I was a young attorney, working during my first year after law school at a small firm in Los Angeles. I stayed pretty busy most of the time, doing the normal lawyer thing. Jill was a legal secretary whose work station was just around the corner from my office. I got to know a few things about Jill through casual conversations here and there as I passed by on my way to another office, or the copy room, or wherever that gave me an excuse pass by and get a look at her. She was in her early-forties, which was nearly twice my age, but there was just something about her I found irresistibly attractive. It didn't hurt that she was tall with an incredible figure, not the least of which were her ample breasts that she always managed to show off just enough to make them impossible not to look at, and yet always came across as elegant and professional.
Sometimes passing by Jill's station I would catch a glimpse down her partly open blouse and my hormones would be off and running. Some days it drove me so crazy that I would have to go to the bathroom and jack-off just so I could get back to concentrating on work. But there was something more to Jill than just her beauty; she had a way of making everyone feel as if she was very happy to have them around her. I also knew that she was a single mother of a 12-year old boy, which meant that she never stayed late at the office, much to my disappointment.
Being in a small office, it was rare that anyone besides me stayed late. The older attorneys who had better things to do rarely stuck around past 5:00. I often found thoughts of Jill coming to mind, and I would inevitably start to surf the web, looking for some porn that resembled Jill. I never found any, but the thoughts of Jill and the images that flashed ceaselessly across my screen would make me so horny that I had to stroke myself through my pants. When it got too much to bear, off to the bathroom I went to get some relief.
I usually kept my door closed during these sessions, but of course one night I just didn't think about it. My rock-hard shaft formed a huge bulge in pants, and the pre-cum had made a little wet spot on my khaki trousers. At the last second I heard someone walking toward my office and quickly minimized the porn on my computer screen, and tried to look busy. I was shocked to see Jill walk past my office, then stop and come back to the doorway. I quickly tried to assume a casual position while at the same time trying to hide the bulge in my pants that had just gotten even bigger.
"Hi James." she said in a less than happy voice. I had never seen Jill in casual clothes before. Despite the fact that we had "Casual Fridays" around the office, she always dressed professionally. That night though she was wearing a light summer dress that only came down about mid-thigh and had a low neckline, and stood out beautifully against her tan skin.
"Hey Jill," I tried to respond in a cool voice, but I could feel my voice start to choke and my face was on fire. Partly from embarrassment at almost being caught, but mostly from the thousands of Jill-fantasies running through my head that had started out just like this. "What are you doing here so late?"
"Bill has me working on a big project, and I'm a bit behind. Today I had to leave early to help Derrick get ready to leave for a long weekend with his father. So now I'm back to try and play catch-up. What are you working on?" As she glanced down from my face toward my desk to see what I was working on, I could see that she notice my bulge and probably the wet spot too. She quickly looked away, with a mild look of embarrassment playing across her beautiful features.
Damn it! My face burned even more. I quickly adjusted my position in my seat, and patted a pile of paperwork next to me. "Oh, you know. Just the usual."
"Right. Well, I'd better get to work," she said with smile, "and let you get back to yours." There was an odd emphasis on the last part of her statement as she turned away to head for her desk. I wasn't sure if she was encouraging me to get back to work, or get back to taking care of my now raging hard-on. The possibility that it was the latter sent my brain buzzing.
I decided to wait a bout 15 minutes, then pretend to take something to the fax machine that would take me past Jill. She was leaning forward in her seat with her elbows on her desk, which pressed her breasts together and the caused the neckline of her loose dress fall open, giving me an unprecedented look at those gorgeous tits. Electricity shot from the top of my head strait down to my cock. She looked up as I walked by and smiled, but neither of us said a thing. My gaze had lingered longer than I had intended, and I knew she had noticed where I was looking.
I went to the fax machine and typed in the fax machine's own number. The fax started to go through and I racked my brain trying to figure out my next move. This was not like picking up a girl at a bar, or even at school. This was a whole new league, and I was a rookie player. I thought about offering to get us some dinner, but no doubt she had eaten before she came in. I decided to just jump into a conversation and see where it took me. On the way back to my office I stopped at Jill's desk.
"I hope this isn't too intrusive, but you didn't seem too happy when you first came in. Anything other than just not wanting to be at work on a Thursday night?"
She smiled softly as she looked down at her desk for a few seconds in silence. I was about to apologize for bothering her and leave, but she said, without looking up, "I'm alright. I just..." she stopped herself with a long sigh. She gave a light laugh and looked up, "You know, just old lady stuff. Nothing that would interest you." She carefully maintained her slightly strained but still sweet smile.
