Jason And Jennas Date Night

Author Note: This is a 2025 Valentine's Day Contest Story, so please vote if you enjoy.

Jason and Jenna Kenney celebrated their 10th anniversary last fall. They were a typical, reasonably attractive married couple - both worked office jobs, they had two dogs and they owned a desirable home in the suburbs.

Jenna was a couple years younger than Jason. Her sex drive had always been a bit lighter than her husband's. She had never been overly adventurous when it comes to sex. Jason respected her boundaries, and for him, the weekly encounters they had were consistently hot and fulfilling. She would put on something sexy for him, they would kiss... yada yada yada... she came and then he did, too.

Their plan for this Valentine's Day was to celebrate with dinner in a nearby college town followed by sex back at home. While discussing their plans, Jason half jokingly suggested that Jenna flash him during their 45 minute drive back home from the restaurant.

"I bet you'd like that, you perv!" she chuckled, quickly changing the subject. Jenna didn't really indicate to her husband if she was open to the concept or not. While Jenna may not have been completely familiar with all of Jason's kinks, she was fully aware that he was very fond of upskirts.

As they got ready for their date, Jason noticed that Jenna chose an unusual outfit for their meal. The black cotton dress with small, white polka dots she wore was very typical for Jenna. It was the bulky, heather grey yoga pants that she wore underneath the dress that caused Jason to raise an eyebrow. Those seemed to be a bit out of place for her.

The drive to the restaurant was uneventful. The restaurant was very busy, given the holiday. Jason ordered a ribeye and Jenna had salmon. Neither the service, nor the food was particularly memorable - good or bad. More than anything, it was simply nice to get out. Like most married couples, they were busy and didn't grant themselves a date night often enough.

They paid the bill and got in the car to drive home.

Jason was in the driver's seat and his wife sat in the passenger's seat. As they pulled out of the parking garage, Jason kept an eye on Jenna, silently hoping, without much expectation, that maybe, just maybe, she would satiate his inner perv and go bottomless on the drive home.

She did not.

Internally, Jason shrugged. If there was any disappointment that Jason felt, it was only minor. Regardless if he was getting a show or not, he was certainly going to fuck his wife when they got home.

As they continued to drive back, Jenna grew quiet. Jason stole peeks at her, and was increasingly convinced that she seemed nervous. He got the sense that maybe, just maybe, she was planning something.

His intuition proved to be right.

When they took exit 14A off of the interstate, Jenna murmured "...don't crash the car..." and then with one quick, swift, confident motion, removed her grey tights and panites.

Jason was shocked, but tried his best to keep it cool. He assured her through a big smile that he wasn't going to crash the car.

Jenna pressed her back to the corner where the passenger seat and the car door fit. She positioned herself so her crotch was facing the driver and smiled.

She spread her legs open lewdly, and lifted the hem of her dress, showing off her freshly waxed pussy to him. Jason's cock immediately stiffened and his body went warm.

The highway exit was only 2 or 3 minutes away from their home. Wanting to extend his show, Jason asked her if it was okay if he took the long way home. Jenna said "Sure."

The alternate route home he mentioned was simply a back way through their neighborhood. It only extended their journey by another 2 or 3 minutes. However, getting off the main road was probably the right call, as Jason was dealing with a throbbing cock, a light head, and a deep desire to sneak as many glances at his wife's bald slit as he possibly could. All of these factors added up to someone who probably wasn't able to be the world's safest driver at the time.

The drive through the couple's neighborhood was littered with stop signs, and as a result, they quickly fell into a routine. When Jason came to a complete stop at a sign, he would look over. Jenna would open her creamy thighs and flash him for a few seconds. Then, she would close her legs and sit forward. Jason would reluctantly depress the gas pedal and inch closer to home.

During the last couple of stops, Jenna became a bit more brazen and escalated her show. After opening her legs, she reached down and with hands on both sides of her pussy lips, gently pulled them apart for her husband, opening up more of her beautiful folds for him. This is something she very well knew was a massive turn on for Jason.

The couple arrived at home and pulled the car into the garage. Jason asked her if he could take some photos. This wasn't unprecedented - it was something they had done during special occasions before, and Jenna agreed.

Jason closed the garage door, turned off the car, and then took out his phone. He snapped a couple of pics from the driver seat of his bottomless passenger, forever cementing the incredible view she gave him on the final moments of their drive home.

Jason put his phone down, leaned over the center console and passionately kissed his naughty wife. This quickly escalated into a lusty make out session. She placed her hand in his lap and began to massage his hot cock through his jeans. His left hand found her slit and he gently ran his fingers up and down her slick opening.

He broke their kiss and suggested that they head inside. She grabbed her shorts and panties and walked into the house. Jason was behind her, continuing to take photos. Jenna lifted up her skirt for him, flashing her ass for the camera as she stepped from the garage into their home.

The pair headed upstairs and into their master bedroom. If it was up to Jason, he would have (lovingly) thrown Jenna onto their bed and just fucked her in that black / white dotted dress.

But Jenna had other plans. She went into her walk-in closet and soon emerged in red, lacy lingerie that Jason hadn't seen her wear for him before.

It was a single piece, almost like a see through mini dress. It showed off her ample cleavage and the hem ended mid thigh. It likely came with a thong that she chose to ignore, keeping true to the pantiless / upskirt theme of this Valentine's night - a decision her husband fully applauded.

Jason snapped some more pics. First, a simple shot of her body in the sexy red outfit. Then, as she wrapped her arms around him, he lifted her skirt and got a shot of her from behind - her bare ass reflecting back at the camera via their ensuite mirror.

The married couple lustily made out some more and then Jason dropped to his knees. Jenna knew what he wanted. She lifted her skirt for him, so he could get a few pictures of her very aroused pussy. He took more than a few, including one where she spread her wet folds wide open for him.

As Jason then got off his knees, Jenna said "How about this?" She then slid the straps off her shoulders and popped her beautiful titties out of the lacy lingerie.

Jenna was blessed with an amazing set of tits. An impressive 'more-than-a-handful' C-cups with large, pink areolas, absolutely perfect in her husband's eyes. Jason took more photos of her in this pose, including one of her cupping her tits from underneath with a sexy smirk on her face.

After Jason got enough titty pics, his wife climbed onto their large bed. She laid on her back in the classic missionary position. She opened her legs up for her cameraman. Whenever Jason would make homemade porn, these modeling sessions always ended with him taking very explicit close-ups of her pussy - tonight would be no different.

Her normally tight pussy lips were blushing and separated, glistening with arousal. Jason asked her to place left hand into the shot - wanting to get a pic of her sparkly wedding ring right next to her cock hungry cunt.

She obliged, pulling on one side of her bald lips. With just a slight tug, she was wide open, looking almost like she had just been freshly fucked. She was incredibly wet, as evidenced by strands that connected horizontally in-between her sloppy folds.

By now, Jason's cock was throbbing so hard that it almost hurt. He tossed his phone on the bed and crawled on top of her. While her hand found his shaft, his hand found her messy folds. She pumped him as he slid two fingers inside her.

"Do you want my cock?" Jason said in a deep, lusty voice.

Jenna nodded. "mmmmmm...yes...fuck me..." she answered breathlessly.

Jason slid himself inside. Her dripping wet cunt easily accepted him and within seconds, he was pumping away inside her, hard and fast. Her wetness coated his shaft. As he continued to fuck her, his fingers found her clit.

"Come for me." Jason demanded, rubbing her pussy while he fucked her, something he knew always got her off.

"Oh, god... Give me that cock!" Jenna moaned.

"Come all over my cock."

"Fuck yes, I'm coming!"

While her legs shook, I knew Jason wasn't going to be able to hang on much longer. He groaned as he came, emptying his balls deep inside his wife, painting her insides white.

He collapsed onto her and gently kissed her neck as they both came down from their hard orgasms, his cum seeping out of her messy hole.

THE END

(Author note: If you made it this far, thank you! I truly hope you enjoyed it! I'm always looking for feedback, if you have a thought or two, please share with a comment or a note. Thanks again!)