[Taurus44]

Over 20 years ago, I applied to and was hired by a defense contractor for swing shift operations in the data center, and then later moved to graveyards. It was a good job for someone in college as I was. My Boss, let's call her Elaine, was a "large" lady, about 5'6" or 5'7" and pushing, if not a bit more than, 200 lbs. She was probably 15 to 20 years older than I. Shortly after I got hired, she was working on a problem at one of the terminals, she stood there, bending over the back of a chair with her dress on and she was of such a size that the back of her dress rose up enough to see more of her legs than I really cared to see. But since I'm a voyeur and she was wearing pantyhose, my Kryptonite, I took it all in as much as possible.

I year or so later, Elaine had gone on a health kick and she and I would play racquetball all the time. At first it was me running her all over the court, but with time, she became quite accomplished and I had to bust my ass to beat her. She also dropped about 60 lbs. Now this mid-40's woman not only didn't look all that bad, she was pretty hot.

One Saturday night she came by work to check and see if there was anything I needed. She was dressed in a parrot blue silk shirt, black leather mini-skirt, black pantyhose and black pumps. She looked totally Fuckable. I guess she must have caught me more than once ogling her. By this time we had a very strong friendship and I had no problem telling her that she looked very nice. I asked her what the occasion was and she stated she was going to dinner with her accountant, I told her he was a lucky guy and she blushed. As she was walking out of the data center I hung by the door and watched her walk down the hall. I gave her a wolf whistle, I couldn't resist. She turned, saw me checking her out top to bottom. Then she asked, "Would you rather I stay here?" I will regret this answer for a long time, I told her, "No, you'd better go, I won't get any work done if you stay." She actually looked a little disappointed, shrugged her shoulders, turned and left.

Stupid Stupid Stupid Stupid Stupid...

I could have totally boned my boss that night but passed on the opportunity. I'd be lying if I said I haven't jerked myself off thinking of how that evening would have gone had I asked her to stay. Oh well, what's life without some regrets?