. Firm, large breasts and slender, athletic legs that had an incredible set of ass cheeks riding over them. Her sexy cocktail dress hung on her frame like a glove, showing off her incredibly proportioned body. Her hips were curvy but not too wide, and balanced perfectly within her hourglass-shaped body. Her thick, long brown hair had just enough curl in it to be authentic. The gorgeous, deep blue eyes were like lasers, together with that infectious, perfect smile. Ringlets framed her beautiful, classic, model face with high cheekbones and lips that were thicker than most but still natural.
She was a tall woman—two inches less than six feet, lithe and trim, with shining healthy skin. She had been an athlete in high school and college, and it showed. Her arms and legs were toned, yes, but it was more than that. There was an aura of confidence to how she moved, confirming she was completely in control of her body and her surroundings. Everything on her was authentic original equipment; there was no fakeness about her anywhere.
She entered the elevator and punched 32. The lighted button glared back at her as the display counted the floors upward. When she stepped out, she turned left and found room 3245 and knocked on the door. A man in his late 50s, still wearing his extravagant tailor-made suit, opened the door.
“Hello Sam, god it’s so good to see you again!”
Her smile was wide and inviting. Her arms reached around the back of his neck as she brought her mouth up to his, giving him a long, wet kiss. With a hint of a sultry giggle, she replied, “Hi, Roger, it’s so good to see you again, too. How long has it been, three months? I hope you haven’t been enjoying the company of other girls and ignoring me.”
“Oh gosh no, sweetie. There is no one else, only you, in my life. Jessie, my personal assistant, is the only one who attends to my needs, like it’s always been. I just had her tested along with me when I went to Sharon yesterday, since we were both coming to town. It keeps Sharon happy when I go to her for my testing instead of her chasing me down, you know? But Jesse is nothing more to me than a sexual safety valve. You’re my girl.”
She smiled. Tonight was going to be a continuation of three months ago. She remembered as if it were last night.
“You are my everything, Sam. It’s been hellishly busy at work, and I’ve been out of the country. It’s because I’m no longer VP of Worldwide Sales; they promoted me to CEO a year earlier than the plan. And it’s been incredibly successful. During that time, I’ve already added a hundred million to the company’s bottom line, and I receive 7 percent of that as a bonus. This is the first chance I’ve had to return to Seattle to see you, now that you don’t travel the way you used to. You wouldn’t come to Europe to see me, so I’ve come back to see you. Now I’m back, and I’ve so missed what I’m looking at right now.”
He pulled her close and gave her another wicked, wet kiss. She molded her body into his chest so he could feel her large breasts crushing into him while he inhaled her intoxicating perfume. “God, I’ve missed this,” he murmured. His hands tightly roamed her perfect curves as their wet mouths kissed, his hands seeking to touch every inch of her perfectly proportioned body like a jewel thief in the safe trying to gather every last bauble before he made his break.
She wasted no time and started rubbing his crotch, feeling his growing manhood. “Fuck me, Roger,” she groaned in his ear as he felt her warm breath against his skin. “I want you to come in me with this magnificent cock of yours. You’re girl is here, baby. Fuck your girl. Fuck me now.”
He had no desire for another drink; clothes fell from both of them in seconds. She dropped to her knees before him, and in hardly any time, his hardening cock was in her mouth. She sucked it a few times to get it wet as it grew rock hard, and then plunged it down her throat until his pubic hair was hard against her nose. She held his cock deep within her throat, and time stopped for him. She rippled her tongue on his member as the deep throating continued and her nostrils flared, sucking in oxygen to stay conscious.
“OH FUCK!” Roger gasped. “Jesus, Samantha, how do you do that thing with your tongue? Blow me, baby, suck that hard cock!”
As she felt him getting close to coming, she let off and pushed him back to the couch in the elaborate suite. Climbing on top of him, his hard staff drove between her slender, curvy legs. Her next move was to drop her body onto the hardness in one swift motion, burying his hard cock in her wet pussy. She rode him hard, passionately, like only a true girlfriend could. Leaning forward, her mouth crushed his, combining their wet tongues and saliva.
She rode her mount, humping him powerfully and forcefully. His hands found their way to her soft, natural, perfectly formed tits and mauled them with a frenzy. He didn’t last long as Samantha slammed up and down, riding his hard shaft. As it was the first time in almost a week he had come in a woman, his sperm blasted deep into Samantha’s wet, tight hole. She let out a squeal as he gasped and grunted.
It was like their ongoing encounters of the last seven years never had a break. She got him off like no other woman in his life, ever. Even his two ex-wives. After he softened, she rolled off of him and lay her naked body next to his. Both were still panting as she fanned her long, soft brunette hair onto his chest. Her scent was exhilarating to him. After what seemed like ten minutes or more, he spoke.
“Really, Sam, I was serious a few months ago. Marry me. I’ll make you happy, and it will be worth your while. You’ll be rich, and you can quit escorting forever.”
She paused for what seemed like a long silence before she spoke. It was not the first time she had heard such a statement from a rich client.
“Roger, you are a fascinating man, but we’ve talked about this. I can’t marry any man who has hired me. No matter how sincere, I’ll always be a whore to you. It’s just human nature. I don’t want to be just arm candy for a husband; I want to be an equal. That can’t happen with us. You know I’m always here for your pleasure.”
“I’d never ask you to sign a pre-nup, Sam. You’d be worth half of a three hundred and fifty million dollar estate. The corporate jet is at my disposal, you know. Of course you do, because you’ve flown on it. It could be yours to use anytime you want. Paris for lunch with your friends. Or catch a tan on Kauai.”
“I know, and I truly appreciate it, Roger, you know that. And you can have me for a whole lot less than one hundred seventy-five million dollars.”
“But I love you, Sam. You know that.”
Samantha sighed. Roger’s proposal was the third in two years from a man worth well over a hundred million dollars. But she knew what her position would be in the relationship. A whore could never be an equal. She could only be a trophy, a prize, another symbol of his success. And never accepted by his adult children or close friends as a wife, only a gold-digging bitch.
“Roger, let me ask you a question. What’s my favorite color?”
“Huh? What do you mean?”
“Roger, it wasn’t a trick question. You don’t know, do you?”
Roger lay silent.
“Which university did I attend? What do I like to do in my downtime? Do I have any family? If you thought of me romantically, these are the simple things that you would have known for years. By the way, Roger, your favorite color is red, you were an undergrad at Stanford, and got your masters from Wharton. When you aren’t working 80 hours a week or banging my brains out, you like to paint shoreline and mountain scenes using watercolors. You divorced your second wife after you found her in bed with your attorney. Your first wife died in a car crash after giving you three fine sons. Of course, when Ryan died after that accidental Fentanyl overdose, now it’s just Anthony and Thomas, but Anthony’s wife Mindy is about ready to pop with your first grandson.”
Samantha’s eyes went wide as she realized she had let out a secret she wasn’t supposed to.
“Oops, I just let the cat out of the bag. Mindy told me that it was a boy four months ago at the dinner we attended with them. Please promise me you’ll act surprised when you are told the sex of your new grandchild.”
“How do you know these things about me?” Roger blurted out, his head shaking.
“You introduced me to your family years ago, remember?”
“But that was five, no, six years ago, a year after we started being together.”
“I keep in touch with them because they are part of your life, and you introduced me to them. That’s part of my job. You understand, right?”
Roger was quiet as he softly caressed Sam’s left breast in the palm of his right hand, and he continued to inhale, enjoying her feminine scent. “Wow. You’re right. Do I take you for granted that badly, Sam? How is it that you know so much about me, and me so little about you?” he said, a bit dejected.
“Roger, don’t feel bad. I’m an escort, and one of the best escorts in the world. That’s not me bragging: it’s rich man after rich man telling that to me. As an escort, I have two jobs. The first is that I’m a companion to the man who has hired me. I use this beauty, and the brains I was given to support you and make you look good in front of your friends and business associates with class and dignity. To do that, I have to know you fairly well. I never quit trying to learn more about you. The other job is as your wanton whore, supporting you physically and emotionally while digging into the corners of your mind to find your wildest sexual fantasies and bringing them to life. You pay me very well to perform both of those roles. I’m confident I’ve succeeded in both.” She pulled her head up off his chest and looked into his eyes, looking for confirmation.
Roger nodded and sighed but stayed quiet. Deep down, he knew she was once again correct.
They lay on the couch naked in each other’s arms. “Let’s just lie here, Roger, and enjoy me for what we have,” Sam whispered.
Roger was quiet for a long while. “Promise me, Sam, promise me that no matter what, you’ll never leave me. I know you are with other men, but there is nobody else like you. I need you, Sam. You know me better than anyone I know, even myself.”
“I’ll always be available to you, Roger. And I’ll always be me.”
Moving back to the pillow, she looked up at the ceiling, and her heart sank. A normal relationship with a man who would respect her was the one thing she had never experienced. Yet it is what she wished for the most. Roger couldn’t see, but a single tear fell from Samantha’s eye and down her cheek.
Lennie Roberts was 67 years old. The last six months had seen him spending money. A lot of it. Not wasted on trivial bad habits, but things like a new wardrobe, a new home, a new car, and a nice vacation. Money spent on things that he wished he’d have done years ago. Life doesn’t happen on the schedule you wish, though. He had lost most everything over a decade ago. In the last two months, he had retired from a company he started with a friend just two short years ago. He bought a big house with a grand view of Puget Sound, which he moved into last month, and a new Ford Expedition (he was tall and liked a big 4x4 with ample legroom). He had just arrived home from 2 weeks in Hawaii, where he flew first class and vacationed on the beach at a private home he found on Airbnb. A big guy, he’d been out of shape, but now, he was working with a personal trainer he’d hired for the last year. He’d been losing weight as he gained strength and shape. He hadn’t felt this good in years.
Lennie had earned a business degree and worked in corporate computer software sales for 20 years, but then got burned out. After taking time off for a few months, he started a totally different business, a small coffee shop chain with in-house roasting. The shops also had a pastry bakery and a juice bar offering freshly squeezed juices and smoothies. It went well for eight years, growing quickly until the 2009 economy crashed and the stores were sold. He barely broke even as the value of the stores crashed with the economy. A year later, his wife died of an aggressive form of cancer.
His only son, Danny, was on his own in his mid-20s, but kept in touch, like most busy kids in their 20s. It was over a full decade since he was forced to divorce his wife of 16 years, who was diagnosed with Stage 4 cancer just a year before she died. Pain drove her to be prescribed Oxycodone in high amounts. The drugs numbed her mind and wore her down. She was mentally off the deep end and had secretly turned all of her affairs over to her attorney brother to manage. Somehow, her brother and father convinced her, in her drug-induced state, that Lennie was the cause of her aggressive cancer. The brother immediately saw his chance to screw Lennie and did so. Lennie never did get along with his brother-in-law. There was always a simmer of disgust under the thin veneer he kept up when the two were together for the occasional extended family events. Mary and Lennie had married late in life, the first time for both of them. Danny was their honeymoon project, and they were successful. They tried again after Danny was born, but no luck; his wife couldn’t bear children again. In hindsight, it was probably best after her attorney brother ripped up his financial life as his wife succumbed to the nasty disease.
It was by accident that he found out their plans. Lennie was a coach for Danny’s CYO basketball league. He had to send out an email for the after-season party to a family that missed it the first time it was sent. Lennie had typed out the details and was too lazy to do it again for just one family. He figured he could use the deleted but not erased email from the family computer, and found it. However, he also found another from his wife’s attorney brother. What was weird about it was that it was sent from not his family email address but his attorney’s office email address, the first time Lennie ever stumbled across it in 15 years. In it, the attorney brother was making plans with his wife to fly out to Washington state and work with a local attorney to remove all of their marital assets and life insurance policy from the family to be controlled by the attorney brother. As he managed to set up his sister as the life insurance owner of both policies when they were set up—a mistake on Lennie’s part he never realized—she would be able to steal the payout from him by re-assigning it to another person without his knowledge.
He never knew. After all, he trusted her completely.
Mary was mentally useless, taking huge doses of Oxycodone for pain relief. She was constantly high and out of it. He’d ask Mary a few times what she was doing, and she just looked at him, mumbling a few phrases from the brother’s email that made no sense. To delay the assets transfer, Lennie was advised to file for a divorce to stop her. Lennie stayed with his wife, now weak and unable to care for Danny on her own, while living in separate bedrooms.
The divorce continued. They had to sell the home in a terrible down market, losing nearly all of the $200k in equity built up over the years. Four months after the divorce, she died. Lennie, now kicked out of his own home, which he had put thousands of hours into maintaining and improving, had been forced to sell it to cover the divorce. He had rented a two-bedroom apartment in expectation of being the only parent soon, living alone. Two months later, Mary was gone.
Life for Lennie was meager, but he loved and supported his teenage son, Danny. Danny had emotional problems dealing with his mother’s death, but Lennie kept doing what he could to support him. Relatives who lived 40 miles away tried to help, as did a few families from school, and also Lennie’s best friend, who was also Danny’s godfather. Danny almost flunked out of high school, but with the support of his school counselor and Lennie working together, Danny graduated and turned 18. The attorney uncle revised Mary’s will to create a trust for Danny, but also with obtrusive control over his life, as he was named the new administrator. The uncle had control of the trust until Danny was 30. As the administrator of the will, he received a 2% annual management fee, and all related expenses were also to be paid for by the trust. He took every dime he could legally get away with, including spending a quarter million to fight Lennie in court when Lennie tried to get some say in how the money was managed for his son. Lennie, with no money left after getting a quarter of the insurance but all of the bills as well, had to let contesting the will go.
Danny went away to college, paid for by the trust set up through the insurance money. The uncle would use trust money to “visit” Danny; visits to the California city lasting for a week at a time, only seeing Danny a few hours a couple of times each visit. He spent as much trust money as he legally could, staying at the finest hotels, eating at the finest restaurants, renting specialty sports cars, and making up wild justifications, when in reality it was just a vacation using Danny’s trust fund. Usually, his wife, Danny’s aunt, accompanied him. While she had nothing to do with Danny’s trust, she helped spend the money on fine dining and taking excursions with her husband.
The uncle, who had lived in the Midwest, had met Danny in person only three times before his mother died of cancer, demeaning Danny every chance he could. He would berate Danny for his choice of university, how his kids (Danny’s older cousins) had been so much smarter and successful. He would tell Danny that if his mother were alive, she would be ashamed of his choices in life, even though Danny did little wrong other than being depressed by his life’s circumstances. One day, when the uncle showed up at Danny’s college unannounced, he took him out to dinner and berated him for how poorly he was doing in school. Danny had little choice other than to take it if he wanted college paid for. The uncle had written into the will complete control of all assets solely at his discretion.
Lennie was nearly broke and in his late 50s. A new career for him was simply not an option. He bought a late-model minivan with the little remaining money he had and started driving Uber and Lyft for 5 years. He worked nights and weekends around Seattle, making relatively good money compared to the day drivers. The driving part was easy; as a kid, Lennie had a car given by his grandma, who was too old to drive, and he got his driver’s license the day he turned 16. His customers were often entertaining; the groups of college kids and twenty-somethings were the most fun, as long as a fresh plastic garbage bag was open under the driver’s seat and ready for the late-night pukers who couldn’t handle their liquor. Driving was second nature, and even when he got stuck in traffic, Lennie didn’t get upset—figuring it was just part of the job. Now he lived in a small rental home in a less desirable neighborhood near the airport, unlike the one in the Eastside suburbs where they were married.
After Mary’s death, Lennie dated a few times. He dated several women, slept with two of them as well, but there was so much emotional damage that nothing lasted. Truth be known, he felt like a fish out of water. Danny moved to California University after his mother’s death when he graduated from high school, mostly to get away from the bad memories. While Lennie’s rideshare driving job paid the basic bills, there was little left over for retirement or even just simple entertainment, such as travel, concerts, or dinner at a fine restaurant with a lady friend.
A few years later, he received a call from his friend Josh, with whom he had done a lot of business in the coffee industry, mostly supplying espresso machines for some of Lennie’s coffee shop customers who bought his coffee.
“Hey, I want to show you something, Lennie, but first you need to sign a Non-Disclosure Agreement, OK? It’s something I invented, and I need some help to get it going. Interested?”
Always looking for some way to improve his lot in life, Lennie was impressed with what his friend shared. He had invented a product, had applied for and received a US Patent on it, after a patent attorney had determined nothing like it existed.
The patent was strong. The good friend invented a new tool that cleaned a commercial espresso machine steam wand faster, cheaper, and easier than it’s currently done, which involves using a bar rag immersed in a liquid chemical solution to rub down the steam wand. Milk on a hot surface couldn’t be wiped clean with just a wet rag. It dried instantly and created a film that attracted organisms that could make people sick. Only wiping with the expensive solution could make the milk solids disappear from the stainless steel wand that frothed the milk, making foam in the stainless steel pitcher.
The invention was a simple yet ingenious design. It was a silicone bottle with an internal tube chamber. Simply squeezing the bottle forced some of the cleaning solution from the outside chamber into the smaller inside chamber through an internal flap, and then sealed when the pressure was released after the bottle was squeezed. On the inside of the tube, small flexible silicon nodules scrubbed the wand clean. It saved 90 seconds of barista time each cleaning, and it was required by local health departments to clean the steam wand every few minutes, at least 60 times a day. The benefits were easy to understand for both management and the baristas.
Baristas, mostly women, loved the fact that their fingernails and cuticles weren’t cracked and split anymore from dipping fingers in the cleaning solution all day, where the cleaning rag was soaked. It was a small thing, but a big deal for baristas. They loved it.
This call from Josh went from a plea for help to a solution to his need.
“So Josh, how big is the market for this, anyway?”
“There are over 300,000 espresso machines in America and more than that in Europe. We could sell the silicone bottle and supply a cleaner. We could make maybe 75% margin on the bottle, and 25% margin on the cleaner.”
“What would stop the coffee shop from just buying the bottle and then buying their own cleaner?”
“Nothing, I guess. Three different chemical companies split the entire worldwide market. The bottle could sell for $45 or perhaps $50, but would cost about nine or ten bucks to create. Then we would find one of the existing cleaners, and buy it wholesale for around fifteen cents per batch, and sell it for a quarter per batch. One batch is good for six cleanings. Each machine in a volume coffee shop would use ten units of cleaner a day.”
“That’s not a lot of money; heck, half of those users probably only make a dozen drinks a day, like bars and such. They wouldn’t change. So your market could be around one hundred and fifty thousand machines. And how long does the bottle last?”
“Maybe a year, it’s high tensile silicon. So a dollar a day profit in the cleaner and forty in the bottle. That’s about four hundred a year in gross profit per machine.”
“But any company that makes the cleaner you source could just undercut you, right?”
Josh sighed and felt a little depressed as he hadn’t thought about the business case that far.
Lennie smiled. “Look, how about this? Instead of selling the bottles for fifty bucks that will last a year, instead give them away for free.”
“That makes zero sense, Lennie.”
“And then, with the free bottle, sell them a year’s worth of cleaner in a case for a buck a batch. Never sell the bottle by itself. That way, nobody would buy a cleaner by itself because they can’t source the bottle. You have a strong patent, right? Six uses per batch, ten batches a day, is 3,650 batches a year. Your costs for the bottle and a year’s worth of cleaner are maybe six hundred bucks. Instead of making 400 a year and competing with your supplier, you make over three grand a year per machine and have no competition.”
“Damn, Lennie, that’s smart. However, we still need another forty thousand to make a second prototype. And then I figure, after talking to manufacturing specialists who make other silicon parts for espresso machines that it will take another quarter million to make the first run of 20,000, the wholesale cost of the cleaner for those bottles, and basic infrastructure like a website to sell it, some in-house people for customer service and to present at trade shows, and a logistics company to ship the orders. I’ve hit up everyone, and the initial money from a friend was spent on obtaining the patent and creating the first prototype. The design works, but the top needs to be redesigned.”
“Ok, I can get the money for that, and the quarter million it will take for initial manufacturing and setting up the core of the company. But it will cost you half of the company.”
“That’s a lot, Lennie.”
“Well, Josh, fifty percent of a lot of something is better than a hundred percent of nothing.”
Josh thought about it and agreed. He drew up the papers with his attorney to make it happen.
Lennie had remembered his late wife’s will, and in there, Danny had a few options to get his trust money released early. One of them was whether Danny had a legitimate business opportunity that would benefit him. When Lennie told Danny about the idea, he was at first skeptical. After Lennie presented the written business plan that showed he could be a millionaire with even a 5 percent market share, he jumped at it. After some touchy negotiations that had the uncle saying no, Danny got an attorney experienced in Wills and Trusts to negotiate with his uncle. Danny got the money transferred and became a minority partner with a quarter of the company. Lennie became the CEO and owned a quarter of the company. His inventor friend, Josh, now worked under him and owned the largest share, 40%, and his original investors owned the final 10%. The natural division of duties between the two meant there was little conflict between them in running the new company.
Lennie, with his corporate software sales background and coffee shop knowledge he learned years ago, was a natural fit as CEO. His experiences were perfect for this new company. The sale itself was easy; baristas would see the one-minute demonstration video on the website and immediately wanted to switch. Corporate management of larger chains saw the financial benefits in addition to making the baristas happy. Lennie had years of experience presenting to corporate types when selling software; their new offering was much easier. After all, corporate types wanted to increase profits, decrease costs, and, if possible, make their workers happier.
The new invention did all three.
Sales took off. In just two years, the company was over $50 million in sales, with a 65% profit margin before taxes. And that represented just over 8% of the potential market. The company’s growth kept exploding. Existing customers would reorder the solution each year as new customers were catching on and getting happily involved with the new way of cleaning an espresso machine. As the cleaning tool was patented, there were no other options other than the old, messy way the industry had used for over 40 years.
It was great to succeed after all this time—greater than his wildest dreams—but Lennie was now 67. He was still healthy, and now, with his first distribution check of over $9 million a year before taxes, he was netting nearly $5 million this year after taxes. With the company on track to double sales in the next year, Lennie essentially retired. This was the plan: to get the company running and turn it over to experienced management while retaining his portion of the stock. He would still get involved if the company had to make a presentation to a large corporate client, but would be done with being involved in daily operations. After finding an experienced CEO and offering him a large six-figure earnings package, Lennie and his partners did exactly that.
As he still owned a quarter of the company, he got a quarter of all distributions. His money problems were over for the rest of his life. Lennie had money to burn, and because Danny was getting the same amount in distributions, he was also a multi-millionaire in his late twenties.