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Anna's Nude Holiday

This is an absolutely ridiculous short story that's been rattling around in my brain. I thought this would be a good time to share with everyone since I'm still working away on the next installment of The Contract and it's taking longer than expected.

Enjoy!

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"Congratulations! Anna on twenty years with the Runestone International," the owner of the company Jack Caswell said raising a glass of champagne. Everyone in the room echoing his sentiments.

Today was Anna Harrison's 20-year anniversary with the company. Whenever someone hit this huge milestone the entire company celebrated.

"Thank you everyone for making this such an amazing place to work," Anna said looking around the room.

"As you are aware Anna, when one of us makes it to the 20-year mark with us they are granted the gift of their choosing." Jack said handing her a notepad and pen. "Please write down one outrageous thing that you want and one more reasonable thing. We'll do our best on the first one, but no promises."

Anna took the notepad from Jack and quickly scribbled down her wishes. This was something she'd thought about for the last five years when she realized she was going to make the milestone. Many of the employees either retired or used the company as a steppingstone in their careers before hitting 20 years so it was a big deal when someone did. Anna was hired right out of high school at 18 years old and immediately fell in love with the place. The people and culture were everything she imagined an office would be like. Hearing horror stories from her friends at other companies only solidified her position.

"Interesting," Jack said reading the notepad, "I'm not sure if this is possible, but I will see what I can do."

The party was successful as the free food and flowing alcohol tended to make people happy. Anna was bombarded throughout the afternoon with questions about what she asked for, but she wanted to keep it under wraps in case it didn't happen.

++++++++++++++++++++

A few weeks passed without any word on whether Anna's request would be granted. Most employees who reached 20 years asked the company to pay for a vacation or a car they always wanted but didn't want or have the money for. Anna didn't want any of those things. Her 15-year-old car managed just fine and she didn't really enjoy travelling, preferring to relax at home during her vacations.

"New Office Holiday!" The email subject read. Anna was ecstatic, her request was granted! Plus, she would get to live out a fantasy that she'd been dreaming about for years.

"National Nude Day will be celebrated in the office on July 14th. National Nude Day is a day dedicated to celebrating naturism and nudism, please join us in observing this holiday. Anyone uncomfortable with the nature of this holiday may take the day off." Anna couldn't believe her eyes. She had to read it three times to be sure.

"Is this what you asked for?" Kira said softly startling Anna in her office.

"Yeah," Anna said with a smile, "I've fantasized about strutting around this office in nothing but my birthday suit for the longest time. When I realized I was going to make the 20-year mark I thought this would be my chance to make it become a reality."

Kira couldn't believe they agreed to letting their employees run around the office naked. She confessed that there were a couple guys in the office that she'd always wondered what they looked like naked, but she wasn't sure if it was something she could go through with.

"I do hope you join me," Anna said taking Kira's hands in hers, "but I understand if you don't want to."

The office was abuzz with talk about the new office holiday. Problem was that most of the talk wasn't excitement. Many employees had concerns about leadership even considering allowing people naked in the office, with half threatening to leave if they didn't get rid of it.

Anna made her way down to Jack's office and began spewing concerns that her request was going to lose the company half their people. She never intended to make anyone lose their job and begged Jack to reverse the decision, but Jack refused. The company had taken a stance and if their employees were going to push back against this decision they could leave. If they didn't want to participate, then they could stay home. Nobody was forcing them to show up that day or quit. She thanked Jack for his time and headed out to find Kira.

"What did he say?" Kira asked when Anna walked into her office.

"He isn't going to reverse the decision and anyone who wants to leave can." Anna said trying to hold back tears.

"Hey, don't cry." Kira said embracing Anna in a hug. "This isn't your fault; Jack and the board had all the power to not grant your request and they aren't forcing people to come in."

This was supposed to be a fun holiday, not something that would make people quit.

++++++++++++++++++++

"Good morning Kira," Anna said before pausing, "Kira? What are you doing here? I thought you were taking the day off."

"I was, but I just couldn't leave my work-wife alone in her hour of need." Kira joked as they approached the building entrance. "Shall we?"

They headed directly to the elevator taking it up to the 32nd floor. When they arrived, the office was empty. Normally the office was full of people by this time. Worry began seeping into Anna's thoughts. What had she done? This was a bad idea.

Kira grabbed Anna's arm and pulled her through the glass doors that separated the office from the elevators. There had to be at least one person in the office. The two women wandered around the office looking for signs that anyone was there.

"What are you two doing?" Jack said from behind them.

The women turned around to the 5-foot 7-inch middle aged office manager buck naked before their very eyes. He kept himself in shape with only a small layer of fat prevent his abs from popping out.

"Good morning to you too," Kira said looking down to see Jack's 8-inch cock swinging between his legs.

"Why are you dressed?" Jack said looking between the two women. "Anna, this was your idea."

"I know Jack," she said not try not to stare at his cock, "we didn't see anyone around when we got here and weren't sure if it was still happening."

He instructed them to head to their offices, strip down, and meet him in conference room A. Everyone who chose to participate was waiting for them.

Kira watched Jack's taut ass disappear around the corner. Jack was hotter than she'd previously thought. They headed for Anna's office as Kira's was on the other end of the building and didn't want to do this alone.

Setting her bag down on the chair, Anna began undoing the buttons on her blouse. Kira clearly thought ahead this morning as she slipped off the straps of her dress and pushed it to the floor. Anna always thought Kira was a tall gorgeous woman but seeing her like this convinced Anna that she was indeed a goddess amongst us mere mortals. Her raven black hair draped down her shoulders settling on her perky 30D breasts.

Although Kira was much younger than Anna at 23, Anna was nothing to scoff at. She did everything in her power to slow gravity's effects on her ample 36DDs, which was the only reason she felt a guy would look at her next to Kira.

"Ready?" Kira said as she set her purse and clothes on one of the chairs in Anna's office.

"Now or never," Anna said opening the door.

They made their way down the hall to the conference room. Being naked in the office was exhilarating for Anna as she felt her nipples stiffen. After having worked here for so many years with clothes, she felt naughty strutting around for anyone to see. The office didn't have any blinds covering the windows because it sat above every other building in the city. As rush of cortisol flooded Anna's system as she stopped to look out the window at the bustling city below.

"Let's go Anna," Kira said tapping her on the shoulder, "everyone's waiting for you."

"About time," Jack said as they entered the room, "please take a seat and we'll get started."

The room was packed with 12 people from around the office. Anna was stunned to see so many people had joined her in this adventure.

Jack thanked everyone for participating in the holiday. He explained that nine people opted to take the day off and seven chose to leave the company, which made Anna a little sad.

"Now if we could have Anna come up to the front," Jack said, looking directly at her.

Everyone turned to look at her as she slowly got up from her seat. Things took a turn for the weird when she started feeling small droplets slide down the inside of her thigh. By the time she reached the front she was certain being exposed in front of all her co-workers was turning her on.

"We all want to thank you," Jim said placing a hand on Anna's left shoulder causing her to shudder slightly, "for giving us this experience and we hope you enjoy it."

Anna struggled to remain upright as Jack asked her why she wanted this for her 20-year request while keeping his hand on her shoulder.

"B... because I enjoy being naked at home and out in nature. I..." she stammered as a small orgasmic wave rippled through her body. "I always thought it'd be fun to do at the office."

Jack went around the room asking each employee to give a short answer on why they decided to come into the office. Each time Jack accidentally brushed against Anna's hands or elbow a jolt of orgasmic energy would surge through her. She bit her lower lip each time trying to keep herself in check.

"Is there anything else you'd like to say?" Jack asked taking his hand away and turning to face Anna.

Seeing his cock, half erect now, only make the pent-up energy she was trying to contain worse. Afraid she was going to cum right there in front of everyone, Anna just shook her head.

"Thank you again for this," Jack said reaching out his hand and placing it on her shoulder again.

"Mmmmm," Anna moaned softly as Jack shook her hand.

"Is everything okay?" He said resting a hand on her upper back.

"Uhhhhhh," was all she could manage as a tidal wave crushed any dreams she had of getting out of there.

Collapsing to the floor, Jack kept his hand on her back afraid she was going to hit her head or something. This only caused her orgasms to intensify.

"Ooooohhhhhh," She wriggled and shook cumming harder than she ever had before. Jack continued holding her unsure what to do in that situation and his now hard cock pressed against her side. She could feel the tension in her muscles loosen as she slowly came back down to reality.

"I'm so sorry," Anna said looking up at her co-workers gathered around her.

"It's not a problem," Jack chuckled helping her sit up.

"That was pretty hot," Kira chimed in as the group nodded in agreement.

As they helped her to her feet, she noticed all the guys sporting and trying to hide erections of various sizes. Anna pushed away thoughts of everyone taking turns plowing her right there.

++++++++++++++++++++

"What the hell happened to you back there?" Kira asked closing Anna's office door.

"I don't know, being up there knowing everyone was looking at me got me worked up." Anna said as her fingers lingered around her pussy. "Then when Jack touched me, I was gone."

"God, I wish I could have experienced cumming that hard," Kira said sitting down across from Anna. She continued to gush over the events that just transpired as there was a knock at the door.

It was Jack, he'd come by the office to see how she was doing and wanted to discuss handing the coordination of this event off to her. He'd spoken to the board after receiving a bunch of positive feedback from everyone in the office. The board thought it was a good idea to continue as it was proving to bring their employees closer and lift everyone's spirits. Since this was Anna's idea, he thought she would be the best person for the job. He clarified by saying everything she planned would have to go through the board, but he would do everything in his power to champion her ideas.
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