Changing Times - Cover

Changing Times

Copyright© 2026 by dawg997

Chapter 1: The New Normal

Erotica Sex Story: Chapter 1: The New Normal - 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  

The town car pulled into the parking lot of Boeing Field and drove to the hangar, where, outside on the tarmac, the big new Boeing 737 Max Business Jet had been parked for a few minutes, long enough for the CFM International LEAP-1B twin engines, each able to produce 29,000 pounds of thrust, to shut down.

Only nine days ago, this very jet was delivered to its new owner, Samuel Jackson Haggarty, who now only went by his middle name, in Palm Beach, Florida, far from the Boeing Renton plant where it was assembled, just eleven miles by road but only seven as the crow flies. After leaving Florida, with stops in Washington DC, and New York City to pick up his important and powerful guests, it touched down for the first time at Boeing Field, the public airport that private planes utilized to fly into Seattle.

The smartly and expensively dressed brunette, blue-eyed woman peered from the limousine, waiting for the group to come into view. There they are, she thought. She saw the line of eight executives that had just walked down from the jetway stairs and were heading to the terminal to be picked up in one of the numerous limousines waiting for the six men and two women.

Getting out of the limo, she started walking the three hundred-plus yards to the jet stairway, passing the executives on the tarmac. Many of the men couldn’t help but notice the beautiful brunette in her tailored two-piece business suit, consisting of a sexy skirt and a tight blouse that fit her amazing body like a soft glove. Her delightful look was a feminine wonder. Most were close enough to see her beautiful face showing off her high cheekbones, her twinkling blue eyes, and her million-dollar smile that felt like it belonged in a toothpaste commercial.

She was the entire package. One sweep with your eyes told you everything you had to know. Flowing, long brunette hair with just a touch of curl until it ended between her delicate shoulders and her massive breasts. The firm 38Ds stood proudly in her blouse, her cleavage boldly showing for all to see. The look swept down her small waist, tight abs, and stomach, flowing downward to the proportional hips and sexy thighs. The look was dazzling and suited to a business environment. However, it still made everyone look twice at her delightfully feminine shoulders.

But even more than her exceptional beauty was the way she carried herself as if she belonged there and actually owned the place. The level of sophistication she exuded was off the charts. One man, staring at her butt after she passed him and not paying attention, actually ran into the man in front of him.

Seeing the collision from the corner of her eye, she giggled but kept walking until she reached the bottom of the stairway. A large man in his early fifties, muscular, trim, and with a full head of partially graying hair, stepped out and looked down, seeing her for the first time in a long time.

“Samantha!” He bellowed loudly. Some of the departing men looked around to catch where the voice came from.

“Jackson!” Her response was one of anticipation, as she was looking forward to seeing him again. “OMG, Jackson, you got a new jet!” she shouted in glee. After one heard this beautiful woman speak, one wanted more of her attention. She was that incredible, that hot, that classy.

All of the departed passengers were watching the woman interact with their flying host. Who was this woman who had obviously caught the eye of one of the most eligible bachelors on the East Coast?

“Yes, baby! Come on up and check it out! It’s the new Boeing Business Jet. I just took delivery last week, and it still has that new plane smell! Come on up, baby. Check out my new ride!”

Smiling her million-dollar smile and moving her head just enough to flip her hair for maximum effect, she proceeded up the stairs.

As she stepped up the stairway, her sexy hips and bubble butt swayed back and forth, easier to see for all as she ascended upward. Some of the men who had deplaned stared, one commenting to the fellow flier next to him, “Oh my fucking god, look at that ass! Look at that thing shimmy and shake!”

“It’s like a perfectly running machine,” another man blurted out.

The late 40s woman next to him, another fellow flier who hopped a ride from the East Coast on the jet as his guest and also a well-known power lesbian, simply said, “Geezuz, what I would do to eat that!” The men laughed but couldn’t tear their eyes away from the beautiful woman ascending the stairs to meet their host, who had flown them to Seattle for business.

Samantha smiled and walked up the jet stairs and was greeted with a tight hug and a long, deep kiss. They hadn’t touched each other in three months—although they had communicated regularly via the web or FaceTime on iPhone or iPad. This meeting was their first physical touch, and it was too much for him.

“Get in here! Now!” He pulled her in by her hand, and after reaching to unzip her tight skirt and letting it fall to the floor, spun her around to land her thong-split butt cheeks on the closest stylish leather couch.

“Ohh!” Samantha fell on her back, and Jackson Haggarty leaped on top of her, resuming their passionate kissing. She ground her naked, smooth ass into the plush, luxurious leather, with a supple, velvety texture that molded to her body. It felt sexy, like being the first skier to make the morning run in fresh powder snow. After intense kissing and fondling, Samantha broke to ask a question.

“Aren’t we supposed to be going to a business meeting?”

“They can wait an hour. Come on, let’s break into the large bedroom,” he commanded as he pulled her down the open area of the jet. This jet was a Boeing Business 737 business jet which had a maximum capacity of 28 passengers. It had the same airframe and power as the 737-800, which seated 162 passengers in the normal, two-class configuration. Inside, instead of row after row of seats, everything was completely different.

All 20 seats were domestic first-class and grouped in small clusters, except for the four seats on the first leather couch and the four international first-class combination lay-down seat/sleep pods, which gave the passenger total privacy and darkness when the sliding door was closed. On the longest flights, a pilot would sometimes use one to get some needed shut-eye. They were the same seats as those on an international first-class section of a 777, Boeing’s largest international jet. In the rear, besides one of two restrooms, there was a private sleeping room with a built-in queen-sized bed and a large, full-sized shower (for a commercial jet).

“Jackson, this plane is incredible!” She was in actual awe as she walked down the aisle. He grabbed her, fondling her magnificent breasts and kissing her as he walked her closer to the bedroom. One hand fell to her tight, feminine ass cheek, and he sighed when he palmed it.

“Ohh, Jackson, we have a bed to break in! Not to mention these leather couches and,” she paused as she glanced at the 4 first-class sleep pods/seats, “as well as four more times in those,” pointing to the sleep pods. “They have that same leather, like the one that felt great on my ass when you tossed me down,” she purred.

They made it to the bedroom door, and he flipped the recessed knob, flinging open the door and giving her one last pull. They frantically grappled at their clothes and then each other’s, piece after piece flying to the floor. He hurriedly tried to pull his socks off while standing, falling on top of her, and both falling on the bed. She shrieked and laughed, while he was smiling and hornier than hell. He needed to get inside of this woman, finger her, taste her, and fuck her. Which hole first didn’t matter—his mouth would be on another in minutes.

She laughed and giggled, completely exposed and accessible to him. He flipped her over and pushed his face into her holes while she wolfed down his nine-and-a-half inches. With zero gag reflex, she could barely but completely swallow the manhood down her throat. She knew it because she had made an evening out of it one time, years ago: measuring it and then worshiping it for four hours. It played not only to his sexual frenzy but also to his giant ego. He had thought she truly loved him; she knew how good of a GFE whore she was. One of the world’s best. The income statement of Samantha’s Escort Service proved that.

After all, how many multi-billionaires would come to her in Seattle because she didn’t want to travel to New York, Europe, or Asia to be with him during business events? They had feelings for each other, but also complications. Last year, she had turned down his marriage proposal again, for the fourth time since they had first met over 18 years ago.

“Fuck me, you goddamned hunk of a man, pound my pussy like the whore I am,” Samantha cried out. “My pussy, Sin, wants it, Jackson! Sin needs your cock. Now! Fuck me! Fuck my pussy! She’s wet for you, baby. She’s all yours. Now fuck her! Slam that big hog into me! Fuck me, Jackson!”

“Spread those legs wide, baby, I’m gonna pound Sin into submission!” he roared. “She is getting flooded with my cum!”

An hour later, as they lay naked in each other’s arms, Sin still leaking his spunk and sated once again, he broke the silence. “God, I love you, Samantha. No matter how hard I try, I can’t get you out of my mind. You’re embedded in my mind, my heart. Goddammit, you are a fucking whore, fucking hundreds of men every year. And I’m a fucking billionaire, able to afford any woman on the planet. Yet, after all these years of knowing you, and after divorcing three women who I thought were for me, even if they gave me five kids, the years have proven that you are my soulmate. My soulmate is a fucking whore, and damn it, I worship the ground you walk on.”

“Now stop that, Jackson. You love Maria as much as you do me.”

“Maria is gorgeous. She’s stunningly beautiful. She’s an absolute ten. She’s an incredible fuck. And she is so fun to be with—sometimes she’s like a teenager in how she understands the world. Possibly the most beautiful woman in the world, if truth be known. But then again, physically, so are you. That Eastern European classic look—you have the body of a Greek goddess and your gorgeous face,” he paused in mid-sentence, reaching forward to lovingly cup her cheek in his palm. Looking at her face took his breath away.

“Both of you are tens. And your colleagues at Samantha’s Escort Service, or sisters, as you call them, are at least nine-point-eight or nine-point-nine. I’ve been with every one of them at least a dozen times—and Maria, well, I’ve fucked her a hundred times or more. But you, Samantha, are as beautiful as her—only you appear to be European American while she is a Spanish-Mexican beauty. No, the physical beauty of the two of you can’t be denied. I don’t think it can be compared either. It is impossible to compare perfection. Both of you are insanely attractive.”

She held him tight, giving him a long, wet kiss. After a passionate embrace, he pulled back, needing to say more. “But you, you are my lover and muse; you have something special that gets into my soul. You read my mind before I even created the thought. You know what I like and what I don’t, even if I’ve never been exposed to it. You can actually read my mind and my attitude before I say anything, and know what to do and what to say. I admit it, Samantha, you are a woman like no other. You’re special to me, and I just know it.”

She knew he wanted a response, a commitment from her. Instead, she quietly but firmly mentioned, “We have to get dressed, Jackson. You have a board meeting to attend.”

“Skylar knows what to do. After all, she is my personal assistant and understood I would be with you for a while. She passed you while she got off the plane to check us in and plan for tomorrow’s first board meeting.”

“Which company’s board meeting?” She knew his every move, having coordinated with Skylar before his flight. She didn’t know which meeting was when.

“It’s Starbucks on Tuesday and Amazon on Wednesday, and then we’re out of here for nine days. I am soooo looking forward to having you on the boat.” His “boat” was a 113-meter, five-story superyacht, currently in the Mediterranean. It was modern and stylish and was featured in numerous magazines and videos as one of the finest yachts in the world, as well as in the top 30 in size.

“Oh yeah, baby, sun in the Med on your boat. I’m so looking forward to that.”

“Baby, I’m looking forward to it, too. Look, I’ll take care of some important clients while you have your meetings and won’t be around during the daytime. But I’ll be around at night. Are you staying at the Four Seasons again?”

He didn’t like hearing that Samantha would be busy when she was supposed to be exclusive to him. Although he realized that since he would be busy anyway, it really didn’t alter his plans. One of the many things he liked about Samantha was that she was always truthful with him.

“No,” Jackson said, “I’m staying at the Fairmont Olympic. I’m on a nostalgia kick and have been staying at classic local, one-of-a-kind properties when I visit various cities. I hadn’t been to the Fairmont Olympic in years, before it changed from the old Olympic Four Seasons and the Four Seasons moved into their current, nearly new building. I’m usually a Four Seasons guy. They have that bar down there, Goldfinch’s, and I like the bartender. His name is Greg. He’s been there for years, one of the best I’ve seen.”

“Greg?” I know Greg! Yes, he’s one of a kind. I think that guy has Google hooked up directly to his brain. That guy knows everything.”

“You know Greg? Wow, small world.”

What Jackson didn’t know was that Greg was the man who essentially introduced her to Lennie, her first and only boyfriend, the night they first met, just over five months ago. Jackson had picked her up for one of their quick, two-hour encounters as he was passing through town from New York to Tokyo. While he didn’t know who Jackson was, Lennie had witnessed her when she first arrived, and when Jackson showed up to pick her up for their date upstairs in his room. When they were done and he left, Samantha came back down to Greg’s bar. Greg had casually mentioned she would probably be most comfortable sitting down at the end of the bar, “by that old gray-haired guy.” Just meeting Greg hours before and enjoying his banter immensely, she followed his suggestion.

That is how Lennie met Samantha. The moment of nostalgia over, she refocused on her “client du jour”.

It surprised Sam that he went back to the Fairmont, which was the original Four Seasons until the new one was built. Jackson hated antiquated things, like used planes or staying at older properties, even if they were once the top place in the city and still an example of amazing architecture. She’d spent many an evening in his bed at both prime properties in the last 16 years. She was quite familiar with the layout of the Fairmont Olympic, even though Jackson had not bedded her there for many years, until this visit.

Jackson continued, “But instead of the Four Seasons, this time it’s the Fairmont Olympic. Their service is great, and all those ornamented decorations on the walls were one of a kind, as if they were from a different era. I’ll need you for dinner both nights, though it won’t be a problem, will it?

Sam nodded her head. “I was planning on it. I’ll bring an overnight bag.”

“You are in such demand, Samantha. I get it, but you also know I don’t like to share.”

She smiled at him. “I know, Jackson,” holding her hand to his cheek as their eyes locked, “it’s tough, but this is the way it has to be. Believe me, you aren’t the only one who feels that way.” Her voice was sincere. She smiled, which immediately changed the mood. “We can eat and smash on the flight to Ibiza. You know that I love that Spanish island in the middle of nowhere, especially in September. The weather is perfect.” Her voice held an honest sincerity.

“Yeah, I know you love Spain, baby. I’m trying, you know.”

“Trying?”

“Yeah, you know,” he muttered as his voice cracked. It was difficult for him to be so honest, revealing his innermost emotions. As a multi-billionaire, he never had to show his feelings to any woman. At least that is what he thought when he was married. Perhaps that was why he divorced three times. “You told me the reason that you’ve turned down my proposals is because I don’t pay enough attention to you. I know how much you like being in Spain, so I had Captain Kirk move the yacht from Cannes to Ibiza. He is underway now.”

“That still cracks me up. The captain of your yacht is really named Kirk,” she laughed.

“Yeah,” he chuckled, “except his first name isn’t James, it’s Larry. However, I agree, it is funny. Did I mention that we have an engineer named Scott and a deckhand named McCoy? Someone joked that I should rename my yacht the Enterprise.” They both laughed.

“So Ibiza, Spain, then? Thanks, baby, you are so attentive to my needs.” She smiled her million-dollar smile again as she wrapped her arms around his neck and gave him a long, deep kiss as she ground her Ds into his chest.

“Jackson, go ahead and take the limo to your board meeting. Skylar and I will meet you at the Fairmont Olympic later, after your meeting is over. Do you want us both to go out on the town with you?” It was as if Samantha were making a list of events she would attend with him and asking so she could be completely prepared for every event.

“Naw, Skylar is going to hang out while you and I go to dinner and dancing. She will be staying on the plane tonight, preparing for the board meetings, so we can be alone.”

“She won’t be with us?” Samantha inquired. She had expected a threesome for a couple of days and was caught off guard by his comment. He walked forward to the built-in desk and pulled out files he knew he would need for the meeting. Skylar had assembled them all, and he took his time reviewing them one by one and then slid them into his briefcase.

Samantha followed him up to the front of the plane, where Skylar was sitting on one of the seats, reading her iPad.

Skylar had been with Jackson Haggarty for three years as his personal assistant. She was one of Samantha’s Escort Service’s housewife regulars until 4 years ago when she got divorced. Since only married women can work for the service for many reasons, and to eliminate headaches for Sam, Skylar lost her job working for SES. But Samantha always cared for people, especially for her girls, who worked for her.

High-end escorts—especially the intelligent ones with college degrees—were always in demand. Rich men want to have a dependable, smart, beautiful, and slutty assistant. In reality, these women were both easier to live with than a modern Western wife and also a hell of a lot cheaper when the inevitable divorce happens.

For Jackson Haggarty, the inevitable happened three times, the first one without a prenup. He didn’t make that mistake again, and he was proud of all five of his kids, now teens or college-age, but living with their mothers and communicating with them was limited. He always made sure they never went without anything.

Haggarty had enjoyed the company of Skylar ever since she began working at the escort service four and a half years ago, as well as all the other girls. She had saved over three million dollars and a wardrobe of expensive gifts, including clothing and accessories, nearly a third of them from Jackson. When Skylar had to leave SES due to her divorce, it was Samantha who recommended her to the multi-billionaire who controlled large corporations worth north of two trillion dollars and employed 135,000 employees. He was a powerful man who expected excellence. He was also impatient with everyone and everything except Samantha, that is. In addition to Skylar’s million-dollar-a-year salary, Samantha received half a million, as a commission, for recommending Skylar. It was no different than paying an executive recruiter to fill a senior corporate position. Skylar was unique, however, being a smart and driven business assistant, in addition to being a world-class sex toy at his calling.

Money for a multi-billionaire, especially for something important to him, was on a different level than for anyone else. It was chump change to him, especially for such sensuous beauty. Skylar, on the other hand, was quite loyal in exchange for her million-dollar annual first year salary.

“Hey Skylar, how are you doing? We haven’t talked with each other in months.”

Skylar paused for a few seconds before saying, “Okay, I guess.”

“Okay? Just okay? How is Jackson treating you? You’ve been working for him for almost three years now?” Something was off, and Sam was going to find out what it was.

“He can be really demanding, Sam. I’m glad you are coming with us when we go to New York and Ibiza. Fuck the shit out of him, okay? Maybe it will calm him down for me,” Skylar huffed, and wasn’t smiling like it was humorous.

She pulled Skylar into her and gave her a deep, passionate kiss. Skylar, caught off guard, returned it with a sensuous passion. The two gorgeous women broke apart and looked into each other’s eyes. It wasn’t the first time they had kissed; Skylar used to be one of the married escorts working for Samantha’s Escort Service for nearly three years, until her husband changed his mind and decided he could no longer be married to an expensive whore. For those three years, however, he never had a problem with the half million or more she netted every year and shared willingly with him.

“I will fuck the shit out of him, Sky, and we are going to double-team him a lot, too. Together, we will mellow him out.”

Both girls smiled, confident in their plan to please Jackson Haggarty.

Sam paused and looked at her younger associate, who provides professional pleasure only to rich and mostly powerful men, now exclusively to Jackson. “How long has it been since you had to leave SES? Has it been three years now?”

Skylar nodded. “Yeah, it will be three years next month. When I had to be let go from SES because I was getting divorced and the service only used married women, I had no idea what my next step in life would be. Going from a world-class escort to a billionaire’s Personal Assistant has been a crazy whirlwind, being Jackson’s personal assistant as well as his personal whore.”

“It dawned on me how fast time has gone by since you left,” Sam commented. Sam’s comment had triggered feelings in Skylar that she couldn’t hold back.

“When you first mentioned the opportunity to me, I never thought it would be anything like this. He has made me rich, over three million bucks in three years from salary and bonuses alone. I now make a full million a year as my base, and nearly that in bonuses. All the while traveling to the ends of the earth. I make all this money, and I have nothing to spend it on because he pays for everything else. I have not paid for a stitch of clothing in the entire time. He insists that my purchases be charged to the company card. Jackson makes sure I’m always dressed to the hilt. My background in finance has me working on his top projects with him, which I thoroughly enjoy. His yacht is incredible, and spending two or three months in Europe every year is wild. Look at my arms and chest,” she said, pulling down the front of her low-scooped dress to reveal her perfect skin. “No tan lines. My body has never been more bronze with months of tanning. Of course, I have you to thank, Sam. It’s just, well...” Her voice faltered.

Sam realized it immediately. “What’s wrong?”

“It’s been three years with him and six months more since my divorce. I give myself to him emotionally as well as physically, and he compliments me on how I keep his schedule, but he doesn’t love me.” She paused for a few moments and looked directly into Samantha’s eyes.

“He loves you.” There was no reaction from Samantha.

“He may love me, Skylar, but he can never have me exclusively. There are too many other things going on in my life for that to happen.”

Sam looked into Skylar’s eyes in silence. Her look was hungry—Skylar’s was submissive. They froze until Sam took charge.

Samantha grabbed the personal assistant and roughly kissed her open mouth. Sam, still naked from the sex with the billionaire, grabbed at Skylar’s clothes and pulled them off in a sexual frenzy. Her hands slid down the redhead’s body, finding a pussy to slide two fingers into Skylar’s pussy.

“Oh god! Oh god! Bang me, Sam! Oh god, your fingers, your fingers! Yes! Rub my clit, yeah, just like that!” Their mouths were sealed in a wet frenzy.

Jackson had returned and was watching, fondling the two naked beauties, expressing their sapphic desires. Samantha knew he would enjoy what he saw. He grabbed an arm of each beauty and pulled them to the back of the jet to the bedroom. Tossing them on the bed, he sat down by them, a hand on each naked body, an ass cheek, a boob, and a thigh. It was so hot that all three of them were sexually out of control. He mounted Samantha from behind and humped her like a horny dog. Sam’s face was between Skylar’s legs, licking her clit and fingering her hole as she responded like the passionate bisexual she was. Skylar, her dormant lesbian desires finally being met with satisfaction, fought the buildup until she could hold it back no longer. She screamed as Samantha shuddered, getting slammed by their host’s giant cock. Skylar squirted into Sam’s face as she violently came from the incessant tongue and fingers attacking her most private place.

Samantha felt the inevitable response from the large cock drilling her doggie style. “Oh yes, Jackson, yes, yes, YESSS!” Her body shook, and her pussy gushed wet all over him as he blasted ribbons of white in her sloppy pussy. The triple intensity of the three drained them together until they were all exhausted, satisfied remnants of what they were just minutes ago. “It’s official, Jackson,” Samantha purred. “The bed on your plane is officially broken in, with two wet spots to prove it.” All three laughed.

They all finished and lay down together on the bed, falling asleep until they needed to go. They all took a shower in the plane for the first time, inaugurating another part of the new jet, and then dressed for downtown Seattle, the women in business casual and Jackson in a business suit.

“Samantha, I have another meeting in the city today. With Skylar still working today, you’re free. Early this evening, you and Skylar can just take a taxi to the Fairmont Olympic. We can go out together at a restaurant, and after dinner, we’ll take off for the evening’s events. Having both of you by my side will make me feel great.”

“That sounds perfect, Jackson. Oh, and when you attend your Starbucks meeting, they’re going to present a new tool to clean espresso machines—do me a favor and vote to accept the idea. Will you do that for me, Jackson?”

Jackson was startled at hearing such highly restricted corporate news. “Why do you want me to do that? How do you even know that?”

Samantha answered casually and plainly, much different from Jackson’s unexpected tone.

“Because I know of the company and their invention. It will save the company money, and the baristas will love it. You always tell me how important it is to have happy employees. Evaluate it yourself, but I know it is a good business idea. So vote yes, okay, Jackson?” She moved in to face him, giving him a deep, passionate kiss as she rubbed her naked body all over his. They continued their sexual escapades for another hour and then took another shower together before getting dressed.

“Samantha, I have a question,” he said as they were dressing together.

“Yes, baby?”

“You have time again to be with me for a week and a half, like old times. Whatever happened to that guy you found and have been with so often for the last five months? Is he still around? Why all of the free time for you now?”

“Oh, he is around, but things change. You are my best client, and I realized that I need to be with you more than I have,” was the nebulous reply. There was a look in her eyes that told him she wasn’t telling him everything, but he knew it was all she was going to share with him. It was the most detailed response he had ever gotten from his longtime escort companion. He decided not to push the point. He detected something had changed. For the better?


Skylar and Jackson attended their first board of directors meeting. Meanwhile, Samantha had an all-day encounter with another one of her best clients. That evening, it was back to the Fairmont Olympic for an evening of sexual debauchery with the multi-billionaire and his smart and gorgeous assistant, Skylar. As they left the hotel for the second board meeting, Samantha went home to pack for the next nine days in Europe.

The six-hour flight from Seattle to New York was nothing short of sexual debauchery.

“Fuck me, Jackson! Fuck me harder!” Sam shouted as he pounded her pussy as she lay with her naked ass pointing at him, her legs spread to give him the best possible angle to her pussy.

 
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