Admin Assistant

I am a middle manager for a rather large firm. In my organization, it is common for a person in my position to have a person that acts kind of as an administrative assistant. This person handles all of the administrative responsibilities for my division to include budget and supervising the admin staff. The position reports directly to me and as a result spends a lot of time with me. I had recently had that position come open and I started to recruit for a replacement. Several people from the organization put in for the job to include a lady that I had worked with before, had a great reputation and quite frankly I considered a friend. I conducted a selection process and due to her experience and background this lady, who I will call Linda, came out ahead and was selected for the position. As soon as she came over and started in her new position, we hit it off and rekindled our friendship. I knew her husband and she knew my wife so we talked often, not only about work but often of personal things.

As time passed we found that we spent more time together and due to the numerous work related projects we were working and the distractions in the office, we often had lunch together. One of our favorite places was a Chili's restaurant that was nearby. Now, I'm not really sure how it happened but as we started to talk about some personal things one day on a lunch run to Chili's, the topic of voyeurism and exhibitionism came up. She admitted to enjoying voyeurism at times and I admitted to being somewhat of an exhibitionist but that I had really never had the opportunity to pursue it. Somehow the conversation turned to my fantasy of being able to jerk-off in front of a woman and she told me a story about time she had watched a guy she knew. Somehow it progressed to her being willing to watch me some time if I wanted her to. I can't really remember the details of the conversation as I was so excited and turned on that most of the afternoon was a blur.

Now let me tell you that she is about my age, in her late thirties and does exercise regularly. She is a very attractive woman with absolutely amazing breasts that I had fantasized about. She is a lot of fun and her open demeanor about sex and her appearance makes her very sexy. I jumped at the opportunity and by the end of lunch we agreed that we would both stay late and that she would drop by my office after everyone had gone home and we would have a "closed door meeting". We actually exchanged text messages all afternoon confirming the meeting and making sure we each wanted to go through with it. We were clearly both nervous about it but I was so turned on by the thought of this very hot woman watching my get hard and stroke myself to orgasm that I couldn't turn it down. The time finally came and she came into my office with a note pad and asked if I still wanted to meet. I told her there was no way I would pass this opportunity up and told her to come in and close the door. She came around behind my desk and sat in a chair that was about 6 or 7 feet away from mine. I was shaking beyond belief but so horny staring at her very hot body. I could not believe that this was about to happen. I made sure she was alright with this and then stood up and started to undress.

I can still remember how much I was shaking and how my stomach was so nervous. When I finally slid my shorts down and sat down, I looked up at her and she was staring at my naked body. I remember how hot she looked and how horny it made me that she actually looked turned on staring at my cock. I started to touch myself, playing with my balls and with my cock and quickly got hard as a rock. She just stared as I waved my hard cock at her and played with my balls. She commented on how beautiful I was. I will never know if she was lying to me but she mentioned that I was bigger than her husband. I don't know how truthful that was but she sure knew how to make me horny. What guy doesn't like to hear a hot woman tell him how big his cock is? She just kept talking to me and staring at my dick. I was so hard and I knew that I would not last long. I couldn't believe that she was actually sitting across from me watching me play with my hard-on. She looked so good and I so wanted to hold her amazing breasts feeling her nipples grow hard in my mouth and then diving in between her legs and nibbling on her clit until she came but, the agreement was no contact so I continued, knowing I wouldn't last long. I just kept imagining what it would be like to bend her over my desk and hold her round ass as I slid all the way inside her. I couldn't believe the amount of pre-cum that was coming out of the tip of my cock and how hard I was. This was the most turned on I had ever remembered being and the harder I grew and the more pre-cum I produced, the hottest part was that she was watching. My hand continued to slide up and down my cock. Now I don't think I'm huge but every bit of my seven inches wanted her. I could feel her eyes on my hard dick and knew I had to explode soon. I couldn't decide whether to stare at her huge boobs or her face as she stared at me.

I also knew I had to cum and I was so horny knowing she was going to watch my cum explode out of my cock that I couldn't hold back any more. I told her I was gonna cum and she made some comment about cumming for her and I couldn't hold back. I shot my cum all over my hand, cock and stomach, not wanting to make too big of a mess in my office. But having her watch gave me one of the best orgasms of my life. She just watched me finish with a sly smile on her face and I couldn't help but hope that this would not be the only time.

We had a few more experiences before she changed jobs and I then moved on. I really missed her and the fun we had. Recently we had the opportunity to see each other again and we still felt the bond of our past friendship but due to some things in her life, she didn't feel comfortable rekindling our "special" friendship. I still jerk-off thinking about her and those times we had. She is till very hot and I still so want to see those amazing boobs but I would really enjoy the opportunity to play for her again. I have offered to come to her place and bring coffee and bagels and serve them naked but, to no avail so far. I think she is an awesome woman so I value our friendship but so wish she will see the harmless nature of our little game and just let us both enjoy it. She is a very sexy woman and turns me on incredibly. I expect to tell her about this tory and hope if she reads it that it motivates her to reconsider.