Lennie and Samantha
Copyright© 2025 by dawg997
Chapter 3
Erotica Sex Story: Chapter 3 - An older man, who found financial success later in life after enduring years of anguish, grief, and bitterness, unexpectedly meets a stunning, high-end escort at an upscale bar. Neither had sought love for over a decade, their pasts having long since closed that door. Yet, what they had both stopped believing in suddenly seems possible. Two very different worlds collide.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Mult Coercion Consensual NonConsensual Rape Romantic Lesbian BiSexual Heterosexual Fiction Uncle Humiliation Rough Sadistic Gang Bang Group Sex Harem Orgy Interracial Black Male White Male White Female Anal Sex Cream Pie Double Penetration Exhibitionism Oral Sex Prostitution Violence
She had said “a few days.” That would have meant returning on Thursday or Friday. Here it was, early Saturday night, and not even a text. Lennie’s attitude had definitely soured since Tuesday evening. Earlier in the afternoon, he had left a message on her phone. “Cindy, I’ve been thinking about you. Please call me when you get this. Take care, sweetie.” Then he realized he had called Cindy’s phone, but she had been Samantha since Wednesday morning, not Cindy, and wouldn’t get the message.
It was like that damned elephant in the room just shit on him. He wanted to get an intelligent perspective on his problem. And he wanted to drink heavily. Looks like another trip to Goldfinch’s, he reasoned. He needed a worthy analysis, and that meant talking with Greg.
It was still early, and the crowd was sparse. There were no conventions in town. It wasn’t a bar with live music or entertainment except for a piano player with a baby grand on the weekends, which wouldn’t start for another hour, so it stayed fairly slow.
“Greg, you have to help me. I’m so messed up right now.”
Greg looked at his true friend. “Let me guess, woman problems, Lennie?” It was like Greg could read minds. No, he couldn’t read minds, only faces and body language.
“Yeah. I’ve been seeing Samantha.” Lennie knew not to use Cindy’s real name.
“Wait, I didn’t think you were much for that kind of girl, Lennie. I know you have the money, but...” Then Greg realized the truth. He wasn’t the smartest bartender in Seattle for nothing. Thirty years, and he could read faces like others read the sports section of the Seattle Times.
“You’re not ‘dating’ her,” using his fingers to make air quotes, “you’re dating her, like for real, right?”
Lennie nodded. Nothing came out of his mouth. His puppy dog eyes told Greg everything he needed to know. He leaned over the bar toward Lennie and whispered, “Can we talk frankly?”
“Why do you think I’m here, Greg? Oh, and before I forget, can you call over and reserve a room for me? I’m getting hammered tonight. No port for me, pour me a Buffalo Trace. Make it a double, on the rocks.”
Greg dropped a single large chunk of ice into a glass, poured and served the smooth Kentucky bourbon to his friend. Lennie said in a low voice, “Look, you know what she does for work, right?” Greg nodded silently.
“How can I get closer to her when I know she is with other men, doing what she does? Look, I know how fucking stupid I must look here. I’m dating one of the most expensive escorts in Seattle, probably the West Coast, who says she’s crazy for me and I’m crazy about her. She knows things about me that I don’t even know about myself. She has this special ability to look inside me that opens up my heart. I never thought I would ever feel this way again.”
Greg nodded. “Ahh, love. Doesn’t matter how young or old you are—when it hits, it hits. Don’t deny your own feelings. Look, there are issues that you two have to work out, but let’s start with the basics. She hasn’t lied to you or purposely misled you, has she?”
“No, Greg. That’s just it. She has been honest about it, completely truthful, but never once tried to rub it in my face. I think she knows how I feel about it, and she is having her own issues with how to deal with it, or more like dealing with me, while she does what she is good at. I don’t want to look like some stupid remake of Pretty Woman, when Richard Gere saves Julia Roberts, and they live happily ever after. It’s chickenshit on my part, I knew what she did that first evening I met her. You know, it was here at your bar.”
Greg nodded and recalled that evening well. “Yep, she’s a Cosmo girl.” Greg categorized everyone by their favorite drink. In his mind, what one ordered reflected a bit about who they were. His Cosmopolitans were feminine and classy, just like her.
“Look, Lennie, I can’t say exactly what you should do. I will tell you one very important thing: communicate with her. Sounds like she is looking to work with you, not work against you. She has her own life and history long before she met you. I’d just say to take her to a place where you cannot be disturbed, a nice place, and just be honest with her. Try to understand her, beyond what she does. Maybe going down that path first will give her and you a better way to talk about what she does. She’s a big girl, I think she can work with you as long as you both try.”
“Why does she still escort, anyway?” Lennie asked out loud, not necessarily for Greg’s benefit. “She owns a Lake Washington waterfront condo in Kirkland worth a few million at least. She has an investment portfolio in the stock market worth millions of dollars. That night, she was here when we met her, and she made twenty grand in 24 hours with two appointments. And then another ten grand the next evening. Geezuz, Greg, that’s a lot of fucking money to get laid, you know? People who throw around that kind of coin are in a different league. How can I even compete with their lifestyle?”
“You’re kidding, right?” Lennie stared at Greg’s smirk as he shot him down. “Look at yourself, you’re worth millions. And with that company you started, you’ll be backing up the truck to deposit that money in your bank account until you turn senile and forget how to spend it.”
Greg paused and stared directly at Lennie.
“That’s got to be maybe two years, three years tops.” He kept a straight face as he delivered the line.
Lennie saw through the senile old man reference and laughed, breaking the tension. “Fuck you, barkeep!” Lennie chuckled as his attitude lightened up. Greg was indeed the finest and smartest bartender he knew.
“Anyway, you’re a good guy, and she seems to be a good person in addition to being one of the most beautiful women ever to have graced my bar, so cheer up and think positively. Look, it’s a corny saying, but my dear departed Granny said it, so you’d better not dis my late Granny, “Where there’s the will, there’s a way.” The question is, do you have the will to work through this with her?”
That was Greg for you, he thought. Always cutting through the BS and getting to what’s important. It changed his attitude, and Lennie held up his empty glass and pointed at it to Greg, who was now at the other end of the bar, serving another customer. Tonight, he was going to be a happy drunk and a man with a hangover tomorrow.
When Lennie woke up, his head was pounding. Afternoon sunshine filtered through the window. The clock said 1:16. Hmmm, this is a hotel bed, I’m downtown, he thought to himself. They knew him so well at the front desk that they just automatically gave him a late checkout. He looked over to the table, next to the bed in his room, and there was a bottle of water and two small packs of Tylenol. Thanks, Greg, you da man, he thought to himself. Greg had made sure the water and tablets would be there. Greg knew his customers.
That reminded him that he was going to get Greg and his bride a long vacation week at Rosario resort on Orcas Island in the San Juans. It was a mansion, accessible only by boat or by air, built by an early Seattle mayor, a rich shipbuilder over a century ago. Now it’s a hotel resort with a great chef and deluxe service. And a round trip on a Kenmore Air seaplane, they had those seaplanes that took off from Lake Union in Seattle and landed right at the dock in Eastsound. Yeah, Greg will impress his bride of 30 years, Lennie thought. He’d order and pay for the trip later today when he got home.
He reached over and picked up his phone. No calls or texts from her. His attitude soured, but then he remembered what Greg said. Did he have the will to work it out with her? That got him thinking. She was worth millions in that condo alone. And she sure can generate a lot of cash, quickly. She had money stashed away, lots of it. So why did she still escort? If it wasn’t the money, did she just like to screw strange men? Lennie shuddered. He would have to wait until he saw her next. Why doesn’t she call? Ideas in his mind swirled ‘round and ‘round. Crap, he thought to himself, he sounded like a fucking schoolgirl.
It was 8:30 on Sunday night. Lennie hadn’t heard anything from Cindy. Not even a text. The void of communication was eating at his confidence. He was home and intended to stay there instead of going out. The hangover lingered; he needed to eat something. A local bar had great burgers, so instead of driving, he walked the mile down the road to a small retail strip. Upon arriving, he sat at the bar. Bob “don’t call me Roberto” was the bartender and owner. Seeing Lennie walk in the door, he slid Lennie’s favorite draft beer to him as he was sitting down on the barstool.
Bob had owned the bar for nearly 20 years. It was his life’s dream come true. Arriving from Mexico as a kid, he worked the lettuce and strawberry fields in central California and the hops harvests of the Yakima Valley in Washington. He received his green card, joined the Army for four years, and eventually gained citizenship. Bob did it the right way, and if you wanted to hear someone swear at the millions coming over the border illegally, just ask him what he thought of uncontrolled immigration. Bob was for anyone who wasn’t a thug or a drug dealer to come to America, but he was a stickler for doing it legally. He also couldn’t understand why Congress and the President refused to write a law for so many years that made sense for all. It didn’t matter which side was in power; they all seemed to screw it up royally.
Bob was another exceptional barkeep; he knew his customers as Greg did at his bar. Except Bob poured beer and hard liquor, forget those fruity drinks that Greg made. Nope, Bob was proud he couldn’t mix more than the occasional Margarita, and he served his whiskies one of two ways, rocks or neat. There were a half-dozen reds and whites; the selection was simple and basic, but all were priced very competitively, and all of the wines tasted well above their price. The beer was ice cold, poured in frozen mugs. He cleaned the 15 lines that ran the beer from the keg to the tap every month. If a beer didn’t sell well enough and the keg sat for too long, he would exchange it for another brand. The beer always tasted perfect from one of Bob’s taps. He took pride in his establishment, and it showed.
“You are looking sad, my friend,” Bob said quietly, in his accent that revealed where he was originally from. “Tell me, what is wrong?”
Lennie sipped from the frozen beer mug. He liked Bob for so many reasons. “Bob, I’m an idiot. And an old one to boot. I met a beautiful younger woman and am falling for her.”
“That sounds like a problem worth having, my friend,” Bob answered, a look of curiosity on his face. “There must be more to the story.”
“Yes, there is.” The bar was slow for a Sunday night. Lennie looked left, then right, and leaned forward. “There’s no easy way to say this, other than just to say it. She’s a high-priced escort.”
“Oh my friend, you’ve told me you see working ladies a few times a year, but you fell for one? You have money to pay for one, but I can’t believe you would do that.”
“That’s just it. I met her at a downtown bar, and I didn’t figure it out at first, but she was working and waiting for a client. Afterwards, she came back to the bar, we got into a conversation, she revealed what she did, and then asked me out for a date. Not an encounter, but a regular date. She even told me her real name. And oh my, she is so beautiful. Here, look.”
Lennie held up his phone and found a picture of her from the day they ate fish and chips at the beach. In the photo, she had her sunglasses on top of her head and was flashing a huge smile. The picture revealed her beautiful blue eyes and long, brown, curled locks framed her face, prompting Bob to do a double-take. He flipped his finger across the screen and showed Bob the next two pictures of her body, featuring most of her body, including her boobs, bare abs, and her legs to the knee.
“Whoa! She looks incredible! How could you not like THAT?”
“That’s just it, Bob. She told me up front what she did, and we still enjoyed our time at the bar. When she asked me out, I thought it was for one of her client dates. No, she said she thought I was cute and wanted a normal date.”
“You? Cute? Was she wearing thick glasses? Is she as blind as a bat?” Bob snickered. Lennie smiled.
“Exactly. What could she see in me? We had a couple of dates, and on our second one, between a dancing lesson and dinner, we stopped at her place so she could grab something, and I went in. I thought she was going to change her outfit, but instead she came out in the raw. Completely nude. And we had some amazing sex. Possibly the best of my life. We never made it for dinner.”
“Sounds good so far, my friend.”
“And then, as I was leaving her place, she told me she was going to be out of town for a few days. We both knew what that meant, and it was hard enough for me to think about that. However, I expected her back Thursday night or Friday, at the latest. Here it is now Sunday evening, and still no contact, no calls, no texts, nothing.”
“Ahhh,” Bob said nothing, but nodded a few times. “I see your dilemma. You are falling for her, and since she told you up front what she did for a living, you are a dick if you mention you want her to stop and be with you exclusively. Yes, I see your problem. If you knew she was a call girl, Lennie, why did you continue to contact her?”
He just looked at the beer taps in front of him, with a hazy look in his eyes. Bob’s question was indeed the right one.
A men’s over-forty soccer team that finished their match arrived, sitting at four tables on the side as they did every Sunday evening during the summer. Always rowdy but never out of control or intimidating to other customers, their bill was usually equal to the rest of the evening’s sales. And they were good guys, too. Bob looked at Lennie and said, “Think about that while I serve those guys. I’ll be back soon, and you’re going to answer that.”
Bob was right, how she treated me and what she thought about me was the important thing, and I’m fucking everything up, Lennie sulked.
When Bob returned and stared at him, he responded from his heart. “She makes me feel special, like I’ve never felt before. And she is so kind and fun to be with. She has this way of being engaging, no matter what she says. Even though we have only known each other for a few weeks, she makes me feel like I’ve known her for my entire life. It’s like we are together on our own plane of consciousness. I’ve never experienced anything like it.”
Then it hit him. What he didn’t like was having to share all the time. Share the most intimate moments between lovers, except hers were with strangers who paid for her.
“Hmmm,” Bob responded. “Yeah, that’s love, Lennie. The Thunderbolt has hit you, and you’ve got it bad.” Bob had been watching old movies and had just finished watching the original “Godfather”. In it, there was a scene where a young Al Pacino, previously not involved with the family business, had murdered mobsters in New York and hid in Italy with old family relatives. One day, as he was walking across the fields, he spotted a young, beautiful local woman passing by. He was stunned at her beauty. The bodyguards with him said, “You’ve been hit by the Thunderbolt.” Lennie immediately recognized the movie reference and nodded. Robert nailed it.
The delicious cold beer was already nearly empty. Lennie pointed at his mug, and Bob pulled another glass from the under-counter refrigerator unit and poured him a fresh one. “You know, I’ve been married to my only girl for 19 years now. Now, if you listen to my relationship advice, you are stupid. But what has kept Isabella and me together is being able to talk about anything. I hate to sound like one of those women’s daytime TV shows, but open communication is the only way you’ll get through this.”
Lennie stayed until closing time, which was midnight on Sundays. He had five beers and a large burger, leaving two Benjamins on the bar. “SENOR! THAT’S TOO MUCH!” Lennie waved at him as he pushed the door open to depart and make the 20-minute walk home. “Bob, your advice is worth twice as much. Thank you, my friend, for being there.”
Lennie passed through the doors onto the sidewalk and started his mile walk home. After a couple of blocks or so, a shiny new metallic white Porsche 911 Carrera S Cabriolet convertible with the top up slowed next to him, matching his walking speed. The passenger window came down, and a familiar voice yelled, “There you are, I’ve been looking all over for you!”
“Lori? Is that you?”
“YES, it’s ME, Lennie!” she shouted. Hop in and let me give you a ride.’
“No, Lori, I’m just going to walk home, it isn’t far. Thanks anyway.”
“Lennie, get in my car now! “ It sounded more like an order than an ask. “I need to be with you tonight!”
“Why, Lori?”
“Just get in, and I can explain.” Her voice softened to a feminine request. “Please, Lennie, hop in.”
Lennie didn’t want to be with anyone and figured the easiest way to get rid of her was to comply with her wish. He opened the passenger door and hopped into the vehicle, which smelled of leather and new car. It was nice. Really nice. He didn’t know it, but he was the first person to sit in the passenger seat.
“Nice car, Lori. Now explain.”
“Thanks, Lennie, I just got it last week. Tell me where to go.”
He directed her to turn left at the intersection, where she drove for about a mile until they turned into a long driveway with an iron gate. The car stopped at the keypad. Lennie rolled down his window, typed in the code, and the gate opened. Lori pulled up to the right side of the circular driveway of the 9,500 sq ft., recently built three-story home. Following Lennie’s direction, pointing to the pavement going up the hill to the right, she followed the driveway up the hilly, large lot, around the side, and up to the front door on the middle-level lot that had room for four cars, turning off the engine. It was built on a property of just over one acre. The driveway led to the side of the house, which stopped in front of the main doors on the second story. All three floors had expansive views of Puget Sound. As it was built on a hilly area, there were no close neighbors and good privacy.
“Nice place, Lennie,” she said with admiration, as she stared at the house. He touched the keypad a few times, and the door opened. They walked inside.
“Okay, Lori, now explain why you were trying to find me. You don’t even live down here in this part of the county.”
The tall blonde with soft, long hair and a rocking body stared at the older man, paused for a few seconds, until she told him of her plans.
“Lennie, I’m going to stay with you tonight. All through the night. Cindy can’t be here, and she doesn’t want you to be alone. She called me earlier this afternoon. She feels bad that she has not been around and asked me to keep you company.”
Lennie shook his head with a hurt expression on his face. “Why would you do that, Lori? That makes no sense. And if it is so important to Cindy, why didn’t she call me?”
Lori paused for a moment, then remembered Cindy told her to be honest about their backgrounds.
“She’s out of the country with her best clients, and they wanted her to extend her stay. She felt bad that she couldn’t be with you this weekend and didn’t want you to be alone. I really can’t tell you any more details about her, you’ll have to ask her yourself. So I’m your bed-warming pinch-hitter, so to speak.” She proffered a half-smile as she said it.
“Clients? As in plural? Geezuz, Lori.”
“It’s not what you think, Lennie. I can’t tell you any more than that. You have to hear the details from her. Now let’s go sit down and talk.”
“You don’t have to do that, Lori.” He was speaking from the heart, and Lori, an expert in reading men, detected the disappointment in Lennie’s eyes and voice. This isn’t good, she thought. She had to turn his attitude around for her best friend, Cindy. Cindy had done so much for her over the years, and she couldn’t let her best friend down now. Making a quick decision, she figured that honesty was her best option. She took charge and also took a big risk.
“Lennie, you have to let me be with you. I owe it to Cindy. She’s crazy for you, you realize that, don’t you? Please, let me help you feel better, just for tonight.” She tried to cozy up to him and kiss him, but Lennie just stared at her. She sensed his doubts and pulled back, looking for a place to sit down.
The two walked into Lennie’s living room on the main floor with the expansive view of Puget Sound. A full moon glistened light across the Sound, revealing a night shadow of the magnificent view and Maury and Vashon islands on the far shore. She pulled him onto the large couch that looked out to the floor-to-ceiling windows. She dropped to her knees, and in seconds, Lennie’s pants were pulled down to his ankles. Pushing him down onto the large sectional, she furiously pulled off his shoes and socks before completely removing his pants and underwear. The look in her eyes changed from compassionate to dark and intense. She mimicked his smoldering negativity.
“You’re pissed at Cindy, aren’t you?” Lennie’s head shook up and down. She was sucking and jacking his cock with vigor. The look on his face was one of sadness and simmering anger. She pulled off his cock and reached up to him. Lori hugged him and kissed him straight on the mouth, her tongue probing between his lips. She pulled off and stared into his face, just inches away. Her attitude was angry.
“You’re mad at her, Lennie. Don’t hold it in. You hate what Cindy is doing, don’t you!”
He nodded again, the emotions starting to unravel what little cool he had.
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.