Cougar Cruise

Story Info
A crazy idea leads two unlikely people to love.
20.3k words
4.79
59.5k
97
23
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
komrad1156
komrad1156
3,789 Followers

Mid-October, 2018

"Uh-huh. Sure."

"Dude, I am NOT kidding!" his best friend since junior high insisted.

"A cougar cruise."

"Yes, a cougar cruise!"

"Where 'hot' older women meet younger men. For sex."

"I knew you'd get it, man! Talk about great, right?"

"Yeah. Great. Woo-hoo."

"Come on, Gavin. Go with me, man!" his longtime friend, Darren Lewis, pleaded.

"Not in a million years...man," his friend replied in a monotone voice without even looking at him.

Like his best friend, Gavin Freeman, was also 27 years old. But unlike Darren, Gavin was well-educated, grounded, and had his feet planted firmly on the ground. It was amazing they were even still friends, let alone best friends.

Gavin had gone to college right after high school while Darren enlisted in the Navy. Four years later, Gavin had a Bachelor of Architecture degree, while Darren had a job skill.

The degree program was five years long, but Gavin went to summer school each year to include starting immediately after graduating from University High School in Tucson, Arizona. He was now working for his father at the architectural firm he'd owned for nearly 20 years, and couldn't be happier with his choice of careers. In a little over three years on the job, Gavin had established himself as a very solid architect in his own right, ending any comments about nepotism being the reason he was there.

Darren had been trained as a diesel mechanic and spent his time serving as an Engineman or EN, the Navy's designation for that career field. There was nothing Darren loved more than tearing apart a dirty diesel engine, fixing any problems he found, and putting it back together.

He found work back in Tucson within a month of getting out of the Navy and made very good money getting his hands dirty five days a week. Overtime was easy to get, so as it turned out, he made almost as much as his college-educated friend who made his living with his mind and imagination.

The other big difference was their looks.

Gavin was tall, handsome, and very fit. He'd wrestled and played tennis in high school and continued wrestling in college at the University of Arizona. He was naturally blond, had blue eyes, and truly looked like the all-American boy. Or maybe the all-American model. His family had money, but he'd been raised to work hard, been forced to earn his spending money growing up, and had been taught that every person was equal and deserved respect.

Darren was, well, not as tall, not even close to being as good looking, and while not a slug, anything but fit. Darren often looked disheveled, his curly, black mane more of a bird's nest than a hair style, and after working 8-12 hours in a shop, the last thing he wanted to do was workout. The only exception being the '12-ounce curls' he did several nights a week either at home or out at a bar with Gavin.

In spite of the obvious differences, they picked right back up where they'd left off after Darren came home and still hung out a couple of nights a week as well as Friday or Saturday nights with Darren dragging his reluctant friend off to some new dive or bar in hopes of scoring with some questionable-looking 'honey'. Gavin had tried taking Darren to nicer places and even took him to his father's country club once. But after less than an hour there, Gavin realized it was a waste of time and had never tried again.

But it wasn't like Gavin cared for the country club, either. His family had money, and now, he did, too. But money was secondary. The thing he truly loved was designing a building while tackling some new, tough design issue. Nearly everything he earned went in the bank, other than what he needed to pay his bills which included a very nice apartment located not too far from the Freeman firm.

Gavin had no problem attracting women. In fact, they tended to gravitate his way wherever he went. Even so, during college he was wholly focused on learning to be an architect and limited his social life to occasional 'hook-ups' and then only when he had the time.

He was now at a point in his life where sex was no longer even a small priority where women were concerned, and his thoughts had recently turned to marriage and starting a family. Having proven himself in his chosen career field, the next big challenge in life was finding a loving woman who was pleasant and easy to get along with.

Yes, he hoped to find one who was also beautiful, with beautiful defined as 'beautiful to him', but looks no longer played the role they had in the past. However, certain personality traits were now even more important to him than at any time in his life.

For example, any woman who was loud and outspoken was immediately out of the running, no matter how attractive she might be. He wasn't 'afraid of strong, powerful women'. He just despised being around anyone—male or female—who was loud or aggressive, and the reason why was obvious.

Gavin wasn't shy by any means, but he was quiet and soft-spoken by nature, and to the greatest extent possible, he avoided loud, obnoxious people like the plague. The thought of dating a woman like that was one thing he could never tolerate. On the other hand, Darren was the gregarious one, and he gravitated toward women who were at least as vocal as himself.

Not Gavin. He didn't like drama, gossip, or liars, and didn't tolerate people who did any of those things. He was well aware relationships required a lot of hard work, and that meant that while they weren't necessarily easy, they didn't need to be made more difficult by a woman who was loud, jealous, controlling, or constantly complaining.

It wasn't a lot to ask, or so he thought, and yet finding a woman like that, one who could possibly become Mrs. Gavin Freeman, was beginning to feel like 'the holy grail' of dating. He often likened his search to "The Three Bears" in which finding one that was 'just right' proved to be a very formidable challenge.

Darren, on the other hand, had a small, but very different, set of requirements.

First and foremost, they had to be genetically female. Second, they had to have all of their teeth. Third, they had to give good head. If a woman, any woman, could somehow manage to 'pull all that together', and if she was willing to sleep with him, Darren was her man. At least for that night. And as unlikely as it seemed, more often that not, he found a woman willing to do just that. But this 'cougar cruise' of his seemed like a bridge too far for his unlikely best friend.

"But why...cougars?" Gavin asked. "What's so special about older women? And how much older are we talking about?"

"Someone's coming around, isn't he?" Darren replied with a toothy smile while not actually answering his friend's question.

"I'm just asking. That's all."

"Oh, come on! You can't tell me you wouldn't be all over some hottie like...Jennifer Anniston or Courtney Cox. There is no way you wouldn't hit that!"

"First of all, neither of those women are going to be on this cruise—or any similar cruise, okay? Second, neither of them would be interested in any guy who wasn't a famous actor, singer, or athlete. But okay, I guess I kind of see what you're saying."

"Damn straight!" Darren said, now feeling like he was making headway.

"So...how much older?" Gavin said again.

"Uh...well. I uh, I don't really know. But check out these photos from last year's cruise."

Gavin reluctantly looked over at his friend's laptop, which just happened to be in his lap, and watched Darren scroll through a few of them as he turned the monitor enough so his friend could look with him.

The women he saw ranged from 'not bad' to well, downright scary. Some of them looked to be in their late 60s or even their 70s and none of them looked like Raquel Welch or Jaclyn Smith, two still-beautiful women over 70. He had no idea whether or not the pics were staged, but if they were real, there were evidently a whole lot of guys in their 20s and 30s willingly spending time with these 'cougars', the name for older women who liked younger men. The younger men, Gavin learned, were called 'cubs'.

Just before he was ready to give up, Gavin saw two women he thought were very attractive, and Darren noticed.

"Whoa! Go back," he told his friend.

"See? There's someone for everyone on these cruises, bro!" Darren said as his buddy checked out the two hotties for several seconds.

"So are you in?" Darren asked.

"Let me get this straight. We have to fly to Tampa to get on the ship, then we spend a week on a Royal Caribbean boat floating around while trying to get laid. By older women."

"And we see the Keys, Cozumel, and a couple of other places and drink a shitload of Mai Tais paid for by our generous cougars while getting laid! Talk about a good deal, right?"

"It's a lot of money," Gavin said as he looked at his buddy for the first time in nearly an hour.

"Oh, no way. Do NOT tell me you're even gonna mention money. Dude? Seriously?"

"It's not that I can't afford it, I just don't see where there's any...value...for the money spent."

Darren looked back at his old friend and said, "You can be a stuck-up prick sometimes."

That was the one area where Gavin was vulnerable. He couldn't help being born to parents that were well-off. And yes, he worked for his 'daddy', and there was no getting around that. But he'd busted his ass to get there and even more so to make a name for himself. Even so, he hated it when anyone thought of him as a 'rich kid' or in any way pretentious. In fact, he went out of his way to be one of the guys in every way he could, and hanging out with Darren was the ultimate proof.

He knew Darren knew that, and that meant he was aware that his best friend's feelings had been hurt, and that his words really stung. But before he could apologize, Gavin gave in.

"When does it start?" Gavin asked, knowing he'd lost the battle.

"December 8th. That's the day we depart. So...can I book us?" Darren asked, his tone much more subdued.

While Gavin enjoyed hanging out with his old friend, it was also true that he did a lot of things with Darren he didn't really care to do, but he also knew Darren would give him the shirt off his back without a second thought. Over the yers, he'd been a friend like no other, so if this was the price he had to pay, a few days on a cruise wasn't that much to ask.

Besides, Gavin had never been to any of the ports of call Darren mentioned, and just seeing them would be worth the time and money. And he also hadn't taken an actual vacation since going to work for his father, so he was long overdue.

"That's a slow time of year for us, so...what the hell. Yeah, I'm in."

"Seriously?"

"Yeah. Let's do this," Gavin told him with feigned enthusiasm.

Darren was suddenly 'jazzed' like never before.

"Oh, hell yeah!" he said as he pounded the keyboard. "Hey, bro. I need your credit card info."

Without the slightest hint of protest Gavin handed it to him.

"Here you go, Cub."

"That's me, man! I'm gonna be some sugar momma's cub! Maybe a whole bunch of sugar momma's cub!"

"You don't exactly need a rich woman, my friend," Gavin reminded him.

"Huh?"

"A sugar momma. You don't need one. You've got a ton of money."

"No. That's just a figure of speech," Darren told him as though Gavin might not know that. "But hey, if she's loaded and wants to, you know, buy her cub a Land Rover, or..."

Gavin had to laugh or he'd go crazy.

"So what all do we need to bring?" he asked as Darren booked them on the cruise.

"Dude, do you ever stop planning and just smell the coffee?"

Gavin managed not to laugh at his friend's incorrect use of the phrase and just said, "Sorry. I can't help it. That's just who I am."

"Yeah, well we're gonna change all that, my friend. You and me are gonna go cougar huntin' in December! No plans. No itinerary. Just hot, wild sex with beautiful, older women!" Darren said as he hit 'enter' for the last time, securing their reservations on the cruise.

"Oh, joy," Gavin said without expression, already dreading 'hunting season'. Darren ignored the dig and suggested they go grab a few beers.

"One. I'll have one beer with you," his well-dressed friend replied.

"So does that mean you're driving?" his buddy, clad in jeans and tee shirt, asked.

Gavin had to laugh again, and when he did he told Darren, "Gee. Way to break the code there, Captain Obvious."

"Captain Obvious. I kinda like the way that sounds! Hey, you think they'll let me steer the boat?" Darren asked his friend as he stood up before asking what was taking him so long.

Gavin only sighed and said he'd be ready in a couple of minutes.

******

Three days later in Phoenix, Arizona.

"Mom, you can't go alone."

"I'm 68 years young, and I believe I can do any damn thing I want!" her sassy, once-white-haired mother replied.

"Yes, okay. You can go by yourself. I'm just saying you shouldn't."

"And why not? Do you think I'm going to get screwed to death or something?"

Her 41-year old daughter still wasn't used to hearing her mother talk like that. It surprised her a lot less often now, and it rarely shocked her, but every now and then, her mom still floored her. The change began about a year after her father passed away, and she could remember the first time it happened like it was yesterday.

"I'm sick and tired of sitting around grieving, crying, and moping. Your father is gone, and I'm horny!" her mother had said one day while having lunch together.

Natalie Robinson had just turned 40, and had been divorced for a little over two years. She still hadn't met anyone who really 'did it' for her, and although she'd never say it out loud, she was 'horny' herself much of the time. But hearing her mother, her 'saintly' mother at that, say that word out loud had knocked her socks off.

"Mom! You did not just say that!" her daughter replied, the surprise written all over her face.

"I'm 67-years old, and...I still like sex! And for your information your father and used to do it at least..."

"Mom! Okay. I get it!" Natalie told her, frantically stopping her before she could give the number of times per week, or god-forbid, per day.

"Well, I'm old, not dead," her mother, Virginia Robinson, had snapped back.

Natalie gave up her married name after the divorce that came about due to her ex's serial cheating she had no idea was even going on for over a year before she found out.

"Then I'm sure there are still a lot of men your age who'd be very interested in doing, you know, that, with you," her daughter quietly admitted as she looked around to see if anyone else had overhead their embarrassing conversation.

Just saying that—to her mother—nearly made her skin crawl even though Natalie would love to be able to share her body with someone several times a week, too. And still being a very attractive woman, she had no difficulty finding willing partners. But because her sense of trust had been shattered, she'd rarely dated since her divorce.

Out of a sense of pure desperation, she'd 'hooked up' with very attractive men on two occasions, but that been it as no one else had ever really even caught her attention. They'd satisfied an immediate itch, but Natalie was sick and tired of living alone, and yet in spite of her best efforts, she'd come up empty-handed in her search for a new mate. And as much as she hated to admit it, it was very possible she was looking for love in all the wrong places. So as unlikely as it seemed, she had to admit that maybe her mom was onto something.

"Honey?" her mother said almost patronizingly, "I'm going on this cruise because I have no interest in men my age doing that with me. I mean, my God, have you seen what men in their 70s look like?"

Natalie let that comment pass as she most definitely did know what men her own age looked like, and replied with, "So your solution is to go on this...cougar cruise, right?"

"You're darn tootin'! Younger men are sexy! And they like cougars!"

"Cougars. That's just great, Mom," her exasperated daughter said.

"Don't get all high and mighty with me, Nat. In case you hadn't noticed, you're old enough to qualify as a cougar, too."

"Oh. No. Don't you dare say that!" her daughter replied.

"The rules say any woman over 40 is considered a cougar. Here. Look for yourself," her mother insisted as she turned her laptop around.

"The rules," her daughter muttered before saying, "Mom. I'm not even looking, and I'm definitely not looking for..."

Natalie stopped her protest when she saw several very attractive younger men on the laptop's screen and couldn't help looking.

"Well, well. Looks like someone else likes a little eye candy, too!" her mother said.

"Down, Mrs. Robinson!" Natalie told her smiling mother as she tried not to smile herself, unable to stop looking at one of them in particular.

Natalie finally forced herself to look away before saying, "Okay. I'll admit those two guys are fairly attractive, but when they look like they're young enough to still need their mothers to burp them, I don't really care what they look like!"

"Well, I'd not only burp both of them, I'd let either one of them 'do me' and if they both wanted to..."

"MOM! For crying out loud—STOP!" her distraught daughter nearly begged.

Equally distraught, but for the opposite reason, her mother got up and said, "How in the world do you think you got here, daughter of mine? The stork?"

Natalie just sat there shaking her head and wondering who this other woman was and what they'd done with her dear, sweet mom.

Two days later, when Natalie stopped back by to visit, she walked in and immediately apologized for 'not being supportive'.

Her mom really surprised her and sounded like her old self when she said, "Sit down, honey."

For the next couple of minutes she explained how much she'd loved Natalie's father, Ned, and how she nearly died when he did.

"But he's gone and nothing can bring him back. You do understand that, right, sweetheart?"

"I know, Mom. I miss him, too."

"Nat. Honey. Your father's gone, but I'm still alive, and I will not sit around knitting and playing bingo just to pass the time until I die, too! I'm sure this is difficult for you to understand, but I'm not just your mother. I'm a human being and a woman. And I'm a woman who still enjoys...male companionship. And I'm single, so I'm not being unfaithful. And I really, really want to go on this cruise."

She looked away for a moment then back at her daughter as she said, "I...I just don't want to go by myself."

Natalie knew her mom was right. It killed her to admit it, but she was 100% right.

"Okay. I give up."

"Honey, there's nothing to 'give up' on. I respect you for trying to preserve the mother-daughter relationship we've enjoyed all these years. But now that your father is gone, you have to let me live my life the way I want to live it. Okay? Please?"

"You're right. And...I'll try. No promises, but I will make an effort. Okay?"

"Good, because I already paid for your ticket!" her well-to-do mother announced, nearly flooring her stunned daughter.

"I...teach. I...still have school. I can't just..."

"Nonsense! That's what vacation days are for. And I just happen to know that you have a ton of them saved up, so you and I are going cub hunting, end of story!"

Natalie started to protest when her mother held up her palm and said, like people did 20 years earlier, "Uh-uh! Talk to the hand, girlfriend!"

"If you start 'Hammer-dancing', I'm disowning you," Natalie warned her mom.

When her mother stood up and sang, "Can't touch this!" and started moving around like MC Hammer, Natalie once again just sat there in total disbelief as her now-68 year old mother did a pretty decent rendition.

"I'm in daughter hell," she said as the Hammer dance kept going.

komrad1156
komrad1156
3,789 Followers