Jenn felt the shadow cross over her before even hearing his voice. She opened her eyes and looked up to see a handsome man clad only in a short pair of swim trunks, a towel hanging around his neck.

“Is this chair taken?” he asked in a rich, baritone voice.

“Uh, no. Go ahead,” Jenn replied as she watched him lay his towel over the back of the chair and take a seat. She couldn’t help but notice the way the fabric pulled tightly across his firm ass as he moved, causing her to shiver, despite the scorching sun.

It had been a cold, stormy day in February when Jenn impulsively said “yes” to accompanying her college-aged son (Gabe) on a trip to the Mexican Riviera. They found a resort that was highly recommended by some friends and booked their upgraded tickets. Jenn started having second thoughts immediately, but when the time came, she was more than happy to get on that plane.

As expected, upon arrival, Gabe quickly made friends with the college-aged crowd, while Jenn settled into the Privileged pool area for some much-needed rest and relaxation. She was soaking up some warm, late afternoon sun when she felt his shadow.

She hoped he hadn’t noticed her staring behind her oversized sunglasses, or noticed her goosebumps. He was about six feet tall, with dark brown eyes and hair (greying at the temples). He had wide shoulders, strong arms, a nicely defined chest with a moderate amount of hair, narrow hips, round butt, and powerful thighs. Judging by the paleness of his skin, he was a new arrival at the resort too. Jenn felt her body react to the sight of this handsome stranger - it had been a long time since she felt that tingle.

As he settled into the chair, he looked over at Jenn, catching her looking at him. He flashed her a smile that made his whole face light up.

“Hi! I’m Christopher, but you can call me Chris,” he said, extending his hand.

Jenn accepted it and instantly felt a bolt of electricity running through them.

“I’m Jennifer, but you can call me Jenn,” she replied with a nervous giggle.

After a few minutes of soaking up the sun in silence, Chris got up and dove into the pool. Jenn’s eyes were glued to him, watching every move he made. Occasionally, he would catch her looking and flash her a smile, making her tingle. When he climbed out of the pool, Jenn couldn’t help but notice the fabric clinging to Chris’s body, outlining his cock. Her breath caught as she imagined what it would be like if it was hard…

As Chris returned to his chair to grab his towel, Jenn felt a few drops of cold water hitting her burning skin.

“Sorry, Jenn! I didn’t mean to make you wet!”

Jenn blushed instantly. It was too late for that… “It’s just a little water; I won’t melt!”

Chris dried off and excused himself to go back to his room to get ready for dinner. Jenn was sad to see him go - she hoped that they would cross paths again soon.

A while later, Gabe and Jenn were having dinner in the Privileged dining room. They were seated at a table beside the window and were chatting about their afternoon experiences, when a large family was ushered to a table of ten, right across from them. It appeared that there was a couple in their seventies, a couple in their late twenties with two young children - a boy about four, and a girl about two, and a younger couple in their early twenties. There were two empty chairs.

Jenn heard that familiar, baritone voice talking to the host, and looked up to see Chris. He was making his way towards them. Jenn’s breath caught, but instead of coming to her, he sat with the family. He hadn’t noticed her. Jenn’s heart sank a little. Clearly he, and presumably his wife, were the missing link between the generations, but there was no sign of his wife.

Gabe and Jenn finished their dinner and left quietly. Chris didn’t see her. It was probably just as well. Gabe went off to find his new friends, while Jenn grabbed a drink at the beachfront bar and took a seat on one of the swinging beds to watch the sunset. It wasn’t long before a familiar voice came up behind her.

“Mind if I join you?” Chris asked.

“Sure, I guess so,” Jenn replied, smiling nervously, as Chris climbed onto the other side of the swinging bed. Her heart inexplicably skipped a beat. “You have a beautiful family,”

“Have you met them?” Chris asked surprisedly.

“I saw them at dinner. My son and I were seated right behind you.” Jenn replied.

“Oh. I’m sorry I missed you - I was focused on my grandkids. We’re all here to celebrate my parents’ fiftieth wedding anniversary,” he explained.

Jenn looked at his hand and noticed he was wearing a wedding ring, which begged the question, “So will your wife be joining you? I can’t help but notice your ring…”

Chris stiffened. “Sadly, no. She died three years ago.”

“Oh, I’m so sorry, Chris. I shouldn’t have asked. It’s none of my business,” Jenn apologized.

“Don’t be sorry. It was a fair question. Now it’s behind us, and we can move on,” he replied, as he took a sip of his drink.

The pair sat quietly chatting, getting to know each other and watching the sun set as they swung gently. Maybe it was the drinks, maybe it was the long day of travel, or maybe it was the company that was making Jenn feel flushed and giving her butterflies in her stomach. The air was definitely charged between them.

It was now totally dark, except for the lights wrapped around the base of the palm trees. Jenn was starting to fall asleep, so Chris offered to walk her back to her room. She graciously accepted, so he held her hand and walked with her through the winding paths to her building. He paused outside her door, and Jenn thought for a moment he was going to kiss her, but he gave her hand a squeeze before letting it go and smiled at her.

“Good night, Jenn,” he remarked. “I’ll probably see you around tomorrow!”

The thought made Jenn shiver with delight as she replied, “I hope so!”

She opened her door and slid in quickly.

The next morning, Jenn grabbed a quick breakfast and headed to the pool to claim a chair for the day. The resort’s activities staff were getting ready to play some ice-breaker games in the pool. Jenn declined the invitation to join but would have fun watching the other guests make fools of themselves. When it came time for the last game, they announced that the winner would get a “special prize”, so a few more curious guests went to join.

She heard him before she saw him - Chris joined the fun, and actually ended up winning the game, and the prize - a romantic dinner for two on the beach at sunset that evening. When he realized what the prize was, he tried to give it to his parents, but the staff made it clear that he had to use it himself. He got flustered, and returned to his seat on the other side of the pool.

With the activities finished for the morning, Jenn dove into the pool to cool off. Chris spied her instantly. He watched her gracefully swimming and felt himself starting to grow hard - embarrassingly hard. She was beautiful, with her dark blonde hair and crystal blue eyes. She filled out her bikini superbly with her hourglass figure. Chris adjusted his erection as best he could, and quickly stood and jumped in the pool..

He located Jenn and went over to chat with her. She was very happy to have this sexy, almost naked man paying attention to her. She was not impervious to the looks of other women around the pool, who were no doubt hoping to catch his attention. Last night’s chemistry was even stronger now.

Before long, Chris asked Jenn, “Would you like to be my date for dinner this evening? I won a romantic dinner for two on the beach…”

“I'd love to!” Jenn answered, a little too enthusiastically.

His smile said it all. Jenn was tingling as she smiled back at him.

As dinner time approached, Jenn nervously got ready for her date with Chris. She wore a soft, flowing white sundress, with her hair pulled back in a sexy bun, a few loose tendrils brushing her cheeks and neck. Chris arrived exactly on time, looking handsome in his linen pants and button-down shirt. He took her hand and spun her around, whistling as he twirled her.

“You look stunning!” he exclaimed.

“Thank you! You’re pretty handsome yourself!” Jenn replied. “Shall we go?”

The pair walked hand-in-hand to the beach where a table was all set up for them. They sat beside each other, backs to the resort, looking straight out over the ocean. The combination of the ocean breeze and the sexy man beside her, made Jenn shiver. Chris noticed and put his arm around her, pulling her in close to him. She laid her hand on his thigh as she snuggled into him. Jenn felt him tense, and quickly discovered the reason—he was hard!

The waiter arrived with their first course and poured them some champagne, before disappearing again.

“Here’s to first dates,” Chris offered as a toast, “and new beginnings! Cheers!”

“Cheers!” Jenn echoed, while staring into his dark brown eyes. There was a very powerful, unspoken sexual tension between them.

They managed to get through the rest of dinner, watching the sunset, chatting, flirting truly enjoying each other’s company. When it was time to leave, Chris helped her up, pulled her tight against him, and kissed her. It was a light, gentle kiss, that left them both breathless. Chris eventually, reluctantly, pulled away, making Jenn moan in protest. He looked at her, searching for something. She wasn’t sure what.

“Come back to my room with me,” he whispered.

Jenn bit her lip, held his gaze, and nodded. Chris grabbed her hand and started pulling her behind him as he nearly ran back through the trails to his room. They arrived giggling and breathless at his door. He swiped his key, and they fell through the door, hungry for each other.

Once behind closed doors, Chris stood in front of Jenn and slowly began sliding the straps of her sundress down over her shoulders, exposing her large breasts and pink puffy nipples. His breath caught as he took in the beautiful sight before him. He slid his hands lower, pushing the dress off her hips, and letting it pool on the floor. She was wearing only a white G string, which he could tell was already soaked through and transparent, showing off her cleanly shaved mound.

Those glorious breasts had Chris mesmerized. He raised his right hand to delicately brush the back of his fingers along her soft flesh. Jenn’s nipples hardened right in front of him. He grazed the back of his knuckles, over her tight buds, hearing her gasp, and feeling her shiver. Slowly, Chris lowered his head and sucked her left nipple into his mouth and heard Jenn groan with pleasure. Then he moved to the right one. Was he crazy, or did her nipples actually taste like strawberries?

Jenn started unbuttoning Chris’s shirt and slid it off his shoulders. She let her hands slide down his chest, over his nipples, past his belly button to his belt. She unbuckled it and moved to his pants, unfastening the hook and sliding down his zipper. She could feel his rigid cock pressing into her hands. She removed his pants and examined the bulge in his boxers. She traced her finger along its outline, making him shiver and moan.

She gently hooked her thumbs into the waistband of his boxers and shoved them down, letting his thick, eight-inch cock spring free and wobble. Jenn felt a gush of wetness trickle down her thighs. Chris slid her G-string down before leading her to the bed, and laying her on her back. He climbed on top of her, his cock nestling between her labia, teasing her as he began kissing her.

Passion and pure need soon took over. His cock teased her as he moved it over her clit and along her slit, until it slipped right into her slick vagina. Chris started thrusting and Jenn let out a low moan and began to rock her pelvis to push him deeper. She wrapped her legs around his waist, pulling him as tight as she could, and locking him there.

Chris broke their kiss, and raised himself higher, placing Jenn’s ankles on his shoulders, before resuming his powerful thrusts. He loved watching her breasts jiggle with his movements and loved watching the expression on her face as his cock hit against her cervix. He could tell she was nearing her climax, which, in turn, made him near his. She started to clamp down on his cock, her convulsions making him lose control. They shared an intense orgasm - Chris came deep inside of her before collapsing on top of her and kissing her deeply.

Eventually, their heart rates returned to normal, and Chris slipped out of Jenn and rolled to his side, leaving his arm across her chest. They were content, basking in the afterglow.

Finally, it was time for Jenn to leave. She did have her son waiting for her back in her room, after all. When she tried to get up, Chris stopped her.

“Please, stay with me,” he pleaded.

“I really shouldn’t...” Jenn replied. “Gabe will wonder…”

Chris’s lips silenced her. Consumed her. She was powerless to stop.

“Okay. Maybe just a few more minutes…” Jenn whispered breathlessly.