For the past eight years I have run a small technology company with twenty-five employees. Early on I had big plans for the company, but over time I have been more and more satisfied running my small, sleepy little company. I make a good living; have a great family and very little stress. Last year my wife recommended that I hire someone to help me as our kids were getting older and required more and more of my time. I never really liked the idea of an assistant, but I had to agree that it would allow me even more time with my family. My wife isn't the jealous type, but I decided early on that I wouldn't hire anyone I was attracted to.
It took six interviews, but I finally found the perfect assistant. Angie was forty-two, short and overweight. Of course, she was perfectly qualified for the position and I made her an offer. No one, and I mean no one, would assume anything untoward was going on between me and my assistant. Everything worked out well for six months.
I have this nasty habit that I had kept secret for years. With the kids and all of our activities my wife and I don't have as much sex as we used so I am consistently in need of a release. On occasion, after the offices closes and everyone else has gone home, I surf the internet looking for pornography and masturbate while looking at the pictures I find. It is too hard to masturbate at home with the kids and the wife running around, so the deserted office is my last private place.
One month earlier my sales manager hired a very attractive sales representative. I had thought about her more than a few times while getting off, but it was only recently that I had a picture of her. Well, it was a picture of the only three women who work at our office and included Angie. On one particular evening I pulled up this picture on my monitor and began masturbating at my desk. I thought I was all alone, but just before I ejaculated I heard someone. Turning my head I saw Angie standing in my doorway with her mouth wide open. I turned away and pulled up my pants. Red faced I apologized and she ran out of my office and was gone before I managed to catch her.
I was so embarrassed. Would she come back to work tomorrow? If she did would she tell anyone? I was just a little worried. The next day Angie was at her desk when I arrived and she acted as if nothing had happened. I asked her to come to my office when she had a minute, but before I had a chance to say anything she said, "Don't worry, I am not going to say anything. You aren't the first man I have caught doing that, I have three teenage boys at home." Relieved I apologized and everything seemed settled when Angie smiled slyly and winked at me.
On Monday I got worried. Angie sent me an email with a picture of herself in a sexually revealing outfit and a note saying, "Thought you might like this picture better since it shows off my assets better. You aren't the first boss who has been attracted to me." Oh shit. She thought I was... Of course I was freaking out. What should I do? I could tell her I was actually thinking of Julie, but that might not be a good idea. What if she told her? I decided to simply tell her that I had made a mistake and that I thought it would be better to keep our relationship professional.
I waited until closing time and asked Angie to come to my office. Most everyone had left and closed the door. Angie seemed a little uncomfortable so I jumped right in. I explained that I made a mistake, that I was embarrassed by my actions, that I valued her contribution to the company and that I wanted to keep everything professional. Angie was offended. I couldn't figure it out. She stood up and started yelling at me. Somehow she took my apolgy as a rejection. She explained that it wasn't HER who did anything wrong. That she wasn't interested in a sexual relationship. It was me, and to now explain to her that I wanted to keep everything 'professional' was ridiculous!
Her voice calmed and she said, "I don't mind if you want to masturbate to my picture, it doesn't bother me, actually it gave me a self-esteem boost. Ever since my husband divorced me I have been self-conscious about my looks. The fact that you are attracted to me doesn't mean I am attracted to you. It doesn't mean I will have sex with you. Don't make this about me, it is about you and your fantasies."
Oh my God, I thought to myself. She doesn't get it! I told her I understood and she left. I sat there for an hour trying to figure out what to do. When I finally went home my wife noticed I was stressed out. I didn't want to talk about it.
The next day Angie was wearing a low cut shirt and a fairly short skirt. Her hair was groomed and her makeup was well done. I could tell that she had been an attractive woman in her twenties. Now she was older, overweight and unattractive. She didn't act strange. It was if our conversations never happened. But after work she stopped by my office and asked if I had 'used' the picture she gave me. I stood up and treaded lightly suggesting that I didn't think that would be a good idea. She started to get angry again. Finally she suggested that she was uncomfortable with dishonesty. She felt it was dishonest to masturbate to her picture secretly. It seemed like she was trying explain that just because she knew about my behavior I didn't have the right to stop. In a round about way she explained that the price I should pay for using her image was to at least give her the credit by at least telling her thank you.
Without much of an option I thanked her for letting me use her picture to masturbate to. She took my half-hearted thank you as an admission that I HAD in fact used her picture to get off. With a bounce in her step she turned and left my office.
The next morning another email was waiting for me. Angie had sent another picture, I didn't dare open it. This wasn't going to end well I could tell. That evening I sat at my desk after everyone had left and opened the email and the picture. The picture showed Angie on her bed completely naked. Ironically I thought she looked relatively attractive in the picture, surely she could find someone. Why me? Ug. I leaned back in my chair and closed my eyes as I thought about my next move.
Just as a did I heard someone in the doorway clear their throat, it was Angie. When I turned she smiled and said, "I am sorry if I am interrupting anything." I tried to close the computer screen but she walked over and pushed the mouse away. She said, "No don't stop, I want you to." She had her hand over mine on the mouse and I pulled away. She pulled the picture back up and said, "I want to watch you masturbate." That wasn't going to happen and I told her so. She began to cry. Uncontrollably. She then started talking wildly. Eventually saying she was going to tell my wife unless I did.
I tried to calm her down, but she insisted. Either masturbate right now, or she would follow me home and talk to my wife. Nightmare. Without much choice I agreed. I told her this would have to be a one-time thing. That it could never happen again. She agreed. I unzipped my pants and began rubbing my penis. It wasn't getting hard. I kept trying and trying, but I wasn't aroused. The fact that she was there and that she blackmailed me was a definite turn off.
Angie lifted her skirt and took off her panties. She said, "maybe this will help." Sitting on the edge of my desk she began fingering her vagina in front me. I could see and hear how wet she was. When she pushed and pulled her finger and out I heard slurping noises. Part of my brain kicked in and I thought about ramming my cock in her wet hole. She was right, all of the sudden I was aroused watching her finger herself. I began stroking my cock in front of her and she moaned as she saw it grow. She unbuttoned her shirt and unhooked her bra showing me her breasts. I was turned on, but I wasn't getting closer to climax. Five minutes, ten minutes, twenty minutes, forty minutes and I still hadn't cum. Angie was starting to get annoyed and I was getting frustrated.
