Dominant Lady Boss

I was getting ready for my date. An unusual event, my boss had asked me out. It was very rare to see a woman lead a big company, but regardless, people were afraid of her. I was not. And even more strange seemed, to me, her sudden interest. I was nothing but a lousy worker at her company, my funds small in comparison to hers. I was used to getting complimented on my looks, but I don’t think that alone won me a date with my boss, who barely even talked to me at the workplace. I tried to not let the nerves get the best of me.

We were going to eat at a fancy restaurant I had never heard the name of. It was not like the rundown places I frequented, or so I hoped. A woman of her caliber would never go to such places, anyway. Chicago was a rather active city at night, and dining was the premiere nighttime activity, aside from fucking. While putting on my cologne, I thought of my boss. A rather tall woman, with long blonde hair and always sporting the latest fashion trends. Her gray eyes struck fear on the faces of those who spoke to her directly, but that was not the case for me.

Maybe it was the way that she didn’t make me uncomfortable that made her want to ask me out? I was used to asking girls out and going out to eat with them, but I had never experienced it the other way around. In a way, I felt kind of helpless but also very, very excited. Maybe if I did well, I could gain a few extra bonuses at work. I put on my shoes, gray moccasins to contrast with my dark blue suit and black tie. I wanted to look very formal and professional. Then, I heard the horn of her car. A Chrysler Model B-70, released just last year. It was not the most expensive, but I know she liked its shape.

I went outside my house to see it, the car waiting for me, my boss waiting inside. Her name was Rebecca. I got into the car in a hurry, not to leave her waiting. “You look beautiful tonight” I said as I looked at her, sitting next to me, one hand on the wheel. “Thanks, you look rather dashing, better than usual at the office” she said in a very calm voice, calmer than usual. Maybe the environment outside the office made her lay down her strong woman façade for a moment, but I still felt her air of authority.

“We’re going to the Green Mill, hope you were not expecting dishes. Everything comes served in a glass” She told me confidently. I had never heard of such place. “A favorite of Al Capone, and mine as well” She said rather calmly. “Don’t worry, we won’t run into any gangster, or so I hope” she finished. “Even if so, it will still be a remarkable night” I replied to her. “You sound rather confident” she said while laughing. I laughed, and light a cigarette, opening the window so the smoke would go out.

The restaurant was quite far, as it was a rather long ride. We spoke about work, our lives, and our favorite cuisine. She was a rather normal woman, despite her richness and responsibilities. When we finally made it to the restaurant, she parked on the V.I.P area. “Perks of being a regular” she said as she finished parking. I got out of the car and went to open her door, I think she was expecting that looking at how she didn’t move from her spot. “Thank you” she told me as she got off her red car.

We got inside the restaurant; it was lit with green lights and was almost full. Smoke was covering the ceiling. “Ms. Rebecca!” the waiter said. “I have your table right here” he said, guiding us to a table by the corner. “Perks of being a regular?” I asked her almost innocently. “This is just the beginning” she said, almost as if she was trying to impress me. Little did she know I was already impressed enough when she asked me out.

We enjoyed live music at the restaurant. We both ordered the shrimp cocktail, under her own recommendation. We had some expensive red wine brought from overseas, and we talked through the entire date. She was a rather complex woman with a lot to say. To finish off, we had dessert; a rather big cheesecake piece for each one of us.

As we were getting ready to leave, she told the same waiter that received us to load it to her account, as she did not want to stop to pay. “I’m in a hurry” she said, in a tone that revealed she was lying. Time passed by slowly when I was with her, and I enjoyed every bit. More than I had expected. “Let’s go to my car” she commanded, and so we did. When we were inside of the car, she asked me if I had enjoyed myself. “Very much. Thanks for the rather unusual date” I said. “It’s your turn to impress me then, let’s go to your place” She had already decided, so I had no time to think about it.

My house was quite small but cozy, with wood walls and a large stone fireplace. We got there faster than when we went to the restaurant, but that was probably because she was driving faster. She had turned on the stereo to some Jazz that was playing, music I didn’t listen to often. “We’re here” I said as she parked in front of my house. We got out of the car, this time she didn’t wait for me to go open the door for her. We made it into the house, and I instructed her to take off her coat and hang it by the door. “You have a quite nice place” she said, in an unimpressed tone. “Let’s see what else about you is good” she said in a seductive tone, and as soon as I turned around, she was topless. I looked at her in shock, this was much unexpected than anything else. “Undress” she commanded, “remember I’m still your boss” she added, with a naughty smile. I started to undress quickly, and stood in front of her, completely naked.

“Good build” she said, walking towards me and unzipping her long skirt. “Better than expected” she said as she knelt down, putting my dick in her mouth. This was turned from a rather unusual date to a very memorable moment. She sucked me for a few minutes, before standing up and sitting down on the sofa, her legs spread open. “Don’t leave me waiting” she said while looking at my body, and I quickly went to her.

I penetrated her pussy in a single motion, and continued to fuck her sensually. She moaned in satisfaction. “You’re good” she said, while I continued to fuck her. I was sweating already. She took my penis out of her vagina, and then stood up. “Sit down” she said quickly, and so I did. She was the one in command. She sat on my penis and started to ride it rather quickly, moving her big ass in all directions. I felt as if she was going to drive me crazy. After some minutes, she stood up, gushing her pussy juice all over me. She knelt down and started to masturbate me with her boobs, which were bigger than I had cared to notice before. She would lick the tip of my penis as it went through her tits.

After a while, I came a big load all over her tits. She proceed to suck my dick, taking out all what was left of the semen. She said, without looking up, “That was very good”. I agreed, then reached to the coffee table to pick a cigarette and light it up. “A remarkable night, you were correct” she said, sitting next to me. “Want a cigarette?” I asked, and she told me she did not smoke. She slept in my apartment, and needless to say, we had a second round that night.

The following day, she got ready to leave rather quickly. “This never happened, okay?” she said as she brushed her hair, looking at myself on my mirror. I nodded. I knew this wasn’t going to be anything important, and that she only wanted a one night stand. “I wasn’t going to tell anybody” I added. “You’d better not” she warned, then stood up and left before I could continue. And that’s the story of how I fucked my boss, and gained nothing more than good pussy. At work, we would barely talk, as usual. It was as if nothing ever happened, but I lusted for her body like I never did before. A woman as bossy as her sure had an attractive aura.