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Yes, Ma'am

"My sexy boss asks me to work overtime and some unexpected results occur."

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It was a normal work day until I was told by my manager Anne that I had to stay for overtime. I tried to explain to her that I couldn't because my wife expected me home on time so I could watch the kids as she had plans to go out after dinner to meet a friend. Anne gave me a wry smile that made me a little uneasy before she explained that we were behind on our monthly inventory counts and staying late could not be avoided regardless of my wife’s plans.

After an unpleasant phone call to explain the situation to my wife, Anne and I found ourselves in the far back corner of the warehouse as we counted inventory. We had made brief small talk for about twenty minutes while we worked before the conversation shifted to a more personal nature. She asked about my family and how they were doing, so I gave her a quick update.

I knew she was having problems with her husband, so I tried to delicately ask how she was doing with that situation. Her response about her relationship was vague and gave the intentional impression she did not want to get into it, but she commented that she did miss some parts of the relationship that had gone away.

She spoke this last part in a suggestive tone while looking me up and down in a way I was meant to notice. She was a sexy lady and I certainly had eyes for her - most of the guys in the warehouse did - but I always kept things appropriate since she was my manager and I respected how she ran the warehouse for the most part. I liked working for her, and she had always seemed to like my work ethic since I was dependable, but this was something new.

Anne had usually acted in a strictly business manner around me in the two years I had worked with her. Her father owned the company and had already arranged that her older sister would take over once he retired. Anne had not been with the company for as long as her sister, so she usually took her work seriously. I was a bit unsettled at the way she looked at me now with blatant desire.

She changed the subject and told me to grab the wheeled staircase from the next aisle so we could count the upper level of racking. Once I got the stairs in place, she ushered me up to the top so I could count and call down the numbers to her. The last item in that spot had a serial number that we had to verify as well. I struggled to find it, but Anne reminded me the number was on the bottom of the box.

“You hold it up and I’ll read it,” she said as she climbed up the staircase towards me. Once she was two steps below me, I picked it up and held up the heavy box while she read the number and wrote it down. Sometime during this process, I felt her fingers touch the back of my knees just beneath the cuff of my cargo shorts. I didn't balk at first but when her lingering touch started to slide up my loose shorts, I started to flinch uncomfortably with the heavy box in my hands.

“Careful, Charles,” she warned in a sultry voice as her palm slid up the back of my thigh. “Don’t you dare drop that box.” Her fingers were touching the edges of my boxers when I reminded her that I had a wife. She chuckled at this and responded in a mock afraid tone

“Oh no! Is she gonna come here and beat me up?” Her fingers were under my boxers now, and I reminded her that the HR department would not like this and that the warehouse had cameras in it. She laughed at me.

“I thought you were clever, Charles. Don’t worry that pretty head of yours, do you really think they would take your word over mine? The camera for this aisle has been dead for over a year. Besides, I’ve seen you looking at me, I think you like this.” Her fingernails were lightly scratching my scrotum now as I thought through my options. I knew this was an aggressive bluff, but I also knew that her word did in fact mean more than mine at the company, and reporting this would be like swatting a hornet’s nest even if they did believe my story.

I had seen what happens to people who get on Anne’s bad side and one way or another they did not last long. I not only needed this job, but I enjoyed it for the most part and didn’t want to rock the boat and risk losing the experience and seniority I had here. I loved my wife and kids, but I had never been good at resisting temptation when I thought I could get away with an indiscretion. Things with my wife had been stale for the last few months, so I decided to go for it and weakly responded to her.

“Okay,” was all I could manage as I pushed the thought of my wife out of my head while Anne’s warm and smooth palm closed around my balls. Her touch was firm and encompassing but also delicate as she massaged and stroked them. I couldn’t deny how good it felt.

“Your balls have only been in my hands metaphorically for too long, Charles. It's nice to play with these big beauties for real.” Her hand opened, and her fingers moved up to my penis to feel it get stiff in her hand. Her index and middle fingers ran up and down the bottom portion of my shaft while she spoke in the same condescending tone.

“If I let you put that box down, will you be good?”

I gave her a concise and firm answer to indicate my level of compliance which she enjoyed, but she did not take her hand off my genitalia until I put the box down. I turned around carefully to face her and my bulging crotch was directly in front of her face. She motioned for me to sit down on the top step as she unzipped my fly.

“I should have known you had a nice cock, Charles.” She looked up at me as she pulled it out of my boxers, she grasped the shaft firmly as she leaned in to give it a kiss. She licked her lips to moisten them and slowly slipped the head into her mouth until about two-thirds of it was in, before pulling back and then continued at a moderate but steady speed for what felt like minutes but was probably less than thirty seconds as neither of us had forgotten the unsafe nature of having two people on one of these staircases.

Once we got down, she gave my now wet penis a look and told me to follow her to her office. I felt a little guilty for having gone along with it so far and I felt even worse for how far I knew I was going to let it continue to go. I loved my family dearly and I had also met Anne’s husband at last year’s Christmas party. Him and I talked for about forty-five minutes while Anne took care of company business. He was a good guy and we connected over NBA playoff theories since we were both fans. I didn’t feel good since I knew him a bit, but then I remembered how his wife’s lips felt on my dick.

Anne led me out of the warehouse and up to the empty office portion of the building. She exaggerated the sway of her hips as she led me toward the executive offices and her blonde hair moved playfully along. She was only a couple of years older than me by my best guess, so I had checked her out many times in the two years I had worked with her. When I started working here, she looked like she spent a lot of time at the gym from her toned athletic body. However, during her recent marriage issues combined with more responsibility at work, her routine and her life were disrupted and she had less time for the gym it seemed. She had gained weight, not too much, but it was noticeable. I thought she looked good with a little extra weight though, considering how fit she was when I first met her.

Her boobs, butt, and thighs had all received a nice addition. so who cares about a little extra on her gut? That was my opinion with the warehouse guys when the topic inevitably came up. Regardless of looks and locker room talk though, she and I got along well despite her tendency to be bitchy when things didn’t go her way. We were both good at our jobs and appreciated being able to rely on each other when it was needed. I was pondering the veracity of warning phrases like ‘don’t dip your pen in the company ink’ as we walked but when we got to her darkened office the way she looked as she motioned for me to go in first pushed all hesitation out of mind.

“You have a pretty good history of helping me out when I need you to do something, Charles, let's hope that you can keep that going.” She unbuttoned the top two buttons of her blouse before following me in and closing the door behind us. She looked at me with a satisfied look on her face before telling me to get naked in a demanding tone. I complied without a word and stood naked in her office which was now lit with a single desk lamp.

She unzipped her jeans as she eyed me up, I could tell she was hungry for me, but she held these feelings in check. She slipped out of her jeans and panties and sat down on the edge of her desk while ordering me down between her legs. I was unaccustomed to being bossed around as my wife was timid in bed, but I enjoyed it and quickly did as she told. I moved my face in position between her spread thighs as she leaned back and pushed her pelvis forward to meet my face. I licked my lips and eyed up her moist pussy eagerly.

I gently stroked my index finger up and down her labia to feel her growing wetness. As I was savoring the moment, she gave an exasperated sigh and grabbed my head by the hair, and pulled it into her crotch. She enjoyed the feeling of my beard against her smooth thighs, but she quickly moved on from this feeling as my tongue gingerly grazed her clitoris. Her fingers wormed through my hair as I gradually increased the pressure of my tongue on her clit.

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She moved her hands off my head to finish unbuttoning her blouse and threw it on a nearby chair before putting her hands forcibly back in my hair. Her husband was bald, and she seemed pleased with my thick head of hair. When I started to slide a finger inside her she tightened her grip and told me to keep going. I was licking at a steady pace and slowly inserting my index finger into her when her hands left my head and reached behind her back to remove her bra.

I paused to look at her exposed breasts as she placed the bra on the table. They looked even nicer than I had pictured in all my slow afternoon daydreams. Her face got serious though as she told me to get back to work with another exasperated sigh and forced my gaze away from her breasts and back to her pussy. I enjoyed her bossy attitude; she was always assertive in the workplace, but this was different. She was forceful, she tightened her thighs around my head, and I could feel the warmth of her skin on my cheeks and temples. She started moaning once my licking continued, I held my index finger halfway inside her while my mouth worked.

“Charles, you are good at this. Do I have your pretty wife to thank for that?” I lost my rhythm briefly and pulled my finger out at the mention of my wife, Anne snickered contentedly for a few seconds before telling me again not to stop. She grabbed the back of my head and started to grind her pussy into my face, slowly but forcefully she slid herself against my wet pursed lips and her moaning continued.

“Oh yes, Charles… I am going to have to send your wife a special Christmas card this year.”

I had never been with a woman who was so forceful before, my wife just laid back and let me do the work, but I really enjoyed Anne’s demanding nature as she fucked my face. After several more thrusts, her pelvis stopped moving. I started to slowly finger her again and her moaning got even louder. My cunnilingus skills were every bit as good as my wife and boss said they were, and I would use them to leave an impression on her.

After a few more moments of licking and fingering, Anne could not hold back anymore. she announced her oncoming orgasm, grabbing two stinging handfuls of my hair as she climaxed. I continued until she let go of my hair and motioned me away. She took some deep breaths before telling me to go wash my face off in the bathroom. I grabbed my pants to put them on first, but she shook her head no.

“Leave them, there is no one here but us,” She smiled at the uneasy look on my face as I put my pants back down on the chair. I felt awkward and exposed as I walked down the hallway of offices, I felt particularly anxious as I walked past her dad’s office which I already knew to be empty, but a part of my paranoid mind expected to see him there tapping his toes. Just waiting to fire me for fucking around with his married daughter, I was a bit relieved to see the office empty as expected on my way to the men’s washroom but I still hurried.

I felt no better when I got to the bathroom and could see my nakedness under the fluorescent lights in the mirror. I quickly washed her wetness from my beard before returning to her office. She was still sitting in mostly the same position on the desk waiting for me. She had a smug smile on her face as she watched my flaccid but still slightly engorged penis move with each step as I came down the hallway to her office.

“You’re a lot of fun aren’t you, Charles? I am going to be nice to you since you have been so helpful. Come over here and fuck me.” She shuffled herself to the edge of the desk, laid on her back, and ordered me to hold her legs as she lifted and spread them. I quickly complied and I positioned myself in front of her. I was more excited to fuck my boss than I had felt in years of regular marital sex as my now rigid penis slipped into her wet pussy. We sighed in unison as I entered her, I savored the feeling of slowly inserting the full length. I pulled back and repeated the motion two or three times before my phone rang in the pocket of my pants. She was frustrated at first but then a wicked smile crept onto her face as she guessed who it must be on the line.

“That could be your wife, Charles. You should pick up. I wouldn’t want her to worry about you.” She looked up at me with a sexy but sinister smile on her face as she continued in a teasing tone “You wouldn’t want her to get mad.” I tried to say I would call back after we finished but her smile only grew as she continued. “No. Pick up now, while you are still inside me.” I gave her an incredulous look, but she answered my question before I could speak it.

“Yes, I am serious. Do it or I will make you finish counting the rest of aisle sixty without your clothes...band without cumming.”

I did not doubt for a second that she would follow through on her threat if I didn’t obey and the fact that I was still inside her while I pondered this swayed my opinion heavily towards continuing at any cost. “Just stop thrusting and I’ll cover my mouth so she can’t hear me breathing.”

Against my better judgment, I picked up my phone and confirmed that it was my wife. I took two deep breaths and tried to ignore the obvious and logical objections in my mind as I unlocked my phone. It was a leap of faith that Anne would in fact stay quiet as she promised but I figured that she didn’t want to get caught either, she just enjoyed torturing me. I was surprised by how much I enjoyed it too as I answered the call. Anne picked up her nearby blouse and folded it up in an exaggerated motion to place over her mouth as she watched and listened.

I could see how big her smile was even while it was covered by the twinkle in her eyes as she overheard my wife’s heated reaction to the update of another half hour or so. She sensed something off in my tone when Anne started to move her pelvis slightly and my penis twitched accordingly, but I quickly made up a story about being in the middle of moving heavy boxes and that I could not talk long. After several more heated sentences from my wife complaining about how I spoiled her evening out, I managed to hang up without her knowing the truth of the situation. Anne tossed her blouse aside and started laughing with an almost cartoon-like evil as she watched the uncomfortable moment wash over my face.

“She sounds angry, Charles,“ she said in between fits of laughter. “Maybe she needs that magic tongue of yours to calm her down when you get home.”

I interrupted by pushing into her harder, I knew that sex with my wife wouldn’t be a possibility for a while after this stunt, so I was going to get my fill now. She encouraged my newfound vigor, “There you go, Charles, get all that frustration out now because your fun is over when you get home.”

I was sliding into her with a steady and firm thrust. It was a moderate pace, but I pushed hard and could tell from the look on her face that I was hitting a good spot, she moved one hand down to her clit and tweaked her nipples with the other before sliding it up one of my arms as I supported her thighs.

For the next few moments, the dominant boss demeanor faded away and she just enjoyed the feeling of my strong thrusting into her. I watched her boobs jiggle slightly with the momentum of our movements as they lay flat. I knew I was having a good day long before that moment but it was only further confirmed when she indicated that she was close to another orgasm when I started to feel my own orgasm clock ticking down. I managed to hold off until her climax subsided but once I announced I was going to cum her dominant boss attitude came back as she spoke with a smile.

“Don’t you dare cum on me, Charles!” She reached over her head and brought a Kleenex box within reach of me. I gave her an exasperated look which she thoroughly enjoyed, but I had no intention of disobeying her at this point. I gave her a few last thrusts and then put her legs down and looked at her naked body as I jerked myself off into a wad of Kleenex. I tossed the soiled tissue into a garbage can as I backed away from her. We both collected our clothes and started to dress ourselves while she spoke.

“I am impressed, Charles. Extremely impressed. I haven’t been fucked like that since college. Let’s hope that pretty wife of yours doesn’t mind me borrowing you again sometime.” She slipped her jeans back on as I struggled for an answer, but I only nodded my head in an affirmative gesture as now I was thinking about what I would say to my wife when I got home. Anne laughed again and knew I would be just as compliant next time around.

After we were both fully dressed, she told me we could go home now since she never really cared about getting aisle sixty counted in the first place. I chuckled as she just shrugged at me and locked her office door. We locked up the main door and got into our cars without another word. I took a deep breath before I started my car and wondered what I had started here tonight. Despite how guilty I felt, I knew I would do it again as soon as I had the chance.

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Written by BoredPen
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