Jenn and Josh Pt. 04 – Finale


Life continued on for Jennifer and Josh.

Nearly a year earlier, the older Jenn and younger Josh had shared a one night stand. Weeks after that initial night together, they went on a proper date. Both encounters resulted in nights of surprisingly great sex.

In the two months that followed, they went on a few additional dates. Those had not culminated in sex, nor had they shared the same supercharged energy.

Aside from their sexual compatibility, the two shared a few common threads- one was that neither desired a relationship with the other.

Their casual dating was fun, but wasn’t going anywhere. Jenn decided she was moving on from relationships. Her ex had badly emotionally scarred her. She was ready to move on and keep things simple for the rest or her life. If that meant being alone or indulging the occasional fling, so be it.

Jenn had recently celebrated her 53rd Birthday. The last of her four university-age kids was still living at home. After her recent divorce, Jenn had rediscovered fitness. A former collegiate athlete with time in the Navy, she was no stranger to being fit. But she now found solace in her post-divorce life among the steel and repetitions.

The obvious bonus was her fitness did great things for her figure. Sandy blonde, tan, trim and muscular, she turned heads in a way she had not previously been able to, even three decades earlier.

At 26, Josh was finding himself as a young professional. He’d recently moved to the Gulf Coast for a work opportunity. His long-term girlfriend had not followed him.

Josh was tall, fit and handsome. He kept his hair cut short and his arms and shoulders inked with a few tattoos. A bit of a loner, his only regular outlet was the gym. He was a night gym-goer, attending after his long hours.

Josh’s work kept him engaged with long hours both on and offshore. He was compensated handsomely and had moved from his shitty apartment into his own house. He’d gotten both a new car and a hobby boat, which he rarely found time to use.

Since meeting Jenn, he’d casually dated a fair share of women. None of them were sticking around long. He loved his work too much, they’d claim.

Jenn guessed that he’d be a great catch for the woman lucky enough to end up with him. Josh was young and still somewhat naive.

Fitness was their other common thread. Both avid exercise buffs, Jenn and Josh worked out at the same Crossfit Box gym. Together, they could have been in a advertisement for the place. However, as they kept incompatible schedules, the two had not seen each other there in months.

Their third common thread: the two still craved each other.

Jenn yearned to see her one-time fling again. She occasionally daydreamed about him. The mature, handsome younger guy who’d been generous.

She hadn’t seen him at her before-dawn classes. She remembered that he worked days and preferred to work out at night. Jenn had to remember that she had set the boundaries for their relationship- strictly no strings attached.

Josh too remembered his time with Jenn fondly- the sexy, hard-bodied woman who took what she wanted. He loved her confidence outside and inside the bedroom. She was a breath of fresh air from the women he’d been dating.

Maybe he would call her, he kept telling himself. He too, had to remind himself that Jenn had set the terms for them- no strings attached. Josh assumed a hot older woman like Jenn would’ve gotten herself a partner by now.

The two were destined to reunite.


In the Spring, Jenn was invited to a Masquerade Ball Charitable Fundraiser, by her friend Kate. Similar to Jenn, Kate had gone through a divorce twelve months earlier, at 46.

Jenn had been a friend and mentor to Kate- she’d been there emotionally for her. Kate followed Jenn to the gym- a new healthy release for her.

The night of the Ball, Jenn wore a sparkling knee-length red dress and high heels. Typically humble, Jenn had to admit she looked fantastic in her own body.

At 53 and after four children, she looked like most women in their twenties. She was proud of the results she had achieved.

Kate picked Jenn up from her house in her Toyota SUV. Kate wore a sexy little black dress. Her blonde highlighted hair was curled- she looked just as glamorous as Jenn, albeit a tad sluttier, she thought. Her thigh-length dress barely concealed her breasts. Jenn knew that Kate had paid for breast enhancement after her divorce.

“Hey girl!”

“Oh, my god, you look amazing!”

“Are you not bringing a date?” Kate asked as Jenn buckled into the front seat.

“No way” Jenn replied. She simply didn’t want to go through the trouble. She did, after all, have a big workout the next morning.

“I’m meeting Rob there,” Kate volunteered.


Jenn didn’t know a Rob.

“Yeah, hot, huh?” Kate flashed a photo of him on her phone. Jenn hadn’t asked to see one.

Jenn laughed and secretly rolled her eyes. Kate seemed somewhat desperate. In the twelve months since divorce, she’d gone through escort gaziantep bayan numaraları twice as many partners.

Kate soon parked at the upscale hotel valet. She and Jenn donned their masks and entered the ballroom.

The hotel ballroom was enormous. It featured multiple cash bars, a dance floor, several round tables and a table for a silent auction. Imbibed, masked revelers would bid on expensive spa treatments, art and weekend getaway packages- all in the name of a noteworthy charity. A few hundred party goers were in attendance.

Jenn and Kate made their way through the crowded ballroom and located the cash bar, where she was expecting to meet her date.

“Hey, are you Kate?” a young man asked. He wore a mask and a simple unbuttoned white shirt over dark jeans.

“Yes!” Kate answered.

“I’m Rob,” he introduced himself with a smile. Rob was Jenn’s height, dark and handsome.

“Hi, Rob,” Jenn shook his hand. His soft hands and smile suggested he figured himself more charming than he actually was.

“Wow Kate, your friend is stunning,” Rob commented.

“Thanks, but don’t get any ideas, you’re here with me! After all she’s in love with her gym,” Kate retorted.

Jenn smiled. Said nothing. Rob and Kate continued to make small talk.

Jenn already decided she didn’t like this guy. Nonetheless, Jenn was happy for her friend. She certainly recognized the spot she’d been in- lonely and craving attention. She withdrew and allowed the two to catch up.

Fuck this, I’m going to get a drink Jenn thought to herself.

Jenn ordered a double vodka and tonic from the open bar. Kate had disappeared with Rob.

Jenn was already bored. She decided she’d get a little drunk, let Kate go fuck Rob and carry on with life.

She shrugged off some leering gazes from a group of fat men her age, as she made her way towards the silent auction table, drink in hand.


Josh scanned the ballroom. He sipped a whiskey on the rocks, making small talk with a group of masked guys and their wives or dates, all whom he barely knew. His own blind date, Sara, was a no-show.

Josh was invited to the Masquerade Ball Fundraiser by a friend in town. He’d offered up his ticket to Josh for free ticket after he learned he’d be unable to attend.

These sort of things normally didn’t hold Josh’s interest. Josh acquiesced when he learned his friend was trying to set him up with a Sara, a mutual friend.

Sara was a former SEC cheerleader, she had a great reputation and was successful in real estate at only 28. Not to mention she was single. A solid resume and a naturally good choice. Josh was excited to meet her.

Josh dressed in a dark navy suit and reluctantly donned an eye mask for the Ball.

An hour into the event, and Sara had never showed up. Josh texted his friend, who left all of his messages unanswered.

Fuck it Josh thought.I’m going to get another whiskey.

He excused himself from the circle of polite acquaintances and their dates.

Josh pushed around packs of Ball attendees, as he headed towards the front of the ballroom, where the open bar was located. He’d have to cross the ballroom, past the silent auction table.

An older woman in a black dress caught his eye. She had huge, obviously fake breasts which were barely contained. A young man, maybe about his age followed, holding her hand. Josh thoughts wandered to Jenn, his own fling with a stunning older woman.

Good for you, man. Josh said to himself.

As he approached the silent auction table, Josh stopped dead in his tracks.

Josh saw a fit, tan, older woman in a sparkling red dress. He knew it was unmistakably Jenn. Toned legs and powerful arms were a drop dead giveaway.

Before he could think, Jenn met his eye. She smiled, began walking toward him. Josh’s stomach dropped.

The night had taken a turn.


“Hi, Jenn”

“Hi, Josh”

Jenn hugged Josh. She planted a kiss on his cheek.

“So…” Josh laughed nervously.

“How have you been?” Jenn asked.

Before Josh could answer, the big-breasted blonde and her boy toy came up to Jenn and Josh.

“Well, hi, you!” Kate opened.

“Josh, this is my friend Kate” Jenn offered. “She also goes to our gym.”

“Hi, Kate.” Josh shook her hand. He tried not to stare at her tits.

“And this is Rob,” Jenn made the introduction.

Josh and Rob shared a firm, quick handshake.

“He’s my friend,” Kate said. She didn’t volunteer that they’d only met in person a few minutes ago.

“So, we’re dying to go dance now,” Kate stated. Rob smiled. Jenn said that she wouldn’t be joining, but told her friend to have fun.

With that, Kate led Rob towards the dance floor.

They shared a glance and a moment. Neither was ready to leave.

“So, what’s the story there?” Josh chuckled.

“Don’t ask,” Jenn stated, a wry grin on her face.

“Where’s your date?” Josh asked Jenn.

“Single tonight,” Jenn escort bayan gaziantep reklamları said, the faint smile across her lips growing. She had missed him- she was confident she could get Josh again.

“So, I’m empty” Josh said, clinking around the ice in his glads. ” Let’s get a drink.”

“Absolutely,” Jenn agreed.

Over the next drink, Jenn and Josh caught up. Their conversation was natural and light. They caught up on the gym, Josh’s new boat, work and their dating lives, or lack thereof.

“So are you…” Jenn pried.

“I’m single tonight.”

“Good answer,” Jenn winked at Josh.

“I need to elaborate, I was meeting someone, but got stood up,” Josh confessed.

“Aww. Well, I can take care of you.”

“I’m going to hold you to it.”

“How about another round?” Jenn held up her empty glass.

Several rounds of drinks later, Jenn and Josh were tipsy. Both hadn’t realized how much they’d still wanted the other. Their desire had smoldered, but not disappeared.

“Do you want to dance?” asked Jenn.

“Sure, but you know I’m not much of a dancer.”

“That’s fine.”

Hand in hand, they walked to the dance floor. As they arrived, the song changed to a slow song. Many of the revelers had left, and only pairs remained.

Jenn and Josh embraced, pulling their warm, firm bodies together. Josh rested a hand on her muscled, firm lower back and hip. The two slowly swayed to the music. He started to get aroused at the mere suggestion of her tight body, pressed against his.

“Do you want to get out of here?” Josh whispered into Jenn’s ear.

“One last time” he added.

“Yes.” Jenn agreed insistently.

About fucking time you asked Jenn thought.

Jenn planted a kiss on Josh’s cheek. Then, she licked her warm tongue across his neck.

“I’m very excited to fuck you again” Jenn said in a low whisper.

Josh smiled. He gripped her taut hip. He had missed her directness.


Shortly after their slow dance, Jenn located her friend Kate with Josh’s assistance. Josh was helpful and respectful. He seemed to cue in on Jenn’s minor annoyance with her friend.

They found Kate and Rob seated at a table. One of each of their hands wasn’t visible. Jenn suspected they were already giving each other hand jobs under the table.

Jenn explained that she was ready to leave- she was going to take Josh home. Since her kids were out for the night, Jenn suggested Kate use her spare bedroom.

She flatly told Rob he could come back to her house, but couldn’t spend the night. He agreed. Josh thought that in Rob’s shoes, he too would have agreed to those terms.

Kate too, was eager to collect her boy toy and return to a more intimate setting.

The Uber ride back to Jenn’s house was raucous. Two tipsy ‘cougars’ and two young men that couldn’t seem to keep their hands off each other. Surely the driver had seen worse.


The four now stood in Jenn’s living room, listening to music and carrying on a small after party. After they’d arrived at the house, Jenn had offered up a round of cocktails. Simply an old bottle of rum she found in the pantry mixed with Coca-Cola.

It wasn’t long before sexual energy overtook the two couples.

Jenn and Josh embraced, kissing urgently. Josh quickly unbuttoned and removed his shirt. Jenn’s hands caressed his broad, muscled chest.

Kate began making out with Rob. Within a minute, he’d stripped to his boxer shorts.

Jenn shot Josh a mischievous look. She had her share of sexual adventure in her youth. Jenn wanted to see how far Kate and Rob would go with another couple in the room. It felt wild and turned her on.

Without a word, Josh sat on the couch, Jenn straddling him. She hiked up her red dress, exposing tiny thong panties. Josh’s strong hands grasped the flesh of her ass. They continued to make out.

Next to them on the couch, Kate and Rob were a mirrored image.

Jenn stood, dropping her dress to the floor. All she wore was her thong and her heels. Her body was toned and tanned. Her small breasts exposed, her nipples hardened. Josh took a moment to admire her body.

Josh removed his suit pants, down to his boxer briefs. Jenn returned to Josh’s lap. This time, she writhed on top of him, rubbing herself against Josh’s erection.

Kate stood and unzipped her own black dress, finally revealing those enormous round breasts. She kicked off her stilettos. Underneath, she wore black panties, which she quickly removed.

Rob removed his boxers and began to stroke his own exposed cock as Kate undressed. Kate smiled. She pulled back her hair and got to her knees in front of Rob. She took his cock into her mouth and began to work him. Rob moaned in ecstasy.

Jenn leaned forward. Josh caressed her breasts, taking each of her firm nipples into his mouth.

Meanwhile, Kate had wasted no time and straddled Rob. She lowered herself onto his lap, guiding his dick inside her. She began gaziantep escort kız telefonları to slowly bounce up and down.

Rob grunted.

“Yes, yes, yes,” Kate moaned.

Jenn considered staying and fucking in front of Kate, but was all too eager to have Josh to herself. She knew she’d be able to come more quickly with only Josh.

“Lets get out of her and give them some privacy,” Jenn soon whispered into Josh’s ear. He felt her warm breath in his ear. Her hand easily found Josh’s erection and gave him a gentle squeeze.

“Okay,” Josh agreed. There was no way he would have said no.

Turned on by the scene unfolding, Josh was ready to consume her. He placed his hands under Jenn’s thighs and lifted her. She wrapped her strong thighs around his torso, while he carried her towards her bedroom.

“Bye!” Jenn said to Kate. She waved with one hand. Kate was busy bouncing on Rob’s dick, so she doubted they had even noticed.


Josh carried Jenn to the bedroom. He shut the door, walked across the room and pressed Jenn against the wall. She shuddered a bit in anticipation. They kissed deeply.

“This is our last time. We’ve got to stop doing this. We aren’t dating.” Jenn said.

“I know.” Josh agreed. They kissed again. He felt her warmth, the sweet taste of rum in her mouth.

“This is probably not what’s best for us.” Jenn continued.

They kissed again, this time more deeply.

“Then let’s make a bad decision together.”

“I was hoping for it. We are kind of far along already and I really want you to fuck me” Jenn quipped. She craved him, if only for one more time.

They kissed again. Jenn pulled him close, her tongue darting into his mouth.

Josh abruptly picked Jenn up from her thighs, crossed the room and gently tossed her on the king sized bed. She laughed playfully.

He hooked his thumbs under the black thong and tossed the tiny piece of underwear aside. Without missing a beat, he started to lick and kiss Jenn’s most sensitive parts.

“I fucking needed this,” muttered Jenn. Josh’s warm tongue slid across her lips, teasing her clit at first. Soon, he found a pace which was sure to make Jenn come. She found her breasts with her hands, involuntarily playing with her own nipples. Her wetness became a puddle.

“Don’t stop!” Jenn begged. He didn’t.

Josh slid a finger into her, while his tongue lapped at her clit. Jenn melted into the bed. She bucked her hips and grasped onto the bed sheets.

Fuck, Jenn thought. She was so close to coming.

As he licked and worked Jenn, Josh noticed she’d never removed her high heels. They’d probably leave scratches across his wide shoulders. He didn’t care.

“Oh. God. Fuck!” Jenn was nearly screaming. Josh continued to lick at her, while his fingers fucked her. She grabbed a handful of Josh’s short hair.

Jenn came. Her hips bucked and writhed with the pulse of her orgasm. She lay there, breathing heavily.

“Wow,” was all Jenn managed.

“Fuck, you’re incredible,” Josh replied, kissing her thighs.

She noticed she’d left her high heels on. She was certain they’d been digging into his shoulders as he ate her out.

“Sorry about that,” she breathed.

“No worries,” Josh shrugged.

“I want to take care of you,” Jenn said, pushing her sandy blonde hair out of her face. She finally removed her heels.

“Please do,” Josh replied. He knew what that meant- it was Jenn’s turn to give him oral. He lay face up on the bed and took off his underwear.

Jenn made eye contact with Josh. As she did so, she slid her wet tongue up and down the underside of his shaft.

Josh groaned. Jenn quickly engulfed his length into her mouth. She grasped his balls and created gentle suction around his shaft.

She paused to tease him by licking around the tip of his erect cock. Jenn gave him quite a show, licking around his tip, flicking her tongue like he’d just done to her. While she did so, she watched his eyes roll back. His balls tightened. Jenn felt smug- she was enjoying watching this sexy man on the cusp.

Josh grabbed a palm full of her hair, pulling it into a hasty ponytail.

He looked her in the eyes. Jenn continued with him in her mouth.

“Do you want to fuck my face?” Jenn asked. She was a little drunk and horny for this man who just made her cum. She couldn’t believe her own mouth.

“I want to fuck you.”

“Okay, baby. But it’s my turn.”

Jenn sat up and positioned herself over Josh. She gracefully lowered herself onto him, letting his large erection fill her. He easily slid into her- Jenn was still aroused by the foreplay and her orgasm from earlier.

She started to work into her own pleasurable rhythm. Josh’s strong hands caressed her small breasts and finally came to a rest around her tiny waist.

“You remember how I like it?” Jenn soon asked. Jenn felt herself nearing another orgasm, but was ready for Josh to fuck her- and hard.

What was the fun of fucking this fit, hot younger guy, if he isn’t going to take me? Jenn asked herself.

Josh did remember. During their past encounter, Jenn particularly enjoyed being taken by Josh from behind. He said nothing, only smiled.

She turned, got to her knees on all fours, pushing her tight round ass into the air.

Josh knelt behind Jenn. He guided himself to Jenn- again, easily inserting himself into her swollen, slick pussy. He grasped her hips and quickly built a rhythm, plunging deep inside her.

Life continued on for Jennifer and Josh. Nearly a year earlier, the older Jenn and younger Josh had shared a one night stand. Weeks after that initial night together, they went on a proper date. Both encounters resulted in nights of surprisingly great sex. In the two months that followed, they went on a few…

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