Working Late

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Author's note:

This story is meant to be a fantasy. As such, many points of reality are put to the side, such as safety and pregnancy, as well as others.

Additionally, this story will cover a wide range of sexual activities. I will try to cover them in the into, but please be aware. All characters are at least 18 years of age.

Following comments that I have gotten previously; Everything here is meant for the purpose of telling a story and titillating the reader and is not meant as a portrait of reality. I love hearing from readers, but if you comment that it wouldn't happen that way in real life, well, that's why it's a fantasy.

Topics: TM, oral, anal, rimming, work, boss

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I started a new job about six months back, working as an analyst in a mid sized company. The hours were long, but especially as I didn't really have anything waiting for me outside of work, I didn't really mind. I was part of a small team which made a huge difference to the company, so my work felt like it had meaning. I got along ok with the rest of my team, but being the only guy and somewhat shy, I was always slightly on the outside.

My boss, on the other hand, was a different story. In the six months I had worked for Ms Evans, I came to a couple of conclusions. First, she was an incredible boss. She genuinely seemed to care about the people on her team, beyond the work that they did. She was always willing to teach, mentor, guide and empower her employees. She always gave credit to the people doing the work, and pushed for them to be the ones to present their findings. Second, she seemed to not mind at all when my eyes would accidentally rest on her cleavage. The first time it happened, I blushed and started to stammer an apology, but she laughed it off saying that if she minded people looking then she wouldn't show off so much. I did try to avoid it, but especially while working together a lot, given the size of her chest and depth of her cleavage, it was difficult not to glance occasionally. Each time she seemed to know and would just smile, making me blush and look away. The third thing was that even though I had heard the rumors, I did my best to ignore them, because they really didn't matter. What mattered was that she was a great boss, and I was there to work, not gossip.

It was late in the evening. Almost everyone had left, but I was working with Ms Evans to finish up an analysis presentation that she needed for a meeting with the CEO the next morning. I put the finishing touches on the slides I was working on, let her know, and started packing up my things.

"John, can you come here for a minute?" I heard Ms Evans call from her office.

I headed down the hall and popped my head in.

"Do you have a few minutes?" She asked.

"Sure," I responded, noting that she had taken off the jacket she had been wearing, leaving everything from her cleavage up bare.

"Take a seat, make yourself comfortable," she gestured, standing up to close the door behind me.

Instead of sitting back down in her seat, Ms Evans leaned against the side of her desk close to where I was sitting. Suddenly, I had confirmation of the rumors that I had heard, at I saw the large bulge in her tight skirt that was obviously a cock. I blushed and dropped my gaze. She seemed unfazed and completely oblivious to my embarrassment.

"John. You've been with us now for months. And in that time, I'm sure that you've come to realize that I care about my employees even beyond just work." I nodded. "I also care about work life balance, and while I appreciate it, you have been working a lot of looking hours."

I shrugged. "You know that I don't have much to rush home to. An empty apartment isn't so enticing."

"I feel the same way. But it is important to do things besides for just work."

"It's not like I have very many hobbies. I never liked playing video games that much either."

I suddenly felt a soft finger, that I knew to be perfectly manicured, run down my cheek to my chin and lift my face. She raised my face slowly, making sure that my eyes had plenty of time to traverse the rolling hills of her chest that were even closer with her leaned forward. I felt my cheeks turn scarlet as I hurriedly lifted my gaze to her face. She finally broke the silence with a soft chuckle and said, "then I think we should find you some sort of extracurricular activities."

I froze still as her finger trailed down from my chin, down my neck and chest. It finally stopped when it made contact with my own, shameful erection. She leaned in closer and whispered, "It seems like someone likes the things that they are seeing. But don't worry, your secret is safe with me." Her hand grasped me through my pants. I couldn't stop the small moan that escaped my lips. Embarrassed, I dropped my gaze again only to find myself staring down at her tits again. I was so out of my element that all I could do was close my eyes. "Poor John," Ms Evans said. "Trying his best not to look, even at what is being offered. Let me make this a bit easier for you."

My boss stood up, her hand leaving my crotch to both my relief and dismay. "Is this better?" She asked and I opened my eyes and froze again. Staring me in the face were the most beautiful pair of tits I had ever seen. They were large, but not too big, perky and with perfect nipples. "I know that you have been admiring them. I'm glad. Like I said the first time, I show them off because I like it when people look. But now I want you to do more than look."

I suddenly found my face buried in between those two heavenly mounds of flesh. I couldn't believe that this was really happening as she hummed with pleasure. She held me there for a minute before pulling back. Before I had a chance to say or do anything, she pulled me towards her right side, guiding my mouth onto her nipple. I hesitated at first, but the warmth and softness of her breast convinced me. I suckled eagerly, feeling comforted as she stroked my hair. After a few minutes, she switched me to the other side and I contentedly continued sucking. Ms Evans stepped back so she could lean against her desk, which pulled me out of my chair. Because of the angle my body was at, I didn't realize how much of my weight she was supporting until she let go of my head.

I fell to my knees with a thud. While I was trying to gather my wits, Ms Evans started pulling her tight skirt up. I couldn't help but stare, as inch after inch of milky white thigh was revealed. My eyes followed her hemline upwards and were confronted with a pair of smooth, hairless balls that were obviously full. Following close after came her cock. It was large and erect, pulsing with anticipation as a bead of precum coalesced at its tip. My eyes went wide as I stared at her engorged member. It was a bit longer than my own cock, and a bit thicker as well. I had never touched another person's cock, but I couldn't believe how much I wanted to touch it. My lips must have parted slightly, because suddenly Ms Evans's cock was pressing forward and the drop of precum was in my mouth with my lips pressed against her purple head. Without thought my tongue darted forward and licked the bead of liquid. My boss moaned as I tasted her for the first time. The taste was odd, but not bad or off-putting. As my lips opened even further, I could feel her hands on the back of my head urging me on.

Before I fully processed what was going on, Ms Evans's cock had filled my mouth. I was taken aback, but couldn't deny the sudden rush of excitement. Hands on my head, she shortly started thrusting. It took me a bit before I became a more active participant. As I sucked and licked her, I could feel her getting harder and harder in my mouth. It was a sensation I couldn't get enough of. I continued to eagerly pleasure her, trying to match her rhythm. Ms Evans's moans and the feeling of her fingers tangled in my hair only made me more determined. I was surprised at myself for enjoying it so much, but there was no denying the fact that my own cock was rock hard. Her moans got louder and I knew she was close. As I went to pull my head back as I expected her to pull out, I found my head unable to move. Her grip on my hair had tightened and her throbbing cock had my face pinned in place. I didn't fight it, instead I eagerly continued to suck and lick, feeling her throb once more before a blast of cum filled my mouth. I choked a bit as it coated the back of my throat, but she didn't let up and I felt a second spurt, followed by a third, filling my mouth with her hot cum. I did my best to swallow it down, drinking what felt like a liter of her salty cum.

When Ms Evans was finally spent, she released my hair and I sat back on my knees, feeling both exhilarated and a little dizzy. I took a few deep breaths. While I did, she turned around and pulled up her skirt the rest of the way, exposing her incredible ass to me. I couldn't resist and reached out to touch it, feeling the softness and firmness beneath my fingertips. She placed one hand on the desk for support, and for a moment I thought that she was going to ask me to fuck her. But then she reached back with the other hand and grabbed my face again, pulling me back in, this time towards her asshole. I resisted a bit, expecting her to smell dirty, but she pulled me insistently, and I had very little willpower left. I tried to hold my breath as my face was buried in her crack. I only lasted a few seconds before I needed to breathe. My boss shivered at my exhaled breath on her dark star and then my body took a deep breath of its own accord. Her musky and earthy, not dirty, smell filled my nose. That hurdle passed, it was less than a minute before I gave into her urgings to lick her rosebud. I couldn't believe what I was doing as my tongue swiped and probed at her most intimate spot. I felt dirty but each moan from the beautiful woman above me spurned me on. By the time she let me out from between her cheeks my face was flushed and sweaty and my tongue was sore.

Ms Evans pulled me to my feet and grabbed my belt. I was still a bit lightheaded, and I was so horny by this point I could barely think. She quickly got my pants undone and pushed them and my boxers to the floor.

"Not at all disappointing," She said with a smile as she gripped my cock.

Without me noticing what was happening, she used my cock to pivot me towards her desk. Her hand leaving my erection made me pay more attention, but not soon enough. With one hand on my hip and the other on the top of my back, my boss bent me over her desk. And then I felt it. For the first time in my life, a cock was pressing against my asshole. I groaned as my boss's cock slowly penetrated my virgin hole. I felt myself stretching to accommodate her ass she worked her way deeper and deeper. I couldn't help but let out a moan as she finally reached the hilt. She held me there for a moment before beginning to move. She shifted slightly and my eyes flew open as a jolt of pleasure spiked through my body. I felt my knees weaken as my boss pounded into me, her hard cock filling me up completely. I couldn't believe how good it felt, and I moaned uncontrollably as she fucked me relentlessly. I couldn't believe that the was happening, but I couldn't bring myself to care - all I cared about was the incredible pleasure that was coursing through my body. Every nerve was alight with sensation, and I marveled at how good it felt. I felt my orgasm start to build as my cock bounced with every thrust, dripping precum. I finally felt it crest and moaned loudly as spurt after spurt of cum shot out of me, each timed with a thrust deep into my ass. Even though I had cum, Ms Evans didn't let up or break her stride. She kept fucking me, using my ass for her own pleasure. I expected my erection to go down after my intense orgasm finally finished, but it stayed hard, fueled by her cock inside of me. I had no idea where her stamina came from, but eventually even her breath started to get heavy and I could hear the signs of her impending orgasm. Feeling her cum fill my ass was enough to set me off again as well.

Feeling Ms Evans's amazing tits pressed up against my back as we both caught our breath, was incredible. I could also still feel her inside of me. When she eventually pulled out of me and sat down in her chair, I stood up. My ass was sore, but not enough for me to regret the intense pleasure that it had earned me. I pulled up my pants, cognizant of the fact that they had gotten dirty in the process, but I didn't have anything else to wear. Plus, it's wasn't like anyone would see me. I started to look around to see how I could clean up the mess that I had made, but she waved me off and said that she would take care of it. Not knowing what what to do, I awkwardly said goodnight and headed home.

The following day Ms Evans called me back into her office. She handed me a piece of paper.

"If you are interested in more extra curricular activities then be at this address at 830 Friday evening," She informed me.

I spent the rest of the week agonizing over it, but I showed up at the appointed time and place. I wasn't sure what I was expecting, but an upscale coffee shop was not it. I walked in and say Ms Evans sitting with another woman, drinking coffee. She waved me over when she saw me.

"Lisa, this is John, who I was telling you about. John, this is my friend Lisa. Lisa, I've broken him in already for you. I hope you don't mind if I borrow him every once in a while at work. And with that I'll let you two get to know each other," and with that Ms Evans got up and left, leaving me to embarrassed to even look at Lisa.

Lisa encouraged me to sit and we started talking. Two hours later I was on my back in her bed with my legs wrapped around her as she fucked my ass.

Ms Evans greeted me the following morning with a wicked grin. "I'm glad you had a good time Friday night. Are you supposed to get together again?"

I blushed and nodded. "This weekend."

Over the next few months my late nights at the office started to dwindle. Excepting of course the nights before a big presentation, which was about once a month. And on those nights, I would finish helping Ms Evans gather everything she needed before joining her in her office. Lisa always loved hearing how my boss used my body on those late nights and loved recreating the events in her living room. Six months after that first late night meeting, I moved in with Lisa.

Ms Evans did eventually suck my cock, and she was incredible at it. She also let me fuck her amazing ass, which was everything I thought it would be. But even so, I had found something that I liked even more. I loved Lisa, and I was fully addicted to get cock. I couldn't get enough of it either in my mouth or my ass.