The Office Milf
Erotic Couplings Story

The Office Milf

by Who2 18 min read 4.7 (13,100 views)
milf mature young man mature woman office romance
🎧

Audio Narration

Audio not available
Audio narration not available for this story

Office flirting before email and text messages

Benjamin Braddock pursued Mrs. Robinson over 30 years before Stifler's Mother first tormented the libido of Paul Finch. Cleopatra seduced the younger Marc Antony, and Catherine the Great had legions of younger lovers. Regardless of the generation, or the era, or the epoch, many young men encounter an older woman who wiggles her butt, or flashes a smile, or mutters a phrase that causes the young man's little heads to take the lead and ignore the reasoning of their big heads...

Mark's family owned a small business with about a dozen employees. They moved from the city to their own property in a small town about 25 miles away to ease the impacts of rising rents. They built a big building that housed loud machinery used in book production and a smaller building for drawing boards, lithography equipment, and early computers. Once the two buildings were completed and the equipment set up and ready for business, people were hired and trained to fill all positions. Most of the new employees were young, barely educated, and looking for one of the low-skill jobs the business offered.

But a few of the employees didn't fit that mold. Anna was hired when the business first moved, but was an attractive, married, mid-30s brunette with two high-school aged sons who no longer needed constant care. She got married at a very young age and had never had a job but was ready to get out of the house and be more than a mom for the first time in too many years.

She also had above-average intelligence and quickly picked up on the more technical skills used in the business. In no time, she spent most of her time working with family members in the small building. Since Mark did most of the technical work, he and Anna worked together every day.

Mark and Anna bonded quickly. She had a razor-sharp wit and enjoyed good-natured smack talking as much as he did. Her blue eyes would sparkle with mischief as she batted one of Mark's off-colored remarks back at him, but her smile let him know it was all in good fun. But what he enjoyed most about working with her was she had a body as good as any girl his age, and even better than his 18-year-old girlfriend.

Mark had been with Lisa for a few months when his family moved to the country, and she was very experienced sexually. She gave him everything he wanted every time he wanted it, and for a while he was thankful for her generosity. It was the non-sexual side of their relationship that left him wanting more. Too many talks turned into fights, and the four-year difference in their age seemed much greater. He looked forward to going to work and could talk to Anna about anything - she provided him that part of his relationship that was missing with Lisa.

As much as he enjoyed talking with Anna, her physical attractiveness was more than a bonus. When they moved to the country, Mark quickly realized that there was much money in the small town nearby. Moms and daughters were hard to tell apart, and women worked hard to hold on to their youth. Anna didn't try looking twenty-something. Instead, she wore thirty-something well, looking like a very attractive mom instead of an aging teen-wannabe. She was 5' 5", had nice tan legs, a fit body, and a perfect ass. Her boobs were noticeable but not extravagant and completed her body perfectly. She was cute but not like a young girl -- her face showed wisdom as well as beauty, and there was also a hint toughness. Then there were those blue eyes that sparkled when she smiled and lured Mark in from the first time her met her.

When Anna took messages for the sales people she bent over the counter with the phone in one hand and a writing implement in the other. One leg would be straight and the other slightly bent at the knee. As she talked, she would exchange which leg did what every few seconds causing her perfect mom ass to move from side to side. Mark stopped answering the phones himself just so he could watch her bend over the counter and perform her seductive message-taking dance. Soon, just watching her walk across the room or stretch high to get a binder from the high shelves were some of the best parts of his day.

One Friday Anna left early but came back to the office to pick up her check. She was on her way to meet Dave, her husband, at the club for a mixed-doubles tennis match. When she walked in to the office in her tennis skirt, Mark lost all control of his 22-year-old libido. She caught him looking at her a few times and enjoyed the attention.

"Nice butt for someone's mom," he said as she walked past his desk, her skirt bouncing with each step.

"Careful, junior!" she said referencing the 14-year difference in their age. "Don't bite off more than you can chew."

"I'd pay money to bite that and chew it," he told her.

They exchanged a few other barbs, and their comments were more suggestive than usual. But as often happened in the small business covering two buildings, they heard the door to the other building open, and they knew family or employees were coming to the small building. Their window to flirt was usually a couple of minutes or less a couple of times per day.

After Mark commented on her skirt, the teasing between them became bolder and more frequent. He never hesitated to comment about her nice butt, or how well her tight jeans clung to it. He begged her to wear the tennis outfit to work more often and asked if she teased other men at their club. As he got braver, he loved asking if she tanned in a bikini or one-piece, or was it possible her tan was all-over? How much would he have to pay to be one of the lucky people who put tanning oil on her?

She loved the attention he gave her and made sure her replies hinted at 'not today, but don't stop trying'. She learned all of his male weaknesses and used them often to tease him. She playfully accused him of checking her out and often asked if he was afraid to get up from his desk because someone might see how excited he was.

They became closer than normal work friends. Mark knew more about her kids than some of his sisters, and he also found out that hers and Dave's country club marriage was all a faΓ§ade. They had fallen out of love years earlier and now were mostly tennis and parental partners. She had sex with him as little as she could but had learned to occasionally give in to keep peace in the home.

Two weeks after Anna wore her tennis skirt to work, she was again bent over the counter talking on the phone. Even though she was wearing her perfect form-fitting jeans, Mark could easily imagine that short skirt and her perfect, tanned legs in place of her jeans.

'Is she wiggling her butt more than normal?' he thought to himself. 'I think she's trying to torment me'.

He was a male with an overly-active sexual imagination, and the more he lusted after her, the more he was sure she was using her awesome mom-body in a way that would arouse him. The better they got to know each other the bolder he became. One day as she took a message, he walked up behind her and swatted both cheeks with his two hands. He let them linger for a fraction of a second and relished at how amazing her ass felt. Then he waited for her retribution, but she never confronted him.

"Did you enjoy that?" she asked, her smile as normal as when they laughed at a crude comment.

She walked to the bulletin board and attached the message for the correct salesperson to call at a later time. He was expecting one of her snarky comments, a warning, or possibly a threat to report him, but she did none of those.

"Uh, more than you can imagine," he replied. "I'm sorry, but you've been torturing with that little dance forever."

"What little dance?" she asked.

He wasn't sure if she was teasing him or just totally unaware of how much her movements impacted him.

"You know, one leg is straight, the other bent. The you switch which one is straight and bent. Every time you switch, your butt moves left, then right, then left... It's TORTURE!"

"Oh," she said as innocently as possible.

She said nothing else, but instead sat back down at the typesetter and continued her work. But she did make sure she was standing for every message she took going forward.

...

As winter wound down, Anna was bent over the counter taking a message. Mark stared at her denim-covered ass like he did any time she gave him the opportunity, and imagined for a second she was naked. He looked around to confirm they were the only ones in the small building, then walked up to Anna and caressed the tight denim. She gently pushed her butt into his hands and moved it side-to-side as she took the message and hung up the phone.

She turned to face him, and when she looked up into his eyes, there were only a couple of inches between the fronts of their jeans. He wanted to push his hips forward that small distance and feel his hardness pressed against her mature, but very sexy, body.

"You know, one day I'm going to do it - reach over and touch you back..." she said, referencing the bulge in his jeans. "...but you'd probably like that."

"Do it!" he dared her. "I promise I will like it, and you might, too."

They made their usual escalating comments to each other until they were no longer alone. Also as usual, Mark went home horny and with a new fantasy about his coworker. He enjoyed the fantasies, and also enjoyed using them while he gave himself pleasure.

The rest of the week Anna took calls like she always had. She did her dance, then placed the messages on the board. Mark took every opportunity to watch her message-taking routine, and when it was possible, he played with her butt. They exchanged suggestive comments, and each night she would star in a different fantasy for him. Mark loved they way they flirted but always wanted a little more.

Friday after lunch, the family took all the drinks out of the soft-drink machine and put beer in for customers to stop by and socialize. About 6:30 the customers had left but the phone rang and Anna again took a message. As she again did her message dance, the four beers Mark enjoyed were enough to remove any rational thought controls, and he crossed the floor to where she was standing, bent over the counter, facing away from him. He felt her butt for the second time, but instead of a swat, his hands lingered for a few seconds. Then rational thought returned, and he let her butt go.

He turned away, embarrassed he'd done it again, and walked to his desk. But as guilt started to build, he thought, 'did she push her rear into my hands? Did she continue her dance while I was feeling her?'

When he grabbed his keys and headed to the door, Anna was walking out as well.

"Have a great weekend," she said as he held the door for her. "I'll be in early Monday. I have to drop the kids off at school early for a tennis trip."

Her smile was the same as any day, and her blue eyes still sparkled. She didn't seem upset at all at Mark's transgression, and if anything, she seemed happier than normal. Was she OK with his somewhat casual flirting and more-than-casual touching?

Monday was warm and beautiful, and when Mark entered the office, Anna was wearing shorts. For the first time since she wore the tennis outfit, he saw her tan legs fit from year-round tennis. She was also wearing sandals so small he could barely see them. He sat at his drawing board, and when Anna brought the type he needed for his ads, it was all he could do not to stare at her perfectly pedicured red toes.

'Holy shit that's hot', he thought as she turned and walked away.

He stared at her ass, her legs, and now those perfect feet as she sat back down at the typesetter. Mark had seen four girls naked multiple times, and a couple of more once or twice. In all his sexual escapades, he never once remembered any of them having painted toes. He had also spent as much time as possible at the lake or the beach where bare skin was available for viewing. Was he too busy taking in the other female body parts that were normally concealed from him to notice their feet? Or maybe this was a new fetish for him?

The first time Anna took a message that day, Mark was surprised at how much more he enjoyed her dance now that she was in shorts and sandals. The way she moved taunted him even when she wore jeans and tennis shoes, but now that her legs and feet were uncovered, it was seductively sexy. Her calves, slender ankles, and those red toes! It was hard not to stare, and he was pretty sure she'd seen him looking at least once.

It was just before lunch when Anna took her first message of the day and the office was free of other workers. Mark tried to keep his composure, but when he was only mortal. When she started the dance, he walked up behind her.

"Let me apologize in advance for what I'm about to do," he muttered before feeling both cheeks of her butt. The last time it had been a quick cupping of her ass, but this time he took a longer feel - more than a few seconds - let his hands linger, memorizing how she felt.

Like before, she didn't object, and he was now 99% sure she pushed back into his hands, rewarding his boldness. But after that few seconds of bliss, she walked over to the message board and posted the message.

"I was wondering if you liked these shorts," she said as if nothing had happened.

"Uhhh... YEAH, and the sandals and the..." he didn't finish his last comment.

"And the 'what'?" she asked as she sat back in her chair.

"Your sandals... and those painted toes!"

"These?" she asked teasingly as she lifted one foot off the floor and pointed her toes.

"Do you have a foot fetish?" she asked.

"Yes, THOSE!" he replied, exasperated. "...and I might."

Mark looked at her feet one last time knowing she was watching his every move. His secret was out, and she was obviously teasing him, so he didn't have to hide his longing look.

"I'm going to run home for lunch and take a cold shower," he said as he grabbed his keys.

He wasn't really going to take a cold shower -- he wanted to rub one out while the image of her smooth skin and memory of her firm butt were still fresh in his mind. He did want her to know how aroused he was, though.

"Why do you need a cold shower?" she asked, feigning innocence and also delaying his departure.

"Why do guys EVER need a cold shower?" he replied.

"Well, shoot. I was hoping you might want to go out for some tacos," she answered.

'Hmmmmm... jacking off while fantasizing about Anna...' he thought to himself, 'or lunch with Anna looking at her in those shorts.'

"Sounds good. I'm driving," he said as he opened the office door for her.

They managed to enjoy a longer-than-normal lunch without discussing him grabbing her butt, or his cold shower, or why she wore shorts and sandals to the office. They had become close over the past months, and even closer after the past few days of teasing and groping.

As the summer wore on, Anna wore shorts and sandals to the office more often than not. She even sometimes kicked her sandals off when she was at the typesetter or the counter that doubled as her desk. And most times when it was only the two of them in the office, he played with her butt when she took messages. His desire for her was growing, and even though he loved feeling her butt softly pushing into his hands, he needed more.

One afternoon when she was barefoot at her desk taking a message, he approached her like he usually did. But instead of feeling her butt, he grasped her hips and pulled her tight against the bulge in his jeans. Again, he was wondering if he was crossing a forbidden line, but her past responses lead him to believe this would be welcome, or at least tolerated. Again, he felt her body push against his, but then she stood up and turned to face him. She quickly looked up at him with that smile as she pushed her hips against his.

"No need to ask if you enjoyed that," she said coyly. "I could tell that right away. Was that because of me?"

Her face was oh-so-close to his, and for a moment he thought of kissing her. But either to avoid the situation, or to enhance the tease, she side-stepped away from him and put the message on the message board.

"Would I get in trouble if I said it was because of you?" he asked, not sure how to respond with any answer she might provide.

"Have I ever gotten mad at you?" she asked. "It's not like I'm going to start today. I think you're pretty harmless."

"Harmless?" he asked with excited exasperation. "That was harmless, me rubbing my... uhhhhhh... 'junk' against you? You consider that harmless?"

"I thought that just got you excited for Lisa," she said, referring to his girlfriend.

"Maybe for a while," he answered more calmly. "But, DANG I think about it all the time... uhhh... and it felt SOOO good... ahhhhhh... and I think I really need that cold shower now!"

"Well, I have to admit," she answered, still smiling like nothing was wrong. "I might need one of those myself. You kinda surprised me there."

"Oh, GREAT!" Mark answered. "Now I have to think about you taking a cold shower while I take one. This is going to be a hard, hard night!"

"Ohhh, did I say 'cold' shower?" she teased as she again got very close to him. "I'm going to take a hot shower, or maybe a bubble bath... with lots and lots of soap to rub all over my body, over and over... and when I'm done I'm going to be SO clean and SO relaxed..."

Mark watched her mouth, her eyes, her smile, the way her body moved, as she approached him. He had always been the pursuer while she innocently went about her daily tasks. But was she now seducing him with her hot, sexy story and nearness of her body? As she inferred touching herself in a warm, soapy bath, their bodies were almost touching. She stopped and looked up into his eyes while mischief and intrigue filled her own.

Mark was unsure what to do now. Normally, when a girl was this close to him, it was a girlfriend or a date, and this was a part of the intimate game that led to hot, satisfying sexual interaction. But this was the office, and his opponent was an older, married coworker. This was a new, unfamiliar game for him. He had started the game when he first played with her butt, but now she had made the next move.

He looked back into her eyes, trying to match her playfulness, but also adding a hint of boldness. He embraced, one hand in the small of her back, the other grasping her gorgeous ass. He pulled her body tightly against his own, his lips brushed against her ear.

"While you're in that bath enjoying rubbing soap on your sexy, naked body, think about this..."

He pushed his hardness against her, his one hand tightly squeezing her ass while also pulling her hips against his.

"...because I promise I will be thinking of you, naked, in that bath."

He held her tight for a second longer, memorizing how her body felt against his. Then he released her, grabbed his keys, and headed to the parking lot.

"OK," she muttered as she watched him leave.

...

On Monday, Mark, Anna, and the others showed up to the office at their regular times. There was the typical, Monday chatter, coffee, and discussions on what needed to be done for the week. It was almost 10:00 before they were alone to discuss what happened Friday afternoon.

"Did you take that cold shower?" she asked him.

"No, I took your advice and enjoyed a nice, looooong hot shower with lots of soap, the excellent visuals you gave me, and a very intense ending," he said with a satisfied smile. "Did you take a bath, or were you just torturing me?"

"I did, and it was everything I hoped it would be. Most relaxing evening I've had in a long time."

"Did you think about what I suggested?" he asked.

"I did..." she answered with a naughty smirk. "That's probably why it was so enjoyable."

She didn't tell him that he had left her so flustered that she took multiple baths over the weekend, and she treated her body to multiple, well-deserved relief sessions.

Enjoyed this story?

Rate it and discover more like it

You Might Also Like