MILF Cruise - the Cougar

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. As you may have surmised, this is a sequel of sorts to MILF Cruise-Upgraded. However, it isn't a continuation of Tyra and Ray's story, but an independent story that runs concurrently to Upgraded, with some characters overlapping both stories and a completely new main character. It is not necessary to read Upgraded first, to enjoy this story. That's why I'm not going to number these as chapters.

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MILF Cruise - the Cougar

Day 1 - At sea.

Ian was already tired. The Pinnacle Cruise Lines ship, the Atlantic Star had sailed at 3 p.m. from Port Canaveral and the first evening of the cruise was always the worst. As a ship's concierge, or customer service rep, in any other situation, his job was to assist passengers in any way they needed. Plenty of folks get lost on a ship where there are maps on the bulkheads. Or they are concerned over their bags not being in the room yet, or any other of a million other concerns, real or imagined. Already there had been a couple that broke up and the jilted girlfriend needed another room. Ian patrolled his section of the ship, usually staying near the elevators or common areas. It looked like it was going to be a long evening.

"Excuse me?" a woman's voice said from behind him.

Ian turned and when he saw the woman, his heart jumped in his chest and a shiver ran through him. She was immaculately dressed in a grey, curve-hugging business dress with four-inch black leather heels. Her jewelry sparkled at him.

"Can ... can I help you?" He replied.

When the strikingly beautiful woman smiled at him, his discomfort tripled. There was something predatory in her smile. She wore blood-red lipstick and burgundy eye shadow, which perfectly complimented her shoulder-length auburn hair and dark eyes. Ian couldn't quite place her age. He figured anywhere between thirty-five and fifty-five, and her figure gave nothing away in that regard. One thing was certain though, she knew how to make a first impression without saying a word.

"I hope so. My door card doesn't seem to be working." She held up the card. "It worked when I first came onboard this afternoon, and now it doesn't."

He took the card from her hand and felt her red-painted nails graze his hand softly. He caught a faint scent of strawberries.

"I'm sure it's ah, nothing, I'll just ..." Ian was about to do his usual double-check on the passenger's door, but in an instant, he changed his mind. This did NOT look like the kind of woman to be bested by a card lock.

"I'm going to get a ... replacement card for you." The woman gave him a dazzling smile, which sent Ian's heart racing again. Everything about this woman spoke of confidence, refinement, and class, from the way she spoke, how she stood, and how she walked.

The woman reached out and ran her hand down the young man's forearm as she leaned in to read his name tag. "That would be lovely ... Ian. I'll wait right here. Don't keep me waiting." She added with a wink.

"Umm ... what is your room number, ma'am?"

The woman smiled as she replied. "My name is Sonya, and my room number is 777."

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The woman chuckled softly as Ian sped off.

"This is going to be such a fun trip," Sonya thought. Things were already going her way. This was her second cruise this year, but she had a clear goal in mind this time.

Jason, her husband of twenty-four years, had passed eighteen months ago, after a grueling long illness. It had been a blessing when it was over. After six months, she'd pulled herself together and got her life back in order. Her husband's last wish was for her to continue in whatever way made her happy. So, she joined a gym and began eating right. A year of hospital cafeteria food and fast food had taken its toll.

She'd taken her first cruise shortly thereafter and it had been exactly the break from regular life she'd needed. Though she went by herself, she'd met a beautiful Latin couple on the first evening and spent a lot of time with them in each port. On the last evening of the trip, she'd let them seduce her and spent that night fucking them in as many ways as she could. Remembering that evening made her pulse race even now.

In the months that followed that sexual reemergence, she began dating again, but guys her age left her cold. They were usually looking for wife number two or three or four. And as a successful businesswoman of means, she was a prime target. But that wasn't what she was looking for. Been there, done that. After so long with her husband and the hardships that concluded it, she wasn't looking for a repeat of that scenario. However, she wasn't the sort to be happy living alone. She needed love and companionship and sex. On her terms.

Sonya smiled when she saw Ian return. His brisk walk was nearly a jog. He was of medium height, lean and cute, with sandy hair and hazel eyes.

"Here we go, ma'am. I ... I mean ... Sonya." Ian held the new card with a bashful look. "Shall we go to your room?"

Sonya grinned. "I don't know handsome, we just met. A girl usually expects dinner first. Or at least some flowers."

Ian's brain shorted out and he dropped the door card. "That's not what I ... I meant to try the card, I didn't mean ... anything inappropriate, ma'am."

Sonya loved seeing his reaction. She adored the shy ones. She loved the way they looked at her. It was more than appreciation or admiration; it was more like ... worship.

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After deciding against men her age, she set out to find someone younger. And she'd thought her gym was the best place for that. But, just like the older guys, the young confident studs around the gym didn't arouse her interest either, though they certainly didn't lack for trying. Sure, they were great eye candy, but ...

Then she noticed Sam. Sam was a gym employee. Young and cute. Sonya watched him for a while, from her treadmill or stationary bike. He seemed good-natured and smiled a lot. He seemed at ease with the young hot girls, but when Sonya approached the counter to get a towel or ask a question that she already knew the answer to, he became clumsy and nervous. She loved that. Cute and shy? Oh, that was her cup of tea. For two weeks she made every effort to engage him, at least three times a night. His awkwardness made her shiver in delight.

Finally, she went in late one evening and as she left, she asked Sam to escort her to her car for safety. When they got to her sedan, she thanked him with a kiss and asked him if he'd like to have dinner with her. It had been the start of a torrid sexual affair that had lasted for months and cemented who she was sexually and what she wanted in her lovers. She was a cougar, and she wanted her cubs.

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Ian escorted her to her room and verified the door did open with the new card. Sonya took the card and gave him a dazzling smile.

"Thank you so much. So, about that dinner? What time is good for you?"

Ian's eyes flew wide in shock. "I ah ... I'll be working quite late tonight. The first evening, passengers are always ..."

She stepped into him and laid her fingers on his breastbone. They were eye to eye, in her heels. She looked at him and as their eyes met, she cranked up the seduction to eleven.

"What about dessert then, say, ten o'clock? In my room?" she whispered enticingly.

Ian nervously glanced around to see if anyone had taken note of them. "Ma'am, we're not allowed to fraternize with passengers." He whispered. "I could ... lose my job."

Sonya pouted. "Sweet boy. There are many jobs to be had. But only one of me." She emphasized the last three words with a finger tap on his chest. She smiled and walked into her room. Before closing the door, she added, "Think about it."

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At nearly ten o'clock on the dot, there was a knock on her stateroom door.

"So glad you could make it," Sonya said with a cheery smile. Ian checked both directions down the passageway before stepping in. He was dressed in casual slacks and a button-down short-sleeve shirt. She got a light whiff of a pleasant aftershave.

"I ah, I really shouldn't have but I couldn't ..." His voice failed him as he saw Sonya. She'd replaced her dress with a long silver-blue silk robe, that she wore closed and tied. He could see her stockings and high heels remained.

With a look of awe mixed with a deep longing, he finished his statement. "I couldn't help myself."

Sonya closed and locked the stateroom door, then turned and stepped close to him. "I know the feeling." Wrapping her arms around his neck she leaned in and kissed him deeply. When she broke the kiss, he took a big breath.

"Oh my. This is ..." he couldn't find the words to continue.

"Are you married?" she said, looking intently into his eyes. Ian shook his head. "A girlfriend, maybe?" He broke their eye contact and frowned. "No," he said with a hint of bitterness in his voice.

Sonya gave him a warm smile. "Then tonight you are mine."

She pulled his face to hers and kissed him once again. He wrapped his arms around her and pulled her hard into his body. She could feel his hard cock against her hip.

After leading him toward the bed, Sonya slowly undressed him, running her hands over his lean, wiry body. He gasped when she ran her hand over his engorged member.

Sonya smiled appreciatively. "Has it been a while?" Ian swallowed and nodded.

"Good. Then you'll have plenty for me."

She untied her robe and let it fall open, revealing her full breasts and a gleaming hairless vulva. Her tanned skin showed no trace of tan lines. She still wore her garter belt, stockings, and pumps. A string of beautiful pearls hung seductively between her breasts. Sonya reveled in the adoration and disbelief in his eyes when they fell upon her body. It made her pussy wet in anticipation.

"Do you want me?" she whispered eagerly.

Ian looked back into her tiger's eyes and trembled. "Oh God yes."

"How wonderful." She smiled and glanced toward her feet. "Come show me."

Like a supplicant in a temple, the young man fell to his knees before her. "You're gorgeous." He whispered. "The sexiest woman I've ever seen. I can't believe you want ... me."

Reaching down she gently lifted his chin. She caught his eye and held it. "My job brings people to my door every day, for over twenty-five years. I've become an excellent judge of character. You are very sweet and cute, and good. Traits, that are wholly unappreciated by girls your age until they have been mistreated over and over, by the tall hunky ones. I didn't just approach you at random. Do you think I'm a slut, dropping her robe for anyone?" She looked at him intently.

Ian shook his head vigorously.

"I watched you for nearly an hour. Watched how you dealt with these simple people and their silly issues. You were patient, polite, and thoughtful. You're a good man. Someday a bright young woman will realize this and grab you for herself. Until, that day ..."

Leaning down, she reached around his head and brought his mouth to her nipple. She moaned huskily as his warm mouth enveloped it. "Yes, that's it. Touch me. Touch me everywhere."

Encouraged, Ian reached around to grab her firm, tight ass with both hands.

With an appreciative moan, she whispered. "There are so many yummy things I want to do with you. But you can't stay the night, can you?"

Releasing her plump nipple, he replied with real regret in his voice, "No. I want to, believe me, but I share a room with another crew member. If I'm gone too late, it could get reported."

Sonja smiled wistfully, "Then we better not waste a moment." She pulled his face into her. "Get it all wet and ready for your cock sweetie."

He didn't reply, just wrapped his arms around her round ass and pulled her pussy to his mouth. Sonya smiled and closed her eyes as his skillful tongue began licking her full pink pussy lips. She moaned as his tongue slid into her slick hole.

"Oh yes. You've done this before. How lovely," She moaned.

Ian wasted no time, licking and sucking while his hands ran up her stockinged legs. Her gym sessions had been effective, her legs were lean and toned. He kissed the inside of her thighs and made her giggle with little nips and kisses on her outer labia. He pulled back the hood over her clit, pinching it gently with his wet fingers. Her breathing turned into a heavy pant when Ian slipped two fingers into her dripping pussy.

"Oh yes sweetie, that feels so good." Sonya moaned. "Go easy. Let's build this fire slowly."

Ian's reply was a hummed "mmm" directly on her engorged clit, as his fingers found her g-spot. Her hips flexed and her head snapped back as she wailed. After several wonderful minutes, she reached down and pulled his head away from her. Looking down at his wet shining face, she smiled brightly. "Get up on the bed baby."

Sliding his hand from her pussy, he stood. She loved seeing the ardent look on his face. He turned and sat down on the bed before crawling back on his elbows.

She took a moment to take in his lean, firm body before crawling up over him. Moaning softly, she lowered her head to take his cock into her warm and wet mouth. A shudder ran through Ian's body, and he moaned. She sucked the pre-cum from his cock and enjoyed the taste, smearing it on her tongue with the head of his cock. Sucking gently, she ran his cock in and out of her mouth smoothly, the head of his cock butting nicely against the back of her throat. She brought up her hand to cup his balls. When his hands slid into her hair and grasped her head, she knew he was getting close. Lifting herself off him, she moved further over his body and straddled his hips. The rapturous look on Ian's face made her shiver with delight, as she slid her sopping pussy on top of his cock.

"Yes, I'm gonna ride this hard cock." she whispered, her voice going deep and husky.

Ian gasped as he felt the head of his cock slide into her warm wetness. "Oh Sonya," he whispered.

Sonya rocked her hips, taking his full length inside of her. "Yes baby, give me all of it." She rolled her hips over and over, loving the ecstasy she saw on his face.

Ian's mind whirled. He'd always heard of crew members hooking up with passengers, but it always seemed more like a folk tale or fantasy, as the company took a dim view of anyone doing so and the punishment was immediate dismissal. But how could he pass this up? He was a hundred percent sure that he could find another job. But the odds he'd find another gorgeous older woman that wanted him like this? Pretty long he figured.

Ian reached up and grabbed the wonderful tits that hung in front of his face. He ran the side of his knuckle over her plump nipples before lifting his head to take one in his mouth.

Sonya reached down and cradled his head to her. "Oh yes baby, suck on my tits. That's so good." She moaned. "If you suck harder, I'm gonna cum on this beautiful cock."

He was only too happy to oblige. The intimacy of her slick pussy sliding down his length and the firm nipple in his mouth caused his whole body to shudder in excitement. Sonya felt it and moaned appreciatively.

"Oh, I'm gonna cum baby, fuck me. Fuck me!" She wailed.

Ian released her breasts and slid his hands to her firm round hips and pushed her down as he hammered up into her.

"Oh, fuck yes! Yes, baby! Do it, cum inside of me! I want to feel it!"

When Ian exploded into her, an enormous shudder ran through Sonya as she climaxed with him, both moaning loudly. She could feel his massive load fill her womb and she sighed with contentment. Finally, she collapsed on top of him.

After a few minutes to catch her breath, she looked into his eyes and stroked the side of his face. "Such a good boy."

The young man smiled brightly at the compliment. Between breaths, she asked, "Who taught you how to eat pussy like that?"

He smiled a little sheepishly. "My mother's best friend."

Sonya lifted her head and grinned. "Really? Did she take your cherry?"

He laughed. "Yeah, she invited me to a private little New Year's Eve party before I left for art school. I stayed with her for over a week."

She giggled and slid off his chest, to rest on her side under his arm, one leg over his. "Your mother's best friend. How cliché. Was she hot?"

He nodded vigorously giving her a "you better believe it" look.

Grinning mischievously, she slid her hand down to stroke his cock. "How wonderful for you both. Perhaps I should send her a thank you note." His cock began to harden again in her hand.

"Do you think we have time for one more before you have to go?" she said gazing into his eyes. He didn't bother answering, he just leaned in and kissed her deeply. After a few passionate moments, she broke the kiss, smiling at him. "There was nothing wrong with the keycard."

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Day 2 - Freeport, Grand Bahama

Sonya spent the morning enjoying the beaches of Grand Bahama and sampling the wonderful local food. She'd caused quite a stir when she left the ship, dressed in a red thong string bikini and a sheer white cover-up. A wide-brim floppy sun hat and sandals completed her ensemble. She got quite a few angry glares from the ladies on the ship, but she could care less. They had the same access to a gym and healthy foods as she did. Sonya managed a successful career, a home, and a husband, and still managed to keep a respectable figure until Jason got sick.

She got several offers for companionship while she lounged under a thatched gazebo on the beach, but she politely shooed them away.

The afternoon heat was reaching its peak when Sonya sauntered back up the gangway. A shower and a nap always hit the spot after a morning on the beach. She lived and worked in Cocoa Beach. The ocean was part of daily life, although it didn't compare to the beauty of the tropics. As she arrived on her deck, she passed through a common area and almost passed by a young blonde woman sitting in a comfy chair. She stopped when she heard sobbing. The young woman's shoulders shook, and her face was hidden in her hands.

Sonya knelt at the girl's side. "Come now sweetie, what's got you all twisted up?"

The young woman looked up at her briefly. "Oh, my fiancé he ... and now I don't ..." The woman began to sob deeply. It was a heartbreaking sound. Sonya quietly knelt there next to her. Best to let her get it out. When the sobs subsided, Sonya tentatively put her arm around the girl's shoulders.

"What's your name, hun?"

The woman looked up and met Sonya's eyes. "Lucy."

Sonya smiled at her. The girl's eyes were a lovely blue-green. "Lucy, are you the girl with kaleidoscope eyes?"

Lucy smiled weakly and wiped her eyes. "Yes, what's why daddy named me Lucy."

"Come on, let's get something sweet and chat for a while, shall we?"

Lucy wasn't a fool to trust any old stranger, but there was something about the older woman's face, something motherly and empathic. Lucy nodded.

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Sonya walked Lucy down to the German-themed area and headed for the bakery. The Atlantic Star had five themed areas based on different countries, their art, music, cuisine, and culture. Germany, France, China, Brazil, and Mexico.

After grabbing a couple of decadent German pastries, the ladies found a quiet place to talk.

As it turns out, Lucy and her fiancé Rich had also spent a nice morning on the beaches but returned at lunchtime.

"He left the stateroom to go get us some food, but he didn't return for nearly two hours! When I asked him where he'd been he said the line was just long for the food." The poor girl started to break down again.