Sidewalk sex [MF]

Another story from many years ago…

This took place while I was at a week- long conference in a mid-sized Canadian city. One evening after the training all of the people in our training group went out to get drinks and decompress. So far we hadn’t had a chance to get together like this so we collectively were all ready to let loose.

One of the girls in the group was named Carla and I could tell during the training that she had a crush on me- I would catch her staring at me or she would laugh a little too hard at my jokes. She was very nice but not really my type physically – although she had red hair, she was a little on the plump side and very over-sized boobs. Anyway, a nice girl.

During the night out, most everyone in the group got pretty wasted at a downtown bar. Most of the evening she was giving me these doughy eyes and always managed to be sitting near me. At some point the group got into some version of Never Have I Ever, not hardcore version, but with just enough racy questions that the erotic sensors in my brain started to kick on. And Carla was beginning to be more and more of my type as I downed pint after pint. She was definitely feeling it too, as she was now very obviously snuggling up next to me.

And I'[m] riding the stairway to heaven [f]

This was the first of a few encounters I had with my ex’s dad secretary. He was a big wig in an international engineering firm. He got me a job there as a low level consultant in my area. It was a pretty sweet gig cause I was not really part of the company’s grind of work and could really work when I wanted to. Anyway, this afforded me time to meet lots of people in the office. One of whom was the dad’s secretary, Teresa. She was a bit older than me, not outright hot, but blonde and great smile. She had a sharp sense of humor and whip smart (spoke three languages). We spent a lot of time outside his office chatting and joking, but nothing really sexual.

One night after work some of the engineers (not my girlfriend’s dad) were going out for drinks so they invited me. Teresa came along, too. Despite being the only female, I was impressed at how well she held her own. I remember her wearing boots with a skirty and a shirt with a plunging neckline. Very comfortable with the man-talk and flirtatious with it. I could tell she liked being in that role and got some vibes from her that she might be or have had a past with one of the married engineers.