Harmless Office Flirting

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***All characters are over 18 and are fictional. Any resemblance to any real-life persons or situations is purely coincidental.

***Originally published as Harmless Office Fun Ch. 1.


Mike Wilson left his apartment a couple of hours earlier that morning so he could hit the gym before work. His office building was right next door to the gym, and they gave membership discounts to the employees of his company, so it was very convenient for everybody.

He did his usual workouts, pushing himself a little more on the free weights, but decided to skip the treadmill this time so he wouldn’t be late to work. Mike enjoyed staying fit and healthy; his father died at a young age, and he didn’t want that to happen to himself. He didn’t want to become a bodybuilder, but he enjoyed the muscles he had been getting over the last couple of years, and so did his wife.

He saw several others who worked at his company, even a few who worked for him in his department. One of them was one of his top sales reps, Fiona Miles, who was killing it on the treadmill, as she usually does. She had her blonde hair tied back in a ponytail for her work out, and she was wearing small gym shorts and a tight tank top. She was always at the gym, and because of that, she had a great body that you’d have to be blind not to notice.

A lot of men in the office have hit on her at some point, but never Mike. Besides the fact that he was happily married, he would never think of giving her a simple friendly comment on her haircut out of fear it may be misconstrued as something else. He had seen enough people get in trouble for taking it too far, including the person who previously held his position at the company. Because of those people, he had been to enough sexual harassment seminars that the company made everyone take, to know to just shut up and keep your hands to yourself.

After he was done with his workout, he had a quick shower in the locker room, got dressed, and made it to work just in time. As soon as he got off the elevator on his floor, he was approached by his best friend and one of his other best sales reps, DJ. The smile on DJ’s face indicated one thing, he scored last night and wanted to brag about it.

“It was a bartender. I’ve never had a hot bartender before,” he said as they both made their way to Mike’s office.

“I have. Twice,” said Mike.

“That was back in college, before you went corporate and became lame,” DJ replied.

“I still get laid more than you, even now.”

“Only because you’re married and don’t have any kids yet to slow you down,” DJ replied. “How do you live with yourself banging only one woman?”

“Don’t knock it until you try it.”


They got to Mike’s office, and he was still trying to tell him about the bartender he scored with while Mike was getting himself set up for the day. Mike had to admit that even though he’s happily married to Janet, he did miss the single life and sometimes enjoyed hearing DJ’s stories of his conquests.

He was sitting behind the desk, going over some paperwork, while DJ sat across from him, his feet propped up on the edge of the desk, taking his time getting to the end of the story.

“So, we found ourselves in the storage room at the back of the bar. I had her shirt off, and finally got my hands on her tits–“

There was a knock on the door, which made DJ suddenly go silent. Both men looked over to see Fiona at the door with some files in her hand. She was looking much better now than when Mike saw her at the gym earlier, where she was getting sweaty from the treadmill. She was cleaned up now; her hair was down, and she was wearing a navy-blue blouse with a black skirt.

“Don’t stop on my account,” she said, smiling.

DJ just sat there silently, trying to figure out how to get out of his situation. It’s one thing when he tells his stories about getting laid to his friends, but he’s smart enough not to tell those stories in mixed company. At least he was smart about it now; he had been called down to the HR department enough times for his comments over the years to finally know when to shut up.

“Go on, DJ. You had your hands on her tits, and what happened next?” Fiona was waiting for him to finish with a smirk on her face.

“Come on, DJ, finish your story,” said Mike, trying to contain his laughter. He was taking a little enjoyment in seeing his friends’ humiliation like this.

“Alright, I get it. You can both stop messing with me now,” said DJ.

Mike and Fiona had a chuckle at DJ’s expense, who just sat there feeling very embarrassed.

“Can I help you, Fiona?” Mike asked.

“Sorry to interrupt your boys’ club, but I need you to approve these sales reports.”

Mike got out of his chair, and they both walked up to each other. She handed Mike the files she had, and he gave them each a quick glance.

“I saw you at the gym this morning, Mike,” she said. “You were really pushing yourself.”

“Yeah, I thought it was time to add a few extra pounds to the weights today.”

“Don’t strain demetevler escort yourself too hard; you’ll burst out of your clothes,” she said as she put her hand on his bicep and gave it a gentle squeeze.

DJ saw what she had done and got excited by what he was witnessing.

“I’m careful, I know my limits,” he said while still reading the files and signing off on each one with his pen.

“Too bad you weren’t on the treadmill; we could’ve had a good run together,” she said.

“I usually do, but I didn’t want to be late to work. Maybe next time we see each other there,” he said, handing the files back to her.

“It’s a date,” she said, and she walked out of the room smiling.

“Dude,” said DJ as he got up from his chair. “Did you not notice what just happened?”

“What are you talking about?”

“She was totally flirting with you.”

“What? No way,” Mike shot back at him.

“She was complimenting you on your workout.”

“I’ve done the same to other people I know who like to work out,” Mike replied.

“And didn’t you notice the way she kept smiling at you and how she touched your bicep? Only women do those kinds of things to show they’re interested.”

“Come on, DJ. Fiona knows I’m married.”

“That doesn’t mean she wasn’t flirting.”

“Are you saying she wants me?” Mike asked.

“Definitely!” DJ replied enthusiastically. “I mean, she’s not stupid enough to go after a married man and her boss, it could ruin her career. But that doesn’t mean she doesn’t think you’re attractive enough to flirt with.”

“So, what should I do about it?”

“You flirt back,” DJ replied.

“I can’t do that.”

“Why not? It’s only a little harmless office flirting.”

“I don’t think that’s a good idea,” said Mike as he sat down back at his desk. “If you remember, our previous manager, the guy who the company asked me to replace, tried something similar, and he got fired.”

“No, he got fired because he went too far and tried to use his position to get sexual favors from a few women in the company. I’m not suggesting you fuck her, just flirt back a little. Don’t you miss how good it felt back when you were single and flirting with other women?”

“Sometimes I do,” he admitted.

“So, give it a try. The next time she flirts with you, just flirt back a little. Even when I don’t score with women–“

“Which is often,” Mike said, jokingly.

“Good one,” DJ said with a chuckle. “As I was saying, even when I don’t score, I still enjoy flirting. It’s fun, and it makes you and the other person feel good. You’ll probably enjoy yourself for once.”

“What about sexual harassment lawsuits? We’ve been to enough seminars to know better.”

“Yeah, those things are so much fun,” DJ replied sarcastically. “Just keep it simple. Don’t say anything too sexual. Just compliment her looks and other little things.”


Over the next few hours, Mike made a bunch of phone calls, set up some new appointments, fixed a problem with the budget, and so on until it was lunch time. He went down to the ground floor of the building to a sandwich shop he frequented. He thought DJ was going to join him, but he was too busy with a few sales leads. It was good to see him focusing on work and not just hitting on women in the building.

He was sitting at a table in the corner, eating a veggie sandwich. There were a few other people from his company, all doing their own thing, so he didn’t bother them and sat alone. But that lasted only a few minutes before Fiona unexpectedly showed up.

“Mind if I join you?” She asked.

“Sure,” he replied, but she was already sitting down by then.

The conversation he had with DJ came back to him, and it made him look at Fiona in a different way. She had long blonde hair, green eyes, and a great body from what he could see at the gym. He guessed she had large C-cups, definitely bigger than his wife’s breasts. He tried not to look at her body too much, out of fear that she might notice. Instead, he focused on his lunch and having a decent conversation with Fiona as long as she was sitting with him.

They talked while they ate, mostly about work and a little office gossip. He already knew about some of the gossip, but he was sure there were a few things Fiona didn’t’ want to gossip with the boss about, which was completely understandable. He was the same way before his promotion.

They talked a little about working out as well and what they were doing to stay fit. That’s when she noticed the veggie sandwich, he was eating.

“You also like to eat healthy, I see,” she said.

“It’s not just working out to stay healthy, you’ve got to eat healthy as well,” he replied.

“Believe me, you don’t need help there,” she said as she touched his arm again, just like she did back in the office.

Mike finally had to admit that she was indeed flirting with him. He couldn’t believe he didn’t see it before and made him wonder how many other women might have flirted with him but dikmen escort he was too oblivious to notice.

“I’ve got to do more to lose a few pounds,” she continued. “Summer’s coming up, and I have to get my beach body ready.”

It was at that moment that he decided to take DJ’s advice and flirt a little, just to see how it felt.

“From what I can tell, you already have that beach body.”

She looked at me and smiled.

“You really think so?”

“Definitely. I’ve seen you at the gym. You look amazing.”

He was a little nervous saying that, worried that she would think he was going too far and take offense. But when he saw her smile, it eased his concerns, and he was able to relax.

“Thanks. I didn’t think you ever noticed me.”

“Hey, I’m not blind. Nothing wrong with admiring a beautiful woman,” he replied.

She giggled; it was very cute.

“You think I’m beautiful?”

“Of course, I do,” he replied.

He liked the way she smiled at him just then and thought it was cute the way her cheeks slightly blushed. He also liked how good it felt talking with Fiona like this. He had to admit that DJ was right, it does feel good to flirt with a beautiful woman just for the fun of it.

“I’m glad to hear you say that,” she said as she put her hand on his lap.

“Huh?” he said, unable to think straight with her hand on his lap and her fingers just on the inside of his thigh.

“Just to let you know. I don’t care if you’re my boss or that you’re married. Anytime you want me, I’ll be ready for you.”

“Huh?” was all he could say again.

“I gotta get back to work,” she said as she wiped her mouth with a napkin. “You’re cute when you blush.”

She got up and walked away from the table. Before she left the sandwich shop, she looked back at him and gave him a wink.



A couple of hours later, Mike called Fiona into his office. He thought he should have a private conversation with her about what had happened at lunch to assure her he was not interested in having an affair with her. When she came in, he closed and locked the door for more privacy.

“Oh, so soon,” she said with a wicked smile.

“What?” he asked.

“You locked the door. What else could that mean?” she said as she undid the top two buttons of her blouse. “Although we might have to do this quickly before anyone realizes what’s going on in here.”

“Oh, no, that’s not it,” he said nervously. “I just wanted to tell you–“

Before he could continue with what he wanted to say, there was a knock on the door. Fiona buttoned her blouse back up as Mike went to answer the door. He unlocked the door and opened it to find his wife, Janet, standing there with a big smile on her face.

“Hey sweetie,” she said.

“Hey Janet,” he said, trying his best to hold back his nervous behavior.

With everything going on, he had forgotten that Janet was planning to stop by to go over some rug samples for their apartment.

Janet entered the office, and she took notice of Fiona standing there.

“Fiona, this is my wife, Janet. Janet, this is Fiona.”

The ladies shook hands and greeted each other.

“I hope I’m not interrupting anything,” said Janet.

“We were just briefly going over some work stuff,” he replied.

Mike gave Fiona a file that was on his desk, not caring what it was for. He was just trying to make Fiona’s presence in his office look like it was work-related. Fiona looked happy to see what the file was for and thanked him for the opportunity to work on a big account like this. Mike had no idea what she was talking about; he assumed she was just going along with the story because Janet was there. Fiona said her goodbyes and left the office, leaving Mike alone with the one woman he was supposed to be involved with.

They went to his desk and started looking over the rug samples that Janet had brought with her.

“She was pretty,” said Janet, smiling.


“Don’t act like you don’t know what I’m talking about,” she said.

“Oh, Fiona, yeah, she’s alright.”

“Oh, please, you don’t have to play dumb on my account,” she replied. “She’s hot; just admit it. I won’t be jealous.”

“I have no idea what you’re talking about.”

Janet laughed. She thought it was cute the way Mike was pretending not to notice how attractive Fiona was for her benefit. They’ve had this conversation before; they don’t mind if they think other people are attractive as long as they only have eyes for each other. But Mike was sure that if Janet knew what was going on today, she wouldn’t be making jokes about it.

They went through the rug samples pretty quickly and found the one they liked best for the apartment. Janet left to go check out some furniture she had her eye on. Afterwards, Fiona showed up in the doorway.

“I just wanted to let you know,” she said. “Almost getting caught only made this more exciting.”

She left, and Mike slammed his head down on the desk.


“What elvankent escort the hell?” DJ yelled as he barged into Mike’s office.

“What?” Mike asked.

“You gave Fiona the Tremont Savings account. I know more about that account than anybody else; I deserve that account. How can you do this to me?”

Mike just realized the file he gave to Fiona to cover up why she was in his office when Janet showed up was for an account that DJ had been vying for for months now.

“How can you stab me in the back like this?” DJ asked.

“Would you shut up and let me explain?”

First, Mike apologized for giving the Knowles account to Fiona and assured him it was an accident. To make up for it, he offered DJ a better account, which would give him a higher commission, which made him very happy.

When all that was settled, Mike told him about his lunch with Fiona. DJ seemed happy for him for flirting with her, but was shocked when Mike told him about what happened at the end.

“Dude, you’ve got game,” said DJ as he held up his hand, looking for a high-five, which he wasn’t getting.

“DJ, she thinks I want to sleep with her; what am I supposed to do now?”

“You tell her, firmly but politely, that it was just a little friendly flirting and that you are not interested in having an affair with her.”

This led Mike to explain how he tried to do just that, but Fiona mistook his attempt to talk to her for a midday sexual encounter. He then described how Janet suddenly came into the picture, which led to Mike accidentally giving her the Tremont Savings account. By the end of the story, DJ was having a good laugh at Mike’s expense.

“Wow, you are in quite a predicament,” said DJ. “Listen, your plan to talk to her would’ve worked, but your wife interrupted that attempt. Try it again, Fiona is a reasonable person; I’m sure she’ll realize it was all just a misunderstanding.”

“She didn’t seem reasonable when she was trying to take her shirt off in my office.”

“You didn’t mention that part,” DJ replied, looking stunned. “What color bra was she wearing? How much cleavage did it show?”

“I didn’t see anything, DJ. Please focus,” Mike snapped at him in frustration.

“Sorry. Like I was saying, if you talk to her, she would understand. But with all the distractions in the office, it would be difficult. So, what you have to do is get her alone. She said she was going to stay after work a few extra hours to look over the Tremont Savings account. So, when everybody is gone, get her alone in your office, and that’s when you talk to her about this situation.”

“Wait until everybody is out of the office and get her alone? Where there are no witnesses? That’s your plan?”

DJ paused for a moment. “Now that you say it like that, it does sound like a plot in a porno. But I think if you put your foot down right away, you should be ok.”

He thought about it for a little while and agreed with DJ that it was the best course of action.

“Just remember, let her down easily. You still have to work with her tomorrow.”


Mike called Janet to let her know that he would be home late to fix some work-related problems. Technically, it was true because this situation with Fiona was definitely interfering with his work, and he couldn’t get anything done most of the day because he was so preoccupied by it.

Everybody in the office had left by 5:30, leaving only him and Fiona. Mike took a few minutes to practice what he was going to say to her to make sure it was done right without causing any problems between them. It was just like DJ said, he had to let her down easily because they still had to work together.

When he was done, he called Fiona on her extension and asked her to meet in his office. As soon as he hung up, he realized what a bad idea it was to be alone in the office with her like this. He was afraid it would give her more signals that he wasn’t trying to give. But he knew he had to resolve this misunderstanding between quickly them before it escalated.

A few minutes later, Fiona walked into his office and shut the door.

“Alone at last,” she said with a sultry smile. “Now we can try this again without any interruptions.

“Fiona, we have to talk about this.”

“We could talk,” she said as she began to undo the buttons on her blouse, “or we could play.”

“That’s what I want to talk to you about. “Back in the café, you have to understand,” he tried to finish, but he was too preoccupied watching her take off her blouse. “I never thought I’d say this to a beautiful woman, but please stop doing that?”

She had taken her shirt completely off now. She was wearing a white lacey push-up bra that showed a great deal of cleavage. Mike stood there, frozen, not knowing what to do next. She walked up to him, and he backed away. He kept talking to her, trying to explain the situation, but he only stammered his explanation, and she thought he was just being nervous, which only made it hotter for her. He kept backing up until he hit the desk, and she was right up against him.

“I am not interested in what you have to offer,” he said firmly.

That’s when she removed her belt and let her skirt drop to the floor. She was now completely in her underwear in my office. He had this dream many times, a beautiful woman undressing in his office, but the woman he always imagined doing that with was his wife.

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