Me And My Sexy Boss

Me And My Sexy Boss
This is a story about me and my sexy boss that I slept with on numerous occasions. I was working at a private accounting office in downtown Chicago. My boss was a beautiful, sexy, 5’7″, with nice round ass and big tits. She was 25 and I was 20 at the time. All I dated back then were married women; it was just the thrill of knowing that I can get them into bed. Most of the time when you work in a place like that, you would know about the office tramps. But I did not hear anything like that about her, just that she was hard to please when it came on to work and she was married. Anyway, one day she and another co-worker were talking in the hallway and I just happened to walk by when she said, I never dated guys that were shorter than me. Take for example Ricky; he is shorter than me so he can’t do anything for me. Me with my male pride could not let this go with out saying something. So I replied, what does that supposed to mean? She calmly replied; Small guy, small package. Really, how would you know? Well, I just look at the size of their hands and shoe and that is how I determine what type of package they have. Take for example my husband, he is 6′ and he has a huge package. I had this puzzled look on my face and said; so you think that because I’m only 5’6″ and my shoe size is not a 12, I have a small dick? With a shocked look she smiled and said yeah. So needless to say that I informed her that is not entirely true and she curiously ask; Ok then, what is your dick size? Its 10″ long and 2 and half inches thick. Yeah right, you are just trying to impress us. As the conversation gets heated we move to her office, and seeing that there are two females and me, I’m out numbered in this conversation. The other co-worker really did not say anything but just sat there and agreed with what my boss saying. As soon as we get to her office and sit down she says; Boy I would break you in half. I smiled and said to her; you think you can, but I don’t think you have the guts to find out if you can break me in half. She leaned back in her chair and said; If that is a challenge I do not back down from them. Well, then lets see how true you are to those words. Boy, you cannot keep up with me; I will ware you out and then talk about you bad at work. Sounds like a bunch of talk to me. After about five more minutes of us talking trash back and fort we ended up making plans to meet at one of the hotels in downtown Friday night because her husband was going out of town for the weekend. She ask me to get the room, because her husband did the books and she did not want to explain her spending so much money on an hotel room without him. I was single so I did not care. We really did not talk about what was going to happen Friday night that day, except when we got off work she said to me; You have something to prove to me in a couple of hours so I will see you then. I said; I guess I will see you in a few. We both left work at around 4:30 and went home. I went home and took a shower and changed into something a little more casual and got the room at around 6pm. I got into the room checked it out and waited for her to show up. I really had a slight doubt about her showing up and started to make plans in my mind just in case she did not show. I never had a girlfriend and I knew a few girls that would not mind me calling them for some Friday night fucking. I said to my self I would give her until 7 pm and then go to my back up plan. While I was watching television I heard a knock on the door around 6:45 and when I opened the door it was her. She was wearing, this long blue jeans skirt that was right at her ankle, with a split on either side up to her thighs, and this pink “V” neck blouse and black heels. As she walk by I was checking her out especially that amazing ass shaking in her jeans skirt. She put her purse down on the bed and sat across from me on the couch in front of the television while I sat with my back to towards the television. She then looked at me and said; you look very nice. And I replied; you look stunning. Hey that was the idea. I was wearing one of my beige slacks and a polo shirt. She then looked at me and said; I had doubts about tonight. What kind of doubts did you have? I did not think that you were going to show up, hell I did not know if I was going to show up. Well I had doubts about you showing up and had a back up plan. Really, she said. Oh yeah, I always have a back up plan that you should know about me. She then gave me an indication that she wanted to get things started by uncrossing her legs and giving me a peek at her pussy and then crossing it again. I got a nice look because she was not wearing any panties. As soon as I saw that my dick started to get hard. I instantly got up and joined her on the couch. She then kicked her heels off and placed her legs in my lap. I then began to massage her feet. She had nice soft and beautiful feet so I could not help but to massage them. As I took one of her feet, she uses the other to massage my dick as it continued to get hard. As it’s getting hard she takes a peek and she had this surprise look on her face. She then says; May I take a look at your dick? Without any hesitation I unzipped my pants and let it out. Wow, that looks just as big as my husbands. She seductively licked her lips and removed her legs from my lap and reached down with her tongue and started to lick the head of my dick. She did not waste any time taking it into her mouth while reaching down with her fingernails and slightly rubbing them up against my balls. As she continues to suck my dick, I grabbed her head and pushed it down slightly, while she moves to the floor and gets on her knees. I continue to push her head down and she looks up at me with approval of me pushing her head down on my dick. Her head continues to go up and down as she is sucking the hell out of my dick.

After a few minutes we move our action to the king size bed. I got up and removed my clothes and left them on the floor in front of the couch. She removed her blouse and her bra, and used her index finger to call me to the bed. As I walked up, she grabbed me and pushed me down on the bed, pull her skirt up and sat on my face. Her pussy was so wet; as I was licking it I could feel the juice dripping on my tongue and oh man did it taste good. After a while she turned around and started to suck my dick while I eat her pussy. The foreplay lasted for about five minutes and that is when I realize that her pussy was shaved clean. I thought she had a little hair on top, but when she removed her skirt I saw different. She climbed on top of me and started to ride my dick and moan loudly. I can see her ass shaking while she rides my dick. I could not help myself, so I grabbed a handful of her ass and started to slam her pussy down on my dick. As I did that no sooner, I heard her say; Oh shit Ricky, I’m about to cum. She let out a huge passionate scream with her head tilted back and her hair dangling down the middle of her back. She then said; I want you to fuck my pussy hard with my legs in the air. We both got up and she got on her back, I then grabbed her legs and spread them as wide as they could go in the air and started to stab her wet juicy pussy. My dick was going in and out of her pussy while she continued to scream and moan. The more she scream and moan the harder I fucked her. To my surprise she said again; Oh shit I’m about to cum again Ricky, fuck my harder. I obliged her and fucked her even harder. During the next 30 minutes she had four orgasms before I exploded on her tits. We were both sweating and breathing heavily and that’s when she said; I have never been fucked like that before, and I have never had an orgasm four times in one night. You are fucking great. I then said with a smile on my face; I aim to please and you are not the first to tell me that. She turned and looked at me with a smirk and said; You are one cocky son of a bitch. No I’m not cocky, just confident and good at making a woman feel good sexually. I then got up and went to the bathroom with my dick still hard and took a piss, while she came in behind me and washed the cum off her tits. As soon as I was done I went back out and go on the bed. As I lay on my back, she walked in and said; I can’t believe that I’m saying this but I’m ready for round two. She got on the bed and started to suck my dick again. My dick was still fully hard as she continue to suck. She gagged as she went down a little too far, but she regained her composure and started to give me an even better blowjob than before. After a while she got up and got on her back with her head hanging off the bed. I got off the bed and stood with my dick where her head was hanging and started to fuck her mouth. As I was doing that, she grabbed my ass and helped me stuff my entire dick in her mouth. She gagged a little but that did not stop her from a 10″ deep throat. She was sucking my dick so good, I could not help it, after about 5-6 minutes I exploded in her mouth, and to my surprise she loved it and took every drip of my cum in her mouth and swallowed it. After, I nutted in her mouth my dick was still hard and ready for round three, which was normal to me. I climb over her and got on top of her and slowly push my dick inside of her pussy. After teasing her for a minute I started to fuck her nice and slow. Then she said; Oh baby just what I need a slow long screw. I smiled and said to her; That is what you are going to get. As I fucked her nice and slow, she was calling my name. I have had girls call my name before but not like her. She was calling my name in a very lustful and seductive way and the more she called my name the more I wanted to fuck her and it did fuck her as she boasted my male ego some more. This went on for another 30 minutes and she had multiple orgasms again. This time I nutted while titty fucking her and she sucking my dick while doing that. I nutted all over her face and some got in her mouth. We must have fucked about four to five more times that night before we went to sleep and I guess we full from sex because we did not eat until the next morning. The next morning while we were talking about our evens that happened the night before over some room service, she told me that this was her first time having sex with someone shorter than her and she would never think that shallow again about the size of someone’s package. She also told me that this was the first time that she had ever cheated on her husband, and the things that happened to her that night had never happened before. She said she has never been that horny before, never swallowed her husband’s cum, never fucked that long before and never had that many multiple orgasms in one night and never fucked that many times in one night. After that night it became a regular thing for us, but sometimes we had to improvise. Most of the time it was after work in her office and a few times before in the same spot. Sometimes she would end up at my place. I kind of felt bad after a while because I met her husband and he was always talking to me. One day I asked her if he knew what we were doing, and she told me he would kill her if he found out. She even went as far as telling the other co-worker what happened that Friday night. I was kind of mad because I am a very private person when it comes on my sex life.