My first time was with a very sexy executive assistant to a rather famous, Hollywood producer. She was almost ten years older than me, very connected in the film business and very well paid. She spent a lot of money on clothes, shoes, her hair, manicures, pedicures, everything. But not because she was exceptionally vain. It was pretty much a requirement for her job.
Anyway, it was like my second year in L.A.. I had a crappy administrative job with a film distribution company that happened to be in the same building as this pretty powerful, pretty intimidating woman. Anyway, I somehow made friends with her, I think by working up the courage to compliment her stylishness one day when we were alone in the elevator.
She smiled and took a liking to me and didn't seem to mind too much every time I passed her in the halls and attempted to chat her up. She brushed me off a few times, but eventually I got up the nerve to ask her out.
Turns out, despite all her money and connections, she was sort of lonely. And pretty kinky.
About two months after we started (secretly) dating, she called me one afternoon and told me to come up to her office because she had gotten her boss to sign one of his movie posters for me.
When I got up there, I found out her boss was having another one of his long lunch meetings. She scolded me for asking her to get the poster signed and asked how I intended to thank her for it. (apparently her boss had teased her and asked if the guy he was signing it for was her boyfriend, which she denied but didn't appreciate.)
So this sexy, kind of intimidating woman stood there with her hands on her hips and glared at me. Like an idiot, I had no idea how to answer her.
But she did.
She knew exactly how she wanted me to apologize.
Now this woman was about 5'5" in her bare feet but she had a penchant for wearing 3, 4 and even 6-inch stilettos. She also had a closet full of micro mini-dresses and black mini-skirts which she usually wore with tight, usually black nylon stockings. (She had been a semi-professional tennis player when she was younger and her legs were definitely one of her best features.
I'll never forget that black mini-skirt, frilly lavender silk top, those black stockings and 4" stilettos she was wearing that day. Now this woman wasn't particularly busty, especially not by L.A. standards. But she was an all natural B-cup and when she started playing with the second button on her blouse, I caught the wicked gleam in her intoxicating, emerald green eyes.
Pam ran her long, perfectly manicured fingers thru her salon-pampered, shag-cut shoulder length dark hair that she had just recently had highlighted with crimson red streaks. She closed the door to her office and told me to take off my pants. I pretended to protest, but obeyed. "Now the rest of it," she ordered from her observational vantage point by the door.
I asked when she was going to start taking off her clothes and she reminded me that I was the one who needed to apologize!
So there I was, standing stark naked in the middle of this executive woman's big leather couch, mahogany desk office with wide-open floor to ceiling glass windows. As you might guess, staring wordlessly at the petite little green-eyed vixen fully dressed in her stilettos and black stockings and black mini-skirt while she played with that second button on her blouse quickly started turning me into pure granite.
She grinned a perfectly naughty grin, told me to get on my hands and knees and crawl over to her.
I obeyed yet again. What else could I do? But when I was staring up at her from her feet, she suddenly announced she hadn't decided whether to forgive me yet or not. She stepped on my hand as she waltzed over to her desk, sat down in her big leather executive chair, crossed her legs and glared at me some more.