tagErotic CouplingsCaught Masturbating

Caught Masturbating

byedmead©

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.

Just then Angie got up and straddled the chair, pushing my hand away from my penis. I almost fell backward and grabbed her so that the chair wouldn't fall over. She landed on my lap and my penis was pressed against her wet labia. Angie started moving back and forth, the pressure of her labia pressed against my penis. I was shocked and didn't say anything for a couple of minutes. It felt good and I just let her keep going. My senses returned and I started to push her away and told her we couldn't do this.

As I pushed her away the angle of her body and my penis changed and I could feel my penis pressing against her the opening of her vagina, if I wanted to have intercourse with her it would have taken a simple movement and I would have been deep inside of her. Of course I wanted to get her off of me, not get her 'off'. But just as I was about to escape I felt myself ejaculate. One pulse and a stream of my semen shot across her labia, I looked dead into her eyes and as she registered the heat of my semen her eyes got wide and she gasped. Instead of pushing her away I froze, I didn't move leaving her dangerously exposed to my penis. My hot semen was mixing with her juices and it felt amazingly wrong. I wasn't supposed to be here doing this. How did this happen, I asked myself.

She leaned forward to hug me and the tip of my penis slipped just inside of her. There was a feeling of inevitability when I felt her moving so that my penis would penetrate her deeper. I wasn't going to be able to overcome the inertia and before I could do anything a stream of my semen filled her as she moaned loudly. I flinched realizing I had just crossed a line; I had to pull out before I came again. Angie was too big for me to stop her from scooting forward and I slipped even further inside of her just as my penis pulsed again. I tried to pullout, but she took it wrong. She thought I was trying to stroke back and forth. She let go and leaned back riding my cock up and down as the last of my semen filled her.

It was all over for me, but for Angie it was just starting. When I tried to stop she looked at me sternly, "not so fast, you don't get all of the fun." I started to get soft, but Angie didn't stop riding up and down. I watched her heavy breasts bounce on her chest. As my eyes floated upward I looked into Angie's face, her swollen lips were open and wet and she was staring into my eyes. My hands found her hips as she leaned forward and kissed me. I held onto her as I kissed her back, my hands gripping her body as my erection returned, this time harder than before. Angie could feel I was hard and she stopped kissing me so she could ride my penis faster. Not long after she told me she was having an orgasm. As she climaxed she kissed me again. I was surprised when I felt myself about to climax. Angie stopped moving, leaving me inside of her as she kissed me. My eyes were wide open as she kissed me with her eyes closed and before she was finished I began ejaculating inside of her again. Her eyes opened as she felt my semen inside of her. Tightening her arms around me she squeezed her vagina to milk the last drops of semen I had left. Angie climbed off of me, smiled and left.

Oops. That didn't go as planned.

The next afternoon Angie stepped into my office, closed and locked the door behind her and walked briskly to my desk. She shoved her clenched hand to me and said, "You have to wear this, I don't think I could get pregnant, but I am not on the pill so we have to be careful."

I took the condom from her hand as she began undressing. Before I had thought about what to say she had her shirt off and was mid-way through removing her skirt she said, "Well don't just sit there, we have to hurry, I have a PTA meeting to get to."

Angie was naked when I stood up. She grunted in frustration and began helping me unfasten my belt. I gave in and soon we were both stood face-to-face completely naked in my office. I was already aroused as Angie took the condom from my hand and helped me put it on. Once it was on she began kissing me and I kissed her back. Moments later I was laying on my back with Angie riding my cock once again.

Angie was very efficient. She had two orgasms before I was even close to ejaculating. She told me to get on top and she laid back on the floor, spread her legs as I pressed my semi-erect penis inside of her. With each thrust her breasts flopped on her chest. She was definitely more attractive on top than on bottom. My penis became less and less erect until the tip of the condom got caught in her as I pulled out. I removed it and told her I was done. She could tell I was lying. She pushed me backward and began sucking my soft penis. It didn't take long to get hard again. Once it was hard she began kissing my stomach, then my chest and finally my lips. She positioned her vagina over my penis and began rubbing up and down as I got harder and harder. Soon I was hard enough that on the backstroke my penis slid inside of her.

We were fucking again, her breasts were hanging heavily over me and I was feeling the urge to come. I told her, "I am about to cum we better stop."

Angie stopped, sat back and asked me to ejaculate over her vagina. She laid back and began fingering herself. I got on my knees and began jerking my cock over her. She told me to get closer. The position was uncomfortable, but I tried my best to please her. She began begging me to cum. I was becoming more and more aroused as she begged. She lifted her hips to bring her vagina ever closer to my cock when a big drop of precum formed on the tip of my penis. She asked me to rub it on the lips of her pussy. When I did she begged me to cum inside of her. I kept rubbing the tip of my penis between her lips as long as I could, but just before I was about to ejaculate I let go and rammed my cock deep inside of her.

Angie wrapped her arms around my shoulders and whispered, "Cum, cum, cum inside of me."

Just as she did I ejaculated. We both verbalized the experience in grunts and moans.

Just as quickly as it had started it was over. Angie was off to her PTA meeting.

For the next few weeks Angie and I had sex almost every evening, never again with a condom. I assumed she had started using the pill until she told me we had a problem...

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