Offsite Meeting Fantasy

My co-worker and I are in long-term committed relationships with partners who do not provide us with enough attention from a sexual fulfillment standpoint. We both love our partners and do not have intentions to leave existing relationships. Despite loving our partners, we have both found comfort and interest in one another from a strictly sexual standpoint; neither of us feel emotional connection or desire towards one another.

While most would say that the first time, we shared intimate desires and encounters was the moment it became not okay, in effort to remove the guilty feeling (there's plenty) we have agreed that performing sexual acts would be considered "crossing the line".

Consequently, over the course of months, we have enjoyed exchanging our fantasies with each other and as a result we have accumulated these short stories.

Sometime in the future, it was a much better time financially for the Company. So much so, that the CEO thought it would be a great idea to send some of his upper level and middle level managers to a leadership retreat. The question was: where should this take place? The CEO's first thought was that it should be an on-site retreat, perhaps at the hotel down the street in scenic suburbia. But after some feedback from his favorite and indispensable manager, it occurred to him that to foster better company culture the retreat should occur somewhere remote. Fortunately, the CEO's dad knew a guy that was the son of a guy who was in a real estate venture that also ran a leadership retreat at the in sunny La Jolla CA. More importantly, they offered a friends and family discount for this retreat. The second question was, which managers should be invited to go to the leadership conference? The CEO neatly cut up small squares of paper and wrote manager names on the squares. He then placed the squares inside of a bowl and had his favorite admin draw 5 names out of the bowl. Upon review of the 5 names drawn, the CEO discarded 2 names, because those managers had failed to live up to his high expectations recently, and subjectively relaced those names with 2 other names off the top of his head. Very quickly the CEO had his favorite admin book flights and rooms for the managers selected at the at the resort and conference hotel to which he received the friends and family discount.

Dan and Jessica were two of the lucky managers who were selected for the retreat. This was a bit troubling for each of them because they have found it nearly impossible to resist each other at work, and the prospect of being away from their regular lives and being around one another for several days in a topic locale was a recipe for disaster. That said, both Dan and Jessica knew how disappointed the CEO would get if one or both of them withdrew from the leadership conference. Consequentially, both reluctantly accepted the offer from the CEO to attend the conference.

The conference was scheduled in January, which was a great time to get away from the cold and snow of the Midwest. Unfortunately, due to admin mistaking PM flights for AM, both Dan and Jessica ended up on a 6 AM red-eye flight to San Diego. Dan and Jessica had been texting the night before and decided to meet up at the gate in Terminal 1 of the large city airport. Dan got to the gate first, but didn't see Jessica.

"Where are you at?" Dan texted Jessica.

"The bar, duh." Jessica texted back.

"It's 5.30 AM." Dan wrote back. "There is a bar open?"

"Yeah. This one. It's over by the Hudson News on the C side of Terminal 1." Jessica responded.

Dan was standing at gate B9. Fortunately, it was right next to the underground tunnel from the B side to the C side. Once Dan got to the other side, he went about scanning the terminal for a bar. There was one right in front of him, and there was Jessica sipping on a dirty martini.

"Hi there." Dan said walking up to Jessica. "The gate is on the other side, you know."

"Yeah, but the bar is over here," Jessica said holding her drink up to toast no one in particular.

"We should get back to the gate," Dan said motioning with his head towards the tunnel to the B side.

"Let me finish my drink," Jessica said tipping the glass up to her lips and gulping the drink down. "There, all good. She already ran my card."

"Fantastic," Dan said helping Jessica out of the seat at the bar. "You going to be good to walk over to the gate?"

"I'm fine. I just don't like flying. I needed to take the edge off," Jessica said as she walking briskly with Dan.

They made it back to the gate just as group 1 was boarding. Dan looked at his boarding pass and saw he was in group 2. "What group are you?" Dan asked Jessica.

"Group 3," Jessica said.

"I thought she scheduled all of us the same," Dan said with disbelief.

"You guessed wrong, sir. Must be nice having a dick. You get everything, even priority boarding."

"Admin is not that good. She didn't do this on purpose," Dan said while rolling his eyes.

Eventually both Dan and Jessica boarded the flight. The ended up seated in the same row in coach, but with one seat between them in 3 by 3 seat arrangement of the Boeing 757. Dan got the window seat and Jessica got the aisle.

"Do you think they would mind if I moved over?" Jessica asked.

"Probably not," Dan said. "But you may want to ask."

Jessica pushed the flight attendant call button. The flight attendant looked quite tired as she came walking up the aisle. "Does it matter if I move over? We have work stuff we need to talk about" Jessica asked trying to sound as nice as possible.

"If no one else shows up, the seat is yours." The flight attendant said flatly.

After what seemed like a long time, the flight attendants closed the doors and the seat was still empty. Jessica took that queue and switched seats. Soon, the plane pushed back from the gate and taxiing out to the runway to take off.

"Fuck I hate planes," Jessica said gritting her teeth.

Dan offered his hand to Jessica and she gripped it tightly.

The plane took off with no issues and was soon climbing to the 30,000-foot cruising altitude.

Jessica was feeling the effects of the martinis she had earlier and was getting a bit tired. "Hey," she said as she got Dan's attention. "I'm going to close my eyes. Please wake me up if I snore."

Dan shook his head in agreement and went back to reading a magazine.

Jessica struggled to find a comfortable spot to nap. She eventually ended up resting against Dan's shoulder. Dan didn't mind. He enjoyed the feeling of her resting against him.

A couple of hours later, Jessica finally stirred. "Where are we?" She asked while stretching her back.

Dan tapped the back of seat infotainment screen to see where the plane was at. "Somewhere over Colorado."

"Oh. How much time do we have?" Jessica asked leaning closer to Dan.

"Looks like it will be another an hour and a half," Dan said.

"Well, what should we do?" Jessica said snuggling her face up to Dan.

Dan knew what she wanted. He had been around her enough to know she gets horny when she is around him for long periods of time. Months of discrete 'lunch meetings' in a parking lot well away from the prying eyes of work had conditioned both of them to get hot when they were around each other. So much so, they found it nearly impossible to sit next to each other in work meetings.

"Why don't you get your coat?" Dan whispered.

"Why don't I get your coat?" Jessica whispered back as she stood up and got Dan's coat from the overhead bin.

Jessica brought Dan's coat down over the both of them. She then looked around to see if anyone was watching. It looked like nearly everyone was still asleep. Acting nonchalant, Jessica slipped her hand below the coat and worked her hand up Dan's thigh. Dan squirmed a bit as Jessica's hand reached for his cock. He was quickly getting hard as Jessica ran her hand up and down his cock outside of his pants. While she was working on his cock, Jessica leaned in close to Dan and they kissed passionately. Dan and Jessica had recently crossed the threshold and started kissing in their 'lunch meetings', which they both enjoyed immensely. Here, they were both conscious the sleeping passengers on the plane and didn't continue too long. Dan's cock was very hard at this point as Jessica continued to stroke it. She pulled her hand up to his belt and Dan, knowing the signal, discreetly undid his belt and pants to pull his cock out.

"You can't suck it, there are too many eyes watching," Dan whispered to Jessica.

Jessica stuck out her lower lip.

While Jessica was stroking Dan's cock, Dan started to work his hand up Jessica's leg. She was wearing a very soft pair of jeans which clung to her legs very closely. Jessica opened up her legs in her seat and Dan moved his hand to her crotch. It was very warm and felt damp. Dan could hear her breathing intensify as he moved his hand across her crotch. Dan moved his hand to undo her pants but stopped to get Jessica's consent.

"Yes, please," Jessica whispered.

Dan undid Jessica's pants, and slipped is fingers under her panties. Her pussy was extremely wet as he ran his two fingers across the outside and her clit. Jessica's rubbing of Dan's cock intensified slightly as Dan rubbed her pussy.

"Put your fingers inside," Jessica whispered.

Dan first stuck his first finger deep into her pussy. Then, he slid his middle finger over deep into her pussy. Jessica shuddered as Dan stuck his fingers deep inside of her. Dan started moving his fingers in and out of wet pussy.

Suddenly there was an announcement. "Ladies and Gentlemen, I hate to wake you up but the Captain and I wanted to let you know we are on approach to San Diego International. The flight attendants will be coming around to collect trash. Please bring your seat backs forward and place your tray tables in the upright locked position. Currently its 9:30 in the morning local time and it looks like it will be a beautiful day currently 50 degrees with a high of 72..."

Dan and Jessica snapped back to reality and quickly stopped what they were doing and zipped and buttoned their pants back up. They exchanged smirks as they looked around to see the passengers starting to wake up.

Thirty minutes later Dan and Jessica emerged from the gate into the terminal and found their way downstairs to baggage claim. After successfully locating their bags, they walked out into the warmth and sunshine of a beautiful southern California day to wait for their ride share. This was a start contrast to the cold and snow they had just left back at home. Also, Dan hated not having a car, but he knew the CEO would never reimburse him for the cost of a rental car.

After a scenic ride up the coast to La Jolla, Dan and Jessica arrived at the resort and conference hotel. Dan looked at his watch, it was 11 AM.

"We are going to have an issue checking in. They booked the flight too early and the check in time isn't probably until 3 PM." Dan said as they approached the check-in desk. "Let's see what we can do."

Indeed, it was too early to check in. Another issue was the conference was over-booked and rooms were hard to come by already.

"We have three additional people coming on a later flight for the conference," Jessica told the woman at the front desk. "Are they going to have rooms? Here are their names," Jessica slid her phone across the desk with an email up showing the employees' names.

"It looks like they have been assigned to rooms already. For some reason, the two of you never got assigned," the front desk woman said squinting at the computer screen. "Let me go talk to my manager and see what we can do. You clearly have a reservation and I really don't want to turn you away."

A couple of minutes later, a striking woman walked out of the back office and approached the desk. She clearly has some work done because her breasts were quite large and round. She was tall and her muscular legs were very visible under her skirt. Dan and Jessica exchanged raised eyebrow glances as she walked up. "Hi, I'm Katie, I'm the day manager for the hotel. Jennifer let me know about the situation. Here is what we can do. We don't have the regular rooms you originally booked; however, we have a beach villa we can give the two of you. It's a two bedroom with two bathrooms but a common living room and kitchen. It's normally something that a family would use, and we have it available because of a cancellation. We can give it to you at the same cost of the original reservation, because the villas don't have a tendency to be used this time of year. Is this something you want to do?"

Dan thought through the situation. "It's not ideal, but I would rather not have to have us stay at another hotel and then have to commute over here for the conference. Can you set this up to bill us separately as if we had separate rooms?"

"Yes, actually that is the way our accounting system has to do it, since that was how it was set up in the first place. It's not that great of a system." Kate smiled.

Dan and Jessica looked at each other plotting their next move.

"You good with that, Dan?" Jessica said.

"I think we can make this arrangement work." Dan said thoughtfully.

"Great," said Kate her fingers flying on the keyboard. "Let me just update the room assignment. Here are your cards. The villa is located on the back of the property near the beach. If you go out these doors," Kate said motioning down the hallway, her breasts bouncing as she pointed, "and go straight back, then take a left."

Dan and Jessica both found themselves lingering too long on Kates ample breasts. They snapped out of it at the same time. "Thank you, Kate, we really appreciate you helping us out." Jessica said smiling.

The villa was amazing. The room had two bedrooms, two bathrooms, a full-sized kitchen, and a living room that opened onto a patio which overlooked the rocky shore of the Pacific.

"This will do nicely," Dan said putting his hand on Jessica's back.

Jessica smiled and looked at Dan. "It's a little better than sitting in your car in a parking lot."

Dan and Jessica both sat down on the sectional. "What ever shall we do with ourselves?" Dan said getting closer to Jessica.

"Maybe continue what we started on the plane," Jessica said leaning into Dan.

Dan and Jessica started making out, each putting their hands behind each other's head. Thrusting their tongues into each other's mouth. Dan started putting his hands down Jessica's shirt and rubbing her hard nipples. Jessica put her hands in Dan's crotch and started feeling his rapidly hardening dick.

Jessica started at Dan's belt, Dan undid his belt and took down his pants and underwear exposing his cock. Jessica started rubbing it while Dan moved his hand to between Jessica's legs. Jessica took the initiative and undid her pants leaving her underwear between Dan's hand and her pussy. Dan slipped his hand down Jessica's underwear and put his fingers on the outside of her pussy. He moved his fingers up and down feeling how wet it was and playing with her clit. Jessica's beathing started to intensify as Dan played with her. She couldn't take much more so she bent over and put Dan's long, hard cock in her mouth. Dan moved his hand to Jessica's sweet ass, grabbing it as she sucked his cock. Her mouth felt wonderful on his cock as she moved it in and out. She started using some teeth which made Dan really hot.

Eventually, Dan started to feel like he was going to bust. "I'm going to cum."

"That's fine," Jessica said continuing to suck his cock.

The orgasm washed over Dan as he cum into Jessica's mouth. Jessica swallowed his cum and kept sucking as Dan shuddered with ecstasy. As Dan finished, Jessica pulled off his cock and started looking for something to drink. Thankfully, the fridge was stocked with bottles of water.

Dan laughed as he put his cock back in his pants. "You know, we don't have to limit ourselves to just the stuff that we normally do in the car. We could take the next step in this experience and actually sleep together."

"This could have happened a long time ago if we would have actually pulled off the 'work from hotel' plan instead of just talked about it," Jessica shot back as she used a paper towel to clean the sides of her mouth.

"We have only been talking about it for a couple of months, and we didn't want to do it during holiday time," Dan furrowed his brow.

"All I hear are excuses," Jessica retorted.

"You are such a wonderful person," Dan smiled.

"I know, I hear that all the time," Jessica said after drinking more water. "How about we go downstairs and get a drink at the bar?"

"That sounds like a plan," Dan said.

Several minutes later Dan and Jessica were sitting at the hotel bar. It was a lovely location on the back-side of the building overlooking the same rocky cliffs over the Pacific Ocean. The bar opened up onto a terrace and the gentle ocean breezes could be felt throughout. It was a warm evening which was atypical for the time of year. Jessica had ordered a martini and Dan was waiting on a margarita.

"Here you two go," a familiar voice said as she slid the drinks towards Dan and Jessica.

Dan and Jessica looked up to see Kate behind the bar.

"You tend bar in addition to managing the hotel?" Jessica asked.

"One of the girls called in this evening. I am just covering," Kate said smiling at Jessica. "So, tell me a little more about you two."

"We have worked together for several months. Due to the nature of our positions in the company, we have a tendency to work on the same projects. We know each other quite well," Dan said looking into Jessica's eyes.

"I can see the way you look at each other," Kate said smiling. "There is more to that, isn't there?"

"We are both married, just not to each other. We enjoy each other's company, but we try to keep it light between the two of us," Jessica smiled looking back at Dan.

"Absolutely no judgement from me," Kate said brushing her hair back. "I sometimes have some fun with the people that work here. Life is too short, it's fun to meet and do things with new people."

Dan and Jessica smiled at this comment. Dan moved his hand to Jessica's.

"How is the villa working out for you two?" Kate asked.

"It's absolutely gorgeous," Jessica said.

"It is one of the best rooms I have ever stayed in," Dan agreed.

"Great. I am glad that worked out for you," Kate smiled. "You know, I can come by later and fully explain the features of the villa, if you would like. I get off in a couple of hours."

"I would really enjoy that," Jessica said drinking her martini.

"It's a date, I will see you then," Kate said walking off.

"It's a date?" Dan said to Jessica. "Did she just pick you up?"

"It's been a while since I've swung that way. But she is super fucking hot," Jessica said eyes widening.

"I know, she's really attractive. I wonder what 'features' she is going to explain," Dan asked.

"Perhaps she will show us her features. Her tits are amazing," Kate sighed.

"Yes, yes they are," Dan said.

Jessica and Dan finished their drinks and took a walk along the coastline on their way back to their villa. The evening had an amazing feel to it and they couldn't help but hold hands as they walked. Eventually, they ended up back at the villa and went inside. A couple hours later there was a knock at the door.

"Hi Kate," Jessica said welcoming the beautiful woman inside.

"Hi there. Are you two enjoying your evening?" Kate asked.

"Of course," Dan smiled. "What was it that you were going to explain?"

"Well... let's me think. There is a great deal of history to this place," Kate started. Over the next hours, Kate, Jessica, and Dan talked about the villa and many other things. Jessica found the vodka that was in the cabinet above the sink and was continuing to pour drinks for her and Kate. Dan was stuck to drinking the scotch that he found.