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Affair with an employee
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I hired Emily 8 years ago. We would frequently be together at company happy hours and events, but the thought of a physical relationship was always dismissed for a whole host of reasons. Not the least of which was I’m the boss, and married.

The relationship became closer through the years, I always viewed it as a friendship. She had dated a few of my other employees and got engaged to be married. My wife and I would spend time with her and her fiancé, and a few other couples from the company. While we become close that line was never crossed.

Somehow that changed. We were traveling together as we had many times before. It was common for us to go out drinking together and end up in one of our hotel rooms together telling ridiculous stories and having a snack to soak up the booze before our work the next morning. We found ourselves in this situation again.

She was sitting cross-legged on my bed, bare legs ending with her hands in her lap pressing down her dress for some modesty. She was telling me about some girl at the bar we were at that was in to me. She was smiling at how oblivious I was, telling me it actually happened quite a bit. I said something about it being a good thing I’m taken, and it is flattering to hear. I said she was the one that got all the attention. It was the truth, part of what made her awesome at working these shows. Seems like most men (and women) have an affinity for cute, shapely, petite blondes that are easy to talk to, witty and charismatic.

We were drunk, and it was enjoyable to be with her. Somehow we got on the topic of our sex lives. She said her and her fiancé’s was great. I couldn’t reply with the same enthusiasm for mine. It was pretty mechanical. She asked if my wife gave me head, I laughed and said it had been quite some time. She asked if I go down on her, and I said absolutely, but she doesn’t seem really comfortable with that.

I felt it was time for her to share, and asked if she was giving BJ’s to her fiancé. She said probably at least once a week. Without thinking I got up and sat next to her on the bed, placing a hand on her lower back and another on her inner thigh. I told her that she was a pretty amazing person, and her fiancé was a lucky guy.

We frequently had friendly contact, hugs, a hand on a shoulder. This was different. I saw a change in her expression, eyes looking briefly down at the hand on her thigh and then back staring in to mine. Her tongue traced her upper lip before she hit her lower one. She leaned in, her hands let go of her dress, and reached towards me gripping my leg.

It was some of the most exciting, electric, uninhibited sex I’ve ever had. Everything was incredible, from the kissing to her pulling out my cock and saying how nice and big it was, to her blowing me on her knees, taking me deep in her mouth, gagging until I released everything in to her throat to be swallowed up. She was vocal, repeatedly and loudly saying oh yes while I rapidly fingered her. I found she loved it fast and firm, and a squeeze with my fingers all the way in pressing up in to the soft spongy roof while pressing my palm in to her clit caused her to writhe. She gushed. I’d never experienced anything quite like that before. The sheets beneath her were soaked. I gave her no time to recover, flipping her over on to her hands and knees. Standing behind her I entered her for the first time. She was tight like I hadn’t experienced for a very long time. Oh fuck escaped from my mouth as I held her hips and pressed my cock deep inside her. She was just as thrilled with the feeling, moaning and saying oh fuck that feels great.

I went to work, finding a rhythm that seemed to send her to heaven. She gave my hands on her hips full control. Looking down at her ass bouncing, tan lined ass cheeks rippling as my dick disappeared in to her was exquisite. She had so far loved everything we’d done, and I felt the urge to spank her. The first one was firm, but cautious. She responded immediately with a higher pitched yes. So I went again, and again. Her tan lined cheeks became light pink. She started to push back in to my thrusts. Her pussy contracted and exploded with juice again. She ordered me to come inside her and I was happy to obey, unleashing my load deep inside her soon after.

I remembered she couldn’t take birth control for health reasons, and always had sex with a condom. I’d been snipped a few years back, giving me the honor of filling up her tight little pussy with my load. It was all surreal. I pulled out and let go of her hips as she lay flat on her stomach. I saw a big smile on her face, and looked down to see my cum dripping out of her stretched engorged vagina.

We weren’t satiated yet and stayed up most of the night enjoying each other.

That was the start, and it has continued. Every night away and out of town we fuck like rabbits. My wife and I went to her wedding, it was a strange sensation to chat with a man who was marrying a woman that I’d been with just a few days before.

We no longer work together. Not sure when this will end. Last week I asked her to come see me at the office and she eagerly blew me under my desk. We talk about ending it, but neither seem to be willing to say no.

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7 months ago