Lennie and Samantha Ch. 04

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Older man and an expensive escort accidently meet at a bar.
14.4k words
4.76
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8

Part 4 of the 4 part series

Updated 06/23/2024
Created 06/09/2024
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Please read the earlier chapters first or this won't make much sense.

NOTE: Chapter 3 was mis-labeled and is simply called "Lennie and Samantha" I forgot to add the Ch 3 heading. I will request the website to fix it, but be aware of the mistake.

Read that chapter first and then read this one, chapter 4. Sorry for the confusion.

Thanks for the support and I welcome your comments.

****

Two days later Samantha returned to Seattle. Now Cindy again, she had become distraught by Lennie's disappearance. She called Lori but her friend had no additional news or insights. After leaving message after message and getting no response from Lennie, she became cold and emotionally vacant. It seemed just like it was a decade ago when she fell completely for a guy who later deserted her after learning of her background. She kept Samantha's phone on. Two days after she returned, one of her best clients, James, called her to meet the next day.

It was 11 am on a weekday morning. The new black Mercedes AMG sedan pulled into the reserved parking space of the high-end condo parking lot. A large, well built man wearing a black power business suit, red tie, and four-figure handcrafted English leather shoes stepped out. A half-hour ago, he was in his corner office of the half-billion dollar manufacturing company in which he owned a majority interest. He walked up to the door and pressed the button for 204. The door buzzed and the lock opened. The man of stature opened it and walked across the foyer to the elevator. He entered and then appeared, walking the second floor and down the hall. As he got within two steps of knocking, the door opened and a beautiful brunette woman with shining blue eyes but no corresponding smile appeared. She was dressed like a housewife or mother of a teenager with khaki Capri pants, a dark blue blouse, neutral sandals and very little makeup. Her long brown hair was pulled back into a ponytail. She shut the door behind him. There was no kissing; instead she gave him a hug like a relative would.

"Everything is set up and ready," the brunette with shining blue eyes and still no smile said. "How long do you want?"

"Give me 30 minutes, ok?"

The beautiful woman nodded. He started walking down the hall, knowing exactly where his destination was. He had been there many times before.

In exactly a half-hour, there was a loud repeated knock on the closed bedroom door. "Jimmy! Oh Jimmy!, I've got your lunch today and it's your favorite! PB and J, with strawberry preserves, just the way you like!", she announced. After a couple of seconds and a half-dozen knocks, the woman opened the bedroom door, carrying a tray with a plate containing a peanut butter and strawberry jam sandwich on white bread, some potato chips, and a glass of milk.

Jimmy froze. He was sitting at an expensive, modern desk, watching a large computer monitor that had a video of a famous porn star getting gangbanged by three black men with very large cocks. Two of them were plunging deep in her ass, while she wildly sucked on the third.

"Jimmy! What are you doing? You're watching that nasty porn stuff on the internet, aren't you?"

The expensive suit and English leather shoes were gone, laying in a pile on the chair in the corner. Instead, the man was wearing pajamas. Pajamas that only a teen should wear. His bottoms were down at his ankles and he was furiously masturbating his hard, longish cock to the sex scene. On the large expensive monitor, there were 3 other windows open with similar sex scenes. In fact, the woman had set it all up and had his pajamas on the bed waiting for him before he walked in the door.

"Jimmy, you're masturbating again to that dirty porn stuff, aren't you?" She gasped, the woman's tone now more disappointing instead of accusatory. She shook her head in disgust.

"Jimmy, what has your aunt Samantha told you about......this!," waving her arm at the computer screen and his groin, hand around his hard cock while fondling his balls with the other. She walked over to the computer and with the mouse clicked the next tab. "What's this?", she shouted forcefully. "And this?", clicking the next window, "And this? You'd better start talking, mister!"

The man acting like a flustered teen with out of control urges stuttered back, "a five cock nigger gangbang, an airtight nigger cock gangbang, and a nigger breeding white girl session," not missing a beat in word or action.

"What did you say, nigger? No nephew of mine talks that way around here, young man! Get over here and lay down over my lap! Before you do, hand me that cane switch over there!"

Jimmy got up and started pulling up his pajama bottoms.

"Leave those PJ's off and come over here, now! "

He laid down over her lap as she sat on the pre-positioned bedroom chair, his 240 pound, strong masculine frame and bare ass over her feminine lap of her 135 pound body. Her hands held his face as she twisted it to hers. "You will never use that word again, mister. Where did you hear it, anyway?"

"From the girls that were being fucked, aunt Sammie," he whimpered.

"You...[whack]...never....[whack]....use...[whack].....that..... [whack]..... word...... [whack] ...... again!.....[whack]. Do you hear me, young man?"

The cane switch was leaving welts on his naked ass. He was beginning to yelp and cry after the cane made contact. Twenty lashes later, she stopped. Real tears were pouring from his cheeks. The welts were as real as the tears.

"You said that it's nasty and wrong, aunt Sammie", the man responded with regret. "I know that it's wrong, aunt Sammie. But I get feeling so weird. There is this urge that I can't control. I have to start playing with myself. I'm sorry!"

"You know I hate to do that, baby," her voice suddenly an octave lower and quieter, now soothing and calm as she gingerly touched his backside.

"You've got to stop using words like that. Those are hurtful words. Now come here and let aunt Samantha make it better, baby," she cooed. Samantha pulled out a tube of expensive skin conditioner and slowly brushed and rubbed the lotion on Jimmy's whipped ass with her soft hands.

"Baby, after your dad left and since your mom is always traveling and gone on business to support you, she asked me to take care of you. I know I said it's wrong, but I'm talking about that nasty porn stuff those slutty women do with those men and their giant cocks. I'm not talking about you feeling good, baby. I know you're only 15 and boys your age have, you know, needs."

She pulled herself around to be beside him, her body next to his. Their eyes met and wouldn't release their shared stare. The boy/man was starting to breathe heavily. She was locked into his emotions like she was reading his mind. He was having trouble recognizing if this was real or the fantasy it was.

"Baby, all men have.....needs", the word "needs" slowly drawling from her lips. Sam was slowly moving beside him with her slinky body, rubbing her massive tits against his arm while her hands roamed over his bare abs and chest. "Aunt Sammie wants to help you take care of those needs naturally, baby. You should always get a girl to help you take care of your needs, baby, because that's what girls are for, not watching that nasty internet stuff and jacking your cock by yourself. Here baby, stand up for me and lets pull that pajama top off and sit on the bed, ok baby?"

Samantha immediately changed her body language and became a sultry, sensuous woman rubbing every one of her feminine curves to his body while breathing into his ear and lightly licking his neck.

"OK aunt Sammie, thanks, that's so nice. I'm just so hard right now, you know? Look at me. I'm so hard!" He said it proudly like he won a contest of some kind.

"Yes you are, baby", she purred. The aunt reached calmly toward him and clasped his bulging cock, leading him to the bed. She snuggled up to him, heavily breathing on his neck and in his ear, whispering "It's OK, baby, let me help you take care of this hard on you have. Don't be embarrassed, sweetie, your body is telling you that it has needs right now and the best way, by far, is for a woman to help you take care of it. It's terrible if you don't get help and have to instead take care of them yourself. Let aunt Samantha help you, baby", her voice purring in his ear.

They sat down together on the large bed with expensive Egyptian cotton sheets, the thick down comforter and blanket pulled away to expose them.

"Come here, baby. Let aunt Sammie help you. I want to help you baby. These needs you have are a man's needs. Don't feel embarrassed, honey, you are becoming a man. I want to help you. Now do what I say and don't talk back, OK? Do you trust your aunt Sammie to show you how to take care of those needs?"

"Uh huh", he gulped.

She never took her hand off his hard cock as she slowly stroked it, and after they sat on the bed she snuggled into his side, her breath warm and moist on his neck. Her tongue was softly licking his ear while she slowly stoked his hard cock. "Is that OK, baby? Do you like that, baby?"

"Uh huh," he mumbled again. She turned his face to hers and gave him a long, passionate kiss.

"Now, you're ready. Let me get ready baby. Will you help me out of this blouse?" Her hands had already unbuttoned it and she held one arm out for him to pull on as her arm fell free. He repeated the move with the other arm. Her large firm breasts were being held by an expensive black lace bra. She unhooked it from the back and let it fall, revealing her large gorgeous mounds of sweet flesh.

"Kiss them, baby. Feel them. Lick my hard nipples, sweetie. This is what a woman is, sweetie. Isn't this better than that nasty internet and your hand? Take me, baby."

The imaginary boy immediately went into a frenzy and grabbed the firm and soft mammaries, licking and kissing out of control.

"Easy baby, slow down, they're all yours, baby. Take your time and enjoy them. Oh, look, you're cock is so hard!", as if she was proudly telling him he had been victorious. He started licking and kissing the beautiful body of hers, like a kid who had never been in such a heavenly place.

"Now baby, let me help you become a man," she whispered in his ear as she continued to stroke his heavy cock. He was breathing harder and harder. She bent down and slowly started to lick the shaft, up to roll her tongue over the head, and then plunged down on it, her mouth accepting it until her nose was buried in his pubic hair.

At first, she sucked slowly so he could feel her mouth and throat surround his large cock. As she held it down, her tongue and throat massaged his turgid cock without moving her head. She stayed there for over two minutes, her nostrils flaring and seeking fresh oxygen for her needs. Eventually, the man-boy was starting to shake. She sensed it and pulled off, breathly gasping "Cum for me, Jimmy. Cum baby!" and shoved the cock back down her throat.

He strained every muscle in his body, only feeling the raw heat emerging from his hardness. The cum exploded in her mouth, blasting down her throat. She moaned as the thick goo shot again and again. The man-boy was shaking and grunting over and over until his actions finally subsided.

She pulled off of him, sat up, and swallowed. "Was that okay, Jimmy? Did your aunt Samantha help you, dearie? You needed that, didn't you?"

"Oh, yes aunt Sammie! That was so good! Thank you, thank you!" He was like a teenager who got the Christmas present that he had asked for but never expected to receive.

"OK baby, now eat your lunch here, while you recover. You're aunt Samantha has another idea before you go, but eat your lunch first."

The man-boy ate his PB and J quickly as he could, but the peanut butter kept sticking to the roof of his mouth. Aunt Samantha sat beside him, naked and her legs spread open. Her hand held his soft cock, but she didn't move until all the lunch was finished and the glass of milk empty.

"That's my Jimmy. Good boy, you ate all your lunch." Her hand started moving up and down again as her grip started to firm up. She led his hand to between her upper thighs. "Now, slowly move your finger between my legs. Easy, slowly. That's it, baby. Slip a couple of fingers in that wet spot, but do it slowly."

Jimmy followed her instructions and his fingers went in and out of her wet pussy. "Pull your fingers out and smell them, honey. Do you like that smell, that taste?"

"Oh, yes aunt Sammie! It's so good! It's you! It's so good!"

"Yes, it is me, baby." Then she moved and laid down on the bed. "Get on top of me, honey. Show me what a man is supposed to do to his woman."

Jimmy, hard as nails by now, mounted her and started pushing in and out of her wet cavern, slowly at first and then with wild abandon.

"Oh that's it, Jimmy! Harder, harder. Yes Jimmy, yes! Oh Jimmmyyy!"

No longer able to hold back, Jimmy blasted his bare hard cock into her with ribbons of white, coating the walls of her wet, receptive womb. Jimmy was an excellent lay and made her cum hard. After a long while, he stopped and collapsed on top of her. The heavy weight was supported by the woman, experienced in having men lay on her after they exploded.

"That's it, baby, that's it," as she rubbed and patted his shoulders and lightly stroked her fingernails up and down his back. "You did good, honey. Do you feel better now, sweetie? Did aunt Samantha help you take care of your needs?"

"Oh yes, aunt Sammie, thanks! That was so good! And I'm sorry for watching porn again, I promise I'll stop as long as you help me with my needs. You make everything feel so good!"

She led the man into the large deluxe shower and slowly washed him off, taking a long time to wash his body saying nothing. The tenseness in his shoulders fell away with her soft touch as she massaged him, ignoring his still sore ass cheeks. They slowly kissed but he couldn't get hard again.

The encounter was over. After gathering and dressing in his expensive suit and English leather shoes, he leaned into her, giving her a warm, mature kiss. She hugged him back as their tongues moved together.

"Thanks, Sam. That was amazing as usual. There is nobody as good as you. I don't know how you do it. Today we weren't playing like I was fifteen. I swear, I felt like I actually was fifteen. I was really back in my bedroom feeling the embarrassment of my aunt finding me jacking off. Except she of course never fucked me, she just jacked me off while keeping her clothes on. How you made this fantasy so real is a testament to how damned good you are at your job. It was something I will never forget, no matter how old I get. Here's your gift and there's something extra for you."

He handed her a fat, white envelope. The handcrafted English leather shoes clacked on the tile entry as the door shut behind him. She looked at the clock on the kitchen wall, he had been there for three hours and change.

As the door closed, she opened the envelope and counted one hundred and twenty hundred dollar bills. She smiled, and then opened up her iPad and logged in the details of the last three hours. His fantasies were once again satisfied. Yes, Jimmy understood the special quality of service she knew how to provide. She would make sure that James Roland Peterson, a well-known regional business leader as well as being her Jimmy, will always be accommodated whenever he wants.

After she typed in the details of the encounter, she placed the iPad on her desk and tossed the envelope in the top right drawer. Then she checked her phone and realized the absence of any communication from Lennie since she returned from her extended encounter. She sat down in the chair, still naked, and cried uncontrollably.

Her emotions were frayed but the demand for her beauty was at an all-time high. A few hours later, she got a phone call and in three hours was on the private plane of one of her clients, fetching her to meet him for a 36 hour encounter in Las Vegas. Unconsciously she was trying to forget Lennie by doubling down on her work. By constantly screwing her clients she was trying her best to get past her relationship failure with the older man for which she had finally dropped her barriers and got burned once again.

****

His cell phone rang with an unusual tone. Lennie wondered who he had given that ring to, and couldn't remember who it was. Awakened from a sound sleep but still in the depths of his beer-induced state after a week of drinking and boating, the voice reminded him immediately whom it was.

"Lennie, we need to meet. Now". A familiar voice spoke in a demanding tone.

He looked at the clock. "2:55 am" it silently shouted back at him.

"Huh, what? Is that you, Lori?" he mumbled as he started coming out of his sleepy haze.

"Yes, Lennie. Look, I'm coming over and we need to talk. You need to listen to us before you try to break it off with her, got me?" The phone went dead before he had a chance to respond.

In just over a half hour, there was a buzz indicating a car at the gate. Lennie pushed the button and looked at the security camera display, noticing a large black new Chevy Suburban SUV. It was full of people. As it pulled into the circular drive and then to the right drive leading to the front door, six incredibly beautiful women stepped out. Leading the group was Lori but he didn't recognize the others. Lennie walked down the stairs to the second floor where the main door was, and opened the door just before the bell was touched.

"Lori? What's up? And who are these women?," the groggy man exclaimed. Lori looked as stunning as the night she gave herself to him, grabbing him with a close tight hug. Designer jeans that seemed painted on to align with every curve of her butt and thighs, a body-forming thin salmon-colored sweater outlining her large magnificent breasts, and black pumps with long heels pushed her perfectly shaped ass out even further. Her long blonde hair fell freely down to her shoulder blades.

Lennie tried to think of any other time he was saw such a large group of such beautiful women. Was his hazy mind doing tricks on him? He scanned the others walking into his home and was stunned at their collective beauty. 'I must be dreaming', he muttered under his breath.

His stare didn't last long at one woman because the next one following her was just as amazingly gorgeous. They were dressed differently, some informally and a few like they dressed for a date at the hottest night club in the city. His groggy mind was waking up to admire the stupendous beauty sitting around his living room.

His eyes locked on what was a Spanish-heritage looking Latina woman, perhaps 30, with deep brown eyes and exceptionally soft cocoa butter brown skin. He immediately associated her beauty with that of Yanet Garcia, the Mexican TV weather girl that was now a big Instagram model, except this woman was maybe four inches taller, thick coal-black long hair instead of Yanet's brown locks and with thicker body and curl, and thighs and an ass that was curvy but was certainly less Kim Kardashian-ish and proportioned more classically. Her look was dynamically sexy. Without a doubt her face was more naturally beautiful and the look in her doe-brown eyes were sexier. "Wow, she's effing beautiful!", was his immediate reaction. Did he think that or blurt it out loud?

She was fit and feminine, sort of a "runner's body" except her breasts were much larger and her hips had curves that rounded back to her tight bubble butt. Long black hair was done up in an exotic bun but also locks that framed her model-like face fell in sexy long curls. She was wearing an expensive, clingy satin-white evening gown with a slit up her right hip above her waist that showed she obviously wasn't wearing panties. It was held up by two thin spaghetti straps that plunged down to a poor attempt to cover her luscious large firm breasts. An expensive diamond necklace was the perfect contrast laying over her enticing light brown skin, matched by a pair of large stud diamond earrings and a diamond tennis bracelet on her left wrist. The contrast in color from her delicious glowing skin, long thick black hair, and the slinky white gown was astounding. Gazing at her large, firm breasts with protruding nipples not held back by a bra, Lennie's jaw fell open as his eyes froze staring at her.