Milf Cruise Upgraded

This is a work of fiction.

Names, characters, businesses, events, and incidents are the products of the author's imagination

. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are over the age of 18.

Hello again. This story is another young man/ older woman romance story, á la the Love Boat. For the lovers of big beautiful women like me, this one's for you. I hope you enjoy it.

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Ray stepped into the cruise terminal, feeling on top of the world. The feeling seemed to be shared by everyone in the terminal. What could be more exciting than a Caribbean vacation, right? If everything went to plan, this trip would culminate in a memory that he would treasure for the rest of his life.

The young man stopped near the entrance to the check-in line and looked around. "Missy should already be here. She's always super early for this sort of thing." He thought. The five times they'd flown together, she would be at the airport three hours early. He didn't see her.

"Ray!"

He turned and saw Dina coming towards him through the crowd. Dina, Missy's best friend, and her boyfriend Lars were coming as well. They'd all been looking forward to it. But Dina wasn't dressed for a cruise, Ray noted. He frowned when he saw that she didn't have a bag with her either. Ray knew, that the plan was already knocked into a cocked hat.

Dina walked up to Ray but didn't look up at him.

"What the heck is going on?"

"I, ah ... she's not ... coming." Dina held up a pale blue envelope.

His shoulders fell. "She's breaking up with me? Now?" Ray sighed. They'd been dating for almost three years. "At least she didn't do it with a text," Ray's voice dripped with bitterness. Dina flinched like she'd been poked.

Finally, Dina gathered the nerve and looked up at him. Ray was a good-looking guy, trim, twenty-eight years old, educated, and well-employed. He kept himself well-groomed with dark hair and eyes. "I think she figured out your plan for this trip and freaked. I'm so sorry, Ray. She's such a stupid bitch." Dina reached out and grabbed Ray's forearm. "Lars sends his best."

Ray nodded. Dina kissed him softly on the cheek and walked out of the terminal.

He pocketed the envelope. "Well, old pal, looks like you are oh for two," he whispered to no one in particular. Ray picked up his backpack, slung it over the handle of his wheeled duffel bag, and proceeded to the check-in counter.

The pretty blonde ticket agent smiled sweetly at him as she handled his passport. "Is the rest of your party here?"

Ray didn't return the smile. "There is no party. Just me."

The agent's face fell. "Well let me look at ... oh." The agent saw the nature of the reservation and knew there was nothing further to be done. The agent handed him his boarding pass and itinerary. "I'm sorry."

Ray smiled wanly, "Yeah, that seems to be the general consensus."

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At 3 p.m. Ray boarded the Atlantic Star, the flagship of Pinnacle Cruise Lines. She was over a thousand feet long and had twenty decks. A bright blue and gold banner hung over the gangway. PINNACLE CRUISE LINES WELCOMES THE DAVIDSON HIGH SCHOOL CLASS OF 1997!

He kind of perked up seeing that. Maybe there could be a silver lining in this rain cloud. A twenty-five-year reunion meant there could be some unsupervised soccer moms, running about. "That could be interesting for a newly unattached fella." Ray thought.

Ray hung about on deck, like a lot of the passengers, to enjoy the moment the ship pulled away from the pier. It was a gorgeous day in Port Canaveral. He pulled the envelope from his pocket and opened it. A folded letter was inside.

Ray's eyes rolled, and he made a frustrated sound when he finished reading it. If you can imagine the archetypical breakup letter, this was it.

Ray,

I'm so sorry but ... blah blah blah, you're such a great guy, blah blah blah, I'm just not in the same place, blah blah blah, I know you'll find someone great someday, blah blah blah, we can still be friends, blah blah blah. Missy

That "we can still be friends" part stung the worst. It always had. Ray refolded the note, jammed it, and the envelope back into the pocket of his jeans for later disposal.

"Why the fuck do I always seem to be the

interim

boyfriend? The one who's good enough to be with, but not good enough to keep forever? Almost three years and this again." Ray fumed. Tears of frustration welled up but he wiped them away angrily.

Ray stood on the rail with the other passengers as the Atlantic Star got underway, sounding two long blasts on the ship's horn as the last mooring line was brought aboard. There was lots of cheering from everyone, folks waving to loved ones on the pier. He wished he could echo the sentiment.

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The stateroom was spacious. It had a central living area, with a balcony, and two bedrooms with their own baths. He'd reserved a family suite for the four of them, plenty of room. Now it was going to be a sad reminder for five fun-filled days. Ray unpacked and decided to wander the ship for a while, as the ship left Port Canaveral. Eventually, he ended up in one of the themed dining areas for a bite to eat.

On his way back to his stateroom, Ray passed the ship's comedy theater and noticed it was letting folks in for an evening show. Realizing it was nearly impossible to be miserable in a comedy show unless Pauly Shore was the headliner, he altered course and filed in with the rest. The first smile of the voyage finally made its way to his face.

Ninety minutes of comedy and two drinks later, Ray felt a lot better. Laughter and good beer just seem to have that effect on him as a whole.

Taking a roundabout route, Ray got to his deck having made a mental list of all the shit about Missy, he was better off without. The list was far longer than he'd have thought. Ray decided that such a list should be done sooner in any future relationships. "Because I'll be damned if I'll be a three-time loser." He thought glumly.

The guide maps on the bulkheads were terrific and he navigated toward his passageway without difficulty. Ray heard before he saw the couple arguing around the corner.

"So, you brought me on your reunion cruise, just to hook up with your old high school fuck-slut on the very first night, huh?" A highly agitated female voice yelled.

"Uh oh," Ray thought as he turned the corner. Three doors down on the right, a tall couple stood. Ray was five foot, eight inches, and had never been overly concerned with his height. He was taller than ninety-five percent of the world's female population and that had suited him just fine. The man was six feet, two or better, with a beer gut hanging over the edge of the towel around his waist. The woman, however, was an absolute attention grabber.

"Now that is a whole lot of gorgeous," Ray thought admiringly. The blonde woman was at least six feet tall in her flat sandals. Dressed in a form-hugging sun dress, the woman had a Rubenesque frame, busty and hippy with an hourglass figure. He caught his breath and with difficulty, diverted his eyes from the pair.

The man in the towel replied with a snicker. "Hey, it's not my fault you came back early. Stacy here was just leaving."

The woman pushed her way past the toweled man, into the stateroom. "Fuck you and fuck Stacy too, I'm out of here."

Any further conversation was muted as the door closed. Ray passed on by, letting himself into his room, two doors down on the left. He sat down on the sofa and turned on the ship's television system. The entertainment options were mostly movies like you'd find on a long transatlantic flight and Ray wasn't interested in any of it. Flipping to the ship's live attractions, Ray spotted something that had grabbed his attention when he was booking the trip. The Atlantic Star had a jazz club called the Blue Note. Inspired by an old Paris jazz club, it went along with the ship's themed areas, showcasing different countries, their art, entertainment, and cuisine. At the Blue Note, there was live music every night the ship wasn't in a port.

It was nearly nine p.m. "Yeah. That's gonna make my night." Ray knew that if he was going to enjoy this trip at all, keeping busy was the way to do it.

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Ray changed his shirt to something more appropriate for an evening and headed out. As he got near the elevators, he heard raised voices again.

"Ma'am, I'm very sorry for your circumstance but there's nothing I can do, the ship is full to capacity. It is peak season. There are no open rooms."

Ray turned the corner to find the stunning blonde woman from earlier towering over a Pinnacle crew member in his white uniform. She was clearly upset, standing there with her two bags.

"But where am I going to sleep?" She said with a worried expression.

The clerk gave her a sympathetic look. "Ma'am you would not be the first, nor the last, to live out of a gym locker and sleep on a chaise lounge at one of the pools. There are blankets available if needed. This happens at least once a trip in my experience. Cruises seem to bring out the best in some people and the worst in others."

Ray had walked past them and was already in the moving elevator when a thought occurred to him. When the elevator got to his chosen deck, he punched the button to go back up to his own. When the elevator doors opened, he saw that the blonde had moved to sit down in a corner chair, her face in her hands. The ship's clerk was gone. Ray approached the woman.

Before he'd gotten too close, she sat up and looked at him, clearly annoyed at being disturbed. "I assure you fella, I'm not looking for any company right now." She said with a frown.

Ray looked at his hands. "I'm sorry to disturb you but I think I can help."

Clearly thinking he was an asshole looking for a score, she laughed brutally. "I rather doubt that."

Ray looked up and met her eyes. They were ice blue. "Just hear me out. My companions decided at the last minute they couldn't make it for this cruise. So, I'm stuck with a two-bedroom stateroom, all by myself. So, I'm happy to offer you one. No strings, no expectations, and no charge."

The woman stared at Ray dubiously, not saying a word.

Shrugging, Ray held out his extra door card. "I'm going down to the Blue Note for drinks and some jazz. Why don't you check out the room, verify there's nothing nefarious going on, and maybe I'll see you later."

Not taking her eyes off Ray's, she took the door card. "I'm going to have ship's security check this out with me."

Ray smiled. "Smart lady." As he turned to walk away, she spoke. "Why didn't your friends come?"

Reaching into his front pocket, Ray pulled out Missy's note and handed it to the beautiful woman. Then he turned and headed to the elevator, with a giant exhale. It seemed to Ray that he'd been holding that breath since he'd read the note. It felt good to be rid of it.

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An hour later in the jazz club, the tall blonde slid into the curved booth with Ray. She looked at him expectantly. "This is an uncommonly ... kind gesture, and I really appreciate it, but I have a question."

The band was between sets so they could talk easily. Ray raised his glass of beer to his lips and smiled. "Shoot."

The woman looked him in the eye again. Ray liked her direct manner. "Why didn't you just get a refund, and not go at all?"

Ray set his glass down. "I'm an infrastructure coordinator for the port authority. The P.A. gives us these attaboy-points for good performance, that we can trade in for cool stuff. I traded in about six years' worth for this trip. If I'd canceled the trip, I'd only get about two hundred bucks back. Alone or not, I figured it was pointless to not go."

The woman thought about it, before finally smiling. "I'm Tyra."

Ray smiled back and introduced himself. The band came back on and played another forty-five-minute set and the two of them sat and enjoyed it with another round of drinks. Ray couldn't help looking over at her. Her height, light hair, and blue eyes spoke of Norwegian ancestry. She had broad shoulders for a woman, but they were offset by uncommonly beautiful facial features. Ray imagined her as the queen to some ancient Viking chieftain, capable of fighting alongside him in battle and fucking his brains out after the carnage.

She favored light makeup with pink tones and it suited her. Her wavy blonde hair was worn long and loose. Ray's best guess put her somewhere around forty years old.

Later, as Ray and Tyra walked back to their room, she once again revisited the subject of their cohabitation. "Listen, I want to have a clear agreement between us. I stay in the other bedroom. No funny business, no perving, no ungentlemanly behavior." Tyra said with a smile.

"Well, that covers me, but how do I know you're not going to try to sneak into my room in the middle of the night?"

Tyra laughed. "Trust me, you're not my type."

Ray shrugged and offered his hand. "Then I think we have an agreement." Tyra shook it.

"I have just one more question." With a smile, she asked, "What the hell is an infrastructure coordinator?"

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Back in the stateroom, they said goodnight and went to their separate rooms. Lulled by the motion of the ship, they both slept soundly until they were rudely awakened around three a.m.

"Tye! Tyra! You bitch!" The yelling was punctuated by a loud pounding at the stateroom door. Ray and Tyra exited their rooms at the same time. He was in a t-shirt and boxers and she was shrugging into a bathrobe, over a short lacy nightgown. Tyra raised a hand to Ray in an "I got this" gesture.

Ray nodded and stood back as Tyra unlocked and opened the stateroom door. Her ex-boyfriend Charlie stood there, disheveled and smelling of booze.

"There are you umm ... there you are, you ... bitch. Stacy told me you've already shacked up with some other fucker." Charlie yelled.

Tyra stood tall. "Charlie, I'm gonna give you five seconds to get the hell away from me, then I'm calling security." Ray admired her. She wasn't afraid of this drunk.

"Fine, call them! See if I care! There ain't no jail on these boats."

She was quick with a comeback, "Then maybe they'll pitch your cheating ass over the side!"

Tyra stepped back and walked to the intercom on the wall. Ray saw that ol' Charlie was about to step into the stateroom behind her and deftly stepped into his path, at the doorway.

The drunk glared down at Ray and unconsciously took a big step back. The smaller man was smiling at him and it unsettled Charlie. "Who the fuck are you? You'd better step back before you get hurt, little man." Charlie spat.

Ray could see folks peeking out of their stateroom doors. "Let's wrap this up," he thought.

"Sorry, Charlie old pal, but Tyra's trip has been upgraded." Ray heard Tyra sigh and whisper, "Oh shit."

It took Charlie a few seconds to realize he'd been insulted. When he did, he growled and grabbed Ray by the shoulder of his left shirt sleeve.

"No, Charlie, don't do this, I'm not with him," Tyra yelled excitedly.

In the time it took Tyra to take a step, Ray spun down under the large grasping arm to appear next to Charlie, with Charlie's hand twisted in his t-shirt. Just as Charlie's eyes tracked Ray with a confused look, Ray's left arm came up and over the big man's right shoulder, as his right hand pulled down on Charlie's right wrist. The combination of motions and some strength on Ray's part, threw the drunk man forward, off balance, and introduced Charlie's forehead to the metal doorframe with a thud.

The ship's security team rounded the corner just as Charlie sank groaning to his knees. "Hey, can you help me with this fella?" Ray smiled at the big men. "I think he's had too much to drink. Looks like he stumbled."

The security team took hold of Charlie. "It's okay, we've been looking for this guy. He's been yelling for some woman on four decks."

"C'mon fella, it's off to the brig for you," A security team member said as they hoisted the big drunk. "I doubt you'll be enjoying this trip very much."

Ray closed the door as the team left. "Looks like they do have a jail after all," he said with a smile. "Well, g'night." Ray turned back to his room without another word. Tyra could only stare after him in amazement.

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When the sun came up, it found the Atlantic Star moored up in Freeport, Grand Bahama, on a gorgeous morning.

Ray stepped out of his bedroom to find the lovely blonde sitting dejectedly on the sofa, still in her robe. Being a pretty sharp fellow, he figured that any plans Tyra might have had for the port visits, probably went right out the porthole if her ex had paid for the trip. Since Charlie was here for the reunion, it seemed a fair assumption.

"Listen, Tyra, I don't know what your plans are for today, but my trip came with the works. I'm headed out to a beach resort on one of the eastern cays on this island. It would make me happy if you'd join me. Our agreement still applies." Ray added with a smile.

Tyra lifted her head. "Are you sure? I don't want to be a bother."

Laughing, Ray feigned thinking with his finger on his chin. "Hmm, let's see. I could walk along a tropical beach alone, feeling sorry for myself, or I could walk along a tropical beach with a beautiful woman. Whichever shall I choose?"

Her derisive look made him smile. "Go on. Get dressed. Our ferry leaves in 45 minutes."

Tyra smiled back and hopped up to her feet. Ray enjoyed watching her voluptuous body move under the robe.

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The couple boarded a small ferry that took them out to an old resort on one of the furthest cays. It was a tropical paradise. Palm trees, clean sand, crystal clear waters, and fewer tourists. When they arrived, Ray arranged for a small thatched gazebo on the beach, lounge chairs, snorkel gear, refreshments, and towels. It was perfect.

As they got ready to head into the water Tyra nearly gasped aloud when Ray took off his khaki shirt.

"Holy cow, the man is cut!" Tyra thought as she averted her eyes. But then thought better of it. "Why not enjoy the view?"

Ray's upper body was terrifically developed, but not like a bodybuilder. He was lean and toned with great definition. Not much in the chest hair department, which Tyra secretly appreciated. There was no harm in looking. Ray certainly had been checking her out. She would have had to be blind not to notice his admiring eyes.

"Geez, Ray. Gym much?"

The man smiled. "Nope, not a bit. Martial arts. I've been studying since middle school."

Tyra tried not to show how impressed she was. "Oh, that would explain the knot Charlie must have on his head this morning."

Her face turned serious. "So, you could have really hurt him if you'd wanted to. But you didn't."

Ray shrugged. "That's not my style, or why I'm into martial arts."

"I'm glad," Tyra said with a genuine smile.

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Peeling his cargo shorts, Ray revealed his swim trunks. They weren't long surfing shorts or a speedo, but something just between them in length. They showed off Ray's toned lower body to good effect and Tyra enjoyed it.

He picked up his loaner snorkel gear and grinned at Tyra. "Coming?"

She smiled back. "Right behind you."

Ray was knee-deep in the water, spitting into his face mask when he looked up. Tyra came down the sand towards him. Shed of the oversized t-shirt she'd worn off the cruise ship, she wore a bright blue one-piece swimsuit. The legs were French cut and it had a deep plunging neckline that was laced most of the way up. It still showed a marvelous amount of cleavage. Tyra's breasts were very large. A full-body shudder rolled through Ray's body, and his heart raced.