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Real Life

I was my boss's online mistress

A while back in my early 20s I was working in a very large corporation headed by a very serious and uptight CEO. Thomas was a distinguished looking man in his mid 50s and seemed like the type of person that had never done anything out of line or remotely spontaneous in his life. He would never give us workers the time of day except to criticise or complain that not enough work was getting done. Thomas would make us stay back until we had finished all the tasks we had been set and most of us would not get out of the building until well after 7pm each night. One evening I decided to pay back my unpleasant boss by making myself a new work e-mail address, on a different computer no one used, in the name of Mandy. I sent him a slightly racy e-mail telling him how much I was attracted to him and how I would love to be his very own private assistant. Pleased with my revenge I shut the computer down and went home wishing I could see his face when he read the e-mail. The next day, before I went home, I waited until the coast was clear and logged in to Mandy's e-mail address. I was shocked to find an e-mail from Thomas. He thanked me for the e-mail and told me that it was a turn-on and that he would like me to reveal my identity so that we could have a night of passion. Sure that he was trying to blow my cover to sack me, I decided to apologise in my reply and told him this would not happen again. Days passed and I couldn't help myself — I had to check Mandy's e-mails one more time. I was surprised to find two new messages from Thomas. The first message was saying that my real identity was not important and that it excited him because I was mysterious and pleaded with me to write back. The second e-mail had a picture attached of a semi-naked Thomas sitting on his desk wearing just his briefs and a tie. Dumbfounded, I realised this was not a joke or an attempt to sack me; this seemingly boring man had a very wicked side. I continued sending e-mails to him for some unexplained reason and these began to get very hot and heavy and extremely explicit. He sent me more pictures of himself, each more daring than the last and I replied by sending him pictures that I had found in an underwear catalogue. Weeks went by and our online affair continued, I even noticed Thomas was becoming much more light-hearted and animated within the workplace. Finally I knew this had to stop when Thomas wrote and said he had genuine feelings for me and wanted to have sex for real instead of via e-mail. I felt terrible for leading Thomas on just to get my kicks and felt even worse for his poor wife and decided to never e-mail him again — not even to offer him an explanation. I had to leave my job shortly after as the guilt of what I had done hit home. As for the incriminating pictures of Thomas, I decided to delete them instead of destroying his reputation. After all we had been through I felt some strange loyalty to him.

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