Note: This story was dynamically reformatted for online reading convenience. Archive name: Boss.txt (MF, nc, blackmail, 1st anal wife) Authors name: DaddyMc ( Story title : Nailing the Boss Nailing the Boss. By : Snobbish, arrogant female boss gets caught in a compromising situation by a slightly disgruntled employee and he uses this knowledge to his advantage. Partially True Story M/F nc, blackmail. 1st anal. Being the first person to arrive and last to leave work had numerous advantages. My office was on the 2nd floor with a window that overlooked the parking lot, so I know when my co-workers and the boss arrived and leave each day. The boss is s smoking hot female that spends time in the gym daily to keep her near perfect body in great shape. Anna Jordan's only physical flaw in some men and women's eyes were her smallish tits probably "a" cup but for me it made me want to fuck her even more, because I have a small tit fetish anyway. For a woman that was 44 and had 2 kids both in college she could pass for someone in mid to late 20s. I have spent many a day watching her walk across the parking lot with a hardon and many a night stroking my cock while fantasizing about the things I want to do to her. I even fantasize about fucking Anna when I am fucking, Jessica, Anna's secretary which I have been doing for a few months now. Anna does have another flaw, because she is in a position of authority and commands a 6 figure salary she tends to be a little snobbish and at times acts like she is better than her subordinates, so as a person many of us, myself included do not like her but, like and lust are very different. Because of this attitude it just increases my desire to bend her over her desk and fuck her brains out. Anna's is also very active in her church and attends the same church that the Company CEO does. He is a very devout Christian and active in the church as well. Sometimes I wonder if this may have had something to do with Anna's rapid rise to her current position. Recently a position opened up in our organization that would have been a promotion and pay raise for me, I had the most seniority and experience for the new position so of course I applied assuming I was pretty much a shoe in and all my co-workers assumed the same. Anna decided to hire someone from outside the organization and it turned out that he (Tony) had no experience in the job and I was expected to train him. I questioned Anna as to why I was overlooked for the position and she never gave me a reasonable explanation other than she was the boss and it was her decision. I considered filing an EEO complaint but the Equal Employment and Opportunity office (EEO) here is about useless unless you had definitive ironclad proof or you are a minority. I am a Caucasian male so that left me out. Tony turned out to be useless and very lazy he kept pushing his work off on the rest of us and if anyone complained to Anna she would jump down their throat and tell them to quit whining always defending Tony. So I figured out that there had to be some reason she always defended Tony. To make a long story short I started following her even to the gym making sure she never saw me of course, and low and behold Tony was a member of the same gym and they worked out together. Just this alone was not much of a smoking gun to take to EEO. So I decided to keep up my surveillance for a while longer. One day while board I decided to drive buy Anna's house just on a hunch because I knew Anna's husband, a successful businessman that was required to travel a lot, and I also knew he was on one of those trips now. On the way to Anna's house I noticed Tony's car in a shopping center near Anna's subdivision. Thinking ahead I borrowed a car so it wouldn't be recognized, so I drove on toward Anna's house and when I drove buy I noticed that Tony was walking across the yard to the front door of her house, I stopped down the block where I could still see the house. I then saw Tony retrieve a key from a hidden spot near the door and unlocked the door returned to hey to the hidden location and then entered the house. I was videoing all of this and thought it was very suspicious. I may have enough evidence to take to EEO now but they could come up with a story and there was no real proof just circumstantial, so I decided to use the hidden key and go into the house myself and see if I could get a little more concrete evidence. I waited a little bit to allow them to get into anything they were going to be getting into. After what I believed to be a significant amount of time, me and my video camera headed to the door. I listened outside the door for a bit to make sure they weren't in the living room then entered. As soon as I got inside the door I knew I had my evidence I could hear the sounds of sex coming from a bedroom down the hall. I quietly eased down the hall to the door and peeked in camera recording. Anna was on her hands and knees and Tony was behind her fucking her doggy style. They had their backsides toward me and were so much into what they were doing they were oblivious as to anything else around them. I was getting some good footage of this and then realized they were not in the master bedroom but were in Anna's Daughters room (who was away at college) and Anna was wearing what was most likely her daughter's babydoll nightie with the bottoms removed of course and they were playing a Daddy/Daughter role playing scenario. Anna was saying things like fuck me daddy, I love daddy's cock, Daddy is my pussy better than Mommy's and Tony was calling her daddy's little fuck slut and so on and your pussy is so much better than Mom's. I also noticed that my cock was as hard as a rock and I knew I would be jacking off to this video later. By now Anna and Tony were about to cum too, I decided to record that and then get out of the house and not let them know I was there. Later at home I made a couple of copies of the video for myself. I knew if I showed this evidence to EEO they would know I was passed over for promotion by Anna for her lover and I knew the company CEO would immediately fire both Anna and Tony, their marriages would be over and Anna's reputation would be ruined in the church and community. So instead of going to the EEO or to the company CEO I thought I would show the tape to Anna and let her decide what she was willing to do to keep her life from being ruined. The next evening after work I drove to her house and knocked on the door, she greeted me with normal courtesies and then asks me what I needed. I told her I had a video that is vital that she see she asks what is on it and I said you will understand as soon as she sees it. I think she might have been expecting Tony over again because she reluctantly invited me in and then went in the other room and made a phone call, I heard her say she was going to have to postpone their meeting and would call when she was available. The then looked at me and said business I guess it can wait a bit. The video started out with her and Tony working out in the gym and she started to get a little indignant and angry then ask why are you recording me. I said wait there is more, and then the recording changed to Tony letting himself into her house. Anna started to say something then probably to give some excuse I just held up my hand to forestall any excuse or protest and just pointed at the screen; that is when the bedroom seen came on. Anna turned white as a ghost and looked away from the screen and would not look at it anymore. I told her there was audio that shows you have a little kinky role-play fetish also, would you like me to turn up the volume, she said no and then ask me what do you want for this video. I said initially all I wanted was the job that I should have gotten in the first place and that you to admit in front everybody in the office that you screwed me out of it, but now the more I think about it the madder I get so now I want more. She said what more do you want? I looked into her eyes and said take your clothes off. She was hesitant at first but complied, I made her stand in front of me fully exposed as I looked up and down her tones body, and she only looked at the floor and wouldn't look at me. Anna you have a gorgeous body and I love you tits. You have no idea how long I have wanted to see you naked and how many times I have stroked my cock thinking about you. Why are you turning red there is nothing to be embarrassed about. You pussy is so sexy neatly trimmed like that. Now turn around so I can see that beautiful ass. It was more beautiful than I imagined. I walked over to her and began to run my hands all over her smooth sexy body. She would flinch as I touched her nipples and her small but very firm breast. I ran my hand down and caressed each of her smooth ass cheeks. Anna now I want you to take my clothes off. After we were both naked it told her to again that I had a lot of fantasies about you and if you want to make sure the tape is never seen by anybody else you was going to make those fantasies come true. One of my fantasies is to see my boss on her knees in front of me sucking my cock. Without being told she dropped to her knees and took my cock into her mouth. I grabbed her head and began to fuck her face going deep into her throat; she would gag some but never stopped until I unloaded what seemed like a gallon of hot cum in her mouth. She swallowed every drop. I told her she might as well cancel the "business meeting" she had scheduled that evening because she was going to be occupied the rest of the night. First I am going to eat you hot pussy until you cum and then I am going to fuck every hole you have, first your pussy then your ass then your mouth again. Anna begged; please don't fuck my ass I have never been fucked there. A virgin ass I couldn't believe my luck, I am sorry Anna your ass is too fine not to fuck and knowing I will be the first makes me want it more. By tomorrow morning you will never again be able to say you have a virgin ass. And it's going to get fucked a lot as a matter of fact I am going to fuck you ass first now instead of anything else, so get in the bed and get you on your hands and knees. With tears in her eyes she looked at me and said please not my ass I will do anything else. You are going to do everything I tell you anyway because you are my slut now, but if you don't resist I will go slow so it won't hurt as much the first time your ass get a hard cock in it. I could see the realization in her eyes that she knew I had the upper hand and she was a sex toy for one of her employees/underling to use as he wanted. She ask how long she will have to do this with me. Until I get tired of you was my response, and if you please well enough and corporate I won't loan you out to my friends. I took her to the bedroom; now get on your hands and knees with that hot ass facing me. Still sobbing she complied. I came up behind her and spread her ass cheeks so I could see that virgin asshole. I couldn't help myself I has to lick it and then tongue fuck it first to lubricate it some. After a little bit if this Anna lit out a moan and seemed to be enjoying it. Then I got on my knees behind her and but the head of my cock at the entrance to her ass and slowly started to push forward I felt her tense up and start to cry again. You have to relax so this won't hurt as much if you don't it could be very painful for you. She forced herself to relax then the head slipped in, oooohhh your ass is tight, then I could help myself, I grabbed her hips and shoved as hard as I could slamming my almost 8 inches of cock all the way in her as hard as I could. Anna screamed in pain and I pulled back and slammed her ass again then started fucking her as hard and fast as I could. Anna was crying, screaming and begging me to stop because it hurts so badly. She tried to get away but the harder she fought the harder I slammed into her tight ass. Luckily for her and because her ass was so tight and I was so turned on I was about ready to cum fairly quickly, so I told Anna her comes you first load of hot cum in your ass. Then I emptied what felt like another gallon of hot cum in her tight ass. I pulled my cock now beginning to soften cock out of her ass and she collapsed on the bed still whimpering tears still running down her cheeks and cum dripping out of her violently violated ass. After a few minutes she began to recover. She looked at me and said you told me you were going to go slow but you didn't. Well a while back you said you were going to give the promotion to the most qualified person so we both lied. Now clean my cock off with your tongue and the suck it till I am hard again because I still haven't fucked your pussy yet. Around 3:00am after fucking her pussy and her ass again I got ready to leave and go home, but before I left she ask how she was going to explain the sudden job change to the rest of the office. I said don't worry because is sent Tony a short clip of the video I made and said that if he didn't want his wife to see the rest of it, he needed to resign which would open the position back up to put the most qualified person in it. Don't think about plotting some type of revenge because I have things set up that should anything happen to me packages will be delivered to your husband, your church and every employee at our company including the CEO. Oh yes one final thing I will be back this afternoon and I am bringing Jessica, your secretary, I have been fucking for a few months now, I hope you like eating pussy, Because since you treat her like shit Jessica has been dying to make you eat her pussy for a long time and I am looking forward to watching you do it. Anna's eyes filled with tears again. End *************************************************************************** ** This story was written as an adult fantasy. The author does not condone the described behavior in real life.